A few of the references have aged in the years since, but if you’ve joined us recently, it’s a great way into the back catalogue. If you’ve been around a while, we think it still holds up!

Apple podcasts

We’ve shared some highlights below, together with links & a full transcript. If you like what you hear/read, please leave a comment or drop us a review on your provider of choice.

Links

Apple Podcasts

Highlights

$1 million in gross profit, or your money back

Jimmy Soni: And so the audacious bet — the bet you started our conversation with — is you will make a million dollars in revenue by the end of your four years, or —

Nat Eliason: Gross profit.

Jimmy Soni: Gross profit, not revenue.

Nat Eliason: Not revenue.

Jimmy Soni: Wow. Even more audacious. So how does — without giving away state secrets, or anything privileged you can’t share — what was the thinking around that particular set of numbers, that bet, that promise? Because that’s the thing that’s been getting headlined.

Nat Eliason: Yeah, this was something Joe came up with when he came up with the idea for the school […]

Jimmy Soni: A million dollars in profit, or your money back.

Nat Eliason: Exactly. But he knew the same thing I said at the top of the conversation — there are no good entrepreneurship programs out there.

Jimmy Soni: Right, right.

Nat Eliason: There’s no undergraduate entrepreneurship degree that’s worth it, no graduate one that’s that good either. There are people who go to these schools and become successful entrepreneurs, but there’s really none of these schools that reliably drive outcomes in entrepreneurship. If you just said, “We’re launching a high school for entrepreneurs,” it’s kind of like, okay, right, there’s a lot of places for entrepreneurs — there’s FBLA, there’s all these things that say they’ll teach you entrepreneurship, and everybody kind of knows they’re not going to do that good a job. But if you say, “We’re launching a school for entrepreneurs, and if your kid doesn’t make a million dollars by graduation, we’ll refund you the tuition” — tuition is $150,000 a year, so we’re saying we’ll give you back $600,000 at the end of four years if we don’t get your student to that outcome. There are caveats — we’re assessing students each year, if a student comes in sophomore year they’re not on the guarantee, there’s all the edge cases. But that’s the core promise of the school, and it’s putting the pressure on us to actually figure this out, to make sure we’re delivering on these outcomes, and not playing startup like I was in college, trying to learn this for myself. It’s this incredible forcing function, and it’s the only reason anybody’s talking about this — because we have to be insanely committed to creating the best education experience possible on this topic, one that’s never existed before, that nobody’s made this kind of commitment to before. That’s where all our mental energy is going — we know this is possible, we just have to fine-tune it as we work with the students.

The perks of quitting early

Jimmy Soni: How did you deal with the feeling you described — you’re a year in and you realize it’s not going to work? Did it feel like the sky was falling? Because even at that age, even if you’re not building a business, you’re generally dealing with the challenge of what am I going to do with my earthly time — those are challenges for people who are just going to class every day. You’re building a business and watching it fail. What was your thought process, if you can think back?

Nat Eliason: I usually don’t stay in that headspace very long. I’ll have those feelings occasionally, but it very quickly shifts to: okay, well, there is something to do here. So I’ve never had long periods of wallowing, or being stuck in fear, because I very quickly click into, okay, we need a new plan — what is the plan, let’s focus on that. It shifted very quickly. I literally remember writing this on a whiteboard in my room — I wrote “$2,000,” because it was: okay, this startup is dead, I’m not working on this anymore, these illusions of raising $500,000 and going big — that’s not happening anymore. So what’s the thing I can focus on next? How do I get to this number by this date? That was the new plan. It felt like a very quick shift from focused on the startup to, oh wow, no, this is dead. I think it had probably been bubbling up for a couple of months, what was really going on. I must have spent some time making sure I wasn’t just having a momentary freak-out, because you don’t want to go that route either. But I remember it being a pretty quick and pretty adamant realization and decision.

For better or worse, I think I am good at that — okay, this feels like it’s hit a wall, but there’s this other vector that does have potential, I’m going to go on that one. That’s worked out very well for me. It’s also definitely had the downside of quitting things too quickly, or killing things too quickly, and it can be tough to find that balance sometimes.

Jimmy Soni: When you think back on that — because you’ve written publicly about quitting and talked a lot about it — do you have, sitting here in 2026, any updated thoughts on sort of knowing when to fold ‘em and knowing when to hold ‘em? Any new heuristics, or ways you’re thinking about it?

Nat Eliason: Yeah, I think ultimately — “quitting early” is the wrong term, but I’ve always had this bias toward being willing to kill something and move on to a better opportunity. The issue with that is it’s led to a lot of shiny-object syndrome. Most people, I think, go through a period of that, where they do this thing, then this thing, then this thing, and don’t get anywhere, and they realize, oh, I shouldn’t do that, I should pick something and focus on it. The issue for me is that it’s worked.

Jimmy Soni: Right.

Nat Eliason: Right. And I don’t mean this in a braggadocious way — it’s just, I’ve gotten away with it. I’ve been able to get super interested and fascinated in things, go hard on them for a year, launch these little businesses off my X account or my newsletter, and then they go really well. It’s like, okay, I can just become obsessed with something, dig into it for six months, then launch a course or a product, and it makes a few hundred grand in the span of a couple of months. Great — costs are covered for the next period of getting obsessed about things. That’s a cool ability to have. It’s incredibly powerful, incredibly useful, and I’m very grateful I’ve been able to do that.

But it does lead to not fully committing to things, not seeing where they can go, not living up to my full potential in a lot of those areas — because these breakthrough moments will happen, and instead of saying, okay, the excitement is over, now for the long slow slog to 10x this, it’s, well, I could just goof off for six months and then do this again. That’s been fun, that’s been satisfying. And then, really, last fall, I sat down — I ended up having this conversation with my wife, too — where I was like, I don’t think I should keep doing this. Even though it’s working, even though it’s provided a lot of the sustenance for our life, it feels like I’ve been playing this game a little too long. I really want to focus on something bigger, something serious, that has a meaningful risk of failure — because I think part of it comes from a fear of failure, a fear of trying something big and it not working and being embarrassed, because that means I’m not smart, I’m not capable. But as long as I’m doing these little things, there’s no risk of feeling that way.

Jimmy Soni: Because six months later, something else comes down the road and you figure that out.

Nat Eliason: Something’s going to happen.

Edited Transcript

Jimmy Soni: All right, Nat Eliason, thank you for coming on Infinite Loops.

Nat Eliason: Good to be here. Last time I did this with Jim. Now I got to do it with Jimmy. There you go.

Jimmy Soni: Yeah, we’re just going to continue rotating in people. Jim, Jimmy.

Nat Eliason: There you go. Have a cast of characters.

Jimmy Soni: One of the things that I have — this theory of the case of friendship that is like a contemporary case, or contemporary theory of the case of friendship — before the Internet, it was basically like, there’s less than a 1% likelihood you and I would have ever become friends. Because we grew up in different places. It would have been unlikely. Not impossible, just highly unlikely. And now what happens is you can have all these people who are Internet friends who become in-real-life friends. And so it’s this fascinating thing, because before, you would sort your friendships based on how close my locker was to yours.

Nat Eliason: Right.

Jimmy Soni: Did we grow up playing on the same little league team or something? And fast forward, you and I connected — I believe it was on Twitter, or when it was —

Nat Eliason: No, you emailed me. For the podcast, back in 2017, ‘18. Yeah.

Jimmy Soni: And then you sort of evolve from there, and you follow friends’ projects and you support them along the way. And so it’s a real pleasure to do this, because it actually shows you, I think, what’s different about friendship now — that would have been impossible 50 years ago, or highly unlikely 50 years ago.

Nat Eliason: Even 10, 15 years ago, I feel like a lot has changed. I certainly grew up in the era where “don’t talk to strangers on the Internet” was my parents’ number one concern with me getting on it, for decent reasons. And now at least half of my friends, if not more, I meet online first. I have this very vivid memory of 2018 — my wife, my now-wife, and I had just moved into our first house in Austin, and I invited a friend and his girlfriend over for dinner. About an hour before he showed up, she was like, “Oh, by the way, how do you know Adam?” And I said, “Oh, we know each other through Twitter.” And she was like, “What — you’ve never met this person in real life? Who are you bringing into our house?” And it was great. Adam and I are good friends now. But even then, that was odd — and she was totally fair to have that reaction. Now it’s just like, “Oh yeah, of course, that’s another person we met.”

Jimmy Soni: And it’s funny, because I think you accelerate a lot of friendships that way, right? Because you do feel like you’re kind of in each other’s heads in some way — you vaguely know the projects the other person’s interested in. Whereas with, call it, locker proximity, that still requires a fair amount of investment in a friendship before you know if you’re even interested in the same things. But with online or digital friendships that convert into real-life friendship, you’re like, I already know all the stuff you like. We like all the same stuff.

Nat Eliason: We follow all the same people. Our feeds are the same.

Jimmy Soni: It’s like you were already hanging out with them.

Nat Eliason: Yes. Although it does create these funny circles, where I have a much harder time being friends with Instagram guys than Twitter guys, because I just don’t know what’s in their feed. It’s almost like a relationship strategic thing — Cosette knows what’s going on in a lot of our friends’ lives that I don’t know, because I’m not on Instagram, and I know stuff going on in other friends’ lives that she doesn’t know, because she’s not on X as much.

Jimmy Soni: That’s really funny.

Nat Eliason: It’s strategic, almost.

Jimmy Soni: Do you get a little bit of — I don’t know if you have this — the six degrees of Chris Williamson? Or the problem of everybody consuming the same information?

Nat Eliason: Yeah, right.

Jimmy Soni: A little bit.

Nat Eliason: That’s definitely true.

Jimmy Soni: I think that’s true of all communities, but I think it might be particularly true of friends who are based on Twitter, X.

Nat Eliason: I have a group chat of guys who are also terminally online on X, and I swear, two-thirds of the time someone posts something funny in the chat, I’ve already seen it.

Jimmy Soni: Already seen it.

Nat Eliason: And it’s a weird experience — this world is big, and it’s really, really small.

Jimmy Soni: Well, we’re here to talk about your world expanding a bit and changing a bit. A lot has changed. But just for listeners who aren’t familiar with your particular path — can you sketch out... I think of you as like the Dos Equis guy of the Internet. You’ve had some of the most interesting career shifts, transitions, experiments you’ve run. Can you walk us through briefly — take me from your education at Choate to now, kind of bullet points, so people have a sense of who you are?

Nat Eliason: Yes. So, I guess the way I describe it is that I’ve been very fortunate to have made a career out of getting super fascinated and obsessed by things and diving down these different rabbit holes that have thin relations but not very thick ones. That’s been this fun journey over the last 12, 14 years. I went to high school at Choate Rosemary Hall up in Connecticut, and while I was there I thought I was going to go into physics. Then in the same year I took microeconomics and read Atlas Shrugged and got immediately red-pilled on entrepreneurship and business. So I kind of hard-pivoted — decided entrepreneurship and business was what I wanted to do, applied to really just the top ten business schools for college, went down that list, and then went to the best one I got into, which was Carnegie Mellon.

One year into business school at Carnegie, I realized it wasn’t going to teach me anything useful about entrepreneurship. It was great for learning finance and stuff that would be useful in a management consulting career, things like that — but really not much. There’s not much value in the entrepreneurship degree at almost any college or grad school. I dropped out of that into the philosophy program, because I still had that literary interest, but that was also the lowest-requirement major, so it gave me the most freedom to do whatever I wanted with my college degree. I ended up dropping out for a year to work on a startup, and convinced the business school and the philosophy school to give me credit — kind of independent-study credit — for working on my business, which allowed me to still graduate on time. So I got to hack the system that way.

Jimmy Soni: Which, by the way — just to pause here for a second, because there are either young people listening or parents of young people listening — one of the things I say when I’m speaking, because I did roughly the same thing: I designed my own degree at Duke. Basically, starting sophomore year, I was able to choose all of my classes through senior year. I designed it so I got to do exactly what I wanted, with who I wanted, and then just did a bunch of independent studies to fill in the gaps. I tend to think college — you’re in this business too — is far more hackable than people think it is. There are no rules. There’s nothing they actually have to do. You can make it up as you go along, and, by the way, get money to do it.

Nat Eliason: And once you graduate, no one’s really going to care what grades you got or most of the classes you took. So you either use it to get an extremely deep education on a challenging subject you couldn’t realistically get anywhere else — if you can study physics at MIT or something, you have the potential to get an education you can’t get anywhere else — or you do the bare minimum, get the piece of paper, meet everybody, because those are going to be your friends, possibly your wife or husband, your future business partners, all of that, and then focus on other stuff. I think the bimodal approach is the way to do it.

I ended up getting a lot of value in the sense that I spent that whole year off campus in downtown Pittsburgh, working on my startup with other adults. I went through a startup accelerator downtown — so it was me, the 20-year-old who couldn’t go out to the happy hours, and then all these other adults working on their startups. I was off campus during the day, learning business skills, interacting with people much older and further along in their careers, but then at night I went back to campus, stayed in my fraternity, threw parties, did all the fun aspects of college. That was the best year of college, by far. Best of both worlds.

Jimmy Soni: Did you — how did that business go?

Nat Eliason: Oh, terribly. I mean, it was the classic problem: one, I was a 20-year-old who’d gotten into good schools without herculean effort, and I knew I was smart, so I felt like I knew what I was doing. I’d read a couple of books, like The Lean Startup, and there was nobody around me saying, “You don’t know what you’re doing.” So I just assumed I did. I was able to raise a small amount of money, but I don’t think in that year we got a single paying customer. I was really good at making pitch decks —

Jimmy Soni: Which is a skill.

Nat Eliason: Which is a skill. It’s a skill. I was good at going to networking events, I was good at playing startup, but I did not actually learn how to start a business. About a year in — it must have been a book I read, because it wasn’t somebody who told me — there was this moment of cascading dread, when it all hit me at once: oh my gosh, I’m a fraud, this isn’t working at all, this is making no money, there is no product-market fit here, and I’ve just spent a year on this, and I could have figured this out probably eleven months ago. Very useful.

Thankfully, when I realized that, I very quickly went to: I need to shut this down, and I need to get my act together, because I’m graduating in eight months and I’ve been shirking a philosophy degree. So I have no job prospects that way — my startup has failed, so that’s not going to pay me — and I have about eight months to figure out how to make money or get hired, or else I’m moving back. I didn’t have a fallback plan. I was like, I’m just going to figure it out. And thankfully, I did. That was when I got really into content marketing and writing, because the question I asked myself was: okay, I want to get into startups, I don’t have any useful skills for that right now — I don’t know how to code, I don’t know how to design, I don’t know how to market, I don’t know how to do sales — what is the skill that would be useful to a startup that I’m closest to knowing how to do? I picked marketing, specifically content marketing, because I was a philosophy major, I was writing a lot. I figured, okay, I can figure out how to write good articles for a company blog, a startup blog, and that will get me my first jobs and internships.

So I started my blog, started writing articles on it just to demonstrate I could do content marketing, from what I could piece together from blogs that were out at the time. There wasn’t really — there wasn’t YouTube back then in the educational sense we have it today.

Jimmy Soni: Back in the stone age.

Nat Eliason: Yeah, exactly. There were no Twitter accounts I could follow — people were just posting about pooping on Twitter, there was no real network. But Zapier and Buffer were the two big future-of-content-marketing companies at the time. So I started my blog, posted on it for two months, felt like I was getting good, and then I just cold-emailed both of them and said, “Hey, will you take me on as a freelance writer?” I didn’t say internship, didn’t say college student — I was just trying to pitch them to hire me as a freelance writer. Buffer said no, but Zapier said yes. So by December — this is a two- or three-month period — I’d gone from nothing to: okay, I have my first freelance writing gig with this company I have a lot of respect for. It was $150 an article. I did the math and said, okay, if I do 12 to 14 articles a month, call it three a week, that gets me enough that I could afford to live somewhere like Argentina or Thailand. So now I know I can go do that when I graduate if I need to — I don’t need to take any job I don’t want to take, I can keep focusing on entrepreneurship skills, and I have this as the backstop.

That was really the first — you don’t think of freelance writing as entrepreneurial, but it was a very entrepreneurial thing to do. It was like, okay, I’m going to develop this skill, sell it, figure out my rough P&L to run that business, and go from there. I ended up taking a job for about eight or nine months that didn’t work out very well, but then started a marketing agency right after it, and it all started with making that decision senior year of college. That marketing agency ended up doing a few million a year — I stepped out of it, had another CEO take over, and she ran it for a few years before it was eventually acquired. That was my first entrepreneurial thing that did very well, and it all stemmed from that decision.

Jimmy Soni: Just out of curiosity — did your family, were they nervous? Were there any tough conversations? Because that’s usually the part of the story people leave out, right? One, one has to drop out of college — but the more complicated thing is usually not dropping out, it’s the phone call to the parents to let them know what your plans are. You didn’t drop out, but did they have any concerns — you’ve gone to Choate, you’ve gone to Carnegie Mellon, you’ve been in these worlds that are indisputably prestigious, and now you’re going to go write freelance articles and maybe move to Thailand?

Nat Eliason: Yeah. By that point they’d been warmed up to it from me doing that year off — that was the hardest of those conversations. I don’t think my mom was ever worried — she was like, “He’s going to be fine, he’s going to figure it out.” My dad is much more academic — he went to Harvard Law School, he’s a professor, it’s like, college is important. I think he was very worried I wasn’t going to get a degree. I think he knew, rightly, that as soon as I got a taste of not being in college, I’d never want to go back. It’s sort of a fluke that I ended up graduating, in the sense that if I hadn’t gotten all that extra credit, and if I hadn’t had so many APs from high school, I wouldn’t have finished — there’s no way. But after I shut down the startup and papered out the math with my advisor, we realized we could jam one semester full of kind of BS classes to get me to the finish line and still get the piece of paper. I think if we hadn’t been able to work that out, it wouldn’t have happened. But that satisfied him, at least, that I got the degree.

I think it was clear to them at that point that even if the startup hadn’t worked, I had started something, hired people, raised some amount of money — I was on some path. And I think if I’d said, “After I graduate, I’m going to figure out how to make money doing freelance writing,” that would have been one thing. But going to them and saying, “I’m already doing it, I’m already making it” — that helps a lot. It’s like, okay, clearly there’s a plan here, he’s on some sort of trajectory. Sometimes kids in high school or college reach out to me. They used to more when I was younger —

Jimmy Soni: You’re over the hill now.

Nat Eliason: No, well — I feel like when I was in my mid-20s I was more vocal about the college-alternative-path thing, so I’d get more of that inbound. I don’t get as much of it anymore. But I’d always say: make some money online first, then tell your parents, because they’ll be a lot more amenable to the idea if you have proof of success instead of just hoping it’ll work out.

Jimmy Soni: When you were raising money at 20 years old, how did you communicate with investors? What were those conversations like? Raising money is something even adults obviously struggle with mightily.

Nat Eliason: Yeah. Honestly, it was a lot easier for me, because it was from a local startup accelerator in Pittsburgh, and I was a Carnegie Mellon student. These guys are wonderful — I don’t mean this as a criticism — but they gave me a lot of benefit of the doubt because I went to Carnegie, and I’d just won the Startup Weekend in Pittsburgh with this idea. So I had that kind of charisma, and there was a bit of local excitement around what I was doing. It was kind of a natural fit in that sense. But looking back, if I’d gone out to Silicon Valley and tried to pitch YC, or tried to get in front of an a16z, I think they might have said, “You have no idea what you’re doing, you have nothing here.” That might have been very helpful, honestly. Even when I raised the follow-on money, it was from the same parent fund — a Pennsylvania innovation fund to support job creation within the state. So again, I wasn’t playing in the hardest leagues, and I think they gave me more trust because I went to Carnegie.

Jimmy Soni: How did you deal with the feeling you described — you’re a year in and you realize it’s not going to work? Did it feel like the sky was falling? Because even at that age, even if you’re not building a business, you’re generally dealing with the challenge of what am I going to do with my earthly time — those are challenges for people who are just going to class every day. You’re building a business and watching it fail. What was your thought process, if you can think back?

Nat Eliason: I usually don’t stay in that headspace very long. I’ll have those feelings occasionally, but it very quickly shifts to: okay, well, there is something to do here. So I’ve never had long periods of wallowing, or being stuck in fear, because I very quickly click into, okay, we need a new plan — what is the plan, let’s focus on that. It shifted very quickly. I literally remember writing this on a whiteboard in my room — I wrote “$2,000,” because it was: okay, this startup is dead, I’m not working on this anymore, these illusions of raising $500,000 and going big — that’s not happening anymore. So what’s the thing I can focus on next? How do I get to this number by this date? That was the new plan. It felt like a very quick shift from focused on the startup to, oh wow, no, this is dead. I think it had probably been bubbling up for a couple of months, what was really going on. I must have spent some time making sure I wasn’t just having a momentary freak-out, because you don’t want to go that route either. But I remember it being a pretty quick and pretty adamant realization and decision.

For better or worse, I think I am good at that — okay, this feels like it’s hit a wall, but there’s this other vector that does have potential, I’m going to go on that one. That’s worked out very well for me. It’s also definitely had the downside of quitting things too quickly, or killing things too quickly, and it can be tough to find that balance sometimes.

Jimmy Soni: When you think back on that — because you’ve written publicly about quitting and talked a lot about it — do you have, sitting here in 2026, any updated thoughts on sort of knowing when to fold ‘em and knowing when to hold ‘em? Any new heuristics, or ways you’re thinking about it?

Nat Eliason: Yeah, I think ultimately — “quitting early” is the wrong term, but I’ve always had this bias toward being willing to kill something and move on to a better opportunity. The issue with that is it’s led to a lot of shiny-object syndrome. Most people, I think, go through a period of that, where they do this thing, then this thing, then this thing, and don’t get anywhere, and they realize, oh, I shouldn’t do that, I should pick something and focus on it. The issue for me is that it’s worked.

Jimmy Soni: Right.

Nat Eliason: Right. And I don’t mean this in a braggadocious way — it’s just, I’ve gotten away with it. I’ve been able to get super interested and fascinated in things, go hard on them for a year, launch these little businesses off my X account or my newsletter, and then they go really well. It’s like, okay, I can just become obsessed with something, dig into it for six months, then launch a course or a product, and it makes a few hundred grand in the span of a couple of months. Great — costs are covered for the next period of getting obsessed about things. That’s a cool ability to have. It’s incredibly powerful, incredibly useful, and I’m very grateful I’ve been able to do that.

But it does lead to not fully committing to things, not seeing where they can go, not living up to my full potential in a lot of those areas — because these breakthrough moments will happen, and instead of saying, okay, the excitement is over, now for the long slow slog to 10x this, it’s, well, I could just goof off for six months and then do this again. That’s been fun, that’s been satisfying. And then, really, last fall, I sat down — I ended up having this conversation with my wife, too — where I was like, I don’t think I should keep doing this. Even though it’s working, even though it’s provided a lot of the sustenance for our life, it feels like I’ve been playing this game a little too long. I really want to focus on something bigger, something serious, that has a meaningful risk of failure — because I think part of it comes from a fear of failure, a fear of trying something big and it not working and being embarrassed, because that means I’m not smart, I’m not capable. But as long as I’m doing these little things, there’s no risk of feeling that way.

Jimmy Soni: Because six months later, something else comes down the road and you figure that out.

Nat Eliason: Something’s going to happen.

Jimmy Soni: Why last fall? Was there something going on that occasioned that “maybe I need to stick with one thing for a while”?

Nat Eliason: I think it was a combination of things. One, I’d been doing sci-fi writing for a year and a half, and it was clear that wasn’t going to pay the bills. While that had been going on, I’d been super deep in building with AI, learning how to use these tools, and I launched a course on learning how to vibe code before “vibe code” was even a term — nobody had used that word yet, Andrej hadn’t coined it. It was basically the first big vibe-coding educational thing out there. It did about $250,000 in sales in a weekend, went on to do half a million over the course of the year, with basically no ongoing work after that first set of recordings, plus an update in October — a breakout success. And I’d seen a lot of people who came in after me, some of whom took my course and then actually committed to doing something with those skills, building a product, building a bigger education business — and I realized I’d been so early, I’d established myself in that topic area, and then had just completely let that opportunity go. Maybe there’d never be another opportunity like that in my life — I don’t actually believe that, but it’s a consideration. Looking at that was hard. It was like, wow, I nailed this timing, and then I just did nothing with it, I just let it go. That felt like a mistake.

I think being a parent contributes a lot to it, too — would I tell my kids to treat opportunities that way? Definitely not. If they came to me and said, “What should I do with this?” I’d say, obviously you should keep going.

Jimmy Soni: That’s right.

Nat Eliason: So it’s like, okay, well, why wasn’t I doing that? It made me want to do something bigger, or fully commit to something. That started that thought process last fall, and then I spent the next four, five, six months figuring out what that could be.

Jimmy Soni: Well, we’ll cover some of the other topics from earlier in your adventures, but that brings us to what you’re doing now — which is one of the most interesting things I’ve seen in your career evolution, just the portfolio of stuff you work on. Tell us a little about the result of that soul-searching last fall, and what you’re up to today.

Nat Eliason: Yeah, so I’d basically made this decision last fall — okay, I’m going to put the book work on hold, take something from this interest in technology, and really just go all in on it. So I started spending all of my time going even deeper than I had before on building with AI, using AI — what is interesting here — and had started working on one product, which led to another and another, and was kind of going down that path.

Then there was this tiny trickle of a side quest, where Cameron Sorsby was working at Alpha School and he’d DM’d me on Twitter — all roads lead back to X, all good things come from X — and he said, “Hey, I work at Alpha School, I’m working on this new high school program for entrepreneurs, I want to help the kids level up their AI skills, would you be down to come in and do a workshop for them?” I already knew about Alpha School at that point — part of why I liked being in Austin was knowing I could send my kids to Alpha School. To me, it was, and still is, the most interesting thing happening in education. It’s the one school I’d most want to send my kids to, and I liked being there. Honestly, one of the first thoughts through my head was, oh, this is how I get my kids into Alpha School —

Jimmy Soni: They’ll discount the tuition.

Nat Eliason: Exactly — I get in the good graces now, and then when I apply next year for my kindergartner, I’ll get through the application process because I’m already on the inside. I was literally thinking that. It wasn’t completely selfishly motivated — there was a bit of that, but there was also a bit of, oh, this sounds super fun, super exciting, of course I want to come do an AI workshop for these high schoolers, in part because I was curious to see what an Alpha School high schooler is like, from everything I knew about the school.

So I went and did a modified version of my “building with AI” course for these high schoolers, and was just blown away — they were super sharp. A lot of them had already started working on business ideas or had already built audiences — a couple had over a million followers on TikTok. They were asking better questions than a lot of adults I’d done this stuff with, and they could take feedback extremely well, which maybe stood out the most. There’s a natural fear when working with students that you have to put on kid gloves, but they were very eager to hear, “This part of your landing page is ugly, you can change the copy like this, this is broken, you need to go harder here” — they were super receptive to it. I loved doing the workshop.

Jimmy Soni: And how long was the workshop — a couple hours, a half day?

Nat Eliason: Like a half day, four hours — a little bit of talking, then independent work sessions, then coming back together, then independent work again, so it’s flowing back and forth over the course of an afternoon. After we did that, Cameron and I were hanging out and talking more, and he told me more about what he’d joined Alpha School to do — this new high school for entrepreneurs, what’s now called Founders School — where they’d promise that students would make a million dollars by graduation or get all their tuition refunded. My immediate reaction was, that is the worst business idea I’ve ever heard — do you realize what you’re committing to here? But then I thought about it some more, thought about what I’d seen with the students, and — obviously I was super deep in building with AI, had seen what a lot of other teens out there were doing with AI, what teens were doing starting businesses without this kind of support — and I very quickly got to the point of, oh, this is actually doable.

It sounds insane, but you combine what Alpha’s done with academics, being able to compress the whole high school day to about three hours, which gives you four to five hours of hands-on workshops, instruction, mentorship, and support specifically on entrepreneurship in the afternoon — you take that out across four years, add in what AI lets a teenager do — and you fit all those pieces together, and you realize, oh, this actually makes all the sense in the world, especially if you get the right people in the room to help them, because it can go the wrong way if they have the wrong support, wrong mentors, wrong guidance. But get the right people in there, and this could work.

So he just asked, would I be down to chat with him occasionally as he planned this out. I said, yeah, this sounds awesome, I’d love to come in and talk to the students, be a mentor or whatever. We were just talking about it for the next two, three months, while I was working on all these other AI projects. After a few months, I’d found something that was really taking off with the AI products — stuff related to OpenClaw and agents — and side conversation, and I was basically in the middle of launching that when Cameron and I hung out again. He said, “I think for this school to work, I need somebody who is super entrepreneurial, super AI-driven, good at quickly getting things from zero to one to B, on the ground, working with the students, designing the curriculum, alongside me.” Cameron’s a great educator — he’s been building college-alternative programs for the last ten years, knows all that stuff — but he’s not as deep on the AI side or the hacky-solopreneur side as I am. So he was basically like, “Do you know anyone who’d be good to come do this with me?” And I said, “You’re looking at him.”

It was one of the strangest moments of my life, because I had not thought about it at all before that moment — there was no part of me that was like, oh, I’m going to drop everything and be a co-founder on a high school. But as soon as he asked that, and put that seed of “somebody needs to come do this with him” — it was like, oh, it’s me. I said, “I need to talk about this with my wife.” I think I just went silent for a minute, kind of staring at him as I processed it all. What I said was, “It’s not a no.” And I could see him go, “Wait — what, this is an option?” I went home and told Cosette, “This is happening,” and she said, “You have to do this.” It immediately was like, this has to happen. I think this was a Friday, and I showed up Monday and just started working — didn’t get officially hired for another month, because, you know, it’s a big company, you have to go through HR, other interviews, negotiate comp, do all the big-company stuff. I was like, I don’t care, I’m just going to show up and start doing this with you, we’re going to make this happen. And then I had to shut off everything else.

There was an evolution to the school that we might get into, where at first I thought I’d still do some of my side stuff —

Jimmy Soni: I was going to ask that — did you see yourself doing this as another side hustle?

Nat Eliason: It started that way, because in the beginning this was going to be a program for students in Austin — for students who were already at Alpha School, the Alpha High School in Austin — and then it very quickly evolved into, this should be its own dedicated high school program.

Jimmy Soni: Can you walk us through that evolution? Because when I first heard about this, I thought, oh, Nat’s going to be running programs for Alpha School — and then it was, no, no, there’s a thousand-person high school, the ambition is to build a thousand-person high school in the middle of New York City. And then I texted you and you were like, “I live in New York now.”

Nat Eliason: Yeah, yeah.

Jimmy Soni: You really burned the boats there.

Nat Eliason: Oh, yeah. We had that conversation where I decided to join, beginning of February, and then we were planning out the programming for it over the next six weeks — what would it look like as part of the high school, what would we teach, who are the mentors we want involved — kind of the program-level structure. Then I did a workshop for the Austin students on using OpenClaw — for anybody who doesn’t know, it’s a way of using an AI agent that unlocks it and gives it superpowers in a way you don’t get if you’re using Claude Cowork, or even Claude Code, or the Codex desktop app, or Perplexity Comet — all these other agentic things have a certain amount of ability to act on your behalf, but this is the next step beyond, in terms of what it allows you to do. It brings a lot of risk with it, because you’re giving it a lot of unfettered access to things, but if you build it right, it’s the closest thing to having a human working alongside you. I’d ended up adopting it pretty early, again kind of gotten away with very quickly building a ton of following, just by being excited about it, posting about it on X constantly — not in a malicious way, I was just obsessed with this. The students started asking, “Hey, can we do a workshop on this?” I said, sure, that sounds great. Did a couple of workshops on OpenClaw with the Alpha students, then the Alpha parents in other cities heard about it and said, “Wait, can you come do this with us?” So, beginning of April, we come out to the New York campus to do the OpenClaw workshop with the New York students and their parents.

While we’re doing the workshop, Cameron and I start casually talking about Founders School with the parents, and they’re all like, that’s the most incredible idea ever, you have to come do it here. They started mentioning people they knew whose kids would be a good fit — there was this immediate excitement, interest, and possible students who were a fit for it that we hadn’t run into yet in Austin.

Jimmy Soni: Did that surprise you at all? I would have thought you’d have had to ship out to San Francisco, or stay in Austin —

Nat Eliason: It surprised me at first. But then the reason it ended up making sense is that demand is absolutely there in Austin in five to ten years — Austin is a young, entrepreneurial city, people are moving there earlier in their family’s lives. So the pre-K, first-grade, second-grade, third-grade demand for Alpha is overwhelming. But there aren’t as many people who come from this entrepreneurial background, or ultra-high-net-worth background, with teenagers, who’ve come to Austin looking for this. So there’s a bit more of that demand here. And when you look at the elite high schools we’re competing with — the Horace Manns, the Exeters — much more of those are on the East Coast than in Austin.

That kind of drove the thinking, along with the parent excitement — it became clear that we’re going to have more demand for these students in New York City, initially, than in Austin. But Cameron was living in Austin, I was living in Austin with my three kids, Joe, our principal, is in Austin, and the New York campus is new — New York only started last year, but the New York team was really excited about it. It was this funny thing where I think everybody arrived at the “we need to do this in New York” conclusion at the same time, independently, but nobody wanted to bring it up first. So there was this little dance for about a week, and then we all kind of said it at once, and it was like, oh yeah, obviously that’s what we’re going to do. That was mid-April, and June 1st, I moved here.

Jimmy Soni: All right, so we are in medias res — we’re in the middle of this.

Nat Eliason: Yeah, yeah.

Jimmy Soni: So what is it — how is Founders School going to be distinct from Alpha School?

Nat Eliason: Yeah. The core premise of Alpha is that, one, students should love school, which sounds obvious, but it’s not a given at all — a lot of parents have just accepted that their kid is going to be bored in school and that’s part of life. So we say, no, the number one mission of this school is that kids will love it. One of the main ways you let kids love school is if you give them a good reason to get the academics done besides “I told you to” — because normally you get academics done because otherwise you get in trouble at school, or with your parents, or maybe your parents give you some money for good grades on your report card.

Alpha takes it to the max, where we say we want to make it as rewarding as possible to get your academics done. First, we compress it to two hours a day in K through 8, three hours in high school, through an AI tutor that knows exactly where you are in reading, math, writing, science — everything — and gives you the exact next thing you need to learn to progress toward mastery for your age. You’re never sitting in a lecture, bored, waiting for somebody to catch up. You’re never slowed down if you’re interested in a subject — you’re getting the exact right challenge for where you are. That lets you do the whole day in two hours.

You’ll have people say, “Well, then they’re in front of screens, working with AI” — I understand why people are concerned about that. But then you talk to the students, ask them, and the test scores are better — you could argue it’s the highest-performing private school in the country, for a lot of these measures, especially K through 8. You ask the kids, would you rather sit in classes all day, or do these two hours on your laptop in the morning? Every single one says they’d rather do that. We used to survey our students, “Do you love school?” — that was one of our most important surveys at the end of each session. But we stopped, because 90, 95, 98% would say yes, I love school — it stopped being a useful measure. So now we ask, “Do you like school more than vacation?” And 54% of students say they’d rather go to Alpha School than go on vacation.

Jimmy Soni: Wow.

Nat Eliason: That’s an insane metric.

Jimmy Soni: That’s an NPS any business would be proud to have.

Nat Eliason: Right. But the way that happens is the compressed academics are one part of it — the reward, the benefit of that, is that you’re doing awesome stuff the rest of the day. It’s still a full school day, 9 to 3:30, but the academics are done by 11:30, and then you have three or four hours to do other awesome stuff. Those change throughout the year, and by grade level, but they’re focused on some kind of life-skills workshop where students are doing something fun while building an important life skill — often pretty ambitious for their age group. For example, one of the ones kindergartners do is a two-month session where they climb a 40-foot rock wall.

Jimmy Soni: Wow.

Nat Eliason: They go to a local climbing gym, harness up, and day one they go one step up the wall and they’re all cheering for each other because they got on the wall. The next day, two steps, three steps — you do that over two months, and by the end they’re going 35, 40 feet up this wall, while their friends cheer them on. The parents are terrified, but then they see how proud their kid is, they see their peers cheering them on, and that’s what they’re spending most of their day on instead of sitting in a lecture hall. So you ask a kid — would you rather sit in a lecture for most of the day, or get your academics done and then go rock climbing the rest of the day?

Jimmy Soni: Right. My take on Alpha School — which I’m a huge fan of, I hope my daughter enrolls at some point, she’s taking a different tack at least through middle school, we’ll see what happens with high school — is that some people think it’s a bet on the reinvention of education. I don’t. I think the more accurate statement is it’s a much safer bet on how kids already are wired. My daughter’s creating things all the time — it just doesn’t happen within the four walls of her school. This isn’t a knock on them, it’s their model, but in some ways it’s actively penalized — the things she wants to do to get ahead, to break the rules a little, aren’t encouraged. It feels like what Alpha’s doing is catering to the inborn instincts of children —

Nat Eliason: Right.

Jimmy Soni: — as opposed to reinventing. They’re reinventing the system adults created, but kids are actually very naturally wired for these kinds of environments.

Nat Eliason: Kids are natural learners, they’re naturally curious. This was a really long way of me answering the question you started with —

Jimmy Soni: No, you segued it back perfectly.

Nat Eliason: Because part of Alpha’s ethos is that every kid is naturally motivated by something — there’s something they’re just wired for. There’s this great Slate Star Codex article, “The Parable of the Talents,” where it’s not so much that everybody is born with some innate talent for piano, or running, or writing, but we’re often born with a fascination — something we naturally gravitate toward. And by gravitating toward something you want to do more of, it’s kind of self-rewarding. Most things in your life won’t be that way — that’s why you get paid to work and do all these other things. So if you can find what a kid is naturally drawn to do, and free up their day to do a lot more of that, they’ll get through the academics way more efficiently, with much deeper mastery, than in the normal system.

Alpha School has created all these different schools to cater to different students’ fascinations. Alpha is the one most people know best — it’s the most well-known, kind of the elite private school, and Alpha’s afternoons are focused on these workshops, and when you get to middle school and high school, you get to pick a big passion project to dedicate that time to. But we have other schools, like the Texas Sports Academies, where you get your academics done in the two hours in the morning and then spend the whole day playing sports. For a lot of kids, that’s what makes them perform — it’s like, oh, you just have to get your two hours of math and reading done and then you can play basketball, volleyball, or baseball for six hours.

Jimmy Soni: Right.

Nat Eliason: It’s like, yeah, I’m going to get it done.

Jimmy Soni: So when did the thinking evolve to the point that Founders School was going to be its own entity, rather than simply a track within Alpha School — because you’re going to be admitting students who know they’re going to Founders School, right? Is that correct?

Nat Eliason: Yes, yes. It evolved from this model Alpha had started at K through 8 — Sports Academy is for kids who are into sports, Waypoint is where kids are horseback riding and doing archery and rucking and outdoor activities, GT School is hardcore, more academics in the afternoon. We’d started this model at the younger ages, and we said, okay, what are the high schools that should exist? Alpha High is the one where you can explore anything you’re passionate about — it’s very open-ended. We have a student going for the Olympics in rowing, students writing novels, a student putting on a Broadway play, students starting businesses — and it was actually partially their idea to do Founders School, because the thinking was: okay, if you’re really serious about building a business in high school and want to be held to even higher expectations, but get even more crazy support to go after it — this is the school for you.

So it’s stepping up the expectations — obviously we have a longer school day.

Jimmy Soni: So it’s longer than the usual Alpha School day.

Nat Eliason: Yeah, it ends at 5 instead of 3:30.

Jimmy Soni: Why that choice? That’s an interesting design choice.

Nat Eliason: More time. It’s kind of like — if you were going into an apprenticeship in the pre-school era, you’re deciding at 14, 15, 16 that you’re going to become a master blacksmith, and nobody should be able to say, “No, you have to go do these other things before you become a blacksmith,” if you know that’s what you want to do. Obviously our students are still held to very high academic standards — we’re still doing all the academics, they’ll still be in excellent shape for college — but if they know entrepreneurship is what lights them up, and that’s what they’re going to be doing when they go home anyway after school, they can just stay with us longer.

Because the great thing about how we’ve designed Founders School is there’s programming, curriculum, and structure, but it’s also very heavily tailored to provide the exact support the student needs at wherever they are in their business. So instead of a month or two, or a semester, of tons of classes on Facebook ads, if we see a student is at the point where they might start experimenting with Meta ads, and that’s something they want to explore, we get them one-on-one support with an expert who’s a practitioner in the field — somebody running an ads agency or something — whose time we’re buying each week to work with our students, train them, mentor them, audit their process, and help them learn that specific skill right when they need it. So they’re getting this incredible amount of support for anything they might run into in their business, along with the coaching, emotional support, and encouragement that’s standard for Alpha across both academics and extracurriculars.

Jimmy Soni: Got it. And so the audacious bet — the bet you started our conversation with — is you will make a million dollars in revenue by the end of your four years, or —

Nat Eliason: Gross profit.

Jimmy Soni: Gross profit, not revenue.

Nat Eliason: Not revenue.

Jimmy Soni: Wow. Even more audacious. So how does — without giving away state secrets, or anything privileged you can’t share — what was the thinking around that particular set of numbers, that bet, that promise? Because that’s the thing that’s been getting headlined.

Nat Eliason: Yeah, this was something Joe came up with when he came up with the idea for the school. Remember what I said at the beginning of the conversation —

Jimmy Soni: Can you say a little bit about Joe, so people have context on who he is — there are people learning about Alpha School for the first time.

Nat Eliason: Yeah, okay. Joe Liemandt joined, came in as the second co-founder for Alpha School about five years ago. Alpha was originally started by MacKenzie Price in 2014 — she ran it as a school in Austin using these principles of direct instruction, one-on-one mentorship, spending most of the day on activities, and pioneered the overall structure for the school, with incredible success. Joe founded a software company in the ‘90s called Trilogy — it’s grown, and he’s the sole owner of it now, a multi-billion-dollar company, massive successful tech entrepreneur. His daughter ended up going to Alpha in Austin, and that’s how he found out about it — he fell in love with the model, was amazed by what MacKenzie had figured out about teaching students this way. He’d actually sold one of the first pieces of software that was, like — it was Salesforce before Salesforce, is a way you could describe it, back in the ‘90s — so he’s been obsessed with the potential of AI for 30 years now. When generative AI came on the scene, he basically went to MacKenzie and said, this is how we take what you’ve figured out and bring it to a billion students. That’s the core mission of everything we’re doing at Alpha — how do we bring the best education possible to a billion students around the world? It’s kind of like the Tesla model — we’re starting with the Model S, the Roadster, we need the expensive one first, and then we’re able to bring it down-market to broader audiences. So he brought in the software side, invested a significant amount of his own capital, and started building out the Alpha that more people have heard of today.

He’s obviously an incredibly successful tech entrepreneur — he saw the students at Alpha who are really entrepreneurial, and between the two of them, they came up with this idea for Founders School — the school for entrepreneurs.

Jimmy Soni: A million dollars in profit, or your money back.

Nat Eliason: Exactly. But he knew the same thing I said at the top of the conversation — there are no good entrepreneurship programs out there.

Jimmy Soni: Right, right.

Nat Eliason: There’s no undergraduate entrepreneurship degree that’s worth it, no graduate one that’s that good either. There are people who go to these schools and become successful entrepreneurs, but there’s really none of these schools that reliably drive outcomes in entrepreneurship. If you just said, “We’re launching a high school for entrepreneurs,” it’s kind of like, okay, right, there’s a lot of places for entrepreneurs — there’s FBLA, there’s all these things that say they’ll teach you entrepreneurship, and everybody kind of knows they’re not going to do that good a job. But if you say, “We’re launching a school for entrepreneurs, and if your kid doesn’t make a million dollars by graduation, we’ll refund you the tuition” — tuition is $150,000 a year, so we’re saying we’ll give you back $600,000 at the end of four years if we don’t get your student to that outcome. There are caveats — we’re assessing students each year, if a student comes in sophomore year they’re not on the guarantee, there’s all the edge cases. But that’s the core promise of the school, and it’s putting the pressure on us to actually figure this out, to make sure we’re delivering on these outcomes, and not playing startup like I was in college, trying to learn this for myself. It’s this incredible forcing function, and it’s the only reason anybody’s talking about this — because we have to be insanely committed to creating the best education experience possible on this topic, one that’s never existed before, that nobody’s made this kind of commitment to before. That’s where all our mental energy is going — we know this is possible, we just have to fine-tune it as we work with the students.

Jimmy Soni: How do you avoid the undue pressure? You’re in the early innings of this — it’s actually fun to talk about while it’s still being figured out. How have you thought about not putting that pressure on the students themselves, for that gross-profit-or-money-back burden?

Nat Eliason: Yeah, okay. We’ve actually had a couple of parents say they don’t want to do the guarantee.

Jimmy Soni: Oh, wow.

Nat Eliason: Right, for that exact reason —

Jimmy Soni: Okay.

Nat Eliason: They’re like, I don’t want my — I always say “student,” because kids don’t like being called kids — I don’t want my kid to feel like they have to hit this or I’m going to be —

Jimmy Soni: Right.

Nat Eliason: It’s like, yeah, obviously, we don’t want that either. It’s first and foremost an offer to the parents — it is the most expensive high school in the country, aside from IMG maybe. That’s how much we’re investing in the students — there’s no other school that’s going to get your kid on the phone with a top-tier Meta ads expert the next day when they have trouble with their ads account. It’s a huge investment, and we’re saying, this is what we’re willing to commit to. But we don’t want to create unpleasant pressure on the students — and it factored into how we ended up at the gross-profit calculation. We want the most aligned structure —

Jimmy Soni: Yeah.

Nat Eliason: — while creating minimum adverse incentives. So, okay — we can’t do valuation.

Jimmy Soni: Right.

Nat Eliason: Because,

Jimmy Soni: Right, valuations can be made up every day.

Nat Eliason: “Oh, I sold 1% of my company for— Exactly. We’re not going to do that, because then they might not learn anything —

Jimmy Soni: Yeah.

Nat Eliason: — because part of this is how do we make sure they learn the most. So then, revenue — we don’t really want to just do revenue either, because then they could be incredibly unprofitable, they’ve made money, they’ve built some business, but it’s not necessarily a good business. So we went from that to, okay, net profit then — because we want them to not just spend infinite money on ads, spend $10 million on ads to get a million in revenue because mom and dad funded it. We don’t want that. But then we realized the problem with net profit was that we’d create other adverse incentives, where we’d be telling students not to reinvest in their business.

Jimmy Soni: Oh, that’s fascinating.

Nat Eliason: Right — we were like, well, shoot, we don’t want that either.

Jimmy Soni: Them to take money out in order to avoid — for their parents to get back the $600K.

Nat Eliason: Exactly. We didn’t want to be going to the students and saying, “No, don’t run ads, don’t do another production run, don’t hire an employee, because we need to make this number happen.” So that’s how we ended up on this gross-profit calculation — we’re going to factor in a certain amount of cost of goods sold, and — you probably wouldn’t normally put advertising and stuff in there, but we’re going to put that in too — but we’re not going to try to disincentivize you from growing your team or reinvesting in the business, because there might be a student who builds a $10 million business, and — I mean, that sounds insane sometimes when you say it in front of parents, but I think that’s fully possible in four years, just seeing some of the students who are applying, who are already making progress. Zach Yadegari — he’s 19, and he sold Cal AI for fifty million dollars.

Jimmy Soni: Wow.

Nat Eliason: And he was going to a normal school — he had to figure this all out on his own. It’s like, this is possible. The reason we have to put so much thought into it is that we want the best structure possible for everybody — it’s not about trying to get out of something, it’s the thing we care most about, providing the best entrepreneurial education for these students, something that’s never existed before, that they wouldn’t need to go to any of these graduate entrepreneurship programs afterward. One of my personal KPIs is that they could teach a class at places like HBS when they graduate — if they can’t teach a class at HBS, I’ve failed. That’s what we’re aiming for.

Jimmy Soni: Yeah. So — I understand the part of Alpha School that’s about compressing an ordinary school day into two to three hours, that makes all the sense in the world, it’s almost table stakes at this point, because of Alpha School’s success — by the way, that’s not a knock, they did it, they proved it, you kind of accept it, and if you don’t accept it you’re just not looking at the numbers. What’s the program design like for Founders School specifically, after you’ve checked the boxes on academics in the morning?

Nat Eliason: So academics are done in the morning, and then we have the students from basically 12 to 5 for the entrepreneurial section. About 70% of the week is independent work time — or, if they’re working with another student as kind of co-founders, working together — on whatever stage they’re at in their business. One of the things we realized really early and really quickly was that just as Alpha School can’t rely on finding incredible second-grade math teachers in every location — the software needs to provide excellent support — we too, at Founders, need to create the best software to support an early entrepreneur wherever they are in their journey.

A lot of it starts with three axes we think are most important for them to figure out to get started. The first is developing expertise — a fun tie-in for me, because I spent years as a personal-knowledge-management writer, went very deep on this topic, how do you teach yourself things, how do you learn things. Now AI has both given us superpowers in that sense, but it’s also given us this incredible crutch — people will just sling slop.

Jimmy Soni: That’s right.

Nat Eliason: Right — they’ll make a document about a topic and then you ask them a question about it —

Jimmy Soni: And they have no idea what they are talking about.

Nat Eliason: They have no idea what’s in it. So the thing we start every student with is: I know you want to go build a business, I know you want to go work on a business — but you don’t get to do that until you’ve demonstrated you’ve developed some meaningful knowledge and expertise in a subject area, so you can actually build a business there. Because the number-one thing we see with students starting businesses is they start things related to school — sometimes that’s a good idea, sometimes it’s good ed tech, that’s a good business — a lot of times it’s not. Or they start businesses for other teens who don’t have money — just not the right market to go after.

So the first thing we do, the first thing we’re pushing them toward, is: start just thinking of topics you’re interested in, and go through this process of building expertise, building deeper knowledge, teaching yourself, being able to explain what you’re learning, and see where that leads you. Because if you don’t have a somewhat unconventional point of view on a topic, it’s going to be hard to carve out a real competitive advantage in almost any business you’d want to go into. So we start them there.

Jimmy Soni: And what does that look like — do they read, do they talk to people, a mix of both? What does that time look like where they’re developing expertise?

Nat Eliason: So it’s a mix of —

Jimmy Soni: Or what do you want it to look like, since you’re still building it?

Nat Eliason: Yeah, yeah. So this is the tool we’ve gone the farthest on, because it’s the foundational element, and it looks like a mix of reading and talking to people, but then doing their own research and kind of annealing — like sharpening a samurai sword — consolidating their opinions based on these sources into defensible positions on these topics. A little bit like what you might do in thesis research in a PhD program, but with the support of good technology that uses AI to challenge you, help with your research, expose you to new ideas and directions, without doing the work for you. You can almost imagine there’s aspects of Readwise, and of Roam and Obsidian, but in this kind of narrow context — pushing them to focus on one area, so they’re not just sprawling in tons of directions.

Another part is audience and network building, because the second big challenge of becoming an entrepreneur in high school is that not only do you not have any expertise or experience, you don’t know anyone. You might have some family connections, the Alpha connections, but that’s kind of it. So we’re pushing them, in a healthy way, to get online — predominantly X, because that’s where we see the most ROI, or LinkedIn — and find the people who are the experts in this subject area, follow them, engage with them, see what they’re talking about, and try to thoughtfully engage with them while building a bit of an audience themselves by sharing their thoughts. One of the most honest measures of whether you’re developing interesting thoughts on a topic is if you start getting responses — not engagement in a negative, viral way, but if other smart adults are thoughtfully replying, you’re getting somewhere.

So we’re helping them build expertise and actual industry establishment through things teenagers never had access to before — AI, the Internet, social media — but being used in a good, pro-education, pro-learning way, not a slop-and-doom-scrolling way. It starts there, and they’re going to be pissed at me, because they want to vibe-code and I’m gonna say you can do a little of that in your free time, but if you don’t start here, that stuff is never going to work. Start here.

We do that, and then they move into our co-founder tool, basically — working with a mix of that, our guides, our entrepreneurs-in-residence, our mentor network — okay, I’ve developed these points of view, started to make some connections, talked to people in the industry and gotten their perspective, these are some of the ideas I think are interesting. Exploring as many of those as possible at first, being challenged on them by the tool, but also by us and by the people they’ve connected with in the field. We have strong opinions on this, a lot of it influenced by Joe — I’ve had the privilege of spending a lot of time with him, learning how he thinks about business, technology, and opportunities, and we’ve built a lot of that into the product. So the students are almost getting direct support from him through the tools, and from him actually coming to the school and working with them as they form these ideas. It helps them move through this process of getting to the validation phase — you came up with something that’s a good idea, a good plan to get to a reasonable scale in a reasonable amount of time, you’ve validated it, made some kind of MVP, some basic version, you’ve charged money for it, and now you’re set up to do the flywheel — try something, see if it works, hit a bottleneck, ask us for help getting through that, and we’re checking in with you every day, during standups, internal reporting, to figure out where those challenges are and get you the exact support you need for whatever’s next.

Jimmy Soni: Got it. Is it businesses in general — are you thinking about businesses where they’re going to have to hire people eventually?

Nat Eliason: I mean, I love that idea — if we have a 16-year-old with a team of ten people in their 20s, 30s, 40s, oh my gosh, that’d be incredible.

Jimmy Soni: But seriously — are you anticipating that? I guess at the beginning you’re saying a lot of these businesses could theoretically be run with small teams, or one person.

Nat Eliason: Yes. I’d prefer their ideas allow them to get to that million-dollar mark without hiring anybody — ideally clever use of AI, good pricing strategy, good market opportunity, that’s completely reasonable these days. That’s what we’d nudge them toward. I wouldn’t want them to try to do, say, a dog-waste pickup service where you need to hire a bunch of people at minimum wage and monitor them — one, for the legal logistics, because they’re minors —

Jimmy Soni: They’re minors.

Nat Eliason: Which does introduce a lot of real challenges — they can’t open bank accounts, can’t sign legal forms. It’s a conversation we have to have with the parents too — hey, you’re cool with this, right, because they’re going to be building a business and your name has to be on it as well. They’re all cool with it, but it does create these weird bottlenecks, where you do kind of have to bias toward software, certain tech, e-commerce — things where it’s a little easier to get some of that initial scale, than if you have to immediately hire. Also, a lot of people in their 30s probably don’t want to work for a 16-year-old.

Jimmy Soni: Of course not.

Nat Eliason: Yeah, occasionally you’ll meet one, maybe.

Jimmy Soni: I think we’re also in a brave new world, though — you could see a universe where that’s okay.

Nat Eliason: Yeah.

Jimmy Soni: One question I have, among others — are you screening, how are you doing the screening and selection process? This is actively happening now. How do you admit a class of people you think are going to thrive in an environment like this?

Nat Eliason: Yeah, it’s something we had to put a lot of thought into, and are obviously going to keep refining. For this first class, we set the max at 20 — I think it’ll probably be 10 to 12, because we’re being very selective, and we wanted it to be a small enough initial cohort that we could be really hands-on with every student while we run this first year.

The first thing that surprises people is we don’t ask for a transcript, because it doesn’t matter that much what your grades were — basically every student who comes into Alpha, no matter what great school they went to, is anywhere from one to, gosh, five years behind on reading or math or these core subjects — not fully behind, but they have holes in their knowledge we need to fill in. So it doesn’t tell us that much. It gives us some idea of how gritty you are, but even for that it’s not a great measure. What we have is our challenge. There’s a first round of the application that just gets you in the door — short answers on why you want to do this, what you’ve done, entrepreneurship, hardest thing you’ve ever done. Then you get a challenge, where over two weeks you have to go through a baby version of the process I just described — come up with an unintuitive position on something, put together an MVP of how you’d do that, try to sell it to at least 20 people who aren’t your friends or related to you, then make a video and write-up on everything you did and learned, and send us the links so we can go look at it.

Now more people know this is the challenge, but for everybody in the process right now, they didn’t know this, so they didn’t have time to prepare for it. You learn a lot about a candidate with that two-week deadline. Some people just disappear at that point of the application — that tells us everything, it’s like, okay, this isn’t the right program for you. But other students blow us away. We had one student who was having a lot of trouble getting sales during the sales part of the process, and he ended up getting the D list for his entire school, and emailed everyone pitching his app to them. He got in trouble, got sent to the dean’s office. But he’s telling me this, and I’m like —

Jimmy Soni: And you’d like that’s amazing, that’s incredible.

Nat Eliason: Exactly, exactly. Those are the kinds of things we’re looking for — are you fully committed to this. In lieu of the transcript, we have what’s called the CCAT, a cognitive aptitude test. A lot of people don’t know this — Alpha makes every employee take this same test, and if you’re below the 85th percentile, you’re not eligible for any role at the company. So every single person at Alpha — the guides, the admin, everyone — has to be in the top 15% on this cognitive aptitude test. It’s incredibly reassuring for an education institution, knowing every single person interacting with your kids is at this level. We just used the same thing for the students, one because we were doing admissions kind of last-minute — we opened it in May for September — and I didn’t want to make them go do an SSAT. It’s only 15 minutes —

Jimmy Soni: Okay. Oh wow, a 15-minute test.

Nat Eliason: It’s a 15-minute test.

Jimmy Soni: Wow.

Nat Eliason: It’s quick, but it’s 50 questions — a mix of math, reading, spatial awareness, similar-ish to an IQ or workplace-competency test. We have them take that in lieu of transcripts or other standardized tests.

Jimmy Soni: Got it. We could talk about this for a couple more hours — I want to be respectful of your time. How do you treat summers? You’re enrolling kids into a four-year program, presumably, and a business doesn’t stop just because summer starts. How have you thought about that?

Nat Eliason: We’ll keep school hours during the summer for them to come in and work on campus, just without the academic portion. Austin actually keeps their school open all summer too — this was the students’ idea, because they loved going in and hanging out with their friends.

Jimmy Soni: More than vacation.

Nat Eliason: Exactly. Yeah, yeah. So we’ll do the same thing here — we encourage you to keep working on this over the summer, we’ll be here to provide all the same resources and support.

Oh, I didn’t even finish talking about what the rest of their day looks like — it’s that 70% working where they are in their business with us and the apps and tools, but then we’re going to have workshops each month on different themes — a month of leveling up everybody’s AI skills, a month of leveling up sales skills, a month of copywriting, some of these core business concepts. We’ll probably do two workshops a week, about one and a half to two hours, going deep on one skill for the month, with an adaptive structure so you’re not learning beginner material if you’re more advanced. But it creates more community time, interacting, working with each other instead of just working alone in your business, and it lets us help them develop skills they might not get as much exposure to until they need it.

The last part of the week, pretty much every week, we’ll either have an elite, top-tier entrepreneur, founder, or executive come in and speak to the students, especially about their early journey — how they got started, what they learned, doing lunch with a few of them, looking at their businesses, giving feedback — or it’ll be a roundtable discussion on a book. We’ll probably have them read The Founders.

Jimmy Soni: I was going to say, sign me up — because a lot of what I went deep on in that book was the high school years of the people I was writing about. Reid Hoffman, Elon Musk, Peter Thiel, Max Levchin, David Sacks — I’d start my discussions with them way before PayPal ever started. The first conversations were usually around high school and college, because you find that, in many cases, they were living their version of Founders School.

Nat Eliason: Right. Exactly, yeah.

Jimmy Soni: They cobbled it together, often at great personal risk, and in the face of a lot of parental pressure. There was one person — you’re telling a story that reminded me of a gentleman I interviewed who was, I think, the fifth or sixth employee at PayPal, on the engineering team. His name was Tom Pytel. He was this famously, this vagabond, with very dubious footwear — his shoes were ratty — but he was a genius-level coder. It was interesting, somewhat like — you’d admire people who dropped out of college, but he actually dropped out of high school. He decided he was just going to take the show on the road. He was writing code, I think, for video games, dropped out of high school, started working right then, continued that, found his way to PayPal, had no interest in being an employee, but the team kind of coaxed him into it — that was how he got his start. He was the ultimate example of what you’re talking about, without any of the support or structure.

Nat Eliason: I mean, again, going back to why we believe this is possible — people have been hacking versions of this together with way less support. Nobody really doubts that a Stanford sophomore could drop out and start what becomes a billion-dollar business. So what are they getting at Stanford? One, there’s the selection effects; two, some amount of network, from being there, meeting people who come to visit campus, maybe a couple of classes. But a lot of it is just, oh, okay, a 20-year-old can do this, a 19-year-old can do this — so a 16-year-old can definitely start a million-dollar business. It’s eminently reasonable. No one’s tried before.

Jimmy Soni: No one, I think, has sort of — I think one of the things Alpha School has made possible is you’ve just expanded the Overton window on what’s possible in education. A lot of it is you’ve asked the unreasonable question — what if this could be true — and then it becomes true as a result of asking, and then selecting the students, and building the programming. A lot of it, I think, is pushing the boundaries on what seems crazy but isn’t actually all that crazy.

Nat Eliason: No, I think people generally dramatically underestimate, especially teenagers.

Jimmy Soni: Yeah.

Nat Eliason: Because we’ve infantilized teenagers for a long time — you have to go to this place, follow this bell schedule, do what we tell you to do, and then you have to stay close to home, you don’t get to travel much in most places, we’ve gotten afraid of all these things. Then you go to college, and there you have to follow these rules too. So we think of a 14, 15, 16-year-old as less capable than they are. Obviously they’re still children, they still need support, encouragement, a certain amount of guardrails — but also, sometimes you just have to get out of their way and tell them, I believe in you, give them just the right little nudge to get started, and then they do these incredible things.

There was one student at Alpha High, when I was doing the OpenClaw workshop — I asked the group, “Where do you think you fall nationally on AI competence — top 10%, top 1%, top 20%?” The consensus was top 10%. This was toward the end of the OpenClaw workshop. I was like, no, guys, you don’t understand, you’re top 0.01% — people will pay a lot of money for you to help them implement this stuff. I could tell some of them didn’t believe me, some did. So I put it out there — I said, if you want to test me on this, I’ll intro you to somebody who’d probably pay you to help them with that. One student took me up on it, I introduced him to somebody trying to learn OpenClaw and AI stuff, and he made $250 for a two-hour call. He was to the moon — he’d never made money doing something like this before, and he was obsessed with the tech. It was like, oh my gosh, I can make money doing something I really like. We were debriefing afterward, and I said, awesome, super happy for you — next time, try charging four times as much. You could just see — he was like, seriously? That’s amazing. And then he did, and they were like, yeah, sure — they paid him a thousand bucks the next time. After that he just started getting referrals, his business kind of took off, and I did nothing after that. I think he made north of ten grand off doing this over the course of that spring. All I had to do was one little nudge, one intro, and then kind of get out of the way. It’s like, you just have to give them the opportunity.

Jimmy Soni: Yeah, I think what you made me reflect on is something you said at the very start of our conversation — the difference between being entrepreneurial and doing entrepreneurship. You had this line about being entrepreneurial in deciding you could make $250, or $150, an article, and use geographic arbitrage to go live somewhere that would let you actually live a life. That required an entrepreneurial frame of mind, even if it wasn’t big-E entrepreneurship in the conventional sense. As I think back to my own high school years, my first business was building custom-built computers for people. I was doing the other parts of a traditional academic life — getting the grades, went to Duke, did well on the SATs — but what I realized was that it was in building businesses and hacking things together that I actually used those same techniques to hack my education. Whether it was designing my own major, or — this is totally random, but I became obsessed with how you could hack the SAT. At one point I did a deep dive on all these obscure forums about ways people had hacked it. One of the things you discover is, at least in my stone-age era, when you had to fill it in by hand, circling the bubbles — if you put one black mark through the middle of the letter, it counts as that answer, instead of shading the circle. That seems like a small thing, except shading a circle takes three to four seconds, versus a single vertical line through the multiple-choice answer, which is one second. The difference between one and four seconds is three to four seconds — but multiply that across the entire test, and you’ve gained back minutes you can use to do the test faster, because the only reason the SAT is hard is the time pressure. Given infinite time, everybody could theoretically get a perfect score — but the time pressure is what matters. Once I figured that out, I’d just do the vertical-line thing, gain back two to four minutes per section, and that gave me all the time I needed to check answers or go back. But I don’t think I’d have had that ability if I hadn’t also been trying to hack things together on the side, whether on the Internet or in real life with computers. It seems to me what you’re giving these — I hate to say “kids,” students — is the gift of that entrepreneurial cast of mind, the same one that led you to say, I can do Thailand and $150 an article for Zapier and make it work.

Nat Eliason: Yeah. I think some people are certainly wired this way — I actually don’t know the answer of whether this is something that develops, or something you’re born with. Either way —

Jimmy Soni: We’ll find out.

Nat Eliason: I know, right? There are a lot of students who think and feel this way, and they feel like the world and the education system is against them, because they’re told they’re bad, or whatever, if they’re not following this set of rules. This is the one thing I didn’t expect, but it’s ended up being incredibly rewarding and meaningful even at this early stage — talking to some of these students and parents, and them saying, “We never thought there could be a school that said this is okay.”

Jimmy Soni: Wow.

Nat Eliason: That you’re — you’re a good kid, you fit in here, this is a space for you. That’s been really cool to see, because it’s like, I didn’t have that.

Jimmy Soni: Right.

Nat Eliason: And I think a lot of kids don’t have that.

Jimmy Soni: Yeah.

Nat Eliason: I think even just getting a lot of students like that in one room together is going to be pretty incredible.

Jimmy Soni: So excited. You uprooted your whole life for this — in some ways you made the same transition I did, where I never thought I’d have a job, and then decided to run a book publisher. What’s it been like transitioning from that — moving from Austin to New York, but also deciding, no, I’m going to be part of someone else’s ecosystem for a while, and develop and design this, but it’s bigger than me? This gets back to the question of commitment — how has that been for you?

Nat Eliason: It’s been great, actually. I’ve always been interested in this topic, education — one of the first entrepreneurial things I did after college was a podcast for kids who didn’t fit in the normal college-education system, trying to tell their stories and connect with them. I’d sort of assumed I’d never do anything in education — it never felt like something I actively wanted to go after, but I was always interested in it, and hopeful somebody would do something with it. So now, if I were going to say, “I want to make a school for entrepreneurs,” obviously it should be part of Alpha — it just makes so much sense.

To the extent I had reservations about joining a big company — it’s like a startup. I mean, the pace it moves at is incredible. We had 25 schools last year, we’re going to have at least 40 this year, and a lot more next year — growing like crazy. At Founders School, me and Cameron — it feels like we’re co-founders on a startup that, thankfully, is well-funded and has a lot of support around it. But we get to control our hiring pipeline, design our application process and curriculum — it has to fit the Alpha ethos, but we have a lot of freedom to be very entrepreneurial with it. We’re not clocking in, so to speak —

Jimmy Soni: It wouldn’t work if you were.

Nat Eliason: Exactly. So all the things I was afraid of about taking a job — job, yeah — just haven’t materialized. Instead it’s been incredibly fun. Going back to the thing I was talking about at the very beginning, wanting to work on something big and long-term, really fully commit to something — I thought that had to be something 100% my own. But maybe that was also, at least for this phase of life, the thing that was holding me back in some sense — because I’m learning so much from being in a bigger organization like this, from not having some of the immediate profitability pressure I would have had on my own, from getting to work with Joe and see how he thinks about business and learn from him. It made me realize it was actually a big limiting belief for me, that I have to always work for myself, that I have to do this alone. I’m super glad I’m doing this, because the interest has been incredible, and seeing these students applying — it’s so much fun, I’m having a great time with it.

Jimmy Soni: Yeah. I wanted to talk to you about many other things, but this conversation has been utterly riveting, and I think we ought to try to have your students on Infinite Loops in the year ahead — as they’re going through the process, I think it’d be a lot of fun to see what they’re building, how they’re building it, how the school is maturing and evolving, and I hope we can do that.

As you know, having been a repeat guest, we ask a question at the end of every episode. You get the ability to incept an idea into everybody’s mind — two thoughts, whatever they are, you can’t use it for violence, you can’t overthrow governments — I mean, unless —

Nat Eliason: Yeah, I think we could actually sanction that one.

Jimmy Soni: You basically get to be emperor for a day, and everybody wakes up the next morning with these two ideas in their head. It’s an interesting question for you as a guest, because you’re actually molding young minds — what are, off the top of your head, the two ideas you’d incept in everyone’s mind? Or two thoughts, quotes, anything.

Nat Eliason: It’s naturally going to be topical, because this is what I keep thinking about, so much of this is based on it. The first one — what I said earlier, that we take teenagers seriously. I talked about this with Chris Powers when I was on his podcast a couple of months ago. But the more I’ve thought about this and explored the idea, the more it does feel like there might be way more problems than we expect that stem from expanding childhood as far as we have. If you go way back, you actually find versions of something like Founders School in Maria Montessori’s writing — she talked about how the childhood school is this core-life-skills stage, the cleaning and cooking and things everybody should know how to do to operate as an adult, the manners and whatnot. But she never got to fully realize this, because of challenges with how society was changing at the time and her resources — her vision of later-stage education was this Erdkinder, where you were doing a bit of academics but also working on a farm or in some kind of apprenticeship, getting hands-on skills, because she didn’t think teenagers should be stuck in a classroom.

You look at basically every pre-modern society, and there are these significant moments where you transition into adulthood, around age 14 — you think about a bat mitzvah, a bar mitzvah, that’s around that age, a confirmation is around that age. You visit tribes in Kenya, the Maasai Mara, and guess when you become a contributing member of the tribe — it’s around that 14 age.

Jimmy Soni: Right.

Nat Eliason: I actually think a lot of the things we assume are bad about childhood — kids hating school — and some of what we assume is bad about having teenagers, might be because they’re capable of doing more adult things, being more adult, but then heavily constrained by their environment. So they naturally lash out against the things doing the constraining — school, parents, society. Alpha’s done a good job of asking, what if we took students, especially teenagers, seriously and gave them this freedom? And now we’re taking it to the extreme — what if we trusted you as much as a 30-year-old, to run a business? I feel there’s a lot of unexplored opportunity there. And — these are different things, to be really clear — but people getting married much later, starting families much later, the aging population — I think we’ve extended childhood further than we should. It can sound dangerous to say that, because you don’t want to force kids to grow up too fast — I’m not advocating for that either — but I am advocating that if somebody shows the ability to be treated like an adult, to be taken seriously, we should figure out how to take them seriously. I’m excited to see where that goes.

Jimmy Soni: Yeah. Actually, when I was prepping for this, I was looking back at some of what Maria Montessori was writing and thinking about — I think of her as far — even though the brand Montessori is as well-known as it is, a lot of her ideas, and her as a person, are vastly underrated compared to others. She’s so cool. One of my favorite stories: she was one of the first women admitted to medical school in Italy, and they wanted to wash her out — they made her dissect cadavers alone, where the male students all got to be with each other. She had to do that on her own, because they thought it would scare her off medical school — and it did the exact opposite. She was burned in effigy in different countries, because people thought her ideas were too heretical. Now everybody and their brother pays gobs of money to get their kids into Montessori or Montessori-type environments, and a lot of her ideas are being validated by science in 2026, in a way they weren’t even 50, 75 years ago. So I take what you said very seriously, because there are echoes in what you’re trying to do and what she was trying to do.

Nat Eliason: Yeah. There’s this book that got really popular a few years ago, called Hunt, Gather, Parent, that talks about tangential, similar ideas — the most enduring idea from that book, the one you hear parents recite most often, is that how you treat a child who wants to help at an early age decides how much they contribute and feel autonomy and agency throughout a lot of the rest of their life. One of the main things the book advocates, basically the same thing Montessori says, is that if a kid thinks they can do it, you just let them do it. Doesn’t matter if they’re going to break the egg, take four times longer, or fall off the ladder, assuming it’s a reasonable height — you let them do it. The argument was, if you tell a kid, “No, you can’t help me wash the dishes” when they’re offering, they’ll just learn that, and then suddenly they’re a 12-year-old who won’t help when you ask, because they’ve internalized it that way. She was going to a lot of more traditional cultures in that book, and that was one of the big differences she noticed — they were letting kids do stuff they were bad at, that was actually slowing things down, obstructing progress, because they’d internalized the lesson that if you just let them, they’ll eventually figure out how to be very helpful, and those rewards come later.

Jimmy Soni: Exactly.

Nat Eliason: It’s such a fascinating idea that I feel has been lost. But going back to raising kids in the city — it feels like we get some of that here, because my kids are riding scooters through the streets now, through the sidewalks at least. The other day, we were at a coffee shop, and my wife had taken the youngest one home, which was around the corner — a block away. My two older girls, they’re four and three, said, “Can we go see Mommy?” I was still in the coffee shop, and I said, sure, go ahead. They scooted down the block, did the turn, went to the house. I called Cosette and said, hey, by the way, make sure they actually show up, please. She texted me a picture a minute later of them at the door, and I said, awesome. You got that little opportunity for autonomy and independence that, sadly, I think some people probably wouldn’t even let their 9- or 10-year-old have.

Jimmy Soni: And in areas where commuting and everything happens by car, it’s a lot harder —

Nat Eliason: It’s a lot harder.

Jimmy Soni: Can’t get away with it in the same way.

Nat Eliason: Yeah.

Jimmy Soni: What’s your second idea you’d incept everybody with? Your first one was a real banger.

Nat Eliason: Oh, geez. Gosh. Yeah, the second one — that’s a lot of pressure. I’m trying to find the right phrasing, because what we were talking about earlier, doing things that are entrepreneurial even if they aren’t big-E entrepreneurship — that really is agency. I think that’s downstream of this idea that the world is a lot more malleable than you tend to assume. This was another big red-pill moment for me as a kid — I don’t remember exactly when, but there was some point when I realized there wasn’t really such a thing as rules. There’s the way other people want you to do things, the way you should do things to be a good member of society, and then there are things you’re told to do, or should do, or how it’s done, that if you don’t do it, there’s literally no consequence, or a very acceptable consequence, or everybody’s kind of doing it because everybody else is. So whenever you encounter something — could be work, personal life, society, whatever — of how something works, or what you’re supposed to do, it’s literally a suggestion. It’s an idea.

Jimmy Soni: Outside of very few things.

Nat Eliason: Exactly, yeah. And, I mean, that mindset can obviously go in bad directions, but — we had a couple of fifth graders at Alpha who were super into robotics, really sharp, and they came up with this idea for a robotics-security-related startup, and they emailed the FBI to pitch them on it.

Jimmy Soni: Wow.

Nat Eliason: It was fine — nothing bad happened, obviously. But if you asked anybody, “Hey, can you just email the FBI your startup pitch?” they’d say, no, you can’t do that.

Jimmy Soni: Right.

Nat Eliason: But you can. As a ten-year-old.

Jimmy Soni: Exactly.

Nat Eliason: To be clear, it’s not something I’d encourage our students to do, but there’s something really admirable about it too. That’s going to take them far.

Jimmy Soni: Yeah.

Nat Eliason: I think it’s so easy to get frustrated by things not being the way you want, or feeling trapped, like you don’t have options — but you pretty much always have way more than you think you do. You just have to be willing to look for them.

Jimmy Soni: And reality is malleable.

Nat Eliason: Reality is malleable. There you go.

Jimmy Soni: Well, Nat, thank you. We’re going to have you and your students on over the next few years, see how this progresses and continues to develop — I’m personally very excited about it. I’m excited for you, as a friend — I want to see how this affects your life, and I can’t wait to have further conversations about it too.

Nat Eliason: I’m super excited too. And, serious offer — we’re doing these book-club things with the students —

Jimmy Soni: It’s a given.

Nat Eliason: Eric’s going to come do one for The Book of Elon — you should come do one for The Founders.

Jimmy Soni: It’s a hop across the river.

Nat Eliason: Exactly. That’d be super easy, a lot of fun.

Jimmy Soni: Amazing.

Nat Eliason: All right.

Jimmy Soni: Thank you.

Nat Eliason: Talk soon.

Leave a comment

Subscribe now

Share

We discuss why government has become unmanageable, how thousand-page rulebooks discourage individual judgment, why infrastructure projects can take decades to approve, and how public institutions end up costing more while delivering less.

We’ve shared some highlights below, together with links & a full transcript. If you like what you hear/read, please leave a comment or drop us a review on your provider of choice.

Links

Apple Podcasts

Highlights

The Department of Silly Walks is in Charge

Philip Howard
But the reality is, the situation has gotten worse.

Jim O’Shaughnessy
And diagnose it for me — why? I mean, I have pretty strong views on this. I think our current political class is one of the worst, on both sides of the aisle. I’m very bipartisan in my view. But why?

Philip Howard
What no reformer has done yet is take on the underlying operating philosophy of modern government, which is basically that we should replace human judgment with either specific legal rules or objective proof. There was no such thing, until the 1970s, as thousand-page rule books. There was no such thing as having to go to a months-long hearing to prove that somebody doesn’t do their job. The Interstate Highway Act, which was in 1956, was 29 pages long. Within 10 years, over 20,000 miles of road had been built. The last transportation bill was almost 1,000 pages long, and it would take 10 years to get a permit for one stretch of road.

Jim O’Shaughnessy
It’s almost like Monty Python is running the government — the Department of Silly Walks and all that. But again, I’m going to press you: why?

Philip Howard
Well, a lot of people make money on this system. When I went to law school, which was a long time ago, the new orthodoxy was that you can’t trust human judgment. An official might be like Robert Moses and blow through—

Jim O’Shaughnessy
I was going to bring him up.

Philip Howard
Right. And so we were going to create a government better than people. And we have. Take the worker safety rules — there are 4,000 of them. I’m all for worker safety regulation, but the way they do it is they have 4,000 rules, and rules that say things like “stairwells shall be lit by natural or artificial light.” Now, that’s useful. Then the company has to have a compliance inspector who has a checklist for these 4,000 rules, going around checking the boxes that they do this. That’s a person doing really nothing useful. Then there’s another person who checks the checker. So you have all this bureaucracy building up, and Washington becomes this enormous factory for red tape.

And law firms — including the law firm I was a senior partner of — you have these law firms doing really well, making money, and lobbyists, and they all navigate the precise language and they argue over it, and really nothing ever changes. It’s like a perpetual tug of war, and they have no interest in changing it. Everybody’s doing well. I think Washington has one of the largest Lamborghini dealers in the United States — a place where nothing ever happens.

The Freedom to Take Reasonable Risk

Jim O’Shaughnessy
I grew up in the 1970s. We were free-range kids. We could do whatever we wanted, as long as we got home.

Philip Howard
Right. And so what’s happened is... A couple of decades ago there was a terrible accident on a sledding hill in Greenwich, Connecticut.

Jim O’Shaughnessy
I remember it well.

Philip Howard
And someone got a verdict of $6 million. And the result of that was not... I mean, Greenwich is a rich town, it could afford it. The result was that sledding hills across the country closed down.

Jim O’Shaughnessy
Yeah. Including that one.

Philip Howard
Right, including that one.

Jim O’Shaughnessy
I used to take my kids there.

Philip Howard
Right. So all of a sudden, because of a lawsuit brought by one person — no deliberate policy choice — the trade-off judgment about whether the risks of sledding outweighed the fun of going out in the winter and the snow was not being made by anybody who’s politically accountable. It was being made by the fact that somebody brought a lawsuit. And there was a similar case in England around the same time, where somebody — terrible accident — dove in a lake and became a quadriplegic. Terrible accident. But there were no hidden dangers there. Sure, you could run into something if you weren’t watching, but people had sledded on that hill for decades—

Jim O’Shaughnessy
It was a rite of passage for your kids.

Philip Howard
Yeah. And so in England, there was nothing hidden — it was just a freak accident. It was tragic. But the county that owned the lake was so scared of liability, because there were two or three near-drownings a year — a big lake, people swimming, bad things could happen — that they had determined to close the lake down. And then this accident happened. So the court said, “Well, this is foreseeable, therefore we’re going to grant damages to this person.” It goes up to the equivalent of the UK Supreme Court, and they order the case to be dismissed. They say, “It is part of our role” — as the lead judge put it — “to protect the reasonable freedoms of people in society, including the freedom to take risk. Do we require that rivers and lakes close down because of the certainty that some accident will happen? Do we require all trees be cut down because some child may climb one and fall? We will not tolerate a dull and gray safety regime. We are here to protect the reasonable freedoms, including the freedom to take reasonable risk.”

Jim O’Shaughnessy
What a great decision.

Philip Howard
And it’s called the Tomlinson case. And that’s what we’re missing in this country: no one is drawing those boundaries.

Transcript

Jim O’Shaughnessy
Philip Howard. Finally. We’ve known each other forever — I served on your board at Common Good. I discovered you well before I met you, with your first book, The Death of Common Sense, in 1995. Loved it. have loved all of your books. But I’ve got to ask — that’s 30 years ago, 31 years ago, and things have seemingly only gotten worse.

Philip Howard
Right. I had lunch with a tycoon a few years ago, and he said, “I like what you write, but have you ever accomplished anything?” And I said, “Well, actually, now that you mention it, I have a perfect record of failure.” He said, “That’s what I thought. I’m not giving you any money.” That’s not exactly true — I actually have worked on a bunch of reforms with Congress. But the reality is, the situation has gotten worse.

Jim O’Shaughnessy
And diagnose it for me — why? I mean, I have pretty strong views on this. I think our current political class is one of the worst, on both sides of the aisle. I’m very bipartisan in my view. But why?

Philip Howard
What no reformer has done yet is take on the underlying operating philosophy of modern government, which is basically that we should replace human judgment with either specific legal rules or objective proof. There was no such thing, until the 1970s, as thousand-page rule books. There was no such thing as having to go to a months-long hearing to prove that somebody doesn’t do their job. The Interstate Highway Act, which was in 1956, was 29 pages long. Within 10 years, over 20,000 miles of road had been built. The last transportation bill was almost 1,000 pages long, and it would take 10 years to get a permit for one stretch of road.

Jim O’Shaughnessy
It’s almost like Monty Python is running the government — the Department of Silly Walks and all that. But again, I’m going to press you: why?

Philip Howard
Well, a lot of people make money on this system. When I went to law school, which was a long time ago, the new orthodoxy was that you can’t trust human judgment. An official might be like Robert Moses and blow through—

Jim O’Shaughnessy
I was going to bring him up.

Philip Howard
Right. And so we were going to create a government better than people. And we have. Take the worker safety rules — there are 4,000 of them. I’m all for worker safety regulation, but the way they do it is they have 4,000 rules, and rules that say things like “stairwells shall be lit by natural or artificial light.” Now, that’s useful. Then the company has to have a compliance inspector who has a checklist for these 4,000 rules, going around checking the boxes that they do this. That’s a person doing really nothing useful. Then there’s another person who checks the checker. So you have all this bureaucracy building up, and Washington becomes this enormous factory for red tape.

And law firms — including the law firm I was a senior partner of — you have these law firms doing really well, making money, and lobbyists, and they all navigate the precise language and they argue over it, and really nothing ever changes. It’s like a perpetual tug of war, and they have no interest in changing it. Everybody’s doing well. I think Washington has one of the largest Lamborghini dealers in the United States — a place where nothing ever happens.

Jim O’Shaughnessy
Yeah, I was just down there and saw as many fancy cars as one might see in Greenwich, Connecticut. And it seems to me that the source might have been the idealism of the 1960s. And by that I mean: we can make things better. But I think it counted also on this idea that we are born as a tabula rasa — as a blank slate. And we are not born as a blank slate.

Philip Howard
Right. Well, first of all, we are not born as a blank slate. And I think there was some idealism. There was a kind of naïveté that, with modern technology on the rise — and that was the era of IBM 360s, stuff like that — they could do it. But the real driver was guilt. We woke up in the 1960s to segregation, to pollution, to unsafe cars, to locking up disabled children in horrible places.

Jim O’Shaughnessy
We were doing some horrible shit.

Philip Howard
Yeah. And so the establishment had a record of neglect of many groups that should not have been neglected. It was one thing to change the values, which we did do — with environmental laws and civil rights laws, and all that was good and necessary — but they wanted to make sure that they could never happen again. And the way to make sure there were no abuses of authority was to get rid of authority. And so—

Jim O’Shaughnessy
Excuse me — get rid of individual’s authority.

Philip Howard
Individual’s authority.

Jim O’Shaughnessy
The regulation was going to become the authority.

Philip Howard
You’d have a legal system that would tell everybody what to do. Eric Foner is a very distinguished historian from Columbia University. He wrote a book they call The Future of Freedom, where he said that in the 1960s the governing idea was the elimination of all authority — so freedom would be enhanced if no one had authority. Now, it turns out that’s upside down. If the person running a firm, let’s say, doesn’t have the authority to uphold mutual standards and values, then there isn’t going to be mutual trust, and in fact everyone loses their freedom. There’s nobody to go to and say, “I’ve got a good idea, let’s change the way we do things.” Authority is actually critical to everyone’s freedom. You need red lights and green lights in any society and any institution.

But we’re still trapped in this kind of quicksand of law that we created, where no one can make a judgment. And then the result is that people who don’t respect law — like the current president, for example — can get away with murder, because they just simply ignore it.

Jim O’Shaughnessy
And one of the things that I always come back to — you mentioned all of the abuses that were being solved. I was 100% in favor of everything you just mentioned: the Civil Rights Act, the Clean Water Act. The rivers around this city used to be so polluted that you risked your life jumping into them. And they got a lot cleaner. So all of those initial rules and regulations and new laws, I think, actually did really good things. And then what you’re talking about started to happen, and we became a society... I had a guest on who was basically comparing the US and China, and he goes, “The US has developed a lawyer society. China has developed an engineer society.”

Philip Howard
Right. Dan Wang.

Jim O’Shaughnessy
Yeah. And when I was on the board of Common Good, all of the ideas you came up with, and the other board members and associates — I thought they were brilliant. But how do you get that into people? Because I’m not a Democrat or a Republican. Maybe I’m kind of like you: a radical centrist.

Philip Howard
Yeah. Well, again, I’ve been working on specific reforms. I was very involved in a bunch of environmental permitting reforms in Congress a few years ago. We developed this project, you’ll remember, for expert health courts, and got everybody for it. Obama agreed to support it — for medical malpractice, it’d go to an expert court without juries, and it would make health care better and also relief quicker for people who were really injured by mistakes. We had a pilot project in the Affordable Care Act that Obama supported, and funding for it. And the day before the vote, the Democratic leader of the Senate, Harry Reid, had it pulled. Because the trial lawyers — they make all their money on extortion. “You may be liable for $20 million for this tragedy, therefore you’d better pay us 10,” or something. Even though the doctor may have done nothing wrong — it may just have been a sick person getting sicker.

So it’s been hard to make change. But one does feel that times are changing. Politics have become more extreme on both sides.

Jim O’Shaughnessy
Yep.

Philip Howard
The left is more left, and the—

Jim O’Shaughnessy
Yeah, we were just talking about it before you got here. It’s like, wow — when did this happen?

Philip Howard
Yeah. And the right is... So there’s clearly more of a mood for change. Two-thirds of the country is dissatisfied with both parties, don’t like the way things are. Also, close to two-thirds of the country fundamentally agree on basic values — the golden rule, honesty, all that kind of stuff. It’s not like diversity has driven us apart. People still believe in the same things.

It does seem there needs... I’m talking to some former attorneys general now. I just hosted a three-day workshop three weeks ago to try to come up with a new political narrative. The idea is not to start a new party — not even, at least for now, to start a movement — but just to change the conversation. So we’ve come up with an idea for a new narrative. It’s in writing. We’re in the process of trying to get some leading citizens to sign on to it. I was just talking to former governor Mitch Daniels yesterday about it, so he’s on board — and getting a group of people to start talking about it.

This new narrative is not about policy, it’s about how things work: how you run a school, how you get a permit, how you’re allowed to act honestly with each other in the workplace without fearing a lawsuit — that sort of thing. It’s really about operating systems. So we have a name for it, we have a narrative that we’re working out, and I think it’s good. It took a lot — I had a bunch of marketing people and press people in this workshop.

And so we’re going to try to roll it out slowly, with just leading citizens — maybe yourself — talking about it with different groups of people, and begin to say, “Isn’t it time that we actually overhauled the system so that people can act, so that Americans can roll up their sleeves and act like Americans?” That’s what people no longer feel comfortable doing, and the law is what’s gotten in the way. It’s just legal quicksand. So it’s about re-empowering human agency.

Jim O’Shaughnessy
Yeah, which is something I deeply believe in. And also, when you look at the history of this country, you have things like... You have a book on this — I think it was probably your most controversial — and that was public unions.

Philip Howard
Right. Not Accountable.

Jim O’Shaughnessy
Right. Not Accountable. Great book. And as I was reading that book, I remembered that FDR himself said that would be the worst thing to ever let happen. Many people consider FDR one of our most progressive presidents, and yet he was like, absolutely not. And yet it happened.

Philip Howard
Right. Well, it’s funny you mention that. I’m just finishing a book called Burning Money, and it’s a book that tries to describe the harm of government that’s become unmanageable. It’s very hard proving a negative. But I teach at Harvard Business School sometimes, so I have a lot of business school professor friends, and they sort of help me out. It’s funny — there’s a vast library of books on how to manage businesses better. There is not one book on what happens if you lack managerial authority. It’s just like breathing — it’s like what happens if you don’t breathe. If you don’t have somebody who can actually direct resources here or there, decide who’s good at what, adapt when something unforeseen happens — all the things that have to make anything work in any institution require managers. Well, guess what? Government no longer has managerial authority.

So, more or less — particularly in the big cities and big states, New York, Illinois, New York City — we’re getting about half the product at twice the price, and we can’t afford that anymore. There are a lot of public needs, and there are a lot of serious policy issues that need to get addressed — income inequality, all kinds of stuff. Meanwhile, we’re burning money. We’re literally burning money. There’s a school in Chicago that has capacity for 1,000 students that has 27 students in it, and no one has the capacity to close down the school and transfer the students to a nearby school, because the teachers’ unions have made it so that no one can close a school. Half of New York City schools are operating at barely over half capacity because of declining demographics. But the teachers’ unions got a law — called maintenance-of-effort laws — which requires that a district never reduce its budget unless tax revenues go down. Because the teachers’ union got an agreement.

So for 50 years, since they got collective bargaining power, year after year, they’ve gotten more and more requirements like that built into the codes. These are laws now — laws that literally require us to burn money. Almost no one appreciates that. I’ve hired lawyers. I have a partnership with the public interest law firm in Chicago that just won the tariff case against Trump, and also won the Janus case. So we have a draft complaint in federal court to challenge the constitutionality of public union controls, ready to go. But I don’t want to do it until I write this book that explains why it’s so harmful that we can’t manage government.

Jim O’Shaughnessy
And you mentioned earlier that what we really need is a new operating system. And in operating systems, incentives kind of rule everything around us. Right now, as you’ve just outlined, our incentives... For example, if I were the head of the public teachers’ union, man, I would be calling for more of those laws, because I’d be highly incentivized to do so. And so it’s easy and disingenuous, in my opinion — it’s easy to scapegoat everybody. Let’s just stop doing that. Let’s look at the underlying system and the incentives that result from it. That explains a ton. I remember one time you told me about the law here in New York City where a public school teacher may not — if a child is in distress, remember this? — the teacher may not touch the child. In other words, one of the most basic human instincts, if an adult sees a child in distress, is to comfort them. That’s just so part of the human OS.

Philip Howard
Right. But we have this precautionary system of government, of law, now, so that anything that might go wrong is forbidden. So, it is possible a weird person could touch a child inappropriately.

Jim O’Shaughnessy
Yeah, of course.

Philip Howard
Because that is possible, and not that unusual — you know, Catholic churches and priests and all that — so they make a rule that you can’t touch a child. But that’s equally weird. And so the only way to square the circle is to have a system where the people in charge are allowed to use their judgment about who’s a good person, who maybe is a little odd, and be able to remove the odd person from that teaching job. But you can’t remove anybody. I interviewed a former commissioner in New York recently who said that in his 40 years of being a top official in New York City, he had never seen anyone terminated for performance.

Jim O’Shaughnessy
Wow.

Philip Howard
Never. So you have a system where you can’t terminate the weird person just because you say they’re a little weird — you have to prove they’re weird. Well, how do you prove someone’s weird? Most of the things that are... I think it was Einstein, or someone like that, who said if it can be measured, it’s not that important.

Jim O’Shaughnessy
In investing: once a target becomes a measurement, it’s no longer useful as a target.

Philip Howard
So we have this system that assumes that right and wrong can be proved objectively. That is manifestly false. How do you prove someone is selfish? How do you prove somebody has good judgment at this but not such good judgment at that? How do you prove who works hard, who cooperates well? How do you prove what’s a good product, what’s not a good product? None of this stuff is provable. It’s tested in the marketplace of human relations, in the marketplace of values, in the marketplace of products — but it’s not provable. This system is built on a false premise, and we need to basically go back to a human system.

The Constitution, with all amendments, is 7,500 words. It includes principles like no unreasonable searches and seizures, and freedom of speech. It does those things in a couple of words. It doesn’t define them, but they become defined over time as issues come up. People have a general sense, from those principles, of what the boundaries are. And we feel comfortable going to bed at night that the police can’t just arbitrarily barge in and throw us in jail or whatever. The current system of federal law and regulation is 150 million words. It is beyond the capacity of any human understanding. And even AI can’t make sense of it, because it’s not consistent — it’s like a giant short circuit of all these laws piled on top of each other.

Going back to the teachers’ union: a couple of years ago, the Citizens Budget Commission in New York City counted 21 bills that passed the legislature to enhance union benefits and rights in one year — 60 years after they got collective bargaining power. Now, not all of them ended up making it into law, for one reason or another, but they are relentless. And so you pile up all this stuff, year after year, and after a while, government’s unmanageable. It doesn’t deliver. It wastes money. By the way — you’re a money guy, right? 23 million people in the United States work for the government. 23 million people. That’s over one in seven people in the workplace. They are not manageable. They’re not managed sensibly in any way. They cost about $3 trillion — in total comp and benefits. And they spend, in a discretionary way, or oversee, another four to five trillion dollars. So we’re talking about not quite, maybe, a third of the GDP being spent by a system that is no longer manageable — and it’s not delivering public services very well, either. And there are all these new needs. So why do we tolerate that? We tolerate it because we don’t understand it.

Jim O’Shaughnessy
It seems to me — I always argued... I’m a big fan of philosophy, and you don’t need to be a pure Platonist or Aristotelian, you need both. Because if it’s pure Plato, you get the Republic, and you get the philosopher kings, and, oh, they’re going to do a great job. What you need from Aristotle is: wait a sec, that might not work out like that.

Philip Howard
Right. The happy mean, right?

Jim O’Shaughnessy
Yeah. And what I was always struck by in our many conversations is, I just can’t believe... We know that the majority of Americans intuitively understand this. We know, as you mentioned earlier, that if you looked at Americans of all races, creeds, colors, sexes, et cetera, we share much more in common than divides us. And yet here we are.

Philip Howard
Right. So we need a new... And by the way, neither political party will solve this problem. If you project out five or 10 years, there’s nothing on the horizon that is even conceivable that could end up solving this problem. The Democrats get most of their resources from the worst of these groups. By the way, I happen to be a registered Democrat. I’m for environmental protection, I’m worried about climate change, I’m for taking care of people who need help — I’m for all those things. They will never solve this problem. And the Republicans see government as the enemy. Both parties do just fine running against the extremes of the other party.

Jim O’Shaughnessy
Right.

Philip Howard
They collect a lot of money. The Democrats collect it from the people who can’t stand Trump, and the Trump people collect it from the people who can’t stand AOC and Mamdani. So you have this system where both parties are profiting by extremism and leaving the vast middle, as you described, behind. We have to come up with a new narrative first — a new narrative and a vision — and then let it turn into something.

I was talking to a former attorney general — I won’t mention him, because I don’t have permission, but a very prominent attorney general. We were having a discussion. I didn’t know him; he was introduced to me by the president of an insurance company. I said, “Well, do you know why we’re talking?” He said, it was on Zoom, “No, I have no idea why we’re talking.” So I said, “I don’t think either party’s going to solve the problems of this country. We need a new narrative that actually addresses the problems people see with a government that doesn’t function very well and doesn’t let people be themselves. We go to video trainings that tell us, basically, don’t be yourself, don’t tell a joke, don’t be candid.” So after about six or seven minutes, he starts finishing my sentences. And then, at the end of our half hour, he says, “Okay, here’s what we do. You come up with the framework of principles about what this new vision looks like, and we’ll go find 8 or 10 or 12 really prominent citizens to start talking about — we don’t have to agree on everything — start talking about why this is directionally what’s missing in our public discussion. And then we start... maybe we have some public events, then we start talking about it.” And he said, “I think it’s possible that we could get one or more people running for president in 2028 to talk this way. Because everybody, just listening to you — of course you’re right. This is exactly what’s... Of course you’re right. Everybody knows you’re right. Just nobody’s saying it.”

Jim O’Shaughnessy
And that’s the exact point that always frustrates me. There’s that great quote — I can’t remember who said it — but it’s like, “If you give me the ability to write the stories of a country, I care not who writes the laws.” And he was really onto something there. That’s why I’m really happy to hear that you’re developing the narrative. Because the system we operate under right now assigns you the bin you’re going to be in. If you can attribute all of my political or social positions from hearing one of them, I am brain dead. I am flatline. And yet that’s what they do, right?

Philip Howard
Yeah. The thing people don’t appreciate with this modern mutation of law is that law is not supposed to be central planning. Law is supposed to be a framework that protects people from bad things — no pollution, no discrimination, no cheating, whatever. Within that, it’s supposed to safeguard an open field of freedom.

Jim O’Shaughnessy
Yes.

Philip Howard
So what’s happened in the last 60 years is that the open field of freedom has become a legal minefield. Instead of proscribing what was bad, for 60 years or so since the ‘60s, we started prescribing how to do everything — and also giving anybody who doesn’t like your decision-making a legal right to challenge it.

I wrote something for The Free Press recently. I had a series on great Americans who are not political leaders, leading up to July 4th. I did one on an early management theorist named Mary Parker Follett, who died in 1933. She was a prominent management theorist before women could vote, so she was really a rather unusual character. One of her points was that as modern democracy is evolving, we have freedom all wrong. It’s important to have democratic elections, but democracy is all about just going in one direction or another — it’s about the herd, it doesn’t affect your freedom. And then there are other people — John Stuart Mill and others — who talk about the importance of individual rights: you can do whatever you want to do. She said, talking about the individual, that it’s like breaking a branch off a tree and expecting it to live. We don’t live alone, individually; we live in groups. And it’s within groups that people innovate and find meaning and fellow feeling, and develop their values and apply their values. It’s in group activities.

And one of the things I think she could not have foreseen was that this modern, post-’60s idea of law — that tells you exactly how to do everything — means that people really are no longer free, that groups no longer have the capacity to innovate and do things their own way. People running a school can’t run it: “Let’s try this.” Can I tell a regulatory success story? A couple of decades ago, Australia had terrible nursing homes. America, by the way, is terrible — do not go to a nursing home. And they’re regulated by thousand-page rule books that tell you when the meals are and how much they have to weigh and how many ounces of vegetables, and all this kind of stuff — just crazy. But they were terrible nursing homes. So someone had the bright idea of scrapping the rule book and replacing it with what ended up being 31 general principles: have a home-like setting, respect the dignity of the residents, that sort of thing. So they did it. And all the legal scholars had scoffed — “these nursing home operators are going to get away with murder; if you don’t tell them exactly what to do, they’ll abuse the residents.” They went a year later to look at how it was going, and what the scholars found is that the nursing homes were twice as good. They looked into why. One reason is that now the nurses’ aides came to work, instead of with a checklist of a thousand things to check off, having internalized these principles. They looked at what the residents wanted. Instead of telling nursing home owners exactly how to do things, they let them do it themselves. One nursing home has a gardening theme, another one has a different theme — they have completely different themes. They can innovate, they can do it in their own way, and take pride in the uniqueness of their creation. Humans need agency. We need to be able to make a difference. This vast legal system has snuffed it out. No wonder everybody’s going crazy and voting for extremists on both sides — because we’re not allowed to be ourselves.

Jim O’Shaughnessy
Particularly for this country. There’s a book called The Hypomanic Edge — Why America has a Little Craziness But a Lot of Success. The thesis is: well, look at who made up the population of this country. They had to be willing to say goodbye to everything they knew — their families, their friends — often with no money in their pockets, and come over here. And so what do you get? You get that type of person.

Philip Howard
And you get people who have to invent. In the old country, you were born the way you were — and that still, to a certain extent, affects the cultures of the old countries.

Jim O’Shaughnessy
Yeah, I agree.

Philip Howard
You’re the son of a carpenter, you became a carpenter. In this country, you move over to the wilderness, the frontier, and if you don’t watch out, somebody’s going to come scalp you. So you really have to take care of yourself.

Jim O’Shaughnessy
Yep.

Philip Howard
And people just invent. Americans invented themselves. Modern — Elon Musk, or Thomas Edison. Thomas Edison’s so smart about this. Here’s a guy with a third-grade education. Great lines. “Nothing any good works by itself. You’ve got to make the damn thing work.” So you imagine him developing sound, inventing the electric light bulb, and all that kind of stuff — but by tinkering.

There was a great book by Harry Evans — God bless him — who was the former head of the Times of London and then became the head of Random House. He bought The Death of Common Sense when it came out; he ran Random House, which published The Death of Common Sense. Oh, it was so much fun. The first time I met him, I was so scared, because I’d never written a book before, and here’s the editor-in-chief of Random House. And he’d say, “I’m so excited about your project. It reminds me of this and that.” He’s completely into it. And years later — we stayed friends — he wrote a book, a coffee table book, which I really urge people to read. It’s called They Made America. It’s a coffee table book of 5,000- to 10,000-word essays about Americans who innovated one way or another, and what their character was and who they were.

So, the Wright brothers. Everyone knew, with the internal combustion engine and all that kind of stuff, and the idea of wings and stuff, that it would be possible to achieve manned flight. And you had the leading physicists in the world, all over the world, trying for some big prize for who could first achieve manned flight. Literally the smartest people in the world, the most educated — they’re all doing experiments and having these things take off on the Potomac and become submarines immediately, that sort of stuff. And then you have these two bicycle mechanics in Dayton, Ohio, who start pedaling around with little foils to test wind flows on their handlebars to see how they work, stuff like that. It’s like Edison, just tinkering. And these two boys, the bicycle mechanics, do it. And after they do it, no one believes them. No one believes them. So they go to Paris. Nobody believes them — this is five years having gone by since Kitty Hawk. They go to Paris, people still don’t believe them. And everyone fills the big stadium, and the French papers are completely making fun of them. It’s some French phrase — the American bluff, or something. And so their little plane takes off from the infield of this racetrack — it’s like Bourget, I think, Le Bourget — and they take off, and people kind of gasp. And then it starts coming toward the grandstands, and people start to panic — this thing’s going... And then it turns, and people just could not believe it. It is such a great story.

Anyway, Harry has his Goodyear in there — sitting there making his family sick by vulcanizing rubber in his kitchen, stuff like that. So these are all basically predecessors to Jim O’Shaughnessy. All these people in the book, making their family sick by bossing them around and making them do all this stuff. It’s a great book, They Made America. It’s about the American... it’s about “well, let’s try this, let’s try that, let’s do the other.”

Jim O’Shaughnessy
You know, Bill Bryson has a great book, America, One Summer. It looks at the ‘20s, and that was the America you’re describing. Like Coleridge...

Philip Howard
Coolidge.

Jim O’Shaughnessy
Coolidge — I’m thinking of the poet. Coolidge was vacationing near Mount Rushmore when the guy was making it. He had no idea he was doing it. His aide said to him, “Hey, there’s some crazy guy up there who’s carving the presidents’ faces into this mountain.” And Coleridge was like, “Cool, let’s go look.” He didn’t ask for any funding. He didn’t go up there and say, “You can’t do that.” He just was like, “Wow, that’s really cool.”

Philip Howard
Cool.

Jim O’Shaughnessy
And back to your tinkerer thing — like Claude Shannon, one of my heroes. Really, because that’s all he did. For those who don’t know, Claude Shannon came up with information theory. He should be, in my opinion, as famous as Einstein. And yet he was just a really, incredibly colorful character. He worked on whatever was of interest to him. So you got a lot of trumpets that shot fire out when you hit a note, you got mechanical chess games, you got all of that — but also you got information theory. And I definitely think... I’m also vehemently opposed to this whole generational “oh, this young generation doesn’t know anything, blah, blah.” That’s total bullshit. These are incredibly talented people, who I just feel intersect with your thesis, because they’re straitjacketed.

Philip Howard
They are straitjacketed. And I think they’re held back by these conventions. We look back at the Victorian age and laugh at how stultifying it was and stuff. Victorians have nothing on us — I mean, they were like hippies compared to us. We are so much more...

Jim O’Shaughnessy
More brothels per square mile in London during the Victorian age than at any other time.

Philip Howard
We are so repressed by, really, a philosophy — a kind of anti-invention philosophy, where being yourself is a danger as opposed to an opportunity. I was thinking about this. I’m asked sometimes by people, “Well, you’ve been at this 30 years, you’ve really had a lot of failure. So...”

Jim O’Shaughnessy
But you’ve been very persistent.

Philip Howard
Well that’s what they say. “So why are you so persistent?” And this has cost me a lot of money. I deemphasized my law career and everything, because I really believed in it. And it’s not like I’m a saint. I don’t wear hair shirts. I enjoy life. I like — like you — fun. I’m playing in a golf tournament this weekend, or whatever. But the reason is that I know, and you know, and the attorney general I was talking to knows, and a bunch of other people who are on my board now, that I’m right: that we’ve created a system that’s fundamentally discordant to the American spirit.

Jim O’Shaughnessy
Yes.

Philip Howard
When I was in college, I got lucky. My family had no money, and I got a job at a federal poverty program at the Oak Ridge National Laboratory. Somebody saw that there was this kid going to an Ivy League school, and so they plucked me out and made me the gopher to a Nobel Prize winner.

Jim O’Shaughnessy
The creator of the multiple-worlds thesis of quantum physics, right?

Philip Howard
Right. And so I spent three summers as the gopher to a Nobel Prize winner.

Jim O’Shaughnessy
How cool is that.

Philip Howard
I ended up publishing papers when I was a teenager on post-nuclear-war recovery and stuff like that. But the thing I learned — we were in a little small group at Oak Ridge, a civil defense group, about a dozen people, an interdisciplinary group: economists and physicists and chemical engineers. What I learned about them is that they thought things through for themselves. And when they thought they understood something, they didn’t let go of it. It wasn’t a question of whether it was accepted or not; it was whether they felt they understood whatever the issue was, whatever the dynamic was, and it became their truth. And they wouldn’t give it up because somebody disagreed, unless the person who disagreed came up with a compelling reason why it was wrong. And I sort of feel that way. I feel that what we’re talking about is true. So why would I give it up? It’s incredibly important.

Jim O’Shaughnessy
Yeah. The principle of parsimony basically tells us that... It’s Occam’s razor by a different name. It works a lot of the time when you apply it to groups and things like that. I was thinking of somebody I had on in the early days of this podcast — Nick Gruen.

Philip Howard
Yeah, I was just on a Zoom with him.

Jim O’Shaughnessy
Okay. And he really sold me on this whole jury idea, which—

Philip Howard
The citizens’—

Jim O’Shaughnessy
The citizens’ jury.

Philip Howard
The citizens’ assemblies.

Jim O’Shaughnessy
Yeah. Why aren’t we trying those? My attitude is: let a thousand initiatives bloom.

Philip Howard
Yeah. Because it’s going to work, and get new ideas, and create... Another thing about society we don’t really understand is the role of moral authority. Citizens’ assemblies, for example: you don’t have to have power to be influential. You could convene a citizens’ assembly on the issues we’re talking about, and have them come up with their own interpretation and comment and so on. And it would have power — not because somebody can push a button to make it happen, but because real people got together and came up with that conclusion. George Kennan, the diplomat, toward the end of his life said he thought American government needed a fourth branch of government. He called it a council of state, but it was really sort of a council of citizens. His fourth branch would have no power. Its only job would be to comment on how the other branches were doing.

Jim O’Shaughnessy
Yeah. Well, you know, didn’t we used to have that in the so-called fourth estate? Journalism has descended right along with government. Because I was a real junkie for — okay, really outing myself as a nerd here — but during the Watergate hearings, I was 13 years old, and I spent all summer watching them. And that feels like a profound loss to me, because — nothing, of course, was perfect — but journalists sort of became the fourth estate that served that function.

Philip Howard
Walter Cronkite. Chet Huntley. These people had moral authority and credibility. If they said something, you believed it.

Jim O’Shaughnessy
Yes.

Philip Howard
And we just don’t... So we’ve lost the moral authority. One of the innovations that has worked in the last 30 years in America is the idea of base-closing commissions. It was politically impossible to close down unnecessary military bases. So one of the recommendations of the Grace Commission under President Reagan was to create independent commissions, appointed with so many by the minority leader and so many by the majority leader — but they weren’t partisan, they were retired generals and such — and they would come up with a set of proposals about which bases to close. So in the 2005 Base Closing Commission, which happened to be run by a guy I went to school with, they came up with recommendations to close or consolidate 50 bases, saving tens of billions of dollars a year. And Congress had the power to vote it up or down, but that’s it. So there’s none of this bickering going back and forth, and the congressman had plausible deniability: “I’m sorry that the base was closed here, but I couldn’t do anything about it, it’s all part of a package.”

Jim O’Shaughnessy
Yeah.

Philip Howard
Great. That’s kind of an innovation. That’s good. But the base-closing commissions had moral authority — they came up with the right answer. So I think we need... and I want to run it. I want you to appoint me to run it. You run for president, then appoint me.

Jim O’Shaughnessy
What did Sherman say? “If nominated, I will not run. If elected, I will not serve.”

Philip Howard
I want you to appoint me to the Recodification Commission — to methodically go through every area of law and turn 50,000 pages into a thousand pages, and not do away with anything, just make it work. Make it a principles-based system, more like the Constitution. And give people defined authority frameworks. Have courts not second-guess it, but only decide whether someone transgressed their authority. That should be the role of courts — not second-guessing. I mean, are the benefits of the transmission line worth the harm of building it through a pristine forest? That’s not a legal question. That’s a policy question, and ultimately a political question, and somebody has to make that decision. Otherwise, today we don’t have the transmission line, so we can’t get the power from renewable sources to the cities or to the data centers or whatever — because the process goes on for a decade. It’s crazy.

Jim O’Shaughnessy
My company, O’Shaughnessy Ventures, is doing a lot with AI. What do you think about that? What do you think about humans who — as you mentioned, not even AI seems to be able to make sense of all of these laws — but it probably is going to do a better job serving a human? By that I mean: have every regulation put in there, have it translated into English, show where it conflicts with other rules and regulations, so that at least — like a human, not even a committee of humans, could do it, but for AI it’s trivial. But not as a ruling — as in, “Here’s what you’re dealing with. Now, you humans, figure this out.”

Philip Howard
Yeah, completely. So I think the closest analogy I can think of to AI is the steam engine. You went from manual labor to a machine that could really do powerful things, and could be harnessed onto tractors or whatever. I have some senior AI people writing for my Free Press series that’s coming out, called Reboot Almost Everything. It’s a 20-part series, coming out in August. And so they’re talking about uses of AI. Reed Hastings, talking about how every student can now have a tutor — it’s fantastic. There are all these fantastic opportunities with AI. Ultimately, though, someone has to be accountable for tough choices.

Jim O’Shaughnessy
I agree.

Philip Howard
And AI is not accountable. So someone needs to—

Jim O’Shaughnessy
The human running the AI needs to be accountable.

Philip Howard
It needs to be accountable.

Jim O’Shaughnessy
I agree.

Philip Howard
So we’re going to need to come up with... A senior person at Google is writing an article on what they view as the proper AI oversight. It’s really interesting. It really is a brave new world, and the opportunities are fantastic. But the challenges of coming up with human oversight — because values... AI can mimic values.

Jim O’Shaughnessy
Right.

Philip Howard
But it can’t really have values. And there’s a lot of ethical theory about how ethics can’t be applied in advance — you always have to be in the situation.

Jim O’Shaughnessy
Situational.

Philip Howard
It’s always situational. And somebody has to be overseeing AI, and somebody has to make ultimate calls. And coming up with those structures is going to be challenging, too.

Jim O’Shaughnessy
Yeah. I think that one of the things that AI can do splendidly is to take those millions and millions of words and boil them down and put them in plain English. And by the way, I think they should do it for business agreements too. You can’t use anything online without agreeing... I don’t know — do you know anyone who’s read the terms and conditions?

Philip Howard
My favorite is when you go to a doctor’s office and they have a little thing there above the receptionist’s desk, and they say, “Okay, now sign here.” And you never see the agreement. And they say, “Okay, now here comes another one, now sign here.” You never — they don’t even go through the pretense of showing you the agreement. You’re just signing stuff. It’s truly the reductio ad absurdum of modern legal life. Crazy.

Jim O’Shaughnessy
So tell me a little bit about the series that you’re doing for The Free Press.

Philip Howard
So the series is called Reboot Almost Everything. It harkens back to our discussion about the need to change the operating system. So it’s not about policy. We go area by area, and we have an expert set up, in give-or-take 500-word essays — these are like one-page, very short essays — but with prominent people, like Reed Hastings or Mitch Daniels, saying, “Here’s the problem: government has become unmanageable, it has all these harms. Here’s the solution: we have to change civil service systems and get rid of union controls and do this.” I’ve written the introduction, and I’ve written one on litigation. I said, here’s the problem: we have an impartial system of litigation in this country — that’s a good thing, and people trust it to be impartial — but it draws no boundaries of who can sue for what. So where’s the law part? It’s kind of “sue for anything” rather than law — not lawsuits, but “sue for anything.” And so we’re missing something. And the harm of that is not just that you get these occasional crazy verdicts, but that people don’t feel free in daily life. They won’t let their kids go out and play alone, because if there’s an accident, they might be liable.

Jim O’Shaughnessy
Our staff here is quite young, and before you got here we were talking about... I grew up in the 1970s. We were free-range kids. We could do whatever we wanted, as long as we got home.

Philip Howard
Right. And so what’s happened is... A couple of decades ago there was a terrible accident on a sledding hill in Greenwich, Connecticut.

Jim O’Shaughnessy
I remember it well.

Philip Howard
And someone got a verdict of $6 million. And the result of that was not... I mean, Greenwich is a rich town, it could afford it. The result was that sledding hills across the country closed down.

Jim O’Shaughnessy
Yeah. Including that one.

Philip Howard
Right, including that one.

Jim O’Shaughnessy
I used to take my kids there.

Philip Howard
Right. So all of a sudden, because of a lawsuit brought by one person — no deliberate policy choice — the trade-off judgment about whether the risks of sledding outweighed the fun of going out in the winter and the snow was not being made by anybody who’s politically accountable. It was being made by the fact that somebody brought a lawsuit. And there was a similar case in England around the same time, where somebody — terrible accident — dove in a lake and became a quadriplegic. Terrible accident. But there were no hidden dangers there. Sure, you could run into something if you weren’t watching, but people had sledded on that hill for decades—

Jim O’Shaughnessy
It was a rite of passage for your kids.

Philip Howard
Yeah. And so in England, there was nothing hidden — it was just a freak accident. It was tragic. But the county that owned the lake was so scared of liability, because there were two or three near-drownings a year — a big lake, people swimming, bad things could happen — that they had determined to close the lake down. And then this accident happened. So the court said, “Well, this is foreseeable, therefore we’re going to grant damages to this person.” It goes up to the equivalent of the UK Supreme Court, and they order the case to be dismissed. They say, “It is part of our role” — as the lead judge put it — “to protect the reasonable freedoms of people in society, including the freedom to take risk. Do we require that rivers and lakes close down because of the certainty that some accident will happen? Do we require all trees be cut down because some child may climb one and fall? We will not tolerate a dull and gray safety regime. We are here to protect the reasonable freedoms, including the freedom to take reasonable risk.”

Jim O’Shaughnessy
What a great decision.

Philip Howard
And it’s called the Tomlinson case. And that’s what we’re missing in this country: no one is drawing those boundaries. So one of my pieces in The Free Press talks about how you would do that. You could have a state pass a statute that says the judges shall have the responsibility to draw the lines of reasonable dispute in any lawsuit; and in any case that might affect the freedoms of people not in the courtroom, the court shall make a legal ruling on the boundaries of acceptable risk.

Jim O’Shaughnessy
See, I’m a big fan of the book The Beginning of Infinity. And he talks a lot in that book about the precautionary principle, and he links the excesses of the precautionary principle to, essentially, the death of societies, because they can’t innovate anymore.

Philip Howard
What happens if.

Jim O’Shaughnessy
Yeah, that’s David Deutsch, right. I read it when it came out and I liked it a lot, but then when I reread it, it just mapped over to what you’re talking about. So, okay, let’s play a game. I am not the president — that will never happen.

Philip Howard
Oh, come on. I like it. President O’Shaughnessy. But think of all the trouble people have spelling it.

Jim O’Shaughnessy
Exactly. When I’m in Asia, they just simply call me “mister.”

Philip Howard
Oh, yeah, good.

Jim O’Shaughnessy
But I can influence the president. And he assigns you to this role that you’ve asked me to assign you to. What are your first five... What are the first five things that you’re going to promulgate?

Philip Howard
Well, the first thing would be to liberate people’s freedom to be themselves, by drawing the lines of who can sue for what — and making judges, even though it’s hard, draw these boundaries so people can do that. The second thing I would do is say: for democracy to work, the elected executives — governors and mayors — have to have basic managerial tools. They have to have the authority to decide not only what to do, consistent with the legislation, but who’s good at doing what, how to allocate money, how to adapt to new circumstances — all the managerial choices that I’m writing about in this little book that’s going to come out in January, called Burning Money. So I’d do that.

I would unleash — American infrastructure was built by our great-grandfathers. I mean, literally, water mains and rickety power lines all over the Northeast. It’s crazy. You would unleash that by creating a really simple authority structure. For starters, I’d write a law that says: notwithstanding any other law or regulation to the contrary, for the next five years, transmission lines shall be approved in the following process. There will be a notice of proposal. There’ll be an environmental review of not more than 50 pages, to be completed within three months, only talking about major impacts. There’ll be a chance for the public to comment in a short period. And then these designated officials shall have the authority to make trade-off judgments consistent with this. Their decision can be second-guessed by a designated official — the president, whoever it is. And the role of the courts will only be to determine whether, in any of these steps, they’ve transgressed the boundaries of their authority. So you have essentially a one-page document that allows for transmission lines, or whatever we’re talking about, to be built. It would be a slightly more elaborate process for a new nuclear plant, but it wouldn’t be 30 years — which is more or less what it is today.

So you’d simply go, piece by piece, and create authority structures. And I would also, to the greatest extent possible, re-empower local communities to do things in their own ways — whether it’s running schools or doing their parks — decentralized as much as possible, so that people can wake up in the morning and feel they can make a difference.

Jim O’Shaughnessy
You’ve got my vote. I think maybe we’ll run you for president.

Philip Howard
No, I just want to run this Recodification Commission. I really do. I’m getting a little old, but I’m still vigorous enough for now. Napoleon appointed four judges to redo all the laws of France — criminal laws, property laws, estate laws, tax law, everything. Everything was run by a prominent judge named Portalis. And in six months, they came up with new frameworks for all of the laws that affect France. Then they were debated in the legislature — Napoleon actually presided over a bunch of those — and they were enacted. And the result was the Napoleonic Code, which is still the basis for civilized law in half the world.

In the 1950s, a committee from the American Law Institute, run by a guy named Karl Llewellyn, a very prominent professor, said it’s ridiculous that we have — what was then — 48 different states, 48 different contract laws, so that anyone doing interstate commerce has to hire 48 sets of lawyers to comply with stuff. This is crazy. So let’s create a uniform commercial code. And they devised it. It has all different chapters — to do with security interests and commercial sales, different chapters for each one. It didn’t take them that long. And versions of it were adopted by virtually all 48 states. That was one of the things that stimulated the postwar boom: everybody had the same set of principles when they were doing contracts. Well, we just need that for society in America.

Jim O’Shaughnessy
Yeah. And it’s funny too, because I was thinking a lot about World War II — it plays a part in my fictional thriller that I was telling you about. It spans... it ends in 2027, it starts in 1939, so it’s quite the epic.

Philip Howard
Wow, cool.

Jim O’Shaughnessy
But I was thinking about America back then, and the thought struck me — and then I saw other people talking about it as well: if you buy into this idea of the American empire, which I don’t... the idea that for a brief period at the end of World War II, we had a weapon that could colonize the entire world if we so chose to. What did we do? The opposite. We did the Marshall Plan. We rebuilt Germany, we rebuilt Japan. And so I feel very patriotic about that — that America could have... If you look at every other so-called empire in history, if they had that weapon, they’re going to run the entire world. That was never in our DNA.

Philip Howard
And if Donald Trump had been in charge... So that’s why I think Americans intuitively know that’s bad, too. He really has accurately scoped out many of the idiocies that we’ve talked about. He doesn’t really have a vision on how to fix them, but America is a place where people not only wanted to do good for themselves, and innovate, and have agency — they also wanted to do good. And I think that part of America is really important. Obviously our moral authority is significantly diminished under the current administration. That’s the thing we need to come back to. But part of what I’m talking about — when you have a principles-based operating system, it is activated by people acting on their values and their judgments. Not just using their common sense, which is important, but also their values: what’s the right thing to do here? And so America’s missing that. There’s no reason why we can’t get it back, but we have to have a legal operating framework that allows us to act on our values — that doesn’t tell us how to do things. I think there’s a historic moment. I really believe this. There’s a historic moment waiting for us right now, and it is to correct course and face the future with new tools — AI — but with old values and an old sense of responsibility.

Jim O’Shaughnessy
Yeah. Because the effects of the current system are also not difficult to see. You create a group of people who feel no sense of agency, who feel infantilized, who almost get trained into learned helplessness. And my version of America is the opposite of all that.

Philip Howard
Right. Well, I’m going to speak at Notre Dame in October, to a bunch of people. And I’m going to Purdue at the same time — which Mitch Daniels has gotten roped into running again. I’ve actually been targeting Catholic universities, because I think that what you just said is something that Catholic theology deeply believes: subsidiarity, agency, people own themselves, they own who they are. So we need to build a cohort in support of that.

Jim O’Shaughnessy
And I think, at least in America, it’s “catholic” with a small C. In other words, it’s universal in this country. And I don’t know whether you watched any of the reactions of the Europeans in the United States for the World Cup. They’re absolutely delightful, because they’re like, “I thought America was just crime-ridden and horrible.” And they’re blown away by Costco.

Philip Howard
Right. But I’m blown away by Costco too, by the way. Anytime I can get 50 pounds of crunchy peanut butter, I’m there.

Jim O’Shaughnessy
You’re there. But the point is that when regular people are allowed to experience something and then share that experience, you again are reminded that, for the most part, most of what is the civilized world shares a lot of values in common with one another.

Philip Howard
Completely. So let us be that. Give us a framework that allows us to be ourselves, and allows us to do things in groups differently than other groups — that does not force us into a... You know, I’ve always said, people say, “Well, America’s all about diversity.” Actually, I think America is all about conformity. The Swedes go to Minnesota, and the Hasidic Jews are in Brooklyn, and the intellectuals are on the Upper West Side, and the techies are all in Silicon Valley. It’s about conformity. What America did that was really different is it tolerated a diversity of conformities.

Jim O’Shaughnessy
Yes.

Philip Howard
And so there were all these different communities, but all with these core values that they shared: reciprocity, living together in the same community. Fantastic. It’s a great thing. And all the innovation that comes out of all these different groups doing things in different ways — well, let us do that again.

Jim O’Shaughnessy
Yeah. And I love the line about conformity, because there’s so much truth to it. Of course, in both investment theory and social theory, there is this notion of the clustering effect, and, you know, like seeks like. But okay, fine — let’s grant that as an axiom. You’ve got to allow your view, where, yeah, you can have your values, and they might be very different than this group’s over here, but as long as you have an underlying framework that allows for that to happen, and for people to take control. Like your idea about local city ordinances or state ordinances. And the attempt to create a monoculture — monocultures always die. If you know anything about evolution: monocultures die.

Philip Howard
Right. They don’t grow, they don’t innovate. Whereas when you have these cells of like-minded people — one, innovating in their own way; two, competing with other cells in their own way — then all of a sudden you have this movement all the time, and you get this great stuff happening. So I think the American character is there — obviously you do too — but it needs to get unlocked. And so that’s going to require a new narrative and a new vision. And I’m roping you into it.

Jim O’Shaughnessy
Float like a butterfly, sting like a bee. Well, Philip, I love your work. As you know, I served on your board for many years. I hope this is the time, because I’ve got six grandchildren now, and I don’t want them to grow up in this giant squid of regulatory morass. We had a driver in Switzerland once, and it turned out it was his last day — he was retiring. And sometimes I enjoy just chatting with a variety of different people, so I started a conversation. I’m like, “So, tell me about yourself,” and everything. And the first thing he led with was Switzerland: “I’m born and raised in Switzerland. This is my last day of work, and tonight I’m getting on a plane and I’m going to Australia.” And I’m like, “Wow, okay, why?” And he goes — as beautiful as Switzerland is, as much as he loved Switzerland — he said, “I can no longer be in a culture where that which is not compulsory is forbidden, and that which is not forbidden is compulsory.” And so it made me think... In the old days, and even now — we do a lot of investing in startups and things like that — the number of incredibly talented people, and I mean off-the-charts talent, who still want to move, work, and live in the United States... That, to me, seems like just such a huge, asymmetric, unfair advantage that this country has. And we’re going to squander it. Which is insane to me.

Philip Howard
So, look at what’s going wrong. We have to change it. It’s just so obvious. People just have to wake up to the reality that this framework that we’re laboring under is broken for no good reason.

Jim O’Shaughnessy
And not only broken — it’s the wrong framework.

Philip Howard
Yeah, it’s wrong. So give us back the freedom to be ourselves again, to roll up our sleeves. That’s what’s needed. It’s going to take a new movement. It’s got to be invented. It won’t happen because somebody else does it.

Jim O’Shaughnessy
Right.

Philip Howard
It’s only going to happen because we do it.

Jim O’Shaughnessy
Yeah. Well, as always, I love talking about all of this. I could go on for hours, but I know that we both have other engagements. We have a tradition here, and you’re going to get... You might like this, because you don’t even have to be a czar, you don’t even have to be appointed. We’re going to give you a magical microphone, and for one day you are emperor of the entire world — not just America. But you can’t put anyone in a re-education camp, and you can’t kill anyone. What you’re going to be able to do is incept them. You’re going to speak into that microphone two things, and the entire population of the world is going to wake up whenever their next morning happens to be, and they’re going to say, “I just had two of the greatest ideas I’ve ever had, and, unlike all the other times, I’m actually going to act on these two things.” What are you incepting in the world?

Philip Howard
Oh, interesting. In any free society, you must be free to follow your star. That’s number one. The second thing I would say is: you are not alone. You exist in a community and a culture, and it’s your responsibility to be a responsible member of that culture.

Jim O’Shaughnessy
I love both of those. You’ve written tons of books — you can find them everywhere, Amazon, in bookstores, et cetera. And when is the new book coming out?

Philip Howard
The new book’s going to come out in January. It’s called Burning Money: How Public Unions Made Government Unmanageable.

Jim O’Shaughnessy
That’s a loaded title.

Philip Howard
My most recent book is called Saving Can-Do: How to Restore the Spirit of America. It’s about the whole idea of striving.

Jim O’Shaughnessy
No, I read it.

Philip Howard
The idea of striving.

Jim O’Shaughnessy
Yeah, it’s really, really good.

Philip Howard
But these are short books. I’ve taken to writing 100-page books.

Jim O’Shaughnessy
Just like the revolutionaries, right? They’re more like the…

Philip Howard
Pamphlets.

Jim O’Shaughnessy
The pamphlets, the Federalist Papers.

Philip Howard
Common Sense.

Jim O’Shaughnessy
Common Sense. They had a lot of impact. So, Philip, I wish you absolutely the best of luck.

Philip Howard
Great to be with you.

Jim O’Shaughnessy
Thanks for joining.

Leave a comment

Subscribe now

Share

Jim and Sangeet discuss AI-native companies, the future of knowledge work, American and Chinese AI models, creative “exhaust,” changing career paths, and how to compete when the rules of the game are constantly being rewritten.

We’ve shared some highlights below, together with links & a full transcript. If you like what you hear/read, please leave a comment or drop us a review on your provider of choice.

Links

Apple Podcasts

Highlights

The Cutting-Room Floor Is the Real Asset

Sangeet: If value chains are moving from output to outcome, then the creative exhaust is going to be worth more than the finished work. Think about writing a book. For every word that makes it in, there are probably ten or twenty words in wasted drafts, and maybe five hundred more sitting in notes that are genuinely valuable but never see the light of day. They only exist to help you get to the output, so we treat all of it as waste. But that is exactly where the learning sits.

For the last sixteen years I’ve captured everything I read, every thought, every connection, in a tool called Workflowy. Every day I’d add to it. Every year I’d take a week off just to move ideas around and see how they connected. I could never really do anything with it, until now. I took the whole thing and turned it into a knowledge graph that links all those ideas together. Now it can tell me where the gaps in my own thinking are, the connection I’ve been circling for years but never actually made. What I used to think of as exhaust turns out to be the most interesting part.

Jim: The analogy I use is what was left on the cutting-room floor.

Sangeet: Correct.

Jim: And I’m a prodigious note-taker. For forty-five years it was all by hand, and now we’re digitizing it. Some of what I’m seeing, I would never have thought of in that particular combination, even though they’re my own notes. The AI can basically go in and say, “Dude, you’ve been saying the same thing for forty-five years, how come you never acted on it?” And out of that come whole new ideas, whole new books, whole new ways of learning.

Sangeet: Exactly.

Don't Think Electricity, Think Agriculture

Sangeet: I think the shift to AI is very foundational. It’s not something you can compare to the shift to electricity. I’d say it’s more like the shift to agriculture, or to wood, or to minerals.

Jim: That’s the argument I’ve been making. Don’t think electricity, think agriculture.

Sangeet: Exactly. Because the fundamental input into the value chain is changing. And when the input changes, an entirely new production system has to be built on top of it. But most of our industrial mindset assumes the input as given and treats the production system as the thing you act on. Now we have a new input, and we haven’t even begun to rethink what the production system should be. That’s really what China is working on, treating both energy and AI as new inputs into fundamentally new production systems.

The point isn’t whether China is right or the US is right. It’s that we’re still incredibly early. We’ve just discovered agriculture. We’ve worked out how to make the ground a bit more fertile. We haven’t yet figured out that one day we’re going to make clothes out of cotton. We’re that far from the whole value chain.

Transcript

Jim O’Shaughnessy

Well, hello everyone. It’s Jim O’Shaughnessy with yet another Infinite Loops. I’m delighted to welcome back Sangeet Choudary, the best-selling author of Platform Revolution and the one I really want to talk about, the newer Reshuffle: Who Wins When AI Restacks the Knowledge Economy. Welcome back.

Sangeet Paul Choudary

Thank you, Jim. So glad to be here.

Jim O’Shaughnessy

I have certain guests who, when I see them on my schedule, I get excited, and I so enjoy talking to you. But for people who might not be familiar with your work, let’s do a bit of a recap of your thesis so we can level-set for our listeners and watchers to understand where you think we’re going.

Sangeet Paul Choudary

Absolutely. The key thesis I talk about in Reshuffle is that when we think about the impact of AI on knowledge work, we often tend to think of AI in the same way we’ve thought of previous forms of mechanization, which have typically impacted relatively more codified, standardized workflow. AI is fundamentally different, because work that was previously considered tacit and bound inside human cognition can now be broken down and taken over by machines in a way that was previously not possible. So one of my key points is that the traditional way of looking at the impact of mechanization on traditional forms of work does not apply when we think about the impact of AI on tacit knowledge work.

What I mean by tacit work is fundamentally this. Take the example of solving any market analysis problem. There is no fully codified workflow. You make up your workflow as you get into the problem. You define it, and you learn from the information you’re gathering. It’s difficult to explicitly codify the workflow, the number of iterations, what good looks like. That’s why traditional forms of mechanization did not apply to tacit work, but today AI does. You can see that with the market analysis example: you can get a really good market analysis report using Claude, which is getting better every few months.

So my key point is that when we looked at previous forms of mechanization, we used to think about the impact primarily in terms of automation or augmentation, because you were taking a predefined way of doing work, looking at different steps in that predefined way, and inserting a machine at specific steps. It was either automating that step or task, or augmenting the human on that task. A lot of us are still taking that same model when we think about AI and applying it. That is what I call the task-centric, automation-based way of looking at AI.

The real story we’re missing in that process is that when previously known, modularizable, non-definable forms of work suddenly become redefined and remodularized in fundamentally new ways, the structure of work changes. Who performs which work changes. Take the example of consulting. The pressure on consulting firms is not simply from model providers. The pressure is also from the fact that model providers now change the division of work between what customers could have done in the past and can do now versus what consulting firms can provide them. When customers take more of the work and model providers absorb some of the other work, the consulting firm in between has to rethink not just what to do with the work that remains, but what new work to go toward.

So the real idea of Reshuffle is that what AI does is unbundle our traditional work structures, whether it’s a workflow or an organization. These are specific configurations, what I broadly call bundles of performing work. It unbundles all of that. It redistributes what machines can do and how humans can reorganize what they want to do based on improving machine capabilities. With that, it creates the possibility for fundamentally new structures to emerge: new workflows, new organizations, new industrial boundaries. So the real impact of AI will not be in speeding up today’s work. It will be in reconfiguring everything that supports work, which is our workflows, our jobs, our organizations, our value chains. All of those are poised for reconfiguration. That’s the real idea of Reshuffle. When AI restacks the entire knowledge economy, the game will change, and hence the winners and losers will change as well. That’s the whole idea of who wins when AI restacks the knowledge economy.

Jim O’Shaughnessy

Yeah, and we are very simpatico on that idea. I think many people are asking the wrong questions and framing it wrong. One of the reasons they’re framing it wrong is because they’re captured by their priors. They’re captured by the old workflows, the hierarchy, the meetings, the departments, the job descriptions. I started thinking about this a while back and called my little thing the great Reshuffle. What I saw coming, and it really is, is changing the routing. AI is really going to change the way things get routed to different nodes. And there are going to be problems. There are always problems. But it could create what I would call a new distributed value mesh network.

If an earnest CEO who really wanted to understand what was going on hired you as a consultant, what would you tell them about how he or she should work to design, maybe from first principles, around the new coordination that AI will allow?

Sangeet Paul Choudary

The place where I would start is how you think about strategy. Today, the typical way you think about strategy is in terms of answering two questions: where to play and how to win. What’s the playing field going to look like, and how do you think about the winning game? The first thing I would talk about is that the playing field within which your firm is playing is fundamentally changing. I’ll give a few different examples. If you’re in the knowledge services industry, the professional services industry, clearly the playing field was structured around the assumption that access to certain forms of knowledge work was expensive and proprietary, and hence you could hold it internally and license it or charge for access to it.

So when access to certain forms of knowledge work suddenly becomes very cheap, because AI does perform certain forms of knowledge work, within limitations of course, but it dramatically reduces the cost of accessing certain forms of knowledge work, how does that then change what is differentiated versus what is commoditizable in your industry logic? Or take it all the way away from professional services to a very physical industry like material sciences, plastics, and compounding. Traditionally, the cost of compounding was that if you had to identify or discover new compounds, you had to go into the lab, run a lot of tests, and come out with compounds. Today AI can generate new compounds from scratch. So the value then shifts to how you match the compound to the process, to the demand profile.

Because alongside that, the number of use cases at the front end is also dramatically expanding. As the supply of compounds increases and the demand for different use cases increases, how do you match the two things really well? That’s where the new constraint sits. So the first thing you would want to look at, if you’re a CEO, is that you have to follow the scarcity, because you can compete on the basis of what’s scarce, not what’s becoming abundant. What’s becoming abundant is going to get commoditized. Margins associated with that particular activity are going to get compressed. So you need to think about where your new scarcity lies, and how you can create defensible business models around owning that scarcity. That’s on the playing field side.

At the same time, you have to think about AI strategically in terms of your organization. Today a lot of CEOs are just focused on: we need to get AI adopted, we need to roll this out, we need to get teams on board. All of that is a good starting point, but it is only that. What we should really be thinking about is that as AI gets adopted in our organizations, there are three things changing simultaneously. One, the capabilities themselves are changing, because Claude, OpenAI, all of these are improving on a daily basis. With every new release, what the machine can do and what humans can do changes. So the capabilities from a pure model perspective are changing.

Which of those capabilities actually get adopted in value-creating workflows in the organization is constantly changing as people learn how to adopt the technology. And as people adopt the technology, how they change their own work is constantly changing. So if you’re a CEO, the biggest thing you need to think about today is how you manage this constantly evolving capability set, because you’ve never had such a constantly evolving capability set before. You had a top-down capability set where you said, we’re going to hire these people, map them into these skills, and keep training them on this basis, so the skills you have access to constantly change but you managed how those capabilities evolved. As you deploy AI in the organization, it’s going to evolve on its own.

And not just the machine capabilities, but how they’re adopted, and more importantly, how your people are changing their work around it and how they are discovering new capabilities or moving to new things. That’s going to change what you can do with this evolving capability set. So there are two things here. One, the nature of differentiation and competitive advantage in the playing field is changing. Two, the capability set with which you can innovate from inside is changing. It’s really at the intersection of these two things, given that they are changing for every company across industries. So your competitors are not going to look the way they used to look in the past.

Because once certain forms of knowledge work that were protected by your industry boundary become available outside that boundary, new competitors can come into your industry where they could not have in the past. I’ll give a very simple example. Think about what’s happening to customer support. Traditionally, customer support was something you performed in a contact center. It was a very closely bound industry boundary in terms of who runs a contact center and what kind of tools are provided to them. Today customer support can be performed by AI agents alongside human agents. So you have companies like Microsoft and Salesforce, completely outside those industry boundaries, now entering the support industry, because they can access the capability of providing support without having to invest in training humans to build that capability from scratch.

So when you think about these aspects, the fact that previously scarce capabilities are becoming commoditized, that ways of differentiating are changing, that who can get access to and enter your playing field is fundamentally changing, and that your capability set internally is changing, that creates a very volatile and dynamic competitive playing field, both in terms of what you can do and where you can play. I think understanding and resolving that is the key challenge for CEOs today.

Jim O’Shaughnessy

Another thing I think we face: the authors of the book The WEIRDest People in the World, I don’t know if you’re familiar with it, make the argument that cultural lag is a real thing, and that it takes humanity a while to adapt to a new way of doing things. I think that’s true. But I also think it provides an asymmetric arbitrage opportunity. The asymmetric arbitrage opportunity is: are you going to be willing to move rapidly to a truly AI-first corporate or institutional structure in everything? If you are, it’s my thesis that you’re going to be able to eat the lunch of the players using the old playbooks. Is that one of the reasons? This is why you see the current top of the hierarchy, let’s look at movies, books, a variety of things, they’re not happy at all.

And yet, much like the movie industry, they tried to suppress VHS for years and years. They spent millions of dollars, they lobbied against it, and of course they lost. And then the wonderful irony is that VHS sales and other such sales ended up being a much larger part of their revenue, the very thing they fought all that time. Do you see something like that happening with traditional dominant companies today versus the upstarts?

Sangeet Paul Choudary

Yeah, I think so. It’s that particular element of a company native to a new technology versus a company migrating to a new technology, and the arbitrage opportunity for the company that’s native to it is not entirely new. What’s new is the rate of change, the speed at which this is happening, which confers a compounding advantage to the native player versus the migrant player. If I were to qualify this, take a different technological shift. Take the shift from desktop to cloud, which happened 15 years back. You had a company like Adobe, which moved to the cloud very successfully. There are Harvard Business School case studies about how well Adobe managed that shift, how well its CEO moved, how the CFO agreed to move from licensing to subscriptions. And yet it struggles today.

It has struggled ever since to compete with the native player, which was Figma. The reason it struggled to compete with Figma is that Figma was architecturally organized around the properties of the cloud. Adobe was using the cloud only as a channel. Figma was using it to redesign and reimagine the product architecture, the offering architecture, and the workflow supporting it around the capabilities of the cloud. To give a simple example, Adobe was built on a file-centric architecture. You had to create the file, and in the past you would send it over email. Now you could be on the cloud and have others coming in and commenting on the file, but it was still centered on the file-centric architecture, and the file was tied to the design division.

So the file-centric architecture preserved a certain logic. Figma, because it’s cloud-hosted, is created on an element-centric architecture, which means every design element the organization uses is managed in a central library. It can be reused across design files. So design files are very often reconstructed using new elements and common elements across the organization. There are two important unlocks because of this, and this shows the difference between the native player and the migrant. The first is that when you manage design elements in an organization-wide library, you’ve moved the value from design only to design and governance. Governance no longer sits inside the minds of designers, which is what was happening within Adobe. Now it’s managed organizationally. So the budgets you can access are fundamentally different.

And when you can represent design in terms of a cloud-hosted graph and not a design file, that allows multiple different players, marketing, sales, product, all of them, to work alongside the designer on the same file without forcing the designer to keep ensuring it is well validated and verified, because all that verification is happening centrally. My point is that Figma realized design was not an isolated activity. It was an activity that fed many workflows across the organization, and the cloud natively allowed that workflow spanning to happen across the organization. No matter what Adobe does, it cannot move in that direction. Ironically, Figma is now facing the same issue, because Figma is sort of an AI migrant.

It’s got this nice file structure, element-based, but then Anthropic, for instance, can infer connections between elements, can identify fundamentally new ways in which design files are being manipulated. It can do a lot more with the entire design system than a migrant like Figma can. So we see this cycle repeatedly: when a new technology comes in, if you have the opportunity to rethink the logic of the product, the workflow, your customer’s workflow, your organization, everything around this new technology, the starting point is whether you can really define what the new unit of value is. If you look at Figma versus Adobe, for Adobe the unit of value was the file; for Figma it was the element. So you could do everything at the level of the element.

Even if you opened up APIs for the ecosystem, your partners could be the same, but with Adobe they could only work on the file. With Figma, they could work at the level of the element and integrate at that level. So it fundamentally changes how companies organize, how they collaborate, how they compete. That is why there’s a huge arbitrage opportunity for players built ground up with the new technology. There is also a significant opportunity for players who are migrating, as long as they have several structural constraints that do not simply get wiped out. As an example, in professional services, you could be a copywriter at one end, or an audit and tax consultant at the other end.

As a copywriter, you don’t necessarily own structural constraints, whereas as an audit or tax consultant, you have the right of final sign-off, which is regulatory protected. So there’s a structural constraint that, even if the work gets taken over or commoditized by AI, you are able to hold on to the value at your end. It’s important to know under what conditions incumbents can retain value because of structural constraints, and under what conditions the AI-native player can fundamentally impose a game that the incumbent simply cannot play. All of those factors become very important when we think about who has that arbitrage opportunity.

Jim O’Shaughnessy

And one of the things, this is my view, I’m not attributing it to you, but I think one of the reasons we’re seeing all of what I view as desperate attempts for regulatory capture on the big frontier model designers and providers is because they understand that if they can’t get regulatory capture, if they can’t make the legal aspect of who gets to do what, then the playing field is truly a different playing field, because you’re not going to be able to be saved through the traditional things like copyright, all of the various legal procedures and protocols that we’ve built up over long periods of time. They’re all under attack, right?

Sangeet Paul Choudary

Yeah. I think there are two different issues, and let me know if I’m approaching this the way you intended it. When we think about copyright and other issues around value captured by AI models, there’s this element of ring-fencing what was previously a public good and extracting it the way you would a private good. AI enables you to create a transformation value chain where the end product is completely untraceable back to the input. Copyright law was built in an era that did not assume that kind of transformation, and essentially because of that it’s difficult to protect what’s happening here. This is not my idea. This comes from a well-known book called Power and Progress.

This has played out over the centuries, where every new technological shift, or many new technological shifts, has created opportunities to extract value by ring-fencing a public good and making it private, essentially because the regulation stayed stuck to the previous model whereas the technology imposed a fundamentally new model. In one way, that’s what we’re seeing here. The other thing that’s interesting in terms of how Anthropic and others, the model providers in general, are calling for regulation is because they also, I believe, realize that the American models and the Chinese models are playing a fundamentally different game. In the American model game, the model is sort of the end. So that is where value is supposed to be captured in the long run.

In the Chinese model, I believe the model is the complement that has to be commoditized in order to capture value at the complementary layers, especially when we think of physical AI and new production systems. The value there to be captured is in the energy system, in the production system on top of the model, which is the physical production system, robotics, and so on, and the overall coordination system in terms of how you build fundamentally new value chains, fusing the knowledge value chain and the physical value chain. So the fact that it’s a fundamentally different race and a fundamentally different game that the Chinese model providers are playing is also driving a lot of this concern around regulation.

Jim O’Shaughnessy

And which model, the Chinese version or the American version, do you think wins?

Sangeet Paul Choudary

I think they’re fundamentally different games. If we believe that eventually the knowledge value chain and the physical execution value chain are not two distinct value chains, the way we’ve been talking about digital and physical for the initial part of the digital era. When the digital era started, we always talked about the digital and physical value chains separately, and eventually we realized they are not really separate. You essentially create value by bringing the two things together. I think the same thing applies when it comes to AI. There’s the knowledge work value chain, and then there’s the physical work value chain, which converge.

I believe the way the model providers in the US in general are looking at it is purely in terms of what AI does to the knowledge work value chain, which is a fair way to look at it, because traditionally most value in today’s industries has moved to knowledge work. If you look at any industry, if you look at mining, or the example of plastics I took, the physical work gets fully commoditized and the value moves to the knowledge work. But if you look at the Chinese model in general, the two things are not fundamentally distinct. I take the example of Shein in the book, which clarifies this really well. If you think of Shein, the fast fashion player, the reason it’s interesting is that it creates a learning architecture that brings the physical and the knowledge value chains together.

It constantly senses new ideas and new trends coming up on social media. Then it converts that into a design using a network of designers, converts it into a small batch of production, tests it in the market, and with all of that it’s constantly training which batches work and hence how its physical production system and its design system should work together. So this idea of creating a learning architecture that spans both the knowledge work and physical execution is, I believe, where things are headed. But because in the West we’ve largely assumed that the physical side of things is commoditized, we tend to see the impact of AI only within the knowledge work value chain.

Jim O’Shaughnessy

Yeah. And I should note that we also have a publishing company, so we’re very concerned about copyright and are looking for new ways that the technology itself can unlock to preserve the author’s right to their work, to preserve the filmmaker’s right to their films, and so on. I think that is going to be a really important topic, because if you can’t cut the creators out, you have to come up with a protocol that works with the new technology. When everything can be digitized and the end product looks nothing like the inputs that created it, you’re going to get a lot of very unhappy people. So I think this is not just a business question, this is a societal question.

Sangeet Paul Choudary

Right, right.

Jim O’Shaughnessy

Because another question I would have for you: I sort of think that distributed value networks, mesh networks, where there is no central authority. So, for example, China had the Gutenberg technology way before good old Gutenberg came up with it.

Sangeet Paul Choudary

Right.

Jim O’Shaughnessy

But it had a very centralized command-and-control government that suppressed it, because the emperor wasn’t interested in people printing things that might be critical of the emperor. Whereas Gutenberg worked because Germany was not unified. It was a collection of city-states competing with each other. So China had the tech first, but Gutenberg was operating under a distributed network protocol, the protocol won. And I think another one of your points is that the coordination layer is going to be vitally important to determining who’s the winner and who’s the loser. Could you explain that a little bit, because you’re much better at it than me.

Sangeet Paul Choudary

No, for sure. This is one of the things I felt people were missing about what AI can do. The way I typically think of it is that when we think about the impact of AI on the underlying economics of what’s improving, we tend to think about two effects. Predictive AI is collapsing the cost of prediction. Generative AI is collapsing the cost of generation. What happens when the cost of something collapses is that it gets done more, in many more places, and hence it unlocks second- and third-order effects, because those previous constraints associated with those activities go away. Those things get done much more. The third thing these two framings miss is that the cost of translation, or coordination, is also going down with AI.

What I mean by cost of translation is that when a foundation model is trained on the world’s knowledge, it can translate between different domains in a way previous technologies could not. Previously, if you had to translate between different domains, you had to either rely on bespoke integrations, or rely on some form of power structure that was willing to invest in doing that translation so it could extract rents from it. It could be a broker or an intermediary, or it could just be what we call platforms, where they specify the interface, manage some form of the mapping, and then once they get sufficient traction, they force the ecosystem to follow the standard. So the translation happens through that mechanism.

Essentially, what all of that leads to is that there were two primary ways to coordinate multiple actors. You either had to get the actors to agree and reach consensus, and the example I take is the shipping container. Once trains, trucks, and ships agreed on the same format of the container, logistics got unlocked globally. So it’s coordination with consensus, or it’s coordination through enforcement and power, which is what, say, a Facebook or an Amazon or any of these large platforms do, initially heavily funded by venture capital, which allows them to gain scale, and then they enforce the coordination. My point with AI is that it allows coordination without consensus, because it collapses this cost of translation.

The reason that’s important is that today’s power structures are structured around proprietary formats, proprietary ways of doing things, proprietary workflows, proprietary interfaces. Essentially those power structures create walled gardens. If you take any industry, whoever owns the choke point, in some industries that’s the R&D choke point, in others the distribution choke point, whoever owns the choke point enforces the standard, the schema, and the way of working on everybody else. What AI can do is take outputs at every step of a value chain, learn from them, and translate them between different walled gardens in the same industrial system. The example I give is construction. In the construction industry, you have players like Autodesk and Bentley with different design formats.

That’s on the architecture and design side. Then there’s the downstream construction and engineering side. All of these tools and technologies don’t talk to each other, and the players providing these tools create their own islands, or walled gardens. What we’re seeing now with new AI-native construction players coming in is that none of them are trying to do design faster. Nobody’s attacking Autodesk straight up. They’re trying to dismantle the Autodesk logic by creating these translation layers, where they tell the user: no matter where your different teams are working, in which formats, we’ll help you see a unified view of the project. Through that, we’ll create a coordination-without-consensus layer.

Once enough demand moves in that direction and starts using this AI layer to make decisions, they would then want to flip it and enforce the interfaces on the various format providers. That’s the idea of coordination without consensus, where you can dismantle today’s power structures and create an alternate way to span the different formats. I think the new power structures it yields could be a combination of protocols, because you need completely open protocols to get different formats to work together, but then a different form of concentration at different points. It could be just one node that you capture, it could be a combination of different layers, but it would be different from today’s power structure. That’s where, going back to your point about protocols, that’s a fundamental Reshuffle pattern we’ll see as well: enabling coordination without consensus, breaking down today’s power structure, and creating alternate structures going forward.

Jim O’Shaughnessy

Yeah, and that’s where I got really intrigued in that part of your book, because I agree wholeheartedly. But if you study history, it’s really nothing new. By that I mean the distributed value architectures and protocols. The example I always use is the Rothschilds. The Rothschilds were five nodes without a central authority. The father sent each of his five sons to the capitals of Europe of the 19th century, the financial capitals. They had an amazing sub-layer of courier network. They had rented boats, carrier pigeons, ciphers that only they knew. But it was not routed to a central authority to make decisions. It was routed to the brother who could take the greatest advantage of it. And it’s an apocryphal story.

I think historians go back and forth on this, but because of this topology that the Rothschilds had, that was their key advantage over others. They had a better information network than government information networks at the time. Of course, the canonical story is Nathan Rothschild, through this courier network, knowing that the Brits won the battle against Napoleon. Then he took advantage of human psychology, went into the stock exchange, and sold British gilts, or bonds. Everyone thought Rothschild knows things ahead of other people, so everyone just rushed to sell. Of course, he had his agent buying from the plunging prices. And they literally controlled finance in 19th-century Europe until the telegraph destroyed their advantage. I see AI in a very similar role here.

I think it’s hard to articulate just how fundamentally transformational a technology this is, because you’re going to be touching a lot of third rails. That’s going to be messy, and it’s going to be a very difficult fight. What about the idea of measurement capture? You don’t have to control the entire network if you can control what gets counted. Could AI itself, as the new router of all this information, could we see a system where that just gets copied and copied and everyone’s using the same routing system? Or am I off base with that?

Sangeet Paul Choudary

No, that’s an interesting thought. There are a few complementary thoughts I have. One is that we’re clearly moving in a direction where firms are not going to compete on the basis of outputs. At the risk of using the cliché, outputs to outcomes, everybody’s talking about it, but what does that mean? I think that has something to do with what we’re talking about in terms of measurement capture as well. We’ve optimized firms around creating the best output, the most output, and scaling that output. We don’t necessarily know what it means to optimize against outcomes. I believe optimizing against outcomes is about owning a proprietary learning architecture, which helps you own the outcome better than every other firm and hence optimize your entire internal production architecture to improve that outcome better than anybody else.

What I mean by owning that learning architecture is this. When we think about learning, after 10 or 15 years of digital technologies, we still think about learning as what happens on the customer interface, personalization, that the system knows more about you, it’s learning about you. We’ve not necessarily seen learning to the same extent across the entire production architecture. Shein is one of those examples where, because it’s a proprietary architecture, you are fine-tuning every element of it. What should be designed, which kinds of design elements work well with which kinds of production factories, which production factories work well with which markets.

You’re fine-tuning every coupling in the value chain in terms of what works well with what. In new value chains, if you look at something like electric vehicles, you do have that learning architecture, because you’re simultaneously fine-tuning what the battery can do, what your charger can do, what your charging network should look like, and hence what the customer experience looks like as a combination of these three things. So there’s a coupling between battery capabilities, charger capabilities, charging network spread, and so on. Over the last 50 years, we’ve constantly moved away from inefficient vertical integration to modularization, first with outsourcing, then with cloud capabilities. Whichever way you think about it, it’s constant modularization, decoupling, making things more flexible and plug-and-play.

But when you move from outputs to outcomes, you need to own the entire production system in order to guarantee the best outcome. So we’ll see a new form of reintegration happening, structured around defining what should be counted as the right measurement at every stage in the value chain, toward ensuring you are able to guarantee the best outcomes to the end customer. That’s the way I would think about measurement capture: the ability to win the outcome game is determined by your ability to own the learning architecture, which is determined by your ability to dictate what should be measured at every stage, because that’s what guarantees the end outcome in the best possible way. I’ll throw a related idea against it as well.

There’s a recent HBR article I wrote that came out last week, where I essentially make the point that we’ve traditionally seen work and learning and skilling and all of these things as decoupled, in the sense that you go and perform your work, then you go somewhere else to learn, and then you come back and perform your work. With AI, what’s happening is that for the first time we’re working with a technology that’s constantly working alongside us. Hence it’s also measuring how we are working, and transforming how it behaves so that it can give us highly personalized feedback based on how we’re working. So we have created this.

We are moving in this direction where learning, measurement, all of that is going to happen in the flow of work, and hence which kind of measurements matter and what learning path they take you individually down is also going to be determined by AI. So I don’t know if that directly addresses it.

Jim O’Shaughnessy

Yeah. Actually, I’m looking at a question, because I believe pretty deeply in this distributed value chain, where, historically, if you look at all wealth creation, not extraction, but creation, it happens under these circumstances. The Greek city-states, all the way up. For politics and philosophy and all of that. It’s not just business, it’s societal, it’s political, it’s everything, the Gutenberg example. In your answer, I asked you this question that I’ve written down. I’m going to read it, because you answered it very much the way I’m looking at the world. I say: if AI is the new coordination layer, and the distributed architecture is the historical engine of value creation, is the highest value produced by controlling the layer, or by designing a layer that can’t be controlled?

And what you’ve just said is you’ve got to create a proprietary layer of knowledge, reinforcement, learning, all of that. So it sounds like we’re both directionally thinking the same way, right?

Sangeet Paul Choudary

Yeah, and I would agree. When I use the term learning architecture, there are two things I try to reinforce, because people have preconceived notions of what learning means based on how we’ve used the term in the last 15 years when it comes to business models. The first is that people just assume learning happens in the market, not across the production system. I think that’s going to be truly unique and new with AI. That is why, again, I believe the Chinese model of betting on commoditizing the model and capturing value from the production system, the energy system, and the existing coordination system on top of the physical knowledge production system is where value is going to be.

So that learning architecture piece is something I believe is not fully understood to the same extent in the Western paradigm of looking at technology. The second piece is essentially the other reason I use the term architecture. When we use the term layer, and I’m just trying to refine what we’re going back and forth on, the term layer is borrowed from the past several years of modularization we’ve gone down, where we’ve assumed certain layers are going to be commoditized and certain layers are going to be valuable. I believe that’s going to continue happening. That’s just how value migration works.

But in the past, it was possible to be just one layer and not do anything else, or at least be visible as one layer, even if you had adjacent control positions and adjacent points. The classic example being that Amazon has Prime as the visible layer, but it has that price-matching algorithm that runs at the back end which helps it retain the Prime position. But if I take the Tesla and electric vehicle example again, it’s not just what we call a layer today, but the couplings between layers and a proprietary new learning architecture that helps you understand how those couplings behave. As the technologies at each of those layers are improving rapidly, owning those couplings is where advantage accrues.

So those are the two reasons I stress the idea of the learning architecture in a way people have not used it with digital technologies, at least.

Jim O’Shaughnessy

Yeah, and again we are aligned, because we think about it at the architectural level as well. We started at O’Shaughnessy Ventures to be AI-first in every aspect of everything it does. And if you’re 66 years old, that requires a lot of open-mindedness about the way things are going to get done. Luckily, I’m very open-minded about these things. I definitely think you are absolutely right that people are not thinking big enough in many circumstances, because I think you’re spot on about thinking at the layer level. That’s a whole different conversation from the architecture level, and the ability for learning to happen in the workflow, to be reinforced, and all of that changes the way everything is done. My concern is, again, back to cultural lag.

We have been socialized to believe that I’m going to get this job, this is what I’m going to do, and this is how I’m going to be judged, by my outputs, and the whole deal. That is not what the future institutions look like to me at all. And I don’t think there’s necessarily a sense of urgency, like those of us who were early to machine learning and seeing what it could unlock. I hear a lot of people saying, oh, we’ve got to get going, we’re late. I think in the grand scheme of things, we’re still pretty early. Am I off base? Do you think I’m right there?

Sangeet Paul Choudary

I think we’re at that phase where we’ve seen the new capabilities that are emerging, we’ve seen how that could lead to new firms and new architectures. We have not yet seen all possible architectures in all possible contexts through which the capabilities can be used to create advantage. What I mean is that if you think of any of the previous shifts, and I think the shift to AI is very foundational. It’s not simply something that can be related to a shift to electricity. I would say it’s more foundational. It’s probably similar to a shift to agriculture, or wood, or minerals.

Jim O’Shaughnessy

Because that’s the argument I’ve been making. I’m saying, don’t think electricity, think agriculture.

Sangeet Paul Choudary

Exactly, right. Because the fundamental input into the value chain is changing. The previous input used to be very different, and an entirely new value chain has to come on top of it. So both agriculture and minerals are two things I would look at. Most of our industrial production mindset assumes the input as given and assumes the production system as the object of action. But now that we have a new input, we have to rethink what the new production system should be. And I don’t think we are thinking about that. This brings me again back to the China point, where they are working on both energy as a new input and AI as a new input into fundamentally new production systems.

I think it’s less a point of whether China is right or whether the US way of looking at AI is right. It’s more about the fact that we’re still very early. We’ve sort of just discovered agriculture. We’ve figured out how to make the ground more fertile, more arable, and so on. We haven’t yet figured out that we’re going to make clothes with cotton at some point. We’re too far from that whole value chain at this point.

Jim O’Shaughnessy

Yes, and again, I agree completely. The thing I’m struggling with as well, though, is this notion of, if you have this distributed, non-centralized mesh network protocol, a viable mesh should be forkable, it should be auditable, it should be hard to fake and hard to capture. So what happens if AI becomes the ultimate mesh capturer? By that I mean, we have the centralized model that we’re using in America, we have the commodity model that the Chinese are pursuing. It’ll probably be a combination of both. But what happens, if the AI is getting smarter and smarter, are they also compressing toward a middle? That’s a criticism I often hear about AI, that it doesn’t, unless you specifically say, hey, I want to look way out in the tail. What it does is compress all of the knowledge into a standardized common ground.

Sangeet Paul Choudary

Right.

Jim O’Shaughnessy

I’m being inarticulate about this, but the idea is: is it the ultimate enabler of these hard-to-fork, auditable, hard-to-fake, and hard-to-capture mesh networks, which I kind of think it is? I’ve been thinking a lot, and this is what I was looking forward to in getting your view, because I like to think I might be wrong. What happens if I’m wrong?

Sangeet Paul Choudary

So I’m going to again offer a complementary perspective here. I think what I’m saying and what you’re saying, if you bring them together, we could have an interesting theory. Let’s take the creative value chain. It assumes there’s a certain creative process that’s valuable, and the object of action in that creative process is the output that has to be created, whether it’s a book or a song or whatever that is. In the process of working on that object of action, there’s a significant level of creative waste it is willing to deal with, which is not going anywhere. It just goes out as creative waste. It does not have any place in that value chain. It’s all the unwritten drafts, all the messy notes, and so on.

I believe that if value chains are moving from output to outcome, the creative exhaust is going to be more valuable than the object of action, because the creative exhaust is where the learning architecture sits. Hence I believe everybody who has built a life thinking about perfecting the output should now go back to thinking about what to do with the creative exhaust. I wonder whether the protocol plays out most interestingly at the level of the creative exhaust, where my creative exhaust, what I waste, can be refurbished and reused by somebody else it perfectly applies to, who is at a certain point in their own creative exploration. I’ll try to give a couple of examples to illustrate that, and also share how I’m thinking about my own work with that context.

But the other thing, so there are two points I’m trying to make. One is that if we believe the input is fundamentally changing, which it is, which is what is scaring the creative industries, if we keep focusing on the creative object as the output, as the focus of production and the focus of improvement, if we stay focused on the output-centric model of creative work, I have a feeling that’s a loss. We are moving in the direction of: where does this output move into, what problems does it solve, how can I think about that outcome and create an architecture, a learning architecture, to solve that particular thing?

It’s easier to think about that when we think about electric vehicles, because we’re saying, okay, whether it’s battery technology or charging network, all of these are working toward one outcome, driving range. So you have to keep improving them. You don’t improve only the vehicle. You improve every component that was previously assumed as given, in order to get to the outcome, and the learning architecture is where the advantage is. It’s difficult to apply that directly to creative work today, because we don’t necessarily think of it in the same way. But I’ll try to share what I’ve been thinking about in terms of my work, in case it helps us, first, bring it closer home to something I’m applying this to, and second, help us see if there’s a way to bring it back to creative work.

When I am writing books, for every word I write in a book, there’s probably 10 to 20 words I’ve written in wasted drafts, but there’s probably 200 words, or more, 500 words, that I’ve captured in notes that are very valuable but are never seeing the light of day, because they’re only helping me improve, only helping me get to the output. Over the past 15 years, 16 years now, I’ve captured everything I’ve read, every thought I’ve had, every idea I’ve connected. I’ve captured them in a tool called Workflowy, which is sort of like something before Notion and Roam came in.

It was a way to organize your ideas and do it in a slightly hierarchical but flexible way. I curated that over the years. Every day I would sit on it, put in what I was reading, put in what I was thinking, connecting those ideas. Every so often, when I was in a curatorial mood, I would go into it and move ideas around based on how I thought things connected. Every year, at the end of the year, I would take a week off to just play with the Workflowy for the year and see how it connected with previous years and so on. So that was just me geeking out on something I enjoy doing anyway.

So far, I’ve not been able to do anything with it, but now I’ve been thinking, why should I be looking only at the book? I should be looking at all these ideas that have been there at the back end. So what I’ve done is taken all of that and created a knowledge graph that links all of those ideas and concepts together. Now that the underlying knowledge graph has been created, it’s really powerful, because it can tell me which conceptual gaps the ideas have, because I just never read that. So it’s able to identify what I should be looking at next. It’s able to identify what’s unique about that contribution, and it’s able to show it to me.

For my curation on whether a certain thing should be added to the knowledge graph or not, I can take the same knowledge graph and run an entire case study of something happening in a certain industry through it. It calibrates the knowledge graph to say these concepts are playing out in this format, in this timeframe, in this industry. I’m having a lot of fun with it, because I’m constantly learning where the gaps in my learning are. It’s also opening a whole range of ways in which what I had previously seen as exhaust and waste, and had never seen the light of day, all of that is being converted into a knowledge graph that can be converted into something usable and productizable and interesting for different stakeholders downstream.

So that’s the way I’ve been thinking about it. If you think of the creative process, or the production process in any knowledge work for that matter, the value of that, corresponding to the learning architecture, lies in these learning iterations that lie scattered all over the place, not in the finalized output. I’ve always felt that the finalized output was more of slicing and dicing and providing a certain narrative. But the narrative is only one way of bringing together all those ideas. So if I take back my unbundling-rebundling thesis, the narrative of the book is a bundle. If you unbundle it, there are many concepts, and they can be rebundled in many ways.

But because the book has a certain constraint that forces that narrative, whether it’s attention span or storytelling, that constraint prevented many other components from entering that bundle. So how do you then reorganize all of those components? That’s where a knowledge graph, which can then be transformed into many different products, becomes even more interesting. So that’s been my way of thinking about it. This is something I always think about in terms of where my own work is going. But in general, I think some version of this applies to the knowledge economy and knowledge work in general.

Jim O’Shaughnessy

Again, listeners and viewers are going to get bored, because we’re just going to agree on everything. I think you are absolutely right. The repurposing of, the analogy I use is, what was left on the cutting room floor.

Sangeet Paul Choudary

Correct.

Jim O’Shaughnessy

And I am a prodigious note-taker. For many years over the last 45, it’s been by hand. But we’re digitizing all of this, and some of the things I’m seeing are, I would have never, even though it’s in my own notes, I would have never thought about it in this particular new combination. And it is, for me at least, incredibly exciting and indeed incredibly generative. Because the AI’s ability to go in and say, dude, you’ve been saying the same thing for the last 45 years, how come you never acted on that? That jives with your ability. You can recombine, and then whole new product lines, whole new ideas, whole new books, whole new ways of learning come out of that.

Sangeet Paul Choudary

Exactly.

Jim O’Shaughnessy

But let’s, okay, so we’re both very lucky in that we have the ability to have access. We have our own hardware installation, our own multimodal AI. At OSV, you obviously have access to all of the frontier models. You probably have your own bespoke models as well. What advice can we give to the listener out there who doesn’t have the total access, but some access? How can they start to change their own path? Especially, I’m thinking of younger people. I think the days of “I’m going to go get my degree in X, Y, or Z” are painfully antiquated. What would your advice be? I’ll hire you for a second here as a consultant to our younger listeners. Where would you point them to be able to maximize their ability to thrive in this new economy?

Sangeet Paul Choudary

Okay, so I think the larger question here has different answers when you think about a younger audience versus people like me who are in their 40s, or even people who are in their 30s, who have had a certain run which gives them, not so much a buffer to experiment with, but more importantly, it has helped them cultivate judgment. It has helped them understand what good looks like. And it has helped them see what output to outcome looks like, because even though you don’t measure the outcome, you sort of know the outcome you’re looking for and you tacitly understand it, so you fine-tune the output to get there. I want to come to the younger part, but to the...

Jim O’Shaughnessy

Actually, you know what, you’re going to the right place. Start with the people like yourself who are in their 40s, or even 50s. They have this long history that they’ve habituated in themselves.

Sangeet Paul Choudary

Right.

Jim O’Shaughnessy

And they’re going to need to be able to change that. So let’s address those folks first, but then get to the younger people who might not have to avoid all the bad habits that we’ve developed.

Sangeet Paul Choudary

Absolutely. There are two very different scenarios between the two. There are people who have been through it. I think the biggest thing to unlearn is that they were told a story, then they saw that story play out, and they now believe in that story. That’s what the youngsters don’t have to worry about to the same extent. They had to worry about a lot of things, but not this. The youngsters already don’t believe in the story they have been told, because they’re seeing it’s not working. But those who have been through some sort of career for 10, 15, 20, 25 years, they were told the story, they saw the story play out, they thought they’d figured out the rules of the game, and now they’re seeing the game change.

So the first thing is that everybody wants to believe the game is changing for others, but not for themselves. That there’s something special about what they’re doing, and not just about what they’re doing, but about how they mastered the game, and that it cannot be taken away from them. I think that is one of the first challenges that anybody with experience has. I’ve gone through that cycle as well, thinking I’ve mastered a certain game, and now, even if AI can do certain things, I should just keep getting better at my game.

It takes a lot of unlearning and questioning, some level of shock to your system, and a lot of reflection for you to come to a point where you realize that, well, it’s all good if the game is not changing and if I’m special, but shouldn’t I be preparing for the reality where the game is changing and I’m not special? And if that doesn’t come through, that’s fine, it was just insurance money. But I should be preparing for that so I’m not caught unawares. So that flip does not necessarily happen for everyone. It happens in different ways for different people.

Some people might realize they’ve sort of come to the end of the road of the previous game, and then realize it’s just not worth moving toward a new game. They’re at a place where they want to stop playing games. That’s possible. Another group might be: we’ve come to the end of the road, but you know what, I can see four more years of playing this game, and I’m going to double down and make as much as I can playing this game, and I’m going to stop after that. So those are very viable scenarios, and those are the classic board-level gotchas.

Every time I speak to a board, the underlying question in the room is: I’m 65 or 75 or whatever, and I’m going to be around in this board seat for three more years and in any board for five more years. Should I really care about AI, if you don’t know when your specific prediction is going to play out? Yes, it’s going to play out, but is it two years or 10 years? So should I then care about it? All those are very viable responses as well.

But if you’re somebody who has taken pride in their craft, if you’re somebody who’s always tried to improve at their game because of your internal ambition and to see the results of that ambition, and you’re not just trying to stay in the game just to stay in the game, I think you should take a hard look at what the new game that’s going to be played is. You should just assume the game is going to change. If you really care about your work, if you really care about getting better and doing better, you should fundamentally assume that everything you know is going to be taken away, and you have to rethink what that is going to look like.

Maybe it’s going to happen in two years, maybe in five years, but instead of betting on the timeline, I would just bet on the outcome, and figure out how to make the most of the lag period while betting on the outcome. So that’s how I would think about people in their 40s, 30s, whatever. Unlearn what you felt you knew. Get over the fact that you felt you had figured out the game and that your game will not change, because it’s actually going to change. Get over that and start afresh.

For the youngsters, I think it’s a lot more challenging. And here I’ll say it’s not just those who are young, but anybody who’s been structurally locked out of an upwardly mobile knowledge economy career and who’s been constantly trying to work their way back into it, whether they got kicked out of a job and entered the services industry, or became an Uber driver or whatever, and they now see that path being locked out even more.

So in general, people who are getting into what would traditionally have been called an upward graph of a knowledge work career, and especially those who are young, won’t necessarily have the on-ramp that allows them to build judgment, because the friction of working with an untrained human in certain cases will be too high compared to the lack of friction of working with a sufficiently trained, highly trained AI. Because of that, firms are going to make choices where they simply don’t go down a path where they need it. So a lot of those on-ramps that helped you fine-tune your judgment, that helped you learn from people who had judgment, all of that goes away. So it’s very easy to say AI will do the execution, humans will retain judgment.

But while there are many issues with that, the bigger issue is who will have that judgment. There’s going to be a significant portion of humanity who might not even be allowed the opportunity to develop that judgment and hence have a unique edge. I don’t have very good advice to give to people who are young. I think the younger you are, the better off you are in a way, because you’re learning that this is happening. I think the transition generation, which went into college in 2020, was stuck at home instead of being at university because of COVID, and then came out of COVID to see ChatGPT launch.

I think that transition generation has it most difficult in a way, because they’ve been told a certain story, they’ve worked their first 12 years of schooling toward getting into that story, and suddenly they’ve seen that whole story break apart. I think if you’re much earlier on, it’s an important time for both students and their parents to realize that the traditional way of optimizing for outputs, optimizing for measurement of output, which is what the education system is based on, is not sufficient. You have to figure out a way to constantly create your own learning architecture, and the only way you can do that is through small experiments, through being entrepreneurial, through gathering feedback.

The answer, again, is not as simplistic as: hard skills are going away, soft skills are important, specialists are not going to be important, generalists are going to be important. This is how we try to bucket solutions, but it’s not quite as binary as that. The only thing we can be entirely sure about is that if you have an iterative, learning-based approach toward your work, if you assume uncertainty as the constant, what that means is you have to have an aim on where things are headed, place a bet on that, think in terms of placing that bet, and constantly update your model of where things are headed based on what you’re learning on a daily basis. That’s the only way you can build your own learning architecture.

You have to constantly assume that where you play is uncertain. It’s not going to be the same as it is today, so you have to bet on that. I would say that’s something that’s true for everybody in jobs as well. Today your company is dealing with uncertainty. Everybody has a view on where AI is taking things, and again, it’s not just AI, it’s many forces. But in the midst of uncertainty, you can’t look at your company as the unit that’s going to guide you on the way forward. You have to bet, you have to learn, and you have to give that learning back to the company to signal that you’ve got it figured out even better than they have.

I think that whole flip, from “I’m going to rely on somebody else to guide my career” versus “I’m going to be at the frontier of betting and learning what’s happening, so that everybody else who’s confronted with uncertainty can see that I’m one step ahead,” I think that flip is going to be really important. So I know I didn’t answer the youngster question really well. It’s a very difficult question. But I believe there’s some version of this that applies at every level, where you have to unlearn the old game, just assume that at some point it’s going to go away from you, and then get comfortable with betting on uncertainty, running experiments, and, based on your learning, constantly changing your roadmap of what you’re betting on and how you’re getting there.

Jim O’Shaughnessy

The thing that is ironic is that, in order to become a great success in the new world, you have to select against the basic coding of the human OS. In other words, what’s one of our biggest biases? Confirmation bias. We seek information that proves, in quotes, that we are right, where we should be seeking information that proves or suggests we are wrong. And high agency versus low agency: expecting tutelage and a coach who’s been through the game to be able to help you is kind of a norm. And yet what you are articulating, and I think correctly articulating, is that we’re going to have to learn to try to unlearn these deeply embedded biases in ourselves. When you were talking about the person who thinks, my game is A-plus and everything else, I’m the exception.

I used to have a GIF that I would put up on Twitter to people who were saying something like that. I said, “This must be your screensaver.” And it was a thing that says, “You are the only exception.” I know that I am not the only exception. I know that I am just as fallible and just as outdated and everything. But it took a lot of time for me to habituate this self-interrogation. For you to be able to continue to iterate and succeed, you have to be able to exit an old mental model. That is really easy to say and it is really difficult to do. So I definitely agree with you that the younger people, honestly, they’re going to be native to this environment, and so they probably will excel.

We have some young, as you know, we do the fellowships every year. And oh my God, the brilliance that is out there among people who are still teenagers. You can literally see it in the way they construct their proposals. They are intuitively doing many of the things you are advocating. Whereas people, well, certainly people of my age, a lot of people who are in their 60s, are like, yeah, I have no incentive to be involved in that. Like your board member. I’m only here another three years. So their incentives are to either be reticent or even to actively push back. Whereas the younger people have no such incentives, and they’re doing fine.

I think you nailed it with the people who really need the advice you just gave, which is people who are already successful in their careers. They got successful in a certain way, you would say, by focusing on the outputs as opposed to the outcomes, inputs, excuse me. But that itself would be incredibly useful. Just that conversation would be incredibly useful, because one of my worries that I’ve expressed repeatedly is there is going to be a cohort of people who, through, and I underline this part, no fault of their own, are just not calibrated or designed for this new world. And I would love to come up with a way where we can do everything possible as a society to ameliorate, to in some way make that blow land less hard.

Because you see all the back-and-forth right now. I did not anticipate the anti-AI response. Well, I did a little bit from the old hierarchical guard, that’s kind of a given. But from younger people as well. Because it’s like, whoa, all the rules are changing, and now you want me to change. And unlearning is hard. The ability to unlearn, I think, is much more important, really, than the ability to learn and then habituate. You’ve got to constantly be unlearning. All models are wrong, some are useful. If you take that attitude, you can switch models relatively easily. You can iterate, you can change. How, in your career, have you changed? I mean, in AI time, your book was published in 2025, that’s decades ago in AI time. How has your own outlook and your own process changed from when you actually published the book to now?

Sangeet Paul Choudary

Well, there are a few different points here. One is that when I wrote the book, I wanted it to be timeless in terms of concepts, if not in examples, because I knew it would not be timeless in examples if I wrote it based on 2025 AI. So I rely a lot on historical analogies and so on. First, over the past year, I’ve tried to constantly calibrate those concepts and see if, with everything that’s happening, those concepts play out reliably. It’s helped me fine-tune where it applies and where it does not apply. It’s leading to an updated version, an updated edition this year, which will talk about things with a lot more nuance.

The first-order effect of that was just that I would have to launch an updated version of the book much faster than I normally would. But then that would be the same output fallacy, right? Because that would mean the faster AI moves, the faster I need to keep writing books, and that’s not going to work. What I’ve tried to do with this new edition, which I’m still working on, is that before I write anything, and this is not why I built the knowledge graph, but now that I’ve built the knowledge graph, I’ve actually calibrated the book through the knowledge graph to see where it’s consistent with what the knowledge graph would predict and where it’s not.

The fun of having this knowledge graph for me is that on a daily basis I’m seeing exactly what you talked about, things that I’ve talked about in the past, things I’ve curated in the past, but where I’m not seeing a certain connection. I’ve seen those connections on a daily basis. Some of them get me excited, so I want to dig down further. So it’s sort of curiosity on steroids. If you’re naturally curious, then having this, it’s one thing to have an LLM that’s constantly finding interesting stuff your way, but you don’t always want that.

For me, the way the knowledge graph has transformed the way I work is that I can just wake up in the morning and ask it to throw me three surprising things, or something that appears a lot in my work but that I’ve not connected to something that appears very little in my work, or it helps me see a lot of gaps in my own conceptual frame. The reason I like it is that I want to keep thinking, and I want to use AI to help me keep thinking even better. When I think, the gaps are very often that I waste time trying to figure out unknowns.

What the knowledge graph helps me do, because it’s structured around knowing what I already know, is that it has pre-scored concepts where I’ve done a lot of my work. It’s able to identify unknowns that are just at the level of the right delta, that stretch me a little bit to connect a well-known concept to an unknown concept, to see it happen in a fundamentally different industry, to connect an unconnected historical precedent to it. So I’ve created it as a way to help me think, which I don’t think I get with an LLM. Because what happens with an LLM is I start with a question, it gives me responses, and in sifting through those responses I learn how to ask better questions. But it’s a very tedious way of learning how to think.

At the end of a long session, I may come out of it having learned something new, but because it doesn’t know what I already know, it doesn’t know how my mind is structured, it’s not able to push me in the right way to increase my thinking. So it may sound a little theoretical as I say it, but only after having created that knowledge graph did I realize how important this idea of identifying the unknowns becomes. The second thing, take away AI and all of these things, one of the things that has really liberated me ever since I decided that my previous game is not going to be worth playing anymore and there’s going to be a fundamentally new game, is that it set me free to rethink things.

If I’m going to find a new game from scratch, I cannot optimize it around anything except longevity and fun. It should be something that is organically fun for me, something I have the incentive and the interest to keep playing long enough. Hence it cannot be optimized around a well-structured game, which was very much optimized around certain markers of success that the game led to. So here, if I don’t know those things beforehand, the only way to keep winning is to stay in the game and keep changing with the game. That has set me free, because if I start with, is it fun, is it something I want to continue doing rather than keep getting burnt out, it helps me take a different approach to my work.

One of the positive outcomes of having to rethink your game has been that the only way you can play a game in a constantly changing playing field, which is what AI and other things are doing to us today, is to ensure you’re in the game long enough and that you’re enjoying playing it. So there are two ways I can respond to what’s happening. I can say I want to play the old game to its maximum for as long as it works, or I want to reinvent myself toward the new game. If I’m doing that, I might as well play it for the next 20, 30 years. In order to do that, I should have fun while doing it.

So what all of this has forced me to think about is, if I’m rethinking what it means to be somebody who has traditionally used, say, books and certain very specific forms of narrative to address this overall point of how things are changing around us, how should industries think about this change, how should companies think about strategy, that overarching question that has always guided my work, which is how does technological change force companies and individuals to rethink how they should compete, if that question continues to be of interest, I would rather create the surrounding infrastructure that helps me stay focused on answering that question, if it’s still relevant, and do it in a way that I continue to enjoy for the long term. So, long story short, the key thing I believe has been really refreshing about having to just stop and forget what I was doing in the past, and the thing I’m doing, is that it gives me the opportunity to build it fun-first, joy-first, rather than speed-first or accuracy-first, all of which actually impose a lot of overheads. I think if I can keep focused on that and the underlying capabilities keep improving, then the notion of scale would also change. You should be in a position where, if you are a fun-first or joy-first company or person or career, you will have the ability, as the underlying capabilities improve, to keep scaling your impact with that. So that’s the way I think about it.

The temptation always is to get faster at what I’m doing today, but I think that just traps you in playing a game that’s going to end soon.

Jim O’Shaughnessy

That’s one of the things I’ve been so excited about, literally because of all these journals. I have been waiting for AI since I was 22 years old in 1982, because the possibility space, learning new things, recombining things, to me that’s incredibly fun and invigorating, and, as you would put it, joyful. I think that the old idea of the nine-to-five job, the whole structure of the way our economy works, is going to change, and I personally think it’s not going to be easy. So I’m not Pollyannish or Panglossian about the whole thing. There’s going to be a lot of disruption, and that’s kind of a given in any kind of transformational technology.

If you can look at it the way you’ve just articulated, I think you’re going to have a much easier go of it than if you’re a type that really believes something because that’s the way it’s always been done here. Because you’re not going to survive in the new environment, right?

Sangeet Paul Choudary

Yeah. I know there’s a certain level of privilege associated with building a fun-first career with constant learning and constant experiments, because we have to think about that alongside this whole point of how there’s growing wealth concentration, there’s growing opportunity polarization, and things of that sort. So that is the context within which it would apply to many people. But the one thing that remains immutable to a large extent is that if you just focus on the fact that the old game is going away, and you either get mad about that or you figure out how to play it better or play it faster, that’s a clear path toward irrelevance.

So given every set of constraints that you personally have, you have to figure out how to get to the new game. Everybody will have their own set of constraints. Some will start from a place of more privilege than others, and that’s to some extent how things have always been. But the one thing I think is going to be common to everyone is that if you keep simply focusing on playing the old game, you’re not going to get to a win that’s going to be significant, because winning the wrong game is actually losing.

Jim O’Shaughnessy

Yeah. So if I were to summarize, it would be: you’ve got to relearn, unlearn. Because so many of us have habituated ways of doing things that we’re not even aware of them.

Sangeet Paul Choudary

Right.

Jim O’Shaughnessy

And I’ve undertaken a series of new projects, one of which is writing my first fiction book. And boy, when I was starting, I’ve written four non-fiction books, and the correlation between fiction and non-fiction I found is basically zero. So I’ve had to learn it, but it’s been really fun to learn how to do it. And I couldn’t have learned as quickly as I learned without AI. I did the traditional thing and read some books on how to write fiction, and I even read a couple about how to write a screenplay. Then I watched some YouTube videos, and I’m like, I don’t think I’ve learned anything at all. So I just went right to our AI platform and started, and then I designed a very mean but very truthful editor that the AI simulated. And it basically came back, “This is horrible, this is awful.”

But it’s interesting, because it’s a whole different conversation. It’s easier to take that advice from a machine than from another person, because from another person I actually experienced it. The first thing I ever wrote for publication, my wife graduated summa cum laude with a degree in journalism, and I was the editor of my high school newspaper. I thought, oh, I know how to write all this stuff. So I wrote it and said, hey, would you take a look at this? This is back in the 90s. I actually handed her the paper that I wrote, and it came back a sea of red. And I got mad, and it became, how can you say this to me, and all of that. I was recounting it with her. And by the way, she was entirely right.

All of her edits made it a vastly better piece of writing. But the point is, we were chatting about it, and I said, so I modeled you into the AI, and they’re wicked mean to me, but I don’t take it personally. And I just think that your underlying factors of curiosity, the joy of experimenting, and the ability to understand that everything’s an iteration, you’re not going to get the hole-in-one every time on the golf course. It seems like selecting for those, again, is selecting against things that we’ve tried to beat out of children in the previous era. Like what was much of public education in the 19th and 20th century?

But no, installing a correct-answer machine in the brain and driving curiosity and all of that kind of stuff out, because your society wanted you to follow orders. Society wanted you to be able to understand those orders and then execute them. So I definitely think this touches not only business, not only society, but the way we learn. And I think it’s interesting to me, because I think we have to be open to every conceivable permutation here. Most of them won’t work, but we’ll learn from what doesn’t work. Your knowledge graph is a great example. It isn’t the large language model that is really giving you all of these super new ideas, it’s your knowledge graph. And people sometimes forget that part of it.

Who knows, maybe at some point in the future AI will get creative and will get all of those things. I have no idea, and I lack the expertise to even comment on whether that is possible. But for now, that isn’t the way it works. It’s a tool. It’s a tool in the hands of a deeply curious person who is comfortable with uncertainty, the best tool that’s ever been invented, certainly in my lifetime. It’s hard for me to articulate how excited I am by it, because it really leads to a whole new paradigm. How do you deal, because you’re dealing with external institutions, and I don’t have that friction, how do you overcome a very deeply skeptical board? Back to the board. Where the CEO answers to the board, and the board is likely made up of people close to my age whose incentives are very different, as you pointed out. Three years and out. How do you convince them, you really have got to take this seriously?

Sangeet Paul Choudary

Yeah. There are quite a few things there. And I want to reiterate the summary you brought in, which brings together a lot of the points we’ve been talking about. It’s a combination of uncertainty in the playing field, with constantly changing and ever-improving capabilities that are available at your disposal, that allows you to innovate in the center and manage that uncertainty to your advantage. That is what the new game is. The difference between a business and an individual is that an individual has emotional constraints and capacity constraints at a different level. That’s why fun-centric becomes very important. But for a business as well, you have to think about what your constraints are, within which you can operate. You have to know that what you’re really going for is, there’s uncertainty outside.

There’s a new capability set internally that creates the opportunity for you, within the unique constraints of your business, within whatever identity you have created for yourself, first, to potentially question that identity, but second, within those constraints, and I wouldn’t say within those constraints, but in cognizance of those constraints, to think about how you can leverage these capabilities to do something fundamentally new, to create a fundamentally new way to compete in the playing field you define. In general, my point to any of these so-called skeptical boards is, by default there’s a certain filter in terms of what comes my way.

So I don’t necessarily speak to a company that’s at step zero. It’s typically to companies at step four out of five, where they’ve kind of done the adoption, they’ve tried to accelerate things internally, they’ve bought into the hype but not seen the results, and then they’ve realized that what I’m talking about is how to change that game, how to think about strategy in a fundamentally different way. So I don’t necessarily have to go in and tell them that AI is important. They sort of know that, everybody’s talking about it, they’ve seen the value internally. They just haven’t yet figured out what that means for them in terms of whether they should continue doing what they’re doing or fundamentally flip.

So that is where I essentially make the case that you can place a bet on the fact that things are not going to change externally. You’re going to have better capability, you’re already adopting it, so you’re going to improve how you do what you do today. But you have to start placing bets on what if things change externally. And to place those bets, you have to start by saying, what are those scenarios? At the end of it, you could come back and say, it’s not going to happen in my relevant timeline, and that’s perfectly fine, because the difference between having a view on what’s going to happen and betting on it is the risk you are willing to take against the timeline.

So it’s a perfectly valid statement to come back and say, I’m not willing to place that bet, because I don’t believe in that timeline. You’re accepting that risk, and that’s fine. That’s how allocation works in general. But you have to do the hard work of thinking through what all those scenarios are, and what your firm looks like in those scenarios. And be very cognizant of the fact that you have to place those bets. You cannot place those bets by omission, the fact that you did not place them because you did not run the scenarios. So you have to do that. At the end of it, if you still believe it’s not going to play out, that’s just the best bet you’ve placed.

There are going to be many situations where companies optimistically, proactively place bets and they don’t play out. And there are going to be situations where companies do not place bets even after seeing the scenarios. But not placing bets because you didn’t do the hard work of seeing the scenarios, didn’t do the hard work of projecting what’s going to happen, didn’t think through how these shifts are playing out, that is the failure case. Because if you do the hard work of developing the scenarios and placing the bets, you’ve already taken some steps to say this is going to happen, that’s not going to happen.

Which means you’ve already perked your sensors to keep sensing whether those bets are going to play out, which means you’ve already started fine-tuning a learning architecture and a feedback loop to see if that’s going to happen. With that, you’ll keep tweaking your scenarios, you’ll keep tweaking your bets. But if you never did that, you would just be an ostrich with your head in the ground, not thinking about what’s going to happen. And so there is no architecture, no feedback loop, nothing created. So that’s what’s important. It’s less about “be the fast mover, do this, do that.” It’s okay to not be the fast mover if that’s deliberate, but it’s not okay to not be the fast mover if that happens out of omission.

Jim O’Shaughnessy

Yeah. And again, our alignment on how we look at this is strikingly similar. Spending a lot of time thinking about failure modes is, in my opinion, not only required but incredibly instructive. Because if you’re a naturally optimistic person, you might have a hard time thinking about all the ways things could go wrong. And the other thing AI can do is simulate cognitive diversity. I’m constantly playing with coming up with the most pessimistic model I can possibly design, but making it very smart. And what’s really interesting when you do that is your blind spots are revealed. We all have blind spots, every single one of us. Having this kind of red-teaming of our own ideas, I just think that is such a valuable thing to have.

And yet a lot of people look at me like I have three heads when I’m like, no, you’ve got to think about all the, not only that, you’ve got to give it to an intelligence that is going to find those blind spots that you have. So, well, listen, I always love talking to you and admire your work. You’re working on the new version of the book that comes out when? Later this year. Perfect. I would love to have you back on again when that comes out, because a topic we didn’t even touch is, what is going to happen to books, your books in particular? Are we going to move to a new way of packaging a book so that it can be constantly updated, so that it can be interrogated?

I think all of those things are going to be super useful, and I would love your view on them.

Sangeet Paul Choudary

Yeah, absolutely, I would love to. It’s a topic I’m constantly thinking about. I would encourage whoever is listening to go to reshufflebook.com. It’s the companion site to the book, where what I’ve tried to do is extract the concepts from the book and show them as a navigable graph, so you can see which concept connects to what and work on applying that. I’ve tried to create different narratives, all of which are again generated by the knowledge graph, because once you map all the concepts, it generates different narratives. So for different personas, whether you’re thinking about it in terms of jobs or in terms of how you design the workforce and the organization, there are different tracks in which you can go through the book.

So that’s one attempt to think about how you unbundle and rebundle the book in new forms. But the larger thing I’m really going for, and I’ll just throw it out here and would love to discuss this again, is that the book was not an optimal bundle for a lot of things it was used for. It was just forced on a lot of formats. What I mean is that I still believe a big idea with a persuasive narrative requires a book. It cannot be done with questions to an LLM, where everybody’s going to get a different version of the idea in a different narrative.

But a lot of how-to advice, which has so far been packaged in a book, is much better accessed in the context of your work in an LLM and so on. So we’ll have to really rethink the relationship between the jobs we wanted to do and the formats that were forcing those jobs on us. There’s a lot of discussion there, and I look forward to that topic.

Jim O’Shaughnessy

Yeah, the user interface is going to change, there’s no doubt about that. Sangeet, always a pleasure talking to you. As you might recall, our final question here is: we make you emperor of the world. You can’t kill anyone, and you can’t put anyone in a re-education camp against their will. But what we can do is hand you a magic microphone, and you can say two things into it. And those two things are going to incept the entire population of the world. They’re going to wake up whenever their morning is, and they’re going to think the two things you say now were their own ideas. And they’re going to say, unlike all the other times where I had these ideas, shower ideas or waking-up ideas, I’m going to act on these two. What are you going to incept in the world’s population?

Sangeet Paul Choudary

Assuming that these ideas can be personalized by the individual, I would want to create the drive for every individual to figure out what they are insanely curious about, which they would want to do just for the love of doing it, which they would want to think about just for the love of thinking about it. I think what a lot of us are lacking is that by outsourcing a lot of our thinking, we are not seeing the incentive for getting into training our thinking machine, our brain. So creating an organic incentive mechanism for that, which is why I said it would be personalized. Everybody wakes up figuring out, here’s what I’m insanely curious about, I’m going to start figuring out how to go after this, and here’s how I’m going to.

At the same time, I would want everyone to think about it as, if I’m so curious about this, I want to do it as long as I can. So how can I do it in a way that I create the conditions for me to constantly think about it? Because if my conditions don’t support this kind of curiosity, and if I’m constrained in other ways to do things that are more short-term, that comes in the way of doing it. So I don’t know if that answers the question directly, but that’s great. Leave that with people.

Jim O’Shaughnessy

The way I would rephrase it is, we’re incepting everyone to wake up thinking, I am insanely curious about this, how can I go about satisfying that curiosity, and sustaining it, and building it into something I can continue to do. Okay, so that’s your first one. What’s your second?

Sangeet Paul Choudary

I think the second piece is the sustaining part, in terms of how you sustain it. It’s about being very clear that you don’t simply, it’s easy to be curious about something, it’s very difficult to sustain it. And in order to sustain something, it’s not just about the fun, but about having the discipline to sustain it. So yes, it’s important to find what you’re insanely curious about, but you should be disciplined enough, you should care about your curiosity so much, that in order to protect it and do it on an ongoing basis, you create the discipline and the conditions around it that can help sustain it. So the second piece is really about getting to that point where you know this is not just a passion, it’s a discipline. And how do you bring those two things together.

Jim O’Shaughnessy

I love them both. What’s the old saying about curiosity being the cure for boredom, and there is no cure for curiosity? Sangeet, thank you so much for your time and your ideas, and I can’t wait for our next conversation.

Sangeet Paul Choudary

I look forward to it. It’s been such a pleasure. Thank you once again.

Leave a comment

Subscribe now

Share

Jameson explains why fiction is a compressed human experience rather than mere entertainment, how the story of Hercules at the crossroads guides his decisions under pressure, and why training montages give us the wrong idea about how slow and monotonous real change actually is. They also discuss main character syndrome versus narcissism, the pull of tribalism, what separates heroes from villains and anti-heroes like Walter White, and how William James clawed his way out of a breakdown by choosing to act as if his choices mattered.

We’ve shared some highlights below, together with links & a full transcript. If you like what you hear/read, please leave a comment or drop us a review on your provider of choice.

Links

Apple Podcasts

Highlights

What Training Montages Get Wrong

Liberty: You wrote about the danger of training montages. What do they get wrong about transformation?

Jameson: Yeah, that’s a fun thing for me with this pursuit. I can look at things in stories, or in storytelling formats, and then look at them through this lens of protagonism. One thing I thought was funny is that these training montages are effective at conveying to a moviegoer that they put in so much work, and we’re compressing it into 60 seconds of visual cues. Rocky, or whoever it is, he’s been grinding.

Liberty: The Karate Kid, waxing cars.

Jameson: But it’s dangerous for us to be exposed to that, because it makes it seem like it’s not as big a deal as it really is. Let’s take the Rocky example. It shows him working out, especially in Rocky IV, working out in the snow, pulling logs, whatever, and it’ll show one scene of him drinking raw eggs. It shows a variety of things. But what it doesn’t show is him doing that every single day, for months.

Liberty: And years of grinding.

Jameson: And even when he’s sick, having to do stuff that’s just miserable. So it makes the idea of a training arc glamorous, because it’s only showing you 60 seconds’ worth. Whereas the reality of any training arc in real life is that I’m signing up for a suffer-fest, and what I just watched in that training montage are literally the highlights of it, the best moments. But the truth is that there are times in life where you need something like that. You need to buckle down and say, yeah, I’m going to remove distractions for this period in my life if I really want to achieve this thing. There were a few other things in the article, but the biggest one is just the idea that it doesn’t show how monotonous and boring it is to actually achieve something that great.

Liberty: That’s the counterproductive aspect of this, because it’s fun to watch. But if it sets your expectations so that you think, oh yeah, it’s going to feel so satisfying and I’m going to see the progress, it’s almost like a time-lapse. It compresses time so much that it gives you the wrong impression of how slow real progress is, and how not fun it is as you’re doing it a lot of the time. So if you come in expecting that and you start training and you don’t see much progress, it feels crap. You may stop, if you come in with the wrong expectations. It could actually do the opposite of what you’d think going in.

Jameson: Yeah. It makes you get really frustrated really quickly when you’re not seeing a similar level of change, or you’re bumping into way more obstacles than you thought you would. What I’d love to see is a training montage that shows the person eating their Tupperware of chicken and rice while everyone around them is eating pizza. Just show that scene dozens of times, that would be a more accurate representation of a training montage. Or show them having to wake up to the 5am alarm day after day and dragging themselves out of bed. We don’t need to see the log-pulling or the deadlifting of 500 pounds, because again, those are the highlights. Show me the true lowlights of what this journey is, if you want me to have a more realistic expectation of what it’s like.

NPCs and Tribalism

Liberty: What are the signs that someone is living like an NPC? How could someone realize their own NPC tendencies? How do you fight that? And what are your own NPC tendencies that you’ve discovered and dealt with, to bring that to your own story arc?

Jameson: So one of the ideas about an NPC that I think is very interesting, because it translates to real life pretty well, is that if you find an NPC, most games are only going to program a few lines of dialogue for it. If you keep going back, they’ll end up repeating the same line, because they don’t have more in the tank to share with you. That translates to real life in the sense that an NPC is more likely to be running off of only a few scripts, and they’re not open to new information. They’ve just decided, this is life, I’m 25 years old, I’ve figured out life. And they spend the next 50 years assuming they have a grasp on the entirety of truth and that everyone who disagrees with them is wrong. An important aspect of living a fulfilling life is being open to new information at any given time. It doesn’t matter if you’re old. In fact, one lesson I took away from Dracula is that you have Van Helsing, who is the most educated, the most learned character, and yet he’s the one having to tell the other characters, I need you to open your mind, I need you to consider things you have thought impossible your entire life. So being able to constantly take in new information, and not letting that turn you into someone who thinks they know everything, is a crucial detail of being able to pursue the life of a protagonist, in my opinion. An NPC is incapable of that, because it’s just easier to run on fewer scripts and say, no, I’ve experienced enough to say this is what life is.

Liberty: And if you don’t think for yourself and create your own scripts, there are plenty of people out there who will be very happy to supply you with a script that helps them. Consumerism, politicians, whatever. There’s always someone else who is very happy to tell you how to think if you don’t do it for yourself.

Jameson: Exactly. And that brings up something I did not assume at all when I started this project. It’s been amazing to me how much, as I’m analyzing stories and lessons, this idea has come up: the idea of tribalism, and how it’s ingrained in us. We are all part of tribes, even in the 21st century. You’re part of your political tribe, your cultural tribe, your religious tribe, your neighborhood tribe, whatever group you identify with. The purpose of the tribe in ancient times was, we survive better when there’s more of us together, but we have to make sure the only ones with us are ones we can trust. That’s why, for a long time, being ostracized from the tribe was basically a death sentence, because you wouldn’t have access to their resources. So even though we have grocery stores now, and I can get access to food without some tribe granting it to me, there are still definite needs filled by tribal instincts, social needs, things like that.

I just witness how often people’s choices are dictated by the need to make sure they can maintain membership in a certain tribe. Tying this back to NPCs, part of it is that it is exhausting to actually think through how you feel about every single thing. It is a monotonous and terrifying task to actually think, no, I’m going to decide for myself.

Liberty: And if you’re wrong, so you’re wrong. It’s not someone else’s fault.

Jameson: So it’s easier to just adopt a belief system from a tribe and say, if Democrats think this way, then that’s how I feel. Or if Republicans feel this way. Or, trying to think of others.

Liberty: My family, my whatever.

Jameson: Yeah, exactly. It can be as granular as my family. Whatever tribe you’re part of, if they believe this, it’s easier to just say, okay, I guess I believe this too. And you cling to the parts that actually resonate with you, and you bury the ones that don’t under a rug and say, well, I agree enough that it’s better for me to just say I’m part of this group, and bury the things that are actually friction points for me. So to me, an NPC is someone who has largely found two or three tribes that they outsource all of their thinking to, and they say, okay, if that’s what they believe, then great, that’s who I am.

Transcript

Liberty

Hello, everyone. I’m not Jim O’Shaughnessy, I’m Liberty. Jim is writing a new book, and while he was knocking it out, I snuck into the studio and decided to record this conversation about what we can learn from fiction and fictional characters, because I could use more of that in my life. I think we could all use more of that wisdom. I used to read about 95% fiction growing up, but sometime in my 20s it flipped, and now I’m 90% nonfiction. But I miss it. So who better to talk about this with than my friend Jameson Olsen? He’s building the school of protagonism based on these ideas. It’s a life philosophy built from the mechanics of great stories, and his podcast, Becoming the Main Character, is case studies in that. He’s trying to combine the entertainment of those stories with the learning and growth, drawing on Lord of the Rings, Sherlock Holmes, Moby-Dick, Dostoevsky, Project Hail Mary. Very varied, but the central thesis is always that fiction is not just entertainment, it’s a compressed human experience. Jameson, welcome to the show.

Jameson

Hey, Liberty, it’s great to be here.

Liberty

Maybe we can begin like a good story, at the beginning. Could you tell us a bit about yourself? The Jameson origin story. Why did you need protagonism? How did you arrive at this?

Jameson

That’s a great way to start. Like a lot of people, I found myself years past college graduation, feeling like life wasn’t going where I thought it would be at that point. Until you graduate college, you’re basically told exactly what step to take. As long as you’re getting the grades and hitting the benchmarks you need to make, you just know you’re doing fine. Then you enter the real world and things can go a little differently. So I had a period, a big chunk of my 20s, where I was living a pretty small existence in terms of what I was doing. My career was moving forward, but not nearly as quickly as I thought it would.

In the meantime, I was consuming a lot of self-help content and personal development. I got into philosophy. That was the first time I started reading some of the ancients. So I was feeding my brain all these ideas, and that was all layered on top of my love of stories from the beginning of my life. I’m the youngest of four siblings, and my older brother was the problem child, if you want to call it that. By most standards he really wasn’t even that problematic, but out of the four of us, he was.

Liberty

It’s all relative.

Jameson

Exactly. He’s such a social butterfly that my parents were conditioned to think, to punish him, we send him to his room. That was torture for him, not being able to interact with people. So after him, they just figured, send James to his room. If he’s being bad, put him in there. Problem was, that’s where my Legos were. They were basically condemning me to go into my own little world. I had all the pirate sets. This is before the IP Legos came out, like Harry Potter and Star Wars. It was just the pirates or the others.

Liberty

You had to use your own imagination.

Jameson

And so it started young. I’ve always been very interested in understanding what makes a great story great and what makes others fall flat. Why do you forget some movies as you’re walking out of the theater, whereas others you think about for days after you see them? During that period of my 20s, most of that effort of understanding stories came through film analysis, watching video essayists on YouTube, reading books here and there.

Liberty

If I did my research correctly, you were much more of a film buff and only started reading classic literature when you started your podcast. Is that true?

Jameson

It is. I think that also works to my advantage, because I bring enthusiasm to my episodes, since I’ve just read the book for the first time. But I’ve never claimed to be a trained expert on the classics, because I hadn’t spent that much time reading fiction until the last three to four years. I just watched movies. It’s beginner’s mind, which is perfect. You sit down, turn it on and consume, whereas a book takes effort. So it was a transition, but the opportunity came along, this idea of a podcast to talk about the greatest stories ever written. And I couldn’t go down that road without infusing it with, marrying, my two greatest interests, which are: what makes a good story good, and how can I find a better, more fulfilling existence in my own personal life? It was the fusion of those two things. It was the combination of the years spent reading personal development books and studying philosophy with the years of watching movies and analyzing why the great ones work. So I set my sights on bringing the classics to 21st-century consumption habits through a podcast.

Liberty

I’m curious, because we can have the inverse. I used to be all fiction and moved into nonfiction. You were probably more into nonfiction. What surprised you most when you dove really deep into these great stories? What was your expectation going in, and did it match, or was it something else?

Jameson

I don’t know if I really had severe expectations either way. But one thing I’ve noticed is that I used to carry the pragmatic view that a lot of people who only read nonfiction have: I get real value from nonfiction, whereas fiction is just entertainment.

Liberty

It can’t be profound because it’s fun, right? As if those things are opposed.

Jameson

One thing that surprised me was realizing that my anxiety levels were higher reading nonfiction, because it put more on my plate of “this is what I should be doing” or “this is what I need to fix about myself.” I’d leave with great ideas, but basically I’d leave with homework. Whereas with fiction, partly because it’s more entertaining to consume a narrative, but also because you read about these situations and think, it could be worse, my life’s not so bad. That was one thing I wasn’t expecting to piece together, that reading nonfiction is incredible and necessary. That’s one thing I should get straight right off the bat. I am never taking the stance that fiction is better than nonfiction. I think both are essential to a well-balanced life. I still read a lot of nonfiction now, but most of it these days is less personal development and more narrative theory and understanding how to craft a great story. I think both are essential. And because I’ve been that person, I think there are a lot of people who have boxed out fiction because they think the real value is only in nonfiction, whereas I think both are important.

Liberty

I think the takeaway here is balance. If someone is only reading nonfiction, they can probably get a lot out of even adding a little fiction to the mix. And if someone is only reading fiction, I’d recommend the inverse. Get some nonfiction, some history, some biographies. But both have so much to contribute. I’m curious, because we all have favorites. Is there a fictional character that has changed the most how you think about your life, that has had the biggest impact? Or maybe even someone you first judged, like, that guy’s an asshole, and then later understood better and could get more out of?

Jameson

I’ll share two. The first is the one I resonated with most at a personal level. The second doesn’t really fit any of the setups you just shared, but it’s the one I can’t stop thinking about almost two years later. The first one, ironically, was the very first episode I ever did, which was Hamlet. I read Hamlet in high school, and that’s been part of the fun, because so many of the books I cover, someone had to read in high school.

Liberty

Which is the best way of making you not get it and not like it.

Jameson

Exactly. The problem isn’t the literature. The problem is the way you’re forced to see a certain perspective based on your teacher’s perspective. That’s why, when I present my thoughts and lessons from episodes, I’m very clear: this is what I took from it. If you take the same thing, great. But maybe you read it and get something else. That’s where the real value comes, if a story is so well structured that you take what you need from it at that time in your life, and I may take something slightly different. So, rereading Hamlet as an adult, on my own terms, and for anyone with Shakespeare, I do think it’s very much worth having a side by side of the original with a more modernized version. I was using a service called LitCharts for that, which is basically CliffsNotes on steroids. For the most part they have these massive PDF files of analysis of a book, but they have a whole part of their website that’s Shakespeare with side by sides, where they highlight in different colors exactly which text they’re interpreting with the modern version. That helped me see it more deeply.

I resonated a lot with Hamlet and his overthinking tendencies. That’s always been something I struggle with. I used to frame it in my personal narrative, to use a term that’s used to describe someone like Hamlet, as my hamartia, the Greek idea of your tragic flaw, which is also tied to your greatest strength. I used to try to frame that as, yeah, there are downsides to it, but because I’m an overthinker, there are also these upsides.

Liberty

You talked yourself into thinking overthinking was great.

Jameson

Luckily, in recent times I’ve been challenging that notion. Why do I have to justify that there are strengths to this? Why can’t I look at how to remove it and maintain the strength anyway? In particular, the scene that sits with me so much from Hamlet is, I think it’s act four, and I believe it’s scene four of act four. It’s when he’s traveling and Fortinbras, the Norwegian prince, is marching through with an army of 20,000 men or so, and Hamlet is marveling at the realization that this is an equal to me. We’re both princes of these nations, and here he is leading 20,000 men to fight for a scrap of land that’s not even worth the bodies that will be buried in it from the war. But he’s leading men on this cause, and I have been running around, unable to even stick with one decision I make. How frivolous has my life been? There’s a line where he says something about how, if man is only good to eat and sleep, “he’s no better than a beast.” So Hamlet has really stuck with me at a personal level.

The story I was so surprised by, and think about all the time, was actually Mary Shelley’s Frankenstein. Part of it is because Hollywood has never done it justice. The del Toro one is the best we’ve ever had. It’s better than anything else by a mile. It still makes one little change, that’s classic Hollywood, that I hated.

Liberty

What is it?

Jameson

To me, the beauty of that story is that you have two opposed forces in Frankenstein and his monster. Obviously Victor made choices. He’s responsible for the choices that created the situation, so he’s guilty in a sense. But the beauty of the book is that as soon as the monster wakes up, literally the moment it starts breathing, he’s just, oh no, what have I done, this was a terrible mistake. And he spends the rest of the book trying to grapple with how to live with that. He’s constantly trying to figure out how to stop it. He wants to take responsibility, he just doesn’t know how. Whereas every portrayal makes it seem like he’s running away from his problems, classic white male who causes something, gets chased, and doesn’t want to be responsible. So they paint him as the villain, whereas early Hollywood painted the monster as truly monstrous. We’ve always had one or the other. One of them has to be a villain.

To me, my read on the book, and of course there are a lot of theories, because Mary Shelley was descended from one of the original feminists, so the story has ties to themes of feminism. And again, I’m not here to say definitively. In fact, that’s one of my biggest pet peeves, people who say definitively that a story is about this one thing. Maybe for you it is.

Liberty

It can be many things at the same time.

Jameson

To me, the beauty of Frankenstein is that you have these two opposed forces. You have the innocence of the monster. It’s crazy, when you’ve grown up with the idea of him being this big, slow, lurching guy with bolts in his neck, and then you realize in the book he’s actually like a zombie-looking Captain America. He’s physically formidable, he’s fast, he’s super strong. He’s kind of a superhero, because Victor used all the best parts to build him. So he’s got all that, and he’s got the tenderness. I basically describe him as if you put a three-year-old in the body of that creature, because he’s sweet and innocent, but when he’s hurt or when he doesn’t understand what’s going on, he lashes out. And that is terrifying when he’s as big as he is.

Then you have Victor, who made the choices that created the situation, so he’s responsible, but he’s trying to figure out what to do. It’s the two of them butting heads, and they cannot coexist. That tension is something so unique to me. For me, the takeaway of the book is the double-edged sword of ambition. Victor wanted to do something great, but because he became obsessive about it, he basically wasn’t in control of his actions, because he was consumed by this need to do something incredible. In the same way, Jurassic Park’s biggest moral is that if you’re so consumed with whether you can, you may end up making a huge mistake that you shouldn’t have made. So, because early Hollywood was so simplified, oh, he creates a monster and the monster terrorizes everybody, to realize how much depth and room there is to explore moral complexities in that book really took me off guard. It’s one of my favorites to this day.

Liberty

That’s great. I need to read it. I’ve actually never read that book, and you’re selling it very well. Let’s get deeper into what protagonism is. I love that name, by the way. What is it? And what is it most likely to be misunderstood as by someone who just hears about it? Someone could be hearing this and thinking, oh yeah, main character syndrome. How is that different from narcissism, thinking the whole world revolves around you and you’re the main character? Explain what it is and what it isn’t.

Jameson

I’m glad you bring that up, because main character syndrome, or main character energy, are terms I hate, because they bring these assumptions of people who lack self-awareness, who are narcissistic, who don’t care about anybody but themselves. To that I say, show me a story where that is actually the case, where the main character acts like that. There’s another disclaimer I should put in: I’m not claiming all fiction is incredible, there’s a lot of trash out there. But of a story that resonates deeply with a human experience, and for me that’s most classics, because that’s why they’ve survived where other books didn’t. They resonated on a very deep level with people. So show me a main character who is supposed to be a heroic figure from any of these books who acts like that. That is literally not what a main character does. But it is interesting how the term main character brings this assumption of egoism into things.

When you look at stories, the hero is always somebody who starts from a much more humble or collectivist place. They’re doing something for other people, or they’re just trying to improve themselves. That’s much more accurate of what a main character does. One of the best parts in Lord of the Rings, which the movies cover but change, and I think they’re both good, so I’m not here to dog on it and say the movie version is bad, is near the end of The Two Towers, the speech Samwise gives to Frodo about the heroes from the great tales. He says that when he was younger, he used to think the heroes were the people who wanted adventure, who were seeking after it. And now he knows the heroes are the ones who didn’t choose to end up in the places where they were, but who just decided to keep going. There are plenty of other stories that exist, but because the people gave up, we never hear about them. The ones we hear about are only the ones who kept going. That’s such a beautiful way to frame it, in my opinion. The heroes, the people we uphold as the ones we want to emulate, are not people who acted brashly or disregarded others. They were the ones trying to improve themselves, trying to improve or protect other people. And they were willing to undergo a lot of sacrifice or transformation to do that.

So for me, protagonism. First of all, it’s still very new, and that’s part of the fun. I’m building a school of philosophy as I go. Some people may hear this and think, who is this guy to think he can build a school of philosophy? And I’d say, you’re right. But also, who could stop me? You can tell me you don’t agree with my ideas, but there’s no benchmark of having to hold certain degrees to start a school of philosophy. It all comes down to, do your ideas stick? Do your ideas hold truth in them? It’s just been a very fun way to frame what I’m trying to state or prove.

So, protagonism, and who it’s for is where I’ll start. It’s for people like me, first and foremost, the people who think they’ve got more in the tank, wherever they’re at in life. They think, I am capable of more, but I feel stuck. I don’t know why I’m not where I thought I’d be. I don’t know how to get traction in the direction I want to go. Because when I was coming up with these ideas at the beginning, most of the stuff I saw online went into one of two extremes. Either it was very much a victim mentality, other people are the problem, it’s not fair, other people have to change so I have a fair chance. Or it was the other extreme, the hustle-porn, alpha culture of just do it, like David Goggins. And the thing is, I like to consume some of that content sometimes, because it gets you going.

Liberty

It’s useful, but it’s not enough.

Jameson

It wasn’t actually doing it for me either. So I thought, I need a system for improvement that’s more centrist than either of those, and it’s more about recognizing that it’s on you. The whole “nobody’s coming to save you” idea.

Liberty

Yep.

Jameson

No one else is ever going to make you the main character in their story. At best, you’ll be a side character. So if you really want a fulfilling life, it’s up to you. It’s about taking ownership, accepting that a level of agency is required to get a satisfying life, but then also doing it in a way that accepts you’re probably not Superman. You’re not going to be able to flip a switch and all of a sudden your life is completely different. It’s going to be a journey, a narrative of the ups and downs to get from where you are to where you want to be. People in those extremes may resonate with what I talk about, but I’m not making it for them. So if I ever have some alpha bro who’s just like, I don’t approve of your lesson, you should just whatever, that’s cool, I’m not talking to you. That’s fine.

The actual approach, as you alluded to in the intro, is that my theory is that the same rules authors, screenwriters, any storytellers use to create a great character for a great story can transfer over to how you visualize and execute your life. And my theory, which there’s no way I can just prove now, it’s more an exploration, is that the reason those became the rules for great storytelling is because they represent the greatest and most resonant truths that humans have discovered about a good, fulfilling life over millennia. Because otherwise we wouldn’t care about the movies that use those rules, or read the books that use them. It’s the same reason we put down bad stories now. They don’t connect with us enough, because there’s not enough truth buried in there.

Liberty

This reminds me of something I’ve long believed, that in great fiction you can smuggle in wisdom and lessons that would not stick if they were stated directly. We remember a good story way better than a PowerPoint slide with the lessons as bullets on it. Charlie Munger used to have this anecdote about the shoe button complex. A guy made a fortune during the war selling shoe buttons, and he was so successful at that one thing that it made him believe he was now an authority on everything else, because he was so great at that. You understand the principle as he’s telling the story, but you remember the story, and the payload is in the story. Our brains evolved to sit around the campfire telling each other stories and heroic poems. That’s how ideas and wisdom have always been communicated. And now, nonfiction may be great, but if you look at the best nonfiction, self-help, Morgan Housel, whatever, it’s full of stories. It’s almost like trying to use the same infrastructure. So we may as well go back to the original, or at least use it well.

Jameson

Yeah. Humans are wired for story. There’s no two ways of looking at it. There’s a reason we don’t find cave paintings of Excel sheets. It’s just how we make sense of things. The irony to me is that even the people who claim, I don’t care about stories, I don’t watch movies, whatever, you’re still living a narrative. Your narrative just isn’t as rooted in traditional stories. It’s more, look at Elon Musk, I want to emulate him. You’re picking a real figure and you want to emulate their story. You’re still using stories as the framework, because we just can’t help it.

Liberty

Ironically, you may actually know more about a character in fiction, because you can hear them thinking. You can know everything that goes into a decision. You can live the consequences. You have the whole epilogue, and you can learn from all of it. While in real life, you only have what people will show you. People can fake it, people can lie. When things go badly, they disappear, and you never know it went wrong. You only see the highlights on Instagram. So, ironically, real life is often faker and more curated than fiction, which can show you more.

Jameson

That’s a great point. There are studies that have shown people who read fiction rank higher in empathy. Even for me personally, there are a lot of people who don’t love the idea of empathy, because it feels soft.

Liberty

You’re so weak.

Jameson

Because I talk about it in The Hound of the Baskervilles, which I know is one of your favorite episodes of my podcast, I distinguished that there’s actually what’s called cognitive empathy, which is the ability to understand how someone else thinks differently from you, and to understand why they think differently, without you going to the level of emotionally sympathizing with them. That’s why Sherlock is an empath, which sounds ridiculous if you think of any adaptation of Sherlock Holmes, but he’s a cognitive empath. He’s incredible at understanding, this person, because of their situation growing up and because of their personality, is going to think this way and make this type of choice, but he doesn’t need to bog himself down by feeling what they feel in order to do that.

So there’s incredible value to what you said. Whether it’s because other people are wearing masks and aren’t being truthful in real life, or because we really struggle to truly get outside of our own perspective and see things from someone else’s point of view. We just filter what we see them doing through our point of view. That’s how we arrive at, you’re so stupid, why would you do that? It’s because we’re filtering what they’re doing through our mindset, and that just doesn’t work. When I was young, 19 or so, I heard a phrase at a lecture that stuck with me the rest of my life. It’s so simple, but it’s just that “the things people do make sense to them.” So the people you hate, the people you think have completely lost the plot, the fact is, their life experience has led them to a point where that is what makes sense to them. You don’t have to agree with it. You don’t have to say it’s as true as yours. But you have to acknowledge there is truth for them in that action.

Liberty

If someone’s not a total psychopath, a total dark-triad type of person, the rest of us are doing our best and see ourselves as the heroes of our own stories. Even if from the outside it doesn’t make sense, having this cognitive empathy of placing yourself in other people’s shoes is a superpower, because so many people don’t even take the time to learn that skill.

Jameson

Yeah. Whether you want to get better at your relationships with your spouse, your children, or on the far more tactical side, if you want to become a better negotiator, there are all sorts of skills that will improve if you can develop the ability to truly see through other people’s perspectives instead of filtering them through your own. And fiction is great at that, because you’re forced to not only hear the actions of other people, but to get inside their brain and see how the dots connect from the first time you’re introduced to them to why they take the actions they take later. In that way, it’s the only real format for truly getting inside someone.

There are memoirs, where someone you admire who’s a real person is sharing their experience. But again, the question is, is their memory faulty? Are they covering up the real truth and masking it to make themselves seem better in the story? We can’t fully know. Whereas with a fictional character, the author has full reign of what they say. But again, it all comes down to whether we feel it. You read a character and you decide, this feels accurate, or it doesn’t. That’s where it comes down to whether it feels true. We have a BS meter in our head that says, this doesn’t feel right.

Liberty

Very finely tuned by evolution.

Jameson

As long as the character feels truthful in its portrayal, it’s a good enough representation of a different perspective from our own to use as data to consider. One of the ways I frame it is that every story is a simulation in the Matrix. It’s a way of understanding a potential circumstance without having to physically live it yourself, seeing how choices play out and how a choice draws reactions from other characters. That’s one of the other values of consuming stories. It lets you get a better understanding of people in the world without you having to pay the price of experiencing everything yourself.

But to close up this section, we made fun of the fact that they don’t have cave paintings of Excel sheets. But to me, the best truths are ones that have a narrative that the numbers back up. It’s the two of them combined that create the best. One thing I’ve paid attention to in my own life since I started this show is what comes to my mind when I’m in the heat of a moment, when I’m feeling tension, when I’m feeling pressure, when I don’t know what to do. It’s never statistics. It’s never, if I react this way, then 73% of the time that will be favorable. I may internally know that stuff, but that’s not what comes to mind when your reactions are more emotional.

But because I know the story of Hercules at the crossroads, which is one of the best stories about Hercules in all of Greek mythology. If I were to place it in the Disney animated Hercules, this is the scene that takes place right before he starts singing “I Can Go the Distance,” because that’s what this sets up. When he’s a young man, he’s walking towards a crossroads, and he sees a woman coming towards him from each of the paths. On the left side she’s running towards him. The other one is just walking, taking her time. So when he gets to the crossroads, the one who’s running is there first. Her name is Kakia, who in Greek mythology is the goddess of vice, of moral misbehavior. She gets to him first, and she’s gorgeous. She’s wearing fine jewelry, she’s very made up, she’s a smoke show for all intents and purposes. And she’s telling him, come with me, you’ll never have to work again. Life will be nothing but pleasure and enjoyment, and you won’t have to worry about a thing. So he’s taken aback by this promise. By the time Kakia has finished her pitch, Arete, the goddess of virtue, has reached the crossroads. She’s a beautiful woman, but she’s not extremely made up. Her clothes are much more plain, but she holds herself with a certain regalness. So she makes her pitch: I promise you nothing except a life of the fruits of your labors. I cannot promise you that you won’t experience hardship, but I can promise you that what you do experience will be the highest you can. And there’s one line from whatever interpretation I read that stuck with me. She says, “The gods have set a price on every good and noble thing.” Nothing is free. You have to give in order to receive. So whatever Kakia is telling you, that luxury, that lavishness, comes with a cost, which is that you won’t experience meaning.

Liberty

Right.

Jameson

Noble things. And so, ultimately, Hercules chooses to follow Arete, and that’s how he became the hero he became. I share that whole story, because if I find myself in a situation where I’m being offered two paths, one that seems easy and way more lavish, and another that feels like a lot of work but has a lot of potential upside, I’m not going to remember statistics, but I may remember Hercules at the crossroads. All of a sudden that story races through my brain, and it makes the choice a lot easier, because that story rang true with me when I read it. The recall I have of that story in my moments at the crossroads makes it a lot easier to think, of course, this is the path I have to take. There are other situations where a lesson or a quote I took from a book comes to mind in key decision moments, in emotional or stressful situations. Not every book I cover sticks with me that much. I’d have to go back and look at my notes to remember the lessons I took from a certain book. But every few books, there’s one that just hits.

Liberty

And that can be life-changing. One can be enough. The right one at the right moment can alter the course of a whole life.

Jameson

And that’s the same with nonfiction.

Liberty

Right.

Jameson

You’ll read 10 books, and maybe two of them really have any impact on you, but you have to go through them to know which ones will. I’d say that’s the same for fiction as well.

Liberty

And speaking of cognitive empathy, I can hear the listener wonder, okay, that sounds good, but is it about great ambition? Do I need to be a hero to do this, to be a protagonist? Is it about great courage and all that, or can it take other shapes? Can it be a smaller-scale version of that?

Jameson

That’s an incredible question, because it’s one I think about a lot. People I know in my own life have different visions of what our best life looks like, and I see no reason to label one as better than the other. The commonality between them is that they both take intention. Neither will happen by just existing. So whether you want to be the CEO of a billion-dollar company, or some sort of celebrity, or, on the other end, you just want a job that pays the bills and lets you have plenty of time with your family because your ultimate goal is to raise kids you’re proud of, those are both incredible aspirations. I’ve tried to come up with a way to distinguish the two types without one sounding lesser than the other. A type A protagonist versus a type one protagonist. I haven’t come up with terms I feel good about, because if I just say A and B, then everyone thinks B’s not as good.

Liberty

It’s almost like once you’ve picked what you want to do, whatever that is, then these tools can help you live the fullest version of that, the best version, be the best protagonist for that story. But the story itself is for you to choose. And if you try to live someone else’s story and it doesn’t sync up with who you really are, that’s another problem. Having someone else’s ambition sounds great in theory, but you can’t borrow someone’s ambition or someone’s confidence. You have to live your own thing. But then I think these things can help you take that to where it can go.

Jameson

I 100% agree. In fact, one of the foundational principles that came from my studies before I was building this is a concept from Carl Jung, where he talks about the only two things any person needs to be happy. The first is to define your values. Maybe you grew up with a value system from your culture, your religion, your political affiliation. You’ve definitely had values imprinted on you. Some of them will resonate, some probably don’t. So we all need to do the work of actually defining our personal values. They’re nobody else’s. This is what I believe makes a good life. This is what I want from life. Then the second part is living in accordance with those values. That’s all it takes to have a happy life.

Liberty

Easy, right?

Jameson

The problem is that most people never sit down and define their personal values. And even those who do, a lot of them aren’t living up to that expectation. That’s where all the discord, the despair and the lack of satisfaction come from. Either you’re living someone else’s code, or you know what your code is but you keep making choices that violate it. So to me, protagonism is very much rooted in taking control of your story by defining the code you live by. And then the harder part is making sure everyday choices are in line with that. That opens the field wide up in terms of what the end results can be. It doesn’t have to fit one specific type. It doesn’t have to be heroic in the sense of looking at an action hero and thinking, I’ve got to be this macho, Jason Bourne, Ethan Hunt kind of guy.

But one of my favorite books that’s informed the way I talk about protagonism, and I reference it on the podcast all the time, is a book by Donald Miller called Hero on a Journey. It’s one of the only books I’ve come across that does the same thing I’m trying to do, where it uses story principles to map a real life. He talks about how there are villains, victims and heroes, and the similarity they share is that they all experience pain, which is an absolute truth about human life. It doesn’t matter if you’re impoverished in a war-torn nation or born with a silver spoon in your mouth, you will experience pain.

Liberty

The human condition is inescapable.

Jameson

The difference comes in how you respond to pain. A victim feels powerless to do anything about it. They just accept that this is all my life is, unless someone else steps in and takes care of it for me. A villain becomes obsessed with making someone else feel their pain, whether that’s the person they blame for it, or they’re just passing it on to other people. Their whole thing is, I feel pain, others need to feel pain as well. And the hero, the only real difference, is that they decide, I don’t want to feel this pain again, and I don’t want the people I care about to ever have to feel this pain. So I will take on the sacrifice. I will transform into what I need to be to make that happen.

There are so many examples of this story in real life. The parents who grew up pretty impoverished and had a rough life because of it, and they say, I don’t want my kids to live like this. So they work two, three jobs so they can send their kids to college and break that cycle of poverty for their line. That’s an amazing example of a hero saying, this is the pain I felt, I don’t want my kids to have to feel it, I’m going to do whatever it takes to fix that. That’s as much a story of a hero to me as someone who’s actually a war hero, or someone who has created a massive industry benefiting millions of people. The scope is different for everybody, but the same principles are true of everyone. To be heroic, all it takes is saying, this is the pain I feel, I don’t want to feel it again, and I don’t want anyone I care about to have to feel it, so I will take on the responsibility to become the person who stops that pain from happening.

Liberty

That’s a perfect segue, because I want to ask you about what you call the principle of becoming, and how all of this sounds like a verb, a journey. It’s not a destination. One of the main differences between a story in a book and real life is that in the book it’s very clear where the beginning, the middle and the end are. And you know that if the hero is suffering, it’s for something, it means something. In real life, sometimes it’s a lot harder to find a meaning. It’s a lot harder to know where the end is, to have a clear moment where, okay, we’ve won, let’s wrap it up, let’s have the epilogue party, it’s done, we’ve won. Life just keeps going on. So whatever this is, I think it has to be more of a constant thing, a never-ending, infinite game, so to speak. So tell me about this. I think it’s fascinating.

Jameson

Yeah. The principle of becoming is the first and, at this point, the only principle I’ve codified as an official principle of protagonism. It’s just the idea that this isn’t about setting a standard of, I’m trash unless I reach this, that I have to do this or else my life is worthless, because that’s such a burdensome way to live. Thinking that I don’t have value unless I do X is a really rough way to live. And the thing is, there’s always going to be great achievers who talk about how that’s how they live, how they lived with constant insecurity. Again, if the hustle-culture people resonate with my stuff, awesome, but I’m not making it for them. I’m making it for the people in the middle who think, I know there’s more in me, but I don’t know how to go about it.

So the principle of becoming is just the idea that you’re approaching life with almost a curiosity above anything else, of just, what am I capable of? If I got rid of a couple of vices that take up a lot of my time and applied that to a couple of hobbies or skills I’m curious about, what could I become? What is the highest version of me that I could achieve? And approaching that with a patient love for yourself, knowing you’re going to trip up, knowing you’re going to make mistakes, but never yielding that curiosity that asks, whether you’re 20 years old or 60, I still have decades left, what can I do with that? What can I achieve? What kind of existence can I create? What kind of legacy can I leave in terms of my descendants? Are they going to look at me and think, all he did was slave away for the man to make a buck? Or are they going to think something else?

Liberty

I love the idea of being a good ancestor. I don’t remember who said it. Maybe Alex Petkas, maybe someone else. But I love looking at your life from the point of view of someone in the future looking back: was that person a good ancestor? That feels a lot healthier as a drive. It comes from a place almost of peace, of aspiration, rather than insecurity of, I set this goal and I’m a failure until I reach it, and the moment I’ve reached it I need to set another goal and be a failure again. I think it’s better to be a vector going in a direction rather than just looking at this point on the line and, in the meantime, feeling bad. I love that.

Jameson

Yeah. The last thing I’ll say about the principle of becoming is that it’s about not living in a deficit where you feel like I am not whole yet until I achieve whatever. It’s about living in a place of contentment: hey, I’m where I’m at because of my choices, for better or worse, but this isn’t the finish line. So if I apply myself a little more, or just focus, it may not be about what skills I can learn at night so I can start a business. It doesn’t have to be something like that. It could be, how can I be more present in my children’s lives? Or how can I be a better contributor to my community? Again, it comes down to you defining what matters to you and what you want out of life, and then having a curiosity you take with you to the grave of, how can I dive a little deeper into this? How can I become a better version of what I think is important in life? There will be seasons where you’re more doggedly attacking that and trying to achieve something, and seasons where you’re resting a bit more, but you’re always thinking about it: what can I do to get a little bit more out of this? Instead of living the life of an NPC, which, for any listeners who aren’t familiar, is a video game term, non-player character, a character that you, as the player, interact with, but they don’t do anything on their own. They’re just there. So to me, the people who aren’t pursuing a protagonism life are kind of NPCs. They’re just clocking in and out of life, because they’re not holding the pen of their story. They’re just, well, this is what life dealt me, so I’ll follow that script. Whereas a protagonist is always curious about what am I capable of becoming if I just am intentional about how I live my life.

Liberty

Yeah, I have a lot more to ask about NPCs. But first I want to ask about something else you wrote about. You wrote about the danger of training montages. What do they get wrong about transformation?

Jameson

Yeah, that’s a fun thing for me with this pursuit. I can look at things in stories, or in storytelling formats, and then look at them through this lens of protagonism. One thing I thought was funny is that these training montages are effective at conveying to a moviegoer that they put in so much work, and we’re compressing it into 60 seconds of visual cues. Rocky, or whoever it is, he’s been grinding.

Liberty

The Karate Kid, waxing cars.

Jameson

But it’s dangerous for us to be exposed to that, because it makes it seem like it’s not as big a deal as it really is. Let’s take the Rocky example. It shows him working out, especially in Rocky IV, working out in the snow, pulling logs, whatever, and it’ll show one scene of him drinking raw eggs. It shows a variety of things. But what it doesn’t show is him doing that every single day, for months.

Liberty

And years of grinding.

Jameson

And even when he’s sick, having to do stuff that’s just miserable. So it makes the idea of a training arc glamorous, because it’s only showing you 60 seconds’ worth. Whereas the reality of any training arc in real life is that I’m signing up for a suffer-fest, and what I just watched in that training montage are literally the highlights of it, the best moments. But the truth is that there are times in life where you need something like that. You need to buckle down and say, yeah, I’m going to remove distractions for this period in my life if I really want to achieve this thing. There were a few other things in the article, but the biggest one is just the idea that it doesn’t show how monotonous and boring it is to actually achieve something that great.

Liberty

That’s the counterproductive aspect of this, because it’s fun to watch. But if it sets your expectations so that you think, oh yeah, it’s going to feel so satisfying and I’m going to see the progress, it’s almost like a time-lapse. It compresses time so much that it gives you the wrong impression of how slow real progress is, and how not fun it is as you’re doing it a lot of the time. So if you come in expecting that and you start training and you don’t see much progress, it feels crap. You may stop, if you come in with the wrong expectations. It could actually do the opposite of what you’d think going in.

Jameson

Yeah. It makes you get really frustrated really quickly when you’re not seeing a similar level of change, or you’re bumping into way more obstacles than you thought you would. What I’d love to see is a training montage that shows the person eating their Tupperware of chicken and rice while everyone around them is eating pizza. Just show that scene dozens of times, that would be a more accurate representation of a training montage. Or show them having to wake up to the 5am alarm day after day and dragging themselves out of bed. We don’t need to see the log-pulling or the deadlifting of 500 pounds, because again, those are the highlights. Show me the true lowlights of what this journey is, if you want me to have a more realistic expectation of what it’s like.

Liberty

And in this world of social media and influencers, people are getting advice from every direction all the time. Tell us about advice with unshared consequences, or why we should be careful with advice from very confident people.

Jameson

So this was a lesson I took from True Grit, which I covered recently. There’s a scene about halfway through the book, so it is a spoiler, but not necessarily a big plot spoiler. They’ve cornered these two outlaws, and in a scuffle Rooster has shot one of them in the leg, and he’s bleeding out. The other outlaw is telling the wounded one not to say anything. Rooster is dangling this in front of him: tell me where your boss is and I’ll get you to a doctor, you won’t die. But the other outlaw is just telling him to can it, don’t say a word. It got me thinking about how it’s easy for him to say don’t talk, because he’s not going to die regardless of the choice. In fact, he benefits more from the other one not talking, because then the boss won’t be angry at him. But this poor kid who was shot is portrayed as maybe 18 or 19 years old. He’s scared and wide-eyed and doesn’t know what he’s gotten into by working with these outlaws. He’s panicking, and he’s impressionable. So when this colleague of his is yelling at him, you shut it, don’t you dare say anything, he’s kind of believing him, even though his life is draining from him as he does it.

That got me thinking about this idea that people will always give you advice, and there are a lot of times when they’re giving you advice that’s only beneficial to them, because they won’t share the consequences of you following it. Unless it’s from a source you completely trust, a mentor, a family member, your oldest friend, if you’re getting advice from someone who isn’t that deeply connected to you, someone you trust implicitly, you have to think through what their motivations are. What do they get out of me following the advice they’re sharing that might benefit them regardless of what happens to me? Because this world is a tough place, and there are people who will take advantage of you at the drop of a hat if it means them getting what they want. So being able to sit back for just a moment and think, okay, why is he telling me to do this, or why does she want me not to do this thing I was talking about? Sometimes you may not come up with anything detrimental, and you think, okay, maybe they just really meant that. But there might be times where you think, oh yeah, they would look really good if I did that, but I’m carrying all the risk for them. It was such a random thought. The actual lesson isn’t connected to any of the main characters in that story, except that one of the main characters shot the kid. But that’s one of the reasons this project has been so fun for me, that the lessons can come out of nowhere. They aren’t necessarily, oh, the main character did this and then that happened, so here’s a lesson. Just inhabiting the world of that story exposes me to thoughts and ideas that I can extrapolate, concepts that are important to think about in modern life.

Liberty

Let’s get back to NPCs. I think this is another great mental model to have. You mentioned it’s from video games, but I think before that it was from role-playing games like Dungeons and Dragons.

Jameson

That’s true.

Liberty

You get to some inn somewhere and there’s a bunch of people there, but they’re all NPCs. They’re not fully fleshed out. They’re just there for a small purpose. They’re not actively changing the story. So that’s the way to think about it. How do you transfer that to real life? What are the signs that someone is living like an NPC? How could someone realize their own NPC tendencies? How do you fight that? And what are your own NPC tendencies that you’ve discovered and dealt with, to bring that to your own story arc?

Jameson

So one of the ideas about an NPC that I think is very interesting, because it translates to real life pretty well, is that if you find an NPC, most games are only going to program a few lines of dialogue for it. If you keep going back, they’ll end up repeating the same line, because they don’t have more in the tank to share with you. That translates to real life in the sense that an NPC is more likely to be running off of only a few scripts, and they’re not open to new information. They’ve just decided, this is life, I’m 25 years old, I’ve figured out life. And they spend the next 50 years assuming they have a grasp on the entirety of truth and that everyone who disagrees with them is wrong. An important aspect of living a fulfilling life is being open to new information at any given time. It doesn’t matter if you’re old. In fact, one lesson I took away from Dracula is that you have Van Helsing, who is the most educated, the most learned character, and yet he’s the one having to tell the other characters, I need you to open your mind, I need you to consider things you have thought impossible your entire life. So being able to constantly take in new information, and not letting that turn you into someone who thinks they know everything, is a crucial detail of being able to pursue the life of a protagonist, in my opinion. An NPC is incapable of that, because it’s just easier to run on fewer scripts and say, no, I’ve experienced enough to say this is what life is.

Liberty

And if you don’t think for yourself and create your own scripts, there are plenty of people out there who will be very happy to supply you with a script that helps them. Consumerism, politicians, whatever. There’s always someone else who is very happy to tell you how to think if you don’t do it for yourself.

Jameson

Exactly. And that brings up something I did not assume at all when I started this project. It’s been amazing to me how much, as I’m analyzing stories and lessons, this idea has come up: the idea of tribalism, and how it’s ingrained in us. We are all part of tribes, even in the 21st century. You’re part of your political tribe, your cultural tribe, your religious tribe, your neighborhood tribe, whatever group you identify with. The purpose of the tribe in ancient times was, we survive better when there’s more of us together, but we have to make sure the only ones with us are ones we can trust. That’s why, for a long time, being ostracized from the tribe was basically a death sentence, because you wouldn’t have access to their resources. So even though we have grocery stores now, and I can get access to food without some tribe granting it to me, there are still definite needs filled by tribal instincts, social needs, things like that.

I just witness how often people’s choices are dictated by the need to make sure they can maintain membership in a certain tribe. Tying this back to NPCs, part of it is that it is exhausting to actually think through how you feel about every single thing. It is a monotonous and terrifying task to actually think, no, I’m going to decide for myself.

Liberty

And if you’re wrong, so you’re wrong. It’s not someone else’s fault.

Jameson

So it’s easier to just adopt a belief system from a tribe and say, if Democrats think this way, then that’s how I feel. Or if Republicans feel this way. Or, trying to think of others.

Liberty

My family, my whatever.

Jameson

Yeah, exactly. It can be as granular as my family. Whatever tribe you’re part of, if they believe this, it’s easier to just say, okay, I guess I believe this too. And you cling to the parts that actually resonate with you, and you bury the ones that don’t under a rug and say, well, I agree enough that it’s better for me to just say I’m part of this group, and bury the things that are actually friction points for me. So to me, an NPC is someone who has largely found two or three tribes that they outsource all of their thinking to, and they say, okay, if that’s what they believe, then great, that’s who I am. Because I just want to be a part of the tribe in a way that I can lie low, that I don’t have to worry about tension in my key relationships, and I don’t have to worry about my ability to keep moving forward. That’s easiest done if I just partake in a certain number of tribes and play by their rules.

I’m not saying that’s bad. What I am saying is that you can’t have that mindset and at the same time complain about how you’re not getting what you want out of life, because you’re not living according to what you want or what you believe. So there is a certain amount of isolation that comes with truly pursuing your path. Whether it’s the famous CEOs who talk about their years of no one believing in them, or whatever it is. Tying this again to true storytelling frameworks, the hero’s journey, Joseph Campbell’s, one of the most foundational concepts of what a good story is, one of the first steps is leaving the tribe. It literally is leaving the tribe. You have to separate yourself from the people doing the normal thing in order to go do something extraordinary. So there is a conflict. While I’m not here to say an NPC life is bad, there is an inherent conflict that cannot be avoided between you trying to fit into your tribes perfectly, in a way that doesn’t rub anyone the wrong way, and you actually going out and achieving what you think you’re capable of becoming.

The trick, again using the hero’s journey as an example, is recognizing that if you don’t want to be completely ostracized from the tribe, your journey out has to come back to somehow benefit the tribe in the end, or else they’ll decide he’s a liability, get rid of him. So whether you went and slayed the dragon that was threatening the crops, or whatever it is, the only way to maintain relationships within your tribe but also do your thing is that your journey out has to somehow come back to benefit them. Maybe your family is very traditional and they don’t like that you want to go off to a big city and have a big career. If you do that long enough, they may think, yeah, he’s not really as dialed-in a family member as the rest of us. But if you do it so that you can then come back and elevate the existence of your family members, all of a sudden you’re the hero. All of a sudden you’re the one who makes everyone proud. But there are some people who go out on the journey, achieve the great thing, but don’t make the loop back. And then they wonder why everyone hates them.

Liberty

Yeah. And to be clear, being an NPC, or borrowing ideas and values from the tribe, is not all bad. It’s kind of a floor, because some of these ideas are probably great, and it’s better to have that than nothing. But it’s also a ceiling, because if you do like everybody else, you can’t expect to have outcomes too different from everybody else. But one question about this. The flip side of this mental model is, is there a danger that it could be a little dehumanizing, that you could look down on other people, oh, they’re all NPCs, and I’m not? How do you avoid this turning into something negative, or a bad way of interacting with others?

Jameson

I guess the first thing I’d say is that every belief system comes with the risk of downplaying the other, of categorizing the people who don’t see things the way you do as lesser than. So yeah, I definitely think there are risks with it, but it’s not like other, more traditional ways of thinking aren’t this way too. This is a great question. I haven’t spent a ton of time thinking about this before, but from the thoughts I have had, I guess I’d say that part of the way I try to frame this ties back to the thing I said, that what people do makes sense to them. So if they’re not living as purposeful and particular a life as me, someone who’s trying to pursue greatness in one way or another, that’s because their life experience hasn’t taught them that they’re capable of it, or they genuinely may just not desire it. That’s a huge thing that honestly freed me up in my personal life, just recognizing that if people see the world so differently from me, and they’re not doing something detrimental, they’re not harming other people, that’s an important caveat, then it’s no skin off my nose. I don’t have to hold it against them.

What’s funny is that I’d say I’m actually a very judgmental person, in the sense that I do look at people’s situations and make a judgment on them, but I don’t then carry this extra layer of, and therefore they are bad. I make the judgment, but it’s just saying, oh, that’s what they’re up to, that’s their situation, that’s what they think is important. It may be frustrating if I need something from them that they’re not willing to give because of their worldview. There are definitely situations where I wish they’d see the world a little differently, but it’s accepting that they’re living their story. I can’t control that. They wouldn’t want me to control it for them, the same way I wouldn’t want anyone else writing my story. So you try to elevate, you try to assist where you can, but ultimately your story is the only one you have a modicum of control over. So you should focus on that.

One idea to tie in here, and this connects to several things I’ve said, including coming back around to the tribe at the end of the story, is that I do believe truly heroic figures, in one way or another, are always doing what they do for more than themselves. We like to idolize a lot of people who are truly just out for themselves, at least from the outside, and there’s a lot that’s admirable about what they achieve. They accomplish incredible things. But at the end of the day, we don’t revere them the same way we do people who have sacrificed, who have done a lot for the benefit of others. So I think that’s an important way to evaluate what’s worth pursuing with your protagonist life. What are your goals? Purely to make you rich, or famous, or whatever it is you say you want? Or is it because you have a vision of how you can help other people by achieving these things, so you’re doing it for something bigger than yourself? Not only is that a more harmonic ending to the story if you benefit others, but it can also be the motivation to stick through the hard times, if you know other people are being impacted by your success or your failure.

Whether it’s your family, I try to categorize the main characters I talk about into different clusters. I have this matrix that’s partially the Donald Miller framework I talked about, are they a hero, villain or victim, based on how they respond to their pain. And the thing I added to it is, who does this person care about? The three categories that create this matrix are, first, someone I call a champion, and this is Captain America, someone who thinks everyone is worth protecting, I will put myself on the line for anybody. Then there’s the guardian, who has a select group of people they care about. Maybe that’s their family, maybe their city. It’s Frodo caring about the Shire. The guardian has a certain number of people they care about, whereas the champion is just, I am here to defend everybody, to serve everybody. And then the maverick. I used to keep it on the same level as the other heroes, but I’ve ultimately separated it, because I thought, this is not the same thing. The maverick is someone who’s willing to undergo transformation, but ultimately they only care about themselves. So this isn’t truly heroic, but at the same time these characters do the things heroes do. They make self-sacrifices, the same way you can learn from a villain in certain regards. So they’re worth analyzing, but it’s just worth pointing out that this person only cares about themselves. They are burning bridges left and right. They will ultimately only have themselves, or the people they can pay to be around them, at the end of the day. So it’s worth evaluating, who is it that I care about, and how is that motivating me to go down the path I want to go down, to transform into what I need to be to serve this group of people?

Liberty

Beautiful. As I was thinking about NPCs, it reminded me of something I wrote a while ago, about how there’s an asymmetry there. Because you can’t see into other people’s heads, but you can see into yours, you should treat others and yourself differently. I have different expectations. You should never expect others to change. If they do, that’s great. But you should always remember that you can change, and always try to. You should filter what other people say through the most charitable interpretation, but you should pre-filter everything you say through the least charitable interpretation. I think this asymmetry, if you think about the NPC principle that way, means you should always look for your own NPC tendencies and try to fix them. And if you notice them in others, you should be very charitable with it, and say, it may look like that from the outside, but I can’t know what’s going on inside. I think that’s one way to balance it out.

Jameson

Yeah, that’s a great point. The only layer I’d add is that, to me, there’s a certain layer of, I can’t know for sure their intentions. And even if I had the ability to be positive about their intentions and it is a bad interpretation, so what? As you said, you can’t change them. So a lot of being willing to transform is accepting the truth of your circumstances. If that means you have an unsupportive spouse or unsupportive parents, there’s no need to villainize them to be able to say, this is the reality of my situation, so I have to factor this in. If I want to achieve this thing, I have to assume I’m not going to have the support of these people. That’s just how it is. A big key to being a high-agency person is being willing to 100% accept the reality of where you are. Because it’s only then that you can start making the choices to change that situation.

Liberty

Yeah, looking at hard truths and being lucid about it is part of agency. If you have your head buried in the sand and you pretend everything’s okay, are you going to make the decisions, the sacrifices, that cause change, if you think they’re not needed?

Jameson

Yeah, totally. Because, going back to the start of this conversation, that chunk of my 20s, I was very much, oh, this isn’t fair, my boss isn’t giving me the opportunities I deserve. I was very much playing that victim mentality, that NPC mentality of, it’s out of my hands, so what’s the point? It’s such an unhelpful mindset. You’re asking me what the traits of NPCs are. I think it’s that they have a backpack full of limiting beliefs, things they’ve assumed to be 100% true and 100% unchangeable, whether that’s about themselves. Oh, that’s just the way I am, which is one of the most annoying phrases for me to hear, because that’s the way you have been. There’s nothing that says you have to continue to be this way. So they have limiting beliefs about themselves, or limiting beliefs about the opportunities they can expect to find out in the world. I’ve definitely had my fair share. All of us do. Even people who, if we wanted to, could claim we’re enlightened enough to see that the world is more under our control than we think, we all still carry limiting beliefs that we need to challenge on a regular basis. But there’s a big difference between saying, I have limiting beliefs and so I try to catch myself and work through them when I see them in action, and not recognizing that they are limiting beliefs and instead labeling them as concrete truths you have no say over.

Liberty

Yeah. That’s why it’s a journey. That’s why it’s not a destination. How about villains and anti-heroes? Protagonists are not always good people. Walter White is a protagonist. What separates a hero from a villain with tons of agency? And what about admiring characters for their intensity or their cleverness, rather than their wisdom? How do you think about learning from people you may not want to be like, or wouldn’t want in your life?

Jameson

Yeah, that’s another area where there’s so much more to mine than I’ve had time to so far. I cover a lot of characters who fit into the anti-hero category, or even just very compelling villains. Walter White’s a great example. He’s a perfect example of the Greek term I used earlier, the hamartia, the tragic flaw. At the surface level, people think it literally just means tragic flaw, but the deeper meaning of a hamartia is that your tragic flaw is actually tied to your greatest strength as well. It’s the downside of your greatest strength. Walter White is a great example, because his greatest strength is his genius with chemistry. He’s able to do things that have never been done before, and he creates a product that’s worth more than anything that’s ever been on the market. But that makes him pretty prideful, to the point where he creates unnecessary risk, because he’s unwilling to have his genius go unrecognized. And there are so many Shakespearean characters. Macbeth was very ambitious, and because he didn’t have the value set in place, when opportunities to achieve ambition through shady means came around, he jumped on it, even if it took his wife convincing him to. And that led to his downfall.

So to me, anti-heroes, or villains who had a more promising start, whether we hear about that in the story or it’s just assumed, they’re beautiful ways of doing what I described before, simulations of the Matrix. In fact, I love stories where the hero and the villain have similar origins, because then you can track which choices separated them.

Liberty

Especially if they’re best friends.

Jameson

It really is. So if you have characters, especially in a story where the hero and the villain were on the same side and experienced the same thing. One principle of stories is that there’s always the inciting incident. The first bit of the story establishes the world as it currently is, and then something happens that changes everything. A lot of the time it may be the pain point, the thing that creates the pain that starts them on a journey. So if you have a story where the hero and the villain start on the same side, and then the inciting incident impacts both of them, but it’s their responses that really diverge, that’s a really fascinating case study, in my opinion, because you’re witnessing in real time how you end up on different paths.

So I think they’re very valuable, because they serve as warnings. Especially in old Hollywood and a lot of dime-store novels, which stick to higher-level themes, they simplify the villain by just making them truly evil. They’re mustache-twirling, they just love being evil. They wear black, they only talk disparagingly to everybody under them. So they simplify the villain by giving them no redeeming qualities, which for the most part is not true of real life. Everyone we struggle with or see as a bad person, in our personal lives at least, there’s more to them than that, but we’re just honing in on the things we don’t like or disagree with. So I do love that evolution of Hollywood, where we’re getting more complex villains and seeing the backstory. One of the best examples was the first Black Panther movie, where we see, I can’t remember the character’s name, it’s Michael B. Jordan’s character, but we see his origin, we see the pain that he felt. So even if we think, okay, but you took some really radical choices and ended up on the wrong side of stuff, we at least understand, oh, look, this is where things happened to him that led to him feeling betrayed, that led to him feeling like justice was not done unless he took these actions.

Those stories are really interesting to me, because they serve as way better litmus tests. Okay, where was the key choice that he made to end up on this path? Versus someone like, the one that came to mind is Darth Vader. Well, the prequels actually do show his journey, but if we take just the original trilogy.

Liberty

Yep.

Jameson

Darth Vader is just, I mean, he does redeem himself at the very end, but up until the end of Return of the Jedi, it’s just, I am here to do my master’s bidding, rule the galaxy. So that type is just more flat. A cardboard character is a term I hear, not so much authors, but critics of writers use. Oh, his characters are so flat, they’re made of cardboard. So now, the funny thing is that we have so much of a push to show the depth and complexity of villains that when we get a more traditional one, and at the same time we have to show the flaws of our heroes and elevate them and show how complex they are, which, again, there’s value to it, it’s really important, but it’s funny how we’ve pushed so much in that direction that now, when we get a more straightforward story of just a good guy trying to do the right thing, it feels like a breath of fresh air. You and I recorded, as we’ve discussed, on your podcast, A Knight of the Seven Kingdoms and…

Liberty

Project Hail Mary…

Jameson

Yeah. Where it’s just, oh man, he’s not a perfect being, but his intentions are a hundred percent good. That was my favorite thing about that story, compared to the other things we’ve gotten in the Game of Thrones universe, where we’ve got to have 50 different characters and we’re showing all their motivations, and they’re all corrupt in one way or another.

Liberty

Yeah, exactly.

Jameson

So to me, we need both. You need the complex characters so you can see how you may have been headed in the right direction but slowly start to drift. Speaking of Game of Thrones, Daenerys really impressed me in the mid seasons, where we see her transformation from being this savior of the enslaved, out here to right the wrongs. In her mind, her vision hasn’t changed, she’s still doing the same things, but we see how her choices and her tactics evolve into much more sinister paths. So that’s a great example of the evolution of a villain, or just a character with villainous traits. But at the same time, we need the more pure examples as well, as something aspirational. If we’re only given stories of, oh, everyone’s flawed, then we don’t have the inspiration of, but I could be more than I am. We just think, well, I’ve got good qualities and that’s good enough, I’m going to settle where I’m at, there’s no need. Whereas we have Hercules at the crossroads, and we have these other characters who are fictional but are idealized versions of what a human could be. They give us something to aim for.

In fact, one little fascinating thing for me is the way terms are used to describe things. Fiction. We just naturally assume that means fake, that’s what it means, it’s fake, it’s not real. But several of these terms, their origins aren’t nearly as simple as that. They have a better purpose than just saying, oh, this is not real. Recently I learned that the etymology of “pretend” is actually tied to the idea of stretching forward. It’s about reaching. So to pretend is, okay, this is what we know, but let’s imagine, let’s stretch forward a little bit and visualize what could be.

Liberty

Speaking of stories as simulations.

Jameson

Yeah, exactly. So to me, having the perfect hero characters is something that needs to be in the rotation, because they give us the visual so that we can pretend, we can extend forward our assumptions about ourselves. Okay, but what if I could embody that more than I currently do? What if I could approximate this character more than I am now? How much better off would I be? So the same way I say fiction and nonfiction are both necessary, I think we need the complex stories that show that heroes have flaws and that villains had, at some point in their life, better intentions than they’re showing now. But we also need stories that just give us that gold, that shining star of, how cool would it be if I could become more like this?

Liberty

And as we approach the ending of today’s story, someone who’s been listening to this and it sounds good, but they feel like they’ve been drifting, maybe they’ve been hearing about this NPC stuff and thinking, oh yeah, that’s a little too close to home. What is the first small protagonist move they could make today? What are the small first baby steps towards higher agency? What would you recommend they think about? Or maybe don’t think, just do, and then as you do, you start to integrate it.

Jameson

Yeah. In one of the more recent episodes I covered, one of the takeaways I had was the idea of, don’t try to think your way into becoming. Just start making the choices, and then the becoming is what follows. It’s the same concept as, you don’t learn your way into being brave, you take some courageous actions, and then once you’ve got those in your bag, it’s, okay, I guess I am more courageous. But a specific exercise for people who are as overthinking and neurotic as I am: sit down, preferably with pen and paper, and preferably without any device that could distract you. Just sit down and challenge the assumptions. What do I value based on the tribes I’m a part of, and what are the sticky points of those assumptions of my tribe where maybe I need to make a choice that’s more personal to me? Sit down and decide, what is it I want from life? I feel the pull to be uber-successful and make tons of money, but is that really what I want? Because if you’re just chasing money because you know it’ll give you a more comfortable lifestyle. You know the old proverb of the fisherman, where some guy comes to him and says, you should start a fishing business and keep scaling it, and the fisherman says, why would I do that? And it comes full circle, back to saying, well, if you make all this money and have other people do it, then you can take the day off and just go fishing.

Liberty

Retire and go fishing.

Jameson

So the modern life of social media, which is only projecting these shiny versions of life, the 24-hour news cycle, everything in our existence is working to pressure you into thinking the good life is only a certain selection of pathways, and that may not be true for what you want out of life. So I think the number one thing is that you need to decide, what is it that I think I would be most fulfilled by in life? And if that’s becoming an entrepreneur, awesome. If that’s finding how to retire early so you can spend more time with the people you love, equally awesome. The only thing that matters is that you have decided this is what the best version of your story is, and you take the responsibility to recognize that it’s up to you. I will never be the main character in someone else’s story. I’ve got one shot at this. Just because I’m not there yet, and maybe I’m even in a much worse spot than I thought I would be at this point in my life, it’s never too late to take some control back, if you just grab the pen and start rewriting the script you’re currently living.

It’s not easy. The thing I’ll share, and maybe this is how we wrap up, I’ve talked to you about how I recently discovered William James, and I’ve become obsessed with him. He might be on what I’d call the Mount Rushmore of protagonism. So, the brief concept. William James, interestingly, is the brother of the novelist Henry James. He was an American psychologist from, I believe, the late 19th century into the early 20th century. He had a lot of philosophies that are very in line with protagonism, of agency and deciding what to make of your life. But what makes him so fascinating to me is that he’s not some academic who just wrote about this from a cushy life. He actually had a complete breakdown himself, where he spent years bedridden, questioning existence, sometimes considering ending his life. So he went through it personally. And then one day he just decided, because one of the things he was struggling with was, do I have free will, or is it determinism, am I just destined to do what I do? So he was struggling with these thoughts, and one day he just decided, “You know what? I don’t know which it is, but I’m just going to act like my choices do matter, and if that’s determinism, I don’t care.” I love that, because I’ve literally said that in one of my episodes. You could argue either one. As long as I, in my consciousness today, can look at my options and say, I have the choice to do something I think is a better choice than another, that’s all that matters. It doesn’t matter if I was predetermined to do this or not. All I care about is that in the here and now, I can look at my options and I have the option to choose what I think is going to contribute to a better life.

So, William James decided to do that, and he eventually built himself up into one of these very prominent psychologists and philosophers who had a very meaningful life. The detail I haven’t shared with you yet, that ties into it being a journey, is that I learned about that story, and then I learned there was controversy about it. And I thought, oh no, is the controversy that this never happened, that he never had a breakdown? But no, every source agrees he had a breakdown, he went through it. The controversy comes from the fact that some versions romanticize it, that he had that thought one day and boom, his life was changed. And people are saying that’s not true. The only contention is that they’re saying it took him a while to figure it out. He had that thought, he wrote it down somewhere, but he stumbled his way to what we eventually see him as. When I learned that, I thought, that’s even better.

Liberty

That’s more relatable.

Jameson

That’s a much more relatable story. The whole point is that he got there because he just decided, it doesn’t matter how low I am right now, or where I’m at in life, my choices from here on out matter, and I’m going to live under the assumption that I can impact where I end up based on my choices. Because I will never say, oh, everyone can be billionaires if you just choose. Your circumstances do have certain limitations. But within your fixed circumstances that are truly outside of your capability, there are millions of possibilities of how your life ends up that you do have some sway, some control over, as long as you decide that your choices will impact the way your story plays out.

Liberty

You’ve been dealt a hand of cards. How you play them is what matters. We all have a different hand, but then, what do you do with it?

Jameson

Yeah. I can’t remember the exact phrasing, but for the most pessimistic that someone could be about these ideas, my answer is actually something I’ve thought about, and I was validated by it when Matthew McConaughey was on Hot Ones. He talked about this idea that you have desires, you have these things, and, man, I’m really butchering trying to remember it. I just remember the zinger, the line he said where I thought, yes, this is exactly what I’m trying to say. He just points out that it doesn’t matter how bad things are for you right now, “what else are you gonna do?” Are you going to just sit there and do nothing and be like, well, this is life, I’m just going to survive for the rest of my existence on this planet? Or are you going to say, what can I control, what can I become? I may have robbed myself of certain opportunities because of choices I made 10 years ago. I may have certain limitations purely because of where I was born, my parents’ socioeconomic status. Yeah, but so what? What are you going to do about it? What are you going to try to create with your beautiful life? No matter what hand of cards you’ve been dealt, there are people who have been dealt an almost identical hand who have turned it into something amazing, and there are people who have been dealt an almost identical hand who have just suffered through the rest of their life. And that is the difference between being an NPC and choosing to see your life as a story that you can actually impact with the choices you make.

Liberty

I think that’s as good a place as any to close it. We’re going to put all of your links in the show notes. For people who want more, check out Becoming the Main Character in your podcast player. I’m going to steal Jim’s question. If you could be made emperor of the world, you’re the cosmic writer of the novel of life, and every human is a character in it, and you could incept two things in all those characters, two things that they will believe and act on, what would those two things be? And they can be from what we’ve discussed. What stands out?

Jameson

I would instill that the two most important things any person can have to achieve a meaningful life are curiosity, both about what am I capable of becoming and about why do people act differently than me, being willing to see things outside of yourself. So, curiosity. And then grit, the grit to grind out the vision you have, to actually live the painstaking training montages that are glamorized in 60 seconds in a movie. Those two things combined, the curiosity to explore what’s possible and what you’re capable of, and the ability to stick it out when it’s not fun, when it might feel like it’s not going to work out, but you know that the only way to find out if it works out is to stick with it. Grit and curiosity. I think if people just held those as important virtues, it would be an incredible place to live.

Liberty

I love that. Thank you, everyone. Goodbye.

Leave a comment

Subscribe now

Share

We’ve shared some highlights below, together with links & a full transcript. If you like what you hear/read, please leave a comment or drop us a review on your provider of choice.

Links

Apple Podcasts

Highlights

Interviewing Bernie Madoff

Jimmy Soni: Good timing. Yeah. So fast forward, you know, I have to ask about it and then we’ll get back to books. But you interviewed Bernie Madoff in jail. Tell us the run up to that and how all that happened. So that’s year three of your career.

David Gelles: Yeah, that’s probably year three. So it’s 2011. I remember it was, the story, though, begins my very first week at the FT. So in late 2008, Bernie Madoff gets arrested. And when that happens, I’m in the financial newsroom in London and everyone’s watching the TV and like, oh, my gosh, what is this story? What’s happening? As it’s all going down, I’m literally in my orientation, I get a text from someone I’m close to who says, you’ll never believe who so and so’s uncle is. It’s Bernie Madoff. Which is to say, I had a personal connection, a couple steps removed to the family. And on instinct and with no grounding in credibility, I said, tell them to send him the message that if he ever talks to a reporter, he has to talk to me.

Jimmy Soni: That is audacious. That’s quite bold.

David Gelles: Nothing happened. Fast forward two years. I wake up one morning. I was still in San Francisco at the time. Yes. And I get an email. So it’s 2010 now. And I wake up and there’s an email in my inbox from Butner Correctional Facility, Federal inmate number 123456, Bernard L. Madoff. And he had sent me an email. Wow. And thus began months of correspondence with him where I sort of had to win his trust without compromising myself as a reporter or ceding to his wishes as he asked me to suss things out for him. So I played this very delicate dance. And after a couple attempts, the first of which was denied, to go visit him, I finally got the okay, and myself and Gillian Tett went down to North Carolina and spent these couple hours with him, where initially, I think both of us were on our back feet because it was such a shock to meet him. And he just started telling us his story. And after what felt like an hour, but was probably really only 15 or 20 minutes, we sort of kicked each other under the table and were like, wait, he’s spinning us. And we had to snap out of it and go on offense. And then we had this remarkable conversation.

Jimmy Soni: Wow. So when you got that email from him, did you believe it?

David Gelles: I mean, yeah, because it wasn’t without some basis. I had put in this request via family, and here were the results.

Jimmy Soni: And then the correspondence before you meet him, is it just slice of life stuff? I mean, what are you corresponding about?

David Gelles: He was asking me about how coverage of his case was being portrayed, and he was asking me what I thought of other stories. And so before I replied, I mean, I tried to be not accommodating, but I tried to be conversational and not dismissive or brusque because I wanted to win his trust. But I also checked every word I sent with the lawyers at the Financial Times before I sent it. And so we tried to stay in bounds, and I think we got there.

Jimmy Soni: Yeah. Did you ever find out why he didn’t talk to another reporter?

David Gelles: Well, he did. So I was not the only one. A few months before Gillian and I went in, Diana Henriques from the New York Times went in and had her interview with him, which was on the front page. So she scooped us. It was great. But we got the second one. We’re still proud of it.

Jimmy Soni: Yeah, fast follower is good on the Bernie Madoff in prison interview especially.

David Gelles: I was 30 at the time, so it was a coup.

David’s First Front Page Story

Jimmy Soni: Do you remember the first time you saw your name in print? Is that a moment that you can think back on?

David Gelles: I mean, it would have been those early ones in Student Underground and then the Voice of the Hill, those kind of ones. And I mean, sure, but I don’t think it gave me that rush. The one that gave me the rush came five weeks into J School when literally five weeks after starting graduate school at Berkeley, I had a story on the front page of the New York Times. And that was the one that was like, oh, here we go. And that gave me the full adrenaline rush of breaking big news and understanding what it meant to set the agenda on a big story.

Jimmy Soni: So let’s give listeners context for that story and for the path that led you to it. So tell us about the story and how you managed your way onto the front page of the Times.

David Gelles: Literally, I remember showing up five weeks before this all happened. My editor, my instructor, a woman named Lydia Chavez, pulled me aside and she sort of had to explain to me what a lead was. Yeah, I mean, I didn’t know. I’d never heard of the inverted pyramid. I didn’t know what a nut graph was. I was pretty green. And nevertheless, she took a chance on me and was like, we’ll turn you into a reporter. So fast forward a few weeks. It is October of 2006. I’m in Berkeley, California. I’m up late at night. YouTube has just come out. YouTube’s a thing for the first time. It hasn’t even been acquired by Google yet. That would happen a month or so later. And I’m surfing YouTube just in the scroll, for the first time, letting the algorithm serve me videos, as we all still do today, in ways that have, I think, evolved past what we could have imagined at the time. And I remember the sequence. I remember it was Mavericks, the big wave surfing competition was going off, so there were videos of big wave surfers. I was like, well, that’s cool. And then there was a video of a big wave with a helicopter in the background filming. I was like, oh, that’s cool. Clicked on that. And then there was a military helicopter. And I’m a guy, so I’m like, all right, military helicopter. Click. Top Gun’s my favorite movie. Click. And then it went to fighter jets. I was like, click. And then all of a sudden, there was an Al Qaeda in Iraq insurgent video showing American soldiers getting IED’d and sniped set to jihadist music.

Jimmy Soni: Wow.

David Gelles: And I sobered up really quickly because I was probably a little high. I was in Berkeley. I sobered up really quickly. And my news radar went off. And I was like, what am I looking at? And it was just what I said. And from that, the algorithm started suggesting more and more. And I instinctively, that night, late at night, started cataloging them. I started copying URLs, I started a spreadsheet, and I was like, I’m going to keep track of all this. And I stayed up all night and I found hundreds over the course of the night. I had the usernames of who was uploading them. And I ran to Berkeley J School the next morning. I went to Lydia Chavez, who used to be a bureau chief at the New York Times, and I said, I think I have a real story. I think this is not a journalism school story. I think this is a proper story. A real, real story. And she said, oh, my gosh, yes. Fortuitously, another student in my class, in my little cohort of 12 students, was a man named Omar Fekeiki. Omar had arrived in the United States just five weeks earlier for the first time after having been a fixer for the Washington Post in Baghdad.

Jimmy Soni: Whoa.

David Gelles: Was an Iraqi national. We showed all this to him. He’s like, this is exactly what this is. These are recruiting videos. They sell them at roadside stands on DVDs. The Marines or the army guys probably bought them, brought them home. I then contacted one of the kids who had uploaded them, some kid in Minnesota who found it, uploaded it, and we reported this whole story. Lydia calls the national desk of the New York Times. She explains what we have here. They pair us with another Times reporter who essentially reports all of our work and the story goes on the front page.

Jimmy Soni: Wow. Wow. That’s an unbelievable story.

David Gelles: It was a wild story. And that night, that was still, I mean, the Times can still set the agenda in a big way. But if you think back to this is literally 20 years ago at that moment, whatever led the Times often led the national news television broadcast. I remember turning on CNN that night. And I forget if it was Anderson Cooper, whoever it was, leading with it. And you turn on CBS and they were leading with it. And it was a moment that set the agenda for that moment. And it was this confluence of the war and tech and Google and YouTube. And that was my signal. That was the story where I was like, oh, it feels good to have my name in print on a story like that.

Transcript

Jimmy Soni

I am here with one of my favorite people, David Gelles. Thank you for coming on Infinite Loops.

David Gelles

Thanks for having me.

Jimmy Soni

So you’ve done a lot of different kinds of work, but you are principally a reporter at the New York Times, as well as an author of three wonderful books. We’re going to talk about them today. But I want to turn back the clock a bit and start with how did it become clear to you that you wanted to be in the world of words? This is a very specific kind of world that attracts a certain person with a particular kind of neuroses. How did this become your path?

David Gelles

We have to go all the way back.

Jimmy Soni

All the way back. Rewind all the way back.

David Gelles

We’re talking about middle school or high school here. And I remember the first teacher I had who lit me up with a book. And I remember her name.

Jimmy Soni

What’s her name? Let’s make her famous.

David Gelles

Her name was Laurie Shantis. I’ve even been in touch with her sometime in the last 10 or 15 years. And she was the English teacher at Maybach High School. And I must have been a sophomore. I remember the room this class happened in, and I remember the book. And it was Crime and Punishment.

Jimmy Soni

Oh, wow. That is heady stuff.

David Gelles

It was a great, weird high school I went to, and she was an incredible teacher, and she was the one that made me love the word and what it could do. And so that was my entry into being a deep reader and lover of words. And also a writer. She pushed us to write. And I didn’t have any illusions as a sophomore and a junior in high school that I would somehow be a writer one day. But at least it got the wheels moving. It got the gears turning. And I mean, it’s vivid. I remember when it began, and that was then.

Jimmy Soni

That’s amazing. And did you dabble as a student in newspaper?

David Gelles

Not at all. Not until college. So I went to Boston University. And while at Boston University, they had actually a great student newspaper there, the Free Press. But I think, yeah, Boston University Free Press. I think that’s right. And I had nothing to do with it. Never wrote for it once. Didn’t try. Was oblivious and uninterested. I did, however, work for what was known as the student underground, which was the anarchist newspaper on campus. And in a very formative, I didn’t know, very formative trip. I think I was a sophomore. Yeah, it must have been. As a sophomore, I went on a Students Against Sweatshops junket of sorts to Nicaragua during spring break. And reported on maquiladora factories and lived with sweatshop workers in really brutal conditions in Nicaragua and saw some really tough stuff and came back and wrote about it for the student underground, our radical newspaper at the time. And I’m sure the copy was terrible. I had no idea what I was doing, but it was my first real experience reporting and it made an impact.

Jimmy Soni

That’s amazing. Take me back even before this. Were you an avid reader as a kid? What was your reading life like when you were younger?

David Gelles

I can’t say I was an avid reader. My kids, who are 10 and 12 right now, are truly avid readers. I mean, they read for four to seven hours a day. We have to beg them to stop reading in order to brush their teeth. They’re sort of freaks about it. So I was nothing close to that at that point. They have, literally, I’m thinking, I think they’ve probably read more books already in their lives than I have in the last many years.

Jimmy Soni

Well, hold on. We have to go down the tangent. This doesn’t happen by accident, I mean presumably.

David Gelles

It doesn’t.

Jimmy Soni

How have you engineered this?

David Gelles

We’ll do the parenting section later. But no, I was not an avid reader, but I did grow up in a family, well, in two homes because my parents were split, where there was a lot of writing and reading around. So again, I wasn’t an avid reader like my kids are, but I was always exposed to words. Both my parents were writers themselves. My mother has written several books. My dad was a dance and music critic, including for the New York Times.

Jimmy Soni

So you inherited the family business, sort of.

David Gelles

Yeah. No that’s the Sulzbergers.

Jimmy Soni

That’s true. Fair enough.

David Gelles

But yeah, when I actually go into the New York Times CMS and enter my byline, my father’s name comes up too, as a suggestion.

Jimmy Soni

That’s cool.

David Gelles

Yeah. So I was always around words.

Jimmy Soni

Yeah. I remember when I was really young, not when I was reading serious books, but when I was young and just fooling around, it was, for me, Hatchet by Gary Paulsen, the Encyclopedia Brown series, which I would just tear through, and then the Mossflower and Redwall series by Brian Jacques. And I had this experience of the librarian knew I liked that series so much that when the new copies came in, she would hold them back from other kids and secretly give them to me. And that’s when I knew that reading could be totally engrossing. Did you have those books for yourself at a very young age?

David Gelles

I did at a very young age. I’m trying to remember. I mean, Hatchet is there. And in fact, I was literally looking at Hatchet in my apartment last night with my kids because they have read it at this point. Where the Red Fern Grows, All Quiet on the Western Front was the first one that I remember even before Crime and Punishment, pushing me as a reader and a thinker. I mean, I had blown through all the Hardy Boys, I’d read all the kids’ lit and the Choose Your Own Adventure or whatever it might have been that was age appropriate at the time. But I think the first real memories as a reader, I guess I remember the Lord of the Rings trilogy reading that with my father. But we didn’t have Harry Potter at the time. So I’m just trying to think back to those immersive worlds. And the one that really, even before Crime and Punishment, gives me that visceral sense of being lost was All Quiet. And then fast forward a little bit, just after Crime and Punishment, it was Moby Dick.

Jimmy Soni

Oh, wow. You were really reading some serious stuff in high school. These are the big leagues.

David Gelles

Well, I think there are doctoral dissertations, the shelves groaning under the weight of them. For both those books. And on the Moby Dick front, I had a really unique edition of the book that was the paperback produced by a printing press called Arion Press in San Francisco. Great printing press, run by a family friend. But the thing is this big. I mean, it’s probably a six pound book. And I took it backpacking through Guatemala, Honduras and Belize for three weeks. And everyone thought I was a crazy person because I had this tome that I was trekking around next to my folded up underwear in Ziploc bags. But that was another one. I think so for me, the experience is going really deep in these worlds rather than burning through books at a fast clip.

Jimmy Soni

Yeah. You know, there’s, I wrote columns for the student newspaper. And I remember that at one point a friend of mine was asking, why do this? You’re not compensated for it. And I said, because it’s more thrilling for me to see how people react to that than it is to do my homework. I’ll put more time into a column that’s 750 words for a handful of Duke students than I will into a serious paper that’s determining a grade in a class. Did you have a similar experience writing for the underground newspaper?

David Gelles

I think that at that point that was sort of a one off. And in truth, I probably took the assignment to justify the trip. Again, I wasn’t serious about reporting at the time, didn’t quite know what I was doing. What you’re describing, though, kicked in for me in my early 20s. So a few years after college, I was living in Washington D.C. It was my first real job out of college. I was designing museum exhibitions in Washington D.C. and I sort of got the journalism bug and I started freelancing for really small community newspapers. I am not talking about the Washington City Paper. I remember cold emailing, pitching the City Paper and they sort of laughed me out of the building. They said, go home kid. You don’t know what you’re doing. You don’t have any clips. And so I was writing for true community news. Yeah, it was called the Hill Rag because I lived on Capitol Hill and Voice of the Hill. And I mean, I think we’re talking circulation 2,000. These were pamphlets that they would hand out to support local advertising. But that was where I had that experience of, oh, I’m doing this because I can’t help but do it. And that was a signal to me that I should probably be doing this full time.

Jimmy Soni

Did you, how long did you do that? That’s a very particular kind of...

David Gelles

A year and a half, two years. And again, it wasn’t a full time job. I had my day job, but I was leaving work early to go report on things in the neighborhood because I had the bug. And then during that time I applied to graduate school and went to Berkeley J school starting in 2006.

Jimmy Soni

Got it. Okay. Do you remember the first time you saw your name in print? Is that a moment that you can think back on?

David Gelles

I mean, it would have been those early ones in Student Underground and then the Voice of the Hill, those kind of ones. And I mean, sure, but I don’t think it gave me that rush. The one that gave me the rush came five weeks into J School when literally five weeks after starting graduate school at Berkeley, I had a story on the front page of the New York Times. And that was the one that was like, oh, here we go. And that gave me the full adrenaline rush of breaking big news and understanding what it meant to set the agenda on a big story.

Jimmy Soni

So let’s give listeners context for that story and for the path that led you to it. So tell us about the story and how you managed your way onto the front page of the Times.

David Gelles

Literally, I remember showing up five weeks before this all happened. My editor, my instructor, a woman named Lydia Chavez, pulled me aside and she sort of had to explain to me what a lead was. Yeah, I mean, I didn’t know. I’d never heard of the inverted pyramid. I didn’t know what a nut graph was. I was pretty green. And nevertheless, she took a chance on me and was like, we’ll turn you into a reporter. So fast forward a few weeks. It is October of 2006. I’m in Berkeley, California. I’m up late at night. YouTube has just come out. It’s YouTube’s a thing for the first time. It hasn’t even been acquired by Google yet. That would happen a month or so later. And I’m surfing YouTube just in the scroll, for the first time, letting the algorithm serve me videos, as we all still do today, in ways that have, I think, evolved past what we could have imagined at the time. And I remember the sequence. I remember it was Mavericks, the big wave surfing competition was going off, so there were videos of big wave surfers. I was like, well, that’s cool. And I’m a guy, so I was like, that’s cool. And then there was a video of a big wave with a helicopter in the background filming. I was like, oh, that’s cool. Clicked on that. And then there was a military helicopter. And I’m a guy, so I’m like, all right, military helicopter. Click. Top Gun’s my favorite movie. Click. And then it went to fighter jets. I was like, click. And then all of a sudden, there was an Al Qaeda in Iraq insurgent video showing American soldiers getting IED’d and sniped set to jihadist music.

Jimmy Soni

Wow.

David Gelles

And I sobered up really quickly because I was probably a little high. I was in Berkeley. I sobered up really quickly. And my news radar went off. And I was like, what am I looking at? And it was just what I said. And from that, the algorithm started suggesting more and more. And I instinctively, that night, late at night, started cataloging them. I started copying URLs, I started a spreadsheet, and I was like, I’m going to keep track of all this. And I stayed up all night and I found hundreds over the course of the night. I had the usernames of who was uploading them. And I ran to Berkeley J School the next morning. I went to Lydia Chavez, who used to be a bureau chief at the New York Times, and I said, I think I have a real story. I think this is not a journalism school story. I think this is a proper story. A real, real story. And she said, oh, my gosh, yes. Fortuitously, another student in my class, in my little cohort of 12 students, was a man named Omar Fekeiki. Omar had arrived in the United States just five weeks earlier for the first time after having been a fixer for the Washington Post in Baghdad.

Jimmy Soni

Whoa.

David Gelles

Was an Iraqi national. We showed all this to him. He’s like, this is exactly what this is. These are recruiting videos. They sell them at roadside stands on DVDs. The Marines or the army guys probably bought them, brought them home. I then contacted one of the kids who had uploaded them, some kid in Minnesota who found it, uploaded it, and we reported this whole story. Lydia calls the national desk of the New York Times. She explains what we have here. They pair us with another Times reporter who essentially reports all of our work and the story goes on the front page.

Jimmy Soni

Wow. Wow. That’s an unbelievable story.

David Gelles

It was a wild story. And that night, that was still, I mean, the Times can still set the agenda in a big way. But if you think back to this is literally 20 years ago at that moment, whatever led the Times often led the national news television broadcast. I remember turning on CNN that night. And I forget if it was Anderson Cooper, whoever it was, leading with it. And you turn on CBS and they were leading with it. And it was a moment that set the agenda for that moment. And it was this confluence of the war and tech and Google and YouTube. And that was my signal. That was the story where I was like, oh, it feels good to have my name in print on a story like that.

Jimmy Soni

I mean, that’s, I have so many questions. You’re a student at that point of the craft, and so how do you deal with, I mean, how does regular homework compare to doing that story?

David Gelles

I don’t remember doing homework in J school, but I really just considered myself a freelancer. This is the advice I still give students is just do as much real work as you can. And so when I got to J school, the Times was the big one, but I was freelancing for anyone who would take me. And it was $50 a story, 200 bucks a story, whatever I could get. I wrote for magazines, I wrote for small business journals. I wrote for the Berkeley Daily Planet about trees getting cut down. I was like, whatever practical experience I can get, I’m going to get it. And so that’s how I got through those couple of years.

Jimmy Soni

In the immediate aftermath of that story, you know, it’s sort of like you got up to bat and you had a home run your first time out. How did you, what was your follow up act? Did you stick with that particular story?

David Gelles

No, there was no follow up. I mean, I did probably have homework and other assignments, but I did try to maintain a relationship with the Times and I did keep freelancing. So during my years at J school, I subsequently wrote for the House and Home section when it was still going, for the magazine, for the sports section. I tried to be as good of a freelancer as I could. And then I applied for the New York Times internship in 2007, figuring that with a page one byline that had gone most emailed, I probably had some good shots. I got back a form letter from Sheila Rule that said, “Thank you for your application. We’re going in a different direction.” Yeah, I still have that form letter framed on my desk to this day.

Jimmy Soni

I mean, that’s when you got to keep, yeah, it’s like, that’s amazing. So you get out of J school and what happens after that?

David Gelles

Career wise, get out of J school. I began, I decided to focus on business reporting. While I was in J school, no one else in my class was interested in it. I found it very interesting. I figured if it was about people, not numbers, then there were going to be great stories there. And I sort of had the field to myself. So I did my first summer internship at Forbes magazine and wrote real Forbes stories and also Forbes lists. And then did my second year at Berkeley J school because it was a two year program. Studied long form magazine writing at the time, which was great experience to learn a narrative craft. And then graduated, went to the Miami Herald, joined the business desk and was in Miami for the fall of 2008 for the presidential election. So was doing small business coverage, but also helping with the election coverage, which is an incredible weird thing to be a part of. And also just a last glimpse of a real big daily metro newsroom operating. So that was wonderful. And then very quickly, by December of 2008, had accepted a job in San Francisco with the Financial Times. Initially, as I think I was a digital media correspondent, which meant I was supposed to be doing video and audio stuff, which I had no idea how to do. But I sort of bluffed my way in. They, I got there, they realized I didn’t know what I was doing. They’re like, well, what can you do? And I was like, I can write stories. And they said, well, no one’s covering these things called Twitter and Facebook. Why don’t you be the social media guy? So I started covering social media for the FT in December of 2008, which was again, good timing.

Jimmy Soni

Good timing. Yeah. So fast forward, you know, I have to ask about it and then we’ll get back to books. But you interviewed Bernie Madoff in jail. Tell us the run up to that and how all that happened. So that’s year three of your career.

David Gelles

Yeah, that’s probably year three. So it’s 2011. I remember it was, the story, though, begins my very first week at the FT. So in late 2008, Bernie Madoff gets arrested. And when that happens, I’m in the financial newsroom in London and everyone’s watching the TV and like, oh, my gosh, what is this story? What’s happening? As it’s all going down, I’m literally in my orientation, I get a text from someone I’m close to who says, you’ll never believe who so and so’s uncle is. It’s Bernie Madoff. Which is to say, I had a personal connection, a couple steps removed to the family. And on instinct and with no grounding in credibility, I said, tell them to send him the message that if he ever talks to a reporter, he has to talk to me.

Jimmy Soni

That is audacious. That’s quite bold.

David Gelles

Nothing happened. Fast forward two years. I wake up one morning. I was still in San Francisco at the time. Yes. And I get an email. So it’s 2010 now. And I wake up and there’s an email in my inbox from Butner Correctional Facility, Federal inmate number 123456, Bernard L. Madoff. And he had sent me an email. Wow. And thus began months of correspondence with him where I sort of had to win his trust without compromising myself as a reporter or ceding to his wishes as he asked me to suss things out for him. So I played this very delicate dance. And after a couple attempts, the first of which was denied, to go visit him, I finally got the okay, and myself and Gillian Tett went down to North Carolina and spent these couple hours with him, where initially, I think both of us were on our back feet because it was such a shock to meet him. And he just started telling us his story. And after what felt like an hour, but was probably really only 15 or 20 minutes, we sort of kicked each other under the table and were like, wait, he’s spinning us. And we had to snap out of it and go on offense. And then we had this remarkable conversation.

Jimmy Soni

Wow. So when you got that email from him, did you believe it?

David Gelles

I mean, yeah, because it wasn’t without some basis. I had put in this request via family, and here were the results.

Jimmy Soni

And then the correspondence before you meet him, is it just slice of life stuff? I mean, what are you corresponding about?

David Gelles

He was asking me about how coverage of his case was being portrayed, and he was asking me what I thought of other stories. And so before I replied, I mean, I tried to be not accommodating, but I tried to be conversational and not dismissive or brusque because I wanted to win his trust. But I also checked every word I sent with the lawyers at the Financial Times before I sent it. And so we tried to stay in bounds, and I think we got there.

Jimmy Soni

Yeah. Did you ever find out why he didn’t talk to another reporter?

David Gelles

Well, he did. So I was not the only one. A few months before Gillian and I went in, Diana Henriques from the New York Times went in and had her interview with him, which was on the front page. So she scooped us. It was great. But we got the second one. We’re still proud of it.

Jimmy Soni

Yeah, fast follower is good on the Bernie Madoff in prison interview especially.

David Gelles

I was 30 at the time, so it was a coup.

Jimmy Soni

So at this time in your life, are you thinking in book length form? I mean, one thing about being in newsrooms, you’re always surrounded by words and word people. People are kind of side hustling on books. Did you have designs on writing books back then, or was it really just cutting your teeth in journalism?

David Gelles

Maybe notionally, but I was mostly focused on cutting my teeth. I mean, I came to it pretty late again. It wasn’t on the student newspaper, so I was just trying to find my way in the profession. But what happened was when I met the woman who had become my agent, Binky Urban, who was legendary, she was Gillian Tett’s agent. She was agent of other friends and mentors of mine. I met her at a party and she said, “One day you’re going to have an idea for a book. Call me first.”

Jimmy Soni

Oh, wow. This is your version of the Madoff note.

David Gelles

Not far off. And so fast forward a year or so, right around the time I think I did the Madoff story, I wrote a magazine article for the FT Weekend magazine about companies that were starting to offer meditation in the workplace. And I emailed her that Monday and said, hey, did you see that story? Wonder if there’s a book here. She wrote right back and she said, I saw it. I agree. Let’s go. And that was my first book.

Jimmy Soni

And that became Mindful Work.

David Gelles

That became Mindful Work, which is 11 years old now.

Jimmy Soni

Wow. All right, so take me back, because this is, you know, at Infinite Books, this is our stock and trade, and we spend all this time obsessing about books and ideas. It is one thing to go from to do an article about companies that are out there that are embracing these practices, to graduate that to a book. So you’ve got the agent, you’ve got a thread of an idea, but there’s still a lot of miles to go between that and this book. So what was that like? And spare no detail, because we’ve got a lot of people listening who actually are in this process or might be thinking about this process for themselves. How do you go from, you sent the email to her, did you have in your head that there was a book there? Or is it really just a flyer? You were like, let me try this out.

David Gelles

Oh, no, I think I thought there was a book, something. The voice inside was like, this is something you need to go do. I don’t know that I knew the entirety of it, but probably in the reporting, and this is, I mean, this is probably 13 years ago, because the book came out 11 years ago, so it took me a couple years to get it done. So it was a long time ago. But in the reporting for the magazine article, I think I realized that there was enough. There was a lot more that I was not going to get in the article, which suggested to me, all right, there’s probably other characters, other chapters here. And then I honestly don’t remember a ton about the proposal or how it was structured or what was in it, but it was definitely the case that I sort of used that magazine article as the peg, probably broadened it out. And one thing that’s unusual about Mindful Work, which I don’t necessarily recommend, is that it’s almost like three, I almost inhabit three different voices in the book. There’s a narrative nonfiction sort of conventional reportorial voice. There is a personal autobiographical voice where I tell my own story of my relationship with Buddhism and meditation and mindfulness. And then there’s almost, at times, almost a meditation teacher voice that I inhabit, where I offer some loose instructions on how other people might go about these practices. That’s madness. I don’t recommend it at all. Figuring out how to thread those together was really difficult. And listen, I think we all make mistakes on any big project and hopefully don’t repeat them on our next project. Looking back, that is one of the things I think that makes, listen, I’m proud of the book. It was the right book for me at the right time, but I think it was one of the things that made it a very difficult book to write in some ways for me. And if I’m being honest, probably also may have limited some of the reach or potential because it was like, what kind of a book is this? It was a little hard to say, but that was the first book.

Jimmy Soni

Yeah. Did you enjoy doing it, though? I mean, really take us back. You signed the deal. Did you find your kind of dream editor? How did all that go down?

David Gelles

Yeah. So went out and we had interest from a few different editors. And I vividly remember this. We actually had three different offers on the line. And then Hurricane Sandy hit, and then the entire book publishing industry essentially shut down for six weeks. And when everyone came back, we had one offer, which was great because it was the right author, right editor, and it was Eamon Dolan, who was then at Houghton Mifflin Harcourt. And Eamon was great. And he would go on, he’s been the editor for all three of my books, and he took a real interest, and he did a great job holding my hand through the process of writing this first book. I remember the reporting for this book vividly. And it was really fun to figure out how to report for a book rather than a newspaper article. When I’m reporting for a newspaper article, I am very tactically and almost in a mercenary way looking for those perfect quotes, perfect details because you have so little space. So you get attuned to finding, oh, that’s it. That’s in there. Whereas the canvas is so much larger with a book that I found myself having to recognize that a lot of stuff that in newspaper or even magazine reporting might just end up on the cutting room floor, I was like, no, you need to hold on to that. You need to remember it. And so I actually found that you need to slow down when you’re reporting for books and sort of have a wider aperture and notice things that you might not otherwise notice in a different reporting style. So that was, I remember that. And I did some great reporting trips. I remember the writing being difficult, I think, because I was trying to thread these three different parts and listen, the reception was great. It was not a bestseller. That’s fine. But I still, no lie, I still to this day get notes about it. And I think for anyone who’s written a book that in some ways, beyond the lists, beyond the money, beyond the accolades, that’s the most satisfying. And when I still, to this day, 11 years later, someone reads it for the first time, they’re like, that really helped me. Yeah, well, amen. That’s incredible.

Jimmy Soni

Very brass tacks. You have a full time job doing reporting. How did you balance that with the book work? Especially given that it’s a different style of writing? I mean, this is, all my books have been side hustles. I love that. I actually think it’s important to be engaged in the world in some way and then have things that you’re doing that are longer form projects. I mean, I’m sure there are people, I know there are people who do just the long form stuff all the time. I think I’d go a little stir crazy. What was that like for you, balancing those two commitments?

David Gelles

I remember the reporting, the writing, reporting and writing for the first book, almost all of it happened before we had children. And so I had a little more time then.

Jimmy Soni

You’re like “Pro-tip people: do the first book before…”

David Gelles

I do remember having a bit more free time. I would say two things. Number one, I have a pretty high work metabolism and I also have learned how to be pretty efficient. I’m a fast writer, which really helps when you’re writing books. So I don’t have to rewrite things over and over. Not to say that every sentence that comes out is the final draft, but I write pretty clean, pretty fast copy. Was it a side hustle? Yes. Did I find it insurmountable? Not at all.

Jimmy Soni

Okay. Do you tend to write, do you chunk up your writing when you do it in the day? Do you write in the mornings? What’s your process like?

David Gelles

Before children, I was a night owl, and I would write at night. That’s definitely shifted. It’s harder to write at night. I think for this more recent book, I did most of my writing on vacation or on weekends.

Jimmy Soni

Yeah, got it. So not during the week?

David Gelles

Well, I mean, inevitably, if I could squeeze a little in here and there, but for those dedicated chunks where, and I do find if you’re going to really settle into the prose and into the extended thought processes that I think make great books work, you need extended time without distraction to do that. And so I found that mostly happened not with 90 minutes on lunch break, but with three or four hours with no interruptions.

Jimmy Soni

For each of the books I’ve done, there’s a kind of model book, a book where, whether in the category or just in my head, it kind of sets the standard for what I’m trying to do. And I very consciously make careful studies of these books. I mean, to the point of knowing how many words are in a chapter or figuring out how did the author do this? Because it does, you feel like it’s somewhat impenetrable if you haven’t done it before. This is your first book. So there is a process of learning. You also don’t want to necessarily admit your ignorance to your editor. Not all the time. But did you have templates, models, books you were reading that served as a template for this book?

David Gelles

No. And again, I think, because it was an unusual book for the reasons I already mentioned, I was not prescient enough to sort of look for models or identify them. I think the same was true with my second book as well. There wasn’t an obvious comp because it was such a polemic. Which, in both cases, I probably made things hard for myself.

Jimmy Soni

Right, right. There have been polemics before.

David Gelles

Yeah.

Jimmy Soni

But so then when you’re, take me back to the revision and editorial process for a book at the very end is very different than the metabolism of journalism, than the pace. What was that like for you? Because I, you know, I have to believe that part of what’s nice about the work you do day to day is you put something out in the world, it’s put out quickly. You get feedback quickly, you move on to the next target. Books have five false deadlines. And that’s being conservative. How did you deal with that as a, given you’d grown up in the world of journalism?

David Gelles

I definitely, and I’ve told my team this over the years, when I send an email, I expect a reply back within 24 hours. Even if it’s just them saying, thanks, I’ll give you feedback in two weeks. Fine. But I can’t wait two weeks to get the read receipt. So I had to get better about telling them what I need as an author. And I think that’s something all authors should do is understand what you need to keep your own sanity. Yeah, so that was a part of it. Listen, I like being edited. There’s little I enjoy more than the experience of feeling like someone I trust really got in there with my copy and is actively investing their time and energy and trying to make it better and stress test the arguments and elevate the prose. And so whenever that happens, whether it’s Eamon or some of the other folks who have helped get eyes on my manuscripts over the years, I love it. And the more the better. I am not one of those people who bristles when I get edits. I don’t always agree with all them. I’ll push back.

Jimmy Soni

Yeah, but you want the...

David Gelles

On balance, I will take that all day because I think it’s going to make me better.

Jimmy Soni

Yeah, that’s great. You’re like an editor’s dream. I mean, yeah, because ultimately you do have to. I would say it’s a productive process to have a fight over a sentence or a paragraph or a word. It’s people with conviction coming to something and saying, I care about this and I think it’s this way. No, I care about it. I think it’s this way. I do think there’s value in that friction. But it sounds like you’re much more accommodating of the people who are editing you.

David Gelles

Yes, and I hold a grudge. You know, I remember specific sentences where I was overruled by an editor. And they were wrong. And I know those sentences. I can pull those URLs up right now.

Jimmy Soni

Let me ask you a more personal question about doing the book writing, because I don’t know if this is true for you. You are, you know, obviously you were a meditator. You’ve had, you know, you described this kind of on again, off again relationship with meditation. But did you find the book at any point consuming you? Were there stages where you felt like the only other people that are going to understand me are people who are doing book projects? Or were you able to turn that off and turn it on again when you needed?

David Gelles

Yeah. And probably because I have a relationship with meditation, definitely feel like it’s the case that my meditation mindfulness practice over the years has made me less neurotic with work stuff on balance.

Jimmy Soni

And so there’s a little bit of this. I mean, there’s a lot of it in the book. But just to go on the detour, the kind of segway about the mindfulness practice, this started for you pretty young. It sounds like.

David Gelles

I was a teenager.

Jimmy Soni

Yeah. And sort of explain to this audience what was the introduction?

David Gelles

I mean, I was a kid in Berkeley, California, who had been exposed to all different paths for opening and expanding the mind and consciousness and found most of them unfulfilling until I learned about Buddhism. And Buddhism just from an almost academic sense, when I first read about it when I was a freshman in college, it just made some intuitive sense, more so than anything else I had read or been exposed to at the time. And so I began, I literally opened up the Yellow Pages and looked up Buddhism and I happened to live in the Bay Area and I found Green Gulch Zen Center, really famous Buddhist meditation center in Marin County. And I went there on January 1st or January 2nd of 1999, and I started sitting and that began a personal relationship with Buddhist practice that led me to then go to India for my junior year of college. And I studied Buddhism in India. Zen, yes. Also Tibetan meditation and then also Southeast Asian Buddhist meditation, which has been secularized as mindfulness. So American mindfulness mostly has its roots in the Thai and Burmese forest monk traditions. And it’s been adapted and made palatable for Westerners through folks like Jon Kabat-Zinn, Jack Kornfield, Sharon Salzberg, Joseph Goldstein, who have done a really elegant job of translating some of these traditions for a Western audience.

Jimmy Soni

Yeah. And you feel like it’s intimately bound up with your ability to do creative work? You know, there’s a reason why creatives have these difficult life circumstances where they can’t, you do deal with neuroticism, you deal with addiction, you deal with all these things. You have always struck me like you have a wonderful life. You’re very well balanced. You take care of your physical health. Do you trace a lot of that to the meditative practices?

David Gelles

Not directly. I know. I feel like it’s bonus, like the fact that I’m able to. I mean, maybe a little. But no, I don’t. I think it’s sort of an additional layer of sanity that I can bring to myself. But I don’t at all suppose that, I mean, the only way to live a balanced life is to meditate. Nonsense. But it brings balance to your work life.

Jimmy Soni

You said it allows you to not be as neurotic about your work.

David Gelles

Sometimes. But I’m still pretty neurotic about my work. Imagine if I didn’t have the practice, how neurotic I would be. I think my wife would have had something to say about that.

Jimmy Soni

That’s really funny. When the book, so, you know, there’s always that moment of you’ve finished the book and you get that first box. The first box moment. Do you remember that for Mindful Work? I mean, it’s your first book. It’s a big...

David Gelles

I don’t remember the box for the first one. For the first book. No.

Jimmy Soni

Then which moment stood out where you finally realized it was real? You’re like, it’s a real thing. And I’ve created this from whole cloth.

David Gelles

I don’t know. I mean, you know, it was just work. I mean, I don’t make too much of that first book. I mean, I was proud of it. Got it out there. I mean, I did a talk at Google. I did a TED talk. It was excerpted, I forget in the, yeah, in the FT or I forget all the places where we had serials. But it was, yeah. I guess I don’t make too much of it.

Jimmy Soni

Right. So it didn’t, it sounds like it was actually a pretty seamless process for you, putting it together and putting it out into the world.

David Gelles

Sure. I, you know, my hair went a little gray in the process.

Jimmy Soni

Interviewing your wife, maybe she’d have something different to say.

David Gelles

Yeah, but, you know, it was one thing among many that was happening in our lives at the time. You know, we were having our children at the same time. We were in New York City and probably moving apartments somewhere in there. I had a really busy day job. I changed, actually, day jobs. I think I sold the book when I was at the FT and when it came out, yeah, now I remember. I was actually at the Times by that point. And so now I do remember. I think the first serial actually appeared in the New York Times. It was a Sunday business section story about Mark Bertolini, then the CEO of Aetna, who was a character in the book.

Jimmy Soni

If I go back, just one quick moment. It was a book that you pulled from the shelf, if I remember right, that actually got you down the Buddhism path. Can you talk about that specific moment? It was very vivid.

David Gelles

I still remember it. It was New Year’s Eve on 1998, going into 1999, and I was home in Sausalito at my mother’s apartment. And she had a great library, including lots of books on religion. She was a museum director and done a lot of work on Asian arts. And for whatever reason, I was sort of restless. I knew that in my next semester at Boston University, I would be studying world religions. I knew it was coming on the syllabus. And so I saw this book, a basic introduction to Buddhism. I don’t remember exactly which ISBN number, but it was a pretty standard intro book. And I just started reading, and I remember I didn’t go out that night. I just stayed home. And I was so consumed by it that I didn’t go out. I just finished the book. My mom was like, are you okay? I was fine. Just more interested in that than whatever was happening in the world. And then the next morning, and this is, you know, this is simplified, but there’s truth to it. I checked in with all my friends who had been inviting me out. And one friend was still hungover. Another had watched his sister relapse and do cocaine. Another had gotten in a fight or seen a fight. And at this super simplified level, the basic equation of desire leading to suffering was there for me. And I was like, huh, maybe these guys are onto something. And so then I opened the Yellow Pages.

Jimmy Soni

Have you revisited that book ever since?

David Gelles

No. No, I don’t go back and read my book.

Jimmy Soni

You don’t go, oh, not this book. I mean...

David Gelles

Oh that, no, I don’t know which one it was.

Jimmy Soni

Okay, so why don’t you go back and reread? I mean, I’m guilty of the same, by the way. I can’t go back and read it. I think it would make me, it would tempt me too much as an editor to want to change everything.

David Gelles

I should be clear. I haven’t looked at Mindful Work in years and years. I have revisited probably, well, certainly Dirtbag Billionaire, because I’m still essentially promoting it and out on the road sharing it these days. The Jack Welch book, The Man Who Broke Capitalism. I think I feel like I’ve gone back and looked at the introduction once or twice because there’s some things I think I did right there just as a reminder to sort of, oh, what was the flavor? What was the tenor there? No, I mean, I think that’s natural.

Jimmy Soni

One of the things that I always, when I’m with my author friends, we sit around, we talk process. You have a job that because of deadlines, you’ve learned the ability to write fast and to hit deadlines and to produce words against a word count total or some rough amount of words with steadiness. You’ve had to do this for a long period of time. But a book, let’s say it’s 65,000 words, maybe 70,000 words. Did you have an approach that you used for this work in terms of how you broke up the work itself?

David Gelles

Let’s set aside Mindful Work because I think that was a long time ago and I don’t honestly remember the details of the craft on that one. But for the more recent books, definitely have a craft and sort of a process and a method. And also to say for both of them, I pretty much understood what the outline was going to be because both of them, The Man Who Broke Capitalism and Dirtbag Billionaire are roughly chronological. And so if you have a chronological narrative, that makes it really nice and easy. I also knew sort of the target length, what you said. I mean, mine are a bit longer. Mine are closer to 85, 93, somewhere in there, I think, both of them. And so then you figure, okay, I’m not a 20 short chapter kind of guy. I’m a 10 sort of longer chapters. All right, so we’ve got 8,000 word chapters with an introduction, maybe a conclusion. And so then, all right, so I roughly know that. And then what I’ve also realized about my writing, I think you’ll see it in the last two books is there tend to be three to four sections per chapter. And so then, okay, break those up. And then we’re talking somewhere between 1,500 and 3,000 word chunks. And that’s a long newspaper article. And to your point, I can do that in a day.

Jimmy Soni

Yeah.

David Gelles

I don’t write 3,000 words a day for a book. But that sort of atomization of the manuscript makes it really approachable to me.

Jimmy Soni

Right. And is that conscious? Like, are you... Okay. And then you just sort of track against the chronology and you keep at it.

David Gelles

Yeah. And the way, I mean, we can talk about how I actually do the research and get things on the page, but that approach of, okay, I need a chronology. Here’s roughly what I want in it. Here are roughly themes of the moments. Then let’s start, you know, breaking it down into, and I use, I use Microsoft Word. I’m a proud Microsoft Word user with the outline function.

Jimmy Soni

That’s old school. Yeah.

David Gelles

And I go down and, you know, I use headings one and I tend to go down to somewhere in the four to six range for the outline function, and then I adhere to the outline.

Jimmy Soni

Why Microsoft Word? That’s, you know, as an aside...

David Gelles

It’s how I started.

Jimmy Soni

Okay.

David Gelles

Are you a Google Docs fan?

Jimmy Soni

I’m a Google Docs person. And then for books, I use Scrivener for some of the raw material. I like Scrivener, because there’s something about it that, I don’t know, it’s like Microsoft Word went to the gym for a couple of years. But it’s interesting to me that, you know, the tools do shape the outcome. And Google Docs has helped me edit on mobile. Edit when I’m elsewhere. I don’t have to make, I can’t make the excuse of having my laptop. I can’t work because I have my phone. I can always do something. But I’m curious. You’ve stuck with just because that’s how you were trained. That’s what you’re sticking with. And it works for you. There you go. You go from the first book to the second, The Man Who Broke Capitalism. What was the process of kind of selling and pitching and working on the second idea? And when did it come to you that there was a story here that needed to be told?

David Gelles

Yeah, I remember where I was sitting when it came to me. It was April of 2020, so we were all in lockdown at the time. I had thought about different books and different projects in the years before that, but nothing had even quite clicked. I’d even thought about a book that had to do with Patagonia, but wasn’t able to get it off the ground, so that one had to come later. But then in April of 2020, I was in my kitchen and I was sort of stirred up at night, looking for something to do because couldn’t go out, couldn’t go to the bar, couldn’t go to a sports game with my kids, couldn’t do all the things we usually do. And so my brain was sort of racing around looking for a target. And really the entire argument of that book came to me in a flash. And the foundation was already there. And it had come through my reporting over the last several years at the Times because I had been the Corner Office columnist where I had interviewed hundreds of CEOs. And then for the year, right up until Covid hit, I was the reporter investigating Boeing and what had happened inside Boeing after the crashes of the 737 Max jets. And those two storylines both led back to Jack Welch. Of all the people I talked to for all the Corner Office interviews I did, the one name that kept coming up was Jack Welch. Even though he had been retired for almost 20 years at the time, even though he wasn’t Steve Jobs or Mark Zuckerberg, Elon Musk, he was the one that was still rent free in the minds of all the CEOs. And that just was weird. So I filed that away. And then in reporting what had gone wrong at Boeing, yeah, all roads led back to GE and specifically Jack Welch’s GE, because a succession of Jack Welch proteges had taken that company over starting in the 1990s and radically transformed it into, be in the image of the Jack Welch GE. And they had ruined the company. And I was sitting, I was again, it was probably 1:30 at night and I was just antsy in the kitchen. And all of a sudden I was like, oh, that’s the story. It’s just a story about how Jack Welch messed it up and so off to the races.

Jimmy Soni

And so what happens from there? You reach out to your agent.

David Gelles

Probably put together a rough proposal, because I sort of knew, I knew what to do at that point. It had been a long time. I mean, it had been five years.

Jimmy Soni

There was a big gap between that book and your prior one...

David Gelles

Five years, I don’t know if that’s huge, but I hope it’s not as long next time.

Jimmy Soni

Next time.

David Gelles

But yeah, it had been five years. I didn’t have another project in the works. And so, yeah, I put together a pitch, took it to my agent, Binky, took it to Eamon. Eamon liked it, and we were off to the races. So it wasn’t competitive. We didn’t take it out and shop it. I knew my team and went, you know, we were off to the races and we did it really fast. So that book, I had the idea in April 2020, and that book came out, if I have it right, in May of 2022. Really fast.

Jimmy Soni

Wow, that is really fast.

David Gelles

Crazy. Yeah.

Jimmy Soni

What was that like, getting that done under such a tight timeline?

David Gelles

On the one hand, it was insane. On the other hand, listen, Jack Welch had just died, so I knew I wasn’t going to be able to interview him. It was locked down.

Jimmy Soni

Right. So you’re not going to be able to travel that much.

David Gelles

There wasn’t going to be a lot of on the ground reporting to do. And even if it hadn’t been locked down, it wasn’t clear. I mean, I could have done some. I could have gone to Schenectady or I could have gone to GE factories and seen that kind of thing, but that wasn’t quite what the book needed. So, listen, I did 100 Zoom and phone calls over the course of a year, read everything I could find about the guy, refined my argument and wrote a manuscript and turned it in, and they turned it around.

Jimmy Soni

That’s amazing. Yeah, that’s amazing. How did it feel different than Mindful Work? What was the, how did the process feel different to you?

David Gelles

Yeah, I didn’t love it because it was an angry book. And so it was an angry book. It’s sort of an angry moment, you know, written during lockdown. And it really is a book with a perspective. And it’s, you know, it’s not a kind one. I’m sort of angry on behalf of the proletariat. So I didn’t love that when the actual writing process, I would have to channel anger, which is not who I am naturally. So I didn’t love that. Nevertheless, I think I got it right and did it appropriately. The one thing I will say is my editor, Eamon Dolan, insisted on a how to fix it chapter at the end, and I regret doing that.

Jimmy Soni

Yeah.

David Gelles

And I’ve told him as much. I wish I hadn’t. And in fact, in some of the reviews they I think rightly pointed out that the solutions we came up were a little facile. That was...

Jimmy Soni

And understandably, it’s, you know, you get a chapter to...

David Gelles

Right. Who am I to fix all of modern capitalism?

Jimmy Soni

There are whole books…

David Gelles

But I bring that up because for any authors or aspiring authors, know when to stand your ground. And it’s your book and at the end of the day, the title, cover, the words in it, your name is the one on the spine. And I think back to a couple moments like that. And there are other times when I think I should have taken advice that I didn’t. But there are also, you won’t forget those times where you roll over when you wish you hadn’t.

Jimmy Soni

This is David’s list.

David Gelles

Like I said, I keep grudges.

Jimmy Soni

I have my own. I was going to ask about titling. The Mindful Work title, you know, somewhat self explanatory. Did you sell your subsequent two books as The Man Who Broke Capitalism and Dirtbag Billionaire or did you come to those titles later?

David Gelles

No. Working title for the Jack Welch book was Neutron Jack, which was his nickname, which I still really like. The argument was made that it was too unfamiliar. People wouldn’t know what it was about. I don’t fully, the book was a success. I think that doesn’t give readers enough credit. I like to trust that they could figure it out. So listen, looking back, I think that would have been a great title for that book. For Dirtbag Billionaire, that was the title I went out with and then it got rejected for almost the entirety of the development of the book. And I reinstated it very late in the process and I’m mostly happy about it. The other alternatives, especially that the publisher and editors came up with, I didn’t like. In retrospect, part of me wishes I could have done something more generic and more accessible, something like The Climb or The Climber. I don’t know if that really would have worked. But I say that because Dirtbag Billionaire, it’s an edgy title, gets people’s attention. But I also have learned that it has confused some people where they think it’s going to be an unflattering portrait of him. And I don’t think it’s a hagiography, but it’s a nuanced portrait. But people, some people have thought that it’s in the same mold as The Man Who Broke Capitalism or I must really not like the guy.

Jimmy Soni

Yeah, yeah, well, and you explain right from the jump in that book that the term dirtbag is a very specific. Can you explain that just so people understand that you’re not slamming the founder of Patagonia?

David Gelles

Yeah. So the term dirtbag in the rock climbing outdoors community from which Yvon Chouinard came is really the highest form of compliment. It refers to someone who is so unenamored with materialism, so disconnected from material needs, that they are literally content to sleep in the dirt if it means they’re that much closer to their next climb. And Yvon Chouinard himself refers to himself as a dirtbag. I mean, to this day, in his late 80s, he says I’m a dirtbag. And so the tension then is, how did this dirtbag ultimately become a billionaire?

Jimmy Soni

Yeah, so let’s get to that. I want to be mindful of time. You know, how did you go from the angry book to the happy book to the David of yesteryear?

David Gelles

I know. Now I need to figure out, is my next book going to be another happy book or does the pendulum have to swing back to be an angry book? So again, this came directly from my reporting, and this is why I’m so fortunate to have the job I do at the New York Times is I get exposed to these amazing stories. So in September of 2022, I broke the news that Yvon Chouinard and his family had given away the company and restructured the entity and various holding companies and trusts in a way that would allow all future profits to be directed toward environmental charity. That was a huge story. The, I think third most read URL at the Times that year after the live blog of Queen Elizabeth’s death and the Trump taxes story. So for a, you know, little story about Patagonia, it just went gonzo. And that was a signal to me that, oh, people are interested here.

Jimmy Soni

Why do you think it went so crazy?

David Gelles

I think it was a number of things. One, we were still in Covid time period. And so I think this was a real story that people could connect to in a positive way. I mean, there is really a hunger for good news out there. I think it was a brand people knew well enough, but here was a big turn about a place and an organization and a family that was still somewhat well known, but also somewhat mysterious. So here was a window into that, their thinking. And then, listen, it just went viral. Because it went viral and sometimes you can’t explain it, but celebrities were sharing it and morning news, and it just popped. And that was super exciting.

Jimmy Soni

And that was the signal for you that there was something here that was longer than just a story in form.

David Gelles

Exactly. And as I had mentioned, I had even thought about a Patagonia book five years earlier, before the Jack Welch book. The way I had initially conceived it was actually as a story about the friendship between Yvon Chouinard and Doug Tompkins. And I thought, wouldn’t it be interesting to write a story about them as a pair? Doug Tompkins, his best friend, founded the North Face and Esprit and was also a great environmental conservationist. Yvon Chouinard founded Patagonia and Black Diamond and is a great conservationist himself. So this pair who had pushed each other and, you know, were together until the end. But when I floated that project with the families back in 2020, just before I started on the Jack Welch book, I basically got the thanks, but no thanks. A movie by Jimmy Chin was just coming out. Another writer was working on a biography of Doug Tompkins. And those projects were both really well done and successful. I wasn’t aware of them when I started thinking about this idea, so I just sort of set it aside. But after this article, I suddenly understood that the Patagonia story now had a third act. Up until that point, you could write a great story about the man and the company, but it wasn’t really clear how it ended because he was still alive. And Patagonia, the fate of that company was sort of unresolved. But now he had answered those questions even if he was still alive. And so then I could write that third act.

Jimmy Soni

It’s still a hop, given a jump from that article and everything else to getting the kind of access you had with him and to, I mean, one of the things about the book is that you’re with him and you’re in remote places doing outdoorsy things. How did that process go? What was it like to get that kind of trust?

David Gelles

It was a journey. I had actually known Yvon Chouinard for 10 years before I wrote that article. So I had interviewed him over the years, just as a business reporter a little. We were not close, but we had some touch points. I think I had earned the company’s trust because I had written a series of stories about the company and they felt like I had done a fair and good job with them. But when after that article, I went to the company and said, hey, I’m going to write a book about Patagonia and Chouinard. The response was, we would rather that you not. Thanks, but no thanks. And I was like, okay. And then I sort of had to take a deep breath and go back to them and say, let me be clear, I am writing this book. I hope you ultimately participate. But we are blessed to live in a country with the First Amendment and you are a public entity. I’m going for it. And so they said, okay. So I then began my work mostly without any participation from the company or the family for the first year. And so I made, I was in touch with a few people, and they would do a little here and there, but for the most part, I was reporting around the story, if you will. And so I made a list of 200 people I wanted to talk to and started going down the list and checking them off and reaching out and making phone calls and emails. And what happened over that first year is I think I know that the Chouinards and the company started hearing from employee number four at the company and said, hey, some guy’s writing a book. And then Yvon heard from a childhood friend and said, hey, this guy contacted me and wants me to talk. And I think after enough of those, they understood that I was serious about the project. And ultimately it was then, it was more than a year after I had begun the project. I get a call, I think, on a Tuesday, from someone close to Chouinard, and they said, hey, what are you doing this weekend? I was like, I don’t know. What am I doing this weekend? They said, get on a plane. You’re coming to Wyoming. And that was when I spent my first sort of extended time with Chouinard and his wife at their home in Wyoming.

Jimmy Soni

Wow. And so it was the kind of, you wore him down, basically.

David Gelles

Well, I don’t know about that. I mean, I was trying to respectfully sort of check in and look for opportunities, but I wasn’t badgering at that point. I was sort of trusting the process.

Jimmy Soni

And they just heard from enough people in the...

David Gelles

I think so.

Jimmy Soni

Okay.

David Gelles

And I made the case that, listen, this book will be better, and it will be more reflective of the truth and his truth if he participates.

Jimmy Soni

Yeah. That reminds me of the story that Walter Isaacson told me where he, for his Kissinger book, he did not have Kissinger’s participation, but he went out and did exactly basically what you did. Hundreds of people, everybody in sort of that land, Kissinger Incorporated. And he got to everybody. And at the 11th hour, Kissinger granted him an interview. And I think the line, I mean, maybe he said this. I don’t know if he did or not, but he was like, yep. And then he proceeded to spend hours just sort of spinning yarns, completely evading, you know, all the things. But it goes to show that, you know, you did something. Did you sell the book before you went out and did that? Like those hundreds or so interviews?

David Gelles

Yeah.

Jimmy Soni

So you had kind of taken a bet on yourself saying, I can, I think I’ll eventually be able to get to a book even if I can’t get intimate access to the family.

David Gelles

Yeah. Because there was enough in the public record.

Jimmy Soni

Okay, got it. About the company, but not the man necessarily.

David Gelles

Both. Yeah, there was a lot about, I mean, I went back and read everything written about the guy for more than 40 years and you can piece together a sketch. I mean, the book wouldn’t be the same without the time I spent with him. But no, you can tell a story about him through what’s out there and through all the subsequent interviews I did with other people who knew him.

Jimmy Soni

Yeah. I want to shift gears a bit just because there’s a part of this that I want to come back to because you made this remarkable thing at the beginning of our conversation about how your kids read four to seven hours a day. And I am, and I’m sure I’m not the only one, very curious about how you managed to do this, among other parenting writing questions I have. But how did you manage to make your kids into readers of that volume?

David Gelles

Starting from the moment they were born, we read to them for hours a day. I think it’s that simple.

Jimmy Soni

Yeah.

David Gelles

And I remember…

Jimmy Soni

Is this at night, during the day?

David Gelles

It’s just all the time. All the time. I mean, we have always had books at their fingertips and we, my wife and I both just spent hours and hours reading to them. And I, you know, I remember my method was I, as I read, I would trace the words, underline the words with my finger. And so both of them were reading on their own at very young ages.

Jimmy Soni

Oh, wow. Okay. And then do you steer the kind of reading they do?

David Gelles

Not at this point, no, they’re in charge.

Jimmy Soni

Got it. But did you do it earlier?

David Gelles

I mean, we still give them books and they’re reading amazing things now. I mean, they’re, you know, my 12 year old daughter is reading, she’s plowing her way through Agatha Christie. And my 10 year old boy just read The Outsiders on a trip and they have elevated tastes.

Jimmy Soni

Yeah. Do you find, how does that world, their world of reading, because I struggle with this. I have a 10 year old and she’s a great reader and she’s a devoted reader. She’s an obsessive. Once she gets into a book, she’ll read the entire series in a flash. But there is always that question of, you know, that mixes in an interesting way with technology and the interruptions that technology creates. So I’m curious, how do you manage that in your own, if you’re willing to share in your own household, how do you deal with the digital distraction against the kind of long, you know, the longer form reading and time spent in that way?

David Gelles

I mean, listen, we try. We are not zealots about no screen times, but we try not to spend a ton of time on screens. We love a good movie, but the TV’s usually off in our home. And, you know, we have a Nintendo Switch, but it gets turned on a couple times a month. So, and listen, it was, it’s Monday today. Yesterday, we started the morning all reading books as a family just piled up on top of each other on a couch. And we ended the day piled up on top of the couch reading books.

Jimmy Soni

Oh, that’s great.

David Gelles

And I think if you model it and talk about it and are able to engage in those conversations, you know, kids respond.

Jimmy Soni

Do your kids make anything of your own life as an author, with the book specifically?

David Gelles

I don’t think they take me too seriously.

Jimmy Soni

Yeah, that’s true. I have a very similar experience. The sad part is my daughter thinks it’s easy because I do it. She’s like, oh, he’s kind of a clown. If he can do this, any schmo can do this. And so that ends up being kind of funny. I don’t think she, I don’t think kids actually appreciate what it takes.

David Gelles

Of course not. Ungrateful.

Jimmy Soni

To the end. How do you, when you, so you have young kids and I have a young kid. How do you balance the range of things you do? What’s the way that you do all this without going stir crazy?

David Gelles

I don’t know. I don’t know. It’s crazy. I mean, I find it, who says, number one, who says I don’t go crazy? I feel constantly crazed. It’s a lot. It’s the, you know, and I’ve got elderly parents in my life who have needs. I have young kids who have needs. I’ve got a busy job. Try to have a relationship, try to have friends. It’s a lot.

Jimmy Soni

Right, right. Do you, for your book length work, when you were in it, especially with the Patagonia book, did you find yourself, how did that one, just to talk process on that one for a second. How did that one get done? Was it vacations? Was it, and then kind of speeding through when you...

David Gelles

Vacations and weekends and, I, you know, last, or whatever summer that was, the summer of 2024, I guess. Book came out in fall of ‘25. So the summer of ‘24 when I was writing it, I missed a lot. I didn’t go to the water parks with my kids that summer and that was an active choice that I had to make.

Jimmy Soni

Yeah. Are you proudest of one of the three projects? Is one of them, you’re like the one, you’re like, okay, this is where I really gave it?

David Gelles

I’d like to believe that I’m getting better as a writer and a reporter and author. So I feel like the most recent book, Dirtbag Billionaire, really works at a lot of levels and I feel like I avoided, I do feel like I didn’t repeat the mistakes in my previous books. I think I probably made some mistakes in Dirtbag Billionaire, but I feel like I landed that one pretty cleanly.

Jimmy Soni

One of the things that we do, just as a matter of thinking about the books we do is think about formats. Do you find that for you, are you an audiobook guy?

David Gelles

I do listen to audiobooks.

Jimmy Soni

Are you, is there a certain kind of book you’ll prefer for audio versus, what’s your reading diet like?

David Gelles

I don’t do literary fiction on audio.

Jimmy Soni

Don’t do literary fiction on audio.

David Gelles

Yeah. Literary fiction I have to read. Yeah. I love biography and history on audio. I love sweeping sci fi fantasy on audio. And I think if I’m being honest for both of those, it’s because if I tune out or fall asleep, I find it easy to come back. And if I’ve missed a few minutes...

Jimmy Soni

Yeah. Is there a book that you’ve read recently that, you know, you actually, it really blew your hair back? Something that really stood out to you.

David Gelles

Yeah. The Wild Trees by Richard Preston, which is not a new book. Maybe it came out 2015 or so, but sensational. Sensational read. Nonfiction. And it’s about the community of men and women who made it their work to find and climb the tallest trees in the world. And it’s, I have goosebumps thinking about it right now. It’s a sensational book.

Jimmy Soni

How did you find your way to it? That’s always one of the things that I’m curious about with books, if you can remember.

David Gelles

I don’t remember how I found that book, but I remember, I mean, the minute I was into it, I was all in.

Jimmy Soni

Wow, that’s amazing. Final question we ask every guest on Infinite Loops is you’re declared emperor for a day. You get a magical microphone and you get to incept two ideas into everybody’s heads. And they will believe those ideas were theirs, not yours. So they wake up and they’ve got a sense of this, of an idea, and it’s from you, and you get two of them. What are your, off the cuff, what are your two ideas? You want to incept into everybody’s mind, of anything. Of anything.

David Gelles

I mean, that people shouldn’t be hungry and without shelter. That we need to take care of the most vulnerable. And that we should organize society in a way that makes that happen without question. And that it is our number one collective priority to take care of planet Earth.

Jimmy Soni

That’s amazing. Well said. Those are both great and it’s a great way for us to bring it to a close.

David Gelles

Amazing.

Jimmy Soni

Amazing.

David Gelles

That’s such a good conversation.

Jimmy Soni

That was fun. That was awesome.

Leave a comment

Subscribe now

Share

They cover her transition from law to writing Power Money Fame Sex, why she often ends up writing the book before the proposal, the art of editing until the final hour (even during pass pages), her 5:30 AM writing routine, and why "know thyself" remains the foundation of all her books - from 40 Ways to Look at Winston Churchill to Life in Five Senses.

We’ve shared some highlights below, together with links & a full transcript. If you like what you hear/read, please leave a comment or drop us a review on your provider of choice.

Links

Apple Podcasts

Highlights

Are You an Opener or a Finisher?

Jimmy Soni: I have the challenge of sometimes you’re sort of, you know, you want to dance with the girl that you brought, but then you have this other project. Like there’s always the other projects that you’re like…

Gretchen Rubin: ... A hooky book. That’s what I have.

Jimmy Soni: That’s a great... that’s a great one.

Gretchen Rubin: I often have a hooky book. Yes. Now my... when I was writing Better Than Before, my book about habit formation, my hooky book was a book that turned into Outer Order, Inner Calm.

Jimmy Soni: Wow. So how do you prevent yourself from going to... and turning the hooky book into the daily driver?

Gretchen Rubin: Right, right. Yeah, that it is. You’ve got to remember it’s a hooky book. For me, it’s all about note taking. So note taking is a big thing for me. So I will let myself take notes on it. Like, and I’ll... I might read for it and take, put notes into it, but I would never allow myself to begin to structure it. Because once I’m structuring, then I’m like, “Okay, now I’m really tackling it as a book.” But because I always start with a bunch of notes, having a bunch of notes, then when I’m ready to start writing, then I have this huge head start. So it’s a good use of my time. But you’re right, you’ve got to make sure that it doesn’t swallow up what your main project is.

Jimmy Soni: Sometimes, by the way, hooky books can yield something amazing, as you put it. You can have... I find that it’s tempting because the beginning of these projects is some of the best. Yeah.

Gretchen Rubin: Okay, so there’s beginners... there’s openers and finishers. Okay, so openers are people who love to open a project. So they love the beginning stages. They love to start something new. Like, I talked to a professor, and he’s like, “I have seven half-finished, you know, new curricula for new classes,” because he loved to open. But then there... and then finishers are people who love to end. They love to finish. And both of them have pros and cons because openers sometimes don’t finish. And so they don’t get the benefits of their work. And they can get distracted because they’re pulled in so many directions. But finishers, sometimes they just want to be done so badly that they might rush at the end because they’re just like, “Okay, I just really want to get this crossed off the list.”

But a lot of times it’s that last work that’s really painstaking and difficult that can really make something go to the next level. And sometimes they are too cautious about what they start because they think, “Well, if I can’t finish it, maybe I shouldn’t start it.” But sometimes with creativity, you kind of have to say, “Well, maybe I’ll start it and maybe it won’t go anywhere, but I need to just kind of get it started to see.” And so I think it’s good to know which one you lean toward so that you kind of can try to offset that.

Jimmy Soni: Are you an opener or a finisher?

Gretchen Rubin: I’m a finisher for sure.

Jimmy Soni: Okay.

Gretchen Rubin: I’m a finisher. I love to cross things off the list. And it is... it’s like towards the end, I feel myself being... let’s just... let’s just say it...

Jimmy Soni: Done.

Gretchen Rubin: Oh, here’s an edit. But I’m just going to decide I don’t agree with that edit. It’s like, I actually do agree with that edit. I just want to be done.

Jimmy Soni: Want to finish.

Gretchen Rubin: Yeah, I want to finish.

Why Do People Throw Their Possessions Away?

Gretchen Rubin: I went through a serious period of being absolutely obsessed with the question of why people destroy their own possessions. And I wrote a law school paper about it, then I wrote a novel about it. And then I actually published a book called Profane Waste as a collaboration with an artist, which is all about this question of why people destroy their own possessions. So I tried it every which way, and then I just ended up with nonfiction.

Jimmy Soni: So this is why you will now... you are now and will forever be one of my favorite people. Because these are the kinds of rabbit holes that I go down. Right. I’ll just find myself lost in some question that possesses you.

Gretchen Rubin: Yes.

Jimmy Soni: And then you ask...

Gretchen Rubin: So delightful.

Jimmy Soni: Yeah, it’s the best. I think Wikipedia scratched that itch for people who are satisfied with, like, you know, 10 to 20%. But then there’s a whole other level. So if you... if you rewind the clock and it may... I don’t know if you can remember this question of why people destroy their own possessions. How did you even get to the question itself?

Gretchen Rubin: Oh, I know exactly. I was again, I was in D.C. I was walking on my lunch hour. This is why it’s important to go for walks because you have all these ideas. And I went to the... one of the... I forget the exact title of the museum, but you know how the Smithsonians, you can just... they’re free. You just walk right in. So I walked in and it was a display about potlatch. And potlatch is a tradition of kind of exorbitant gift giving. It’s like the big man will give extravagant gifts and kind of give away everything as a... and there’s a lot of research about why the custom of potlatch existed. And then when trading came in, these groups of people became... had so much wealth that they literally couldn’t give it away fast enough.

And they were throwing goods into the ocean too, because they just... anyway, but this idea that people would destroy something as a way to show their possession of it just messed with my mind. Okay, then there’s another thing that happened. So this is in my mind. Then something happened. Where? Okay, so I was in law school. I was first year law school, so in love with the guy who’s now my husband. He was a summer associate at a law firm. And because I was so in love, I’m like, I’ll go with you and just do my own thing while you’re doing your summer associate thing. And on our way there, we stopped at a corner store and he bought a couple snacks. I got a couple snacks.

And one of the things he got was a piece of cheesecake wrapped in plastic. Why? I don’t know. So we get there, he does his work, we’re getting ready to leave, and I look in his trash can and I see there’s the unopened piece of cheesecake. And I say, “Oh, I’ll fish this out. You never opened it, like, you know, it’s still good.” And he goes, “No, I don’t want it anymore. Just throw it away.” And this rocked me to my core. I’m like, what are you talking about? What just happened? Right? You just threw it away.

Jimmy Soni: Right.

Gretchen Rubin: And I can... I mean,

Jimmy Soni: Did you have an explanation or did…

Gretchen Rubin: He was just like “Well, I thought I wanted it, now I don’t want it.”

Jimmy Soni: Oh, wow. And there was some part of you that was disturbed by this.

Gretchen Rubin: Absolutely baffled by it. And so that... and then the potlatch, this guy... and then when I got to law school and we were talking about property rights and all the bundle of rights that are property, I wanted to write a paper about it and a lot... and one of my law professors said, “But people don’t want to do that. That doesn’t make any sense. Why would somebody want to destroy their own property?” And I was like, that’s exactly my point. Why do people do this? It doesn’t make any kind of economic sense anyway. So I would talk about a rabbit hole. I went deep down there.

Transcript

Jimmy Soni:

Well, I have an amazing privilege today, which is I’m here with not just one of my favorite writers, one of my favorite people in the world, Gretchen Rubin. And to set the scene for people, this is you and I get together semi-regularly for lunch and to talk shop, catch up. And the way I describe these lunches to other people is I always tell them that they are like a Gretchen Rubin vitamin B shot of energy and ideas and inspiration. And you push me to think more critically about the platforms I’m on or what I’m doing or talk about this or that. And so I’m hoping that our conversation today captures some of that energy, because I do think of you as one of these great pushers of ambition and creativity.

Gretchen Rubin:

Well, I’m so happy to hear you say that. I feel exactly the same way. I feel like I leave our conversations with homework because I have to go home and look something up and figure out how to do something.

Jimmy Soni:

See, that’s way less nice than the version I did.

Gretchen Rubin:

No, that’s the highest praise. Like, I’m actually going to do what you tell me to do.

Jimmy Soni:

Amazing. So I thought what we would do just to give people a sense of where your career started and where your writing career started. You were a recovering lawyer, you went to law school. So can you just walk us through kind of how you got from law school to the formal work of doing books, but just from your legal career to your authorial career?

Gretchen Rubin:

Okay, so I went to law school for all the classic wrong reasons. It was a great education. It’ll keep my options open. I can change my mind later. I’m good at research and writing, so I’d probably be good at this. My father’s a lawyer. So I went to law school. Did very well in law school. I was editor in chief of the law journal, and then I went on to clerk for Sandra Day O’Connor. But at that time, I was sort of starting to realize that I didn’t know what I wanted to do next. And simultaneously, I have this habit of asking myself theoretical questions, just, I don’t know, kind of conversation starters with myself. And I was out on my lunch break.

I was looking up at the Capitol dome, and I thought, what am I interested in that everyone else in the world is interested in? And I thought, well, power, money, fame, sex. And it was like, power, money, fame, sex. It was like this one big idea. I instantly got incredibly preoccupied with it and started just doing masses and masses of research and note taking, which is something that happens to me all the time and has happened to me since I was a child. So this was very familiar. So I was doing all this research, doing all this note taking, and then finally it occurred to me this is the kind of thing a person would do if they were going to write a book. Maybe I could write that book.

So I went to Kramerbooks and Afterwords in D.C. and got a book called something like How to Write and Sell Your Nonfiction Book Proposal.

Jimmy Soni:

Oh, wow.

Gretchen Rubin:

And then, you know, cut to, I followed the directions and that’s how I got my first agent. And that was my first book, Power, Money, Fame, Sex: A User’s Guide.

Jimmy Soni:

Got it. Okay.

Gretchen Rubin:

So that’s how I switched from law to writing.

Jimmy Soni:

Got it. So what I find interesting with that is theoretical question piece. How long has that been a habit? Because you’re one of the great studiers of habits. Have you always done that? Is that something that...

Gretchen Rubin:

Yeah, often it will be a question or it might be a word. Like I went through a period where apocalypse was a word that I was really preoccupied with. And I ended up writing this really bad novel that I have locked in a desk drawer. Or when I was very young, I was really interested in the Salem witch trials. And so I have this little notebook that’s just my nine-year-old handwriting of sort of facts about the Salem witch trials. Now for some reason I have this incredible antipathy to any plot having to do with unjust accusation. So probably as a result of that, I would never study the Salem witch trials now. But yeah, so I will...

And then I got really preoccupied with the subject of color, in a way that I really couldn’t explain. I was just... did enormous amounts of research and I even wrote a little book called My Color Pilgrimage. And I showed it to a couple editors and they were like, “Well, you really had fun with that, didn’t you?” It’s like, that’s not the answer I’m looking for. You know, like you’re a child. So I turned it into... this is, okay, Jimmy, you’ll appreciate this. Like this is very much a today’s solution. I was like, I’ll adapt like 30% of that material and I’ll make it into a bonus for paid subscribers on my Substack.

Jimmy Soni:

There we go.

Gretchen Rubin:

Because nobody seems... so far, nobody wants the entire My Color Pilgrimage. But there’s really good stuff in there. So it is something that’s happened to me. Or like I remember with Churchill when I just all of a sudden was just like, oh my gosh, all I wanted to do was think about Churchill morning, noon and night. And so when I get... that’s when I usually, when I start a book, that’s amazing.

Jimmy Soni:

You reminded me of something, which is there are all of these creative people I admire, yourself included, who have projects that they have taken, let’s say 40, 60, 80, or even 100% of the way, and then haven’t had them see the light of day. And I remember either reading or talking to you about novels that you had unfinished. So that is tantalizing. Like, what are those projects?

Gretchen Rubin:

Okay, so they’re all finished, they’re just bad. But one of the things I would warn anybody doing a creative project is that if you suddenly lose interest, like call it 80% of the way there, if you’re all of a sudden like, “Oh, I just, I’m not interested in this project anymore,” it’s often a failure because if you finish, then it becomes like, am I going to try to get an agent? Am I going to show this to my agent? Am I going to show it to anybody? Like, am I going to admit that this is the best that I can do? And sometimes I think people turn away from it out of self-protection. And so once you get to a certain point, I’m like, take it all the way and then let it succeed or fail.

And like My Color Pilgrimage, like, let’s just say it did not succeed in what I wanted for it.

Jimmy Soni:

But it got a second life now.

Gretchen Rubin:

I found a... as you say, you find a second life for things. You never know. What do they call it? Saving string where things can end up paying off. But any kind of... I think for people who are doing creative work, anything that you’re interested in doing, it’s like, if nothing else, it’s doing scales. If nothing else, it’s practice. If nothing else, it’s learning and not, you know, every... you know, the more failure, the more success means probably the more failures too, right?

Jimmy Soni:

Did the novels come before the nonfiction work or did you... like how, when, in what sequence were the novels? The unfinished, and I’m sure better than you think novels...

Gretchen Rubin:

No they’re finished, they’re just bad. You know what it is? Growing up, all I read was novels. I was an English major. I just read novels all the time. And I didn’t really... so they were novels of ideas, because I didn’t really understand that what I wanted to do was write nonfiction. So I was trying to channel ideas that I had through fiction. That’s very hard to do. Most good novels are really about character. And so once I switched to nonfiction, then I sort of stopped writing novels because I found the right vehicle for the ideas I wanted to express. Yeah, I wrote a novel in law school. I wrote a novel about... because I went through a serious period of being absolutely obsessed with the question of why people destroy their own possessions.

And I wrote a law school paper about it, then I wrote a novel about it. And then I actually published a book called Profane Waste as a collaboration with an artist, which is all about this question of why people destroy their own possessions. So I tried it every which way, and then I just ended up with nonfiction.

Jimmy Soni:

So this is why you will now... you are now and will forever be one of my favorite people. Because these are the kinds of rabbit holes that I go down. Right. I’ll just find myself lost in some question that possesses you.

Gretchen Rubin:

Yes.

Jimmy Soni:

And then you ask...

Gretchen Rubin:

So delightful.

Jimmy Soni:

Yeah, it’s the best and honest. I think. I think Wikipedia scratched that itch for people who are satisfied with, like, you know, 10 to 20%. But then there’s a whole other level. So if you... if you rewind the clock and it may... I don’t know if you can remember this question of why people destroy their own possessions. How did you even get to the question itself?

Gretchen Rubin:

Oh, I know exactly. I was again, I was in D.C. I was walking on my lunch hour. This is why it’s important to go for walks because you have all these ideas. And I went to the... one of the... I forget the exact title of the museum, but you know how the Smithsonians, you can just... they’re free. You just walk right in. So I walked in and it was a display about potlatch. And potlatch is a tradition of kind of exorbitant gift giving. It’s like the big man will give extravagant gifts and kind of give away everything as a... and there’s a lot of research about why the custom of potlatch existed. And then when trading came in, these groups of people became... had so much wealth that they literally couldn’t give it away fast enough.

And they were throwing goods into the ocean too, because they just... anyway, but this idea that people would destroy something as a way to show their possession of it just messed with my mind. Okay, then there’s another thing that happened. So this is in my mind. Then something happened. Where? Okay, so I was in law school. I was first year law school, so in love with the guy who’s now my husband. He was a summer associate at a law firm. And because I was so in love, I’m like, I’ll go with you and just do my own thing while you’re doing your summer associate thing. And on our way there, we stopped at a corner store and he bought a couple snacks. I got a couple snacks.

And one of the things he got was a piece of cheesecake wrapped in plastic. Why? I don’t know. So we get there, he does his work, we’re getting ready to leave, and I look in his trash can and I see there’s the unopened piece of cheesecake. And I say, “Oh, I’ll fish this out. You never opened it, like, you know, it’s still good.” And he goes, “No, I don’t want it anymore. Just throw it away.” And this rocked me to my core. I’m like, what are you talking about? What just happened? Right? You just threw it away.

Jimmy Soni:

Right.

Gretchen Rubin:

And I can... I mean,

Jimmy Soni:

Did you have an explanation or did…

Gretchen Rubin:

He was just like “Well, I thought I wanted it, now I don’t want it.”

Jimmy Soni:

Oh, wow. And there was some part of you that was disturbed by this.

Gretchen Rubin:

Absolutely baffled by it. And so that... and then the potlatch, this guy... and then when I got to law school and we were talking about property rights and all the bundle of rights that are property, I wanted to write a paper about it and a lot... and one of my law professors said, “But people don’t want to do that. That doesn’t make any sense. Why would somebody want to destroy their own property?” And I was like, that’s exactly my point. Why do people do this? It doesn’t make any kind of economic sense anyway. So I would talk about a rabbit hole. I went deep down there. Yeah, it’s such an interesting subject.

Jimmy Soni:

That is totally fascinating on a number of levels. And did you... at that point, you knew you had this curiosity and you knew you had this kind of... you had wanted to sort of take ideas and make them packaged in some way. Novels weren’t going to be it, because novels are based on character, so... but you also achieved the highest heights of like, legal... of what someone could do with a legal education, like clerking for Supreme Court. That is the... that is the NBA of law school graduation. Right. And so... so were you ever at any point in your career, like surely were torn to like, what might be considered more practical, like go down the law, like make partner or all of that. That track against this following every, you know, your curiosities. How did you, how did you deal with that? Sort of in the tail end of law school and then immediately after.

Gretchen Rubin:

Well, right after law school, I went to work for the Federal Communications Commission. So in there I was really acting as a lawyer. I just, I didn’t know what I wanted. I noticed that when I would look, you know how you read your alumni notes, you get that magazine or whatever. And I realized.

Jimmy Soni:

By the way, I don’t think most people read their alumni notes. I think people like you and I read...

Gretchen Rubin:

If one reads.

Jimmy Soni:

Do you know why I read it, though? Do you know the real reason is because I always read it for the... it’s a... it’s a reminder. It’s like the, you know, memento mori. Because it covers people who are gone.

Gretchen Rubin:

It does, right? Sure does.

Jimmy Soni:

And you have this connection to them. Like I look at my Duke.

Gretchen Rubin:

You know they’re your exact age.

Jimmy Soni:

Exactly. And you go back to the end. And I always look for the people who are the untimely deceased, the ones who are close to me in age, where we have the same experience, we lived the same four years at Duke. And you know, for some one reason or another, they’re here, they’re not here, and I am. Right. And it kind of invests your time and your life with a bit more significance. That’s the reason I do it.

Gretchen Rubin:

That’s a great... that’s a great... that’s a great reason. That’s a great... I’m going to start doing that too, because I know exactly what you mean. For me, it was just curiosity, but I noticed that when people had really interesting law jobs, I felt sort of like mild interest. But when they had really interesting writing jobs, I felt sick with envy. So that was one data point. But one of the things that really made it easy for me is I think a lot of times people know they want to leave, but they don’t know where they want to go. And for me, it was less about leaving law and it was more like wanting to write. And it wasn’t even that I just wanted to be a writer where I think some people are like, “I’d like to be a writer.” I’m like, I want to write a book called Power, Money, Fame, Sex. And I have done like a thousand hours of research and note taking about it. And I really want to do this project. And so it was very clear what it was I was aiming for. And I think that made it easier in my mind. So you know the scene in the original Star Wars where they’re in the Millennium Falcon, they’ve got the tractor beam on them, and Han Solo says, “We have to stop pulling back because we’ll rip the ship apart. We have to allow ourselves to be drawn to this destination.” And I’m like... I just felt like I was in the tractor beam, and I was just being drawn so forcibly toward it. I thought, I’d rather fail as a writer than succeed as a lawyer. I have a project in mind. I’m moving to New York City. This is my time to take a shot. And if I fail, then I’ll figure out what I want to do later. But if I take another law job now, it might be too hard to switch. I will have started to invest so much.

Jimmy Soni:

Yeah, because there’s already... I mean, you’d gone and gotten a degree, you’d run the gauntlet.

Gretchen Rubin:

No, I know, right? If I... any more investment in it starts to become something that you just can’t step away from.

Jimmy Soni:

Yeah. I like this metaphor of the tractor beam as a way of thinking about creative influences and things that pull you in. Is that something you’d consciously thought of in the past, like the idea of what’s pulling you creatively in a certain direction or another?

Gretchen Rubin:

I mean, I don’t know about you, but for me, there is a compulsive element to it which is incredibly gratifying, but sometimes inconvenient for people, or it’s not what they want. I think sometimes people feel compelled to do things even though they kind of rationally know it’s not a good idea, but they just can’t resist it. I definitely know that feeling.

Jimmy Soni:

In your case, though, the writing of books happens to be a compulsion, but also a positive compulsion.

Gretchen Rubin:

It’s been very positive for me, but, like, let’s say I couldn’t afford to take a risk.

Jimmy Soni:

Right.

Gretchen Rubin:

Then maybe I would have had to make a different choice. And then it would have been extremely painful for me not to have been able to write the books that I wanted to write.

Jimmy Soni:

Right. So we’re going to bounce around a little bit chronologically. But, you know, one of the things that is true of the writers I know is at one point or another, their childhood was consumed by books. Right. Not everyone, but I would say there’s a pretty high overlap. Like, it’s like 90 plus percent. What was your childhood relationship to books like, how did you...

Gretchen Rubin:

I read all the time, but I... but I read nonfiction. I mean, not nonfiction. I read fiction all the time. No, I was a huge reader.

Jimmy Soni:

Did anybody spark that in you, or was that... how did that start for you?

Gretchen Rubin:

My whole family are readers, and so it’s like a very... like, we would go to the library every week, and it was a really big deal, but so I saw people reading for pleasure. We had a lot of books in our house, but... but it was... yeah, I remember, like, they had to tell me I had to go outside for a certain amount of time when I was little, because otherwise I would just stay indoors and read all the time. So they were like, no, you have to go out for, you know, 45 minutes every afternoon after school. Yeah.

Jimmy Soni:

Did you have favorites growing up? Do you remember some of your favorite readings?

Gretchen Rubin:

A bazillion. And, you know, I still have a love of children’s literature and young adult literature. I’m in adult groups where we read young adult literature and children’s literature, so... but then... but I was also one of those kids who started reading adult books very early. Jane Eyre. You know, I remember Jane Eyre being the first sort of really adult book that I read, and then, you know, all of the trashy novels that you’re not supposed to read when you’re young. But... yeah, even, like... and not even really understanding books like, you know, David Copperfield, but wanting to read adult books.

Jimmy Soni:

And so for me, the books that changed or that engrossed me, I mean, I had a bunch, but it was the Mossflower and Mattimeo series by Brian Jacques was one that stood out for me. And I remember just being able to lose myself in them for hours. And, like, sometimes I’d look up, and all of a sudden, like, day had turned to night, and I didn’t even realize... what were the... do you have... if you have titles in mind from when you were a kid, what were those for you? Did you have anything that stood out?

Gretchen Rubin:

It’s such a basic answer, but I have to say Narnia.

Jimmy Soni:

Oh, really?

Gretchen Rubin:

Yeah.

Jimmy Soni:

That’s not a basic answer.

Gretchen Rubin:

Yeah, yeah. Yeah, I love...

Jimmy Soni:

That’s amazing.

Gretchen Rubin:

And the thing is, I still admire C.S. Lewis tremendously as an adult writer, too. So, I mean, one of the things I love about children’s literature is that a lot of them are masterpieces of literature on their own terms. And it’s, you know, great writers doing... you look at something like Charlotte’s Web, it absolutely will stand up to any adult novel. You know, and just like his adult work does, such as his children’s work. Yeah.

Jimmy Soni:

So fast forward. Actually, this is a bit of a tangent, but you’re... you, you know, you became a parent. How did you encourage this in your daughters? What’s their relationship with reading? Like, how do you think about the parenting... parent as reader trying to inculcate a love of reading into kids?

Gretchen Rubin:

That’s such a great question.

Jimmy Soni:

Asking for a friend.

Gretchen Rubin:

Asking for a friend. But your child is a big reader already.

Jimmy Soni:

She is already and she reads obsessively.

Gretchen Rubin:

You don’t have to fan those flames. I kind of think a little bit people have to find their way to it. But it’s interesting because my two daughters who now are in their 20s, I would say didn’t read a lot for pleasure, but now they are much more. And even my 21-year-old came home from... for college break and was like, “I want to read. I want to spend the summer reading classics. I feel like I haven’t read enough of the classics.” So maybe people come to it later.

Jimmy Soni:

But I feel like you didn’t do any... there weren’t active steps you took other than having books around and being an author and all of that and talking...

Gretchen Rubin:

About it and having people talk about... my husband’s a huge reader too. He reads a lot of policy. He reads a lot of very contemporary fiction. So it was always that people were always talking about it and, you know, but I think the more you sort of try to make people do, then you... I worry about igniting the spirit of resistance.

Jimmy Soni:

Right.

Gretchen Rubin:

Because it’s supposed to be fun. The reason you do it is because it’s fun. But one thing I will do is like, I will be like, “Have you read The Secret History?” You know, like, give them something that you know is going to be really high payoff. Like a really good book.

Jimmy Soni:

Did you write as a child? Did you write stories?

Gretchen Rubin:

No, I didn’t do that .

Jimmy Soni:

Write for the school paper.

Gretchen Rubin:

Well, I wrote for the school paper, but only just in a very perfunctory way. Not like, “Oh, I’m going to be a journalist” or anything. I’ve never had the desire to be a journalist.

Jimmy Soni:

Got it. So it was always ideas and just rabbit holes that you were going down.

Gretchen Rubin:

Yeah.

Jimmy Soni:

And then sort of how to work backwards from there.

Gretchen Rubin:

Yeah.

Jimmy Soni:

Okay.

Gretchen Rubin:

Just on my own.

Jimmy Soni:

So let’s go through the first book in some detail, the process of the first book. Because I think... we’ll recommend your books and people should check them out and we’ll talk more about them toward the end of the interview. But the... the question I have is the first book is like the big threshold. You don’t really... these are like... so you sort of have these book objects, you know that theoretically somebody is behind them. Right, like somebody does something.

Gretchen Rubin:

Yes.

Jimmy Soni:

So you went and bought a book called How to Write Your First Nonfiction Book

Gretchen Rubin:

Book proposal. Because, as you know, like, one thing I think a lot of people don’t understand is writing a proposal is very different from writing a book. And getting an agent is probably harder than actually getting a book deal. So it’s very... the challenge of being a sort of traditionally published author is very front loaded.

Jimmy Soni:

Yeah, but you’re doing this in an era of... so I had the equivalent experience. So my story of the first book is I googled “how to write a nonfiction...”

Gretchen Rubin:

Right.

Jimmy Soni:

But you had to go to Kramers and buy…

Gretchen Rubin:

And buy a book.

Jimmy Soni:

Right. So what was that... what was that like? How did you know that the idea had merit? You know, now you can test ideas. You can put things on Substack, you can put things on Medium, you can put things on LinkedIn. Right. How did you even know to go down that road?

Gretchen Rubin:

Just the utter commitment. Like, I just... it just felt irresistible. But, you know, one thing that’s happened to me over and over in my career is I’ll have an idea and I’ll be like, “This is an amazing idea. This is so fascinating. Everybody’s going to love this idea.” And people will be like, “Yeah, I don’t really get it. I don’t really think so.” And so I often end up writing almost an entire book...

Jimmy Soni:

Oh, wow.

Gretchen Rubin:

Before I write a proposal, because I feel like I have to have it so well developed in my mind before I can describe it in a way that other people see its potential. Like The Happiness Project, my current project, Power, Money, Fame, Sex. I really had to do a huge amount of... it’s very hard to describe what you’re going to do, I think. So I often end up... which is... then I often end up throwing out just a gigantic amount of material because I may have completely changed my entire structure. You know that. That has happened to me many times. I have many versions, almost complete versions of things that then I was like, “No, this isn’t the right approach.” And I’ve had to recast it.

Jimmy Soni:

Have you ever taken a project that far and just abandoned it entirely? Like…

Gretchen Rubin:

No.

Jimmy Soni:

So something’s always netted out from the work you’ve done.

Gretchen Rubin:

Yeah. But I think sometimes... well, I wrote a book called Life in Five Senses, and it’s about life in five senses. And at first…

Jimmy Soni:

Beautiful book.

Gretchen Rubin:

Well, thank you. Thank you. I loved writing that book. But so first there were nine senses. And I wrote it for nine senses. I’m like, “No, actually there’s 11 senses.” And I wrote it for 11 senses. And I was having all this trouble and I was like, “Do I divide it into sub things? I’m like, what about this? What about that? Which ones are alike, which ones are different?” And then I was just sort of like, you know, sometimes you can intuit by extroverting. And you just... I was just talking it out with somebody and they said, “Maybe you just want to do five senses.”

And I was like, “Oh my gosh, this is the big insight of all time.” Like, went home, like, really just threw away everything that didn’t fit. Just did five senses. Which if I had gotten a board book for a three-year-old, it would have been seeing, hearing, smelling, tasting, touching, the five senses. And that was the structure I ended up with. But it took me so long.

Jimmy Soni:

It took you this…

Gretchen Rubin:

But you do have to write through that. Like, you have to understand, like, why is this? What, you know, why am I writing about this and not that? How does this all, you know, how does proprioception... what are my thoughts and feelings about proprioception? Turns out, yeah, I don’t have to go into that so much.

Jimmy Soni:

So when you open up this book, How to Write Your First Nonfiction Book Proposal, what was the process like between that and getting an agent? Just like, you know, brass tacks, because you’re not just, you know, now, if you and I were to work on a proposal, we’ve seen it done. We know what we’re doing. We can kind of approach certain... we know what the method is like, but you’re doing it for the first time.

Gretchen Rubin:

There is a strange variety. Like, I do feel like there are many different ways people do proposals. There’s like, do you do 40 pages or do you do four pages? Do you do, you know anyway? Yes, but we know that those questions exist.

Jimmy Soni:

Right, but you were... you’re dealing with unknowns then, or at least sort of semi-known unknowns.

Gretchen Rubin:

I knew nothing and I knew no writers. I remember when it was a huge thing for me. I’m like, it was like on my list of, you know, like, life goals. It was like, make friends with writers. Of course, like, now I know so many writers, I can’t count them.

Jimmy Soni:

Now you’re like, I need friends who are not writers because they annoy me and invite me to do podcasts like this.

Gretchen Rubin:

This is so exciting. No, but, yeah, I felt like... but I was lucky. I had a few friends from college who were just starting off in that world themselves, very early. But they were able to give me lists of names. And so I did have that. Like, I had... I had who would I send it to? Cold.

Jimmy Soni:

And then did you... was it sort of the first... you had already written a lot of material and then condensed it into a proposal and then sent it off?

Gretchen Rubin:

Yeah.

Jimmy Soni:

And so what was the moment like when you had your first agent conversation or when the agent said yes?

Gretchen Rubin:

Oh, my gosh. It was the hugest moment of my life. I mean, I think it is probably the most important moment because it is the moment where you are... you’re not an amateur anymore. Because even before I got paid, I was like, time is money. And this person saying they’ll represent me means that they’re putting their time in me. This means that I am... I’m on the first rung of being a professional writer. So it was huge. I still have the same agent now.

Jimmy Soni:

Still the same agent all these years later.

Gretchen Rubin:

All these years. All these years. Yeah.

Jimmy Soni:

Did they... do you remember any of the specifics of what they kind of told you after they read the proposal? Like, or did they make changes? Like, how much of a gap was there between what you pitched to the publisher and what you ultimately did with the book?

Gretchen Rubin:

I think it was pretty close. It was pretty close. In general, my agent is really good at saying something’s not good enough, which is a very useful thing. It’s not always the most welcome thing. I’m not always eager to open her emails, but she... you know, I remember with The Happiness Project, I remember her writing something and she was like, “I’m sorry to write this, but I just don’t think it’s there yet.”

Jimmy Soni:

Wow.

Gretchen Rubin:

Yeah. Wow.

Jimmy Soni:

And has her feedback generally as a tuning fork been pretty useful for you?

Gretchen Rubin:

Absolutely. Yeah. No. I think she’s got a really good sense of what’s missing, which I think is often hardest to see as the writer. You don’t see what you’ve left out because you’ve left it out. So it’s... for some reason, it’s just like, that’s something that’s in your vision or tone problems. Sometimes you get the tone wrong. Like you’re trying to be funny, but it’s not landing or you’re not seeing that you need to find a moment of lightness. So I think that’s where her... that’s... and then she’ll do line edits and stuff. But... but yeah, it’s more those big picture things.

Jimmy Soni:

Did you talk to multiple agents or did you kind of find one that really understood you?

Gretchen Rubin:

I did talk to multiple agents. I was just thinking... I was just telling somebody the other day. Do you remember Judith Regan?

Jimmy Soni:

Yeah. The Judith Regan.

Gretchen Rubin:

Okay. Yeah, yeah, yeah. Like, you know, like, huge, big personality. And so my first book is called Power, Money, Fame, Sex: A User’s Guide. And it’s kind of like if you imagine The Preppy Handbook being combined with Machiavelli. Right. And it’s written like a how-to guide. It’s very much... and I’ve always been sort of enchanted by the how-to format. So it’s written and it’s kind of right on the line between, is it satire?

Jimmy Soni:

Yeah.

Gretchen Rubin:

Or is it...

Jimmy Soni:

Or is it real?

Gretchen Rubin:

Like, you know, and so anyway... but it’s very dense because it’s written in this how-to guidebook format. And Judith Regan said to me, she pointed to a page and she said, “Too many ideas.” And I remember thinking, that is the most preposterous thing. It’s like that scene in Amadeus where he’s like, “Too many notes.” I’m like, what do you mean, too many notes? You can’t have too many ideas. That’s what we all want. But now I realized that was actually a really profound insight. Like, I write too tight, I cut too much, I need to loosen. I need to open it. Ever since... that’s something that I’ve... so, no. So I talked to nine agents, I think, at that time.

Jimmy Soni:

What made you want to pick the one you went with? Just to get very tactical, if you can think back.

Gretchen Rubin:

I think she just felt like she understood what I was trying to do. Like, she got why it was funny, she got why it was interesting. She wasn’t trying to fundamentally change it. You know, sometimes my sister writes for Hollywood, and there are these moments where they’re like, “We love it. It’s wizard school, but let’s set it on Wall Street.” You know? And you’re like, “Okay, I don’t really see...” So sometimes you do get... or just their taste. Like, sometimes people have a taste where you’re thinking, I don’t want to be fighting their taste. So I just felt like we were the most in sync in terms of her response and everything.

Jimmy Soni:

So, and so you send a proposal to the agent and I remember this process. And they then, you know, at the time especially, it was much more of a black box. Like, you just don’t know. You don’t know what they do.You don’t know what cocktail parties they’re going to.

Gretchen Rubin:

I think it’s still… It takes forever.

Jimmy Soni:

It takes forever. What was it like? Did you... how did you land on the publisher you found? Like, what was that process like? Like, did they... did you have multiple offers? Like, how did you... do you remember back to what happened?

Gretchen Rubin:

Gosh, isn’t that crazy? I don’t even remember if I had multiple offers. I’m still really good friends with my first editor, Greer Hendricks, who now herself is like a very, like, you know, like a number one bestselling author of psychological thrillers. So she’s still in my life as well. I might have only gotten one offer for that. And I remember, like, you know, somebody said, “Well, how much did you get?” I’m like, I would have done it for free. I would have done it if they had said, “We’re paying you $0, but we will publish it.” I’ll take that deal. Yeah.

Jimmy Soni:

I always tell authors to just write the proposal. Like, it’s not... you don’t really lose that much. If you’re trying to put a nonfiction book project together and you know, you could go one of two ways. Your way is far... it requires far more... it’s actually much more admirable in some ways. You sort of write the book fully through.

Gretchen Rubin:

But I will say, like, I’m not in... I don’t have to do things like traveling to do interviews. Like a lot of nonfiction authors, there’s a huge financial thing, whereas I’m really writing more of an essayistic thing where it’s my time and it’s like money that I don’t have in my pocket now. But I’m not paying, you know...

Jimmy Soni:

Paying to do the proposal because a lot...

Gretchen Rubin:

Of people, they have enormous expenses associated with actually writing the book.

Jimmy Soni:

But I tell authors too, that the proposal does help you clarify. Like, even if you’re going to self-publish, even if you’re going to do anything.

Gretchen Rubin:

100%. Right. No, you, everybody wants to skip that stage because you’re like, “Why should I waste my time on a proposal? Let me just skip to the book.” But you’re right, it can save you. A lot of times, I think people write a proposal and they realize it just doesn’t... just doesn’t hold up. And then you’ve saved yourself tons of grief.

Jimmy Soni:

You actually are forced to get the structure down. I mean, you’re forced to do much of the book.

Gretchen Rubin:

Yes.

Jimmy Soni:

You know, even getting style and tone.

Gretchen Rubin:

Such good advice. Pacing. Like, you can look and say, “Oh, this book is really out of pace. Like too much of it is in two chapters. But I’m saying there’s 10 chapters. Like, I have to...” That’s... you can’t have a book like that.

Jimmy Soni:

And I would say even the comp titles then force you to make the argument about why your book is different. And I was going to ask you about that project in particular, because it’s not like you’re the first person to write about those four themes. Right. What, in your head back then, what were you trying... how were you trying to position it to make it different?

Gretchen Rubin:

Well, part of it, that it was this really how to....

Jimmy Soni:

Yeah.

Gretchen Rubin:

And it’s written and it is... it’s written in a particular tone. It is very distinctive whether or not you like it. It’s a distinctive book. Yeah.

Jimmy Soni:

When you go back, what was the... so you get the deal? Do you remember any of those moments, like when you find out that you’re going to do it and then... because there is a moment where you figure out you have the deal and you’re like, “Oh, I’m like the dog that caught the car.”

Gretchen Rubin:

Right, right, right.

Jimmy Soni:

Did you have that feeling at all?

Gretchen Rubin:

Oh, no, just so happy to be... just... yeah, but, you know, I mean, to your point about the kind of the confusion around the process, one of the things I, and I often will say this to people who are on the publishing side. I’m like, people know how to be a writer, but they don’t know how to be an author. Like, they don’t know what trim size is. They don’t know what trade publishing is. They don’t know what a pub date is. They don’t know what first run is or first serial or promo copy. You know, there’s all these things that you don’t understand. And I think a lot of times they don’t know what you don’t know.

And I do remember a lot of it just feeling like, “Oh, I’m supposed to know so much more about this process” and feeling like I shouldn’t just say, “Oh, I don’t... I really don’t know what that word is, or I don’t know...” You’re asking me a question, but I don’t know that I don’t know the implications of my answer.

Jimmy Soni:

Right.

Gretchen Rubin:

Like, I remember somebody who was... who self-published and they changed the number of pages and then when she got the book, the quality of the paper was lower than they had agreed to, and they said, “But you raised the page count and that meant the quality of the paper had to change.” And she’s like, “But I didn’t know the implications of that decision.” So you don’t know again, you don’t know what you don’t know. So now I try to really just admit, like, “I don’t know what you’re asking. I don’t know what that means.” Even now.

Jimmy Soni:

It’s an interesting... you know, I had a similar experience, because I don’t know if you felt this way. I certainly felt this way. You get the first deal and you do feel a bit like you’re like, “I got away with something.” Right. Like, I sold this thing to you. You’re about to give me money and you don’t know...

Gretchen Rubin:

Yeah.

Jimmy Soni:

That I have no idea what I’m doing.

Gretchen Rubin:

Right.

Jimmy Soni:

Right.

Gretchen Rubin:

Here I go.

Jimmy Soni:

So then, so then you start doing it and they will ping you with things or send you terms of art within the publishing world and you don’t want to reveal to them...

Gretchen Rubin:

Yes.

Jimmy Soni:

You have no idea what you’re doing.

Gretchen Rubin:

You just try to fake your way through.

Jimmy Soni:

Just like, “No, good.” And then you’re furiously trying to look up what the answer to the question is.

Gretchen Rubin:

Yeah.

Jimmy Soni:

I think this actually drives a lot of authors to drink like...

Gretchen Rubin:

It’s a pub day for a reason.

Jimmy Soni:

Well, it’s a good thing you... you do find yourself having to fake it, especially if you’re getting started. You don’t know what you don’t know. And then worse is you don’t know... you always have this persistent fear, at least I did with my first book, of if I say the wrong thing, they will wake up to me being an imposter, take the deal away and say, “What business do you have doing this kind of work?” Right. Yeah, did you... was any of that part of your experience of writing the book? So once you go through the deal, you’re done with the deal. We’ve gotten past the deal, now you’re in the writing. What was that process like? Like, how did you... because this is your first time out.

Gretchen Rubin:

It was my first time out, yeah. Like, I remember not understanding something like first pass. I don’t... I still am like, “Remind me, what about first pass?” For me, a huge thing. And I didn’t know this until I was on my third book. So this is... this is the kind of thing you learn the hard way is there is... there’s a point at which you can make lots of changes. You can change anything you want. You could add an entire huge chapter. You could change the ending. You can do anything you want. Then there comes a point where your window is starting to close. Then there comes a point where you’re looking at it, but they’re only going to fix a mistake, a typo, a factual error, and they might charge you even for that.

And then there’s a point where they’re like, if you do, it is the hugest, biggest deal. And what... and I also learned is every time you go into a draft and make a change, you introduce an opportunity for error because something goes wrong, there’s a stray punctuation piece that doesn’t get caught. Or you use the same word two sentences above, but you forgot to check because you just added this one thing and you didn’t realize you just used the word “pageant” or whatever. So one thing I’ve learned is you need to watch... I need to watch that very carefully. Like, what... what stage of editing am I in? Because I will edit every single thing up into the last minute. I would never just say, “Oh, it’s done, pencils down.” Oh, here’s a question for you.

Somebody just asked me this question. Let’s say you submit a draft to your editor, okay? So it’s with your editor. Are you like, “Okay, now I’m going to take a break from the book while it’s in their hands”? Are you like, “I will continue to edit myself and then I’ll just incorporate their edits into whatever I’ve done”? It never even occurred to me to stop editing my own work. I’m like, of course I’m going to edit every single day. I’m not going to wait for them, right? Somebody was like, “That’s... why would you do that? That’s bonkers.” I’m like, “Okay, what’s your thought?”

Jimmy Soni:

So this is the thing, is that you and I are wired very similarly in this way, but it is also an editor’s nightmare to have this happen, right? Like in the sense where the diverging... where the diverging... well, because I’m like you. As soon as I turn it into them, you’re immediately thinking, “Okay, let’s go back and revise every chapter and blow things up and twist...”

Gretchen Rubin:

Things around because you got this time. You can’t wait.

Jimmy Soni:

Yeah, you can’t wait. And the thing so I would say one is I know you probably feel this way as well. No one is going to invest the time into my book that I will, full stop. My name’s on the front. I live and die by the words in it.

Gretchen Rubin:

You’re thinking about it morning, noon and night.

Jimmy Soni:

I can’t tell you. I mean for most of the books I love, I probably couldn’t tell you who published them with a couple exceptions. I know sometimes, like just because of the way we’re in the industry, I know some of the editors that are putting out the work I like. But for the most part, most listeners aren’t going to know who published the last great... unless they looked at the spine of the book. I know I’m going to live and die by the words and I know that I’m going to obsess over them like nobody’s business. And here’s the thing. I think there’s... there’s the way publishers tell you that the editing ought to go, which has a rhyme and reason, by the way. Like there’s a reason why they do things the way they do.

And I have found that process is actually first rate. Everything kind of post-copy editing production with traditional publishing is actually phenomenal. Right. But I have found that we’re ultimately dealing with a PDF and in 2026, making those changes is not that big of a deal. Like there’s ways to work around it. I edit right up until the goal line. I edit until I can edit no more. If it were possible to edit in the hour before it was sent to China to get printed...

Gretchen Rubin:

I would too. Because you’re constantly... like that verb is kind of, you know, vague. I can strengthen that. Or like, “Oh, I thought of a...” Or like for me I use a lot of examples. So if I... that I get from real life. And sometimes I’ll just get a much better example from life. So I’m like, “Well, I want to swap this example for that example because it’s just a stronger, more interesting version of the point that I’m trying to make.” Or you just have an original idea and you’re like, “Oh, I want to layer that in” and...

Jimmy Soni:

I would frame it differently. And this is true of all creative work for me. It’s just a touch different. The specifics matter what you just said about word choice and about... but I actually think what happens is if you have a deadline where you’re supposed to send something into an editor, you pour an enormous amount of energy into everything leading up to that moment, right? And you sort of give it your all. It can be this whole body experience of editing. Your friends can’t talk to you. You sort of can’t communicate with the rest of the species. Your family starts to resent you a little bit. You drive and drive and drive. And let’s say it’s like a Monday at 5 o’clock and you press send Monday at 5 and you send them the draft.

You’re so fried, at least for me, I’m so fried at the end of that process that if I take a day or two, the editing I do after that is better often than the editing I did at the tail end of that crazy marathon. So I take a day or two break, but then I get right back at it because I’m bringing better energy to it than I was before. So I actually think of it as super important to go back and dive into the draft as opposed to walking away from it. Because in that state, I don’t know what I was doing in the 72 hours leading up to the deadline. Maybe it was good, maybe it was bad. I frequently find it wasn’t that good. And so I think it’s an energy management thing.

My energy goes all the way to empty right up until the deadline. And then it sort of fills up in the day or two after and I’m ready to look at the project with fresh eyes. And ultimately... the line I always use... everybody wins. Like, we’re gonna sell books.

Gretchen Rubin:

Yeah. No, no, no. It’s better to have a better book, always. Well, one thing I want to do too is read the book aloud. And that takes a lot of time. And so that’s the kind of thing that’s good. Nobody’s gonna do that other than you. And so that’s the kind of thing also that you can do when you’re sort of in that downtime. Because it takes a lot of time to do it and a lot of focus, but you can kind of do it in that period.

Jimmy Soni:

So you go right back into editing as soon as you turn it in and start to dive right back in.

Gretchen Rubin:

Well. And I don’t even really have a deadline. So what I’ll say to my editor is, “I will edit right up until the time I’m ready now. What I have now is a complete draft, but I will continue to edit it. So when you’re ready to read it, tell me and I will give you the most up-to-date draft.” Because if you’re not going to read it for a week, it’s already going to be changed by the time... so for me, the deadline is always, “Okay, I’m ready to read it now. Send it to me.” And then, so they’ll have the most up-to-date one. And then... and then... so I... so for me, the deadline is just

Jimmy Soni:

A suggestion.

Gretchen Rubin:

It’s... it’s like now I’m... by when do you need to have it be ready for you? And a lot of times I find editors really aren’t ready. Like they might say, “I’ll be ready early this month,” but then they have something that came in that needed a lot more work than they expected. And so they’re not really ready right then. So I always feel like it’s good to say... and I think, when are you ready for me?

Jimmy Soni:

Well, and I think the publishing industry is pretty accustomed to delays, right? Like it’s... it’s like you can always move it back. You can’t move it forward. I followed that rule sometimes in a reckless way. Like I... I actually got charged for additional editing. I was one of those people because I edited during my first and second and third pass pages.

Gretchen Rubin:

Oh, okay...

Jimmy Soni:

But then, but then here’s the thing. Don’t do it at home. Really don’t.

Gretchen Rubin:

Yeah, there’s a point where they get very, very cranky.

Jimmy Soni:

Yeah, I would say that being on the other side of it, I understand why they get cranky. And at the same time, there’s a writer I really admire, Erik Larson, who talks about how he edits his first and second and third... and I was like, you know, if it’s good enough for Erik, it’s good enough for me. Like, because there is something... what I would say is the reason that authors edit the first and second and third pass pages, sometimes more aggressively than a Word document or Google Doc or something else, is because we’re finally seeing it laid out on page.

Gretchen Rubin:

It makes a huge difference.

Jimmy Soni:

I don’t know if you’ve had that experience. You have.

Gretchen Rubin:

No, I... funnily enough, I think anything that you do that changes the way it looks... if you print it out, you’ll pick up completely different things. If you read it out loud, you’ll pick up different things. You can put it in a different font. Because I feel like my font kind of looks like my handwriting and if I even... but there is something hugely psychological when it’s laid out and it looks like a Xerox of a page of a book. No, in fact, that’s a really good point. I mean, I’m sure now we could easily do that ourselves.

Jimmy Soni:

Oh yeah. It’s much easier.

Gretchen Rubin:

That’s a really good idea. I want to do that.

Jimmy Soni:

It’s much easier. And I actually...

Gretchen Rubin:

Just because as you say, you pick up a completely... you have a completely different sense of your book.

Jimmy Soni:

Well, you do. And also, by the way, the simplest example, and it happens all the time, is you write a paragraph and you think it’s short, but it turns out to be really long. The only time you realize it’s really long is when you see it in your first pass pages. You look at it and you’re like, “This is a giant block of impenetrable text that nobody is going to want to go through in 2026.” Right. Like this is... we don’t... we don’t have these kinds of attention spans. I need to take this, create an indent. And I’m only going to know that when the first pass pages come around.

Gretchen Rubin:

Yeah. Where your line edits fall. I mean your line breaks fall. Whether your headers are working. I think a lot of things do become... you... just a lot of stuff sort of... that’s a really good idea. I’m going to do that. Like figure out how can I make it look like... maybe they can do it just... well, we’ll just do it to you as a favor.

Jimmy Soni:

Yeah.

Gretchen Rubin:

Like just to kind of fake it.

Jimmy Soni:

A fake first pass.

Gretchen Rubin:

Half pass pages. That would be real. That’s a really good stage.

Jimmy Soni:

It’s a great stage. And it’s also... it’ll save them time. It’ll save them time later. It’s also an important stage. Like it really is. Like you look at it differently, you feel differently about it. I’ve... I’ve actually cut chapters in half.

Gretchen Rubin:

You’ve got to publish... you’ve got to introduce the half pass pages.

Jimmy Soni:

We’ve got to introduce. Yeah this will be our... among our many innovations, another one. The... the thing about it though, if people don’t realize that when you’re... when you are... have stared at something as often as your own words on the page, the change in form matters a great deal. It is the only way to see them afresh. You don’t... otherwise you’re just looking at the same document the same way. And so for me, I do this thing, I have a tracker for every chapter of a book and it has “read aloud, question mark,” “printed, question mark,” “printed edit, question mark” and like what was it? Oh, mobile. So I read on my phone. So I also...

Gretchen Rubin:

I’ve never done that.

Jimmy Soni:

So let’s nerd out for a second.

Gretchen Rubin:

Wow.

Jimmy Soni:

So here’s why there’s two or three reasons why. The first is people are reading on smaller form factor devices.

Gretchen Rubin:

They are, that’s 100% true.

Jimmy Soni:

So you have people who will download the book to Kindle, they’ll have their Kindle synced to their phone.

Gretchen Rubin:

But even a Kindle is a smaller format than reading a book. So you are... they’re multiple sizes.

Jimmy Soni:

So that’s one reason is people... my readers are reading that way. The second reason is an interesting one. If you’re working in Google Docs like I am, but I’m sure this is true of any software you’re editing on. You can find a mobile version. When you’re in your phone. You actually... because of the way we text and because our thumbs are doing a lot of thinking, I find that I write differently. And so when you’re reading something on a phone in Google Docs, you’re kind of having this experience of, what if this was being... what if this passage is being texted to a friend? Does it work?

And so it’s actually... it’s a way to sort of look at it and be like, you know, this could be tighter, this could be shorter, this could be more succinct. It pushes you in the direction of being succinct. That’s reason two.

Gretchen Rubin:

That’s really... because a lot of times I might... this is the training as a lawyer that I always have to push back is a lot of times my first is really kind of long and wordy and it’s like pull it back. Be more succinct, speak more clearly. That’s a really good point.

Jimmy Soni:

The reason is if you turn off your notifications, which you should anyway, you realize that on a computer it’s much easier to be distracted because you have to make an affirmative choice to open up a new tab or change software to... it’s a real choice for some reason to me on a computer to go and be distracted. I’m sorry, it’s not... it’s a much easier choice on a computer to be distracted than it is on a phone. Because with a phone, I find that if I’ve got the notifications off and I’m looking at that document on my phone, there’s something about it that’s much more... it compels me to focus on it as opposed to, “Oh, I could just drift off and do this, or drift off and do email or anything.” The final reason is simple.

I have my phone with me all the time, so I can always be editing. Like, you’re on the subway, you can edit. You’re waiting for a friend at a restaurant, you can edit. You can edit in all these little confetti minutes, right, that you just sort of track during the day. And I find that for me, editing on the phone has actually become a big part of getting books to just be snappier, be more succinct. It’s a totally different way of looking at it.

Gretchen Rubin:

That is such a good idea. I’m gonna... I’m gonna instantly do that. I never thought of that because I know I always read books on paper, right?

Jimmy Soni:

Same, and I’m old school in that way, I love my paper books.

Gretchen Rubin:

I love my papers. So it just... it didn’t occur to me, but 100% I know you’re exactly right. And it’s just any... anything that switches it up reveals new problems, basically.

Jimmy Soni:

One question I have. Not about just your first book, but about projects in general. There are lows in projects, right? So you and I have talked about the highs, right? We covered the highs. Did you have with your first book or with subsequent books? Do you have a method or a way of dealing with the moments when you feel stuck or when you’re like, “I don’t know if this is going to work” or that kind of thing, or do you just breeze through?

Gretchen Rubin:

No, if I feel stuck, I... I will just get up and walk around. So I won’t persist in something that I’m stuck. And I’m a big believer of the unconscious mind will be working on something. So like, let’s say... let’s say I’m in a late stage of editing. And so I have five problems left to solve. And these are the hardest problems because I did all the easy ones first. So I might just look at them and think about them and then walk away or, you know, let a day go by and try them again. And then if I still can’t solve them, sort of repeat. So I’m in the problem and trying to... and trying to... and really pushing myself to try to solve it.

But if I haven’t solved it, then I’ll get up, walk around. I’m also really a morning person. So I get up at 5:30 and from 5:30 to 9 is the best time for my thinking. So anything that’s hard, I do then. So if I have a hard problem, I’ll sort of skip it and save it to do it first so I can do it first thing in the morning. Because that’s my, by far, my best time. But yeah, I think there’s always problems. There’s always things when you’re like, “I don’t...” This is something I should incorporate, but I don’t see how or where it should go or how you would even broach it or it’s a complicated idea that’s hard to succinctly convey.

Jimmy Soni:

You know, when you’re in the middle...

Gretchen Rubin:

Some kind of pervasive issue you gotta tackle when you’re in the...

Jimmy Soni:

Middle of a project. I have the challenge of sometimes you’re sort of, you know, you want to dance with the girl that you brought, but then you have this other project. Like there’s always the other projects that you’re like…

Gretchen Rubin:

... A hooky book. That’s what I have.

Jimmy Soni:

That’s a great... that’s a great one.

Gretchen Rubin:

I often have a hooky book. Yes. Now my... when I was writing Better Than Before, my book about habit formation, my hooky book was a book that turned into Outer Order, Inner Calm. Yeah. Yeah.

Jimmy Soni:

Wow. So how do you prevent yourself from going to... and turning the hooky book into the daily driver?

Gretchen Rubin:

Right, right. Yeah, that it is. You’ve got to remember it’s a hooky book. For me, it’s all about note taking. So note taking is a big thing for me. So I will let myself take notes on it. Like, and I’ll... I might read for it and take, put notes into it, but I would never allow myself to begin to structure it. Because once I’m structuring, then I’m like, “Okay, now I’m really tackling it as a book.” But because I always start with a bunch of notes, having a bunch of notes, then when I’m ready to start writing, then I have this huge head start. So it’s a good use of my time. But you’re right, you’ve got to make sure that it doesn’t swallow up what your main project is.

Jimmy Soni:

Sometimes, by the way, hooky books can yield something amazing, as you put it. You can have... I find that it’s tempting because the beginning of these projects is some of the best. Yeah.

Gretchen Rubin:

Okay, so there’s beginners... there’s openers and finishers. Okay, so openers are people who love to open a project. So they love the beginning stages. They love to start something new. Like, I talked to a professor, and he’s like, “I have seven half-finished, you know, new curricula for new classes,” because he loved to open. But then there... and then finishers are people who love to end. They love to finish. And both of them have pros and cons because openers sometimes don’t finish. And so they don’t get the benefits of their work. And they can get distracted because they’re pulled in so many directions. But finishers, sometimes they just want to be done so badly that they might rush at the end because they’re just like, “Okay, I just really want to get this crossed off the list.”

But a lot of times it’s that last work that’s really painstaking and difficult that can really make something go to the next level. And sometimes they are too cautious about what they start because they think, “Well, if I can’t finish it, maybe I shouldn’t start it.” But sometimes with creativity, you kind of have to say, “Well, maybe I’ll start it and maybe it won’t go anywhere, but I need to just kind of get it started to see.” And so I think it’s good to know which one you lean toward so that you kind of can try to offset that.

Jimmy Soni:

Are you an opener or a finisher?

Gretchen Rubin:

I’m a finisher for sure.

Jimmy Soni:

Okay.

Gretchen Rubin:

I’m a finisher. I love to cross things off the list. And it is... it’s like towards the end, I feel myself being... let’s just... let’s just say it...

Jimmy Soni:

Done.

Gretchen Rubin:

Oh, here’s an edit. But I’m just going to decide I don’t agree with that edit. It’s like, I actually do agree with that edit. I just want to be done.

Jimmy Soni:

Want to finish.

Gretchen Rubin:

Yeah, I want to finish.

Jimmy Soni:

There’s a... there’s that expression, once you’re lucky, twice you’re good. Right. And the first time I did a book, I really did feel like I was... I mean, I knew the book was good, but I felt like I got lucky. It was the second time where I was like, “Okay, I can actually... this is a real thing. I know how to do this.” Did you have a similar experience? Like, how was it... what was the process like from the first to the second project? Because you also changed.

Gretchen Rubin:

Yeah, I changed style. My second book was a short, unusual biography of Winston Churchill.

Jimmy Soni:

Which is... it’s a fantastic book. It’s really great.

Gretchen Rubin:

No, I love that book for me, and this still is a thing which is, are you going to be able to write your next book? If you’re a traditionally published person, that’s a concern, which is, are you going to get published again? Are you going to get a deal again? You know, is somebody going to want to publish you again? So I do feel like that. And I’ve never done a two-book deal, so I’ve always faced that, which is, I’m going out there again.

Jimmy Soni:

Right. And so how did you go from power... from the power book to... to Churchill? Like, what was that process like?

Gretchen Rubin:

Well, when I was studying power, I kept coming across these references to Churchill. So then I became very preoccupied with Churchill. And then a lot of my books have sort of an origin moment. And so I was standing at the corner of 69th and 3rd Avenue and I said to my husband, “You know, you could write a book about Winston Churchill that would just be the most adulatory thing of all time. And you could write a book about Winston Churchill that is so critical of him. And both of them could be completely factually accurate.” And he said, “You could write that book.” And I was like, “Oh my goodness, I am 100% going to write that book.” And I had been reading all these biographies, so I had all these thoughts about the nature of biography.

That’s another unwritten book that I have. I have this enormous collection of quotations about the nature of biography which I could work into something which I actually... I forgot until this minute I had. I should go back and look at that because it’s very cool. But anyway, so 40 Ways to Look at Winston Churchill is both about Winston Churchill and it’s also about the nature of biography. But how this connected with Power, Money, Fame, Sex... like in my mind, they’re very closely associated. From a book publishing standpoint, they’re not closely associated with it, but I was just able to pull that off.

Jimmy Soni:

Yeah. And how did... did you have to convince, coax, cajole, like, you know, because you’re one of the rare people and this is a true gift that you’ve managed to jump from idea to idea. But they’re very... they can be very disparate. Right. Like it... they’re... to quote the… the pudding has no theme. I know it has a theme, and I kind of know that you’re following your intuitions and your curiosities, but it’s not as though you’re a sort of...

Gretchen Rubin:

They’re all about human nature. To me, that’s the thing is they’re all about how do you... and one of the ways you understand human nature is you look at someone like Winston Churchill or JFK, and they’re just so huge and there’s such a vast quantity of information about them that you can study them in a way that you can’t study somebody who’s just more... a more modest player on the world stage. So to me, they feel very connected. But you’re right, but from a publishing standpoint, they’re incredibly disparate.

Jimmy Soni:

But I’m surprised that nobody pushed back to say, “Could you do another book on, you know, power? Or, hey, could we take one of the verticals and really go deep?”

Gretchen Rubin:

I know, I know. It’s... yeah. Now to me... yeah. Because once I started writing about happiness, I have... they’ve all been sort of connected with how do you have a happier life?

Jimmy Soni:

Right.

Gretchen Rubin:

And it is nice to sort of be building around a core subject now with 40... so when I wrote... so I wrote 40 Ways to Look at Winston Churchill, it did pretty well. I wrote 40 Ways to Look at JFK. And you know, when a book flops, they tell you. Or at least my team tells me. “Your book didn’t find its audience.” My book didn’t find its audience. I wanted to write 40 Ways to Look at Richard Nixon. Oh, and that wasn’t going to... just like, this just wasn’t a form. I probably would have kept going. I wanted to do Ben Franklin. I wanted to do Leonardo da Vinci. I wanted to do Saint Thérèse of Lisieux. It just wasn’t supported by the market.

Jimmy Soni:

Why do you think Churchill worked but JFK didn’t?

Gretchen Rubin:

Okay. So I think I have a theory about that. Let me tell you what I think. So I think the people that... that are interested in JFK are... they are either they adore Kennedy and admire him tremendously and everything that he stands for in their minds, or they think... they really... this... you know, they think Kennedy was such a fake and he was doing all this stuff and it’s like this dark underside and what was he getting up to? And so a book that talks about…

Jimmy Soni:

Either camelot or conspiracy.

Gretchen Rubin:

Yeah. Exactly. That’s perfectly... well, that would be great cover copy. Yeah, you’re thinking like a publisher.

Jimmy Soni:

People are getting a window to basically what we do at lunch.

Gretchen Rubin:

So they don’t want to see the other side. They want one or the other, they don’t want to see both. And so people would look at this and they’re like, “I don’t want that.” Whereas I think the people who come to Churchill... so when I wrote the Churchill... and this is a good example of the fact that when you write a book, you never know who the true audience for the book is. You don’t know who it’s really going to appeal to. So when I wrote the Churchill book, I was thinking, there are all these people in the world who have no idea that Winston Churchill is the most fascinating character in history and I will be the gateway drug. They will read my short book and then they will go on to the eight-volume biographies, which I think is absolutely fascinating.

But they don’t yet know that they want to read. Yeah, but that wasn’t who the audience for the book was. The audience for the book was the people who had already read every single Winston Churchill biography. They knew tons about him. So they were interested in my take, because my take was, look, 40 Ways to Look at Winston Churchill. So it was looking at him through all these different lenses, often which were very much in opposition or very surprising. And they’re meant for paradoxical. They were meant to sort of show you what you could... the limits of biography. So people who knew a lot about Churchill were the people who were attracted to that and who... and with whom it resonated. So it was not at all the audience that I thought I was writing to. It was like the opposite.

But I think that audience didn’t exist for JFK because the Churchill people, I think that was an audience that understood the triumphs and tragedies. You know, I think that’s even the title of one of the big... yeah, they got it that his flaws were his weaknesses and his weaknesses were his strengths. And you know, so part of it, I think had to do with the nature of the audience for that figure.

Jimmy Soni:

Yeah.

Gretchen Rubin:

But somebody told me, they said to me, “Gretchen, when most people read a biography, they want an authoritative account with some new information. And that’s not what you’re writing.” And it’s like, it’s not what I’m writing. It’s like I was writing a book that people weren’t that interested in.

Jimmy Soni:

It was more of an impressionist painting almost. Right.

Gretchen Rubin:

40 Ways. Right. So it’s like a Monet... the haystack painting.

Jimmy Soni:

Yeah. And then, you know, I have a million questions that could get into about the Churchill book. But the... one of the... I imagine a criticism or I imagine pushback that you could get is “Gretchen, I mean, the shelves groan under the weight of Churchill’s stuff...”

Gretchen Rubin:

Yes. No, Churchill himself said...

Jimmy Soni:

Exactly.

Gretchen Rubin:

That’s... that field has been plowed. I mean, even when he was still alive.

Jimmy Soni:

And he himself was prolific and...

Gretchen Rubin:

Oh my gosh.

Jimmy Soni:

So you’re competing against your subject and people who have written about your subject ad nauseam.

Gretchen Rubin:

Yeah.

Jimmy Soni:

For 50 years, 60 years. So how did you... did you have to deal with that, any of that?

Gretchen Rubin:

I mean, I... I dealt with it in the introduction. I just said, “Yeah, I get it, but...”

Jimmy Soni:

But your publisher still went for it.

Gretchen Rubin:

Yeah. And it’s just like... but there’s always a new way to understand him and his own account of himself. The biggest problem with the Churchill book was that Churchill himself is such an outstanding writer that I felt like whatever he wrote just jumped off the page. And then my stuff was like, “Eh, this is... yeah, meh.” So... but I learned so much as a writer from Churchill. Like, that was a thing I didn’t expect. It’s just like, because I would type out all these, you know, these... my favorite speeches and things that he would write, my favorite passages. And there was so much as a writer that would be a really fun book which is writing lessons from Winston Churchill because he was a master.

Jimmy Soni:

I think there is a book like Churchill as Writer.

Gretchen Rubin:

I’m sure there is. Right?

Jimmy Soni:

Churchill as Painter.

Gretchen Rubin:

Yeah. The wit and wisdom. No, I’m sure I probably have that. Yeah, yeah.

Jimmy Soni:

You made a really important point and it’s an interesting one for anybody who’s listening, who is a creative. And there are many that you... I... the way I’ve heard it described is you have to leave a reader-sized hole in your work. Right. So you never know... to what you said. You never know who is going to find your book and use it or treat it or think about it in a way that you’ve never anticipated. Right. So for you it was, “Oh, this is the gateway drug.” And it turned out to be actually... this is the... this is the finishing course for this particular meal.

Jimmy Soni:

I had a similar experience with my first book, which was about an ancient Roman senator named Cato. It was called Rome’s Last Citizen. And I remember thinking, “Well, I’m writing this for people who are super nerdy like me, really enjoy Roman history. They probably read about Caesar. They might have read about Cicero. This fits that spot on the bookshelf. Great. That’s the audience.” And it turned out that Cato was one of the patron saints of Stoicism. And Stoicism had a renaissance among different people. And people like Tim Ferriss read my book, loved it, let me blog on his site way back in the day and it took off among the sort of contemporary Stoicism set. Right. I heard a story about Michael Lewis when he did Liar’s Poker.

He said he thought he was writing kind of a message in a bottle for people to stay away from... to stay away from Wall Street. And what he got were hundreds of letters like, “I read your how-to guide for how to succeed on Wall Street. Like, is there other things you left out?” I do think you have to leave a reader-sized hole. Like it’s one of the challenging things actually about doing this work is when you see it misinterpreted or you see it kind of... and it’s not always a bad thing because if people are reading it, you’re happy. Right. But I do find that there’s a little bit of, “What about that little thing that I put in there that everybody missed that I was so happy about?” Have you had moments like that?

Gretchen Rubin:

Yeah, you have to let go of that. You have to let go of that. Well, it’s funny because in writing about happiness, a lot of times people will say to me, “Well, I know you wrote in your book, blah, blah, blah.” And I’m like, “I never wrote that at all,” you know, but I’m just like, if you brought that to it that’s fine.

Jimmy Soni:

That’s fine.

Gretchen Rubin:

You know, it’s because I think once people start thinking... one of the nicest things that anybody said to me about my work was somebody, it was either Better Than Before or The Happiness Project. They said, “I’ve never read a book about somebody else that made me think about myself more.” And I’m like, that’s exactly what I’m going for. But when people are reading a book and they’re trying to understand it for themselves, of course they’re going to start seeing things in the book that you never put there.

Jimmy Soni:

Never intended. And it’s actually also one of the... books are great randomness machines in this way.

Gretchen Rubin:

That’s a great... that’s a great way. It’s just throw a bunch of ideas. You know, when the student is ready, the teacher appears. But the question is, how do you put yourself in the place where the teacher can appear?

Jimmy Soni:

Right, right.

Gretchen Rubin:

Yeah.

Jimmy Soni:

And it’s... but it’s also one of the most gratifying. Like, I’ll... you get random notes from people about some little ingredient you included you didn’t think was a big deal or a footnote you threw... a stray footnote that ends up being a thing.

Gretchen Rubin:

Wait, can I tell you an example from our podcast? Okay, so I have the Happier with Gretchen Rubin podcast, which is my sister. So sometimes people would send in... and this is to the point of you never know what ideas are going to land deep with people. So somebody had written in and said, “I lost my engagement ring. It was really important to me. We can’t afford to replace it. I am just sick about it. I don’t know. I looked everywhere. I just can’t find it. I just can’t find it. And my question is, how do I make my peace with this? How do I find happiness when I have just so much... and I’m just so upset about this?” So the question isn’t how to deal with a ring.

The question is, how do I deal with the negative emotions that I have around the ring? So we had our own answer. Whatever. Then a listener wrote in and her answer... people to this day are like, “What was the episode where the woman talked about this answer?” We’ve returned to it several times because people just... it struck a chord. She said, “In Japan, we have the belief that a precious object might sacrifice itself for you, that to save you from a bad fate, it might lose itself.” And she said, “It’s totally a myth. But it might be help... comforting for her to think that this precious possession had lost itself to save her.” And to us, this was so strange because it’s just a reframing, right? Nothing in the... none of the facts have changed. It’s just the reframing in your mind.

And people to this day are like, “What episode was it where that woman talked about the ring losing itself?” There’s just something about it to just... and then I was in Japan and I was having some... I was with a guide and I mentioned this and she looked at me and she said, “It’s very Japanese.”

Jimmy Soni:

That does sound… you told me this story without cultural context, but that sounds Japanese.

Gretchen Rubin:

It sounds Japanese. And because the reader herself is in Japan. This is... we have this thought, but... so that was an interesting example where to us this was just like, “Oh, interesting insight from a listener in response.” And we... we have these all the time. And then it was just... it just reverberated for years. And sometimes you just don’t know. And I think for creative people, this is why sometimes it’s good to just throw a lot of ideas out there, because you don’t always know that you’ve hit a deep seam, because, like you said, there’s so many rabbit holes that you’re going down all the time. You know, sometimes it’s really... it’s really illuminating to think, “Oh, this is an idea that people are really... that somehow is really striking a chord.”

Jimmy Soni:

It’s also one of the reasons why I tell people, whether they are authors or just readers, to write in. Like, to tell the person who created the thing what specific things stood with you. Like, I just have that as a default habit now. If I walk around the world...

Gretchen Rubin:

Do you really do that with books you read?

Jimmy Soni:

With books I read, with statues I walk by.

Gretchen Rubin:

That’s so nice.

Jimmy Soni:

I remember I walked by Jane’s Carousel in Brooklyn, and I was so... my daughter was riding it a lot. And I remember thinking, “This is a really nice carousel, and it’s nicer...” and I could get in trouble for this. “It’s nicer than the Bryant Park, the SeaGlass, the Central Park one.” It’s the nicest carousel in New York. It’s very beautifully maintained. And so I started going down the rabbit hole. And I remember thinking... I was like, my habit is, I’ll find it, find the creator, write them some kind of note so that they know.

Gretchen Rubin:

This is such a lovely practice.

Jimmy Soni:

And it just became a default thing. But what’s great is I know how I feel when I get those notes. And so I wrote to Jane of Jane’s Carousel. One thing led to another, we became friends. And then I ended up doing the coffee table book with her about Jane’s Carousel. Because of that note. All because of that note. So I always tell people, if something strikes you, if it enters your life’s conversation in some way...

Gretchen Rubin:

Yes.

Jimmy Soni:

Let the person know.

Gretchen Rubin:

That is really...

Jimmy Soni:

Because then you and I don’t have any sense of what’s working or what’s not.

Gretchen Rubin:

We don’t. We don’t.

Jimmy Soni:

We have a vague sense, but not really a concrete sense.

Gretchen Rubin:

Okay. And here’s what I would add.

Jimmy Soni:

Yeah.

Gretchen Rubin:

There’s so much AI slop of all these AI agents saying all of these flattering things that it’s like, can I tell the difference between somebody who’s faking it and somebody who’s actually resonating?

Jimmy Soni:

100%?

Gretchen Rubin:

100%. Or even people are like, “I loved your recent podcast episode where you talked about...” I’m like, “Yeah, that’s fake.” Because I can tell when somebody’s really, you know, says, “Oh, I was thinking, you know, we have this...” But you can just sort of tell the difference in terms of how people are, you know. For 2026, one of the items that I wanted to do was to rate and review podcasts and books more, because as somebody who’s a creator, I know how much it matters. It just matters for the... for all these things, it really matters to people, and it’s gratifying, and... and I haven’t even really been keeping up with that as much. And you’re going way beyond that, which is to actually track down the contact information. But that’s so much more meaningful.

Jimmy Soni:

It is. It’s also... it’s not that hard to do. So here’s the way I think about it is...

Gretchen Rubin:

Also to sharpen your gaze.

Jimmy Soni:

Oh, absolutely. And the other thing is you know, you... everybody lives a life where you try, I think, on balance, to leave the world... hopefully you live your life this way... a little bit better. A little... just a wee bit better. Right. And you can do that in a lot of ways. You can raise your kids well. You can do creative work. You can just be a human. You can volunteer. And I do think that this is my way of the karmic scales.

Gretchen Rubin:

Yeah.

Jimmy Soni:

Like, I need to keep them in balance. And, you know, my work requires a lot of borrowing on karma from other people, whether it’s editors investing in you or time away from certain friends or... I kind of think of this as my way of restoring the karma scales. But then the other part of it is it’s not a long exercise. You know, I finished a book a couple weeks ago, and it took me, what, a minute or two of Googling to find the person’s contact info. I had two sentences that I wanted to say to them because there was one chapter that really stood out to me. Drop a note. Send it off. It’s not like I’m not laboring over this for years and years. This is just very quick.

Gretchen Rubin:

So keep it easy.

Jimmy Soni:

But keep it easy. And also, it then sort of puts you in the position of, I may never have contact with that person again. Ever again. But they know that something that they spent years on had some kind of effect in the world. I think that’s one of the things that, you know, it’s... you do spend years of your life on these projects. And I’m sure, especially when your first few books came out, anytime anybody wrote you, it was the greatest. It was the greatest moment ever.

Gretchen Rubin:

No, it really was.

Jimmy Soni:

I think you can be world famous and these things still affect you. Right? Like, you can have fans galore, but it’s somebody identifying something specific in your work that still makes a massive difference. A massive difference.

Gretchen Rubin:

No, I think that’s really true. And I think there is something about putting out those... the appreciation for people’s efforts..

Jimmy Soni:

And I would say that it extends as well... as I said to physical things or a product you really love or... it doesn’t have to be a book. It doesn’t have to be some... some work of art, it can be something very simple. I also find the other effect of this. It gets you to find the origin story of the thing itself. So you... because you look at something and you’re like, “I really like that.” You have to then go dig and figure out how did this thing come into being. Right. And for people who love rabbit holes, that’s catnip, you know, there’s nothing like that feeling. How did you... just... because I want to be conscious of your time. How did you go from JFK and Churchill to The Happiness Project? What is the origin story? The kind of, you know, pre-story on The Happiness Project?

Gretchen Rubin:

Again I have been... I know exactly when and where it happened. So I was finishing up... it was probably just after first pass with my JFK book. So I had this... and at that time, because writers didn’t have all this other stuff that we were doing, there is kind of a period of inactivity because you can no longer actively edit, as we were saying, and they’ve ripped it out of your cold hands. And the book hasn’t been published yet. So there’s kind of this... and for me, it was... so I just sort of had this open time in my head. So it was during that period and I was stuck on the crosstown bus on 79th in the pouring rain. It was going really slowly and I didn’t have anything to read or distract myself with. And I just...

I looked out the window and I thought, “What do I want from life anyway?” And I thought, “I want to be happy.” But I... and I thought, “Well, but I don’t spend any time thinking about whether I am happy or if I could be happier or what is happiness anyway?” And I thought, “Well, I should do a happiness project and figure all this out.” So... and I instantly became super interested in the idea of happiness. So I ran to the bookstore and the library and got a giant stack of books. Stoics, you know, novels, nonfiction, research. This was right at the time when sort of the positive psychology movement was just getting going. So there was a lot of interesting research that had just kind of emerged at that time. And at first it was just...

For me, it was just like, what do I... what could I do to be happier in my own life? And... but as I got into it, I just... my note taking, my research got deeper and deeper, and there were so many things that I wanted to learn and so many things I wanted to try in my own life. Yeah. That I thought, “Oh, maybe this could be my next book project.”

Jimmy Soni:

Yeah.

Gretchen Rubin:

And then I’ve sort of been writing about happiness one way or another ever since. And it’s funny because I don’t know about you for titles, but for me, titles either come right away or extremely slowly. And people, many people, said, “You shouldn’t call it The Happiness Project because that sounds like homework. Nobody likes to do it.” And I was like, “But I love homework. I love...” No, I love a project. Homework for long periods of time. Seriously, give me a course. I’ll sit down. I love a curriculum. But... but I was like, but that’s... that’s... it was... I was like, it... just from the very first minute, I had this idea it was The Happiness Project. Yeah. Yeah.

Jimmy Soni:

That’s great.

Gretchen Rubin:

Yeah.

Jimmy Soni:

Did you have trouble selling it at all, or was it a pretty easy sell after... because you said JFK didn’t do well.

Gretchen Rubin:

No, it was not an easy sell. First of all, I was talking to people about it, and they didn’t get it. Like, somebody’s like... because I was like, “Oh, yeah.” I kind of mentioned Benjamin Franklin. Because if you’re talking about, you know, he’s, you know, OG in this... in this space.

Jimmy Soni:

No, he is. He’s the Godfather.

Gretchen Rubin:

Yeah, he’s the Godfather. And they would be like, “Well, maybe you should do a thing where you follow all of Benjamin Franklin’s rules.” And I’m like, “No...” This was a time when doing sort of what... what you could dismissively call stunt nonfiction was... was more and more. And so kind of the...

Jimmy Soni:

The more august name. Right. Was the gonzo journalism a long time ago.

Gretchen Rubin:

Exactly, exactly right. And so, yeah, everything just keeps being reinvented. Auto-fiction, it’s like, yeah, they’ve been doing that for a long time. No, so first people didn’t really get it. And that’s part of why I thought, I think I just have to really write a lot of it because people aren’t understanding and this wasn’t me officially pitching it, but just more me casually talking to smart people to sort of pick their brain and they just... they just weren’t responding the way I thought that they should in my vanity. So I basically wrote a huge thing and then my agent was just like, “Yeah, it’s not good.” And then I wrote it again and my agent was like, “Yeah, I’m sorry, it’s just still not good enough.”

And then... and then I kind of figured out how to break it. And then... and then that’s when I went out. And then there was a reasonable amount of interest. But not like wild enthusiasm.

Jimmy Soni:

Not enthusiasm commensurate to what the book eventually became.

Gretchen Rubin:

No, not at all.

Jimmy Soni:

Because now that’s your best known...

Gretchen Rubin:

For sure. Yeah, I mean it was, yeah, it was number one. It was on the list for two years. Yeah, no, it was... no, nobody... but the one thing that I had done so I had a blog that I had been doing for years, a daily blog. And I did it because when I was writing the book, one of the arguments that I was testing, because it was all a test on me, all self-experiment was novelty and challenge make people happier. And I had thought, “Well, I’m not that kind of person. Maybe that’s true for most people, but I like familiarity and mastery.” But I had to test it for the purposes of the book. So I decided I would start a blog because I’m like, “This is novel, this is challenging. I don’t know tech, I don’t write for deadlines.”

I’ve never been a journalist. This is going to be really hard and, but I’ll do it and just sort of report. And I thought, “Oh, I’ll do it for a month.” But then it really worked. And so I was fortunate in that at that time, not that many people had done something like that, which is to create an audience for a book before the book was published. And use it as a way to try to get people interested in a book. Now of course, preorder campaigns are a huge thing. And people are constantly talking about this thing. But at that time it wasn’t as common and I didn’t do it strategically and cleverly. I did it accidentally and for my own reasons. It just sort of ended up that way. But I think that was something that made... that really helped.

Jimmy Soni:

I want to bring things kind of... wind things to a close, but I, you know, we talk a little bit about your writing habits. You write in the mornings.

Gretchen Rubin:

Well, I write all day, but I write hard things in the morning.

Jimmy Soni:

And so how do you, yeah, how do you structure your creative life now? Like what’s... what is a typical week, a day and then a week kind of in your life look like.

Gretchen Rubin:

So in my dreams, I’m a Benedictine monk and every day is exactly the same and I know exactly what I’m doing at 10am every single day. But it’s not like that because now I have a podcast... I have podcast Happier with Gretchen Rubin, I have a newsletter, I have a newsletter in Klaviyo, I have a newsletter on LinkedIn, and I have a newsletter on Substack, all of which are different. I do social media, I have products, I do speaking. So I... so the one thing that I… I go to the Met every day...

Jimmy Soni:

Right yeah, which is probably one of my favorite things in Life in Five Senses.

Gretchen Rubin:

Part of my creative practice. So as much as I would love to have a very routinized life, I can’t because it’s just... it’s just, it’s constantly, I have to constantly shift things around. And I think that’s one of the reasons why I like to do my hardest reading first thing in the morning is from 5:30 to 9. Rarely changes. I... except for walking my dogs. That is very much... I can count on that. And then everything else, it’s like, I may or may not be able to do it. I might not be able to do it until 4pm by which time I’m not at my best. I might only have an hour. Instead of having a big block. One thing I have learned to do is not to have a big block. I think when you’re starting out in writing, you’re kind of like, “I have to have a whole day or I have to have half a day.” And now I’m like, I have all kinds of writing tasks and some of them I can do if I... I’m just sitting down for a few minutes.

Jimmy Soni:

So does the morning time always go to the biggest, most important project? Is that what you try to do?

Gretchen Rubin:

Yes, that’s what I always try to do.

Jimmy Soni:

And do you miss that? Like, do you... do you miss it when you’re on the road? Do you sort of give yourself breaks, or is it seven days a week?

Gretchen Rubin:

I try to do it seven days a week.

Jimmy Soni:

Wow okay. Yeah. That’s great.

Gretchen Rubin:

Because it is just so precious to me. Yeah. Yeah.

Jimmy Soni:

Look, I’m...

Gretchen Rubin:

But I’m rigid. Yeah.

Jimmy Soni:

You know, I’m rigid in the same way. And honestly, I feel off on the days I don’t have that.

Gretchen Rubin:

It doesn’t feel like... it doesn’t feel like a treat.

Jimmy Soni:

Yeah. It feels like the way I described it to friends. It’s like, if I don’t have that time in the morning where I’m doing a... whatever the creative or editorial or writing task is, that’s the most important. It feels like I didn’t brush my teeth.

Gretchen Rubin:

Yeah, no, that’s... it’s such a good analogy. Exactly.

Jimmy Soni:

Something is off…

Gretchen Rubin:

It’s not that it’s really a big deal or that it matters in any kind of way or that anybody else cares, but you just feel...

Jimmy Soni:

Just feel off.

Gretchen Rubin:

Yeah.

Jimmy Soni:

And then those grooves, they get... they get to be the place I’m happiest. Right. Is when I’m in that... that particular groove.

Gretchen Rubin:

Yeah.

Jimmy Soni:

Do you... have you ever tried to change up the schedule or has this been the schedule for time immemorial?

Gretchen Rubin:

I haven’t always been able to get up this early. And when I had little kids, of course, I had much less control over my mornings. So then I... but at that time, I had fewer other commitments. You know, I didn’t always have the podcast. I didn’t always have the newsletters. I didn’t have... it just... I feel like as a writer, the kinds of work that you might do just as part of your ordinary writing life have really expanded. So I feel like I was fortunate that when my kids were younger and they were taking up a lot of my sort of unpredictable time and predictable time. I was just more focused.

Jimmy Soni:

When do you read? If you read?

Gretchen Rubin:

I love to read. This is a huge question in my life, it is a huge mystery because I read books, at the end of the month, I have the stack and I post a picture of it. And these are the books that I read. And I see that I read books. I’m always like, I feel like I’m never reading. I’m constantly fighting to find more time to read. My favorite thing is the same day book where I start and finish a book in the same day.

Jimmy Soni:

That’s where my...

Gretchen Rubin:

So delicious. I love that feeling. I have to do a lot of work for reading. If I’m doing work reading, I’ll do that during a work day. Kind of at the end of the day when I’m tired. If I’m just reading for pleasure, then I feel like I have to read it in sort of my leisure time. But... and I... I feel like I’m not reading nearly enough. For the podcast, we always have a challenge tied to the year. So 25 for 25 was read 25 in 25. So you had to read 25 minutes a day?

Jimmy Soni:

Oh, 25 minutes a day.

Gretchen Rubin:

Yeah.

Jimmy Soni:

Okay.

Gretchen Rubin:

That... and that was... yeah, I... I just, I don’t know. How do you get enough reading done?

Jimmy Soni:

It’s hard.

Gretchen Rubin:

It’s... it’s something that’s very easy to find... push to the bottom. You have to fight for it.

Jimmy Soni:

You have to fight for... what I do, you know, part of it, I think... and this is sort of occupational hazard. I read... I am reading always, somewhat opportunistically. If I’m in the middle of a book project, I’m reading things that are tied to the thing I’m writing. So I feel like it’s real work. Right. So then I always have a reason.

Gretchen Rubin:

But does that feel different. Oh, yeah. That’s... that’s a different category.

Jimmy Soni:

There were years when I actually... I talked to a friend about this the other day, that I, at one point, I lost the ability to read for pleasure. I was... I... because you write books and you’re obsessed with books and you’re working on books all the time, and all of a sudden I wake up and I’m like, “I don’t actually enjoy reading anymore.” So I had to go back and start with fiction again and revive my childhood love of reading and wonder. The wonder of discovery. I lost all of it because it was all so utilitarian now.

Gretchen Rubin:

Exactly.

Jimmy Soni:

And then I would say, I... I try to do... if I... if I’m going on vacation, I try to take only novels and I’ll read stuff that has nothing to do with work. Right. But it’s actually hard. It’s actually hard to carve out. There was a period where I was trying to do 15 to 20 minutes every morning before anything else. That lasted for several months, and I finished a bunch of great books in that process. But I... it’s a challenge. Like, I... I will find that... actually, one thing that’s helped is my daughter has 30 minutes of required reading time every day for school. I just read side by side.

Gretchen Rubin:

Yeah, that’s a great...

Jimmy Soni:

So it’s like...

Gretchen Rubin:

That’s a great...

Jimmy Soni:

That makes it actually very easy.

Gretchen Rubin:

Because you have that accountability. One thing a friend of mine told me, and I’ve completely followed this, is that when she’s traveling for work, she reads for pleasure. So she never tries to work on a plane or review a document or something. It’s like, if you’re traveling for work, you just read for fun. And she’s like, that way, you know that you have that time and it’s just the most delicious. I love reading on airplanes because you’re just so focused.

Jimmy Soni:

Yeah, no, I finished... I finished a number of books on airplanes that I wouldn’t have finished in any other form or because you always feel like you’re robbing Peter to pay Paul.

Gretchen Rubin:

Right.

Jimmy Soni:

It’s like, do you work on the Substack or do you read? Do you work on X or do you read? Right. And I find that the other... the other bit, for me, it’s much more around choosing books. If it’s in project mode, I’m choosing books that I have to read anyway. Hopefully they’re enjoyable. But if I am, I try to portion out vacation time and choose my books there so that it’s pure pleasure.

Gretchen Rubin:

Pure pleasure, yeah. I think people don’t sometimes expect enough. Put down a book that’s not good, find something that’s really... then what I often do is I’ll pick a book. I’ll pick something to read for the summer to give my summer a theme. So I had a summer of Proust, because I had never read all of Proust. I had a summer of rereading, because I love to reread. And there were a bunch of sort of difficult books that I wanted to reread, like The Varieties of Religious Experience. I’m like... I’m like, when am I going to reread that? So I’m like, “Okay, I’ll have a summer when I just reread these books.” And then my summer this year, which will start June 1, is the summer of Virginia Woolf’s diaries. Because I love Virginia Woolf. She’s my favorite author.

But I have never read her diaries, which are extensive. And I’m like, when am I going to get around to that? Like, I had to turn it into sort of a project. So... so that’s what I’m gonna... so that’s... so I will often do that with the summer if there’s something that I kind of want to tackle. Yeah, that’s how you’ll tackle it. Yeah. Yeah.

Jimmy Soni:

So one of the ways all Infinite Loops episodes end with this question, which is, you’re made emperor for a day. Which, by the way, I actually think you’d make a great emperor.

Gretchen Rubin:

Thank you.

Jimmy Soni:

Like, if you ever... you ever decide to campaign for that office, let me know, because you’ll have my vote. And you... you have a magical microphone. You’re allowed to share two ideas that everybody in the world will wake up, and those two ideas will be implanted in their minds, and they will... they will believe that they are their own. Right. They’re not coming from Emperor Gretchen. They’re coming from their own psyche. And they... people live by and adhere to them. What... what are those two... you’re... you’re somebody that’s thought about this question extensively across...

Gretchen Rubin:

I’ve never thought of it in this iteration.

Jimmy Soni:

What are the couple of... Couple of ideas?

Gretchen Rubin:

I would say, know thyself and do unto others as you would have them do unto you. I think that could go pretty far.

Jimmy Soni:

Yeah. So on the know thyself, that’s been your life’s work, right?

Gretchen Rubin:

It’s on the Temple of Apollo at Delphi. Yes. Yeah.

Jimmy Soni:

Is that... is it fair to say that your work is kind of an extension of that question?

Gretchen Rubin:

Yes, I think that’s a... I think that’s... yes.

Jimmy Soni:

I think that’s why it has resonance. Like, it’s... it’s why even...

Gretchen Rubin:

It’s a great challenge of our lives. Yeah.

Jimmy Soni:

And in the intro to Life in Five Senses, you write about how this is... these books are very personal for you.

Gretchen Rubin:

Right.

Jimmy Soni:

That one seems to be the most personal. You have this kind of moment. And I won’t spoil it, because I think people should go check out that book. But you have a moment that leads you down these rabbit holes. It’s about knowing yourself.

Gretchen Rubin:

Yeah.

Jimmy Soni:

And the other one is do unto others…

Gretchen Rubin:

As you would have them do unto you. And you can quibble and you can say, “Well, but sometimes they don’t want you to do unto them. They want you to do unto them the way they want it to be done unto you.” I was like, start from there. Start from there.

Jimmy Soni:

Amazing. Well, Gretchen Rubin, you are... you remain... and you are one of my favorite authors. I love your work. I want everybody to check it out. Where can people find you? And just give us... give us the list so that we have...

Gretchen Rubin:

GretchenRubin.com. It’s all... everything’s there. Yeah, yeah.

Jimmy Soni:

Okay.

Gretchen Rubin:

Yeah. Oh, this is... this is such a pleasure.

Jimmy Soni:

Thank you for coming on. Thank you for taking the time to do this wonderful work and until next time.

Gretchen Rubin:

Until next time.

Leave a comment

Subscribe now

Share

We’ve shared some highlights below, together with links & a full transcript. If you like what you hear/read, please leave a comment or drop us a review on your provider of choice.

Links

Apple Podcasts

Highlights

Finding Peanut Butter and Jelly Stories

Ben Cohen: And so that’s something else that I learned covering sports at the Journal is that I think there are two ways to tell stories. One is taking small ideas and making them really big, and one is taking big ideas and making them really small. In some ways, they’re connected. But, for example, we always used to look for funny, interesting, peculiar, clever ideas at the Wall Street Journal. So one story that I wrote was, in 2016, the Golden State Warriors started the year 24-0. They were 41-4 at one point. There was nothing that was going wrong.

And as a journalist, you’re always looking for tension. Tension is what makes a story. And when there’s no tension, it’s like, well, what do you do with that? And I remember listening to a bunch of radio interviews the Warriors were doing at the time. You know, probably the only person outside the Bay Area who was actually listening to interviews on local radio. And in one of them, the interim coach at the time, Steve Kerr was on medical leave. And the interim coach at the time was Luke Walton. And he was doing this interview as he was walking off a plane, and they were saying, “Luke, what’s going on? How are you doing?” He was like, “I’m terrible. The team trainer before the season got rid of our peanut butter and jellies on the team plane because he thought they weren’t healthy. And everyone is completely miserable about it because all NBA players famously eat, they just subsist on peanut butter and jelly. It’s just around at all hours.”

And I heard this, and I was like, “Okay, well, the story to do is that the greatest source of tension in the locker room in Golden State right now is they’re fighting to get their peanut butter and jellies back.” And so that’s a funny idea for a story. And then you take it to the extreme. And they happened to be coming through the East Coast a couple of days later. I remember I went to Philadelphia and stalked their locker room and went quietly to every player in the locker room and asked, “What do you make of the war over peanut butter and jelly in the locker room?” having sotto voce conversations with Steph Curry in the side of the room. Then the next day, they were in New York, and I went to the Garden, did the same thing. And over time, you’re reporting, that’s hours and hours of reporting to ask players off to the side to get an exclusive about peanut butter and jelly. And so you could tell sort of the story of the Golden State Warriors’ magical season through the only thing that has gone wrong for this team is peanut butter and jelly.

And so I’m always kind of looking for peanut butter and jelly stories in all sorts of industries. And one other thing I’ve learned through the course of writing this column is that if I find something interesting, the chances are that I can convey that interest and enthusiasm to readers. And if I don’t know something that it feels like everybody else knows or should know, then the chances are that they don’t know it either. And, you know, I find myself thinking a lot, “Well, does everyone know this? Or am I just an idiot and just found out for the first time?” And I think a lot of people don’t know a lot of things. And so things that you would think that everybody knows, they don’t know, and I didn’t know them.

And so I’ve learned to kind of trust my judgment and gut about that a little bit. If I think something is interesting, I can convey that interest and I can make other people interested in it as well.

Sam Walker: Evil Genius

Jimmy Soni: Can you talk a little more about Sam Walker and the effect that he’s had on your career and your life and the way you write and all of that?

Ben Cohen: Yeah. Sam Walker. There are a lot of people who came up through the Wall Street Journal sports section then, and I think they would all credit Sam for sort of being the evil genius voice in our head. And Sam is a brilliant writer himself. One of the reasons why it was okay that Sam was rewriting you was because he was just such a better writer than any of us were, that you would read it and be like, “Well, I would never say this…”

Jimmy Soni: But it’s said way better.

Ben Cohen: The fact that my name is on these words is actually great.

Jimmy Soni: Yeah.

Ben Cohen: And just a diabolical genius. He had just such smart and clever and inventive ideas and ways of reporting and writing and just making sentences sing. And his voice is constantly in my head. And so one of his rules for writing and especially finding stories was that the lead quote in any story that we wrote, which meant that the idea had to be so clever and so novel that the lead quote could have been, not that it should have been, but could have been, “I’ve never seen anything like this before.” And that was what we aspired to every single time. And so we were always looking for ideas that could be, “I’ve never seen anything like this before.” And the highest form of praise is when Sam would just write back in an email, “Yes,” with eight exclamation points and weird bolds and yellow highlights and that praise and affirmation is still, I should just print out those emails because they still mean so much to me.

Transcript

Jimmy Soni: Ben Cohen, thank you for coming on Infinite Loops.

Ben Cohen: Thanks for having me.

Jimmy Soni: Yeah, I’m really excited about this. This has been something I’ve been looking forward to for a while because I’ve been a fan of your work for a long time. I think you cover the widest range of things that somebody I know writes about. It is everything from the pants at Costco to sports to why the fuel indicator on your car goes a certain way. I have yet to meet somebody that covers a range of things that you write about.

Ben Cohen: All the important things in the world.

Jimmy Soni: Exactly. I’m excited to have you here and we can just dive right in and see where this all takes us. One of the reasons we’re having you on is you’re an author and you have this side hustle at the Wall Street Journal. But I’m curious, take us back to how did you get your start in writing? Thinking about it as a vocation or even as an avocation.

Ben Cohen: Some kids grow up wanting to be astronauts. And for some reason I just always wanted to be a sports journalist. I have no idea why, but I very vividly remember reading the sports section of my local newspaper every morning growing up and going through the box scores and then eventually knowing who the columnists were and reading every piece and having it dawn on me that people actually do this for a living and that I could do it too, if I wanted to. And so even when I was in middle school, I wanted to write about sports for a living. I didn’t know anyone who did it. I was randomly emailing people who wrote for the Star-Ledger in New Jersey and was starting to write into the newspaper letter section.

So every day in the Star-Ledger, they would ask a question about something happening in sports at the time. And I would just write in and I would have my name and my writing in the local newspaper. So no one knew that Ben Cohen: from Livingston, New Jersey was 10 years old weighing in with hot takes about the Yankees.

Jimmy Soni: How often did you get published in the Star-Ledger as a 10-year-old?

Ben Cohen: Frighteningly often. Yeah. Which I think may have something to do with the fact that I may have been the only person writing in. But they would ask a question and they would print between 8 and 15 responses and they would run them throughout the course of the week. There’s probably a different question every week. So I feel like if you went through the archives of the Star-Ledger, you would find my name in there dozens of times.

Jimmy Soni: Wow. And that was your first byline?

Ben Cohen: I think it was my first byline, yeah.

Jimmy Soni: Awesome.

Ben Cohen: And so I was always obsessed with it. And I was writing for my high school newspaper, and I would watch games and then go up to the computer room in our house, remember computer rooms in a house, and would try to bang out columns on deadline and they’re horrible. And then I really started writing for a newspaper for the first time when I got to college. And at that point, we had gone from growing up and wanting to be astronauts or doctors and lawyers to consultants and I-bankers. And that just never interested me. From the second I stepped on campus at college, I knew I wanted to be a journalist.

And probably that wasn’t the greatest idea financially or for my mental health or anything, but it was all that I wanted to do and kind of all that I can do. And so I feel very lucky that I’m actually able to do it now.

Jimmy Soni: That’s amazing. I didn’t know that part of your story.

Ben Cohen: You weren’t familiar with the sports archives in the 1990s?

Jimmy Soni: Yeah exactly, I should have done more homework. When you think back on that time if you can, I mean, it might be impossible, so much time has passed. But do you remember the first thing you got published? Was it a thrill from the job?

Ben Cohen: Yeah, always. I mean, at that point, getting published was not looking at my phone or something in pixels. It was literally going outside on the doorstep where the Star-Ledger was in a yellow newspaper bag, opening it up, having no idea if my response was going to be in the paper that day. It wasn’t like they emailed you and said, “Oh yeah, you’re going to be in the paper tomorrow.” So every time I wrote in, I would frantically open the newspaper and go to the second page and say, “Oh, is this a day that I’m in the newspaper?” And I sort of felt that way throughout.

I remember I played sports in high school and I would always be curious, our baseball game yesterday, who are they going to pull out and put in the paper? So that thrill of being in the paper was familiar to me from a young age. And I still feel that way. I don’t have that. I know when I’m going to be in the newspaper now, so it’s not as thrilling, but it’s still very cool to be able to open a print newspaper, a thing that still exists, and say, “Oh, my God, there’s my name.”

Jimmy Soni: Did your parents think you were a savant or did they see a child prodigy in you because you’re getting these published?

Ben Cohen: I don’t know. I think they thought it was cool. I think they saw that I was passionate about it and they pushed me towards it and did not deter me from trying to be a newspaper journalist when maybe they should have. So I don’t know what they imagined for me. I don’t know if it was astronaut or investment banker, but I landed somewhere in another galaxy.

Jimmy Soni: How did you choose? You and I share the august fact that we’re both Duke alumni.

Ben Cohen: Not supposed to tell people.

Jimmy Soni: Not supposed to tell people. All right, first rule of Fight Club. What made you choose Duke? Out of curiosity? Because it’s not the natural place for somebody who’s going to. It’s a more natural place for somebody who’s going to go become a banker or a consultant, not a journalist.

Ben Cohen: I would argue that it’s quite a natural place for a boy from New Jersey who likes basketball to end up, maybe the most natural place in the world. But no, I mean, it is a fantastic school, as we both know. And I was obsessed with the basketball team forever. I mean, I can say that I was also obsessed with the UNC basketball team from a young age. But I remember, I think like most kids who end up touring that school, I sort of went through the tour and braved the whole thing and was just sort of counting down the seconds until we could cross Tower View Road and get to Cameron. Because that was the place that I wanted to check out.

And so the idea of going to Duke and going to basketball games, much less being able to sit at center court and write about those basketball games, would have been just a total dream to 10-year-old me writing into the Star-Ledger.

Jimmy Soni: Did your work there, you were already bitten by the bug and this just made it go viral, right?

Ben Cohen: Yeah, it was full infestation when I was at Duke. So I wrote as a freshman and a sophomore. As a junior, I was the sports editor of the Chronicle, which is Duke’s newspaper. And that was my full-time job and major. I technically majored in English at Duke, but I majored in the Chronicle. The Chronicle had a program where the top editors took a reduced course load. So I think my junior fall, which was the big time when I was spending 80 hours a week in the office of the Chronicle, I took two courses and an independent study. I think I was in class for two hours a week and I was just putting the paper to bed at 3 a.m. every night, every day, a daily print newspaper. And this was at a time that you remember.

You would kill time before class by opening up the newspaper in print and reading it in the classroom. And by reading it, I mean you would do the Sudoku and crossword in the back with a pen. But we didn’t have iPhones then. We had sort of had flip phones and then Blackberries. The iPhone came in the middle of my college experience. But it wasn’t ubiquitous at the time. It was a real thrill in the same way that it was gratifying and thrilling and super exciting for me as a 10-year-old to be able to see my name in the print newspaper.

It was so cool to be in a lecture hall and see people reading the thing that I had written in a delirious state the night before that morning in class. It is the closest thing that there is to community newspaper where you are surrounded by your readers of that community. So I knew that my fellow students were reading it. I knew that professors were reading it. I knew that Coach K was reading it. It’s an awesome power and responsibility for a 19-year-old who has no idea what he’s doing to be read by everyone who is with you on campus. Which I just found super cool.

Jimmy Soni: That’s, I couldn’t have put it better myself. I did a column when I was a senior and I remember spending so much more time on that column than I ever did on actual schoolwork. I was trying to make it into something memorable. Meanwhile, these papers actually count for something.

Ben Cohen: Yeah, but when you write a paper, one person reads it.

Jimmy Soni: That’s true.

Ben Cohen: And when you write a column, you have no idea who’s going to read it or why or when or what effects will come from you having written that column. And so there’s much more pressure and responsibility, I feel, in being able to say something novel and interesting and engaging. And that’s still what I’m doing today, which is fun, but there will never be a feedback loop, I feel, the way that I had.

Jimmy Soni: Do you have standout moments from that time in your writing life? A piece or a particular thing you did that you’ll never forget?

Ben Cohen: I mean, a lot. Yeah. Covering basketball games. One of the great privileges of being the sports editor of the Chronicle is that my junior year, I covered the Duke-Carolina game. So a game that, as you know, kids will literally camp out in tents for months for attendance. I sort of waltzed in two hours before, and I feel like I made a point of getting there really early that day, before the arena opened to the public and just sort of sitting in this hallowed ground, silent. I vividly remember John Scheyer was warming up. He was the first person out there. And John was my class at school and is now the head coach of the basketball team, which is a very weird thing for me.

But just thinking about it now, I sort of have goosebumps because I’m like, when else am I going to be in Cameron Indoor Stadium before the biggest game of the year?

Jimmy Soni: That’s right.

Ben Cohen: But there are all sorts of moments like that. I remember when I was sports editor, Duke hired a new football coach named David Cutcliffe, and nobody knew anything about him. And I sort of made it my mission to profile him in a lot of interesting ways and dig up interesting moments from his past and got lots of time with him over the course of that year in a way that I’m sure he wasn’t expecting to be spending time with a student reporter over the course of that year, but these little vignettes from his past.

And it kind of reminded me, my first introduction in looking for new angles into stories that everybody else is covering, which is what I’m still doing today, and that if you put in the work, then people will respect it, even if you happen to be a student reporter and the person you’re trying to get the respect of is the head coach of a college football team.

Jimmy Soni: Yeah. You know, this is a specific question that it’s not anything I would ask any other guest, but did you ever have attention in writing objectively while also being a fan? Because you are a student and you’re there. Are you allowed to cheer? What are the rules?

Ben Cohen: Definitely not when you’re on press row.

Jimmy Soni: Right, of course.

Ben Cohen: But it’s a very, it’s one of the stranger parts of that particular job, and it’s something that I really don’t have to deal with now. I did write about Duke a little bit for the Wall Street Journal, but even then, you’re not a student at Duke. But I think that there is, I think some of the rules of objectivity in that sense have kind of loosened a little bit. And they were loosening at the time. There’s no pretending that I’m not a Duke student. And sometimes you would go all the way the other way and be more critical because you cared more deeply. I would imagine that I had much more nuanced and complex views about Mike Krzyzewski when I was a student at Duke than I would as an alumnus, because you’re just around it all the time.

You have such high standards, and you’re crazy, and you’re sleep deprived, and you think you know everything and you’re on top of the world. But I was a senior when they won the national championship, and I wanted them to win the national championship. I wasn’t objective about this fact.

Jimmy Soni: No studied objectivity in the chase for the championship.

Ben Cohen: There was not. In fact, I did not cover the national championship, and I did not go, partly because it wasn’t my turn to cover the team when they went. But I faced this choice when I was a senior of do I want to go to Indianapolis to watch them win the national championship or play for the national championship, or do I want to stay on campus? And I thought, hopefully there will be another chance to see a Duke team win a national championship or play in the Final Four. But I’ll never have an opportunity again to be on campus as a senior with my friends when they’re playing in the Final Four. And so I stayed on campus, which I still insist was the right decision.

Jimmy Soni: So fast forward. You finish up at Duke, how do you wind up doing journalism as a profession?

Ben Cohen: Blackmail. Yeah. No. I applied for an internship at the Wall Street Journal, and I didn’t get it at first, which is one of those sliding door moments, because I’m not quite sure what would have happened otherwise. So I applied.

Jimmy Soni: Are you a senior at this point?

Ben Cohen: Senior, yeah. And I had this really great conversation with the sports editor of the Journal at the time, and it turns out he had already offered the internship to somebody else. And he had seen my application at the bottom of a packet and thought it looked interesting for a whole bunch of reasons and called. We had this great conversation. He was like, “You know, this is all great, except I’ve basically offered this internship already to someone.” And I was like, “Well, that’s too bad.” And then the first week of May in my senior year of college, I got a call from the sports editor of the Wall Street Journal, who said, “The person I offered the internship to, who had taken it, just took a job at the Washington Post. So this internship is opened. Are you doing anything this summer?”

And I was like, “I’m not. I have nothing else.” I literally had nothing else lined up. I didn’t know what I was going to do. I was going to stay in Durham and just sort of bum around and try to pick up clips. And he was like, “Can you start in two weeks?” And I was like, “Okay, sure.” So I moved up and got an internship at the Wall Street Journal. That was 10 weeks, and I sort of kept my foot in the door. And I’ve been there ever since.

Jimmy Soni: Wow, okay. So you’ve had one employer after graduation. What was that first? Was it a baptism by fire, or was the Chronicle harder than the internship for the Wall Street Journal?

Ben Cohen: The Chronicle is very difficult in its own way. No, the working for the Wall Street Journal for the first time, trial by fire is one way to put it. I remember the first time I filed a story to the sports editor, who is this completely brilliant editor, and really was so formative in so many ways for me. I filed this piece to the editor and a couple other people underneath him, because that’s how we filed stories back then. I remember I filed the story and a couple other editors walked over to my desk and they were like, “This looks great.” And I was like, “Oh, great.” And they were like, “Whatever happens next, don’t take it personally. It’s going to be okay.”

And I was like, “Okay.” And then two hours later, I got back a rewritten version of the piece that had, I think, my byline on top of it and no other words that I had written. And it was just a complete top-to-bottom rewrite. And I was like, “Okay, I guess this is how it’s going to be.” And that really drilled into me what the standards and quality of a Wall Street Journal piece had to be at that time.

Jimmy Soni: Interesting. And did that keep happening? Or did the rewrites get a little less substantive as you went along?

Ben Cohen: They definitely got less. But the first editor I worked for at the Journal had just insanely high standards. And at the time, we only ran one story a day in the sports section. And there were probably between eight and 12 reporters. And so everyone was battling for that print space. And so the bar to get a story into the paper was, you had to be like Mondo Duplantis to clear it. It was so high, and the reporting had to be so deep, and the idea had to be so novel and inventive. And at that time, the nice thing about really the super fortuitous thing about writing for the Wall Street Journal sports section back then, I joined it in 2010. The Journal didn’t have a sports section until 2009, which is kind of remarkable if you think about it.

If you would think, what topic would Wall Street Journal readers be interested in? You would think sports would be at the top of the list. But we launched a page for the first time in print in 2009, and what that meant was that there was no legacy or baggage of, we’ve covered sports this way for 150 years. And so there’s going to be box scores and there’s going to be game stories. And this is how we’ve always done it. And so this is how we will continue to do it. We had to invent that on the fly and think, how should we cover sports today?

And the formula or the model that the founding editor, Sam Walker, came up with, was that a story that runs in the Wall Street Journal sports section not only can’t run in any other section, but hasn’t run in any other section. So if you think about the way that a lot of journalism works now, it’s like finding, everyone sort of writes the same story over and over again. And if one person writes a story and it does well, then lots of other outlets will write that story. We were always looking for clever angles into news, and we were looking to break news. So there are lots of ways to get exclusive stories that nobody else is writing. You can have some incredible investigative piece and turn up news that nobody else has.

You can write a piece in a completely different way that makes it stand out from everything else. You can collect data, you can analyze data in a different way. You can create the data yourself. You can be funny in an industry where nobody attempts to be humorous. You could just call a million more people than anyone else is going to call. You can look for ideas in different places. And so whenever we had space in the page, which is every day, we had to fill it with something that couldn’t have run anywhere else and hasn’t run anywhere else. And that was the challenge on a daily basis.

And so when I learned what journalism is, I learned it first from the Chronicle, which was its own form of journalism, and then from the Wall Street Journal, and specifically this pirate ship off of the Titanic of the Wall Street Journal that was just trying to be creative and inventive and interesting and give people something that they didn’t know that they wanted, but that they did want every single day.

Jimmy Soni: Yeah, do you remember your first piece that ran in the Journal? The first piece where you felt you met the bar?

Ben Cohen: Well, the first piece and the first piece where I felt I met the bar, probably different. One of the pieces that ran, I started in the summer of 2010, and it was a World Cup summer. And so we had a bunch of people in South Africa, and then we had a bunch of people in the office just reporting their own things. And I remember at the time, the Journal had a feature of the sports page every day called the Count, which was a short statistical piece every single day. Sometimes it was gathering data that was out there and saying, how many times do the Dallas Mavericks high-five each other during a game?

And sometimes it was like, what if we just took an idea and pushed it to the max and gathered all this data that was available and just presented it. And so one of them, in fact, it might have been the piece that I filed. And every editor swarmed my desk and said, “This is fine, it’s going to get rewritten, but don’t worry.” Was my editor, who is insane and brilliant, came over one day and he said, “What if the World Cup was a war? Who would win? How would we go about quantifying this? Military size and GDP and just come up with all these different metrics and let’s rank them and see where we are.” And presumably that meant the U.S. was not going to win.

We needed to come up with, actually the Netherlands would win if there was… or the the round of 16. And so that was, you know, before Claude could just go out and do this for you. It was like, well, how are we going to think about this and what data are we going to get. And how are we going to confirm that it’s accurate and it’s not just something that we pulled off of Wikipedia? And is there a way that we can present this that is not completely offensive, but is actually interesting and thought-provoking and kind of funny and people will get it? So that was one that stands out from that first summer of, oh, yeah, what if the World Cup were war?

Jimmy Soni: Can you talk a little more about Sam Walker and the effect that he’s had on your career and your life and the way you write and all of that?

Ben Cohen: Yeah. Sam Walker. There are a lot of people who came up through the Wall Street Journal sports section then, and I think they would all credit Sam for sort of being the evil genius voice in our head. And Sam is a brilliant writer himself. One of the reasons why it was okay that Sam was rewriting you was because he was just such a better writer than any of us were, that you would read it and be like, “Well, I would never say this…”

Jimmy Soni: But it’s said way better.

Ben Cohen: The fact that my name is on these words is actually great.

Jimmy Soni: Yeah.

Ben Cohen: And just a diabolical genius. He had just such smart and clever and inventive ideas and ways of reporting and writing and just making sentences sing. And his voice is constantly in my head. And so one of his rules for writing and especially finding stories was that the lead quote in any story that we wrote, which meant that the idea had to be so clever and so novel that the lead quote could have been, not that it should have been, but could have been, “I’ve never seen anything like this before.” And that was what we aspired to every single time. And so we were always looking for ideas that could be, “I’ve never seen anything like this before.” And the highest form of praise is when Sam would just write back in an email, “Yes,” with eight exclamation points and weird bolds and yellow highlights and that praise and affirmation is still, I should just print out those emails because they still mean so much to me.

Jimmy Soni: Yeah. So fast forward a little bit. But I’m curious how you got the book writing bug at some point and you did these, you know, we’ll talk about your book, The Hot Hand and what you’re working on now, but you did a couple of e-books, short books that you did on your own with a publisher. Tell me the story about those. Because, you know, they’re close to my heart. One’s obviously about Coach K. So there’s a Duke connection. But I’m curious what prompted those projects.

Ben Cohen: So there was, I lied a little bit. There’s a slight gap in which I was freelancing for the Wall Street Journal and I was editing and writing a lot of stories but was not on staff. And so I had the freedom to do a little bit of freelance experimentation. And in 2011 it must have been, Mike Krzyzewski was going to break the all-time college basketball wins record. And I thought, you know, I’ve probably thought more about Mike Krzyzewski than most people on this planet and I’ve had some privileged access to him and feel like I could get a little bit more. There had sort of been a change in his career that coincided with the time that I was at Duke and writing about him and thinking about him a lot.

And I thought maybe there might be something interesting here. What is it like when a 23, 24-year-old writer tries to write a long magazine-ish profile of Coach K that is not written by 40 and 50-year-olds who remember what he was like when he was hired at Duke, but who was on campus as he was evolving and turning into this version of Coach K that kind of the world knows and maybe doesn’t love but or loves to hate or but it’s just familiar with. And his career had evolved in a really interesting way.

And so I wrote this e-book which is kind of like sort of a long magazine piece about how he got to this point in his career, which allowed me to flex my muscles a little bit and go beyond my comfort zone. I don’t think I’ve read it in 15 years. I have no idea if it’s any good or not. And I would probably be mortified to read it today. But it was an interesting experiment both with the form of actually writing it and in the medium in which it was presented. It was not a newspaper piece, it was not a magazine piece. It was asking people to pay 99 cents for a piece of journalism, which is still kind of a novel concept, but was very strange and interesting back then.

Jimmy Soni: Did it do what you wanted it to do? Did you get feedback? Did you, I don’t know what metrics you might have had for success, but I’m curious, other than feeling like you did something, did you measure the success of it in any other way?

Ben Cohen: You know, I don’t really remember. I remember just thinking, “Oh, this thing exists. My name is on Amazon.com now.” And which hadn’t been before. And I accomplished this thing. And I had always known that I wanted to write books, too. And this seemed like an interesting stepping stone along the way. You know, at the time, writing for a newspaper meant writing stories that were between 800 and 1,200 words. And no matter how many calls you made or how much reporting you had, the stories were between 800 and 1,200 words every time. And so this was, okay. Well, I’ve been thinking about this guy for five, six years at this point. I can call a bunch of people. I have pretty good institutional knowledge about this guy.

What would it mean to write 8,000 to 12,000 words? And, you know, when you get to a book, it’s, what would it mean to write 80,000 words? And how to keep people’s attention. But it was an interesting experiment in that form, I think.

Jimmy Soni: You said that you’d always had designs on writing books. Was that just a natural extension of kind of being around writers and word people and being in newsrooms and stuff? Or were you, is this a big part of your life? Books in general?

Ben Cohen: I think when I was a kid, I just loved being in the bookstore, and I loved seeing what was on the bookshelf and imagining, who are these writers? And where do they get these ideas and how do they go about reporting? I mean, I’m a big journalism nerd. And I still am. I’m very curious about where people get their ideas from and how they actually go about structuring their day to write books. And so I just, and it just seemed like the natural next step. You’re a journalist. And you get to write books. That is, I said get to, not have to or, you know, whatever. But it seemed like a great privilege and something that would be really fun to do.

Jimmy Soni: Yeah, when I was growing up, there were books that really stayed with me. Series that I would just devour. And I look back and I’m like, a lot can be explained by those choices. I’ll give you an example just to riff on it. But there was the Choose Your Own Adventure series. And I think I would have, the right psychiatrist would have diagnosed me as sufficiently neurotic if they had seen that at every critical juncture in a Choose Your Own Adventure book. I would dog-ear the page so I could go back and make a different decision.

Ben Cohen: You choose a different adventure.

Jimmy Soni: Choose a different adventure. And so, but at every decision point I would be racked with, well, what if it doesn’t work out? And then I would dog-ear the page, come back and play out the alternative. I’m curious if there were series or series of books that when you were a kid really stayed with you.

Ben Cohen: I remember reading the Matt Christopher young adult sports books. I don’t remember, I definitely dog-eared the pages, but I don’t remember going back and choosing different endings for them. But I feel like that got me from a young age and Goosebumps. Obsessed with Goosebumps. And I think maybe it’s just because there were new books all the time. And the same way that you had to wait four years for a new Harry Potter book or whatever. But these, there was a series and you could just sort of keep banging through them. So I was a voracious reader when I was young. And I still am, not so much books. I just read the Internet all day long now.

And every newspaper and I start my day, I read the Journal and the Times on my phone. I just try to read as much as possible in part because that’s where I get my ideas now. There are reporters who are very good at calling their sources and calling 50 people a day and schmoozing and sweet-talking them and I’m surrounded by these people at the Wall Street Journal and they are on their phones and just chatting with people all day long. And I’m not good at that. And that’s not how I get ideas. I get ideas by reading everything I can and trying to find nuggets or ideas or stories that connect and haven’t been connected before.

And I feel like my competitive advantage in journalism is having a good eye for a story and seeing what is out there and being able to connect dots. But I remember the first, the book that probably made the most impact on me was Moneyball, which came out when I was in high school and I was obsessed with baseball and I love statistics and I love journalism and that book is just so brilliant in so many ways. It is, and this was before, I mean I was in ninth grade. I didn’t know that all of business was going to become Moneyball for this. But I just remember reading that story and thinking, “Oh, my God, someone wrote this.” How did this person find this story?

How is it written so compellingly and hilariously and insightfully? That story is just so brilliant from start to finish. And the fact that it was just sitting there under his nose for someone to write and to write it the way that he did, and then for that story to become the story of everything in America.

Jimmy Soni: A cultural touchstone in a kind of perverse way.

Ben Cohen: For sure. For sure. And it’s still, you’re still seeing the ripple effects of it now in every industry, including sports. It is still playing out in sports to this day. And it would completely revolutionize sports during the time when I started writing about sports myself. The statistical revolution and how players were valued is kind of what I spent 10 years writing about as a sports writer at the Journal. That idea of a bunch of numbers on a page changing the way that an entire league could value a player. And, you know, Michael Lewis has talked about this a lot, but one of the really just incredible things about that story is that, and the reason why it resonated the way that it did was that sports is probably the most quantified part of society.

We can watch all the games. We know exactly how much players are paid, we know why they’re paid that, we can put a number on every single thing that someone does on the court or on the field. And yet, despite all of that information and all of those statistical metrics, players were still being misvalued all the time. And we didn’t know what made them good or what made them bad. And if that could happen in that industry, then of course, that could happen in every industry. And so that idea of shifting value, and I wrote about it in basketball, guys who were the eighth or ninth guys on the bench, statistical metrics showing that they were insanely valuable and they would get contracts worth $200 million.

That’s just such a juicy and rich story every time, because you can tell a really human story through those numbers, which is what Moneyball did. The reason why people remember that is because they remember the characters and how they were brought to life and the numbers identified those people. But the story that it tells is an incredibly human story.

Jimmy Soni: Did you read that when it came out?

Ben Cohen: Yeah.

Jimmy Soni: You were in high school when you read that.

Ben Cohen: Yeah.

Jimmy Soni: Because that is not a book that I imagine every high schooler has in their backpack.

Ben Cohen: No, but I read it as a baseball book. And I remember because I was a Yankees fan growing up, and those, the Yankees beat those A’s teams, but I just remember. I don’t think I ever thought, I don’t know what their salary cap was or that they had the lowest payroll in baseball and they were still winning all these games. But when I read the book, I was like, who is Jason Giambi and Johnny Damon? And how are all these guys from this part of the country that I’ve never been hanging with the Big Bad Evil Empire every year, you know? And so I came away from that book not only thinking, “Oh, this changes the way I think about baseball and statistics,” but journalism. This is a story that can be told.

Jimmy Soni: Oh, that’s. There’s a great moment, I think. Michael Lewis didn’t interview. He’s done a bunch of interviews about that book, but I remember seeing one where he’s actually a little nervous to release the book, I guess. He goes to Billy Beane, and it’s like, “I’m, you know, I’m kind of giving away state secrets here” This is a methodology you have refined.”

Ben Cohen: And Billy Beane says, “You don’t think anyone’s going to read this book.”

Jimmy Soni: And part of the reason was, you don’t think anybody in baseball reads books, do you? So you had The Art of Winning, which was the Coach K book, but you had this other one that I was, An Illustrated History of Duke Basketball. Is that even, tell me the origin story of that one? How did you...

Ben Cohen: I think I wrote the epilogue to that.

Jimmy Soni: Okay.

Ben Cohen: That book existed, and I think it was 100 Years of Duke Basketball. It was written by this guy, Bill Brill, who was this legendary sports journalist in the Research Triangle in North Carolina. And the book had been written, and Duke’s basketball team was turning 100 years old, and they needed someone to write a chapter about the last few years. And those last few years were the years that I was on campus. And it ended with Duke winning a national championship in 2010. And so I think I knew Bill a little bit from when I was in school, and he very kindly and generously said, “Would you like to write this final chapter, since you lived through it?” I was like, “Oh, my God. Amazing. Yes.”

Jimmy Soni: That’s awesome.

Ben Cohen: I have a lot of thoughts about Duke basketball between 2006 and 2010. Thank you for asking.

Jimmy Soni: That’s amazing. How did you start working on The Hot Hand? And we’re going to, we’ll get to your column now, the Science of Success. But I’m curious about, you know, you’ve been doing it. You’ve been writing for the Journal how many years before you started this and kind of what was some of the stuff that was in the stew while you were working on this?

Ben Cohen: So I think I sold this book in 2017. So I’d been at the Journal for about seven years then, writing for the Journal for seven years, on staff for five years. And this book was born out of two stories that I wrote for the Journal at the time, I was vaguely familiar with the idea of the hot hand and this idea that in basketball, if you make a few shots in a row, you feel more likely to make your next shot. And I think I may have been aware of this fierce generational academic debate about whether or not the hot hand exists. I first became aware of the concept because I felt it myself as a terrible basketball player in high school.

The one time when I made three shots in a row, I still had this vivid memory of that afternoon. I could tell you where it was. It was at a Catholic school in New Jersey that no longer exists. It is defunct. And I just remember everything about that day. I have no idea why it happened. It never happened to me again. But I felt something that day that just stayed with me forever, and I had no idea. There was this long debate about whether or not that feeling exists that has looped in some of the smartest people who ever lived and applies to so many industries.

So I remember the first time I came across this concept in academic literature, because one of the things about writing for the Journal is that when you’re looking for stories that nobody else has written, you go looking in a bunch of funny places for them. And I remember seeing a couple papers about the hot hand, and I started reading them, and there was this new paper that came out that was presented at the Sloan Sports Analytics Conference, which is kind of like, it’s called Dork-a-palooza. It is the industry convention for sports analytics. It was really born out of Moneyball. So in some ways, this book was born out of Moneyball in a very strange, roundabout way. This paper was presented at the Sloan Sports Analytics Conference at MIT, had been written by a couple of Harvard undergrads.

And it used all of this data that had not existed until then, with data that came from shot-tracking cameras in every NBA arena that was able to collect attributes about shots that had never been tracked before. And these undergrads had this really clever and counterintuitive idea to take that data and say, “Well, the hot hand is this idea that has been studied by Nobel Prize winners and economists and psychologists for decades. What if we actually apply this data and search for whether there is a hot hand effect?” And they found that when you adjust for the quality of a shot and the difficulty of that shot, then there is actually something of a hot hand effect.

And the reason why the hot hand had been such a contentious topic in the academic literature for so long was because there was this seminal paper that came out in 1985, written by Amos Tversky of Kahneman and Tversky fame, that said, “Actually, the hot hand doesn’t exist. It’s just a figment of your imagination. It is this canonical example of seeing patterns in randomness.” And that bias, the hot hand bias, reflects so many other forces in society, and that is why it’s so interesting. And what these Harvard undergrads were coming along saying, that was a really, the broad takeaway of that paper was accurate, but this specific takeaway actually may not have been accurate. And you might not be crazy to think that there is such a thing as a hot hand.

So I wrote a story about that paper for the Wall Street Journal. There’s this big response to it. And then the next year, there was another paper that came out about the hot hand that was interesting in an entirely different way. I wrote a story about that paper, too.

I thought, you know, these really smart people have been thinking about this idea for a really long time, and I wonder if there is a way to take this idea and tell a whole bunch of stories through it and use this idea to explore the world of basketball and beyond basketball and take it to markets and decision-making and use the quest to figure out and solve the mystery of the hot hand as the narrative spine for this book and then go in all sorts of interesting and unexpected directions and just kind of surprise and delight the reader. So that is the challenge that I assigned myself while writing this book and thinking that I was possibly capable of pulling it off.

Jimmy Soni: What a description. And I will say this is, it’s actually made me think this morning because I was reflecting on your body of work, and I thought to myself, the thing you bring is delight. And part of delight is surprise. Why is Christmas morning interesting? Part of the reason Christmas morning is interesting is because you don’t know. If you’re a kid, you don’t know what you’re gonna get. Things are wrapped up. That’s what I love about your work, is that I actually never know what I’m gonna get with, particularly with your Science of Success on a given day.

Ben Cohen: I don’t either.

Jimmy Soni: Yeah, right. You’re like, I’m making it up as I go. But the book covers art. It covers investing. You have a thing on sugar beets in there.

Ben Cohen: I take a trip to a sugar beet farm in North Dakota. Yeah, yeah.

Jimmy Soni: Tell the story of that. That’s an interesting part of this whole...

Ben Cohen: Part of the story of the book is, should you believe in the hot hand? And more important, should you behave as if you believe in the hot hand? So if you are on a basketball team, the simple version of this question is, if someone has made a couple shots in a row, is it smart to feed the hot hand and get that person the ball? Or is that person going to miss and you’re going to think that your brain has played a trick on you? But that question is so much more interesting and important in parts of the world that are beyond a 94 by 50 piece of hardwood. So in markets, should you give your money to an investor who has beat the market a couple of years in a row? Does that make him more likely to do it? There’s a story in the book about Rob Reiner and his directing career.

And when you’re hot as a director or an actor, the world kind of opens up to you a little bit. You are able to take bigger swings and take advantage of your hotness and do stuff that you wouldn’t be able to do otherwise. So Rob Reiner starts his career by making This Is Spinal Tap and then Stand by Me and The Sure Thing. And he’s made three hit movies in a row, all movies that nobody else wanted him to make, oddly, which you wouldn’t think of today. You would think, “Oh, someone should have been throwing money at him to make This Is Spinal Tap.” And after he makes these three movies, he is hot in Hollywood. He is a director who can kind of get anything made that he wants to get made.

And he has this conversation with a studio executive around that time. She comes to him and says, “You’re Rob Reiner. You’re making these movies that everybody loves. What do you want to do next? We’ll do whatever you want.” And he says, “You’re not going to want to make the movie that I want to make.” And she says, “No, trust me, we’ll do whatever you want. What do you want to make?” And he says, “No, trust me. You’re not going to want to make the movie.” And she said, “Just name the movie.” And he said, “The movie I want to make is The Princess Bride.” And she says, “Well, anything but The Princess Bride.” And I was shocked to find out that The Princess Bride was this movie that the biggest names in Hollywood had tried to make for years.

Robert Redford and Norman Jewison, François Truffaut, they had all tried to make The Princess Bride. And it had been this riddle haunted by a curse that was wrapped in an enigma. Nobody could figure it out. Nobody could think out, who was this movie for? And why would anyone want to see it? Makes no sense today. It was written by William Goldman, coming off of Butch Cassidy and the Sundance Kid and All the President’s Men. It’s just a beloved movie that has just endured for generations. But Rob Reiner used all of his capital as a director, and I remember we traded emails and he said, “I don’t know what you’re talking about. That movie was still impossible for me to get made, even with this hot hand.”

So anyway, the reason we go from Rob Reiner to a sugar beet farm on the border of North Dakota and Minnesota is because if you’re a farmer, do you bet the farm on patterns? How are you thinking about patterns and randomness and data from year to year? And so I met this really fascinating fifth-generation sugar beet farmer named Nick Hagen, who has to think about all of these lessons that his ancestors have taught him over centuries about how to think about data. And if one patch of his farmland has yielded a whole bunch of sugar beets the year before, does that mean he should invest more in that patch of land going forward or not? And what does it mean to be in an industry that is as random as the weather?

And can you believe in the hot hand? And if you do believe in the hot hand, even in life, can you invest in the hot hand in your business? And so there are all sorts of interesting ways of looking at the world where I might feel that the hot hand is real in basketball. Yeah. But I might still also invest in index funds because I don’t believe that someone’s going to beat the market year after year.

Jimmy Soni: Right. If you go back to the kind of pre-selling the book process, you know, you’re somebody that’s worked at the Journal but you’re still pretty young in your career. What was it like to think about the book? How did you do the mechanics of what came after the decision, like, “Hey, this should be a book-length thing.”

Ben Cohen: I remember we sold the book and I was so happy and went through the whole process of sending out the proposal and getting an offer and signing it and I woke up the next day and thought, “Oh God, what am I going to do now? How do I, I don’t know how to write a book,” and especially a book as open-ended as this one. And it’s a challenge that I actually sort of deal with on a week-to-week basis now because when you can write about anything, the bar has to be super high and you have to think, “Oh well, what I write about has to be something worth writing about.” It can’t just be like, “Oh, I happen to find this story interesting. I’m going to spend 10,000 words and three months of my life and get you to read it.” It has to be important and interesting and keep my attention, much less the reader’s attention. Then I just sort of went looking for stories and casting about for characters and they had to be stories and characters who, when I told my friends about them, I could see their faces light up. And I was eager to tell people about them because I wanted to sort of stress test and pressure test the arguments and the characters and the stories. You’ve written books, you know, when someone asks you what are you working on? You’re like, “I don’t want to talk about it.” And I still don’t want to talk about it.

But all the times that I did talk about it, I could get excited talking about it. I will say I wrote this book before I had kids and I wrote the book on mornings and weekends, which are things that now that I do have kids I no longer have. I remember waking up early in the morning, was waking up at 7:30 and banging out a thousand words before work. So it is, in some ways I was insanely green and eager and ambitious and didn’t know what I didn’t know, and was very happy and sort of inexperienced, but also had a lot of time and no responsibilities, which is a great thing.

And it’s just much harder to write a book with a full-time job and kids and life responsibilities.

Jimmy Soni: How did you go about? You have a very particular thing you do at the Journal and the pace is a certain kind of pace. Did you just stick to a word count every day to get the book done? Was that how you basically approached it?

Ben Cohen: I tried to, yeah. I feel like the advice out there to write between 500, 1,000 words a day and just get them on the page is very good advice. And it works for a reason because you don’t think you’re doing all that much. And all that work compounds over time. And after a few months you have 85,000 words and then you can start chiseling and shaping it and getting it into a place where you want. I’m, even now I’m in the process of writing a book and so I’m thinking about it and the hardest part is just getting the words on the page.

The reporting is done, I have all the material and it’s just vomiting the words onto the page and getting it into a place where I can print it out and start redlining and thinking about what comes next. But for me, that routine of just writing a thousand words and then going to work was very helpful.

Jimmy Soni: Right. Did you…

Ben Cohen: What about you, how do you think about it?

Jimmy Soni: Yeah, it’s the same thing. I mean it’s, and it’s funny because it’s a bit of a rinse and repeat process. There’s not, once I have the subject, once I have the actual thing I’m writing about, and I’ve done all the research and I’ve done all the interviewing and everything else. I mean, you just set a manageable word count number every day. I tell people it’s kind of like enough that it’s substantive but not so much that I’m going to be burned out of my own project. And I just have a little, on Scrivener, they give you this little indicator. Scrivener’s the software I choose to use when I’m doing the raw material for the book.

And it’s really funny, there’s a little indicator and it gets green when you hit to that point in your, when you hit the words. And I just try to get it to green every day and just keep going. And then, as you said, over time, you collect everything. I think the real work is in then the revising, the shaping, the trimming. But honestly, I just, I woke, I woke up, same as you. You just wake up obscenely early. You knock out the words you need to knock out, and you get back at it the next day. And then some days you kind of double or triple. And those are great days. You’re like, “Oh, I’m ahead,” but I still go back every day and just keep going.

Ben Cohen: I also found the most productive writing time for me was early in the morning. Or what I considered early in the morning back then, without checking my phone. I would check my phone to make sure the world was still spinning and nothing terrible had happened overnight. But I hadn’t checked email. I didn’t look at Twitter. I didn’t do any of the stuff that I would normally do that turns my brain into mush. And I could get more done in that first hour than I would over 12 hours over the course of the day. It was just getting the stuff out on the page was so valuable and helpful and useful to me. And now I have two young kids. That means waking up at ungodly...

Jimmy Soni: Yes. But you do get used to it. And then the other thing is, I always felt like if I did the book work, even because I’ve done now two of my books after my daughter was born, and actually three of them, and I find that if I can get something done before she’s awake, then I’m not robbing Peter to pay Paul. I don’t feel that way. I’m like, “Okay, I’ve gotten that stuff done now. Now time with her is not a tax on book time.” Right. And so for me, that’s worked really well. I would also say that the part about it that people don’t appreciate is it sounds fun and it looks fun, but as you said, it’s a real struggle to go from interviews and raw material to finished words on the page. There is still something in that that is really hard, especially if you’re doing it twice. You’re doing it once in the morning and then going to the Wall Street Journal, doing it all day. How did you manage that? Or was it just different kinds of writing? So it was okay.

Ben Cohen: I think it is different kinds of writing. So I think there is some element of cross-training to it where I think both made me better at the other one. The book writing allows me to push my limits a little bit more and stretch muscles that I don’t get when I’m writing a weekly column. And it allows you to think and make connections and just let stuff sort of marinate in your brain that you don’t get in an 800-word column when you’re on a specific cadence. And even now, I’m in the process of putting a bunch of chapters together and I’m seeing patterns and connections between the chapters that I didn’t think of when I was writing them. And clearly, they were always there and they just were waiting to be mined.

And the only way I was going to do that was with time and some distance from the material and being able to come back to it with fresher eyes. And I also find the reporting of these chapters is so fun. And you come back from a reporting trip, you’re so eager and, for this book, I’ve made the mistake of not just writing right away. And then months pass and I have to relive the interviews and go back and listen to the tape and I’m like, “What was that about again? What were those images that were floating around my head?”

And so I wish that I had just come back from a bunch of reporting trips and just written 10,000 words as soon as I got back that I would be in a much better shape now today if I had done that.

Jimmy Soni: When you think back on this particular book, the moment that, you know, it can always be an interest is either when, for me, when you get the first finished copies of the book, that box shows up. They don’t warn you. They don’t. Nobody tells you they’re on. Sometimes they’ll tell you they’re on their way. But most of the time a box just shows up and you’ve got the finished copies. And then when you start to see it out in the wild, what were those moments like for you with this particular project?

Ben Cohen: My book came out March 10, 2020.

Jimmy Soni: Oh, perfect timing.

Ben Cohen: Great timing. Yes. So the book party was on a Tuesday and the world shut down on Wednesday. And so I have very strange memories. I walked into Three Lives bookstore in the West Village, probably the day before it closed for a very long time. And I saw the book in the new nonfiction part. And I got that joy and then didn’t see other people for a very long time afterwards. So it was a peculiar experience of releasing a book into the teeth of the pandemic. Yeah.

It just means what people warned me from the beginning, even before it was clear that it was going to be a very strange time to release a book, is that books have a long tail in a way that newspaper articles do not, and that people would be reading this book and coming to it in different ways for a very long time. And I found that totally to be true because you get an email from someone who picked up the book five years later, and I wake up in the morning and I see an email about that, and I’m like, “Well, I haven’t thought about this book in seven years, but it’s living in your brain right now.” It has lived on in this really rewarding, gratifying way.

So that is something that is totally different than writing a newspaper column that appears in print and then you will get 99% of the traffic and attention the day it comes out. And then never again.

Jimmy Soni: Yeah. I’m going to ask a couple more book questions, and I want to shift to the Science of Success and your current project. When, how did you settle on the title and the cover art and that kind of stuff? I mean, I imagine some of it was intuition, but did you sell it as The Hot Hand?

Ben Cohen: We did. That was the title the whole time. Yeah. I felt that was intuitive and sticky and a little bit seductive. That if you knew what the hot hand was, you would be curious why it was the title of a book. And if you didn’t know what it was, you would also kind of want to know a little bit more about why it was the title of the book. And I liked the rhythm of it. And I actually hate alliteration in writing. If I write a piece, you will almost never see two words with the same first letter back to back, because it’s just an eyesore to me. But there was no other way of. Yeah. And I think it was a neat way of doing it.

And I didn’t have control of the cover but I do remember we were talking about potential art for the cover. And I think I did suggest, what about a fireball emoji as the O in The Hot Hand? And they sort of ran with that from there.

Jimmy Soni: That’s great. How did you transition from the work you were doing as a sports reporter at the Wall Street Journal to what I think is one of the great sections of any contemporary newspaper. It’s a thing, again, that I look forward to reading so much. How did you start and build and grow the Science of Success?

Ben Cohen: So in 2022, I had been at the Journal for 12 years. I’d been covering the NBA for almost 10 years. And it was an incredible decade to be covering basketball specifically. So the first, really, the first major season that I was covering basketball was 2014, 2015, which was the first year that Steph Curry and the Golden State Warriors won a title by playing basketball in a completely new and interesting and exciting way and really revolutionizing the sport. And that idea of the three-point revolution taking over basketball was such a Wall Street Journal way of covering basketball. This idea that there is a shot on the court that is worth 50% more than a shot that is one inch closer to the basket. And it’s this incredible market inefficiency hiding in plain sight.

And it had taken teams decades to figure out that three was worth more than two. And now you have this team with the most charismatic and compelling player of his generation, who had been overlooked his entire life, taking advantage of it to incredible effect. I mean, that team in 2016 was a cultural phenomenon, the most exciting team since Michael Jordan’s Bulls, with this really iconic player taking on LeBron James, this behemoth who had conquered the sport in a completely different way. And this rivalry was taking shape, this incredibly unlikely rivalry. Nobody saw this coming. And so my first four years covering basketball, the NBA Finals every year was the Golden State Warriors versus the Cleveland Cavaliers. So I spent a lot of time in Oakland and Cleveland and felt like it was Groundhog Day.

I was like, “Yeah, it’s June. I’m going back and forth between Oakland and Cleveland.” There are all sorts of fascinating stories about ways that teams were trying to build themselves to take on the Warriors. So the Houston Rockets was a team that I wrote about ad nauseam. So I probably wrote the most about Steph and LeBron and James Harden and Daryl Morey and Mike D’Antoni and the Houston Rockets, because they were trying to dethrone the Golden State Warriors by building a team and pursuing this counterintuitive strategy to beat them. And they would talk to me about it and I would get to explain, here is why this team thinks that they can beat the unbeatable Golden State Warriors. And they came really close, and it was just really fun. Teams were taking control of data and statistics.

And you could just see all of these stories unfolding that we would have never been able to write about at any other point in basketball history. And so, but over time, I sort of felt that I had just written the same story over and over again. I think one of the great strengths of a journalist, and it’s really important to have fresh eyes and to not be jaded and to be surprised and delighted by stories when you find them and not think, “Oh, I wrote that story six years ago,” or a different version of the same story. And so I’d been looking, especially after writing The Hot Hand, I’d been looking to expand a little bit beyond basketball.

And when I was pitching this column that became the Science of Success, the whole idea was, can I take this playbook that I’ve been able to come up with and learn from writing sports at the Wall Street Journal and take that idea and apply it to the rest of the world and all sorts of industries and the rest of business? Can I find interesting people doing interesting things in important industries and other important industries and just try to write about them the way that we write about sports at the Wall Street Journal? And so also in the same way that I have found that writing a book is different with children. And covering basketball means working a lot of nights and weekends, and nights and weekends are what you kind of don’t have when you have young children.

And so I thought this was the right time to kind of look around and take the stuff that I’ve learned covering sports and basketball at the Wall Street Journal and explore the rest of the world with it.

Jimmy Soni: How do you, I mean, I have a million questions, but how did you sell it internally? I mean, to the extent you’re allowed to talk about it. It seems like a very specific thing. I’m going to cover everything, success and failure in all human endeavors.

Ben Cohen: It happened to be at a time when the Exchange section of the Wall Street Journal was looking for a couple new columns. And I had said, I’ve done this for a long time, and this is what I want to do. And I wrote a memo explaining the type of work that I wanted to do, the lens through which I saw the world and wanted to explore the business world, and came up with a bunch of sample ideas and stuff. I will, we want to be on the news. We want to be timely. We want to be a little bit timeless. We’ll see what happens every week. And can we write about people the way that we write about athletes? And maybe I was just very lucky again, that people inside the paper sort of trusted the vision that we had and said, “Let’s try it and see what happens.”

Jimmy Soni: Yeah, I have to believe that there’s some part of you and maybe you’ve just gotten so good at it. How do you wrestle with the challenge of meeting that bar every week? Because it is, it’s one of the, your consistency in your quality of subjects and topics and approaches. Do you just have a folder? Is there a big Ben Manila folder somewhere? Like, “All right, time to dust this one off.”

Ben Cohen: Yeah. It’s a Google Doc. It’s called Just Ideas. I do have, when I come across interesting people or companies or ideas, I will dump them into a Google Doc with just very basic information. Maybe copy-paste paragraphs of stories that were interesting and think, is whenever the time is right for this, or maybe something else will happen and there will be a time to pick up on this. But a lot of times it’s also just following the news very carefully and thinking, “Okay, well, there’s this one interesting nugget in this story that wasn’t fully explored, and I’m really curious about that.” And having the freedom and the luxury of following my curiosity to wherever it may lead.

Doing the full reporting, going deep into a subject, reading everything that’s been written about it, listening to every podcast that this person has been on, and trying to tell the story through that very small thing. And so that’s something else that I learned covering sports at the Journal is that I think there are two ways to tell stories. One is taking small ideas and making them really big, and one is taking big ideas and making them really small. In some ways, they’re connected. But, for example, we always used to look for funny, interesting, peculiar, clever ideas at the Wall Street Journal. So one story that I wrote was, in 2016, the Golden State Warriors started the year 24-0. They were 41-4 at one point. There was nothing that was going wrong.

And as a journalist, you’re always looking for tension. Tension is what makes a story. And when there’s no tension, it’s like, well, what do you do with that? And I remember listening to a bunch of radio interviews the Warriors were doing at the time. You know, probably the only person outside the Bay Area who was actually listening to interviews on local radio. And in one of them, the interim coach at the time, Steve Kerr was on medical leave. And the interim coach at the time was Luke Walton. And he was doing this interview as he was walking off a plane, and they were saying, “Luke, what’s going on? How are you doing?” He was like, “I’m terrible. The team trainer before the season got rid of our peanut butter and jellies on the team plane because he thought they weren’t healthy. And everyone is completely miserable about it because all NBA players famously eat, they just subsist on peanut butter and jelly. It’s just around at all hours.”

And I heard this, and I was like, “Okay, well, the story to do is that the greatest source of tension in the locker room in Golden State right now is they’re fighting to get their peanut butter and jellies back.” And so that’s a funny idea for a story. And then you take it to the extreme. And they happened to be coming through the East Coast a couple of days later. I remember I went to Philadelphia and stalked their locker room and went quietly to every player in the locker room and asked, “What do you make of the war over peanut butter and jelly in the locker room?” having sotto voce conversations with Steph Curry in the side of the room. Then the next day, they were in New York, and I went to the Garden, did the same thing. And over time, you’re reporting, that’s hours and hours of reporting to ask players off to the side to get an exclusive about peanut butter and jelly. And so you could tell sort of the story of the Golden State Warriors’ magical season through the only thing that has gone wrong for this team is peanut butter and jelly.

And so I’m always kind of looking for peanut butter and jelly stories in all sorts of industries. And one other thing I’ve learned through the course of writing this column is that if I find something interesting, the chances are that I can convey that interest and enthusiasm to readers. And if I don’t know something that it feels like everybody else knows or should know, then the chances are that they don’t know it either. And, you know, I find myself thinking a lot, “Well, does everyone know this? Or am I just an idiot and just found out for the first time?” And I think a lot of people don’t know a lot of things. And so things that you would think that everybody knows, they don’t know, and I didn’t know them.

And so I’ve learned to kind of trust my judgment and gut about that a little bit. If I think something is interesting, I can convey that interest and I can make other people interested in it as well.

Jimmy Soni: Yeah. Do you have, I mean, it’s probably like picking a favorite child or something. But let’s say from the last couple of years. Is there a story that stands out to you as a favorite of yours?

Ben Cohen: One of my favorite stories I ever did was two years ago I went to Boise, Idaho to visit the campus of Micron because Micron Technologies. Micron Technologies, yeah. In one of their chip factories in Boise, Idaho was a machine made by a company called ASML. And ASML is the most important, valuable, invaluable company that most people have ever heard of. And in the world of chips and semiconductors, which is the most important industry in the world, there are a bunch of really interesting companies. There’s Nvidia, which, you know, nobody outside of gamers had heard about five years ago. And then it became a trillion-dollar company. And I remember writing a column about it when it became a trillion-dollar company that was basically like, “What is the story of this company?

It looks like someone fell asleep on their keyboard typing it out. I’ve never heard it. This company is worth more than Berkshire Hathaway. Now, how did this happen?” There’s TSMC, Taiwan Semiconductor Manufacturing Company, which is the most valuable, geographically important company that makes all the chips. But in every TSMC fab, and in every Micron and Samsung chip factory, there is an extreme ultraviolet lithography machine. An EUV machine is made by ASML. This is the most important machine on the planet. It is the bottleneck in the chip-making process. And only one company in the world makes these machines. This obscure Dutch company called ASML, which is one of the 20 most valuable companies in the world. And if you say ASML, most people will think you said ASMR.

And I remember thinking, “Okay, I found out about ASML. And I said, I can’t just write a story about ASML because while most people have never heard of it, even people reading the Wall Street Journal have never heard of it. I can’t just be, ‘You guys hear about this company, it’s this amazing company.’” But I remember I was reporting around ASML and someone told me that there was a job in ASML called customer support engineer. When I hear customer support, I think someone in a call center dealing with problems. Customer support engineer is a person whose job it is to make sure that machine never breaks and when it does break that they can fix it right away.

And I thought, “Okay, well this is the most important job at the most important company that nobody’s ever heard of and I can put a human face to it.” And so I talked to the company, we cast about for a few characters. We eventually settled on this woman named Brianna Hall who worked at the Micron chip fab as an ASML employee, as a customer support engineer. And I was able to tell the whole story of ASML and its importance to the global economy and everything we do all day long through this one person.

And I thought, “Oh, this is what I’m trying to do is to take this really big story about the global economy and the most invaluable company that most people have never heard of and boil it down to this one person doing this one crucial job on this one machine that is responsible for all of our lives.”

Jimmy Soni: A series of your pieces from that are becoming a book or you’re working on kind of structuring a book. How have you been thinking about this current, we’re in media res on that project so there’s only probably so much you can share. But this is your next book coming up. How are you approaching it? How are you thinking about it?

Ben Cohen: The book was really born from the column and one of the, there was a type of column that I kept running into that I really liked writing and I found that readers really liked reading. I kept talking to people who had come up with interesting startups or products or just things that I had encountered in my day-to-day life, which I find is how I find a lot of stories these days. Stuff that is just in the air or I keep running into and I think, “Oh, what’s the story here? Why am I just noticing that everybody is drinking Athletic non-alcoholic beer now? How did this happen?” And the more and more I talked to these people and they all had a lot in common. They were unlikely entrepreneurs.

They did not set out to disrupt an industry or create something new. They just thought to themselves there has to be a better way. This thing exists and I’m going to make a better version of it. And I thought, “Oh well that’s really interesting. It’s sort of this new theory of innovation. It’s not invention. It’s taking something that already exists and making it better.” And I think there are lots of different ways that companies and people do that. You could do that by recognizing unmet demand or finding a new source of supply, or redesigning a product, or failing over and over or coming up with different mechanisms of finding ideas. So the book is, it’s a bunch of chapters about people and companies over time that have figured out new and interesting and hopefully universal ways of seeking and achieving better. And so a bunch of them will be expanded versions of columns that I’ve written, and a bunch of them will be stuff that hasn’t appeared in a column yet. So I wrote a column about Athletic non-alcoholic beer during Dry January two years ago. And so that’s an example of a guy working at a hedge fund in Connecticut sort of understanding that there was a demand for a non-alcoholic beer that didn’t taste like swamp water and thinking, “Well, maybe, I had this data,” he ran all these polls and surveys that he commissioned himself that found that 55% of Americans said that they would drink non-alcoholic beer.

And at the time, non-alcoholic beer accounted for 0.3% of the market. And he thought, “Well, there’s an inefficiency here. If I can get that 0.3% to even 1%, that’s a huge business.” And of course, it’s much bigger than 1% now. But that was recognizing the demand for a better product in data. That wasn’t like, “Oh, I think they’re,” you know, he recognized it in his own life and that he went out and found this demand and he created a product to meet that demand. Another column that I wrote for the Journal that will be in the book that I found in my own life is as the father of young children, my children go through just an enormous amount of berries every week. I spend all of my money on berries.

And a couple years ago, I noticed that there was this new type of berry from Driscoll’s, which, there are different types of labels on every Driscoll’s clamshell. There’s the yellow label, which is regular. There’s the green label, which is organic. And then there were two words that were appearing on some of these blueberries and raspberries called Sweetest Batch. And I remember tasting them and thinking, “What are these berries?” Because I can’t stop eating them. And they taste so much better than the other berries. I remember reaching out to Driscoll’s and saying, “What is the story of these berries? How did they happen?”

It turns out Driscoll’s, for years and years, for as long as the company has existed, have been throwing out its best berries because its most flavorful, best-tasting berries were not reliable and resilient enough to make it through the manufacturing process. So in berry manufacturing, this is, I didn’t know anything about berries before writing this column, and this is kind of what I do on a weekly basis. Go really deep into a rabbit hole and then come back out and try to describe it. In berry-making, all of berry production is a genetic trade-off. So if something is really flavorful, that means the yield might be lower. Or the bush might be less bushy or more bushy and so you can’t actually pick them or more brittle. So they won’t make their way across the country.

And because of that, they couldn’t make enough of these berries to make the economics work. And finally a few years ago, they said, “Well, why don’t we just keep these berries in the genetic pool for longer and then charge a slight premium for them and see if people are willing to buy them and we can make the economics work like that.” And they started doing that. They were just this massive hit because you taste one next to the other, it’s just a different experience. And now because Driscoll’s is keeping those better-tasting berries in the genetic pool for longer, the flavor of their ordinary berries is getting better because it’s moving the scatter chart up into the right.

And so there’s this curious economic effect just by someone saying, “Why are we throwing out our best-tasting berries? We should try to keep these in for longer.” So there are all sorts of stories like that. So it’s going to be Athletic and Driscoll’s and the story of Birkenstock and Dyson and Waymo and Ferrari and Hermès. And so all of these companies and products that I think people are fascinated by and that kernel of better is embedded in all of them in all sorts of different ways.

Jimmy Soni: Well, we will look forward to that and have you back on to talk all about it once it’s and when you’re done writing it. Sometime in the hopefully not so distant future, every Infinite Loops episode somewhat ends the same way. We declare you emperor for a day and you have a magical microphone. You’re allowed to incept two ideas into human minds. They won’t know that it came from you, but everybody will adhere to and follow your precepts. So what are your off-the-cuff, what are your two ideas that you would, based on everything you’ve done, based on all the successes you’ve studied, based on the book, based on looking at athletes and entrepreneurs and CEOs and other visionaries, what would you want people to have as their two ideas?

Ben Cohen: I couldn’t get any heads-up about this?

Jimmy Soni: That’s the whole point.

Ben Cohen: When I sent the email. Is there anything I should be thinking about?

Jimmy Soni: That’s the whole point.

Ben Cohen: I think that idea that has been floating around my head and rattling around my brain for a while now is this idea that better is always out there for people who can find it. And I think that there are all sorts of ways of achieving better. And a lot of it just comes down to feeling. A lot of it just comes down to being willing to play around with that idea of better is out there and that I can do this better and nothing is stopping me from doing it. So I think nurturing that sentiment and that mentality I think is really important. And in some ways, I don’t think about it like this, but I have to kind of do that every week when I’m writing a column. I think about it in two ways.

One is it can be finding new angles into stories and topics that the Wall Street Journal is already writing about, which is really intimidating because I think, “Well, we’re already writing about this. The people who are writing about this know this topic better than anyone in this building and quite possibly better than anyone in the world.” If they haven’t thought of this idea, why not? Is that because they did think about it and they dismissed it? Is it because they didn’t have time to think about it? Is it because they just happened to not run into it? There are all sorts of reasons why a piece might not exist. And I have to have the confidence every time to think, “I saw this idea. I think it’s interesting. Should I write it?

Is it just I’m a rube and I’m naive and that’s why I think it’s interesting? Or is it interesting because it’s interesting?” And the second type of story that I write is charging towards open space and cracks in our coverage. So industries and people and topics and companies that we don’t write about as a newsroom and sort of having the courage of my own conviction and following my curiosity and thinking, “Well, if I think Driscoll’s berries are interesting, then I bet a lot of other people will think Driscoll’s berries are interesting too.” And Driscoll’s might not be, you know, Nvidia or Apple or Microsoft, but the Wall Street Journal should still be writing about it. And Athletic might not be Anheuser-Busch, but I bet there is a market for people who want to read these stories.

And so I have had to think every time I’m staring at the blank document and the blinking cursor, I have to convince myself, if you think this is interesting, somebody else will too. And in some ways that’s, “Oh, there’s a better way of covering this story. And this is the way.” And that doesn’t mean that our other coverage is bad. It’s amazing. And whenever I, because I’m always giving a heads-up to the beat reporter. “Hey, I’m writing about this. If you have anything...”

Jimmy Soni: Here comes Ben to steal my thunder.

Ben Cohen: It’s a nice way of putting it. And I think, “If you’re working on anything, let me know. Maybe we could do it together.” But, and if there’s any reason why this is wrong or I shouldn’t be doing this, please let me know and save me from looking like an idiot and wasting all this time. And every time I do that, my colleagues and our reporters at the Wall Street Journal are such fonts of knowledge. They just know everything there is. And every time I work with them, I’m like, “Oh, my God, I can’t believe you know all this stuff.” And I’m just sort of pulling stuff out of their brains.

And I love writing, collaborating with people who are on certain beats at the Journal because I can just tap into their brain and I can look smarter. So I did a piece a couple weeks ago with our airlines reporter about the new strategy of United Airlines and why it is that I seem to see a tweet every other day, “United is the best airline in America right now” after years and years of Delta holding the title. And she interviewed Scott Kirby, the CEO of United. And we just sort of went back and forth all week long about what happened here. And it would have taken me hours and hours of research to figure out all of the crucial points in that story.

And I could just call Alison Sider, who was the reporter, and she had written all the story. She knew all of it already, and she knew so much more in her brain that I would have never been able to get out of any archival coverage or podcast. And so being able to take those ideas and team up with people and take one plus one and make it equal three is so much fun for me. I love writing with other people at the Journal for that reason. So I’m always looking for better ways to do something. And I think if I were emperor of the world and could take this microphone and turn it into a magic wand, it would be to kind of nurture that idea in other people.

Jimmy Soni: It was brilliantly said. And I feel like that hits both, you know, because there’s better, and then there’s also, you talked about the cracks, looking at the cracks, and I feel like that’s another useful lesson from your work, finding these places that people forgot, time forgot. Just the watchful eyes of an entire newsroom might have forgotten.

Ben Cohen: Right.

Jimmy Soni: And that’s why I love your work, and that’s why hopefully many others will love the book to come. And I can’t recommend The Hot Hand strongly enough, but thank you, Ben, for taking time to do this and for coming out and talking with us.

Ben Cohen: Thank you for having me. Thanks for such nice words.

Leave a comment

Subscribe now

Share

We’ve shared some highlights below, together with links & a full transcript. If you like what you hear/read, please leave a comment or drop us a review on your provider of choice.

Links

Apple Podcasts

Highlights

440 Million Mr Beasts

Revan Lazarus: I think in 20 years it looks super interesting in the fact that I think things are going to have to be a lot more personalized. I think that we might start seeing versions of creators or podcasters that are hyper-specific to the individual. One thing I’ve been saying for a long time is, MrBeast has 440 million subscribers, and I think there will be 440 million different MrBeast versions for each person based on the data. And so I think this has to be a platform overhaul for the platforms to be really looking and measuring the data.

And I think the platforms potentially have the ability to now work together in a cross-platform manner of, without getting too Big Brother, but how to track people from one platform to another to figure out what content they’re actually interested in, what are they watching, and then to make sure they have the most personalized experience to them. And I think really there’s sort of this hockey stick curve moment that I think is coming with personalization. And so whether that starts out with there being four different MrBeasts for every 100 million people, I think could be an interesting play.

And I think that you’ll probably start to see that in the next five to 10 years, and then hopefully 20 years, you’re only watching the content that is most applicable to you and that you love every moment of it, and looking at the retention data to make sure every moment that you could be watching content, you’re watching the best content for you. I think it’s a little scary, but I think it’s sort of the way the world’s moving of just personalized everything.

On Bad Bunny

Nick Tawil: So in terms of Super Bowl halftime shows, this year’s Bad Bunny, the hedges around his performance, and people were literally in the stands saying, “I can’t even see the show.” But the show is epic in so many ways across social media.

Revan Lazarus: I was one of those people.

Nick Tawil: Okay, there you go. But you’ve probably seen a million clips on social media about it, and that’s the point.

Revan Lazarus: Yeah, I think actually the Super Bowl was super interesting. So I was there, and yeah, I couldn’t see anything on the halftime show. And so I’m watching the big screen, but I think there’s so many. Those hedges. Funny story, we’re sitting, we’re in the end zone, and we’re watching these people run out in hedges, in grass costumes.

Nick Tawil: Yeah, yeah.

Revan Lazarus: And we’re like, “Oh, my God, the hedges are going to start dancing or something.” And we just figured out...

Nick Tawil: I thought the same exact thing.

Revan Lazarus: Right.

Nick Tawil: And I was waiting for it to happen.

Revan Lazarus: Yeah, totally.

Nick Tawil: It never happened.

Revan Lazarus: Me too. Never happened. And I started thinking about it, and I was like, Wow, it’s just so much more efficient than rolling out these giant, you know, fake hedges on wheels. Just dress people up in them and just have them run and it’ll be much more efficient.

Nick Tawil: Is that why they did it?

Revan Lazarus: Yeah, 100%.

Nick Tawil: Oh, my God.

Revan Lazarus: It just, think about it. You could have all these people just run and move and make this stage without actually having to build the stage, which I think was really interesting and also created some great social media content for them. But yeah, I think everything is becoming hyper-tailored to the growth sort of economy in the sense of, I think old Super Bowl halftime shows were probably great. You watch Michael Jackson or Rihanna, whenever that was five years ago. It’s like, that is probably a great experience for the people at the stadium. It was a horrible experience for basically everybody at the stadium this year. I mean, the music was phenomenal, but impossible to see anything that was going on.

And so I think it’s really saying, “Hey, we’re gearing this,” and I actually thought this was a great stance, but because it was so controversial and so many people didn’t like it, it was like, “We’re going to make sure everybody sees it, and so we’re going to tailor it for the perfect TV, social media content, and we’re going to blow this out, because who cares about the 80,000 people that are here? We care about the 800 million people that are going to see this,” which I thought was awesome. And so big Bad Bunny fan. First Bad Bunny concert 2017. So I’m an OG. Yeah.

Transcript

Nick Tawil: Hey Revan, how’s it going?

Revan Lazarus: Good, how are you?

Nick Tawil: Good, good. So why don’t you walk me through exactly what you’re up to and what you’ve built at Jamie AI?

Revan Lazarus: Yeah. Well, first, thanks for having me. Super stoked to be here. So at Jamie, we are an AI platform for podcast networks and digital sales teams. We essentially allow sellers and the whole content organization to understand their content and their portfolio at a deeper level and then use that content and that data to help make sales and production materials like custom decks, run of shows, stuff like that, and then be able to query across the entire content suite to figure out what’s exactly working, what’s not working, and then what’s going to work for brands.

Nick Tawil: So with that description, help me think about it in terms of actual show production, pre-production, production, post-production, and marketing and social media, the whole gamut, the whole suite.

Revan Lazarus: So we mostly focus on the pre-production side. Typically what happens is we’ll ingest your entire portfolio, but specifically on a show basis. We’ll analyze what has actually worked based on retention. So figuring out this giant retention graph, which is an L-shaped graph that has all these peaks and valleys, which will be on this video as well, and then figuring out at scale, based on those retention spikes, what is actually working for your audience, what’s not working, how can you improve your hook, your transitions, your editing. And so when you are prepping for an interview, you know exactly what questions are going to create those spikes, or at least more so of that, and then additionally put together a full interview map from your guests.

So for instance, if you’re researching me or somebody, typically our guests are a little bit more famous than myself, you can look at their past interviews, can figure out what’s actually worked well on social for them, and then do the full research. So watching up to 500 hours of content to figure out exactly what they’ve talked about before, what they haven’t talked about, what actually did well, but maybe they’ve only spoken about it once. And then what you should really touch on based on what your audience typically likes, based on your past videos.

Nick Tawil: You’re already so famous to me. So when you’re communicating all this, are you working directly with talent? How big is that team? Maybe some examples.

Revan Lazarus: Yeah, so typically we don’t work with talent. We work with the producers or the networks that work with the talent. And so we usually are with the producers that are making those run of shows, those interview maps. And some of our customers are Wave Sports and Entertainment, which started New Heights with Jason and Travis Kelce. They also do Carmelo Anthony’s show, Andrew Santino’s show. We also have Dear Media, which has the Skinny Confidential and podcasts like Khloé Kardashian’s podcast. And then we work with a bunch of other great shows like Amon-Ra St. Brown’s show, who’s a big NFL player, and a suite of those guys.

Nick Tawil: So sports, pop culture, it doesn’t even matter the content that you’re covering. All that matters is that you have a system for this.

Revan Lazarus: Exactly, yeah. So an example is, we work with a few different shows at Amazon’s Wondery network. So that’s like Baby, This is Keke Palmer, which is a more pop culture show. We also work with a show that is Zach Sang’s show, which talks to music artists and producers and songwriters, and now they have other sports shows as well. So we work on those shows across the board.

Nick Tawil: When did you start?

Revan Lazarus: We started officially March 1st of building this product. However, I’d been producing a podcast for six months before that and doing all the editing and pre-production and doing all the ad sales. And so I feel like I’ve been in podcasting probably two years. But yeah, just building this probably a year and a half ago.

Nick Tawil: What’s the biggest change that you’ve experienced from beginning to now in terms of where you thought you’d be providing media services or production services to what you’re actually doing today? And how has AI affected that?

Revan Lazarus: Yeah, I think when we first started, there wasn’t a lot of buy-in from production teams with AI. I think that probably you and I are trapped in this bubble of tech and SF or even New York and LA. AI is a big deal and a lot of companies a year and a half ago just weren’t in that state of mind of, “Oh, AI is going to change the way we do everything.” And I think that’s starting to happen. But I think even at the grand scale, it’s not the way the world operates right now. So that has slowly started to be like, “Oh, we need to work on AI initiatives.”

And I think more companies have had budget now allocated for that and are open to experimenting, and especially top down, really saying, “Hey, this is going to change our business. This is an 18-wheeler headed straight for us, and if we don’t get out of the way or figure out how to stop it, we’re going to get crushed.” And so I think a lot of those teams have been more willing to be interested in what we’re doing.

Nick Tawil: The difference in attitude, because I’ve come across this a lot in some of the media projects we do at O’Shaughnessy Ventures, is what’s the biggest difference in narrative? When 18 months ago you’re saying, “Hey, are you thinking about this?” and they say no to AI, why? Versus why are they saying yes to AI today?

Revan Lazarus: I think a big portion of it is AI 18 months ago was pretty crap for what they do, especially on the creative side. Ask AI to write you a story or a book, it’s pretty horrible. And so I think it was people testing it out, ChatGPT-4 or 3, and doing it once and saying, “Oh, this isn’t good enough for what I want to do,” and sort of writing it off. Versus now, I think if you can show, “Hey, we’re trying to actually write line by line or give you very specific insights,” I think showcasing it like that versus saying, “Oh, here’s the whole story of how you should do an interview,” which is even how we started, has really grown.

And then I think additionally, especially with us, I always had thought we would be a sort of pre-production content tool because I actually originally, when I was producing a podcast, that was the thing I was worse at. Great at selling ads, but I was bad at doing pre-production. And so shout out to the guys here for doing all the production. But so I originally thought maybe a lot of other people have this issue or it’s a huge cost driver in a lot of other production companies. They’re spending a ton on producers. And I was like, maybe that shouldn’t be the case, or they should spend less, or producers should be working on more shows rather than just like three producers, one show, which is typically sort of how it was going. You’d have an executive producer, a regular producer, and an associate producer.

And now I’ve realized that attaching yourself from a business perspective to cost versus revenue is huge. And so we’ve been really focused on how do we make companies more money instead of how do we save them more money. I don’t really think anybody’s interested in saving money when they can just make more.

Nick Tawil: So that’s fantastic. Well, something I heard you say is they were just using it wrong, or the AI capability wasn’t there, or it’s just not something they were able to spend enough time on before they realized the value. Now it’s just much more apparent, but also you’re bringing that to the forefront for these people who may not be spending 24/7 thinking about it.

Revan Lazarus: Definitely, yeah. I think that, I would never say our users are using the product wrong because they’re using it how they think they should use it, right? So they’re always using it in the right way. We just have to adjust. And so I think that a great deal of it was the insights that we were pulling were just sort of lackluster on what a really good producer could do. And I think as AI has evolved, and especially we’ve evolved with our customers to figure out what do they actually want, because obviously me running a podcast, that’s one podcast versus a producer who’s done this for 10 years and works on five podcasts, is a little bit different in terms of the output they’re looking for.

And then also, just doing everything through a data lens can be really challenging with creatives because creatives obviously are like, “This is an art form to me and I know exactly how my audience thinks and how they work.” And so really convincing them to take a look at the data, which I think has happened a lot more recently. When you look at shows like Diary of a CEO or even Call Her Daddy, huge data-centered focus. I think a lot of it, yeah, you can tell. So when you look at the comments, sometimes you’ll see even on Diary of a CEO, Steven doesn’t ask enough follow-up questions or feels sort of heartless. And it’s because he’s optimizing for retention. So he’s not asking the follow-up question that’s a weak transition. He’s just cutting straight to the next question. So when you feel like, “Oh, I’m sort of done with this answer,” you’re already onto the next question. And I think it isn’t the natural flow of a conversation. So when you watch it, you’re like, “This guy’s mom died and Steven wasn’t that heartfelt about it.” And it’s because he’s like, “How do we keep the viewer staying for longer?” And so there’s a give and take to everything. But when you’re really optimizing for retention and for views, I think it does work. His channel has grown dramatically in the past year and a half. And I think a lot of it is because of their optimization on the data side.

Nick Tawil: So the willingness for a show to take on a data analytics approach and really focus on that, does it matter how big the show is, or is it literally any side show, any podcast? This is alternative media, right? So it doesn’t cost a lot of money just to produce one episode of a podcast if you want to do it on the lower end. Does it matter, or does the size of the show matter?

Revan Lazarus: Yeah, I mean, I think always the size of the show is going to show more impact on the changes that you do. I think a lot of the time that on a smaller channel, you’re really looking for that human connection, so you’re really hoping that somebody falls in love with the content that you’re making. And I think the optimizations can actually happen later on. So for instance, if you’re starting a podcast, what you’re really going to want to do is just define who your audience is and make sure that they love your content, regardless of the optimizations. I think the optimizations come a little bit later when you’ve grown your audience and now you can say, “Okay, how do we grow to a bigger audience? Or how do we expand our pool?”

One thing I love about MrBeast is you’ll look at his old videos. There’s no optimization, retention, anything, right? He’s saying Logan Paul a million times in a row, right? Or something like that. It takes him 48 hours, something crazy. It’s like, there’s no retention there. Nobody cares about if you’re going to watch the next second. And especially a lot of the early stuff is like, how do you just build that audience? But now that he has the audience, he’s like, “Okay, how do we optimize this to keep people watching for longer, to attract more people?” He’s got this purple cow theory. He wants to do stuff that nobody’s ever done before so that you click on his. “I trapped two pilots in a plane for 100 days. The winner gets the plane.” It’s like, all right, there’s not a video like that that exists on the internet. And so then it’s like, “Okay, how do we optimize?” But initially you just have to have an audience that truly loves what you’re making. And I think a lot of that just comes from being authentic and being yourself and then figuring out the optimizations later.

Nick Tawil: It’s no secret that people want to know everything about their audience and demo matters. What are the most non-obvious characteristics of demo that you think have an outsized impact on a show? Well, let’s walk through some. Let’s walk through some of the obvious ones. It’s like geography, age, gender, what else?

Revan Lazarus: Yeah, I don’t know if you have any control over your demo and really, obviously you can do paid media to a certain demo and market towards that demo, but I’m not sure if that actually gives you an advantage. I think there’s unique advantages to every demo and it’s just about how you position, right? So older demo’s going to have more money to spend, right? So you can say that to advertisers. Younger demo’s going to be more interactive with your content. They’re going to watch more of it. So I think there’s pros and cons to each of that. What I would say is you just want a demo that is obsessed with you in any realm. The same way the older generation is obsessed with the news, Anderson Cooper and whoever, right? They’ll watch anything that he does. Versus you have younger audiences that will…

One I say is a great one is this guy Jake Shane. Jake Shane is probably, I don’t know how many followers on Instagram that he has now, maybe 2 million. But his audience is so deeply connected to him, will watch whatever he does and performs at such a high level where it actually doesn’t matter that he has 20 million followers. His 2 million are real 2 million that all love him as their favorite. And so you’ll look at Forbes puts this out on creators who made the most money. Jake Shane is continuously at the top because his audience really cares about everything he does.

So whether that’s a brand promo or an event, his audience shows up. Versus you’ll have other creators that have 10 times as many followers, but it’s sort of loosely following to where they don’t really care. A lot of examples I give is men or women that are very attractive but don’t necessarily have that connection with the audience. And so they have a lot of followers because people care to see what they’re up to, but they don’t really interact with their content. Versus somebody that just really cares about their audience, their audience really cares about them and then has that massive pull. So I don’t really think it’s a demo that necessarily matters. It’s just how strong can you get people to connect with you? How many people can you get to show up for you if you need? And so I think that is the main thing I would look for when building an audience is how deeply are people connected to your authentic self.

Nick Tawil: Do you put a lot of thought into literally people showing up for that content creator or for that person, in terms of real-life events or physical events? And does that even, is that within scope of what you’re thinking about?

Revan Lazarus: Yeah, I mean, on the sales side, a lot of the stuff that people are starting to sell is personal appearances, social media creators or comedians and anybody doing podcasts. And I think that, obviously having that backing of like, “Hey, we can get 20,000 people to show up for a venue,” is huge versus, “I think we’re going to struggle to get people to come to this thing.” And I think you’ll see that at big tentpole events, whether it’s the All-Star Game or the Super Bowl or Grammy parties or whatever it might be, that saying to a brand like, “Hey, we can get real pull here,” is actually the difference of millions of dollars versus not having that in your back pocket.

And I think there’s plenty of creators that can’t offer that because they just can’t get people to show up. But there’s also plenty of creators that probably can get people to show up and should. And I think that’s a big lever that’s not being pulled right now.

Nick Tawil: When these creators are pulling on these real-life events, how often do you recommend, or how often do they want to have some sort of third-party sponsor as a part of that event? Always? Or are they just saying, “You know what, this is going to be somewhat closed off” always?

Revan Lazarus: Yeah, always. I think there’s not a lot of opportunities for creators to make money outside of third parties or starting their own company, which is super challenging. And I think it’s great that creators are now full-scale businesses. They are the marketing, operations, they are the product, and they can create separate products. But I would always say, if you can get people to show up for you, I think doing personal appearances with a brand is super underrated. I know obviously you have things that are maybe a closed-off thing, but I think that’s because the creator just wants to have some authentic time with their fans. But I would say when it comes to tentpole events, it’s Coachella and stuff like that. Make your money. So I’m all for that.

Nick Tawil: Tell me a little bit about that because we were talking about that the other day, how the use of social media hasn’t really changed one generation to another. And it’s like the first time in history where you’ve got one older generation kind of doing the same thing that a younger generation is.

Revan Lazarus: Yeah, I think just in general with technology, you don’t really see generations shift that quickly to new tech, whether it was software or the iPhone or social media with Facebook. I think a lot of it has been sort of slow growth and slow adoption. And now I think with short-form content, I think it’s allowed plenty of the generations to sort of come together in the sense of 8-year-olds are watching TikTok and Instagram and 80-year-olds are watching TikTok and Instagram. And I don’t think that’s ever really happened in a technology shift.

I mean, even if we think about AI, we have this group of, call it 12 to 30-year-olds that are all in on AI, and then maybe a small section of tech executives that are really big on it, or just company executives, but that’s really it. This middle section doesn’t really exist. And then the upper section, the 60-plus, it’s not really interested in using AI, or if they are, it’s a very slow adoption rate. And I think one of the things that’s super interesting is how simple and easy short-form content has been and also how addicting it’s been, for good or for bad. But I will say, whether it’s my parents or my friends’ parents, plenty of people are constantly on the use of short-form content.

And I think that’s why the digital market in terms of the advertising world has grown so dramatically. I think it’s something like $700 billion on digital ad spend in the past year, which is insane.

Nick Tawil: It’s so large you can’t even really...

Revan Lazarus: You can’t even measure it.

Nick Tawil: Can’t even really appreciate how big that number is.

Revan Lazarus: Yeah. And so I think it’s just, it’s a really interesting time both with AI, but even just in general on social media that you have basically everybody in the world on one technology, which is a new technology. I mean, short-form content really started to pick up 2019 is my guess, 2020. And so within six years you have probably 100% of the demographic using a piece of technology. I think it’s pretty insane.

Nick Tawil: How are sales teams differentiating themselves then in this market?

Revan Lazarus: Yeah, good question. I think a big thing with sales is trying to prove that your audience has a unique fit with this brand. And I think a lot of it has been typically like, “Hey, X company, you have budget and we have a great product,” and there’s not much overlap. And I think that we’re starting to see this world of advertising with short-form content, long-form content in general, really see a dip in perceived ROI. I think for a long time it was like, “Oh, we’ll have creators or we’ll have podcasters promote the product and everybody will know about us and we’ll do more sales because everybody knows about us.” So brand awareness. And I think now, I think brands are starting to realize, one, we have the power of social media too in our own right. We don’t need massive creators. We can use micro-influencers or hire our own marketing team to do influencer where we don’t have to pay them more than their base salary.

And so I think you’re starting to move to a world in which everything is turning ROI-based. So those are direct response brands. But even for the brands that aren’t direct response or don’t need to see a huge ROI, like Pepsi or Coca-Cola, what they need is real proof that there’s an audience overlap. And I think that’s what a lot of people are struggling to do. I mean, if you’re a sales team and you’re managing 25 shows, good luck watching all of the content, good luck looking at all of the personality social media pages to see who’s actually using X products, who’s actually talking about certain things. It’s just at the scale, even with the AI models, it’s impossible to figure out all of this.

And so that’s something we’re really focused on, is providing proof behind the pitch. So figuring out across people’s socials, like, “Hey, maybe you’re an agency and you rep a thousand creators and you want to look who’s drinking Pepsi, right?” And so you’ll look and you’ll say, “Oh, wow, we have 50 creators that in 40% of their vlogs drink Pepsi. Great. We can clip that, send that to the brand and really have a differentiating factor,” rather than just like, “Hey, this makes sense because we have all these creators and you should do a deal with us.”

And then I think additionally, there’s a world in which sales teams need to get creative about the pitch. So that is appearances, that is doing short-form personal, which is just starting to, I think, ramp up. I think some companies, like our customer Wave, has been doing that for a long time, and now I think sort of the general market has realized, “Oh, we need to both be selling personal and podcast.” So both on the company level, but also on their individual. And that’s how we’re going to get the most bang for our buck. And figuring out deals to which we can get some sort of portion of that to really incentivize this full holistic integration.

Nick Tawil: I see how brands may struggle to one, identify ROI, or if the budgets are so big, whether that’s even a priority. It’s more about, like you say, audience overlap and real interest, where their brand awareness actually makes an impact. But for podcasters, for creators, the ROI is the brand sometimes, isn’t it? Right, it’s their sponsorship dollars. So how do creators think about ROI? Is it only ad sales and sponsorships?

Revan Lazarus: There’s starting to be this boom, at least with the bigger creators, of figuring out how can I be a part of the marketing engine in a deeper way? Or how can I be part of the company in a deeper way? And I think that’s allowing creators to ask for way better terms. So for instance, like, “Hey, I’m going to promote this, but I also want equity in this company, or I also want backend on my promotion. So yeah, you’re going to pay me a million dollars for this promotion, but then I want two and a half percent of everything I sell.” And so I think it’s starting to get to a point where creators are recognizing their value if they have it, right?

There’s still a lot of proof to be had, but if you are recognizing that this is working, how do we get some sort of percentage of the upside? And then additionally, I think with creators, a lot of it is working with brands that you see a future with. One thing that I’d say to a lot of the creators that we work with is there’s no point to work with a brand for three months and then never work with them again, because you’re essentially branding yourself alongside them. And what you want to look for is brands that are on the up and up that you can grow with. And as they grow, maybe there’s more opportunities for you to grow alongside them.

And so I would really encourage creators to sort of define what type of creator they are and work with companies that they truly love rather than just for a check, which I think a lot of people fall into because they need to. And it’s like if you built a social media following and you want to do it as your full-time job, you’re going to have to make money somehow. And the platforms aren’t going to pay you enough. And so really figuring out what brands do you see a future with is, I think, super important.

Nick Tawil: While podcasting is alternative media, it’s also been around now, I’d say for a good hot minute. What does this look like in 20 years?

Revan Lazarus: Yeah, on that note, shout out to my dad. My dad had a podcast in the ‘90s. He would do interviews with Broadway producers and put it on a website. Find the link. But yeah, shout out to my dad. I think in 20 years it looks super interesting in the fact that I think things are going to have to be a lot more personalized. I think that we might start seeing versions of creators or podcasters that are hyper-specific to the individual. One thing I’ve been saying for a long time is, MrBeast has 440 million subscribers, and I think there will be 440 million different MrBeast versions for each person based on the data. And so I think this has to be a platform overhaul for the platforms to be really looking and measuring the data.

And I think the platforms potentially have the ability to now work together in a cross-platform manner of, without getting too Big Brother, but how to track people from one platform to another to figure out what content they’re actually interested in, what are they watching, and then to make sure they have the most personalized experience to them. And I think really there’s sort of this hockey stick curve moment that I think is coming with personalization. And so whether that starts out with there being four different MrBeasts for every 100 million people, I think could be an interesting play.

And I think that you’ll probably start to see that in the next five to 10 years, and then hopefully 20 years, you’re only watching the content that is most applicable to you and that you love every moment of it, and looking at the retention data to make sure every moment that you could be watching content, you’re watching the best content for you. I think it’s a little scary, but I think it’s sort of the way the world’s moving of just personalized everything. I mean, you have AI agents working on everything to make your life as personalized and perfect for you. So I don’t think content would be any different.

Nick Tawil: Mass personalization, mass customization, fascinating. But doesn’t that go counter against one of the things that’s most important between the creator and the audience, which is keeping an authenticity or a trust factor? And if they think they’re just watching some AI-tweaked version of MrBeast, does that make it less compelling?

Revan Lazarus: Probably. I don’t know if people will care is the thing. I think content, short-form content, it’s like a drug. I think if you’re just watching the perfect thing for you, I don’t know if you actually care about the authenticity and that you feel this connection. And I think there will be creators that will be on their own and just have that authentic connection, but I think there will also be people that don’t exist and that are creators. So AI creators that are making the perfect content for you. And so whether that’s actually MrBeast or that’s MrBeast-style videos or whatever it might be, I think you’ll have this duality of AI creators and regular creators and just let the best win.

And I think that you probably will see, just because of the bulk content that these AI creators can make that is much better content and perfect for you, you’ll probably start to see a shift in adoption there.

Nick Tawil: So I want to say it here. Just because the creator doesn’t exist, i.e., it’s an AI creator, doesn’t mean there can’t be in-real-life events.

Revan Lazarus: Yeah, totally.

Nick Tawil: I mean, because there’s holograms, there’s, I mean, the robots. I mean, there’s a lot of ways to bring an AI creator into the physical world in some sort of location.

Revan Lazarus: Totally. And I think a lot of these events that are based around creators, whether it’s tentpole moments, so Coachella and the Super Bowl, don’t actually have a lot to do with the creator themselves. I think it’s people that like the creator all being around each other. And I think the creator as the center point is super interesting, but and maybe there’s a meet and greet and stuff like that, but it’s actually not the driving factor. It’s like, “Oh, so-and-so is throwing an event. And great, I’ll go and I’ll support them, but also get to be around everybody that’s sort of like me that we all have this shared interest.” So I don’t see why it wouldn’t be different. And yeah, you could do holograms and all that stuff. And maybe 20 years we’ll have robots, who knows?

Nick Tawil: Yeah. I would argue in terms of Super Bowl halftime shows, the one that we just had this past but what’s his name?

Revan Lazarus: Bad Bunny.

Nick Tawil: Bad Bunny. So in terms of Super Bowl halftime shows, this year’s Bad Bunny, the hedges around his performance, and people were literally in the stands saying, “I can’t even see the show.” But the show is epic in so many ways across social media.

Revan Lazarus: I was one of those people.

Nick Tawil: Okay, there you go. But you’ve probably seen a million clips on social media about it, and that’s the point.

Revan Lazarus: Yeah, I think actually the Super Bowl was super interesting. So I was there, and yeah, I couldn’t see anything on the halftime show. And so I’m watching the big screen, but I think there’s so many. Those hedges. Funny story, we’re sitting, we’re in the end zone, and we’re watching these people run out in hedges, in grass costumes.

Nick Tawil: Yeah, yeah.

Revan Lazarus: And we’re like, “Oh, my God, the hedges are going to start dancing or something.” And we just figured out...

Nick Tawil: I thought the same exact thing.

Revan Lazarus: Right.

Nick Tawil: And I was waiting for it to happen.

Revan Lazarus: Yeah, totally.

Nick Tawil: It never happened.

Revan Lazarus: Me too. Never happened. And I started thinking about it, and I was like, “Wow, it’s just so much more efficient than rolling out these giant, you know, hedge, fake hedges on wheels.” Just dress people up in them and just have them run and it’ll be much more efficient.

Nick Tawil: Is that why they did it?

Revan Lazarus: Yeah, 100%.

Nick Tawil: Oh, my God.

Revan Lazarus: It just, think about it. You could have all these people just run and move and make this stage without actually having to build the stage, which I think was really interesting and also created some great social media content for them. But yeah, I think everything is becoming hyper-tailored to the growth sort of economy in the sense of, I think old Super Bowl halftime shows were probably great. You watch Michael Jackson or Rihanna, whenever that was five years ago. It’s like, that is probably a great experience for the people at the stadium. It was a horrible experience for basically everybody at the stadium this year. I mean, the music was phenomenal, but impossible to see anything that was going on.

And so I think it’s really saying, “Hey, we’re gearing this,” and I actually thought this was a great stance, but because it was so controversial and so many people didn’t like it, it was like, “We’re going to make sure everybody sees it, and so we’re going to tailor it for the perfect TV, social media content, and we’re going to blow this out, because who cares about the 80,000 people that are here? We care about the 800 million people that are going to see this,” which I thought was awesome. And so big Bad Bunny fan. First Bad Bunny concert 2017. So I’m an OG. Yeah.

Nick Tawil: And human stages.

Revan Lazarus: And human stages, yeah. It was really great. Yeah. What a show.

Nick Tawil: Let’s talk about the AI creator system overseas. What’s happening here? China, generative AI generally. I know, I mean we talk about it all the time already just within our teams. How are you seeing that use in your own workflow? But also what are some competing forces there that kind of raise your eyebrows?

Revan Lazarus: Yeah, I mean, I think short-form AI content in general is super interesting. I think you’re starting to see more and more of it on Instagram, TikTok. But yeah, especially these Chinese TikTok competitors, I think a ton of the content, maybe the majority, is AI-driven content. And I actually think there’s a huge growing force there in terms of we don’t really care again if this is a human or not. We just want the best content. And I think that you’re starting to see a lot of that. I will say sometimes I’ll watch a piece of content on Instagram Reels or something and I won’t realize it’s AI until halfway in. And I think the models are just getting that good.

And I think even TikTok’s competitor in China actually has a video model that they are building.

Nick Tawil: Talking about Kuaishou?

Revan Lazarus: Yeah, so Kuaishou I think has an AI video model within their app. And so I think it’s just starting to become more and more. And so I wouldn’t be surprised if TikTok then allows you to make AI videos and has their own model and stuff like that just to encourage the bulk of content. Because these platforms are in the business of showing you the most content and keeping you on longer so they can show you more ads. And so it’s to their benefit to just have more content on there because if you can service more people and they’ll watch for longer, it benefits them.

And so I know Meta has AI content flags and stuff like that, and I think they’re doing that to make sure people are safe and there’s a difference of misinformation and stuff like that, but I don’t know at scale if that’s going to keep up because I think people will just want to watch.

Nick Tawil: Or if it’s even defensible.

Revan Lazarus: Exactly.

Nick Tawil: It’s like you can’t stem the tide.

Revan Lazarus: Exactly. And so I think that’s super interesting. And again, if you’re giving me the best content for me, I don’t really care if it’s AI, if it’s informational and I’m getting my latest news that’s perfectly curated to exactly what I want. I don’t care if an AI is telling me, “Here’s the news and this is everything that happened,” versus some talk show host or some news anchor.

Nick Tawil: How are brands thinking about it though?

Revan Lazarus: I just have no idea. I don’t really have a good answer for that. Yeah. I don’t know. If I was a brand I could probably have a better analysis. But I mean, I think in terms of how I see brands using AI is there is so much marketing material that is now being pushed out. Whether it’s Nike or Porsche, they’re all using AI B-roll. And so they’re taking photos of the car, of the shoes and saying with AI, “Let’s make this look in certain ways.” And so I think they’re doing a lot of marketing around AI video and AI photos and stuff like that.

But I’m not necessarily sure how they’re thinking about it with creators and podcasts, but I know the assets they’ve been able to make and how quickly they’ve been able to make them is unparalleled.

Nick Tawil: Yeah, the commercial industry has been one of the earliest adopters of generative AI and infusing that in the commercials, and brands don’t seem to have a problem with it at all. The economics are just really compelling. And so it’s interesting how generative AI, one, the quality of it, but also where it takes hold in certain parts of entertainment and media. It’s not necessarily a completely linear adoption or an all-in-one adoption. It’s happening in some places faster and sooner than others. That’s just a result and I think a factor of the quality of what you’re dealing with. And as that stuff gets better, I think one of the holy grails is going to be actual long-form film.

And once you start talking about that, I don’t think it necessarily replaces Pixar tech or other types of film formats, but it’s just another type of film that people become used to and start enjoying consuming.

Revan Lazarus: Yeah, I mean they put Paul Walker in one of those Fast and Furious movies after he was dead. So it’s like, that was CGI.

Nick Tawil: It was CGI.

Revan Lazarus: It’s all the same thing, right.

Nick Tawil: It’s a different version, different tool.

Revan Lazarus: And I think there’s a lot of, AI is catching a lot of flack for the name and what it is, but people have been doing some version of making things that didn’t exist for a long time within content. Whether that’s making something look like New York, but it was filmed in Canada, right? It happens all the time. And so I think just because it’s tech doesn’t necessarily mean it’s wrong or it’s different tech. And so, yeah, it’s been happening forever, and I think it’s just part of the process. And I think even for these animators that their job’s getting taken, it used to take them four years to make a movie. Now it takes them, in terms of the animation, a couple weeks. That’s pretty awesome.

Now they get to work on a bunch of projects. I know Pixar in general, they had to pitch three movies. Each writer or each animator had to pitch three different movies and they would choose the best one. And so now if you have a team of 10, instead of pitching three, why not pitch 30? You have all the tools to do so. And so I think it actually just makes content better, and I think it makes the level of content you can create that much more interesting. And so I think it just benefits the whole industry and benefits the audience. And I think that, I think if it had a different name or if it was associated with something more positive, I don’t think anybody would have an issue.

And I think one thing I’ve been seeing is these commencement speeches and how the graduating class is booing anytime AI or artificial intelligence is mentioned. Have you seen those?

Nick Tawil: No, I haven’t.

Revan Lazarus: Okay, so it’s like somebody speaking at UCF or at really any school, and I saw this whole compilation. It’s like, they’ll mention, “Oh, the growth of AI or artificial intelligence,” and the whole graduating class booing. And it’s like, I think it’s insane. And I think we are also trapped in this tech world and venture world. And so we see all the positives, but I think a lot of people are just seeing this as a negative. And I would hate for that to actually be the case because I remember watching that and I was like, “AI did your homework. Why are you booing it? This helped you get through college.” So I think that’s my take.

Nick Tawil: That’s great. No, to go back to, even go back to movies, even how I think certain types of formats of movies will come back into fashion. Like the original When Harry Met Sally rom-com doesn’t really get made anymore, or if it does, not for the big screen. If it does, it gets made as an episodic or a miniseries format or it’s on Netflix and it’s just a different format. But something like that comes back into play when AI can generate the setting in every single scene and it’s a specific spot in New York or in Paris or wherever, and suddenly the production value, the production costs of that film just go way down.

And yes, you can make it faster, but also you can make a different type of movie that people probably haven’t seen in 10 years or 20 years.

Revan Lazarus: Oh yeah, you can make a movie you want to make without the budget of the studios needing to give you $300 million to make this movie.

Nick Tawil: Yeah, there might be a way, there might be a renaissance in the pull away from Marvel Cinematic, huge big-budget movies where that becomes 90% of what you see in theaters and maybe goes back down to a lower percentage. But because other types of films come out.

Revan Lazarus: I think something that’s super interesting is probably, it’s not content-related but just the, I think the overall job creation that will probably happen with AI.

Nick Tawil: Tell me more about that. Because everyone talks about AI and the scarcity mindset, it’s going to replace jobs, but I actually think it’s going to, anytime we talk about innovation, I think there’s a net positive that happens.

Revan Lazarus: Yeah, I mean I was talking about this last night at dinner, but even if you just think about the HVAC industry, how many jobs are going to be created to cool all these data centers? Hundreds of thousands of jobs in the US in HVAC that will probably pay pretty damn well. Or I heard a bunch of actually different people give this analogy, but about radiologists and it’s like, “Oh, AI can now analyze X-rays so all radiologists won’t have jobs.” It’s like, no, people are just going to get more X-rays or people are going to need to understand every little thing a tiny bit better. So there’s just going to be more jobs or there’s going to be more software engineers, not less.

I think this is a huge one that everybody’s like, “Oh, rest in peace to all the software engineers,” which I don’t necessarily believe is true at all. I think there are so many things in our daily life that we could use software for that we don’t because it’s too expensive to build for a marginal benefit or this technical barrier of knowledge. Exactly. Or it’s like, “Hey, that doesn’t really matter to have software because I’ll just get by.” And plenty of things in my life that could be improved by software that I’m just like, I put up with or I do the process because it is what it is and it’s not worth building a piece of software for it.

But now, because you can build software for anything, I think there’s just going to be 100x the amount of software needed to be built and software engineers will need to build that because in order to make it production-grade, it can’t be vibe-coded. It just won’t happen. I think what you’ll see is a revolution of everything just getting software. And so I’m very excited about the industry in general. And one thing I heard, did Jeff Bezos say yesterday, was, “This is like digging out your basement with a shovel and somebody comes along with a bulldozer and it’s like, ‘Let me help you.’ And it’s like, why wouldn’t you say yes? It’s just going to help.”

Or even the fact that right now most households are dual-income, but it might not need to be, it might need to be single-income because you can just be that much more productive. I think there is this, I think there’s this mindset that AI is going to hurt. And I think that it probably will hurt if you think that or if you don’t adopt it, right. And I think it’s all a mindset. I just turned 25 and I was probably going to work a regular job and I was not a programmer. I was going to be working in podcasting and selling podcast ads, which is a great business, make great money. But I think the level of impact that I’ve been able to have because of AI and just adopting AI, I get to work with phenomenal people, hundreds of people that are impacted by our product and by what we do is the most rewarding thing ever. Money aside.

And I think so many people don’t realize you can change thousands of people’s lives by saying, “Wow, I have this pain point. If I solve this for myself, I can probably solve this for a lot of people.” And I think it’s never been easy to start a company. I think it’s never been easier to build a product and get it out to millions of people with short-form content. And so I would say all of these new grads that are booing AI, you have the opportunity to one, make a shit ton of money right now because you are the right generation for it. But also you can just benefit your own life. If you’re going to go work a corporate job, build AI agents to automate the stuff you hate about your corporate job. There’s a million things to do.

And so I think you just have to dive in because I think this is the biggest revolution in history. And I’ve been going to AI conferences for four years before...

Nick Tawil: I’m sure the nature of those conferences has changed even.

Revan Lazarus: Oh my God, it used to be like, “AI is the biggest thing that’s going to happen,” and now it’s like, “Okay, it’s here and we thought it would be a quarter of the size.” And I think this is in my opinion 10 times as big as the internet. I think this is going to be every company. I think you’re actually going to start to see a breakup of these semi-large companies. I think there’s going to be these huge companies which are these model companies, OpenAI, Anthropic, Google, et cetera. And then you’re going to see all of these small niche companies in AI and in software that are much smaller market cap.

And I don’t think there’s going to be any $500 billion software companies that exist because they’re just going to get crushed by the models or they’re going to get crushed by the really small company that’s just doing it better. And this is, I think this is a big thing. Everything that can be hypervertical is going to exist and then everything that isn’t is just going to be these large language models. So insurance, large language models. But maybe specific type of unique insurance that’s a super one-off, like very much these small companies or even in podcasting.

Nick Tawil: Classic cars insurance.

Revan Lazarus: Exactly. And so I think you’re going to have these model companies, these five model companies that are going to be worth tens of trillions of dollars. I mean Anthropic is going to be worth a trillion dollars this year. They’re going to do a trillion dollars in revenue in a few years. And then you’re going to have all these smaller companies that are super hypervertical and have the ability to just service their customer better than large language models. But the companies in the middle that are just doing regular software that are now worth a couple hundred billion, I don’t think stand a chance. And I think it’s a very concerning time for those companies. But I think everybody else that’s fresh, it’s like how can you pick something that’s a smaller industry?

And I think the investing world too from your side as a VC is there are companies that are going to be worth trillions of dollars and there’s probably companies that can just be worth billions of dollars and that’s probably it. There’s not going to be $100 billion companies in software. I think it’s just going to be the models and everybody else on the smaller side. And so it’s really interesting time to be a semi-large company. And I wonder how Salesforce and all these other companies feel. And I think they obviously have a great integrated product that’s very sticky. And so I think the short term is probably pretty bright. I mean the revenue keeps going up and up. But I wonder, 20, 50 years from now, what does that look like?

Because obviously this breakup of the small companies and the massive companies isn’t going to happen in the next five years. People are still stuck in their workflows and stuff like that, but slowly can have Anthropic make you a CRM. You can have it do all your automated emails, you can have it build your entire Salesforce pipeline. You can have it do data enrichment, you can have it do everything. So it’s an interesting time or Figma, stuff like that. Figma is great and it helps companies ship software. And I actually, I’m sort of bullish on Figma. I think nobody is, but because of the software boom, I think you all need some version of Figma because cloud design is great but you still need it to be productized. And I think Figma has a lot of room to grow.

But even stuff like that, it’s not a $100 billion company, I mean the market just showed that. And so I think you’re just going to have these companies that are super niche and these companies that are extremely general and nothing in the middle.

Nick Tawil: I think if you have nothing in the middle, what you have is really a larger SMB economy. So small-medium-sized businesses that oscillate between making a run at growing but also are lifestyle businesses run by what we would have considered mom and pop maybe 10 years ago, but being run by mom and pop at that level and they become lifestyle companies that are actually profitable. And it’s just a different type of middle class to anywhere from lower to middle to upper-middle class that comes into existence. And if that’s the case, I think you have to think about how that eventually gets consolidated because there’s just always going to be a recycling. There’s a cyclical play.

When you have a decentralized set of companies and they’re all maybe hyper-specialized, I think you always have another person that comes in and says, “How can we combine, how can we aggregate and how can we optimize even this?” And so I don’t know if that happens when you have the tens of trillions of dollars type companies that are in the background. Because especially in advertising and advertising technology a decade ago, one of the most common refrains when an ad tech company was pitching an investor is, “What if Apple decides to cut you off, cut you out? What if Google decides to cut you off or cut you out?” And that’s the same exact narrative that’s going to begin happening where like, “Great, you’re this type of hyper-specialized, verticalized company. But what if you lose access or what if Anthropic or OpenAI decide to do what you’re doing tomorrow?” And so there’s always a risk there. But what I think people realize if you kind of maybe go a level deeper is that Apple and Google never really kicked a lot of people out. And so it actually ended up being a huge net positive and an additional part of the economy that was able to just live.

Revan Lazarus: Totally. Yeah. I think obviously the model companies need the small businesses to pay their APIs and to keep them alive. That’s where the majority of the revenue is coming from, is from businesses. And so I think I’d be less worried on the niche stuff of what if they cut you out, but what if they do what you start doing? Or what if the models become so good that your niche company doesn’t matter? I think is super interesting. I do think though that the big company is never going to be able to service the specific exact customer and make them feel like this product was extremely built just for them, which I think is the difference. And I think customers will be willing to pay for, “This product was made just for me.”

Which is why I think these companies will be smaller because you can’t make that many “just for me” companies. And so Anthropic is not going to come and take your, even my business, the market’s not big enough, right. But are they going to do insurance? Are they going to do health care? Absolutely. Are they going to do finance? Absolutely. There’s a million of these other verticals that are trillion-dollar industries, which is why I’m sort of bullish on this take is you need to pick a niche, you need to monopolize the niche and figure out growth later. But you need to be really good at doing something that, yeah, maybe isn’t the biggest market in the world, but that you can make the “for me” product.

And that’s sort of what I say is I want the customer experience to be like, “Wow, they made this in-house for us.” That’s how I want it to feel. Then there’s only so much you can grow with that before you have to change up the way you think about your company and doing products. But it’s also why companies like Palantir and all these forward-deployed companies do really well because they go in, they look at your business, they spend a couple months doing it and they say, “Okay, great, we know how everything works, we’re going to make you custom software for you.” And so they’re actually, Palantir is a consulting company. They’re a software consulting company.

There is, as much as Deloitte or McKinsey that come into your business and, “Okay, yep, we know what’s wrong, we know how to fix things and we’ll make you software.” Yet they’re also getting the ARR multiples like SaaS companies, which is kind of crazy, but I think that’s sort of where you’re going. It’s just like, how can you make custom solutions for specific companies and specific niche industries? And then I think sort of what you were saying on that growth side is I think that these companies are going to be huge and I think that they’re going to be more nation-states than they are companies.

And I think that we’re playing a very dangerous game where you’re giving the power to five people and it’s just like you get into a point where they don’t want to be public companies because being a public company now sucks and their valuations.

Nick Tawil: Don’t say that to SpaceX.

Revan Lazarus: Yeah, exactly. But I think SpaceX would be a private company if they thought they could raise money at $1.75 trillion in the private markets. They just can’t. But you have Anthropic that’s going to raise $900 billion, where in the public market it probably can’t get $900 billion, but in private markets definitely can, no problem. And so I think they’re going to try to stay in the private markets for as long as possible, which leads them to just have less customer favorability when it comes to feeling a part of this company. I think that you’ll get to a point where if Anthropic or OpenAI was a public company and people could invest and they’d be happy for the growth, they’d want to see more.

You wouldn’t have, I think, so much booing at graduations because people could feel like they could take part in the upside. But I think they’re going to try to stay private companies for as long as possible and potentially not even when they go to fundraise in the public markets, not raise that much. I think SpaceX is only raising $75 billion of $1.75 trillion. And so they’re not giving up really any percentage of the company. And so I think it’s going to be really interesting to look at how these model companies operate and then also how they give back in a way to the people or else there’s going to be riots.

One thing I heard this week was, when Hershey’s was making their factory in Hershey, Pennsylvania, they made a theme park, amusement park, right? They have roller coasters. It’s like, “Yeah, sorry for creating all this traffic, noise and pollution in your town. So here’s an amusement park.” It’s like what is the equivalent to that for the model companies? Like, “Hey, sorry for putting a data center in your backyard and sorry for creating all this havoc. What can we do to give back?”

Nick Tawil: Universal basic income.

Revan Lazarus: Exactly, exactly. But exactly.

Nick Tawil: Well, as these companies get huge, back in 2022, 2023, there is actually a lot of discussion around how actual nation-states would have their own nation-state models, their own AI models. I think that conversation’s gone a little bit by the wayside just with the growth around the privates like Anthropic and OpenAI. But that could very well just come back into the dialogue, into the fold. These companies are getting so big that maybe they’re just partially owned or they’re heavily regulated to the point where it becomes like a phone company.

Revan Lazarus: Yeah. I used to think there was a scenario in which OpenAI could no longer raise enough money to continue to grow. They wanted to grow with their burn and so they were going to have to rely on the government. I no longer think that. I mean, I used to think six months ago that, “Yeah, I think they’re just going to grow so fast and I don’t think they’re going to be able to raise enough money and they’re going to be the most powerful company potentially in the world.” This is before Anthropic obviously went on a tear. But who’s going to fund them? The government. And then the government’s going to have an AI and then you’re going to be asking all your personal questions, right. And so all of this stuff in the same way of...

I think there was a couple of years ago there was this fear that quantum computing would basically break everything. And so that it would break all your communication systems. And so there was this scenario I had thought of in my head which was like, if it happens, and for instance, you can’t send any encrypted messages, everything is just out in public. The government has to create some anti-quantum computing phone, right. So now you’re on a government phone, right. And now they’re listening to everything you say. And there’s a world in which we’re...

Nick Tawil: Back to where we started.

Revan Lazarus: Exactly. There’s just this world in which it’s an infinite loop of just corruption of privacy. And I think there’s a world in which there’s stuff that’s scary. And I think these AI companies are verging on the scary side for most people. I’m obviously super bullish on these companies. I think these companies are great for the world, but I don’t think if they don’t start giving back to the public in some sense, I think there will be riots in the streets for real. So it’s going to be interesting.

Nick Tawil: I mean, short-term disruption would lead to higher rates of unemployment across younger populations, which is always a recipe for volatility and also a recipe for more socialist mindset I would argue.

Revan Lazarus: It’s been a pretty fun conversation.

Nick Tawil: I know, I mean you speak at a thousand words a minute.

Revan Lazarus: Yeah, this is actually me.

Nick Tawil: We got a lot here. Well, it helps when you’re an expert in something and you’ve devoted your life to something to be really good at it. I think you speak very quickly. Anybody would speak very quickly because there’s just a high degree of confidence and knowledge around it. So I think that comes through. So thanks for the time, thanks for coming out, and maybe we’re going to do another one of these.

Revan Lazarus: I’m in. Cheers.

Leave a comment

Subscribe now

Share

In this episode of Infinite Loops, hosted by OSV’s Nick Tawil, we sit down for a roundtable on the hidden global economy of secondhand textiles with Brian London, Marisa Adler, and Eric Stubin, all experts in the field. We discuss how the industry works, why fast fashion has made the problem harder, why 70% of the world uses secondhand clothing, what AI can and can’t solve, and why turning an old shirt into a new shirt is still much harder than it sounds.

We’ve shared some highlights below, together with links & a full transcript. If you like what you hear/read, please leave a comment or drop us a review on your provider of choice.

Links

Apple Podcasts

Highlights

70% of the Planet Wears Your Hand-Me-Downs

Brian London: When we say reuse, it’s useful I think just to kind of conceptualize what that really means. And I mean the stats I’ve seen, something like 70% of the world uses secondhand clothing. Something that probably includes US consumers that buy from thrift. But dozens of countries, it’s the main item that they buy. When people are living on a few dollars a day, it’s really the only affordable option. So that’s something in the profile of that in the book. The different benefits of our industry, again that no one really notices or sees much, is the environmental benefit which we can get into that. All the water and greenhouse gases it takes to create new garments. The charitable benefit. So you don’t even know how many billions of dollars go to Goodwill, Salvation Army, powering huge amounts of workforce training and other services like that.

Marisa Adler: And even the for-profit sector often has a charitable aspect to it.

Brian London: Sure, yeah.

Marisa Adler: Just wanted to mention that.

Brian London: Yeah, we’ll get back to that in a second because the collection part is a huge question too. But yeah, the third big benefit is that it provides affordable clothing to folks that otherwise really would have no option. So you see that every time. And we can get into this too about some of the barriers to trade a lot of times. But you’ll see every time they try to impose a ban or a restriction on used clothing in these countries, the people get up in arms because it’s such a hotly desired product. And sometimes there’s different forces at play, but it’s all around the world, it’s a hotly desired—

Eric Stubin: I’ve always looked at it in the following way in that demand always told the overwhelming story. I mean, demand for these secondhand products is global. And like you alluded to, Brian, two-thirds, I believe, of Africa lives on less than $2 a day. So you could really see, especially when you travel there and not for safari, but when you really travel and you walk in where people live and you see just how ubiquitous secondhand really is, it really gives you a distinct impression and you see the demand. And it’s not only Africa, I mean, it’s across the Americas, it’s throughout the world.

The World Wants America’s Old Jerseys

Brian London: But largely it’s a story of American soft power influence throughout the world. So in a lot of countries, I mean, I think in most markets a lot of times though, because of our, because of Hollywood, our sports stars, just like a lot of people here, they’ll be looking to have a LeBron James jersey or Jalen Brunson, go Knicks, jersey. Because American culture is kind of what they’re buying also.

Nick Tawil: And at the time of this taping, the Knicks are in game two.

Brian London: Okay, yeah, good luck tonight. And so, yeah, I guess traditionally over the decades, and as America’s role in the world changes or doesn’t change, I mean, that’s been sort of a constant because obviously we’ve been a major force around the world, definitely culturally still, and I think that plays a lot into it. But each country and each region has their own, whether it’s religious, cultural, weather, climate issues, they all have their specific items that they want.

What Does Vintage Even Mean Now?

Nick Tawil: For thrift and vintage, has there been a change? So it’s as hot as ever, but has there also been a change in where it’s happening? When you think of high-end vintage, you think of metropolitan areas like New York or Paris or London or LA. And I know Japan has a big Americana vintage market, but is this happening in other places as it continues to be a steadfast thing that consumers want or grow?

Eric Stubin: My sense is that there is large global demand for American vintage. I mean, Americana, American fashion is a big part of global fashion today. And it continues to be a lot of demand throughout the world for American vintage. Vintage, the term vintage has changed a lot over the last decade. Vintage typically sometimes means, what does vintage mean? Yeah, vintage. I mean, I think in the past, well, when I first started in this industry in the ‘90s, it meant ‘40s and ‘50s and sometimes even ‘60s as a decade in terms of what you were looking for. But obviously as time advances, that changes. Now ‘90s is popular and different fashion styles and what the vintage crowd is looking for, whether it’s flare leg, skinny leg jeans, that changes of course annually.

Nick Tawil: So as you’re sorting the stuff, you kind of have to be up on this.

Eric Stubin: Yeah, I mean for the companies that sell it and deal in those markets, they have to be very aware of what they’re selling and what they’re collecting or they’re not going to find it. But yeah, the world is always looking for American vintage and there seems to be continual demand for this, although that changes what constitutes it.

Transcript

Nick Tawil

All right, so I’d love for you guys to tell me exactly how this secondhand global economy works. And for a lot of people that don’t know about it, maybe the best way to go about it is to walk me through what happens after you drop off a bag of donated clothing to a Goodwill or a Salvation Army.

Brian London

So in addition to my day job in my industry position, another role I have is baseball coach for Little League. And so I bring that because last week I was looking in our bag and I realized there’s a bunch of T-shirts in there. We have extra uniforms and also T-shirts and a fleece in there too, and no one claimed them. And that’s a moment. There’s a lot of moments like this where it comes up in daily life where it starts to seem like clothing really is almost started to be seen as disposable, almost like a Kleenex or something. And then another moment I think about it is we were at the beach for Easter, and you see these silly shirts, crazy shirts. And it’s almost just like any message you have just becomes a T-shirt. It’s almost like it really is just like printing T-shirts.

So I bring that up because we were talking before about hidden economies. And on the way here, I was looking as I walked. I started walking, I took Uber, but driving down or up, whatever I was doing, first of all the clothing stores, and then I started looking at each person wearing clothing, started to think how long are they going to wear that shirt? Where is it going to go? Just because I knew we were coming here. And it really is a fascinating story because you see them all the time. Everyone you look at is wearing something.

But the story before and after is a fascinating story that really never gets told. So I mean, a little bit more, I think the public is starting to look at it a little more. But yeah, I bring that up because we’re going to get into that story. So when you look at the shirt, what happens before? And I’m not an expert on this side, but that book Travels of a T-Shirt, shout out Pietra Rivoli, great book, tracks the globalized production of a T-shirt. So you got cotton growing in Texas, it goes to another country where it gets spun and then made into the cloth and then dyed and all this. So there’s all that goes into it, huge amount of resources that go into it and the volume of it. So that whole machine has just grown enormously.

And Marisa has all kinds of interesting statistics. She can say, she really normally paints that picture well, but it’s a staggering amount and the story of what happens after someone’s done with it. So people don’t really think too much about it. People tend to give it to Goodwill or another local charity, and then they think it’s just kind of, most people think that store sells it to people in need, which is a fair—

Nick Tawil

That’s what I always thought.

Brian London

Yeah, fair assumption. But long ago, even before this recent influx of huge volumes of fashion, they got way more than they could ever serve the public with, and monetizing it through thrift stores and then downstream, which we’ll talk about, became the best method to monetize all their programs, their job training programs, and a host of other charities. So anyway, to get back to the question, because they can only use a certain amount, and I’m not even sure what the current numbers are, but traditionally we would say maybe a quarter of it, 20% might sell to folks here domestically. Then the rest goes down a path that I think is equally, probably more interesting than the journey that it took to become a shirt.

So at that point, it’ll get consolidated into bales of used clothing. So we call it salvage, mixed rags, or different names for it. And it’ll end up getting sorted somewhere. And we can get to the history of that as much as you want, but it used to get sorted here in the United States. And as the cost of doing—that’s why I say sorting. And Eric will give a much more detailed picture of that. But essentially the job then is all this stuff has, over the years, the same entrepreneurial spirit that created that huge fashion boom, which became a fast fashion problem, also has over the years created much of the solution. And so that solution involves finding a home for all those pieces.

And so we get all the numbers, but between being reusable here or somewhere else around the world, being repurposed, being recycled, and increasingly we’re looking at this world of what else? How can you really turn that into new material? So it goes all over the world. Some of it goes all over the world and then comes back to the US. Some of it goes across the world to get sorted most efficiently and then to another home, and then sometimes it crosses borders again, and then it’ll get repurposed. So there’s infinite stories, infinite loops that these items go through. It happens every day. And the volumes really are staggering.

Nick Tawil

In terms of volume, just coming from the United States, any range of time is good. But you think about this in tonnage, right?

Eric Stubin

I think the stat that I’ve heard is about 2.8 billion pounds annually. That was the last EPA stat that I recall. Is that about right?

Marisa Adler

Yeah. When you, I think of this in terms of tonnage because of the scale. There’s sort of a little bit of a difference. When you’re in the industry, you think in terms of pounds because that’s how things are traded often. But when you’re looking at this from a systems view, looking at it from the tons perspective is more meaningful to a waste management professional. But 17 million tons were generated as waste back in 2018, and we don’t really have more official numbers as of then. But it’s a lot.

Eric Stubin

What’s the EPA stat that they’ve always quoted? Is it 3.8 or 2.8 billion? I’m having a hard time recalling that. I don’t know if we can look in the background. But there’s a stat that the EPA is always talking about and they typically use the number. I think they say that 3.8 billion pounds of textile waste are donated, recycled, that’s captured by large charities like Goodwill, blue chip charities, private sector collectors that go through the reverse supply chain, including US recyclers of waste.

Nick Tawil

So for people listening, the reverse supply chain, talk about what is that. What do you mean by that? And is that the recycling that happens with these donated textiles?

Eric Stubin

Yeah, I mean, just picking up on Brian’s example. So somebody gives away a sweatshirt because they didn’t, it wasn’t quite the right fit, or it could be that they used to wash the car and the dog with it and it’s reached its real end of life. So they go and donate that to a charity. Charity will look at that and decide whether it ends up in their thrift environment or not. And then often if it doesn’t end up in the thrift environment, it will make its way to a US or an international textile recycler. Like Brian said, they bale that material and then it’s sold on a spot market basis to recyclers around the world that then sort that material for highest use values.

And that’s traditionally how our industry has functioned for decades, sorting material for highest use values, extracting everything from at the top end, reusable quality clothing down to wiping rags and recycled fibers that are used in many household products like carpet batting and insulation for the hood of your automobile.

Marisa Adler

So if you look at it from a very simplistic perspective, the average consumer will drop off their unwanted clothing or textile items to a thrift store or into a clothing bin. That material, some of it gets sold domestically back to consumers here through thrift markets. The rest of it gets baled, it gets exported to some—there are some concentrated hubs across the world where there’s a lot of sorting and grading that happens and then it gets sent into reuse, reclaimed wiping cloth, and fiber recycling.

Nick Tawil

So there’s three main buckets.

Marisa Adler

Yeah,so about, the stats are about 45% of all the post-consumer textiles that are collected are funneled into a reuse channel. Just looking at this top down holistically, wherever in the world that reuse happens, 30% goes into reclaimed wiping cloth, which is basically you take a T-shirt, you cut it up, you take out all the metal parts and you resell it into an industry that uses it for cleaning or wiping.

Nick Tawil

What are some of the typical industries?

Marisa Adler

Automotive, you have the petroleum industry, the agricultural industry, the hospitality industry. It’s actually one of the secret underpinnings of the used textile trade in my opinion, because people just don’t realize that industry even exists. And there’s a lot of benefits that offsets the need for new wiping cloth material, new production or paper products and things like that.

Eric Stubin

I think reclaimed wipers are roughly about half of all wiping rags sold. And there’s a little fun fact, but there’s actually more than a half a dozen different grades of wiping rags. So depending on absorbencies and the absorbency rates and things of that nature, if it has to pick up a heavy viscous oil material or you’re cleaning up paint, there’s different preferences for different industries.

Marisa Adler

Yeah, it’s highly technical. They’re tools.

Brian London

That’s a whole sector of industry. So yeah, I don’t know if we’ve done an intro, but so I have my private company, Woodhouse and Shapiro, but I also currently serve as president of SMART, that’s Secondary Materials and Recycled Textiles Association. Eric was a past president on the board with me.

Nick Tawil

And so this is the trade association.

Brian London

Yes, we represent the whole spectrum of folks that handle this material one way or another, if you’re collecting it, sorting it, exporting it, importing it, repurposing it. Yeah. So the wiper division is a whole chapter of our industry that I’m not an expert in. We’ll move the material. Eric has been sorting that material for a long time. But yeah, it’s a whole world of its own and interfaces with a lot of big industries too, which I’m sure they probably don’t know the whole background of it either. But just to be clear because among us, we use certain terminology and I’m thinking when we say post-consumer textile, that’s a fancy word. It just means the shirt once I give it—

Nick Tawil

Right, old clothes.

Brian London

Post consumer. Yeah, old clothes. So and that terminology, we have different words for what we mean there, but a post-consumer textile.

Eric Stubin

And it also includes anything that we wear. I like to describe it as anything we wear, meaning footwear, handbags, belts, accessories. It really covers the full gamut of everything wear.

Marisa Adler

Yeah, there’s post—and when you’re thinking in terms of how waste management professionals classify waste, there’s post-industrial, which is off the factory, it’s cutting scraps or things like that. Pre-consumer. So all the things that the brands overproduce or don’t end up selling through in their retail stores, all that’s considered pre-consumer, which is a subsegment of post-industrial. And then the vast majority of the waste comes from post-consumer. That’s everything that’s been sold, worn, used and no longer wanted by the consumer.

Brian London

Yeah, but so we’re looking at these billions of pounds of post-consumer textiles. When we say reuse, it’s useful I think just to kind of conceptualize what that really means. And I mean the stats I’ve seen, something like 70% of the world uses secondhand clothing. Something that probably includes US consumers that buy from thrift. But dozens of countries, it’s the main item that they buy. When people are living on a few dollars a day, it’s really the only affordable option. So that’s something in the profile of that in the book. The different benefits of our industry, again that no one really notices or sees much, is the environmental benefit which we can get into that. All the water and greenhouse gases it takes to create new garments. The charitable benefit. So you don’t even know how many billions of dollars go to Goodwill, Salvation Army, powering huge amounts of workforce training and other services like that.

Marisa Adler

And even the for-profit sector often has a charitable aspect to it.

Brian London

Sure, yeah.

Marisa Adler

Just wanted to mention that.

Brian London

Yeah, we’ll get back to that in a second because the collection part is a huge question too. But yeah, the third big benefit is that it provides affordable clothing to folks that otherwise really would have no option. So you see that every time. And we can get into this too about some of the barriers to trade a lot of times. But you’ll see every time they try to impose a ban or a restriction on used clothing in these countries, the people get up in arms because it’s such a hotly desired product. And sometimes there’s different forces at play, but it’s all around the world, it’s a hotly desired—

Eric Stubin

I’ve always looked at it in the following way in that demand always told the overwhelming story. I mean, demand for these secondhand products is global. And like you alluded to, Brian, two-thirds, I believe, of Africa lives on less than $2 a day. So you could really see, especially when you travel there and not for safari, but when you really travel and you walk in where people live and you see just how ubiquitous secondhand really is, it really gives you a distinct impression and you see the demand. And it’s not only Africa, I mean, it’s across the Americas, it’s throughout the world. And it’s also interesting to point out that today in the United States, this is the moment for secondhand really since COVID. But thrift and vintage almost have never been hotter.

So I feel like there’s a lot—yeah, demand is just global and as well as in the United States today, I mean it’s really all-time fever pitch for secondhand clothing.

Brian London

It’s been a funny thing too in that between COVID and all the different changes, societal changes, secondhand has really maintained its physical presence. It’s like a lot of businesses will get pushed out by an Amazon where you can easily order something. And there are efforts online to have thrift online. We have ThredUp and companies like Fleek, SMART members, thank you, that are working to make it more online. But it really is largely still an in-person experience. So a lot of the in-person shopping is thrift because there’s something unique about those items. So there’s something nice about that whole process. So yeah, for that reason and probably a lot of other reasons of authenticity and getting unique items in a world where fast fashion blows through.

Nick Tawil

For thrift and vintage, has there been a change? So it’s as hot as ever, but has there also been a change in where it’s happening? When you think of high-end vintage, you think of metropolitan areas like New York or Paris or London or LA. And I know Japan has a big Americana vintage market, but is this happening in other places as it continues to be a steadfast thing that consumers want or grow?

Eric Stubin

My sense is that there is large global demand for American vintage. I mean, Americana, American fashion is a big part of global fashion today. And it continues to be a lot of demand throughout the world for American vintage. Vintage, the term vintage has changed a lot over the last decade. Vintage typically sometimes means, what does vintage mean? Yeah, vintage. I mean, I think in the past, well, when I first started in this industry in the ‘90s, it meant ‘40s and ‘50s and sometimes even ‘60s as a decade in terms of what you were looking for. But obviously as time advances, that changes. Now ‘90s is popular and different fashion styles and what the vintage crowd is looking for, whether it’s flare leg, skinny leg jeans, that changes of course annually.

Nick Tawil

So as you’re sorting the stuff, you kind of have to be up on this.

Eric Stubin

Yeah, I mean for the companies that sell it and deal in those markets, they have to be very aware of what they’re selling and what they’re collecting or they’re not going to find it. But yeah, the world is always looking for American vintage and there seems to be continual demand for this, although that changes what constitutes it.

Nick Tawil

What are the—I want to stay on this a little longer. What are the taste preferences for secondhand clothing that’s being sold in vintage thrift shops maybe in the United States versus what Latin America or Africans prefer or Eastern European countries prefer if the secondhand donations make it that way. Are there taste preferences across geographies?

Eric Stubin

I mean my sense is there’s a difference in the post-consumer or the old clothes that you’ll find in Europe are slightly different from that found in the United States. It has a little bit to do with the styling of each market. I’ve heard people in our industry say that the market for T-shirts or what we call the industry jargon is polo. The market for polos or T-shirts is a bit different from Europe compared to the United States. Northern Europe, the climate’s a bit cooler, so there’s more heavies or heavyweight winter, fall type clothing sold in those markets. So you get a little bit more of that in the post-consumer textile waste.

Of course, if you’re shopping for vintage clothing and you happen to live in the north of Europe, you might look for warmer clothes, you’re looking for sweaters, things of that nature. So it really has a lot to do with the markets that these shoppers are in. But yeah, there’s definitely differences between the major markets that supply secondhand clothing because fashion is slightly different all over the world.

Marisa Adler

That’s why sorting gets really complicated sometimes. But it’s also why there’s a home for almost everything that is in a bale, basically. But there’s cultural preferences in different end markets. There’s climatic differences, there’s trends that the industry always has to be on top of for when they’re sorting and grading. I think all of those things come into play. And so how a bale gets sorted and who it’s sent to is highly tailored.

Brian London

Yeah, so Eric could go through all the different items. But largely it’s a story of American soft power influence throughout the world. So in a lot of countries, I mean, I think in most markets a lot of times though, because of our, because of Hollywood, our sports stars, just like a lot of people here, they’ll be looking to have a LeBron James jersey or Jalen Brunson, go Knicks, jersey. Because American culture is kind of what they’re buying also.

Nick Tawil

And at the time of this taping, the Knicks are in game two.

Brian London

Okay, yeah, good luck tonight. And so, yeah, I guess traditionally over the decades, and as America’s role in the world changes or doesn’t change, I mean, that’s been sort of a constant because obviously we’ve been a major force around the world, definitely culturally still, and I think that plays a lot into it. But each country and each region has their own, whether it’s religious, cultural, weather, climate issues, they all have their specific items that they want. And so Eric is, and he can tell more about his company that he already gave the intro. But they were the, have been the longest running sorter here in North America. So they have real expertise in terms of when you get all this stuff from anywhere.

So in our company, we have been a supplier of his for a long time. We’ll send him items from anywhere, from Virginia or Connecticut or wherever. And then whatever it is, he’ll figure out how to get the most value out of it. So his team there will identify, because to make this work with the margins that are so small in our industry, it’s really, it’s a penny business, really. To make it, it’s a huge volume as we talked about. But if you’re not really on top of it and not finding each item its correct home, you’re not going to last. So that’s really the trick and the art of it. And it takes a lot of expertise and I don’t know, maybe Eric, you could speak more.

Nick Tawil

Let me visualize the sorting process. Who’s doing it? Where are they doing it?

Eric Stubin

So the sorting process and probably the best way to explain it is it’s not that different than most recycling businesses. It’s high volume, thin margin as a business. And we as a textile recycler are a little bit different than most conventional recycling because in conventional recycling they might make eight or nine different products. For example, if you’re collecting metals, there’s probably roughly half a dozen to a dozen different metals. Same with paper. But in the textile recycling business, we make 300 SKUs or 300 different products. So we used to like to say that this is not just a MRF, material recycling facility, but a super MRF facility because we’re making 300 of these different products.

And yeah, we outlined earlier the different percentages of secondhand clothing that we might sell to developing countries, wiping and fiber. So within each of those categories, we’re making hundreds of products for export or for consumption. And we’re not physically changing the form of those garments, but we’re wholesaling it to those that do. For example, we’ll wholesale it to a wiper company that might specialize in cutting wipers. And whether that company, previously a lot of those companies were in the US, today they’re more often overseas. Same in the fiber industry as well.

Nick Tawil

You receive these by the truckload or by container?

Eric Stubin

Yes.

Nick Tawil

And how fast can you sort a container?

Eric Stubin

Everything is about scale in our world. Our company was recycling about a trailer load a day up until 2019 and prior to that closer to two trailers a day. So yeah, I mean everything’s down. We were a mid-sized player in this industry. There are companies globally that do many times that volume and really scale is the key there.

Nick Tawil

How many people?

Eric Stubin

In the states we’re 45 people. And internationally labor is a very key component. Labor drives the whole industry. It’s very labor intensive and there’s usually a stat that one employee can handle about a ton or half a ton rather of post-consumer textiles a day or about half a ton can be sorted per employee per day. And that’s generally a pretty good metric in which you can judge the efficiency of a recycler.

Brian London

Yeah it is a fascinating thing to see a trained sorting employee. They’re making dozens of decisions a minute. That’s the only way to make it work. And it is an interesting—and maybe Marisa can talk a little bit more about the technology piece, but it’s really because of all these industries. You look around at any industry between now and 50 years ago and most are totally different. Ours, a lot of it still, because it’s a human touch. I don’t quite even really understand why it hasn’t been more mechanized. I mean, there’s different equipment that could move goods in different ways.

And with all the talk about how does AI affect this or AI affect that, to date, as far as I know from everything I see, most of the sorting of this stuff, whether it’s here or in Karachi or Dubai or Honduras, it’s all kind of the same process. And I bring up Marisa because she’s been an invaluable addition to SMART. So she came on our board, I don’t know, five or six years ago, not from this traditional background. So Eric and my families have been in this for many decades. And Marisa, I guess you’ll go through her history and background, but comes from a different perspective and came to this through a different path. And she really has her thumb on the pulse of all the, a lot of new stuff in the industry that’s looking at whether it’s—well, maybe you could talk more about it.

But anyway, that’s why she’s been a really important addition to SMART because there’s this whole new world which we can talk more about at length if we want, but that looks at the technology side in different areas. And so that’s kind of the question. It’s like, what role does that play? Does it add on and enhance our existing infrastructure that works quite well for what it does, but for the new challenges of today. So I don’t know if you want to talk about a little bit about your background.

Nick Tawil

Yeah. Because when I hear there are identical systems across different geographies around the world, and it’s been being done the same way for a very long time, and there’s volume involved, I think, well, there’s probably room to have so many types of improvements. Just like people often say AI, but computer vision specifically, it feels like it can be a boon for this type of work and not necessarily to replace a sorter, but maybe you said one sorter does about half a ton.

Eric Stubin

Half a ton, yeah.

Nick Tawil

Half a ton, what if they can now with the assistance of some sort of computer vision, they can scale that to 2 tons or 5 tons.

Marisa Adler

And there are technologies that are in developmental stages to support with that. There’s different levels of technology and automated scanning. One that’s the furthest along is to identify fiber composition. And the intent of that is to speed up the sorting of textiles into different bales. Like is it 100% polyester, is it 100% cotton, is it a 50-50 blend? And then those bales of, and let me be clear, non-rewearable textiles. Because we always want to follow the waste hierarchy. My background is in municipal solid waste management. So that’s sort of the lens that I come to this area from. You want to follow the waste hierarchy, do reduction, reuse, repurposing, and then recycling.

So the technology used, the most developed furthest along technology now is near-infrared sensing. That has been used in traditional material recovery facilities and plastics and paper and packaging for many years. It’s being honed for textiles. So you could sort polyester bale, cotton bale, and then those would theoretically go off to a recycler who would recycle each of those fiber bales into whatever products they create. And that hasn’t really developed yet because we’ve gotten a bit of a chicken or egg situation here because those recyclers are very new chemical recycling technologies and they haven’t really commercialized yet. So there’s a bit of a mismatch on supply and demand there and sort of the collaborative market build.

And then on the sorting for reuse side, you have some of the new computer vision and hyperspectral cameras that are being used paired with algorithms and AI learning systems that can start to identify, this is a shirt or this is a pair of pants or something. And on top of that say, oh, there’s a flaw here, there’s a stain here, there’s a rip here, but it still has to be paired with the mechanical movement of the item because you kind of need a 360-degree view and even more than that, maybe even an inside-out view of each garment one by one. And so at that point you need a person anyway to do that. And until robotics are advanced enough where they can do that, and we’re nowhere near that.

So even if the AI algorithms and the hyperspectral cameras are ready and they’re being developed, you still need to pair it with the mechanical functioning of a facility. And so I think that’s the stage that we’re at now. There’s a lot of pilots going on, there’s a lot of development, there’s a lot of investment in that area. And I do think that’s the future. We’re just not quite there yet.

Brian London

It really is a pivotal moment from our industry standpoint, from an industry association, because traditionally, something unique about our industry is that we move an enormous amount of volume all over the world. All these numbers that we’re talking about. But traditionally we’ve always been a group of small family businesses, like Eric’s family, my family, and hundreds of others. And what we found recently because of, I guess because of increased attention for whatever reason, now all of a sudden we have huge brands coming in and getting involved, and they’re throwing huge amounts of investment in things. And then you have policymakers. And we can talk about the legislation that passed in California. They’re looking at, in New York and Washington state, essentially legislating how textiles are collected and handled, post-consumer textiles.

So all of a sudden you have these small companies that as a force we do, I mean, as a group of companies, as a trade association, we do a pretty good job of, I think, punching above our weight in terms of advocating for our members and open trade for our product. But all of a sudden there’s these enormous players involved. And a fear we have sometimes is, number one, how do we incorporate that without destroying part of what’s already working? And how do we get our voice heard? When you have these, a lot of times I’ll hear a policy coming in some country somewhere or a big effort made by a huge investment in a certain recycling technology. And it seems like they hadn’t even really consulted this group of companies that’s processing all this material.

So that’s kind of a big question right now is how do we work all together?

Eric Stubin

How does private sector work together? How do all the pieces come together? How does private sector work with all the other stakeholders, including charities, including innovative partners, to really grow the pie for everyone? And just to put another, underline Brian’s point, my back of the envelope calculation, there’s about 10 billion pounds that the traditional reuse markets have handled globally for decades. We get that number, if you look at the US, that number that I believe is correct, if we had the EPA website here, I think it says about 3.8. There’s about somewhat of an equal number in the EU. And then I pencil in Asia, including Japan, Australia, and then China has its own industry.

And I haven’t seen too many stats at what China’s generating in terms of post-consumer textiles. But it’s a tremendous number that the industry has efficiently found a second life for decades. So I think there’s a lot of innovation coming and we’ve got to find new ways to do it. And the innovation will always be there and markets are willing and able to, we as an industry will be there to support them. But yeah, this is the challenge that we face.

Marisa Adler

I think building on what Eric said, the United States has the highest per capita textile waste generation rate in the world. I think China is bigger on just a mass absolute value amount. And what’s important to recognize though is that we’re still only recovering 15% in the United States of what gets generated as textile waste every year. The 85% we’re not collecting is going straight to landfill and incineration. And so there’s a huge opportunity to recover those materials and find new homes for them, whether that’s in reuse or through repurposing or recycling. And that’s what a lot of the new policy that Brian was talking about is getting at. It’s mostly sort of this, it comes from the waste management perspective, extended producer responsibility. How do we get to zero waste and how do we incentivize that the right way?

And the idea of extended producer responsibility is putting the financial onus back on the original producer. Because then as theory goes, they would design products to be better reused or better recycled at end of life, or maybe they’ll reduce how much they produce in the first place.

Eric Stubin

Yeah. To underline Marisa’s point, one really interesting fact is that, and this fact, this stat is very universal. I think you’ve heard this. When municipalities look at the percentage of, when they analyze their waste streams and they look at the percentages of municipal solid waste, they almost universally find or have found that it’s about 5% composed of old clothes or secondhand clothing. That’s why states like Massachusetts, I think, went into, they technically, they put a ban of secondhand in their legislation, and you’re not allowed to throw away clothing in the state of Massachusetts. But yeah, I mean, that’s a great segue to EPR in California and why they’ve done this.

Brian London

Yeah, do you want to explain more about what happened in California?

Marisa Adler

And so California was the first state in the United States to pass extended producer responsibility legislation for textiles governing the textile waste stream. The way I just described, the producers have to pay usually a per unit fee into a centralized organization called a producer responsibility organization.

Nick Tawil

Who’s that owned by?

Marisa Adler

It’s usually stipulated as a nonprofit. And the whole purpose of that nonprofit is to fiscally manage the recovery system and issue the contract. And usually the board of directors is brands who are producers of the textiles and apparel, the covered products. And they have to answer to the state agency. So there’s always an oversight agency. In California, it’s CalRecycle, which is a part of the Cal EPA organization. And so once the law is passed, then CalRecycle will develop regulations which just additional clarity onto the law, maybe put in some performance standards on how the program needs to operate or what metrics it needs to hit.

But then other than that, the PRO is the one sort of looking at the system, figuring out how it’s going to develop a program to comply with what’s in statute or what’s in the regs, and then a board of directors that kind of oversees that, and then they get the funding from the brands. And so the brands are paying either per piece or per kilogram. It’s different in different places. So California was the first state in the US to pass that law, I think, in the very end of 2024. End of ‘24.

Eric Stubin

Yeah, that’s what I remember.

Marisa Adler

It’s a very long time frame. So it actually won’t be implemented fully. The residents of California won’t see the effects of this until about 2030. And producers won’t pay into it because there’s a lot of—

Eric Stubin

They’re still designing the regulations around it.

Marisa Adler

Yes. The regulatory development process is a couple of years. The program plan is a couple of years, fee setting, all of that. But this is a model that’s been around for many years.

Nick Tawil

Where else in the world has this been around?

Marisa Adler

Europe. The EU has mandated their member states to all adopt EPR and they actually do have a disposal ban across all member states that started January 1st of 2025. And the way that the EU is instructing its member states to comply with that ban is by adopting EPR regulations. Because the last thing you want to do is implement a ban without a plan because then you have a lot of textiles that are no longer going to landfill but have no infrastructure or funding or system to support it. So the point of EPR is to create that.

Eric Stubin

And Marisa, France had the longest running program. And I think the website that you mentioned earlier was Eco TLC dot fr but I think it’s taken on a new…

Marisa Adler

Refashion.

Eric Stubin

Refashion. Yeah. So that program was very innovative as Marisa pointed out, because it was one of the first essentially to tack on a fee for the recycling of every garment is my understanding of it. It’s a few euro cents. I think it’s more than, between, I want to say off the top of my head, between 5 and 10 euro cents per garment that’s charged to the consumer. The PRO or that group, the name of the group again was…

Marisa Adler

Refashion.

Refashion collects that money and distributes it to French or companies that recycle French post-consumer textile waste.

Eric Stubin

So California, Washington, states that are looking at EPR have a model in which to look at. And it’s also interesting to me that all of the stakeholders are part of that model or part of the solution. Because if you think about these are huge macro issues and how could one stakeholder tackle any or just all of it. You really need all the stakeholders working together in concert to help alleviate or move the needle on the issue of post-consumer textile waste.

Brian London

So with all those years of that program, it’s been like 10 years, I guess France has been doing it or more.

Eric Stubin

I think so, yeah.

Nick Tawil

Have there been any definable outcomes from it?

Marisa Adler

The French EPR system is, it hasn’t been modeled as a true EPR system in the sense that traditional kind of purists of EPR think of EPR. So it hasn’t done a lot to change the upstream design and production of textiles. A lot of factors that go behind that, including how much the fees are and incentive and is this just the cost of doing business or what are the penalties? Things like that. But if you look at EPR across different product categories over, I don’t know, the last 20 years in the United States, if it’s well-designed EPR, it has a very clear beneficial impact on the recovery rates of those items and on the design of the products going into the system. Because there’s a very direct financial link right back to the producer.

It gets really complicated in terms of how you structure that mechanism. And it gets really complicated because there’s a ton of stakeholders with varying—I mean this is policy. This is how policy is developed. You’re always going to, you’re never going to have the perfect bill, you’re never going to have the perfect worded law. But it’s really important to have well-designed policy. And EPR is not a magic bullet, but it has an opportunity to really infuse some capital, infuse some funding and think holistically about a system.

Nick Tawil

And can you just differentiate the difference between EPR and maybe we can start talking about something else which is closed loop.

Eric Stubin

But just before we go into that, I mean it’s also interesting to note that Europe diverts about 2x the volume of post-consumer textile waste than we do. They divert it at a higher rate. I think that’s what most of the EU studies show. So they divert a similar amount and it’s more per capita of textiles. So their diversion rate’s higher.

Brian London

Yeah. Which means they’re capturing more.

Eric Stubin

They’re capturing—

Brian London

So less is being thrown out. A lot less.

Nick Tawil

Oh, got it.

Eric Stubin

It goes to the old, everyone knows, I mean Europe politically and from a cultural perspective has always been ahead of the curve in terms of recycling. So they’ve done a much better job at keeping old clothes out of their landfills in general. And the EPR is sort of building on that.

Brian London

Yeah, but so you’re asking about.

Nick Tawil

Does it make sense to talk about closed loop now? Or, I kind of want to, going back to the thrift and the secondhand use. So highest use value concept. We can tie this into maybe earlier in the conversation. But any insights that you guys have taken away from the habits of American consumerism. Seeing all this stuff, seeing so much of it come over the transom over so many years and just be like, what are your thoughts on that? Either what do you think about American consumers specifically? I mean the trend is, I mean the habit is huge. But yeah, you kind of sigh.

Marisa Adler

Pass… No, I’m kidding.

Nick Tawil

Yeah, I don’t know. Or maybe not. Maybe you just, you see these truckloads of clothes come through and you’re like, yeah, just—

Marisa Adler

Well, it’s a river. I mean, I’ve always heard Goodwill describe it that way. It’s a river. They cannot block the river. Any blockage will just create overflows and chaos. I want to say that, but I also want to say we’re still only capturing 15% so don’t hear that and not, you know, divert your textiles and meaning, you know, donate or recycle. But we today are consuming massively more textiles per capita per time period than we ever have in the past. I mean if you look at the consumption graph, it’s almost like an exponential graph. And that’s because of the advancements in just-in-time production and fast fashion and drop shipping, which basically means door-to-door shipping and taking advantage of direct shipments from the manufacturer piece by piece, straight to someone’s doorstep.

And of course all the online e-commerce platforms that we all have access to. And then because it’s so readily available, they can make trends and the trends have just gotten more and more intense and quicker and quicker. We used to have seasonal trends like four a year. Right now it’s like one a week. And so people, especially with social media, can’t be seen wearing the same thing twice on their TikTok or Instagram or anything. And so there is definitely a hyper-consumption mindset of American consumers and the price has dropped because of fast fashion and a lot of other factors. And so it’s more accessible but people are keeping things like half as long, wearing things half as long. And so it’s just way more volume, way more turnover, but way less quality.

And so it has a much lower value and—

Eric Stubin

We’ll get more rags and material for fiber than we will usable clothing. But that was well said. I think that fast fashion is a major contributor, mass market apparel, and that’s the way the industry goes. And as the industry drifts towards that and there’s more consumption of this, of course, the quality of America’s secondhand clothing generally goes down and it’s harder to find durable, longer lasting garments in the post-consumer textile waste stream. But yeah, you can never turn it off. You can’t turn it off. It’s going to consistently flow and that’s why all the stakeholders are constantly trying to look at these issues together.

Marisa Adler

Yeah, yeah. And one of the concerns is with textile EPR legislation and potential disposal bans that come with it. You’re going to start seeing the stream that people have been throwing away. And there’s more, there’s concern that some of that is reusable, high quality because some people just don’t ever donate. But the concern is that we’ll see even more of the lower quality items if we’re forcing people to not throw things away and instead donate them. And so how is that going to affect the overall economics of the system and ability to divert for reuse? It might just kind of bring down the value of the average ton.

Eric Stubin

What’s the theory? I’m sorry, Marisa, can you give it to us again one more time? The idea is that they’re going to—why one more time, I’m sorry.

Marisa Adler

Because we’re going to get all the dirty socks and old underwear and things that people shouldn’t really, that, you know, maybe there’s a recycling market for it.

Nick Tawil

We should start with that. What’s appropriate to donate and what’s not appropriate to donate?

Brian London

Well, that’s been—

Eric Stubin

Yeah, that’s an interesting—

Brian London

Remember, don’t—what was the campaign?

Eric Stubin

I always would say don’t judge your clothes. Someone at SMART once said that in front of a group we were educating, I think the Northeast Recycling Coalition. And they had the term “don’t judge your clothes.” But building on that point, Marisa, I think that every statistic that I’ve seen is that there is a universe of post-consumer textile waste. And as you increase diversion, so do you increase all segments of—I don’t know that if today we are actually recycling 15% of all post-consumer, that means the remainder of post-consumer that’s going into landfill is necessarily all materials suited for landfill. People still make the mistake of throwing out—people, the average American doesn’t think of clothing as something that should be donated or recycled.

Often it’s tossed into the landfill. And there’s a lot of examples from pop culture. I keep a running tab in my mind. But it’s funny, there’s a lot of examples of that. You see it in movies, you’ll see it in books and TV shows. It’s out there. And not everyone thinks of clothing as something that you should donate or recycle.

Marisa Adler

And this is a tricky point though, because different places have different rules about what you can donate. Kind of like why it’s so complicated to just standardize recycling like your curbside recycling. Every place you go has different rules. It’s kind of like the same thing with your textiles and your clothing. Goodwill may have one set of rules. And also, mind you, not every Goodwill has the same set of rules because they’re all independently operated. But a consignment shop obviously has different rules than a donation bin. And so some places, it’s hard to put out the message, just donate it. Because some places don’t want the things that they can’t resell.

And until you have solutions like closed-loop recycling and a higher market demand for some of the fiber recycling, open-loop recycling, it does create a little bit of a drain on the system because then, folks like Brian and Eric could be inundated with a lot of really low value things. I mean, I don’t want to speak for you guys, but just thinking sort of conceptually, what would happen if you turned on that spigot?

Brian London

Yeah. Well, that also brings up the question of just this great unknown and the role, or maybe I would say the lack of data pretty much to date for most of our history of our industry. Every company’s doing their thing, they’re getting stuff in and there haven’t really been great numbers. Number one on, so how much is coming in from where, how much is being generated? If you actually dig into—so we quote this, only 15% of all clothing that’s discarded enters our stream. And that’s an EPA stat. And so I know Marisa and I have talked about this before, I still don’t quite understand. You go and you’re like, well, okay, how’d you figure that out? What are the methods behind it? And it’s kind of opaque.

Maybe you’ve done more research since we last spoke about it, but it’s like we don’t really know. So we don’t know how much and we don’t really know what’s out there in this world. So that calculation came from somewhere. And even if it’s half true, it’s still an enormous amount. But we don’t know that. And there’s a lot of things we just don’t know. But we’re starting to look at and Marisa lives in this world a lot in terms of data because you can’t really do much if you don’t really know the volumes coming in, what they’re, how much it’s going, what are the compositions in end markets. And so we’ve started trying to do a little more data. There’s different groups out there looking at some and we’re starting to get into that world.

Nick Tawil

Is it easier to do that here domestically or overseas?

Eric Stubin

There’s data that’s out there that the government, the US government has measured. I mean, they have the USITC. I have that acronym, United States Trade—I forgot. I hope I have that right. USITC trade data. And that measures the volume of containers that are being exported out of the United States. I mean, I think that was one of the key variables that they used in some of that, in some of the EPA’s construction of that, those data points.

Marisa Adler

I think it depends on which data you’re looking for. If you’re looking at understanding textile waste generation rates and the composition of the textile waste stream, then doing it in the United States makes sense. If you’re looking at traceability and understanding what fraction goes where, that gets really hard really fast because you can put an RFID tag on a bale that’s getting exported, but that bale will land at the first port, maybe in a Karachi export processing zone, for example, in Pakistan, which is one of the world hubs for sorting and grading. And then that bale gets opened and torn apart. That RFID tracker is no longer useful. Each piece in that bale then gets sorted and graded and mixed with materials from the UK or other places in the EU or any other place they’ve imported from.

And then it’ll go off to the first importing market, maybe it’s Kenya. And then the importer imports that bale. Then it gets opened up, resorted, redistributed through sort of a whole chain of market players all the way down to a stall owner in a secondhand market and whatever—

Brian London

Even in neighboring countries.

Marisa Adler

And then if it doesn’t sell there, then it might get rebaled, like aggregated and rebaled and then redistributed or even just directly exported to neighboring countries. It gets really hard to start tracking where everything’s going. Yeah, and so the data and the transparency piece is a really big underpinning of the new, all the new legislation we’re seeing. Even it’s fueling, I think, a lot of conversations at the international trade level. When you’re looking at the UN and the Basel Convention on how do you track and manage, again, I’m going to use a loaded word, textile waste. It’s a commodity. We don’t like to think of it as waste because people affiliate waste with garbage. But understanding where all that data sits and who holds all that, it’s a very decentralized system of who knows what.

And there’s no mandatory or very little mandatory reporting. There’s really not anyone aggregating this on a systems level to be able to understand.

Eric Stubin

There is some data that’s collected or aggregated from, as you mentioned, from a trade perspective and from the volume perspective that could be in orders of magnitude. Give us a sense, from a value standpoint, it might be different, but from orders of magnitude, are there hundreds of millions or how many tons are being exported to various processing centers from the United States? That information could be fairly accurate. And then the other interesting point Marisa brings up is, well, when you look at the term textile waste, it’s hard as someone that processed probably a billion pounds in their career of textiles, when you look at it, the demand tells a story because it’s finished product. So a lot of what’s being called waste—and there is someone prominent in our industry that just wrote a piece on this and says, what’s being called waste could be, they could be terming it waste because of the nature that X percent sold in a market and then X percent had to be wholesaled.

But I can assure you that the industry wouldn’t be able to sell and wholesale billions of pounds annually if this material wasn’t graded in a suitable way that then resulted in markets demanding it. And that’s really, I think, tells volumes about the products that we ship as an industry. Because it has to be right. It has to be graded to a certain extent for the quality. People are often surprised that secondhand clothing is not tattered or torn in most countries, that it’s good, usable clothing that has a second life. A garment that may have been sold for anywhere from $40 to $80 retail will find its way to a developing country and in that market be sold for maybe a dollar. So something affordable. And it gives the consumer in that country a lot of dignity and choice in being able to shop for secondhand products or for products that are unique.

Brian London

Yeah. And for us, the economics really tell the tale, largely because I’m going to say in a free market. But it’s actually even more than that because we’re overcoming enormous tariffs and taxes on—

Nick Tawil

Yeah I was going to go there. There because you mentioned demand, but the demand, the countries with the demand don’t necessarily get the secondhand use donations, right, so what are the forces that are going against that?

Brian London

So, yeah, I mean, traditionally there’s been some elements of protectionism which probably come from a good place. But I think miss some of the economic realities that again in most of Africa where people are living on less than $2 a day, I forget the statistics, but it’s like a used item is maybe 95% cheaper than a new item that could be created in that market. And let’s say in Kenya, in my mind it’s a bit misguided policy and at our trade organization we’re always working to open markets and lower trade barriers to our product. But it’s desired everywhere and so much so that even with, for example, we’re just working in Costa Rica because the duty there is about 50%. Effectively they have, they tack on all these other taxes with it.

But it’s still, even beyond free trade. So the economics of it really tell the tale. But when you’re actually looking at definitions and textile waste and what does this mean, and you start having these different organizations and policymakers and governmental organizations looking at it that don’t really live the day-to-day, they could from a very good-natured place make decisions that if you miscalculate it a little bit, you could stop an entire flow of goods which again in one place are waste and another place are vibrant markets of people. You go to these places, everyone’s looking for, it’s a huge vibrant economy at these places. You go to markets in Kenya and you see enormous demand for the product.

Nick Tawil

So how big are these markets?

Brian London

Oh, I mean tens—

Nick Tawil

Like outdoor mall size markets or bigger or smaller?

Marisa Adler

I mean if you go to the Kantamanto market in Ghana, it’s huge. I mean you can walk and walk all day through all the different aisles of the stalls. That’s probably one of the biggest that exists.

Nick Tawil

All secondhand?

Marisa Adler

All secondhand. All secondhand.

Brian London

Tens of thousands of people there. Wow. But then even downstream there’s—we just did a trip to Costa Rica where, along with some folks from Goodwill, we were tracking items that we sent there. And then the second and third degrees away all have fascinating stories. It’ll go to another trader. Then it’ll go to, in Costa Rica we profiled this one charity that she funds for young women who are victims of incest. The whole charity is funded by items that she finds good deals with. And so you follow all these items even second, third degree away from that, there’s economies that are also hard to track.

Eric Stubin

A lot of ancillary business activity generated from secondhand that some studies I think have tried to measure. There was a UN study a long time ago that tried to measure the ancillary industries that were generated by secondhand trade. Everything from moving secondhand products to tailoring them in these markets. And then, I think more and more you’re seeing that there’s some vertical in the, within these countries that import the materials and maybe they’re even cutting rags or they’re trying to incorporate other aspects of secondhand clothing. But yeah, it’s a tremendous industry. Rivoli’s book says that it’s one of the most competitive industries that she had ever studied. It was secondhand industries just with sheer volume of competition and truly competitive industry.

I think at the end of the day you really wonder, if you support free and open markets, it’s something that’s important. And secondhand clothing certainly fits in, it fits into that description. Most of the times where we’ve, the industry has seen problems, a lot of the bans seem to be, like Brian pointed out, a lot to do with protectionism. And it’s not that different here. There’s different industries that are affected by protectionist viewpoints here in the United States. But that seems to be a major factor across the world as secondhand competes with cheap manufactured apparel from other countries that are manufacturing.

Brian London

Yeah, I just want to circle back to the question about closed loop. So this whole world, and this has been a pretty new world for us. Again, this is kind of more the world that Marisa lives in day-to-day. So we’re talking before about closed loop. There’s—I mentioned there’s enormous amount of investments from brands, from other investment companies. And I was thinking to myself, why did all this money get into this closed loop? So by closed loop, we mean actually taking a shirt, not just reusing it, extending its life or repurposing it, but the actual process of turning an old shirt into a new shirt, which is way more complicated than you think for a lot of reasons. We could probably spend a whole hour or a whole semester talking about.

But so yeah, this whole world of closed-loop fiber-to-fiber technologies has become a big, I mean you go to whole huge conferences of it. And I couldn’t even put a price tag on the amount that’s invested in it. But to date, Eric had a good visual he did with the Venn diagram before about it’s really moving very little in terms of the practical economy so far. So there’s this huge amount of potential that we see. But I’m trying to think of myself too, what prompted all that? Is it that we feel like we’re not capturing stuff in that 85% we assume is all low-end, unusable stuff, that if it entered, because it is true, let’s assume 85% were low-end stuff and we all loaded it to our graders, we would have an issue.

Eric Stubin

I don’t think that’s ever been the case because we have increased—and if you look at, there is a model that’s out there. If you look at the EU versus the United States, the EU diverts 2x the amount of post-consumer that we do here in the States. But their post-consumer does not veer towards only unusable clothing or material that would only be destined for the fiber industry. So I think there’s, as you increase the pie, you get all segments of textiles. All segments of textiles increase along with it.

Marisa Adler

I think the push towards this closed-loop recycling comes from a sustainable materials management perspective of our Earth’s natural finite resources. And at true end of life, like once reuse is no longer an option and everything will eventually get there, how do we keep those materials in circulation? How do we maintain the value and how do we use those to displace the production of new materials? I think that’s sort of the age of where we’re at right now in the textile waste management industry is looking at how do you create those infinite loops and keep materials in circulation forever? And the answer cannot be found in reuse. Eventually it’ll reach end of life.

It can’t be found in mechanical recycling because of the technological limitations of mechanical recycling and the degradation of the natural fibers and what those fibers can be used for. So new emerging recycling processes are what we’re turning to, including things like solvolysis and depolymerization and some of the categories of recycling that are deemed chemical recycling, which is a kind of unfortunate umbrella term because it creates a lot of confusion over what they actually are. And there’s sort of a lot of stigma around, oh, chemicals, hazardous, bad. But I think that’s where this new age approach is coming from.

Eric Stubin

It’s a worthwhile goal. I mean it represents innovation and where the industry and all the stakeholders hopefully will come together to work in it. I think that’s some of what’s happened in various states that are trying to introduce EPR legislation. It almost feels like the legislation was written with a futurist world in mind. And then when the real world markets and innovation catches up to some of this regulations then I think it can all potentially work in harmony. But it might be a little ways till we’re there.

Brian London

But when you look at the economics of it and you see kind of what, prices would be for a material here. So let’s say you got a bunch of low-end stuff you can’t reuse, you can’t repurpose. You can talk a little bit about what we see or hearing about the cost of what’s—there’s interesting technologies that can sort these into the specific fiber types that could in theory and practice on some level turn them into feedstock. But the economics of it, from your perspective, someone handling the material, how do you view that? And what would make that fit into your worldview?

Eric Stubin

I mean it’s hard and I don’t, I think most of the professionals inside the industry, when they talk about it, we all sort of scratch our head and we wonder about the economics and how they might come into play. It’s hard to see today but markets change and so does technology. And when, I’ve always said when markets are willing and able to, the industry will likely find a way to support them. But at the moment it’s tough to find that. Even from, I’ve heard things by, from closed-loop recyclers, they said there’s X percentage of 100% cotton waste or X percentage of poly waste and some of that material is hard to find.

And it certainly seems when you hear apparel talk about, they need design to marry up with the overall strategic plan to recycle more waste. And there’s a little bit of a dichotomy there between design sometimes and recycling. So we need, there’s got to be a holistic move to make the, to make all of the variables come together and get everything moving in the same direction.

Marisa Adler

Yeah, I’ve done some financial modeling on this new textile recycling system and everything has to be exactly perfect for the model not to break and even then, it’s kind of shaky.

Nick Tawil

Well, I knew there’d be way more to talk about than the time we had allotted. Eric, Marisa, Brian, thank you. As is the tradition on the Infinite Loops episodes, there’s a final question. And so it’s a bit of a curveball, but here we go. If we’re going to make you the king or queen of the world for the day, and you can’t kill anyone, and you can’t put anyone in a re-education camp, we’re going to hand you a magical microphone. And you’re going to say two things into that microphone that will incept all 8 billion plus humans on the Earth. And when they wake up the next morning, they’re going to be like, oh, here’s just something I thought of. What would those two things be?

Brian London

Wait, so I’m giving a message to everyone in the world?

Nick Tawil

Yeah. And when you incept them with these two ideas, they will actually go out and do it.

Marisa Adler

Right. So you’re brainwashing.

Eric Stubin

All right, I’m going to go first. Mine is donate, recycle, don’t throw away. Does that count as—that’s three words. Is that one?

Nick Tawil

I’ll allow it. I’ll allow it.

Eric Stubin

Is that what you’re allowing for? You’re looking for two thoughts or two—

Nick Tawil

Two ideas.

Eric Stubin

Two ideas. Donate, recycle, don’t throw away, and don’t judge your clothing. That would be—

Nick Tawil

But also, don’t donate dirty socks.

Eric Stubin

You can donate dirty socks. We’ll find a home for—

Nick Tawil

Ah okay!

Eric Stubin

You can donate dirty socks.

Nick Tawil

Marisa.

Marisa Adler

It probably wouldn’t even be related to textiles.

Nick Tawil

It doesn’t have to be! It doesn’t have to be related to textiles.

Marisa Adler

All right, cool.

Nick Tawil

It can be love thy neighbor. It can be anything you like.

Marisa Adler

I think that’s what it would be. Recognize the reality that life is fleeting, life is short, and so just approach every day like it could be your last. And the second one, I think, would probably be something around love thy neighbor. Treat others as you’d like to be treated. How are you feeling about yours now?

Eric Stubin

About the dirty socks?

Marisa Adler

Exactly.

Nick Tawil

That’s great. That’s great.

Marisa Adler

Go ahead Brian.

Nick Tawil

We need variety. So this is good.

Brian London

Tune in, Infinite Loops podcast.

Nick Tawil

Wow.

Brian London

I guess, kind of like what I was thinking about earlier with shirts, like, whether it’s this industry or anything. Take a look at things sometimes and just kind of ask yourself, what’s the story behind that? How did that get to where it is, where’s it going to go? Dig into kind of what’s the story behind things? Because a lot of times there’s something interesting, and we tend to just kind of, when you see something every day it kind of just becomes like white noise. But there’s a lot of interesting stories around, and I hope we’re one of them. But you guys decide. Maybe we’ll see you chapter two in a few months.

Marisa Adler

Actually yeah. Think critically and act with intention, I think.

Nick Tawil

There you go. Okay.

Brian London

I’ll take that, too.

Leave a comment

Subscribe now

Share

This was such a fun conversation. I’ve shared some highlights below, together with links & a full transcript. As always, if you like what you hear/read, please leave a comment or drop us a review on your provider of choice.

— Jim

Links

Apple Podcasts

Highlights

What would you do if you knew you would fail?

Jason Buck: And with insatiable curiosity, and I know this is what we were kind of getting at earlier about portfolios, it’s extremely personal to us. It’s praxis, right? This is my entire life philosophy that I’m putting into this business and this portfolio for you. So it’s deeply personal. And so to me, it was more of that alignment where maybe in my younger years and maybe living under what’s important to others or some sort of Girardian mimesis, where it got to the point of, this aligns with my values and who I am at this point, and this is deep practice for me. So this is all I want to do. If it works, if it doesn’t. But this is what I want to do.

I always, I joke with our mutual friend Senra about there’s that quote was like, what would you do if you knew you couldn’t fail? And I’m like, fuck that quote. It’s like to me it’s, what would you do if you knew you would fail? That’s what we’re compelled to do.

Jim O’Shaughnessy: That’s a much better question.

Jason Buck: Just run headfirst into walls every single day knowing failure is probably imminent.

Jim O’Shaughnessy: Yes.

Jason Buck: And if we do get lucky, great. But otherwise, that’s what it’s—not anybody would do anything. Yeah. What would you do if you couldn’t fail? Anything. I’d fly out this window.

Jim O’Shaughnessy: Right, exactly.

Jason Buck: But no, we’re compelled to do things. And this gets back to where you and I disagree about free will. It’s like I’m compelled to do this thing where it’s high likelihood of failure, but I don’t know anything else better to do because it’s just everything of who I am and this amalgamation of detritus I’ve collected from others throughout these years because I don’t even have any thoughts I can call my own. They’re really other people. I guess they’ve been uniquely put together into this body and brain. But that’s all I’m doing, is using those to the fullest extent of my abilities. I’m just giving my all into this. And if it works, if it doesn’t. Because we can’t help ourselves.

Crossing the bridge of nihilism

Jason Buck: Yeah, well, as you know, he’s a mutual friend of ours and he’s 100% right. Because part of it too is a lot of people in our position want everybody else to be entrepreneurs or think the way we do. I don’t want anybody to think the way I do. And I actually think entrepreneur is a bug, not a feature. I think it’s terrible brain chemistry. Right. The way society’s set up for bimonthly paychecks, a salary, and then you get a mortgage and it all makes sense. Right. It’s bond-like income. Why do we want this equity VC-like income? There’s something wrong with us. And just I know to you and me, Hypomanic Edge was a really important book to me in my 20s.

Jim O’Shaughnessy: Yes.

Jason Buck: It made me understand myself if I have this mild bipolar. Right. Because part of that bipolar is that you get all the positive effects of really being able to lock in and focus on things and build businesses where you’re creating an entire world that you’re the fuel for that. But it also comes with a commensurate downside as well. Right. The darkness.

Jim O’Shaughnessy: Yeah, well, everything does.

Jason Buck: Right, right. It’s just not a free lunch.

Jim O’Shaughnessy: No. And when I was in my 20s, I was just staring way too long into the abyss. And as you—you know the quote, it stared right back into me. And I was like—for a while, I was just like, why bother? Nothing matters. There is no truth with a capital T. There is no such thing as enlightenment. And the way I came to kind of figure that out because that leads to nihilism. And my thought was, well, okay, let’s assume that this is mostly right, even though I think it might be mostly wrong. Let’s just assume it’s mostly right. Well, what can I do about it? And I call it walking across the bridge of nihilism.

And when you get to the other side, you’re like, okay, well if life has no meaning and there is no such thing as enlightenment and there is no truth with a capital T, that means that I get to determine meaning. That means that I get to say what matters in my life. And so once I really embraced looking at the world that way, that’s when all of the dark abyss staring stuff didn’t end, but it was just like, oh, there’s the abyss again.

Jason Buck: Okay, this is why I love talking to you. Because it gives us time to talk about, pull on strings of nuance. And so you say you’re saying nihilism and everything. And I’ve always—everybody thinks nihilism is a pejorative.

Jim O’Shaughnessy: Right.

Jason Buck: But I think what got to the point, what you said is the true, I guess, definition for nihilism is there’s no grand meaning to life. Right. But like you just said, that means we get to make up our own quotidian meanings to life.

Jim O’Shaughnessy: Exactly.

Jason Buck: So our family, our friends, whatever we’re into, drinking or eating or whatever and just sitting in the park, having an espresso, that’s the meaning of life. Having conversations like this, that’s my favorite part of life. And so that’s what I mean. So it’s like, don’t you think that’s fair? It’s like, so you can be a nihilist on a grander meaning, but that’s totally different from making individual meaning on a daily minute-to-minute basis.

Transcript

Jim O’Shaughnessy

So, Jason, welcome to Infinite Loops. I love you for a variety of reasons, but when I look at your CV, it’s like, you’re a young guy and yet your CV, I would peg you at 87.

Jason Buck

Well, one, I appreciate you saying young guy because I’m 47, so I don’t quite feel as young anymore.

Jim O’Shaughnessy

From 65, that looks young.

Jason Buck

I know it does. But you always talk about being old, right? If we ask any of these guys in their 20s, I’m a boomer too, or whatever, I’m almost dead. So I appreciate that. But I do have a chaotic or circuitous CV in the sense that maybe what I didn’t realize is maybe I was always applying to work for OSV, right? I knew only it was for an audience of one. This has been in planning for 20 plus years.

Jim O’Shaughnessy

I admire your patience and your ability to succeed at all of these various things.

Jason Buck

Well, success may be, that may be overshot. Right. I think it’s probably a lot of failure and just stumbling from one failure to the next.

Jim O’Shaughnessy

So I guess the first question that I wanted to ask was how did all of the former things that you did—I mean, you were a great athlete, you did real estate, you did religious studies. I want to talk about that because I think there’s a lot of correlation between people’s investment beliefs take on an almost liturgical ring to them.

Jason Buck

100%.

Jim O’Shaughnessy

But what did you learn from the earlier stuff that helped you with the Mutiny Fund and the Cockroach Portfolio?

Jason Buck

So I think it’s really easy to connect those dots in hindsight. Right? That’s what’s always hard for us with that foresight. The way I think about it is you and I suffer from a similar affliction of insatiable curiosity. So ever since I was a teenager, I was fascinated by religion and just why people act the way they do. And obviously religion’s a huge part of that. And my mother came from an Irish Catholic family, and my father was a Zen Buddhist. But this was in rural Michigan in the ‘80s, so that was very rare. So we started meditating at a young age due to my dad and everything. He was also a triathlete and endurance racer, so maybe that was part of it as well.

So my parents said, we’re never going to give you a religion. We’ll let you kind of choose your own. So starting at 12, 13, I started going with friends to churches, synagogues. I just wanted to explore, what is this? Why are they all so enamored or obsessed by this? And part is, with religion, it incorporates everything. So when I ended up going to university, I actually originally started international business. That was really easy because I came from a family of entrepreneurs. So I just always had the gift for business, I guess. I always go, people say they’re entrepreneurs. I’m like, what were you selling in middle school? I was selling bracelets my sister and I made. I would make mixtapes and sell them at school. You have that in you.

Jim O’Shaughnessy

Hall passes for me.

Jason Buck

Hall passes, you could sell. You found a pad you stole from the teacher.

Jim O’Shaughnessy

Of course.

Jason Buck

So perfect. It reminds me I was the worst kid in the sense that I would skip school, but I would leave during first period and I’d go to the library and I’d spend all day in the library.

Jim O’Shaughnessy

That’s not a good truancy effect.

Jason Buck

No, I should have gone to smoke cigarettes behind the local convenience store. But no, I went to the library. What I found through eventually switching to comparative religions, it incorporated everything. Because I was fascinated by history, philosophy, art, sociology. And really, that is the foundation of all of those things that come out of that is the way I thought about it. So it was a never-ending quest for that insatiable curiosity.

I also found interesting while I was studying comparative religions and I played D1 soccer at College of Charleston. Eventually I also had to get a job and I got jobs in restaurants. And eventually I leaned towards the sommelier wine side because once again, it was insatiable curiosity. So you could learn about every varietal of wine in the world. But every year a new vintage comes out and you basically have to reset that knowledge base. So once again, it was insatiable. It was the never-ending rabbit hole that I knew I could never quite satisfy.

So then after coming out of school and studying comparative religions and everything, I spent time living with a Buddhist Rinpoche. One of my mentors was a Hopi Indian shaman. I moved to Istanbul, Turkey. And everybody’s maybe heard the story where I sold Turkish rugs on the streets of Istanbul. “Hello, my friend. Would you like a cup of tea?” That was me. And this is in the late ‘90s, the first time I went there twice. And it was always interesting to me because all these Americans coming off of cruise ships or whatever, if they saw a blonde Midwestern white kid, they immediately trusted me versus a local, which they shouldn’t have. I mean, I always took care of them. But you’d sell them a Turkish rug and they’d be like, I want a leather jacket. It’s like, great. I know a Russian guy that makes leather jackets. I need a good restaurant. I go, great, take them to a restaurant. You circle around the block, you come back, and the restaurant owner gives you [inaudible]. I like the way that economy worked, I’ll put it that way.

But I was really doing, when I was in Istanbul, I was actually also living with the Mevlevis. So the Mevlevis are a sect of Islam that comes out of the—colloquially known as the whirling dervishes. So they trace their lineage back to Rumi, but once again, it’s the esoteric version of Islam. And so I was studying with some of the sheikhs there, and that’s why I was living in Istanbul.

And eventually, we talked about this before when I was at your house, eventually you get to the point where no matter if it’s Buddhism, whether it’s the Mevlevis, whether it’s any sort of shamanic tradition, they think they have secret knowledge. And so it got to the point always where I was like, show and tell time. Put it on the table, what do you have? And of course, they never had anything, right? It was always in the future. It was always pushing those goalposts away, always. And so eventually, I just kind of gave up on that part of my life. And I was in my mid-20s. I gotta make some money and those sorts of things.

So then I got into—my family has a past in kind of a little bit of real estate development on the residential side. So I fell in love with commercial real estate development. And so I did a lot of development projects in Charleston, South Carolina. So I stayed there, developed a lot of that King Street corridor. But then 2007, 2008 came as we were just talking about this beautiful apartment, and that crash was so painful that it changed my life pretty dramatically. Like every young man, I thought I was a genius, right? You become a multimillionaire in your mid-20s. You could do no wrong. This is just a dot plot on the radar. On my way to a billion by 32, right? Who’s gonna stop me? I’m clearly smarter than everybody else.

And you found out a rising tide lifts all boats and it shut it all down. And so the pain of that was so acute that I spent the next few years just trying to figure out, how do you hedge global macro risk? So that way as an entrepreneur, you can go as hard as you possibly can into your idiosyncratic business. So that’s kind of what led me into this whole investing space and long volatility, tail risk, options and thinking about defensive strategies for entrepreneurs.

Jim O’Shaughnessy

And it’s a similar story with a different path for me. I just, from a teenage—I was 17 or 16 and my uncle and dad would be arguing about stocks and I just got the bug. It’s like neither one of these guys know what the fuck they’re talking about because they’re talking about this CEO and this, and it was all surface stuff. And I’m kind of like, don’t you think you should look at how much you’re paying for every dollar of earnings or all that? And so, but what I loved about it was it is the perfect spot for somebody who is insatiably curious and loves to go down rabbit holes.

We were talking about religion, you were just recounting all of your various experiences. I think that religion and religious attitudes inform far more than religion. Right. I think that, you know, you think of Bogleheads, you think of the various, no, I’m a die-hard fill in the blank. And what’s interesting about religion compared to the scientific method is that you can be consistently wrong with all of your predictions in religion and gain adherents.

Jason Buck

Yeah.

Jim O’Shaughnessy

I think of the Seventh-day Adventists—not to pick on them because I’m sure that they’re lovely people. But that was a guy back in the 1800s who started, mathematically proven through the Bible, the world is going to end. I can’t remember, 1846. Right. And so literally he got a hundred thousand people to sell everything, wear white robes waiting for the rapture, and nothing happened. He was like, oh, I got something wrong. And he went back and he ran the numbers again and he came up with a new date. Of course, wrong. And yet there are now 18 million members of this particular sect that descends from him. And it’s not just him. Right. It’s like every major religion makes all of these—it’s coming soon. I always joke the world’s oldest profession is not prostitution. It is predicting the end of the world.

Jason Buck

That’s very fair. What’s the—I’m always terrible at pronouncing this word—millenarianism. Yes, yes. The end of the world. That’s what most religions are at the end of the day. But what you hinted at that I find so fascinating that I’m working on is I do take my background in comparative religions and now I’m applying it to investing and portfolio construction. Because like you said, I always like to mess around with my value-based brethren. I mean, inherently you got to love value-based in general, sure. But now they worship the Buddha, like Buffett, right? And whatever he says from on high, that’s gospel and you can’t tell them. But as any faith-based religion, it’s the pain in the interim, right? Going the past decade without value. No, if we just hold the course, if we just stay strong, right, we’re all going to be lifted together in this rapturous moment. And value, everybody’s going to get their comeuppance in the afterlife, right?

Jim O’Shaughnessy

And you know, that’s another big part of it, right? You see it in market behavior all the time. The people—we had value strategies, we had momentum strategies, we had a variety of strategies because the evidence suggests that on balance they work more often and with better predictability, if you want to call it that, than other strategies. So I in the beginning, like everyone else, read all of Graham’s books and found it compelling. But I also was like, wow, this Mandelbrot fellow is a very interesting guy because I’m sure you’ve read of course that chapter in which he just dissects and just—it doesn’t leave anything living from efficient market theory. Right? But isn’t that an edge? Isn’t it an edge for an investor who’s very happy to fade those consensuses and go their own way?

Jason Buck

Yes and no. We’re getting into a different topic that I find fascinating, like edge or alpha. I’m not sure any of it really exists. There are edges or alpha in arbitrage hunting, right? But you have to persistently arbitrage hunt because they appear and disappear so quickly and it’ll be in a different marketplace. That’s a true edge. But those are extremely rare. And so you go back to kind of efficient markets. But like you’re saying, what mine came from too is people, I find when they’re young, they either start with Buffett and then that just locks in from a young age. Right. That’s part of it. Or like I did, they start with Market Wizards. I kind of started both the same time.

But I loved Market Wizards because you find from reading the Market Wizards books there’s a million ways to make money in the markets. You got to find one that works with your personality so you’ll stick with it, which is really Buffett’s secret. Who else has done the same thing for 80 years? And compounded as we know it, all the wealth came later in life. Right. So that’s the unique part of it. But what I found even reading Market Wizards is a lot of times you had these CTAs or trend followers and it was like trend following plus nothing. They just thought that was the cat’s pajamas. Right. There’s nothing better than that.

But then you run the numbers and you’re like, well, if I pair that with long-only equity beta, I end up with a better portfolio due to the uncorrelated nature. And because they were faith-based in trend following, then they wouldn’t apply that. But now you’re starting to see that last few years, you’re seeing a lot of mutual funds and ETFs come online. They’re pairing those two together. So it comes down like you’re saying, this portfolio construction of all these different strategies that work at different times and all these asset classes that work at different times, whether inflation, deflation, growth or recession, if you pair them together, they all kind of muddle along in a symbiotic relationship. And your timing mechanism can just be rebalancing.

And so to your point, that’s maybe where you’re harnessing a bit of edge or alpha from the behavioral aspects of people. Because you kind of just watch money chase all of these asset classes around the world. What’s the hottest these days? Right. But then the hard part is if you have true portfolio diversification, there’s always a part of your portfolio that you hate. The news media is telling you to hate it. You’re an idiot for owning it. It makes you want to throw up. But if everything’s going up together, you’re not diversified. So that’s the hard part. I think it’s like Brian Portnoy is like always having to say you’re sorry.

Jim O’Shaughnessy

Yeah, I’ve said often that the less sustainable edge, if there is edge at all, is to arbitrage human behavior. Because literally human behavior has moved very little, at least over the recorded history I’ve been able to study, whereas markets—people confuse the climate with the weather. I think weather is obviously very changeable. It’s a beautiful day here now. It was raining yesterday. Climate is very different. It’s a lot more sticky and sticks around. And I too looked at the world in much the same way you’re describing right now. It’s kind of like you’d never know when you’re going to be right and how much pain it’s going to cause. I actually use that as kind of an indicator. If everyone was telling me, you’ve got to drop this strategy, it’s awful. We’re getting fired in this strategy. Everyone hates us, they’re yelling at us. I would put money into it just because it just seemed like a sensible thing to do.

Jason Buck

Tomorrow I’m going to—I’m going to London tomorrow and I’ll see Jerry Haworth from 36South out there. And he’s one of the OGs of kind of the long volatility tail risk space. And he told me once that the only way he can predict when the next market crash is coming is when he has the highest amount of redemptions. He just knows it’s around the corner, right? So once again, arbitraging human behavior. And then the event happens and then everybody rushes to invest because they want a time machine, right? When did Noah build the ark? Before the flood. Before the flood. But everybody comes in after the flood. So that’s what you’re saying. The arbitraging of human behavior is odd to me.

And our mutual friend Meb Faber always says too, when people call him up to talk about one of his ETFs, he’s like, oh, the one that’s down the most. And no, it’s never. It’s the one that’s up the most, right? It is just inevitable. Over and over. But I am sympathetic or empathetic to the idea that human behavior is hard. I think you’ve talked about it before. This is why I also love our business. The P&L every day is black and white. We have a connection with reality that you may not get in a narrative religion where the end times are down there tomorrow, always tomorrow.

Jim O’Shaughnessy

What did you do today?

Jason Buck

Right? What did you do today? And your P&L could tell you you suck every day, right? Or even worse, what kind of job can you go to and lose money for months on end? Right. It’s only a job like this. Obviously, being an ER doctor, ER nurse is much more important than what we do. But it’s an interesting feedback mechanism that we get about reality. And therefore, yeah, you have to think very carefully about what your portfolio looks like over time. But the fairness for the human condition is—it’s one thing to have theoretical inputs and the philosophy and the back test and know through time I’m going to be fine over decades.

But the lived experience, day to day, it just plays on your emotions much harder than people could ever imagine. I always—because we work with a lot of younger investors that had their first liquidity event and they sold their business. And one of the things that’s interesting to me, they always tell me, if the market’s down 50%, I’m a buyer. And I just laugh hysterically every time because it’s just like, you have no idea. But understandably, they don’t have the experience for it. And I think Jason Zweig said it best, I can draw you a picture of a snake, but if I throw a snake in your lap, you’re going to act very differently.

And so what they don’t know is if the market’s down 50%, you’re in the fetal position on the floor, you’re going to ATMs to try to get your cash out. You think it’s the end of the world. The idea that you’d want to buy stocks at that point, you and I have been through this, it’s anathema. Hopefully over time we get enough experience. And then we’re like Howard Marks, and we’re like, well, I have to be buying now or else I’m in an existential crisis either way.

Jim O’Shaughnessy