Derek Sivers, author, entrepreneur, TED speaker, and founder of CD Baby, joins us for another wide-ranging conversation about parenting a teenager who is ready to leave home, why he moves countries on purpose, why nihilism is underrated, and much more! It is his first podcast after more than a year of saying no to every request.

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.

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Links

Show Notes

Derek Sivers & Jim O’Shaughnessy

• Derek Sivers: Author, entrepreneur, and TED speaker, and founder of CD Baby, once the largest seller of independent music online. Derek’s website

• Derek on X: Where Derek shares his writing. Follow Derek on X

• Derek’s TED talks: Including “How to Start a Movement,” his most popular talk. Watch Derek’s talks

• Jim O’Shaughnessy: Host of Infinite Loops, founder and CEO of O’Shaughnessy Ventures, and author of the New York Times bestseller What Works on Wall Street. Follow Jim on X

• Full transcripts: Transcripts and highlights from every Infinite Loops conversation. OSV newsletter

Derek’s Books & Projects

• Useful Not True: Derek’s book on skepticism and choosing beliefs because they are useful, not because they are true. Useful Not True

• How to Live: 27 conflicting answers on how to live, which Derek calls his masterpiece. How to Live

• Hell Yeah or No: Simple mental models for deciding what’s worth doing. Hell Yeah or No

• Anything You Want: Derek’s bestselling book of 40 lessons from starting, building, and selling CD Baby. Anything You Want

• Tech Independence: Step-by-step instructions and a setup script for running your own server and email instead of depending on big tech. Tech Independence

Books & Ideas Mentioned

• Personal Development for Smart People by Steve Pavlina: The book whose idea about seeking surprise sent Derek around the world. Derek’s notes

• China’s World View by David Daokui Li: Derek’s pick for understanding the Chinese government’s point of view. Derek’s notes

• Maverick by Ricardo Semler: The book behind Derek’s short-lived profit-sharing plan at CD Baby. Maverick

• Why Greatness Cannot Be Planned by Kenneth O. Stanley and Joel Lehman: Jim’s reference on why new vantage points change where you want to go. Why Greatness Cannot Be Planned

• The Beginning of Infinity by David Deutsch: The book Jim calls a definitive look at how he sees the world. The Beginning of Infinity

• Nothing & Everything by Val N. Tine: The book on nihilism Derek recommends, with his advice to read only the first half. Derek’s notes

Highlights

“Someday I’ll be able to spin the globe and every little part of the world will feel like home.”

A major turning point in my life is when I read this little idea deep in a book by Steve Pavlina called Personal Development for Smart People […] he said, no, the extreme way to be surprised is to move somewhere far away from home, to a culture that’s as different as can be, where everyday life will surprise you on a minute-to-minute basis. I’m obviously not quoting that word for word, but that was the idea. And I read that idea and it was like an inception, right? I couldn’t get that idea out of my head. And so about nine months later, I was getting into the process of selling my company, and I realised I don’t need to be here in Portland, Oregon, any more. And I had just broken up with my girlfriend, and I was just completely free and unattached to anywhere and anything. And that idea came back. I said, that’s how I want to spend the rest of my life.

I was almost 40 years old, and I thought, “I’ve spent the first 40 years of my life in the US. I want to spend the next 40 out.” And ideally, I want to keep going to more and more difficult places, and each one, stay long enough until it really feels like home. Until it’s like, this is my place, these are my people, this is absolutely my home. And then move on and do it again. And the ideal, the big lightning bolt of a vision in that moment, was that someday I’ll be able to spin the globe and every little part of the world will feel like home. From Kazakhstan to Peru to Saudi Arabia to whatever. Finland will feel like home. I’ll have friends there. I will have spent significant time there. I’ll feel really deeply connected there before I die.

What a cool mission. So that’s what I set out to do. It was 2008, 2009. I had just sold my company. I went off into the world. I went to London for six months, five months, and it really felt like home. So much home that I almost bought a house there. I was like, “Oh, that’s it, I’m done. This is my favourite city in the whole world. I’m gonna buy a house.” I put an offer on a house. Luckily, that offer was refused, because I had to slap myself and go, “Wait a minute. What am I doing? It’s just the beginning of my journey.” And sure enough, over and over again, over the last whatever number of years it’s been since then, I get to a place, I live there for a while, I feel really attached. So attached that I say, “Never mind, this is it. I want to buy a home here. I’m going to live here for the rest of my life.” And again, I have to slap myself and go, “Hold on, wait. This is what I’m supposed to feel. And when I feel this, it’s time to move on again.”

From Manager to Consultant

So every culture, or even microculture, has its own moment where the boy is considered a man, where somebody goes from childhood to adulthood. Some have a bar mitzvah. In my case, I felt it when, just a few months ago, he flew by himself from Wellington to Auckland to Singapore, did the immigration and everything by himself, flew on the plane as an adult, and I just met him in the airport in Singapore. And I went, “Wow, you did it.” And I just noticed internally, something in me shifted. I’m like, you know, he’s really not a kid any more. He’s a young man now. He’s 14 and a half. Wait, no. Anyway, he’s turning 15 in a few months.

And so in my head, I had to adjust that. For kids, I think parents might need to be more of a manager and help make decisions for them. But at a certain point, you have to change the mindset from being a manager to being, like, a consultant. To put it more bluntly, they fire you as a manager, and you just have to hope that they will hire you back as a consultant.

Edited Transcript

Jim O’Shaughnessy
Derek, you are absolutely one of my favourite polymaths, one of my favourite people in general. And I read…

Derek Sivers
You too. Sorry, I have to interrupt you to say, yeah, you too. So, audience listening: I took a year-long podcast break. Actually, it’s been a little more than a year. I’ve said no to every podcast request for over a year. And then Jim emailed and asked. I said, “You know what, for you, yes.” I really loved our conversation a few years ago. I just adore you and what you’re doing. And so yes, no to everybody else and yes to you.

Jim O’Shaughnessy
Thank you so much. It truly does mean a lot to me. I want to hit you with something you said, because it resonated so deeply with me. And again, I think it’s one of the reasons why we vibe so well together. You said, “I want to make articles, books, websites, music, companies, systems, apps, and especially new ideas.” And I read that and I laughed and I said, “Me too.” But then I thought, you’ve talked a lot about your son, and I’ve been really incredibly impressed with your commitment to him. 30 hours per week, giving him your completely undivided attention. I mean, I don’t even touch that league, and I have three kids. By giving him that 30 hours a week, did you get lots of things out of it as well?

Derek Sivers
Perspective. I think that’s a huge one. When everybody’s freaking out over an election, over AI, over something in the news, over whatever, I’ve got the perspective that my kid and I are out in nature, or he’s fascinated with a book, whatever it may be. It keeps the world events in perspective for me. I never forget what’s most important here.

Jim O’Shaughnessy
Absolutely. And if you could put yourself in his shoes, does he realise how unusual that type of commitment from a father is and was?

Derek Sivers
In his words? He said, “I seem to be the only kid that has a dad.” He said, “You know, all my friends at school, they either literally don’t have a dad or their dad is kind of barely in the picture.” He said, “I’m like the only friend I know that has a dad.” So to me, the thing I wanted to communicate in action, not just words, is that he is more important than anything that might come through any screen.

Jim O’Shaughnessy
I have the greatest of admiration for that. I remember... I was young when I had my first child. I was 24.

Derek Sivers
Wow.

Jim O’Shaughnessy
And my parents were saying, “You don’t know what unconditional love is, Jim. You really don’t.” I was like, “Yes, I do. Yeah. I mean, I have unconditional... Mom, I have unconditional love for you. Dad, maybe not as much. But Mom, certainly for you.” And then I held my son Patrick, and I started to cry, and I realised in that instant that they were right. I really didn’t know what that feeling was. And it’s an emotion. We’re going to get into that a little later, because I think we both agree that, for the most part... well, I think it was... my friend Rory Sutherland says, “We think that our brains are the Oval Office, when actually they’re the press office.” We make many of our decisions emotionally and then pepper them over with rationality. I used to put a GIF up on Twitter that says “Because of reasons.” But your son is making a big move right now. He’s decided to move to Singapore. And you quipped that you’re trying to figure out how to move from being his manager to being his consultant. How’s that going?

Derek Sivers
That’s a new change. So, sorry, to be clear, he’s not planning on moving to Singapore. That was just our moment. So every culture, or even microculture, has its own moment where the boy is considered a man, where somebody goes from childhood to adulthood. Some have a bar mitzvah. In my case, I felt it when, just a few months ago, he flew by himself from Wellington to Auckland to Singapore, did the immigration and everything by himself, flew on the plane as an adult, and I just met him in the airport in Singapore. And I went, “Wow, you did it.” And I just noticed internally, something in me shifted. I’m like, you know, he’s really not a kid any more. He’s a young man now. He’s 14 and a half. Wait, no. Anyway, he’s turning 15 in a few months.

And so in my head, I had to adjust that. For kids, I think parents might need to be more of a manager and help make decisions for them. But at a certain point, you have to change the mindset from being a manager to being, like, a consultant. To put it more bluntly, they fire you as a manager, and you just have to hope that they will hire you back as a consultant.

Jim O’Shaughnessy
And I love that point because it is so true. The idea that it’s horrible for a child not to fire you as the manager. I kind of see that as a failure to launch.

Derek Sivers
Yeah.

Jim O’Shaughnessy
And my wife was more emotional about it than I was, but I was incredibly proud when each of my children (I have a son and two daughters) came in at roughly similar ages and said, “You know, Dad, I really appreciate your advice and what you’re telling me I ought to do, but I’m going to make this choice. I’m going to decide what I want to major in. I’m going to decide where I want to live.” And I was like, yeah. Because, as I mentioned, we were young, right? We were 24 years old. But we talked a lot about how we wanted to raise our children, and the line that we could both agree on was: we want them to be great adults.

Derek Sivers
Yeah.

Jim O’Shaughnessy
And when you make that your watch phrase, right, it precludes all sorts of things that people naturally go to. “My house, my rules.” “Because you’re living under my roof, you’re going to follow my direction.” And that doesn’t make a great adult. That makes a compliant, sheepish, non-curious individual. And in a similar fashion, I have a pretty good memory for anything I read. And so my kids (this is pre-internet for the most part, or early internet) would use me as Google. “Hey, Dad, you know who was the French representative at the Congress of Vienna?” Talleyrand, in case you’re curious. But we had a massive bookcase, and I would just look at them and say, “Look it up in there.”

And we had the whole family together, which doesn’t happen too often, because one of my three, my daughter, lives in California and the other two live out here on the East Coast. And we were reminiscing about it, and all three kids basically said the same thing. When we were... when they were saying, like, well, what did you like about the way... you know, “How did we damage you, first off? But what did you like about the way that Mom and I raised you?” And all three said that what it instilled in them was that voracious curiosity. Because inevitably, if you’re trying to find out that it was Talleyrand at the Congress of Vienna after the Napoleonic Wars, you’re going to run into some other material if you’re actually looking it up in books.

And one of my kids was like, “Yeah, I read for like a couple hours. I was fascinated by the French Revolution, and that led to my curiosity about other things.” And so I think it’s a measure of your success, in my opinion, as a dad, that he wants you to be a consultant now and he’s asked for that, and you’re absolutely willing to go that way. What do you think are going to be the main differences, acting as a consultant as opposed to a manager?

Derek Sivers
I’ve been slowly prepping him for this for years. So let’s take a little example of whenever he has a school holiday. Here in New Zealand they have two-week holidays three times a year and then a one-month summer holiday. So whenever it’s a two-week holiday, I let him decide what he wants to do with it. His mom has a full-time job, but I don’t. So all the school holidays are on me to take him around or do something, or whatever he wants. So there have been school holidays where he says, “I don’t want to do anything. I just want to stay home and do nothing.” I said, “Okay.” And then he’ll pay the consequences of that if halfway through he regrets it and wishes that he would have gone somewhere else.

Jim O’Shaughnessy
Right, I have to stop you, because that goes against every fibre in your being.

Derek Sivers
How so?

Jim O’Shaughnessy
You’ve often said that you want to take action. You don’t want people who just want to Netflix and chill, right? So did you flinch a little when he said that?

Derek Sivers
Oh, of course. Yeah. So I could give more examples. Like, if he said, “I want to go to Europe,” I’m like, “Really?” Or three years ago, he said, “I want to go to China.” And I had only been to China once before in my life, and it was rough. It was not pleasant. It was 2010 and I went to Guilin and it was pretty nasty. And so when he said he wanted to go to China, I said, “Why?” And he said, “You know, Kung Fu Panda. It just seems interesting.” And I went, “All right. You know, in the name of your education, you lead the way. You go plan the trip. You decide where we’re going to go.” And so he did.

And it ended up blowing my mind, you know. So now I love going to China, and I’ve made a bunch of friends there, and I’ve been a bunch of times since, but it was because he was leading the way. But it can work either way. There have been times, even on a day-to-day level, where he will choose to say, “Let’s go have an adventure. Let’s go sleep in the woods, but without a tent. Let’s just bring the sleeping bags and a tarp. I want to sleep in the woods tonight without a tent.” I’m like, “Okay, if that’s what you want.” And halfway through, he really regrets it. In the middle of the night, he’s like, “Dad, I hate this. Let’s go in.” I’m like, “I thought that would happen.”

But the important thing for each of these examples is that I want him to feel the consequences of his choices, so he leads the way. I’m his faithful assistant, but I want him to get lots of experience leading the way, feeling the consequences of his choices first-hand, so that, yeah, he feels the pain of a bad choice or the joy of a great choice of his own, instead of me making those choices for him.

Jim O’Shaughnessy
Yeah. I have some grandchildren who are approaching the tweener category, and I was talking to my son, who’s their dad, and one of the things he said, which was very adjacent to what you said... we were talking about how much you’re going to allow them to make up their own minds and do their own thing. And he said, “As much contact with reality as possible is what I’m going to advocate.” And I was just like, God bless you. Because in this era where everything is just, you know, helicopter hovering, “Don’t do that. Do this.” I mean, that’s a horrible way to turn out a good adult. You are constricting them and putting them in a straitjacket. It’s just, don’t do that. Don’t do that. Let them make mistakes.

Let them come into contact with reality, because that’s understanding the consequence of your own actions.

Derek Sivers
I think one of my favourite parenting sentences was “Broken bones heal faster than fears.”

Jim O’Shaughnessy
They really do.

Derek Sivers
Isn’t that great? Like, you see your kid climbing on the edge of a cliff, and everything in me is just saying, “Watch out.” But instead of, like, “Wait, no, watch out,” I’m just gonna sit and observe, and if he falls, he breaks an arm, so be it.

Jim O’Shaughnessy
Didn’t Hemingway say we are stronger at the point of the healed bone fracture? Something along those lines. We are much stronger after it heals, at the point of fracture. And so I think that as difficult as that impulse, not to... “Don’t do that,” is. I mean, obviously, I have very young grandchildren, too, and, you know, the first couple of years, you’re essentially trying to stop them from killing themselves. But when they get to a point where they are able and capable to make their own decisions, I am entirely in your camp. Let them do that, because that’s the only way that they’re going to be able to really learn, you know, exactly the way the world works. Moving on. I’ve heard that you yourself are thinking about moving.

Derek Sivers
Yes.

Jim O’Shaughnessy
Which, when I first saw it, I was surprised, given what we... In our previous conversations, you were like, “New Zealand is it.”

Derek Sivers
Oh, really?

Jim O’Shaughnessy
Yeah, yeah. You were like, “This is the place. This is, like, the perfect environment for me.” It didn’t surprise me when I read it. I’m like, of course Derek is going to move. But elaborate on that. What...

Derek Sivers
Yeah.

Jim O’Shaughnessy
Why? Why move from New Zealand to Bangalore?

Derek Sivers
Okay, so, context. I should write about this soon. This was a real key moment in my life. A major turning point in my life is when I read this little idea deep in a book by Steve Pavlina called Personal Development for Smart People. It was an okay book, a little too verbose. And this brilliant idea was like 300 pages in, where it said, if you want to keep growing and learning, you need to be surprised. And one of the best ways to be surprised... no, sorry. He said a good way to be surprised is to read a bunch of books about subjects you know nothing about, and try to do things in your community that you ordinarily wouldn’t do, join groups that you ordinarily wouldn’t join, do hobbies you ordinarily wouldn’t do. And he said, no, the extreme way to be surprised is to move somewhere far away from home, to a culture that’s as different as can be, where everyday life will surprise you on a minute-to-minute basis. I’m obviously not quoting that word for word, but that was the idea. And I read that idea and it was like an inception, right? I couldn’t get that idea out of my head. And so about nine months later, I was getting into the process of selling my company, and I realised I don’t need to be here in Portland, Oregon, any more. And I had just broken up with my girlfriend, and I was just completely free and unattached to anywhere and anything. And that idea came back. I said, that’s how I want to spend the rest of my life.

I was almost 40 years old, and I thought, “I’ve spent the first 40 years of my life in the US. I want to spend the next 40 out.” And ideally, I want to keep going to more and more difficult places, and each one, stay long enough until it really feels like home. Until it’s like, this is my place, these are my people, this is absolutely my home. And then move on and do it again. And the ideal, the big lightning bolt of a vision in that moment, was that someday I’ll be able to spin the globe and every little part of the world will feel like home. From Kazakhstan to Peru to Saudi Arabia to whatever. Finland will feel like home. I’ll have friends there. I will have spent significant time there. I’ll feel really deeply connected there before I die.

What a cool mission. So that’s what I set out to do. It was 2008, 2009. I had just sold my company. I went off into the world. I went to London for six months, five months, and it really felt like home. So much home that I almost bought a house there. I was like, “Oh, that’s it, I’m done. This is my favourite city in the whole world. I’m gonna buy a house.” I put an offer on a house. Luckily, that offer was refused, because I had to slap myself and go, “Wait a minute. What am I doing? It’s just the beginning of my journey.” And sure enough, over and over again, over the last whatever number of years it’s been since then, I get to a place, I live there for a while, I feel really attached. So attached that I say, “Never mind, this is it. I want to buy a home here. I’m going to live here for the rest of my life.” And again, I have to slap myself and go, “Hold on, wait. This is what I’m supposed to feel. And when I feel this, it’s time to move on again.”

So I have not been doing that mission as planned, because I was in a one-year relationship with a woman, and after we broke up, she got pregnant, and oops, that’s where my son comes from. And unfortunately, she hates travel, and she’s his mom. So here we are in Wellington, New Zealand, where Mama works for the government in Wellington. And I’ve been here for 14 years, pausing my mission. But now my boy is also kind of one foot out the door.

He really wants to go away to boarding school somewhere. He’s also got this travel lust. He feels like a world citizen. He was born in Singapore. He’s a citizen of four countries. His mom’s from India. We’re both citizens of India as well because of her. So he’s yearning to get out into the world. So that’s the background context. Do you want to ask anything about that before we go to Bangalore in particular?

Jim O’Shaughnessy
Yes, I do.

Derek Sivers
Okay.

Jim O’Shaughnessy
And, big surprise, right, your son... where would he like to go to boarding school? Does he have a particular place that he wants to go already, or is...

Derek Sivers
He just, like... I don’t know. Jim, can you pull some strings somewhere? What do you got?

Jim O’Shaughnessy
The honest answer is yes, I probably could.

Derek Sivers
He just wants to get out of here, honestly. There’s a school in Kobe, Osaka, a Canadian school in Kobe, Osaka, he likes. There’s a school in Tamil Nadu, India, he likes. There’s the United World College in Phuket, Thailand, that he likes. He just wants to get out of here. He just wants to travel.

Jim O’Shaughnessy
He’s got good taste. Those are... I’ve been to all of those places.

Derek Sivers
Wow.

Jim O’Shaughnessy
Okay. Yeah, yeah. Those are all sweet, sweet spots. And you’re going to let him... Are you going to act like the consultant, or are you going to act like the manager when he comes in?

Derek Sivers
Oh, come on, take a guess. Yeah, no, this is totally his doing. His choice. The applications and everything, he’s doing them himself.

Jim O’Shaughnessy
Yeah. What does he think about you wanting to move to Bangalore?

Derek Sivers
Oh, he loves it. He would do it in an instant, too, if Mama said okay.

Jim O’Shaughnessy
Yeah, yeah.

Derek Sivers
He loves it there.

Jim O’Shaughnessy
It’s interesting to me that she hates travel. She seems to be maybe the other... My wife once joked that she made me a regular, normal human being, so maybe that’s what’s going on. It sounds like he inherited your love of travel and novelty and everything else. Yeah. How does Mama feel about that?

Derek Sivers
Totally against it.

Jim O’Shaughnessy
Yeah.

Derek Sivers
So here we are. Yeah, it’s, you know, it’s interesting. We all probably, at some point in our past, especially when dating, have felt this feeling of trying to be who you think the other person wants you to be. And so I think when she met me, and she saw that I was quickly passing through America on my big international journey, she basically brought out that side of herself and said, “Yeah, I can’t wait to leave America. Let’s get out of here forever.” Even though, in hindsight, that was probably, you know, 1% of her felt that way. She brought out that 1% and presented it to me as who she is. So we were dating under that mindset.

And then as soon as we actually did leave America, like, literally as the plane is taking off, she freaked out and said, “I want to go home. I want to go home.” And so it turns out that she didn’t actually want that. She thought she did. And I was critical of that at first, of course, because it affected my plans very deeply. But in hindsight, I realised, yeah, we’ve all done versions of that. You meet somebody and you bring out the side of yourself that matches who they are. Maybe even just in the name of making friends. Yeah. You meet somebody that can relate to a side of you that’s rock and roll, into heavy metal or whatever. So you kind of bring out that one thing.

Even if there’s just one heavy metal band you like, you’re like, “Oh, heavy metal, yeah, I love Iron Maiden.” You bring out that side of yourself in order to have a bond or connection with this person. And then you meet somebody else that’s really into quiet and poetry, and so you bring out that side of yourself. “Oh, yeah, E. E. Cummings is one of my favourite poets.” You know, we know how that feels. And so you can’t fault somebody for doing it, especially when dating. But, yeah, that’s what happened. That’s why I had a kid with somebody that hates travel.

Jim O’Shaughnessy
You know, as you were talking about how we change ourselves for people that we love, I recently reread a thing by Tony de Mello. I don’t know whether you’ve read any of his work. He was an Indian guy. He unfortunately died way too young. He was a Roman Catholic Jesuit priest who got enlightened in an afternoon he spent with a rickshaw driver who was dying. And he said, “Can I just pay you for the rest of the day and talk to you?” And the guy was like, “Yeah, absolutely.” Anyway, that’s a much longer story, but it got me into all of his books. And the thing that I reread was about love, especially for a spouse or a partner. And Tony’s view was pretty hardcore. It was this: if you cannot say to your beloved (and that’s the term he used, “your beloved”), “I leave you free to be yourself, to seek out what interests you, to follow your own passions, to follow your own interests. And if we still are together, that’s lovely, but if we aren’t, that’s going to be lovely too.” He goes, you don’t actually truly love that person if you can’t say that to them. He said, because then what you’re doing is a transaction. It’s conditional. “If you do this, then I will give you, or do, this.” And it made me really think quite a bit about just the nature of intimate relationships, et cetera.

And kind of do an inventory on how many in my own life were, you know, if you were being just really blunt about it, are they transactional or not? And unfortunately, I found that too many of them actually were transactional. Now, lucky for me, I found a lot that weren’t. But it’s natural for us. I mean, you know, we’re memetic creatures, and mirroring, and especially if we really want to get with somebody, or want to date them or marry them, we’re going to make a lot of concessions. And then what happens? I’ve been married 44 years to the same woman, but what happens is, generally speaking, that goes on for the first, oh, seven years, if you’re lucky, and then you start reverting back into, you know, the real you. And that’s when the challenge comes, right? If you can make it through that.

If you can make it through “But you always said you loved...” “Actually, no, I fucking hate it, and I just really don’t want to do X, Y or Z any more.” If your wife or husband can say, “Okay, that’s fine. That’s great,” things are going to look pretty good for you. But I hear you, and it’s actually quite true. I was reviewing our last conversations, and you put us both in the Miles Davis, David Bowie camp, right, where we just want to try new things. A lot of people are happy to just kind of get good at something and then just do it, right? Just, like, same shit, different day. I hate that. I know you hate that. What do you think it is about people like us who just... “No, I don’t want to keep doing that same thing. I want to try new things.”

Derek Sivers
Okay, wait. I’m feeling that discomfort of a loose thread that we didn’t tie up, because I started to answer your question about why Bangalore, and then I got on my long tangent about how I wanted to...

Jim O’Shaughnessy
Let’s do Bangalore and then we’ll come back.

Derek Sivers
I feel I should close that loop. So, yes, Bangalore. Anybody, if you’ve not been there: the city itself is awful. It’s terrible city planning, terrible infrastructure, but the people there are so wonderful. Kind of in the same way that when I met you three years ago, as soon as we started talking, I was like, “Oh, I like this guy. You’re one of my favourite people to talk with.” And that’s really rare, right? So it can happen with places. So to me, Bangalore is the number one spot in the world where almost everybody I meet is such a great conversationalist. I don’t know what it is about that place, but the people I met there are just so fun to talk with. And I just feel such kindred affection and intellectual stimulation. I just love the people there.

So that, to me, is why Bangalore is top of my list of where I plan to live next, as soon as I can leave New Zealand. I don’t mean to make it sound like there is somehow a move against New Zealand. That’s why I had to give the bigger context. When you said, “Why do you want to move to Bangalore? You said you love New Zealand,” that’s why I had to say, yeah, I want to love everywhere. I also loved Santa Monica, living on the beach. I also loved Oxford, England, and I’d probably be living there still if Covid didn’t send me back. I also loved Woodstock, New York. God. I also loved living in Union Square in New York City. I lived there for a few years.

There have been a bunch of places that I loved, and now Bangalore adds to that list. And don’t be surprised in the future if you also hear me say, “Okay, I am moving to Shanghai.” “Okay, everybody, announcement: I am moving to Istanbul.” You know, I hope to continue to move to places and stay there for a while and fall in love and move on. So there’s the context for Bangalore.

Jim O’Shaughnessy
And just to have my end of sewing that thread up: that’s what makes life fascinating, interesting, enjoyable. I can’t imagine not wanting to experience something new, not wanting to learn something new. I would be beside myself. It would really just bum me out. Before I sold my company, an asset management company, I’d really grown tired of just the same speech, the same questions, the same, the same. And so I would try anything to mix it up, right? So I’d make sure I read the local newspaper so that I could change what I was saying to people.

I would look for something interesting that was way outside of asset management, that you could nevertheless weave in, and get people to go, “Oh, I looked at it that way.” But it just got to the point where it’s like, just doing the same thing, it just turns your brain off, I think. Well, yeah, you’re nodding. And I know that you are a very similar mentality to my own.

Derek Sivers
Yeah. Well, I assume that you brilliantly just transitioned back into the next topic that we left, that you were just about to open, which is that... completely accidentally. Oh, really? So some people can just dive deeper and deeper into one thing. This is maybe the comparison we made last time, of AC/DC versus David Bowie. Some people just want to really perfect that one thing, you know? I don’t know Georgia O’Keeffe’s whole career, but it feels to me, from what I know of Georgia O’Keeffe as a painter, she was trying to get deeper and deeper into this one style of painting. Whereas Picasso went through many different phases and tried different approaches. Got famous for his Cubist thing, but that wasn’t his only thing. So it is possible, I think, to not stagnate while still doing one thing.

Some people just have that personality type. They can just dive deeper and deeper into one thing or one place. They can stay in one place. I feel it’s almost a fault of mine that I can’t imagine staying in one place for more than a couple years. But some people get really into one place, really commit, and they’re able to completely thrive and flourish in that one place, or in one career, one expertise, going deeper and deeper into classical piano or whatever it may be. To me, I think my value system, of what it means to live a good life, a full life, is to do lots of different things. I just have this idea of being on my deathbed, looking back and going, “Wow, look at all those places I lived. Look at all those different things I did. Look at all those different lives I lived in my one life.” That’s what I’m aiming for. I want to live lots of different lives in my life. And hence my last book, called How to Live. It has, like, 27 different opinionated versions of “Here’s how to live. Here’s what to do.” “Live for the future.” “No, no, live for the past.” “No, no, live for the present.” “No, no, just get rich.” “No, no, no, do nothing.” And that book was really a reflection of my soul, because that’s how I really think. I want to live many radically different lives in my one lifetime. So that also leaves me very non-judgemental about any given philosophy or approach to life.

I could imagine living a very greedy life for a while, and living a very altruistic life for a while, and living a very hedonistic life for a while, and living a very diligent, prudent life for a while. Like, why not embody all of these different approaches to life, non-judgementally, to see how they feel, and just try them out, to know that you did it?

Jim O’Shaughnessy
Amen, brother. Because I love the addition of the non-judgemental. I think that so many people get it in their noggins that, you know, this is the one true path. If you deviate from this one true path, you’re either a heretic or, you know, an other. I mean, one of the things that’s really bothered me about, oh, maybe the last 10 years is just all of this tribalism, and all of this othering, and all of this labelling, and all of this, you know, God, “If you’re not with us, you’re against us.” And no, try to understand the other point of view. I’m hugely into AI, right? I’ve kept journals since I was 20, actually younger. I don’t have many good quotes in the earliest ones, but from 20...

I have been waiting for AI. I called it synthetic intelligence in a 1984 journal. I’ve been waiting for it all my adult life.

Derek Sivers
Before it was cool. Just say it. Come on, just say it.

Jim O’Shaughnessy
Before it was cool, I really was into it. And so now that I have it, I’m like a kid in the candy store. One of the things that I do is I just routinely take something that I think I’m really vehemently opposed to, and then I go to the large language model and say, “I want you to steelman this point of view.” And then I read it, and I think there hasn’t been a single time when I haven’t thought, you know, they actually have a point with this particular thing here. And it’s, to me, so liberating, because it’s just like putting it in a bin and labelling it and saying “bad” and “I’m opposed.”

Because when you do that, you shut down your reticular activating system and you don’t see any of it. Your brain literally just makes you blind to it. I could send you the text, I could send you the link to the article, and if you had put it in that bin and labelled it as bad (I’m not saying you specifically), yeah, it just goes away. And so I think that the non-judgemental part of it is the key. And, you know, it also feeds into, like, Claude Shannon’s information theory, right? Information theory. Basically, he posits that information is novel. And he says, if you’re looking for the information coefficient, or how much information is in a given thing... and then he gives the example: a poem is filled with information; a political speech has none. Because one is simply trying to get you, through repetition, to go, “Yes, that is the right path. Yes, that particular policy is the one that people like me are going to support.” The people like me, right? And I like people who aren’t like me. I like to talk with people who are completely different than me, because I always learn something. I mean, I had a profound conversation. I was in Miami, and my wife and I were walking along, and there was a very rough-looking character, clearly a member of a motorcycle gang, sitting in the place a bouncer would sit in front of a club. And so I figured he’s the bouncer, and he’s tatted up and he’s smoking, but he’s not smoking, he’s vaping. And this is back when vaping was brand new.

And I looked at my wife and I go, “Look at this. He’s vaping, he’s not smoking a cigarette. I gotta go ask him.” She’s like, “Don’t go. Leave him alone. Don’t go over there.” Anyway, I go. And I’m like, “Hey, I just got to ask, what’s the deal? Why are you vaping and not smoking?” And he’s like, “My old lady said she’d throw me out if I didn’t quit cigarettes. So this is the next best thing.” Anyway, that was our introduction, but we got into, like, a 45-minute conversation...

Derek Sivers
Oh, I love that.

Jim O’Shaughnessy
...about, like, how do you know who you’re going to let in and who you’re not? And he started giving me all the tells for people that he knew were going to bring the energy down, versus the people who would bring the energy up. And actually, I put that into my toolkit, because he was right about a lot of the things he said. And so it’s just like, if you’re willing and you’re able to, those kinds of conversations can be just filled with gems that you yourself are never going to think about.

Derek Sivers
I love that. That’s what I’ve been trying to do with reading books like Understanding China’s Worldview by David Li, which is a wonderful book that tries to explain, from the Chinese government’s point of view, here’s how they see things, here’s why they feel that what they’re doing is the right thing. And you could do the same with any culture on earth that you think is wrong, or the people are bad, or it’s evil, if you try to see it from their point of view. It’s fascinating, because countries themselves, in my mind, are embodied philosophies. Every country, or even some cultures inside a country, are embodying a certain approach to life.

Jim O’Shaughnessy
Yeah.

Derek Sivers
Through governance. And so, for the most part, unless it’s a complete disaster, it is a valid working philosophy. It might be a messy one. It might not be your favourite in the world. But it’s valid, and it’s great to understand somebody else’s working philosophy.

Jim O’Shaughnessy
And what did you take away from... Actually, since the last time we talked, which was three years ago, in ‘23: what would 2023 Derek think... If you could think of an example that 2023 Derek would be shocked that you did in 2026. Like, “Oh, I can’t believe he did that.”

Derek Sivers
Ooh, that’s a good question. Huh. I have one, but it’s one that I promised not to tell, so I can’t tell that one yet. Ask me again in a couple of years and I can tell. But let me think of what I can say. Actually, let’s go back just one year, to 2025 Derek.

Jim O’Shaughnessy
Okay.

Derek Sivers
All right. I don’t know if this doesn’t need to be secret. I really want to live in China, partially for a few reasons. Wait, have you been there? Or where have you been in China?

Jim O’Shaughnessy
I’ve only been to Hong Kong. I’ve not been to the mainland.

Derek Sivers
Wow, okay. Oh, Jim. Okay. Such a huge difference between Hong Kong and even just... you could walk across the pedestrian bridge and you’re in Shenzhen, and it’s just a night and day difference. Amazing. So I really, really like the quality of life in Chinese cities. I haven’t been to the countryside much, but the cities are so nice. It’s almost like the way that we used to think of Switzerland, this kind of top-of-the-Human-Development-Index kind of quality of life, where everything’s amazing, everything’s perfect, everything’s beautiful, everything’s clean, everything’s great. That’s what the Chinese cities are like now. So, number one, comfort. But number two, the kind of thing we’re talking about, you talking to the bouncer: trying to really deeply understand somebody else’s contradictory worldview.

Contradictory to the one that you grew up with, the one that comes naturally to you. Trying to deeply understand that different worldview. As I said earlier, I want to do that by living in places. Not just visiting, not just reading the books. I really want to try living there until it feels like this is home. So China, OMFG. Hell yeah, I want to live in China. So one of the best ways to do that, besides going and hoping that some company hires me to get a work visa, is to incorporate a company. While I was there, I met a Serbian woman who was in the same position. She moved to Shanghai to work for a Shanghai company, but then when Covid hit, the company fired her. But Shanghai was home at that point. She has a husband and a son in school. She didn’t want to leave. And so she found out that you can (this is what I was getting to) incorporate a company in Shanghai for just a few hundred dollars, and pay a local agent to take care of everything, all of the annual filings and renewals and taxes. Total price will cost you about $1,000 a year. And now you, as the owner of a Chinese company, can sponsor your own work visa that turns into a resident visa. So I now...

Jim O’Shaughnessy
Loophole!

Derek Sivers
Yeah, I now have a Chinese name. My Chinese name is Shen Si Wen. And my Chinese company is named, like, Shen Si Wen Consulting Company, where I’m the owner and director. And again, as soon as I am able to leave New Zealand, I will also be moving to Shanghai to live there as the owner of my Chinese company.

Jim O’Shaughnessy
Very cool. Are you going to split time between there and Bangalore, or...

Derek Sivers
That’s my plan.

Jim O’Shaughnessy
Yeah, that’s the plan. I think that for a lot of people listening to this, one of the things that holds people back is this, in my view, sort of irrational desire for certainty, right? The way I look at the world, only a madman is entirely certain, right? I was talking to a colleague before we jumped on here, and he’s like, “Well, there is the sun rising tomorrow.” And I said, “It’s a probability. It’s a very high probability.”

Derek Sivers
I’ve said the exact same one. I love that. I’ve told people before, you know, “It’s not certain that the sun’s rising tomorrow.” And they’re like, “Shut up.” I’m like, “No, I’m serious.” Yeah, okay, thank you. I love that you just said that.

Jim O’Shaughnessy
He goes, “You take things just too far.” And I went, “No, I mean, it’s true. It’s true. It’s a very high probability.” I don’t get worried about it because, again, if it doesn’t come up tomorrow, I won’t be around to feel that anxiety, right? But I think this illusion of control (and I use that term specifically, it is an illusion of control), I think people cling to it and become almost desperate when they can’t feel a sense of certainty about things. And I think that has caused more problems, in my opinion, in a variety of human societies than almost anything else. This idea that... well, you express it very well in your books. Like, is it true? What’s true? Right?

And I have conversations with people who are super bright, super switched on, everything, and then I hit that wall, what I call the wall of their certainty.

Derek Sivers
Yes.

Jim O’Shaughnessy
And I make an effort to try to chip away, but I think it almost is an emotion rather than a rational belief. Am I just babbling here?

Derek Sivers
No. Okay, I want to try to join you in this topic. I’ve never talked out loud about this, so I hope I’m able to communicate this. Okay. I’m picturing one of those little sliders. Say you have a bar graph that’s a set width, and say two thirds of it is blue and one third of it is orange. But you can move the little slider over so it becomes, say, three quarters orange and one quarter blue. Right. Okay. So, to me, let’s say that orange and blue are a desire or a need for certainty, and the other one is the need for uncertainty. I think some people, in their nature, have a desire for more certainty than other people. And I think that’s just a DNA nature kind of thing. Who knows where it comes from?

But just like you have three kids... if you’ve ever had two pets, you know that even little pets have different personalities. Even if they’ve never been more than a few inches apart their whole life, there is this nature. And some people do just have a nature that wants more certainty, and some of us have a nature that wants more uncertainty. But the reason I’m thinking of it as a slider is it can move. In times where, say, you’re feeling sick, like, you get really sick and you don’t want any uncertainty right now. “I don’t want any adventure. Cancel those plans. I just want to be home in my comfortable bed. Never mind this whole adventure. I’m sick.” I’ve felt that, too.

I was off adventuring far away, and then I got Covid while travelling, and suddenly I was just curled up into a ball. It’s like, “I want to go home.” And it was interesting to feel that. I didn’t want to meet anybody new. I didn’t want to try anything new. I just wanted to go back to my familiar, because I was feeling so helpless or weak.

Jim O’Shaughnessy
Yeah.

Derek Sivers
But then that gives me compassion for people who feel that way a lot of the time. And some of them I’ve been very close to, that just their whole outlook on life is like, “I’m barely hanging on here. I’m barely making it through the day. I don’t want to hear any of your crazy big ideas, Derek. I don’t know. I do not want to go to China. I do not want to go to India. I want to go to my favourite restaurant, and I want to watch my favourite show, and I want to go sleep in my bed. That’s all I want.” You know, maybe because they’re feeling weak, they’re feeling a desperate need for more certainty. And okay, I can understand that now. I have felt that myself.

But some people go through life like that. Maybe their slider’s over at 90%, that they want 90% uncertainty, and just a tiny little bit of, you know, “Two weeks a year I’ll go to Europe for a holiday” kind of uncertainty. That’s enough for me. Yeah. But we can’t fault somebody for having that slider in another place, because it might be their circumstances. You could imagine, like the movie Trading Places, that if suddenly they were flipped into a different position, they suddenly win the lottery of life, they’d feel full of confidence. They wouldn’t feel helpless any more. They’d feel full of daring, risk and adventure. And they’d say, “You know what? My slider has moved. I know I used to be that way, but yeah, let’s go to Afghanistan. Give me a rifle. Let’s see what happens.”

You know, they might be full of adventure, the same person, same DNA, but their circumstances can change them too.

Jim O’Shaughnessy
So I actually love that, because you’re absolutely right. Having been there, getting Covid... I was lucky enough to get Covid. I was one of the patient zeros. I got Covid before anyone knew that it was called Covid.

Derek Sivers
Once again, before it was cool.

Jim O’Shaughnessy
Well, this is an area where I was desperate to not be cool, because, literally, I was alone in my apartment in Manhattan, and I called my wife, and I said, “I’ve got the worst flu I’ve ever had. My temperature is 105, and I haven’t eaten anything. Will you please come take care of me?” And she was like, “Let’s see how you’re doing in a couple of days.”

Derek Sivers
Wow.

Jim O’Shaughnessy
And it’s funny that it’s the same illness, because I felt exactly like you did. I was like, “Oh, man.” Normally, if I’m sick, I’ll read a bunch of books, I’ll watch TV, I’ll do something, watch a movie or documentary that I never got to, et cetera, to keep my mind occupied and to, you know, learn something new. Man.

For the first four days of that, nothing. All I had to drink was water. Didn’t eat anything. The fever ultimately went down, and obviously I got better. And then, of course, when I re-emerged, then the lockdown starts. I’m like, “Oh, great. I just spent 14 days on my own, and now we gotta do it.” At least I’ll have other people. But I do... In fact, I think you could take that even further, right? People who are in very chaotic circumstances. I have some people who work for me who are from the Ukraine, and they still have family in the Ukraine. And it’s hard for me to conceive when they tell me the average day of their parent who’s living in Kyiv. And I just tried to model that in my own head.

And I’d be like, I would be so out of there. And so that’s an area where I would move my dial over to “I want much more certainty.”

Derek Sivers
Yeah.

Jim O’Shaughnessy
Yeah. So I like that distinction. I think that makes a ton of sense. You know, the last time we talked, we were also talking about the idea that ideas were wonderful multipliers, but execution is where you create the value. Now, now we have AI. Okay.

Derek Sivers
I hadn’t thought about this.

Jim O’Shaughnessy
Yeah. And one of the things that I’ve thought about is, we can now get a competent first version of a company, of an app, of anything. And then where do we find the scarce part of execution? If we can press a button and have it one-shot a beautiful website that meets all of our specifications, right, so it’s our taste, it’s everything that we want... where is the scarce part that execution brings? Is it in judgement? Is it knowing the audience that you’re making it for? Is it taste? What do you think?

Derek Sivers
My only real answer is, I don’t know. Yeah.

Jim O’Shaughnessy
That’s a great answer, though.

Derek Sivers
I had not thought about this at all. So I could spout some crap off the top of my head, but it would not be worthy of your audience’s intellectual...

Jim O’Shaughnessy
One of the things I’m actually proudest of from my prior asset management career: I had a guy come up to me as I was leaving the firm that I sold and starting my new adventure. We were at a party, and he said, “You know what I really like about you?” And I said, “No.” And he said, “You’re one of the few guys that I ever saw on CNBC who said ‘I don’t know’ so many times.” He goes, “One time I was watching you, and you said ‘I don’t know’ maybe three or four times.” And he goes, “I turned to my wife and I said, ‘I trust this guy.’”

Derek Sivers
Nice.

Jim O’Shaughnessy
Because we all feel so compelled, right, to have an answer. Right, right? And for the most part, Derek, we don’t know yet. The honest answer, if you’re going to be completely candid: “I don’t know. We’ll see.”

Derek Sivers
Do you think it’s related to this? The stereotype of the quiet person that’s sitting at the table full of opinionated people, that hasn’t said anything the whole time, and then when they do speak up, we pay attention, because, “Oh, really? Now they’ve got something to say?” I think pretty universally across the world, people admire the person that only speaks when they’ve got something important to say. But isn’t it interesting that the algorithms reward content creators that spew constantly, whether there’s something to say or not? And I, of course, rebel against that idea. So that’s why people on my mailing list... I have an email list. One of the problems is, if I don’t have anything to say, I don’t say anything. So sometimes they don’t hear from me for 10 months, and then I send out the first email in 10 months.

And sometimes people go, “Who are you?” Like, “Oh, you signed up to my mailing list a year ago. Sorry, I had nothing to say for the last 10 months.”

Jim O’Shaughnessy
You know, I find that is inconceivable to me. It would be inconceivable that you would have nothing to say for 10 months.

Derek Sivers
Well, nothing public to say. I don’t know. I’m still working on my stance on this, but, you know, there’s a bunch of stuff, like I brought up earlier: “I don’t know. Should I move to China? Should I move to Bangalore? Should I start a company in China? Should I do this?” Decisions around building my house. I mean, there’s obviously lots going on in my head the last few years, but it just didn’t feel like it had any public value. You know, it felt like it was all just really internal stuff, and I hadn’t yet distilled or extracted some universal life lesson from it.

Jim O’Shaughnessy
Yeah. Well, and, you know, I was thinking about it too. We are a lot alike in so many regards, but if you have a company, like I do and you did, where you had employees, it can make it a challenge for the people who work for you. By that I mean they’re seeking direction, they’re seeking stability, right? And I’m willing to pivot on a dime, and a lot of people really resist that. And so I wondered, maybe I’m just a horrible leader. Because in many respects, who gets elected, right? And this isn’t just a phenomenon in the United States. It’s kind of everywhere. The person who gets elected is the one who seems the most certain. He or she is the one who... “Yes, of course we’re going to do this and this. This is my programme. And I will never back... I will die on that hill.” Again, I was talking with my colleague earlier, and I personally take the George Patton view of: I want the other poor dumb bastard to die on his hill.

Derek Sivers
Nice. I hadn’t heard that. I like that.

Jim O’Shaughnessy
I don’t want to die. Every time I see “I’ll die on this hill,” I’m just like, “Oh, what a waste. Why? What if you’re just completely wrong?”

Derek Sivers
I like that. You know, if I could do it all over again: at my last company, I was also a bad leader. And I’ve thought a lot about this. I was experimenting and exploring, but still, quote unquote, leading. Okay, sorry. I picture the classic 1800s British explorer with the pith hat on, going in with the machete into the jungles of Africa to go to some land that the British had never been to before. And that’s all about the exploring, right? “Let’s go up here. Let’s try this. Oh, let’s go in that. Oh, that’s a cave. Let’s... no. Okay, we’ll come back out of that. What if we go up here? Nope, that’s nothing. What if we go over here?”

So you and I have an exploratory approach to life, which is fine and wonderful and valuable and fun, but what a pain in the ass to follow an explorer. Imagine the troop of people carrying the chests, following that British explorer into every little crevasse and then back out again. “Oh, no, that’s quicksand. Reverse.” But the way I think it would happen is that explorer would find a great harbour through, you know, exploration number 97. He finally finds something valuable, and so he notifies the Queen: “Hey, we found a great harbour. I think this would make a great port.” So then the Queen appoints a bullheaded leader with blinders on. He goes, “Right, we’re going to that port. Here’s why. Here’s the benefit. Here’s the outcome. Here’s where we’re... let’s go.”

And it’s a straight line that’s easy to follow.

Jim O’Shaughnessy
Yeah.

Derek Sivers
So whereas it was a drag to try to follow the explorer, it’s actually kind of fun to follow a straight-line leader. You know exactly what you’re in for. You know exactly where you’re going. No surprises. Hey, it’s like that certainty-uncertainty thing we talked about, right? Most people want more certainty. So you get a lot of certainty by following the straight-line guy. And then he just goes straight to that harbour and sets up the port there. That’s it. If you tried to say, “Hey, you know what, what if we tried going this way instead?” he’d say, “Shut up.” Yeah. Okay. Now, in hindsight, if I could do it all over again, knowing that I have an explorer, experimenting personality, I would keep my explorations and experiments private. I would not tell my staff about them, because your staff are not your friends.

I mean, even if you’re friendly, they’re not... you know, there’s a conflict of interest.

Jim O’Shaughnessy
Yeah. The agent principal problem.

Derek Sivers
Right. So I would keep my explorations private. And only when I had, metaphorically, found a harbour that could be a great port, then I would publicly play the straight-line leader to my staff and say, “Everybody: made a decision. This is where we’re going. This is how to get there. This is why. This is what you can expect at the other end. It’s a straight line. Let’s go.” I would have to delineate that side of myself. Yeah, I’d make straight lines for my staff to follow.

Jim O’Shaughnessy
Yeah, I did that ultimately with most of the companies that I founded, just because it worked, right? It works much better. It didn’t stop me from being me and doing all of the above. And I didn’t keep it entirely private, let’s be honest. I shared it with several of the people I knew who could handle it. But yeah, that was one of the things that I learned. And then when you put it on yourself, well, of course you don’t want somebody up there: “You know what we’re gonna do? No, wait, no, we’re not gonna do that. Wait, hang on. No, actually, we’re gonna...” You’re gonna go, “Get the fuck out of here, man.”

Derek Sivers
“I read this interesting book last night. What if we tried this?” I get the feeling you’re laughing out of recognition, because, yeah.

Jim O’Shaughnessy
Oh, totally. Recognition.

Derek Sivers
I did that too. It was literally like I read the book Maverick and I was like, “Hey, what if we had profit sharing?” “What if we just split up the company equally between the number of employees? I just read this book last night. What if we tried that?” And like two months later, I’m like, “Never mind, change my mind.” They’re like, “You fucking asshole. You asshole. You told us that the company was part ours.” I’m like, “It was a good book.”

Jim O’Shaughnessy
I changed my mind.

Derek Sivers
Changed my mind. There was nothing... that was quicksand that way.

Jim O’Shaughnessy
The other thing that we talked about last time was the barcode biz. And essentially, just to refresh your memory and our listeners’ memories, that is something that can be very difficult for an individual to do. In the instance of our conversation, it was musicians and barcodes, if I’m correct. But when somebody comes together and collectivises, it becomes very easy for that individual to get what they need. What do you see today as a barcode opportunity?

Derek Sivers
Ooh, I’m biased, because it’s the thing I was literally working on yesterday, this morning, and today after we hang up the phone: my page called Tech Independence. I don’t know if you’ve seen this. The URL is sive.rs/ti, as in Tech Independence. For 30 years I’ve had a very anti-corporate approach to technology. I kind of... I have a punk approach to this. Very anti-business. I hate it when big businesses try to turn tech into something very corporate and over-engineered and awful, full of formalities. Oh, to me, the spirit of the mid-90s, the brand new World Wide Web invention, was this rebellious...

Jim O’Shaughnessy
Punk rock anarchy.

Derek Sivers
Yes, it was, it was like punk tech.

Jim O’Shaughnessy
It was amazing.

Derek Sivers
And so I want to keep that punk tech approach. I like it, and I think a lot of people don’t even know about it. They don’t even know that this is a possibility: to take a punk approach to tech, and to use it as the antidote to the corporate formalities that you’re usually surrounded with. So Tech Independence, at a shallow level, is just teaching people how to get off the cloud. How to delete your Gmail account and run your own mail server. How to delete your Dropbox account, because you just don’t need that if you have your own server. Just get your own domain. It’s 5 bucks or 15 bucks to get a domain. Point it at a server that costs you a few dollars a month.

Here’s how to run your own server, so that all of these, quote unquote, “we’ll do it for you” services can be kicked to the curb and ignored, because you can do it all yourself with a little server for $4 a month. So I ended up writing all of these instructions onto a page on my website called Tech Independence. And version one was a long, detailed “Do this. Here’s exactly what to do. Type this, go here, click that, copy, paste this, put this into the command line. Now make your SSH keys and do this.” And it was like a hundred steps. But if you follow these hundred steps, you’ll have your own server. Version two was me putting 50 of those steps into a script that you could run on your server.

So now it’s 50 steps, and copy this script and just run the script, and it will set up your mail server, your web server, your con... your calendars and contacts. What else? Your Dropbox-style file thing. Anyway, just the last two days I’ve been working on version three, which is taking care of even more of it for you, but giving more education at the same time. So the script will do it for you to save the typing, but it will also give you a plain-text description of what we’ve just done, to copy and paste, so that you can paste it into an AI now and say, “I am running OpenBSD 7.9, using relayd and the HTTP server. I’ve got an SSH account that’s locked in for my user only. The server is hosted here. I have root on this server. And now my problem is that the SMTP mail server is not relaying mail.” So it lets you copy-paste some context for your situation. And then you could ask the AI to either solve the problem, or even, “Can you teach me some more about what I have just created?” Because all I wanted my Tech Independence script to do is to quickly give you the experience of having your own server. I didn’t want to lay out a hundred different options. It’s just very paint by numbers. Go exactly here. Go to vultr.com, get a domain. We’re going to set up the OpenBSD 7.9 server. We’re going to use this web server, this mail server, this concert calendar... I keep saying “concert” by accident. I mean contacts and calendar server.

And just, bup-bup, do exactly this, and within minutes you will have your own server, so that you can be tech independent and shut down your Gmail and whatnot. But I also want people to understand what they’ve done. So I think it’s interesting that AI can make us more dependent on it if we’re not careful, but it can also make us more independent, because with the exoskeleton of AI to strengthen our abilities, we can replace things like Gmail, or replace things like Dropbox, that we were previously dependent on. You can learn how to set them up yourself.

Jim O’Shaughnessy
Yeah, I like that idea, and I completely agree with you. I have this idea that almost everything is a dual use, right? Like, you know, we discovered fire. Amazing, amazing things fire did for us. We started to cook our meat and we got the prefrontal cortex that we hadn’t had before, and that was, yeah, yay, prefrontal cortex. But fire is also incredibly dangerous, and used the wrong way can be incredibly destructive. We didn’t ban fire. We invented fire alarms, fire departments, fire warnings, fire extinguishers, fire everything. And so whenever I hear either of the extremes, right, like, “No, AI is going to bring us into a utopia”... no, it’s not. Nor is it going to turn us all into paper clips, right?

We will learn. When bad things happen (and bad things will happen; they happen with any new and powerful invention or technology), we will learn. “Oh, huh. We better put up, you know, much more of a strong firewall, so this can’t just escape through from its sandbox.” And so I definitely agree with your notion that, depending on the way you use it, it’s either going to dumb you down, because you’ll just say, “Oh, all I got to do is press this button and I get everything I want,” or teach you. And all of a sudden you take all of these... Ken Stanley wrote a great book called Greatness Can’t Be Planned. And he basically talks about the fact that once you get to a certain place, you see things differently, obviously, right?

Because you’re changing your location, you’re going to see things differently and experience things differently. And when you get to that new space, it’s good that you see things differently, because you’re like, “Well, I had intended to go up there, but now I see, oh yes, that’s very inhospitable up there. There’s a lovely meadow over this way. Let’s go this way.” And so I think something where people, like you’ve just described, can use it in a fairly easy-to-use manner, but also learn... Oh, because guess what? The minute you learn that new thing, you’re like, “Hey, wait a tick. I could also do this and this.” And that’s how you grow. That’s how you get new things. Thank God for the tinkerers, in my opinion, right? Because... yeah, no, go.

Derek Sivers
And it’s also just so fun. I’m so glad that you could relate to the punk tech thing I said earlier, because what I’ve had so much fun using AI for lately is to teach me how to replace the bits where I was still dependent. So, okay, since you said the tinkerers, that’s why I had to interrupt here. Imagine this. You have a domain name. Is it osv.llc, right?

Jim O’Shaughnessy
Yeah, that’s right.

Derek Sivers
Okay, so osv.llc. You registered it somewhere, at a domain registrar. And DNS is the name of the thing at the registrar that makes it so that when somebody types osv.llc in their browser or their email client, it knows to send the web traffic to IP address number 123.45.67.8, and to send the email traffic to mail.google.com, or whatever you’re using for mail. So that’s called DNS. And I’ve been online for 30-something years, and I’ve always just used the DNS that was built into my domain registrar. So recently I started moving my DNS to a separate DNS server called bunny.net, which I was very happy with. It’s a company out of Slovenia. I’m very happy with them. They’re great.

But along the way I said, “But I’m still using some external company to do this thing. It’s just low-level tech. How hard could it be?” So I was like, “Dear ChatGPT, teach me how DNS works and how I can set up my own DNS server.” And so it guided me towards creating something that is actually more secure than using some other company, which is called the hidden DNS master. So on a private server that has nothing pointing to it, that’s secret, but at a data centre, I built my own DNS server. Sorry, I’m using a standard, secure OpenBSD DNS server, but basically it’s super low-level, doing it myself, running the same software that these other providers run, but I learned how to administer it myself. So now, for all of my domains, I am the DNS master.

And then I use a company called ClouDNS that just pulls from my master, and they’re like the public CDN, firewall type thing. So the public gets it from them. But I’m the sole source of DNS, so doing it this way, it’s actually way more hack-proof. Worst-case scenario, if somebody hacks into my account at ClouDNS, I go... it’s just a shrug, because I’ve got the secret hidden master that nobody can get into. So that was an interesting low-level thing to learn, because along the way I learned how DNS is working at a very low level. And it was so educational. Same thing with running your own mail server, running your own web server. Instead of just going, “I don’t know, it’s at WordPress somewhere,” you can have the AI... “Hey, show me at a very low level how I can create, like, a hello world type basic service here, and do it myself.” And what I love the most about this (and I just found that I was elated for days while I was working on this) is that it is so non-commercial. I’m just there in a black terminal with the code, and nobody’s pushing, you know, upselling at me, or whatever. It’s just so beautifully non-commercial that it reminds me of that punk tech joy that I got out of this in the first place.

Jim O’Shaughnessy
I love it. I love it. You know, as far as the whole punk thing goes, I look at the scientific method as kind of pure punk rock anarchy. And by that I mean, take no one’s word for it. “No, no, that’s not the correct answer. I think there might be a better answer, and we’re going to keep looking until we find a better one.” I think that it’s a function of just the insatiable curiosity which... back when the whole Age of Reason began, the Enlightenment, there was this thing called the Republic of Letters. Are you familiar with the Republic of Letters?

Derek Sivers
No.

Jim O’Shaughnessy
So it’s really cool. Back in, you know, the 1700s, educated people all around Europe were discovering all these interesting things, and they would write very long letters to one another that got passed on. What would happen is, I would write you a letter and you would think, “Oh, this is a pretty good idea. Oh no, Jim really screwed the pooch on this one. This is not a good idea.” And you would annotate. You would say, “Derek here. No, I don’t think this one works, and here’s why.” And the one you liked, you’d say, “Yes. And what you forgot to mention was this.” And then you’d forward that to another friend who also had the interest. This was a real thing, and that’s how a lot of the news of when calculus, for example, got invented... You know, Leibniz was saying, “I invented calculus,” and Newton was saying, “No, I invented calculus.” And part of that controversy was because all these people were sending letters back and forth to each other. “See what Newton did?” “Well, yeah, but did you see what Leibniz did?” And so that was this explosive, almost Cambrian-like explosion of knowledge, from this interaction in the Republic of Letters. And then the Royal Society institutionalised it. Institutional capture. They formed the Royal Society. And guess what? Societies that want to go on and have authority and all that, well, they’re going to have a lot more rules, they’re going to have a lot more protocols, they’re going to have a lot more “This is acceptable. This style is not acceptable.” And it’s not that at that time it fell off a cliff.

But much of, say, peer-reviewed science today, it’s just so incremental. It’s so... “Are you kidding me?” And so I think that the true scientific method is very much of the ethos that we’re talking about here.

Derek Sivers
I love this. I’d never thought about that, but I think you’re so right. And Richard Feynman is so punk.

Jim O’Shaughnessy
My favourite physicist.

Derek Sivers
But think about it. He was really outspoken in saying, like, “I don’t care who you are. I don’t care what your degree is. You verify your work against the experiment. Show me your work. I don’t even care how beautiful your theory is. Do the experiment.”

Jim O’Shaughnessy
That’s all. If your theory is the most beautiful theory in the world, it’s more elegant than any theory that I’ve ever seen in my life, and the facts say it’s wrong, it’s wrong. Get over it.

Derek Sivers
Yeah. You know, I’ve tried... I want to dive into this punk subject. Anybody listening to this, if you please, email me if you have any insights into punk philosophy. Because whenever I’ve tried to look into it, I just keep getting steered into punk music. And I’m like, okay, well, I don’t like the music. I like the ethos, the ethics, the mindset, the rebellion, the something, the lack of formalities. And I love that you just brought science into this. Science as punk. That’s a beautiful example.

Jim O’Shaughnessy
Yeah, because it is. And that’s what true discovery is. And, you know, whenever you get an institution that wants to capture attention, wants to capture value, wants to capture all of that sort of stuff, a lot of that fun stuff, the stuff that got them there in the first place, stops happening. And that’s a mistake if you want to forever learn more, expand more. You know, I’m a huge fan of David Deutsch. I don’t know if you’ve read his book.

Derek Sivers
Yeah. Okay, wait. You know what? We’re deep into the podcast. Who knows if you... I dated his goddaughter in Oxford. And so every night after our dates, I would drop her off at David’s house. And so...

Jim O’Shaughnessy
Oh, my God.

Derek Sivers
I didn’t meet him, because we broke...

Jim O’Shaughnessy
Not an envious person by any stretch of the definition of the word, but that makes me envious.

Derek Sivers
I just assumed that... I thought we were going to keep dating. I liked her a lot. I thought we were going to keep dating, and I just assumed that I would meet him. But then we broke up and I didn’t meet him, and then Covid hit and that was that. Another reason I loved living in Oxford. Sorry, I just have to smile with sweet memories when I hear the name David Deutsch.

Jim O’Shaughnessy
His book The Beginning of Infinity is a sort of a definitive look at how I look at the world.

Derek Sivers
Nice.

Jim O’Shaughnessy
I read it when it came out in ‘12, and then I reread it in ‘23 or ‘22. I can’t remember. I got so much more out of it the second time.

Derek Sivers
Oh, good. I should read it a second time. I really also loved it the first time.

Jim O’Shaughnessy
It’s worth the second read. Let’s do something fun. I’m going to put you on the spot, for once.

Derek Sivers
Okay.

Jim O’Shaughnessy
I love the fact that you take... I am, right now, just to give you context, I am writing... I’ve written four books, but they’ve all been non-fiction books. So I thought, you know what? I’ve always wanted to write this, and this is true. I’ve always had this idea for a fictional thriller-type novel, for the last 35 years, and now I’m writing it. And the first thing I learned was fiction’s got hands. By that, I mean it’s a hell of a lot harder than non-fiction. And I always admired you for the care you gave each sentence, right? You would write a sentence and then you’d write it 10 different ways. Can I put you on the spot?

For our listeners and viewers, give me a sentence, and then show me all the ways that you got to that sentence from other ones. If you could do it from memory.

Derek Sivers
Ooh.

Jim O’Shaughnessy
Because you’re so good at this.

Derek Sivers
I wish I could. I don’t remember the final sentence. Damn it. In my book How to Live... I just don’t have it right here, man. If I was one of those guys that... if I was sitting at the computer while we were talking, I would just pull it up. But okay. But I remember there was this one idea that was a combination of something I read in a book, that then was combined with a conversation with a friend, and then enhanced by a conversation with a different friend. And all these sources together had this big idea. Kind of like you and I have talked around a few ideas, like straight-line leadership, or punk tech, or the scientific method as punk. We’ve talked around an idea.

But for my book How to Live, I was writing so succinctly, like poetry, that I just kept... I took a paragraph and made it four sentences, and I took those four sentences and made it three. And I took those three and I made it two. And then I took that two and I made it one, but it was still too long. And I cut out all the unnecessary words. And finally, what I was left with was this one sentence. It was like ten words. And I looked at that going, “God damn, that really does sum it up.” What a nice feeling. And even the choice of words: I’m constantly reading things out loud and choosing the words that sound nice in the mouth, that roll well off the tongue.

Because ideally, I still have this songwriter in me that wants things to be catchy. So with my newest book, Useful Not True, the goal was to make it so catchy that, in theory, if I were to practise for just, say, a few weeks, I would be able to stand up on stage and, word for word, tell you the whole book from memory. Because it’s only 88 pages. The average chapter length is 22 sentences. And I should be able to memorise that book word for word, and stand on stage like one of those people that puts on a one-man show on Broadway. I should be able to do that book word for word.

And, audience, we paused for me to go find the sentence that I was so proud of: “Pain’s power relies on surprise. If you expect it, it’s weaker. If you choose it, it’s gone.”

Jim O’Shaughnessy
Wow.

Derek Sivers
It just made me so happy. That was, like, hours of conversations and rambling ideas. Yeah. “Pain’s power relies on surprise. If you expect it, it’s weaker. If you choose it, it’s gone.” And that’s in the context of the chapter called “Pursue Pain”. So the whole idea is, if you decide to deliberately follow the painful path, because you know it’s better for self-improvement, or learning, or greater rewards, then the pain is gone, because you’re choosing it.

Jim O’Shaughnessy
It’s like Jung saying that as long as you try to fight your demons, you will only strengthen them.

Derek Sivers
Oh, and Oscar Wilde said, “The way to resist temptation is to yield to it.”

Jim O’Shaughnessy
Yield to it. I love Oscar Wilde.

Derek Sivers
Yeah, he’s always good for the classic quip like that, reversing the expectation of the line. But, I mean, so, writing fiction: are you following any structural best practices, like an outline that they say makes a great story? Or are you just fully immersing in the...

Jim O’Shaughnessy
I read Joseph Campbell at length. I read a lot about how to write good fiction. I have kept journals forever. I’ve been a writer all my adult life, so... But I’m not following the hero’s journey. I’m immersing. I’m immersing after having read, or in many cases reread, those books. And I figured, since we have the publishing company, I’ve got an amazing group of writers working for me. So we’re also using a writers’ room, and we’re putting AI editors and writers in the writers’ room. We want to give the whole thing a whole different take. We’re going to try a very different way to get a really cool story. And it’s been ridiculously fun, because when you start, you’re just an idiot. I would have my colleagues say, “Well, what do you think of this?” And, you know, they try to be nice. It’s like, “Well...” So what I finally did... we also have our own AI stack. We have our own hardware, our own software, everything. And so it’s not nerfed. It’s much more helpful than some of the commercially available ones, because you’re not lobotomising it. Anyway, what I found the AI was best at was actually criticism. So I would put a chapter in, and it would give me all the pluses and minuses. And then I’m like, AI is... even our own AI is a bit sycophantish. So I wrote a very long prompt that created one of the best-educated, most erudite critics, who is going to hate every chapter that I write. And Derek, I gotta tell you, that was the best of any of the feedback I got. Because it was vicious. It was beyond vicious.

And at first, you don’t get mad, because it’s a machine.

Derek Sivers
Yeah.

Jim O’Shaughnessy
If a human being that you were fond of sat opposite you and said those incredibly vicious things, you would be so hurt that you just couldn’t function, right? When it’s a machine, you just read it. You’re like, “Well, that’s kind of picky. That’s kind of...” Then you read it again, and then you’re like, “It’s absolutely right. I’ve written this character completely in the wrong tone. I’ve got to completely rethink the way I think about this.” And then it just started getting better and better. So my vicious critic prompt in AI proved to be, like, the absolute best feedback I got anywhere.

Derek Sivers
I love this. I wonder how the AIs... I could totally imagine them having the structure frameworks in mind. I’ve never written fiction, but I find it fascinating. I’m a film buff. I didn’t even realise this about myself until a film composer told me what a film buff I am. I’ve read maybe three or four of these books now that talk about story structure and film structure, and how to make a plot that keeps you hanging and keeps you involved and makes you feel like you’ve arrived in a different place than where you started. And who is the protagonist? The protagonist is the one that changes the most. You know, things like that. And I find them fascinating, even though I’ve never used them. But I have written over 120 songs with the same approach. You could call it formulaic, but it’s taking the lessons from what have made the best songs so good, and using those techniques to write your own song, using them as inspiration. And so my favourite phrase about this is “Restrictions will set you free.” If you’re just given a blank page and someone says, “Make something. Go,” you’re stuck. But if somebody says, “Okay, start here, then after this change to that, but then double-time it in the middle, and then go to this, and then end higher. Use these three instruments and these six notes. Go.” Well, now those restrictions set you free.

Jim O’Shaughnessy
Absolutely.

Derek Sivers
Because now you’ve got so many ideas sticking within the structure. So if I was to write fiction someday, I think I would probably get so inspired to write, like, 10 different stories using some given framework, that ideally nobody would see the framework underneath.

Jim O’Shaughnessy
Yeah, definitely. And I’m lucky, because we’re using this writers’ room approach. I have some great people for structure, just as you’ve been outlining. And they’re reading it now, and they’re like, “Okay, what you... you had a... the cortisol spike. That’s a thriller. And then it spiked again in a different thing, and it’s the same chapter. No, no, no, no. You got to let each of those spike independently. You got to make this two chapters, not one.” And basically, I was saying the same thing, except in one chapter it was two cortisol spikes, and that was somehow less jolting than the big one in the first chapter and the big one in the second chapter. So I’m very lucky to have a very talented team that can give me that kind of feedback.

But it’s fun because, you know, it’s something that I had wanted to do since I was in my mid-30s, and now I finally got a chance to do it, so that’s exciting.

Derek Sivers
I love this.

Jim O’Shaughnessy
Another thing you did for your book Useful Not True was you studied philosophy for two years, and I love that. I love philosophy. I took a few classes in it, but I’ve read most of the major philosophers. And what I wanted to ask you is: after you studied the philosophy, what could you be confident in saying... that you were fairly confident of an idea before you started studying the philosophy, and then after you did, you’re like, “Yep, that one doesn’t work at all”?

Derek Sivers
I actually have an anti-answer for you, because it made me less confident about my definition of true. I’m still a little surprised that I only agree with the nihilists. And nihilism has such a bad name. It’s used as almost synonymous with Satanism or something. When people say, “Well, you don’t want to be a nihilist,” you know, they just use that as the worst thing that anybody could be. But there is a beautiful little book called Nothing & Everything. Actually, sorry, the first half of the book is beautiful. The author uses a pseudonym, Val N. Tine. And the book is split into two halves. I don’t know what happened in the second half, but the first half is so beautiful and so well written, and just had me yelling out loud as I was reading it, like, “Yes!” And then it’s like, “Part Two,” and I’m looking at this, like, “Ew, what spilled on the page here?” Anyway. But this definition of true that I find most useful... because of what you said earlier, your biggest problem is other people’s certainty. When they get so damn certain, their mind is closed. “That’s it. This is a finished matter, not up for discussion. That’s it.” To me, you should reserve that only for things where there really is no other answer. A square has four sides, and that’s that. There is no other answer. That’s certain. That the sun is going to come up tomorrow, you know, like you said...

Jim O’Shaughnessy
Highly probable.

Derek Sivers
Not certain. Let’s reserve the things we call true for only the things where there is no other answer. And unfortunately, even pragmatism, which a philosophy professor steered me towards... I described it to her, and she said, “It sounds like you’re talking about pragmatism.” So I went and read five different books about pragmatism, and unfortunately, no. I wish that my thoughts would have fit into the philosophy called pragmatism, and I would have said, “This is the school of thought I subscribe to.” But no, it also wasn’t quite right. So, sorry, the only answer to your question is that it made me more uncertain. Which I guess was ultimately my point. I think that Useful Not True is ultimately a book about scepticism. It’s about doubting everything.

Jim O’Shaughnessy
Well, sure. And I wrote a thread on Twitter about my own journey there. And I said, when you go through all of the thinkers, the philosophers, et cetera, most people end up at nihilism. And one of the things that I learned, at least in my life, was you’ve got to walk across the bridge of nihilism. And by that I mean, you get to the other side and you realise, if life has no external inherent meaning, if there is no truth with a capital T, how lucky are you? You’ve got a blank canvas. You can paint your life on that blank canvas. You can make an incredible life, with meaning, with purpose, with all of those things that you decide. It’s entirely bespoke to you. But you gotta walk across the bridge.

Derek Sivers
I love that. You might, you know, even just for the smile and the joy... I don’t know if it’ll teach you anything, but this little book called Nothing & Everything, by...

Jim O’Shaughnessy
I wrote it down. I’m gonna get it.

Derek Sivers
Okay, good. And just stop at the second half. When it gets to the second half, just call it done. But yeah, it’s the only book I’ve ever found that fully dives into what you just said.

Jim O’Shaughnessy
I just love talking to you. I hope I can hooks you on yet again, because I didn’t get to half the things I wanted to talk to you about. You are such a wonderful conversationalist. I always really enjoy talking with you. It’s just so much fun. A lot of people... I don’t know if this happens to you, but a lot of people sometimes look at me and they’re like, “What?” Yeah, we’re weirdos. Yeah.

Derek Sivers
I think last time, didn’t we do a Part One and Part Two right away? So I’d be up for that, if you’d like to.

Jim O’Shaughnessy
Oh, I would love to. I will have Ena send the invitation for the second one, and we’ll get this one out as quick as we can.

Derek Sivers
All right, audience, we’ve just turned this into a Part One, Part Two to be continued.

Jim O’Shaughnessy
Part One, Part Two to be continued.

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This summer in Naples, Brent’s team presented results from three sealed Herculaneum scrolls, including the first read end to end. Their announcement was covered everywhere from National Geographic to NBC News to The Guardian.

Brent and his work are the subject of The Vesuvius Challenge, an upcoming documentary from Infinite Films and Scott Free, in partnership with Calliope Pictures, narrated by Guy Pearce.

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

Spotify

Apple Podcasts

Show Notes

Brent Seales & Nick Tawil

• Dr. Brent Seales: Stanley and Karen Pigman Chair of Heritage Science at the University of Kentucky and co-founder of the Vesuvius Challenge. Brent Seales at the University of Kentucky

• Vesuvius Challenge: The open competition Brent co-founded with Nat Friedman and Daniel Gross to read the carbonized Herculaneum scrolls. Vesuvius Challenge

• The June 2026 breakthrough: The announcement in Naples of new texts, titles, and authors recovered from the scrolls. The day the Herculaneum scrolls began speaking again

• Nick Tawil: Guest host and head of Infinite Films. Connect with Nick

The Scrolls & the Discoveries

• The Herculaneum library: Roughly 1,800 scrolls carbonized by Mount Vesuvius in 79 AD, the only library from antiquity that survived. Vesuvius Challenge: the scrolls

• Philodemus, On Gods, Book 8: A title and author read from a sealed scroll, establishing that the work ran to at least eight books. CNN on the discovery

• The En-Gedi scroll: The burned Torah scroll Brent’s team read without opening, containing one of the oldest known copies of the first two chapters of Leviticus in the canonical Masoretic text. Vesuvius Challenge on En-Gedi

• The $1 million prize: The open competition to fully unroll and read one of the remaining sealed scrolls. Current prizes

Films & Coverage Mentioned

• The Vesuvius Challenge: The upcoming documentary from Infinite Films and Scott Free, in partnership with Calliope Pictures, narrated by Guy Pearce. Deadline announcement

• Secrets of the Dead: The Herculaneum Scrolls: The PBS episode following Brent inside the Villa of the Papyri. Watch on PBS

• Cost of Glory: The Roman history podcast Brent and Nick reference while discussing what might still be buried. Cost of Glory

• Dead Poets Society: The source of “carpe diem,” one of the two ideas Brent would give the world. Dead Poets Society

Highlights

Why Brent Launched the Vesuvius Challenge

The acceleration that we were going to get from just going open source was going to far exceed... it was going to far outpace our own ability to just get there. And what everybody wanted was to just solve the problem. It wasn’t so much about owning it or getting sole credit. It was really about delivering these things back to humanity. And we thought that we were right on the edge of being able to do that. And so I think the excitement of being able to get over that cliff, that marker of being able to say, “We’re going to do this,” that put us over the line we needed to be over to be able to say, “Okay, it’s worth opening this up.”

The Authors Are Coming Alive

So I feel like my part... not that it’s completely done, but it’s substantially done. We achieved this moment. And now the people who can read the language are not talking about the technology anymore. They’re talking about reading language, understanding the world. So I think there’s been a kind of change where I’ve completed the technical work, substantially complete, let’s say, where I don’t have to make the case anymore that this is possible. And of course, we’re going to refine the methods so that everything can be faster, everything can be better. But the conversation now is really about the works themselves, and the scholars who can read those works, and what we’re going to learn from the ancient world. You know, until the tech worked, we weren’t learning anything about the ancient world. We were learning about synchrotrons and virtual unwrapping. Now we’re actually reading the words, and the authors are coming alive. And that’s an amazing and a remarkable moment.

Edited Transcript

Nick Tawil
Hey, Brent. Good to have you here today. It’s so good to see you in person again. You’ve been incredibly busy and productive this summer. You are in the news literally all around the world, certainly here in the United States, but also in Italy, Germany, England, France, for the work you’re doing at Herculaneum in Naples, Italy. We had a big June announcement.

I’m privileged to know a lot about this because, you know, O’Shaughnessy Ventures, we’re literally doing the film on you guys. It broke on Deadline a few weeks ago. But I wanted to start my time with you now with an excerpt from an article in Scientific American.

So here it is: “How do you read a book you can’t open? That’s precisely what Brent Seales, a professor at the University of Kentucky, has spent his career trying to figure out. And on Thursday, his life’s work reached a pinnacle. Seales, alongside a huge group of volunteers and scientists working as part of the Vesuvius Challenge, has helped develop the technology to see inside books and scrolls that we can’t open without destroying them.”

Now, use the word... “Your life’s work has reached a pinnacle.” So I don’t think that’s hyperbole. I also don’t think it’s hyperbolic to say that what you’re doing here, and what you’ve been able to do with AI and the X-ray tech that you’ve devoted your entire career for, is probably a watershed moment for understanding our own civilization and our own history, our own civilizational history.

So I guess just to start, how has the summer been? And how has your work changed even in the last couple of months, just in terms of attention you’ve gotten around this? And I want to talk about the actual discovery as well.

Brent Seales
Well, thanks for that introduction. What a great piece. It is astounding, and to hear it read back... you know, every time we think we’ve found a pinnacle, there seems to be a new place. And this summer has been fantastic. The June press event in Italy kind of brought it all back home because, you know, we’re standing there talking about reading these scrolls for the first time using virtual unwrapping, and we’re looking across the bay at the actual volcano. And the time scale is crazy, right? 2,000 years. So it was a very high moment.

And we’ve had a series of those over the last five years. In fact, in 2020, which was the anniversary of the Apollo moon landing, I proposed to my research team, “This would be the year.” And you know what happened in 2020. Soon after those words came out of my mouth, the entire world, you know, goes upside down.

So from there really to now has just been this constant climb, and to get to the top... I mean, I think you’re right that the word “pinnacle” kind of captures being pretty high on this mountaintop of having solved the problem, and turning from the technology really more toward the lost voices that we’re restoring by reading these manuscripts. It’s amazing.

Nick Tawil
So talk to me about where these manuscripts actually live in Herculaneum and how many there are. Give me a sense of scope and scale.

Brent Seales
Sure. I did not know about this collection as a student, and it wasn’t until we started developing this particular technology that I started searching around for likely candidates. And Herculaneum came to the top immediately because it’s iconic. I mean, it was formed... The library at Herculaneum was formed by the volcanic eruption of Mount Vesuvius in AD 79.

Most people are familiar with the story of Pompeii. Pompeii is maybe the birthplace of modern archaeology, and it’s also this fantastical ancient lost city that was uncovered by humanity. Well, the reason why it was lost is the explosion of Mount Vesuvius.

What’s unique about Pompeii is the architecture, the scale and scope of the city. What’s unique about Herculaneum, which is where the scrolls were found, is that it’s the only library from antiquity that survived. We have all the history in the medieval copies of written material that tells us there was a library at Alexandria. People were into books. Books were traveling around the ancient world. But we don’t have any of the actual libraries left, and this is the only one.

So you’re talking about 1,800 scrolls, maybe a couple thousand books. They were all discovered in the realm of 1750 to 1760, when the Herculaneum site was first excavated, and many of them were badly damaged at excavation. But because they were being excavated by the royal family, King Ferdinand and others who were reigning in that part of Italy at the time, they were carefully kept. Some of them were gifted to other kings as diplomatic gifts, but for the most part, the collection stayed in Naples, and from 1750 until now, we have what we have.

And the state of affairs is that the scrolls were badly carbonized, which means that the volcano spared no expense in basically turning them into what looks like charcoal. So you have the only ancient library that is in existence in the world from antiquity, and then you have this profound physical problem that you can’t really unroll or very easily read any of the material.

Nick Tawil
So over the years, the easier scrolls were read and have been read and researched, but there’s just an entire portion that’s unreadable. And so that has basically stayed untouched until now.

Brent Seales
Yeah, absolutely. The ones that could be opened were. Some of the ones were pretty readily able to be unrolled. The volcanic ash and mud that covered up the library varied in how it impacted the collection. So early on, you had some that were just immediately opened. You have a lot of them that were destroyed because as they opened them, they just scraped it away and they made sketches, and now all we have are the sketches. The worst of the worst are the ones that remain. And for some reason, I latched onto that as the problem.

And I don’t know... looking back, you say things like “your life’s work,” but when your life is playing and you’re doing that work, you’re never really sure what’s going to become your life’s work, right?

Nick Tawil
Yeah. Well, what were you doing before this, before Herculaneum got onto your radar as a challenge? What were you doing before that?

Brent Seales
Well, I’m a computer vision and imaging specialist, and I did my PhD work at the University of Wisconsin in the field of computer vision. Computer vision can be defined as making computers and cameras work together to be able to either imitate what humans can do visually or to solve problems in the world autonomously.

So you see computer vision now every day succeeding with facial recognition, autonomous cars, all of the remote sensing that happens. The early days when I started that work led me into applications like manufacturing, autonomous navigation, space exploration. So I was doing work toward those applications. We were doing welding inspection, for example, where you’d have a camera help you watch a weld being made, and then the control loop would help you improve the process of doing those welds. It doesn’t sound super exciting, and I decided that it wasn’t that exciting for me. So I moved through some of those applications.

The thing I was doing immediately before Herculaneum and a lot of the heritage work that I started doing was medicine. You might be familiar with laparoscopic surgery. This is where surgeons will never actually open the operative field. They’ll do an entire procedure through scopes that have been inserted into the body cavity. And it’s incredibly hard to do that work, so the visualization part of doing that work is super important. So I was working with surgeons to try to help them better visualize not only the operative field live as they were doing the surgery, but all of the preoperative stuff that they were doing. You might X-ray a patient in advance to see what you’re dealing with, and then the surgeon would, what, memorize that preoperative stuff so that they have an idea of what they’re going to face when they go in.

Well, all of those things actually fed into what I eventually started to apply to virtual unwrapping, because the X-ray, right, I hadn’t had a lot of experience with that. But it actually became one of the key things that we’ve used to see inside of these books without opening.

Nick Tawil
And not just any X-ray. It’s, what’s it called?

Brent Seales
Computed tomography.

Nick Tawil
And where are these machines at in the world?

Brent Seales
The medical version of computed tomography is everywhere. Every hospital has one. In fact, tomography won the Nobel Prize in Medicine in 1979. The two inventors.

Nick Tawil
What about the X-ray machines you’re using for this project? You’ve had to travel to use these particle accelerators, haven’t you?

Brent Seales
Yeah, the X-ray for Herculaneum... We’ve settled on a synchrotron, and... that’s a very, very unique X-ray source that comes from a particle accelerator. And there are 40 or 50 of these worldwide. We’ve used a few of them in Europe and in America. There’s one at Oxford. It’s called the Diamond Light Source. We’ve also used one in Grenoble, France. It’s the European synchrotron light source. And what’s interesting about the synchrotron is that it produces a very carefully controlled, extremely bright X-ray beam. And brightness with X-ray means that you don’t have to wait as long to collect the images, because you have so many photons going through the sample that you can take a really, really quick snapshot because it’s so bright. So we can do an entire scroll at very high resolution very quickly.

Nick Tawil
What do you mean, quickly?

Brent Seales
Well, the kind of resolutions that we’re talking about now, which have really unlocked the problem, are kind of astounding. You know, the size of a red blood cell is bigger than the resolution that we’re getting to see the interior of the scroll. Every one of the little voxels that represents the scan of this...

Nick Tawil
A voxel?

Brent Seales
Voxel, which would be the 3D version of a pixel. You add that third dimension, you call it a voxel. The size of that little sample is astoundingly small, and that’s what lets us see everything that’s going on inside the scroll, including the ink.

Nick Tawil
Including the ink. And this is the key. Once you can lift the ink, the ink signature, I’ll say, off of the burnt scroll, then you’ve got something to work with. But it’s still tightly wrapped in this sort of cylindrical form. So now you need to... this is where the virtual unwrapping happens.

Brent Seales
That’s right. The X-ray gives you a model of everything that’s going on inside without having to open it, just like it does on the human body. But it’s still all wrapped up and compressed, and not in a form where you can actually do anything. So all those software steps that take you from that scan to the final readable thing, that’s the thing we invented to be able to do it.

Nick Tawil
And this is the Vesuvius Challenge.

Brent Seales
Well, before the Vesuvius Challenge, that was the research problem, which we essentially had solved to the point where we believed we had the formula. The Vesuvius Challenge took us over the finish line because we threw the contestants in there, broke through on the first-ever scroll, and then with the attention that we gathered and more funding, I mean, we just ran at the finish line after that.

Nick Tawil
And so this is co-founded between you and Nat Friedman. The Vesuvius Challenge is an open-sourced AI engineering challenge, so open source, like, presented and set to the public. Anyone could contribute to this project. And you weren’t really sure what you would be able to find when you opened it up like this. And how did your partners in academia, or other researchers and other lines of work, maybe the papyrologists, how do they all... Were they all involved in this at the very beginning? How did they react to this? Is this just helpful to them?

Brent Seales
Yeah. You know, the Vesuvius Challenge was not a no-brainer for me to jump into. It kind of evolved from an invitation that Nat Friedman sent me to just attend a conference into what became the contest. The conference was the chance where I could meet Nat and his colleagues. And in meeting him, I found out that it probably wasn’t going to work to just ask for investment, because there wasn’t that level of interest in the colleagues that he had gathered together for the meeting. But Nat himself was incredibly interested. And of course, he’s a really smart guy and very connected.

So he sat down after the conference, before I went back to the lab, and he pitched me this idea of a contest. And Nat’s an open-source guy. And what I knew that would require is for us to open up all of our research, including our data. So, yeah, I was sent packing back to the lab with this idea from Nat: “Hey, why don’t you just open up everything you’ve worked on for the last ten years, and we’ll do a big contest.” And you can see that maybe that isn’t a no-brainer, because you have to think, who’s been supporting me? What are they going to think about this? Can I just do this on my own? And maybe I should just do that, maybe just put everything on hold and do it on my own.

But we soon decided, as I talked it over with the folks in my lab, my trusted team, that the acceleration that we were going to get from just going open source was going to far exceed... it was going to far outpace our own ability to just get there. And what everybody wanted was to just solve the problem. It wasn’t so much about owning it or getting sole credit. It was really about delivering these things back to humanity. And we thought that we were right on the edge of being able to do that. And so I think the excitement of being able to get over that cliff, that marker of being able to say, “We’re going to do this,” that put us over the line we needed to be over to be able to say, “Okay, it’s worth opening this up.”

But, you know, I’ll be honest. Once in a while, we’ll see, even now in the press, an article that says a teenage college kid solved this problem. And while that might be true in a sense, it’s also monumentally not true, because we have this whole research program going, and then we had this entire Vesuvius Challenge happening. So all of that is the mechanism that has helped us be able to have that kid do that work.

Nick Tawil
Well, we were also talking about this before. You set up the challenge, and people that contribute to it in a meaningful way do get prize money for it. But what ended up really happening was it became a selection... it became an identity signaling, almost talent recruitment, function for you and your team, because the people that ended up contributing to it ended up becoming a part of the team, at least for a period of time. Correct?

Brent Seales
That’s right. And I love that we got the interest that we got, and I love that it became this huge recruiting tool. A much bigger funnel than I could have ever cast on my own. A combination of Nat’s network plus the notoriety of what happened with the Vesuvius Challenge and just the buzz. You know, we had two, three, five thousand people on a Discord channel talking every day. You can’t even... so many messages, you can’t keep up.

Nick Tawil
This is from around the world.

Brent Seales
From around the world. It’s global.

Nick Tawil
And so it’s still going today, the Vesuvius Challenge.

Brent Seales
That’s right.

Nick Tawil
And you run the team still. What’s the next challenge? Well, first, let’s maybe talk about what happened in Naples this past summer, because I think then the question becomes, what’s next? So tell me about the scrolls that were presented in Naples this past summer.

Brent Seales
Yeah. The moment that we signaled this summer in Naples was that we can do a complete scroll. So you give me a scroll, it’s never been opened, I can make a scan of it, and then the software process is now good enough that whatever’s inside, we can unroll and unwrap and present in a kind of complete way.

So we did that in Naples for three scrolls, and we were able to show also what we found in those scrolls. One is an extensive work of at least 140, maybe 150 columns of text. And I mean, that’s going to keep the papyrologists busy for a long time. This is all ancient Greek. It’s very dense.

Another scroll itself was partial, but everything that’s there we were able to unwrap and read, including the title and the author, which is kind of amazing. And a third scroll also gave us another title and an author, Philodemus, On Gods, Book 8, which means that there were at least eight books on gods by this guy, and no one knew that Philodemus had written those books.

So again, that can start more speculation about what’s in the books, what’s in Book 8 we’re going to read. So we unpacked that in June, and what I think it did is it shifted the conversation now from the technical, because we presented the complete technology that can do the whole thing, to the lost voices that are now going to be restored. So there may be 400 of these scrolls left that have never been read. They’re the hardest ones, and we’re reading them. And that is ecstatic.

Nick Tawil
You’ve gone from pursuing history to now actually reading history.

Brent Seales
That’s right.

Nick Tawil
So there’s a sense of completion now that you have around this project.

Brent Seales
Well, I’ve never been able to read any of the ancient languages because I haven’t had that training. So I feel like my part... not that it’s completely done, but it’s substantially done. We achieved this moment. And now the people who can read the language are not talking about the technology anymore. They’re talking about reading language, understanding the world. So I think there’s been a kind of change where I’ve completed the technical work, substantially complete, let’s say, where I don’t have to make the case anymore that this is possible. And of course, we’re going to refine the methods so that everything can be faster, everything can be better. But the conversation now is really about the works themselves, and the scholars who can read those works, and what we’re going to learn from the ancient world. You know, until the tech worked, we weren’t learning anything about the ancient world. We were learning about synchrotrons and virtual unwrapping. Now we’re actually reading the words, and the authors are coming alive. And that’s an amazing and a remarkable moment.

Nick Tawil
How do you refine the process that you basically pioneered here with your team? How long does it take today to read one scroll, and how long do you want it to take?

Brent Seales
I’d love for it to be an instantaneous thing, completely automated, that doesn’t take much longer than the scan time. We’re not even close to that right now. But imagine that you go to the scanner for your receipts from travel, and as long as it takes for it to scan is how long it takes for you to get the OCR and the thing to be uploaded. That happens right now for receipts and things like that. OCR, optical character recognition, was one of those first finally solved computer vision problems, and we would love for the scroll to be the same.

I don’t think that we’re that close to that right now. I think we’re still several years away from that kind of performance, because the technologies that we’re using are not that robust yet. But the computer vision and the machine learning that we’re using constantly improves. And we’re in this era now that is remarkable in that computer vision and machine learning, with more data, can get better. And so we actually see the ability to read the scrolls with the technology we’ve created as something that is going to create versions that get better over time as we read more scrolls. That’s never really been true with any other technology. Like, photography doesn’t get better the more photographs that you take. But because of the way the machine learning works, the more things that we capture, we learn from that, and then we get better at actually revealing the text.

So rather than time to text, which is one thing that we talk about, it’s quality of text, readability. We want to make the job of reading this ancient language the easiest possible. And overcoming the damage is really hard. I mean, this stuff is peeling, it’s fragile, so it’s kind of a miracle that it works at all. And then to say we want it to be pristine.

Nick Tawil
And instantaneous.

Brent Seales
And instantaneous.

Nick Tawil
So American of us.

Brent Seales
Yeah, well, it is. It’s always got to be better, right?

Nick Tawil
Oh, no. Actually, for the machine learning piece and the AI of it all that you and your team have been using to accelerate this process, in order to get it digitally unwrapped and handed over to the papyrologists, it comes across in the film in spades. But it also is something that other tech and VC investors have noticed, and even starting to make a little bit of waves in Hollywood, which is traditionally lukewarm towards AI. But in the film it comes across very, very cleanly, I think, and very authentically, that this is a great use case for AI, a positive use of AI, to further understand humanity. And I think it’s currently presented in the national conversation as either/or: you’re either for AI and against humanity, or for humanity and therefore you have to be against AI. And this is really a nice kind of marriage of the two in terms of a use case.

Brent Seales
Yeah, I see that. I think there’s irony that AI is so forward-thinking and premised on such modern and current technology, and yet we’re using it in this case to look backward. But it’s kind of a rescue mission, if not a sort of redemptive story, right? We’re kind of redeeming these lost works using AI as the tool to do it. And in fact, I like that message, right? That every new tool, including AI, that comes into human purview can be used as a way to redeem what’s around us. And so I think that actually is a really good story, and it’s one we should focus on.

Nick Tawil
So now that you’ve digitally unwrapped these three scrolls, is there a backlog of more scrolls, specifically from Herculaneum, or other labs or other researchers from around the world calling you up, saying, “Hey, you know what? I’ve got this parchment here that I can’t read. What do you think?”

Brent Seales
Well, it’s true that that is happening, and I’m glad that’s happening, because, congratulations, we have the technology to be able to look at some of that material. For example, there are scrolls in Amman, Jordan, from Petra, and they haven’t been opened. They’re carbonized. So there’s more material in the world that this could work on. But there is a backlog of just the Herculaneum stuff. I mean, we haven’t plowed through that. There are 40 scrolls that we’ve already scanned, and that’s 10% of what we think actually remains. So that’s a decade’s worth of work right there.

Nick Tawil
And the full villa hasn’t even been excavated.

Brent Seales
And that’s the next thing, right? The villa hasn’t been excavated. And I think people are a little bit naive about that. They think we have what we have and that’s it. But if you go down to the villa, which is not even open to the public... The villa is a part of Herculaneum that’s separate from the publicly available part of the town of Herculaneum. You go in there and you realize they really just sort of tunneled along the foundations of the villa, and that’s how they infer what the actual architecture of the villa was, and they just happened onto the artifacts that they have, including the scrolls, by doing that tunneling. It’s not fully excavated. And, you know, I’m not an archaeologist, but I would love to see, now that we know we can read the material, full archaeology happen there, not only to find the scrolls, but really to just better understand the villa and the scrolls we already have.

Nick Tawil
Well, it’s also, like you said, it’s the only ancient library that we know of. And what does that say about the authenticity of all these scrolls compared to maybe other artifacts that exist out in the world that academia or the research community currently has and uses?

Brent Seales
I love that you bring that up, because the provenance of scrolls from Herculaneum is unassailable. I mean, you can’t fake the carbonization. You can’t fake something being in this collection for 200 years.

Nick Tawil
So the carbonization actually creates an authentic fingerprint on this thing that cannot be exactly replicated.

Brent Seales
Exactly. Think about the Dead Sea Scrolls and how that all went down in the ‘40s. They were parted out by the Bedouin, so there were no archaeologists on site when they were found. And then you end up with advertisements in the New York Times for, like, a scroll from Israel. And what has happened since then is that we’ve seen a lot of fakes, where somebody will say, “I have a Dead Sea scroll, a scroll from cave number nine, Qumran, whatever.” And it’s really hard to prove sometimes that that’s true or not true. Not true with Herculaneum at all.

The other thing that’s amazing about a library from antiquity is that it’s not been copied by medieval scribes. So you have the original book that was actually on the shelf. So, fully authentic, verifiable, and the original book, not filtered through medieval scribes. And you know that a lot of the philosophy and the religion was tinkered with when the scribes of the medieval period recopied and preserved those works. And the tinkering is not always obvious. Sometimes scholars have to spend a lot of time to figure out, how did this change? They don’t have the original work, they just have the copy. Every book that we’ve read from Herculaneum has been a unique work. It doesn’t exist anywhere else in the canon, and it’s uniquely from antiquity. So it’s really a very, very compelling kind of collection.

Nick Tawil
So how long will it take you to do the next 40, 45 scrolls that you have in backlog?

Brent Seales
Right now we have a new competition that’s been announced, a $1 million prize through the Vesuvius Challenge, and that is for someone else, a competitor using our software, using their own, to do what we just did: read a full scroll from one of the 40. And we’re hoping that that’ll push our techniques forward. It’ll engage the community. Somebody will win $1 million for doing that. I think those 40 are going to be processed this year. That’s my hope. And then we’ll go after the remaining 360, the other 90% of what remains. A lot of those are fragmentary, so we know that we’re not going to have a whole book, we’re going to have a piece. But the game then becomes, if we can read all the writing, how do we put these works back together?

Nick Tawil
Why not grab a frontier lab here to just say, “Hey, we’ll just do this”?

Brent Seales
I’d love that. How do we do that?

Nick Tawil
We should have that conversation.

Brent Seales
We should do that.

Nick Tawil
And then let’s say these scrolls get scanned. How long does it take the papyrologists to analyze them?

Brent Seales
Papyrology is not fast, because what a papyrologist brings to bear when they look at the text is all of the other knowledge about the ancient world, because these texts are dense. Sometimes the texts aren’t fully...

Nick Tawil
You keep saying “dense.” What does that mean? A lot of text in a column, or the messaging is dense?

Brent Seales
Yeah, I mean, sort of intellectually dense. So you’re talking about parachuting into the middle of a book that is probably in the middle of a philosophical argument that a scholar is making, and they’re fully embedded in their time. So they’re talking about a person you don’t know whose name is maybe missing from the text, and about an idea that is only partial. And the game is to try to figure out, from the limited words, all of that stuff, all the context. And it can be really, really tricky and take a long time. Sometimes it ends up just being a mystery. It’s like, we don’t actually know what’s being talked about right here. We have all the words, but it’s really hard to know what the story is.

We’re hoping that most of the virtually unwrapped texts that we can provide are good enough in terms of readability and quality that the scholars will be able to unpack that density and figure it out. But the extra knowledge that the papyrologist has in their head, besides just the vocabulary and the structure of the language, is immense. And that’s what they’re applying, sometimes as a group and not just individually. Sometimes they have to work on it together.

Nick Tawil
So I want to talk more about the tech, and the tech throughout the entire workflow, to include what participants were doing at the Vesuvius Challenge and the challenges that they faced, either individually or as a group, in mapping out aspects of the scan, but then also the actual scan technology, the synchrotron you mentioned a few times. Give me a sense of scope for what a synchrotron is. Maybe start there, because that has to happen first, before you even engage people, your lab and other third-party participants through the Vesuvius Challenge, to even look at this stuff.

Brent Seales
Yeah, that’s right. We started by using a bench source. A bench source is one that you can move around. A bench source for X-ray would be one that you’d find in the doctor’s office or the dentist’s office. And so the first scans that we made, way back in 2009, the first time I ever scanned a scroll, it was done with a source that we took to the place where the scrolls were. It was just so much easier to have access if we were within the perimeter of where the scroll lived, at the library in the Institute of France in Paris. But what we discovered was that that source wasn’t going to give us some data that was good enough to do all the rest of this stuff.

So we quickly moved to the synchrotron, which is a source that isn’t movable. A synchrotron is an X-ray beam that comes from electrons that are running around in a ring at the speed of light. And the ring is like a kilometer across.

Nick Tawil
Just for this one scroll?

Brent Seales
Well, so the ring creates the electrons that run around in a circle, and then when you manipulate those electrons, it creates all of the different beams that you can use from this instrument. So it’s actually a huge campus around this ring, and one of those beamlines would be used to do the work on the scroll at a certain point. And you can tune what that beam is going to be in terms of the intensity of the beam and the energy that it has, all of the things that you think are needed in the characteristics to be able to elicit what you want from the scan. Way more controllability than something that you can take to the library.

Nick Tawil
So you have a lot of control.

Brent Seales
So what it created, though, was this problem of: now I have to take the material to this facility, and I have to guarantee the custodial holder, the people who own the scroll, the institution, that that’s going to be okay, that the scroll will be cared for, it won’t be damaged. So there was a time period where we had to shift to be able to use the synchrotron, but we hadn’t convinced anyone who actually had a Herculaneum scroll that we could do that. So you can imagine kind of going a little bit nuts, knowing that we could get better data, but we have to be able to convince the institution to let us do this thing. Once you get the scroll into the beam at the synchrotron, at that point, it’s really all about how do you capture the best possible scan, how do you optimize over a bunch of different parameters.

Nick Tawil
Which was a learning process.

Brent Seales
Which was a learning process. And the first time that we did it, we got what we got, and eventually we converged on a way of capturing the [unclear].

Nick Tawil
How much does this cost?

Brent Seales
The synchrotron cost, if you’re not being gifted the time, and typically we weren’t being gifted the time, would be $10,000 per shift, where a shift is eight hours. So, you know, a thousand, $1,500 an hour, and add inflation to that over the last two decades, and imagine how much.

Nick Tawil
And it’s the first time you’re doing it. You’re definitely going to have to learn off of that.

Brent Seales
Yeah, sure. And you’re not able to do the scan all in one go. So typically we do what’s called grid scans. You do a small section of the scroll, and then another adjacent small section, and then another adjacent small section, and you do these sections individually and then have to assemble the whole thing. So it’s its own thing to just capture the data and then manage the sizes and...

Nick Tawil
And not ruin the artifact.

Brent Seales
And not ruin the artifact. In a way, we were lucky, because these artifacts are completely inanimate. They’re completely desiccated, and they’re basically carbon, and you almost can’t do anything to carbon with X-ray. It just goes through.

But it’s also the worst case for solving the problem that we want to solve, because the X-ray doesn’t show the ink very well, or at all. There was a period of time, I don’t know if you know this, Nick, that people told me we would never be able to solve this problem, because it would be impossible to see...

Nick Tawil
Who told you that?

Brent Seales
Colleagues.

Nick Tawil
You don’t have to say their name.

Brent Seales
High level other professors, who felt like I was the guy tilting at the windmill, and they tried to sit me down and say, “You know that you’re never going to be able to see the ink using tomography. Carbon is invisible. You won’t be able to see the ink on top of this other surface.” And we refused to believe that, because we felt like there would be evidence. We just didn’t know how to tease it out.

And the two miraculous things that occurred that let us tease that out in a pretty non-obvious way: the synchrotron first. Super high resolution, so you can see the effects at a microscopic level.

Nick Tawil
How microscopic? Down to what?

Brent Seales
Well, a couple microns. A micron is one one-thousandth of a millimeter. So at one micron, you have a thousand slices in the space of one millimeter. That’s tiny.

Nick Tawil
So the two miracles that happened...

Brent Seales
The second miracle was AI, machine learning, because the evidence that is there is subtle. And so you need a tool that lets you amplify that evidence, embedded with so many other signals, because there’s a lot going on inside the scroll at that scale. There are fibers going everywhere, and there’s damage from the carbonization itself, and there are rips and tears and folds. And then somewhere, you know, the ink is actually on the surface of this ancient paper, which is not like normal paper. It’s not a composite that’s really uniform. It’s fibrous everywhere.

And so you have this really weak signal, and you have a pretty diminished modality, which is this X-ray modality. You would love to have visible light, but you can’t. And then along comes this incredibly sophisticated and powerful tool of machine learning that lets you find needles in haystacks, and boom.

Nick Tawil
And this is where actually the human comes in, too, because now you’re focusing AI engineers onto this problem, the Vesuvius Challenge. What are some of the obstacles that they had to overcome?

Brent Seales
Well, we had this huge labeling problem.

Nick Tawil
Labeling what?

Brent Seales
To break through... you couldn’t see the ink in the scans that we were getting with the naked eye, easily or at all. But when we trained the AI based on ink we knew was there... and we did that by using open fragments that had writing visible on the open layer. And then we would scan those with the same tomography, and then we knew where the ink was. We would label it “ink,” “no ink.” And then we could see that the machine learning would learn the evidence of the ink, even though we couldn’t see the ink with the naked eye in the scan. So all of that was scientific control, to be able to prove to ourselves there is evidence of the ink. The AI is learning it, the machine learning is learning it, but we have to label it for it to learn.

Well, how do you label the ink in a completely closed scroll? This was where the competitors gave us a huge boost, because now we have 2,000 people working on this problem, and they’re trying to create labels. And what they would do is they would run a fairly diminished machine learning effort on an open section of the scroll, virtually opened, and they’d see a response, some letters coming out of the mist, and then they would relabel. And iteratively, as more text gets exposed, they get more labels. Now amplify that across the 2,000 competitors...

Nick Tawil
24/7.

Brent Seales
With people sharing stuff, because we did inspire sharing through progress prizes. And so now you have the acceleration that we hoped we would get. The techniques weren’t substantially different than what we had already been doing, but the scale of what was happening, and iterations in terms of innovations were happening too, for sure. People were building tools that were helping. And so then eventually you’re solving this bootstrap problem by doing this kind of one-way ratchet, everything sort of getting better slowly.

And by the end of that year, I think it was 2023, maybe, we were headed toward the final submissions of the Grand Prize. Things were just accelerating like crazy. I mean, people sharing, and text obviously being detected from inside the scroll was very exciting.

Nick Tawil
And that’s when we got wind of it. And so at that point, you have something digitally unwrapped, then passed off to the papyrologists. And that’s a whole flow of work.

Brent Seales
Yeah. And we’re trying to improve that, actually, because it’s not really a one-way street at that point. Papyrologists just have a lot of insight into what looks legitimate and what might be an artifact. An artifact, for example, or even a mistake, might be what we call a sheet switch, where the virtual unwrapping actually gets off of the layer that it’s on and it descends to a lower layer. And the text, if you can read it, is going to tell you that that happened.

Nick Tawil
There’s, like, a break in the narrative.

Brent Seales
There’s a break in the narrative if you’re reading the words, or you can see sort of an obvious artifact that’s not going to be in a normal open scroll. And so we can actually go back and fix those things if they’ve happened. And usually the papyrologists are the ones who pick it up.

Nick Tawil
Oh, wow. So they’re actually involved pretty early on in the process. They’re not just waiting for you to hand them something.

Brent Seales
That’s right.

Nick Tawil
Cool. And then could you tell me a little bit about the scroll En-Gedi?

Brent Seales
Yeah. Before we were making such good progress with Herculaneum, this scroll from En-Gedi came to us through the Israel Antiquities Authority, and in particular the director at the IAA, who at the time was Pnina Shor. She’d heard of our work... we didn’t even know that this was happening, but she’d heard of our work and had found in their collection a scroll from En-Gedi that had been looked at by a number of professors, but no progress could be made because it was too badly damaged, and no one wanted to take on the formidable task of trying to open this little scroll physically, because it just looked like it was in pretty bad shape.

So she’d gotten that scroll back into the collection and then made a scan of it, and she used a bench source, not a synchrotron. And then she gave us the data and said, “Give it a try. We can’t do anything with this, and we can’t see any obvious writing, but I’ve read your work and maybe something can happen here.”

So it didn’t take us long, because this scroll was actually the perfect candidate for the moment in the development of our technology. It was animal skin and not papyrus, so in that way, it was less challenging. And then, as we did the virtual unwrapping, we found out that the ink... it must have been some kind of metallic ink, because the density of the ink in the X-ray was different from the density of the animal skin. So we weren’t looking at the same kind of really, really subtle effects of Herculaneum, where there’s no density difference at all. I mean, it showed up. The ink showed up in the En-Gedi scroll as a very bright signal sitting on top of this damaged animal skin, and boom, the text just appeared.

Nick Tawil
And what did it say?

Brent Seales
Well, that...

Nick Tawil
This text that had never been previously seen before, even by the owners of it.

Brent Seales
The scroll still remains wrapped up. It’s never been opened. But we could read everything inside because of these effects, using virtual unwrapping. And what we found is that it was a Torah scroll. It was the first remnants of the first two chapters of the Book of Leviticus from the Old Testament.

Nick Tawil
Wow. So how old was the scroll that you were given? How old was that expected to be, versus the text you found on the scroll? Is that the right question to ask? Like, “We don’t know what this is. We think it’s this old.” And then you find this. What does that change?

Brent Seales
The text definitely helped to date the scroll. They had carbon-dating evidence that put the scroll second, third century. But it had been found at an archaeological site that was Byzantine, so a couple hundred years later. So those results didn’t make perfect sense. There was disparity between the carbon dating and the archaeological evidence, which... they knew this site is Byzantine, so it’s probably fourth or fifth century. Once we read the text, it made more sense, because they could see the writing. So paleography, which is the analysis of the handwriting, dated it to an earlier era. So it was probably a scroll that they’d had in their collection at this synagogue for a hundred or a couple hundred years.

And as such, it was probably sacred. Something likely catastrophic occurred at that archaeological site, because normally none of the remnants would be in the Holy Ark. I think it was tradition that, the genizah, you would dispose of these artifacts, because they’re holy. And you wouldn’t just bury them or leave them partially burned for others to have. So this was the first time in a synagogue that they had ever discovered Torah. And it also became known as one of the oldest copies of the first two chapters of Leviticus.

And from the text, the scholars were able to tell that it was the canonical version, the Masoretic Text. And it’s a really early example of that settled text, so hadn’t changed. So, pushed the date for the settled Masoretic Text way back. They do have examples in the Dead Sea Scrolls collection itself of variations from the settled text, but this one was dead on the settled text of Leviticus. Pretty exciting.

Nick Tawil
Well, as we talk about this era, and we think about the papyri at Herculaneum, we know that the eruption happened in AD 79, but the scrolls in this villa could be much, much older. Because it was... I don’t know, you tell me, is it the sort of melting pot of a library that was collecting wisdom and scrolls from just around antiquity at the time? Give me a sense for what you would hope to find, or what a historian would hope to find and hope to see, in the remainder of the library.

Brent Seales
I think that the library probably was a place where they had an archive, so they had older texts. Typically, the way I understand it is that resident philosophers would write new works, but they would premise those new works on an archive of other works, often quoting them, extending the arguments in the earlier works, debating with each other, and then writing. So I think it’s very likely that there was an archive of much older works. And if that’s true and we discover those works, you could have literally anything.

It was a Roman villa, so it’s a little mysterious that there’s so much Greek and not as much Latin. So a lot of people have postulated that that’s just an archaeological feature, that it hasn’t been fully excavated. If we were to excavate it, because it’s a Roman villa, we would find much more of the Latin work. And I mean, that opens up all kinds of possibilities. We know of so many things that have been lost from the ancient world.

Nick Tawil
Let’s speculate. Let’s start speculating. I’m not going to hold you to anything, but I want to know.

Brent Seales
Livy’s History of Rome, for example. This would be for Alex Petkas, right? Because he knows everything that’s lost and found.

Nick Tawil
Cost of Glory great podcast.

Brent Seales
Yeah, exactly. Incredible. And then you have all of the literary and philosophical traditions of the Greek schools, so there could be much more of that. It’s thought that this particular philosopher, since we have Philodemus, was primarily an Epicurean. And there were also the Stoics. They argued with each other, and other schools.

If you ask me what I wish we could find, because the first century was such an amazing point in human history, I’d like to find early gospel material. Anything Christian at Herculaneum would instantly become the oldest witness that we have to early New Testament Christianity. I mean, even the fragmentary stuff from the New Testament is second century, for the most part. We have almost nothing from the first century, symbols only. But we know that this is Rome’s backyard. And we know the Apostle Paul was flitting around the world writing letters to the churches, which became part of the New Testament. So you have more than just the synoptic Gospels, which of course would be amazing. I mean, AD 79, right? This is just shortly after the life of Christ. So if there were writings that documented anything about his life that didn’t make it into the synoptic Gospels, those writings could potentially be in a library like this.

In, you know, the recent results corner of the library. I mean, most people who are academics and scholars would argue that it’s far-flung to think about anything that’s really gospel-y, because these libraries facilitated the ancient philosophies, and Christianity was new and hadn’t really taken hold. And I get that, nascent things at that time hadn’t made their way into the canon, the library, the archive.

But on the other hand, it’s fun to think about what could be there. The lost books of the History of Rome by Livy would give us a window into so many other events that would be better than just a philosophical tome. So rather than somebody talking about what it means to live a pleasurable life like an Epicurean, you could have somebody telling you about all of the events that happened as Rome rose and fell, and imagine how that would be. I think the historians would want history books, the philosophers want philosophy books, and the Christians want Christian books.

Nick Tawil
That’s great. Well, here’s to discovering new human knowledge. Thank you, Brent, for your time.

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Show Notes

Ryan Resch & Jimmy Soni

• Ryan Resch on LinkedIn: Former Suns Assistant GM and VP of Basketball Operations, now leading data and AI at 1949 Capital Partners. Connect with Ryan

• Beyond the Dashboard: Ryan’s Harvard Business School interview with Boris Groysberg on optical tracking, dashboards, and AI. Read the interview

• Shore Capital Partners: The private equity firm founded by Justin Ishbia, where Ryan helped roll out AI tools. Shore Capital Partners

• Jimmy Soni on X: Guest host, bestselling author, and editor-in-chief of Infinite Books. Connect with Jimmy

Teams, Leaders & Data Discussed

• James Jones: The 2020-21 NBA Executive of the Year, whose Suns rebuild started with raising the floor. Executive of the Year

• Scott Drew: The Baylor head coach who answered Ryan’s cold email and later had him build lineup data. Scott Drew at Baylor

• SportVU: The camera system that brought optical tracking to every NBA arena in 2013-14. SportVU and the NBA

• Second Spectrum: The machine learning platform that turned tracking data into tagged plays and dashboards teams across the league use. Second Spectrum and the NBA

• Hawk-Eye: Sony’s 3D tracking system, used across the NBA since 2023-24. Hawk-Eye and the NBA

Books, Shows & AI Tools Mentioned

• Moneyball by Michael Lewis: The 2003 book on the Oakland A’s that frames how analytics moved from baseball into basketball. Moneyball

• Hyperion by Dan Simmons: The first book in the sci-fi series Ryan is reading, and a window into how earlier writers imagined AI. Hyperion

• The Founders by Jimmy Soni: Jimmy’s history of PayPal and Silicon Valley, which Ryan handed out at the Suns. The Founders

• TBPN and Dwarkesh Podcast: Two of the tech shows Ryan wishes he had more hours for. TBPN | Dwarkesh Podcast

• Claude Code and Codex: The coding agents Ryan uses in a workspace built for agents to read. Claude Code | Codex

Highlights

When Does Peanut Butter Become a Meal?

Ryan Resch
I got in trouble by the NCAA for buying honey roasted peanut butter.

Jimmy Soni
What?

Ryan Resch
Because I had no idea. So the NCAA was extremely strict pre NIL. And the meals, what classified as a meal, was extremely strict as well. And so we could not provide food under certain conditions to guys because then it would be considered a meal. If they get a meal, it’s an impermissible benefit.

Jimmy Soni
Wow.

Ryan Resch
Oh, it was a whole bureaucracy. I mean, it still is a bureaucracy.

Jimmy Soni
Right.

Ryan Resch
But on a different level. And so, look, according to Baylor compliance, adding honey to peanut butter made it a meal at that time.

Jimmy Soni
Adding honey to peanut butter that a player was going to eat...

Ryan Resch
Yes.

Jimmy Soni
Made what you did impermissible.

Ryan Resch
Yes.

Jimmy Soni
Oh, wow.

Ryan Resch
It’s absurd. Absolutely crazy.

Jimmy Soni
That is bananas.

Ryan Resch
It is. And you talk about, you know, you go back to your previous question about data and logic entering sport, the human component. The bureaucracy of it all is what removes the human component. Whereas the player needs this. Not like, let’s put aside the fact that people just love peanut butter. Like, it’s amazing and I can’t have it in the house. Players need this to recover. They need the sugar, they need the protein, they need the fat. Right? So you are instead focused on this arbitrary definition of impermissible benefit instead of what’s best for the players.

Jimmy Soni
Right. That’s right.

Ryan Resch
Yeah. I think that’s what’s actually removing it.

The Coaches Take the Blame

Jimmy Soni
Oh, okay. You know, during your tenure, they were really starting their climb. So what did you see in that culture? Like, what was it that made Baylor stand out from other comparable programs?

Ryan Resch
I will say one of the things that I understand now that I did not understand then was the coaches always shouldering the blame for the players. Always. And behind closed doors, you know, publicly as well, that one’s more obvious. Like, a lot of coaches do that. But even behind closed doors, a lot of the conversations would center around, okay, if this player is turning the ball over, how do we teach them not to do that? How do we put them in a position not to do that? And I think that’s notable because obviously sport is extremely emotional.

Jimmy Soni
Right.

Ryan Resch
It is very volatile. You’re going to lose three games in a row at some point.

Jimmy Soni
Yeah.

Ryan Resch
And you have to really have this stability in order to ride that. And the easy thing to do there is to get all pissed off and start blaming the players. Say that you need better players, you need more talent, whatever. And maybe that is objectively true. If you are going up against a Duke that has the top five guys in the class, like, whatever, like, you still need to figure out how to beat them. But to see a coaching staff led by Scott Drew, Jerome Tang, a lot of the folks that are still there, shoulder that blame. And then they would always tell them, they would tell me, they would be like, “It’s our fault.”

Jimmy Soni
Oh, wow.

Ryan Resch
And I would say, “I don’t understand this. We’re not the ones turning the ball over.” Because I was so, like, petulant. And then I get it now, like, having gone through everything that I went through at the Suns and everything that’s come after. Like, I understand now that when you ask about the culture of that space, you need to create a teaching culture, like an actual learning culture, where somebody can make a mistake, like turning the ball over or missing a shot, and then know that it’s not going to result in punishment, it’s going to result in a lesson. Maybe that lesson is hard, right? It’s tough love. But there is going to be a lesson involved in it.

Edited Transcript

Jimmy Soni
Welcome to Infinite Loops. My name is Jimmy Soni. I am the editor in chief of Infinite Books and I am guest hosting for Jim O’Shaughnessy. My guest today is Ryan Resch. Ryan spent nearly a decade with the Phoenix Suns, where he started as an intern and left as the assistant general manager and VP of basketball operations, running everything from roster strategy and data science to scouting and health and performance and everything in between. Ryan Resch, welcome to Infinite Loops.

Ryan Resch
Thank you. Thanks for having me.

Jimmy Soni
Of course. So, just so listeners have a bit of context and background, you and I have been friends for a number of years, but when I met you, you were the vice president of basketball operations for the Phoenix Suns, the assistant general manager, and you reported directly to the head of the Phoenix Suns. And you kind of gave me and a number of other people we were with a behind the scenes view of the Suns organization and how it operates. But just so people listening have context: first of all, you were in an NBA front office at, like, a ridiculously young age. You were chief of staff to the head of the organization when the Suns went to the Finals and when they won 64 games.

Ryan Resch
Franchise record.

Jimmy Soni
Yeah. And then you become this kind of, you’re like one of the go to people on sports and data and where they intersect, and now sports data and AI and where they intersect. And right now you are at 1949 Capital Partners and you’re leading the firm’s work on data and AI. So the thing that interests me most, I mean, among other things, is, you know, you’re not six foot four, right? So walk us through kind of like your early life. You were a military brat. But I want to go from, to, before you get to the NBA, let’s figure out how you got to the NBA. So you started out in life and you’re a military brat, you’re moving around a lot. So walk us through: where’d you grow up? How’d you live?

Ryan Resch
Son of two Air Force parents. We lived in seven places before the age of 18 years old.

Jimmy Soni
Wow.

Ryan Resch
Which I always kind of surprise myself when I say that. So, born in New Jersey, lived on effectively every coast. Went to high school in Germany. So I went overseas for high school. It was a military base, on Ramstein Air Base. So still kind of an American experience there, but we did live in a German village. And so it was, you know, a bit of an international time. Came back and moved to Texas to go to Baylor University, where I had family in Texas, in Florida, from my parents’ sides. And Baylor was the first school to accept me. And I’m not the most patient person. And so the fact that they did accept me so quickly did help while I was waiting on other schools. Did enough research into Baylor, their political science program, which was my first, I would say, passion and first love growing up, was political science. Probably from being around the Air Force and the military and learning that side of it. And enrolled in the... would that have been the fall of 2010?

Jimmy Soni
Got it.

Ryan Resch
And I was a campus tour guide my sophomore year. I’m still very good at walking backward and talking. And I had this weird desire to go into sports journalism, which I don’t...

Jimmy Soni
Were you a sports fan growing up?

Ryan Resch
I was a huge NFL fan and I was a big basketball fan.

Jimmy Soni
Okay.

Ryan Resch
But it’s hard when you’re a military kid because you don’t really have a home. So whenever I’m asked, “Oh, where are you from?” I have to give this whole long explanation around it. And when you don’t have, like, a hometown, it’s hard to really pinpoint what you’re a fan of. And I got into basketball when we lived in Florida. So I became a Miami Heat fan at the time, right around when Dwyane Wade was drafted, which was then ironic, that my future boss, James Jones, was on those Miami Heat championship teams. And my dad was a big Pittsburgh Steelers fan growing up. So I grew up as a big Pittsburgh Steelers fan and I loved watching sport. I loved the competition of it, the game of it. And I had no, as you mentioned, I’m not six four. And so I had no... I’m deeply... I have no coordination, no hand...

Jimmy Soni
To be clear, Muggsy Bogues, like, broke the mold, right? Like, when I was growing up, because I was short and I loved basketball, so in the brief period in which I held these, you know, dashed dreams of becoming a basketball player, I would just turn to Muggsy Bogues. Like, Muggsy made it work.

Ryan Resch
There you go. That’s all you need. You just need determination and grit and hope that your jump shot... And I, for a very short period, decided to double major in journalism, which I quit. And then decided one day, it’s like, I am just going to cold email Scott Drew, who is the head coach of Baylor men’s basketball still to this day. And testament to him that he responded right away. So right after my summer, after my sophomore year, I sent a cold email to Scott, said, “I respect your program. I admire what you’re building. If there’s ever anything I can do to help, let me know.” And he replied that same day, if I’m remembering correctly. And he said, “Come be a student manager.”

Jimmy Soni
Wow.

Ryan Resch
And I said yes. I had no idea what it meant.

Jimmy Soni
Right.

Ryan Resch
And I show up maybe two or three days later, and I am an equipment manager, folding towels and doing laundry for Baylor men’s basketball.

Jimmy Soni
Wow.

Ryan Resch
And it’s very... they just throw you right in. And so you’re in the locker room, like, getting everything ready for the guys before practice, after practice, for games. You’re on the court helping, you know, rebound and pass balls and those kinds of things. I was so bad at passing a basketball. When I threw, it was so bad that Scott Drew called me into his office. He probably remembers this. And he taught me how to throw a chest pass with spin on it. Like, how embarrassing is that?

Jimmy Soni
So just so I have this clear. So you were, you’re there and you’re passing basketballs. Did the players say something? Did they know something? Or he just installed...

Ryan Resch
How bad... Coach Drew. Okay, this is Coach Drew. This is why he’s a national championship coach. Because he sees these things and he fixes them.

Jimmy Soni
Right. Even in his student manager.

Ryan Resch
Exactly. Exactly. And that, I think it says a lot about him, but it also says, I guess it’s like an early lesson...

Jimmy Soni
Yeah.

Ryan Resch
Like the nature of detail.

Jimmy Soni
Right.

Ryan Resch
Sport and winning, these things. Because if you throw a knuckleball, if you throw a ball without any spin, you can break someone’s finger.

Jimmy Soni
Right.

Ryan Resch
And jam their finger. Right? God forbid it’s on a shooting hand.

Jimmy Soni
Yeah. Wait, is that true? Sorry, is that true in... So you’re saying in basket... Knuckleballs are a baseball term, right?

Ryan Resch
But it is, yeah. So a ball with no spin.

Jimmy Soni
Yeah.

Ryan Resch
So I wasn’t putting any spin on my chest pass. I was just literally chucking the ball. I was accurate. Like, accuracy was not the issue. This is actually getting spin and rotation on the ball, which the best shooters can tell you about, because you have to put backspin on the ball in order to actually guide it to the target that you’re launching. Don’t ask me about shooting. I’m not...

Jimmy Soni
Not the expert. Okay, so just out of curiosity, if we take a step back in the story... I mean, I want to go a bunch of different places, but let’s talk about living in seven different places before the age of 18. Right. Because that is not an experience that I had. I’m assuming actually most listeners are pretty geographically... As a kid, you know, your parents do tend to want to stay in one place by design. Your parents can’t, right? So what was it like being the new kid all the time? Right. Like, was that... I mean, I’m sure this shaped your life. I’m asking, how did it shape your life?

Ryan Resch
Yeah. I think the most obvious is what I’ve already mentioned, where you don’t have a sense of home in the traditional way that people think about that. Where I’m just now learning, so we still have a house in Phoenix. Love Phoenix. Very actually attached to that house. And that is the first kind of time that I’ve felt that I can call a place home.

Jimmy Soni
Yeah.

Ryan Resch
And that has been a very kind of transformative experience for me. The other aspects of it, you become very adaptable and you become very malleable. You could enter any space and be comfortable. I’m also an only child, so I have no brothers or sisters. This was just me and my parents running around the country and then over to Germany. And you’re able to talk to people and you’re able to introduce yourself, maybe not so comfortably when you’re 12.

Jimmy Soni
Yeah.

Ryan Resch
But you know, you start, you get reps at it.

Jimmy Soni
Right.

Ryan Resch
I think probably the more important thing is I was forced into situations where I had to get reps at introducing myself and telling people and showing people who I am, as I’m also trying to figure that out throughout the rest of my life.

Jimmy Soni
Right.

Ryan Resch
Or growing up, rather. And it does leave you with kind of a few things. One of them is I’m always moving. Like, not moving homes necessarily now, but I am always constantly in a new place. So it’s very hard for me to stay still.

Jimmy Soni
Yeah.

Ryan Resch
This is why sports was so good for me. Because you’re on two week east coast road trips and you’re playing in Toronto and then tomorrow you have a game in Philly and you’re just kind of moving around a lot. And then it also leaves you just with this sense of confidence, if you’re kind of maturing into that space, where you can just enter spaces.

Jimmy Soni
Right.

Ryan Resch
And be okay.

Jimmy Soni
Right.

Ryan Resch
In a way that maybe somebody who hasn’t had that experience just needs more reps at it.

Jimmy Soni
Yeah. So this ties to my next question, which connects to the time with Baylor and with Coach Drew. You know, there are a lot of people who watch sports as casual fans or as kids kind of admiring athletes from afar, and there’s a certain impenetrability to the world of sports. You think, well, if I don’t have that level of talent, there’s no way for me to get involved in sports. Right. And so for you, you do this extraordinary thing, which is, like, as a sophomore, you take a gig that puts you at the very, very bottom rung of the organization. When you sent that email, like, if you can think back that far, that’s a pretty extraordinary... Like, I’ll give you an example. I’m suddenly sitting here so jealous that you did that. Because I went to Duke and basketball’s a religion.

Ryan Resch
They have a whole manager program.

Jimmy Soni
And I would have been like, I would have been applying if I had known that was even a possibility. Right. But I never knew it was a possibility. And so my question is, how did you... Was it in that moment, was it a desire to be closer to sports, or was it just kind of on a whim? Like, what motivates you to do that? Because it really does shape the rest of your trajectory.

Ryan Resch
It did. I think it’s all of those things that you’re saying. The idea came to me because my boss, actually, at the campus tour guide center...

Jimmy Soni
Yeah.

Ryan Resch
She had a Baylor basketball poster on her wall in her office, and we would always talk about the games and Baylor basketball. It’s an excellent program. We’re still excellent. And this was kind of the first period of, like, Scott Drew’s excellence was those, like, 2010 to 2014, really.

Jimmy Soni
Right.

Ryan Resch
When I was there.

Jimmy Soni
Yeah.

Ryan Resch
Those years. And so we...

Jimmy Soni
That was a nice subtle wave. And, like, you know, I might have had something to do...

Ryan Resch
Well, they won the National...

Jimmy Soni
Once I fixed those passes I was passing back to the players, everything got better.

Ryan Resch
And she, we would just talk about it so much, and I think I maybe just said offhand, like, “I wonder how you even begin to get involved in that.”

Jimmy Soni
Yeah.

Ryan Resch
And she was like, “Just email Scott Drew,” or something like that.

Jimmy Soni
Right.

Ryan Resch
And this was, it’s so commonplace now. If you want to reach someone, it’s their company name, their first initial, last name, or their first name@company name.com, or whatever it is. I think that was still a bit of a foreign concept back in, whatever it was, 2012.

Jimmy Soni
Yeah.

Ryan Resch
And so I was probably very nervous to send it.

Jimmy Soni
Yeah.

Ryan Resch
But it also, like you said, it sparked all of this. And it’s why I have this rule that if someone reaches out to me...

Jimmy Soni
Yeah.

Ryan Resch
And wants advice on how to get into sport, then I will at least talk to them one time so that we can go through this process of, hey, you’re in college, you want to figure out how to do this. You need to find the director of basketball operations for your team, send them an email saying that you want to be a student manager and ask if they have that program. And the reason I do that is because I didn’t have that guidance. I did it. And it’s cool now because there’s actually a few people around the league that were undergrads that reached out, that became managers at Tennessee and other schools that are now in the NBA.

Jimmy Soni
Wow.

Ryan Resch
Because of it. But I think I’m a bit of a venturer now, is how I can describe it. And in order to do that well, you just have to have the agency to send the email. Right? Just send the email. If they don’t respond, everything’s okay.

Jimmy Soni
Right.

Ryan Resch
Find the next thing.

Jimmy Soni
Right.

Ryan Resch
And then keep going.

Jimmy Soni
That’s great. Okay, so you did mention this, but Baylor was a serious, and it’s still a serious program. I mean, you went to the, I think it was a 2021 championship, right?

Ryan Resch
Yes, it was Covid. It was the Covid tournament. Because I did not get to go, unfortunately.

Jimmy Soni
Oh, okay. You know, during your tenure, they were really starting their climb. So what did you see in that culture? Like, what was it that made Baylor stand out from other comparable programs?

Ryan Resch
I will say one of the things that I understand now that I did not understand then was the coaches always shouldering the blame for the players. Always. And behind closed doors, you know, publicly as well, that one’s more obvious. Like, a lot of coaches do that. But even behind closed doors, a lot of the conversations would center around, okay, if this player is turning the ball over, how do we teach them not to do that? How do we put them in a position not to do that? And I think that’s notable because obviously sport is extremely emotional.

Jimmy Soni
Right.

Ryan Resch
It is very volatile. You’re going to lose three games in a row at some point.

Jimmy Soni
Yeah.

Ryan Resch
And you have to really have this stability in order to ride that. And the easy thing to do there is to get all pissed off and start blaming the players. Say that you need better players, you need more talent, whatever. And maybe that is objectively true. If you are going up against a Duke that has the top five guys in the class, like, whatever, like, you still need to figure out how to beat them. But to see a coaching staff led by Scott Drew, Jerome Tang, a lot of the folks that are still there, shoulder that blame. And then they would always tell them, they would tell me, they would be like, “It’s our fault.”

Jimmy Soni
Oh, wow.

Ryan Resch
And I would say, “I don’t understand this. We’re not the ones turning the ball over.” Because I was so, like, petulant. And then I get it now, like, having gone through everything that I went through at the Suns and everything that’s come after. Like, I understand now that when you ask about the culture of that space, you need to create a teaching culture, like an actual learning culture, where somebody can make a mistake, like turning the ball over or missing a shot, and then know that it’s not going to result in punishment, it’s going to result in a lesson. Maybe that lesson is hard, right? It’s tough love. But there is going to be a lesson involved in it.

Jimmy Soni
Can I ask you this? This question is a bit more just personal perspective. But, you know, when you’re a college student, sometimes you have a too healthy sense of your own importance, right? And I’ve got to believe, like, you’re a very smart guy and you’re studying political science, you know, and you’re at Baylor and you have a good head about you, and now you are folding towels, right? Like, how did you put your ego to the side? And was it a rude awakening? Like, you get in, you think student manager is going to do all kinds of interesting things, and now you’re folding towels and you’re learning how to pass better. What was that like? Like, is there a part of this that was just, you already knew what you were getting into, or was it now the proximity of the game was the payoff? Like, it was just you wanted to be a part of this and you figured this was the way to do it.

Ryan Resch
I did not know what I was getting myself into. It’s funny that you asked that, because one of my fondest memories is on Sundays at Baylor, people are at church and Ryan was cleaning the gym. I was cleaning the practice gym. And I loved it because you had to get this big pole out, put towels on it, and, like, drag this pole all the way across the court in order to clean it. And it was just a very cathartic, like, meditative. Meditative, that’s exactly what it was. You would turn on a podcast or music or something, and you would just do it, and then you would clean the gym. And I don’t remember having kind of an adverse reaction to any of it, although I probably did at some point, years, when I was head manager my senior year. Right? Did I act probably some way where it was like, you know, now this is beneath me, the young manager can do it? Probably.

Jimmy Soni
Yeah.

Ryan Resch
But what you learn in doing it genuinely, when you are the person putting out the loops that have all of the jerseys and the shorts and the socks and everything on the player’s chair, it’s behind a locked door, so if you’re not doing it, player can’t get dressed, player can’t practice. And so you’re able to actually experience, like, the operational chain of how we go from this nice idea, all right, let’s run a basketball team, to, no, these are all of the dirty steps and the details that it takes to get it done.

Jimmy Soni
Yeah.

Ryan Resch
And I think that was a huge payoff for me, especially my last year at the Suns when I did run the daily operations of the franchise.

Jimmy Soni
Yeah.

Ryan Resch
Where it was like, I knew what our equipment manager was going through.

Jimmy Soni
Okay.

Ryan Resch
Where he’s dragging these trunks around constantly, him and his assistant. And how do we lighten that load for those people who are extremely important to get this done.

Jimmy Soni
So at some point during your tenure at Baylor, you become the guy who has the data, who has the numbers. So what’s chapter two? In excruciating detail, describe, like, you know, spare no story there. How do you go from towels to analytics and spreadsheets? And you’re helping the coach think differently about the game. When does that transition start to happen?

Ryan Resch
So I was head manager my senior year, and political science was my passion. Basketball was my hobby. Like, that was kind of the differentiation that I put there. That’s really the only two things I had, outside of friend group, obviously. But we would be at the gym till 3am scouting the next opponent, and, like, at crazy hours.

Jimmy Soni
Wow.

Ryan Resch
Still, even in the NBA, crazy hours. And I graduated, I went to go get a PhD in political science at the University of Missouri. There was a professor there that I wanted to study under for American Political Development. And around, was it my sophomore, it was either my sophomore or my junior year of undergrad, I was introduced to data science and statistics through econometrics and political science. And when I kind of dug deeper into that world, I realized, oh, my brain is actually extremely logical. And, like, coding came naturally to me. Data came naturally to me. I still love theory. I still love philosophy, liberal arts, all of those things, for sure. How do we blend these two things? I go to Mizzou for a year and we’re working on these papers and this research, and I just have this feeling that’s like, this is just not it for me. This is not right for me. Different than when I, you know, quit campus tour guide to go to basketball. This was like, no, this is fundamentally not the place for me.

Jimmy Soni
Yeah.

Ryan Resch
And I think what I ultimately settled on, which is kind of a principle that I now carry throughout life, is I don’t want to study problems. I want to actually solve the problem. Now that requires you to study them in order to solve them. Yeah, but we’re not going to actually solve it if we are just kind of writing papers and going about our day. I want to actually do. I want to do all that, and then I want to do it to see if we’re right or not about it. And I decided that I was going to leave the program, so I quit. And I did not know what I was going to do. I had absolutely no idea. It is probably the scariest period of my life because I just had no concept of what else I could be doing. Right.

Jimmy Soni
Yeah.

Ryan Resch
And I happened to go to the Big 12 tournament, which is the conference that Baylor, I think they’re still in.

Jimmy Soni
Yeah.

Ryan Resch
I can’t keep up with the conf...

Jimmy Soni
I know. Neither can I. It seems to change on a dime.

Ryan Resch
It’s, yeah, wild. And I went to the Big 12 tournament, spent a few days with the team again and realized, okay, I think I just missed the team environment. So I called Scott Drew again, and he answered again. And I said, “I don’t know what I’m going to do, but do you have any advice for me?” And he was like, “Well, I just got done talking to Tom Izzo at Michigan State,” who’s a good friend of his.

Jimmy Soni
Yeah.

Ryan Resch
And legendary coach.

Jimmy Soni
Legendary. Yeah.

Ryan Resch
“And he just hired someone to do data science and statistics for them. Can you come do it for me?” I said, “Sure.”

Jimmy Soni
That’s amazing.

Ryan Resch
And that was amazing. Probably a month leading up to... Well, first we had to get me into a grad program because this was very late. It was like April at this time. Thankfully, that all worked out.

Jimmy Soni
And why did you need a new grad program? Because he couldn’t hire you unless you were a student?

Ryan Resch
I was going to be a grad assistant. Yeah. I was going back as a grad assistant.

Jimmy Soni
Got it.

Ryan Resch
So there’s, like, the student manager program for undergrads. There are grad assistants. Typically grad assistants are going to follow the coaching route, although more and more commonly it’s video analytics and whatnot as part of it. And I guess GM now for these colleges. And so I go back to Baylor in, whatever was that, 2015. 2015, spring of 2015. Yeah. And Coach Drew’s like, “I want lineup data.” Okay. And lineup data did not exist at this time. Like, there was no easy accessible, like, public form of lineup data that you could also trust. You know, it was a whole kind of amorphous concept still.

Jimmy Soni
And just for context, like, I remember, I think Moneyball came out in 2003. The movie is like 2011, something like that. So we’re not in the... we’re still, we’re post Moneyball, but we are pre, like, the digitization of everything, sports especially.

Ryan Resch
Probably at that level. And it also started in baseball. So Moneyball is the baseball book, obviously. And then it kind of slowly made its way across football and soccer and, you know, obviously lacrosse and those other ones. And then basketball was also really starting to take off. Daryl Morey popularizes, you know, threes and layups only with Moreyball. And that’s kind of the launching of the analytics movement in the NBA at, like, a popular level.

Jimmy Soni
Yeah.

Ryan Resch
And Moneyball kind of joins along those lines. So the mid-2010s was, I would say, really where teams and people took it more seriously in basketball.

Jimmy Soni
Yeah.

Ryan Resch
And so there was just no lineup data for college basketball that we could rely on. And to this day, I don’t know how I had this idea. But in basketball, all sports, you have the play by play.

Jimmy Soni
Yep.

Ryan Resch
That says, okay, you know, your point guard is subbing in, your shooting guard is subbing out. Point guard made a two point shot, assisted by your small forward. Along those lines, in text.

Jimmy Soni
Yes.

Ryan Resch
Pre AI.

Jimmy Soni
Yeah, pre AI.

Ryan Resch
Early days of machine learning and AlexNet and those things. And I scraped those play by plays.

Jimmy Soni
Wow.

Ryan Resch
And from the text, I turned it into a box score and so we could build the... And I’ll never forget this. This all hinged on two things being true. The sub ins, sub outs had to be on the play by play.

Jimmy Soni
Yeah.

Ryan Resch
Else this wouldn’t work.

Jimmy Soni
Right.

Ryan Resch
And the starters, there had to be a connotation of who started the game.

Jimmy Soni
Huh.

Ryan Resch
So typically that would be the first five players listed. Not always, but thank God there was an asterisk next to the starters.

Jimmy Soni
Just so I have this right, so I’m understanding this correctly. There was no box score data for Baylor or maybe even men’s college basketball at circa whatever year this is, 2015. Nobody is tabulating these and putting them on ESPN. Wow.

Ryan Resch
For individuals, yes. Yeah. Like, you can go to College Basketball Reference, amazing website. They have the individual box scores and whatnot because that comes from the scorer’s table, the statistics from the game. This was, no, okay, now we want to know five man combinations. So for those who don’t know, a lineup would be your point guard, shooting guard, small forward, power forward, center.

Jimmy Soni
Yeah.

Ryan Resch
Five man combinations. How are they performing together?

Jimmy Soni
Got it.

Ryan Resch
I’m not going to say it’s like a brand new concept. Right. Getting that data at scale so we can have it for Baylor and our opponents.

Jimmy Soni
Yeah.

Ryan Resch
Was a novel problem to solve.

Jimmy Soni
Okay. So you scrape the data and you build something to scrape the data, and then what happens after that?

Ryan Resch
We converted the text into the box score. Yeah. So point guard made two point shot. That becomes two points, two point field goal attempt, two point field goal make. So each of the little traits that you can, the variables that would make up that action, you can now register and log it in your box score. And then you sum it all up and you aggregate by lineup. And then, you know, I think, and this is what AI I think is teaching so many of us, is once you have the data extracted and structured, you can do so many different cuts of it. And so now we have five man, four man, three man, two man. Like, what about these different combinations of guys? Like, it just kind of exploded in that way. And coach was happy with it and it started just kind of influencing rotations and substitution patterns and those kinds of things.

Jimmy Soni
So, yeah, this is where I want to go a bit deeper. Because, I mean, famously, the scenes in the movie in Moneyball, but then also as described in the book, is there’s a graft versus host problem. Right? Like, you have a person who’s very smart with this kind of stuff and there’s an allergic reaction from people who believe it’s going to sully the sanctity of sport. Right? You’re going to add an impurity, which is like logic and reason, in something that ought to be subject to competition and fate and individual effort and all these other kind of more, call it more ethereal, things. Right? And into that you’re introducing, like, logic and regression analyses and actually looking at data. Did you face any of that when you were starting to pull these things together? Like, were you sheepish? Was the coach resistant? Was there any part of the organization that was like, “Ryan, we love this stuff, but we know how to play the game and you don’t. You couldn’t even throw a pass until he coached you to throw the pass better.”

Ryan Resch
Maybe that’s why it worked. Because this coach knew that I wasn’t trying to front as though I knew how to do these things. I definitely have run into that resistance. Yes. But I’ve also been extremely fortunate that the principals that I have worked for, so Scott Drew, James Jones, these are people who are very rational thinkers to begin with.

Jimmy Soni
Yeah.

Ryan Resch
And so they want this data, they want this information. And so that helps, number one. But what it does teach you is this incredible lesson of, like, and I think that this is important for data folks and maybe more, like, rationally minded folks, is there is a difference between being effective and being right. And this is something that I had to learn at the Suns. And it came from kind of exactly what you’re describing, which is if sport is this constrained, bounded game that we have all of the rules for, we know exactly how it’s structured, there is a very clear scoring and reward system, we can apply game theory, we can optimize it for strategic and tactical choice. If that’s true, then why are we not doing it, right?

Jimmy Soni
Right.

Ryan Resch
And the answer in my mind always came back to what I called the communication problem, which is we are fundamentally lacking the ability to communicate why these insights matter to help you make better coaching decisions, or you make better playing decisions, or you make better executive level decisions like who to put on the roster and who to take off.

Jimmy Soni
Right.

Ryan Resch
And I think there are a host of ways to solve that. The language that you choose, the tone in which you speak to people, like the more maybe ephemeral concepts that are qualitative, maybe more quant driven folks don’t naturally move toward. But I think also, and this is where I hope it goes in sport, is team building is a beautiful art and a beautiful science. Like, there’s really a blending of it to do it well. It’s the cultural aspects that you asked about earlier, as well as, if you think about kind of a two by two grid when you’re making team building decisions, whether it’s a roster or your staff, you know, for a job somewhere else, you have to focus on the person and you have to focus on the professional. So instead of person, for sports it’d be a player. So player and professional. You have to focus on the league’s perception, so kind of the in a vacuum perception.

Jimmy Soni
Yeah.

Ryan Resch
And you have to focus on, for my team, what is that going to be? So this player X might be an excellent three point shooter in the league standards. Absolutely excellent. But they can only get their threes off of very specific actions. Those actions are not good for our team because we don’t have the person to create those actions. And so I objectively believe that you are an excellent three point shooter, but you’re not going to help our team right now. You have to kind of hold this balance, and that’s a very human thing, is to hold these conflicting and competing views in your mind. And I do think that where data helps is quantifying and telling that story of player, professional, person, professional. How are they viewed kind of in a vacuum within their entire cohort, and then how are they viewed for our team specifically under our conditions? And if we can get the data, with the help of AI, if we can get the data more down that more human story...

Jimmy Soni
Yeah.

Ryan Resch
Then I think it becomes more easy to apply it. And once it becomes easier to apply, it’s more helpful.

Jimmy Soni
Right.

Ryan Resch
And once it’s helpful, it’s valued.

Jimmy Soni
What’s an example from your days at Baylor where, because you’re really creating this stuff from whole cloth, right, and there’s not anybody feeding you this, you don’t have APIs you’re plugging into, you’re doing this largely on your own, I assume. What’s an example of something that shifted because of something you found? It can be small, it can be big. But, like, what’s an example of when you had an insight and you said, this is, I’ve generated new knowledge here, and then something shifted in the organization as a result?

Ryan Resch
At Baylor specifically?

Jimmy Soni
Yeah.

Ryan Resch
I think one of them, we had a forward who, absolutely excellent scorer. Yeah, absolutely excellent. Six eight, six nine, you know, very smooth scoring the ball, and he didn’t get a ton of minutes. And part of that was because, like, he wasn’t the hardest worker, did not kind of present as, you know, like, a cultural anchor of the team, those kinds of things. And I’m not saying that is a deserved reputation or not, but when you looked at the numbers and you said, okay, when this player is on the floor, like, per minute, the impact that this guy is having is actually extremely high. Okay, how do we fix these things that are going wrong so that maybe he shows up on time? Or how do we put a better environment around him where he’s playing with certain guys who are going to get the most out of him, because his per minute efficiency is so high? Let’s not turn a blind eye, but let’s focus on fixing those things that we really dislike, that we want to vent about, so that we can unlock this for the team.

Jimmy Soni
Got it.

Ryan Resch
So that we can unlock this scoring prowess for the team. Because it’s really easy, again, sports is extremely emotional, it’s really easy to be focused on, we just lost, you were late to shoot around.

Jimmy Soni
Right.

Ryan Resch
You’re one of the reasons that we lost. I’m not saying that’s not true.

Jimmy Soni
Right.

Ryan Resch
But the payoff of unlocking that...

Jimmy Soni
Yeah.

Ryan Resch
We can now see what that looks like.

Jimmy Soni
Got it.

Ryan Resch
And that’s where, you know, we talk, I think that data is a mechanism to create focus. Yeah. That helps you focus on, if we can fix this set of issues, we unlock this.

Jimmy Soni
That’s really interesting. Was this common in college basketball at the time? Like, I know you said Tom Izzo is what turned Scott Drew onto it. Had it become commonplace for coaches to hire somebody on their team to do this kind of data science?

Ryan Resch
I wouldn’t say it was common. I think Coach Drew was definitely ahead of his time. Tom Izzo, ahead of his time. Ken Pomeroy, who’s still a big name in college basketball data, had been around for a few years and he was kind of the one that was known. But this was pre NIL. So this was pre all of the money.

Jimmy Soni
Yeah.

Ryan Resch
I’m like, you want to talk about pre NIL? I got in trouble by the NCAA for buying honey roasted peanut butter.

Jimmy Soni
What?

Ryan Resch
Because I had no idea. So the NCAA was extremely strict pre NIL. And the meals, what classified as a meal, was extremely strict as well. And so we could not provide food under certain conditions to guys because then it would be considered a meal. If they get a meal, it’s an impermissible benefit.

Jimmy Soni
Wow.

Ryan Resch
Oh, it was a whole bureaucracy. I mean, it still is a bureaucracy.

Jimmy Soni
Right.

Ryan Resch
But on a different level. And so, look, according to Baylor compliance, adding honey to peanut butter made it a meal at that time.

Jimmy Soni
Adding honey to peanut butter that a player was going to eat...

Ryan Resch
Yes.

Jimmy Soni
Made what you did impermissible.

Ryan Resch
Yes.

Jimmy Soni
Oh, wow.

Ryan Resch
It’s absurd. Absolutely crazy.

Jimmy Soni
That is bananas.

Ryan Resch
It is. And you talk about, you know, you go back to your previous question about data and logic entering sport, the human component. The bureaucracy of it all is what removes the human component. Whereas the player needs this. Not like, let’s put aside the fact that people just love peanut butter. Like, it’s amazing and I can’t have it in the house. Players need this to recover. They need the sugar, they need the protein, they need the fat. Right? So you are instead focused on this arbitrary definition of impermissible benefit instead of what’s best for the players.

Jimmy Soni
Right. That’s right.

Ryan Resch
Yeah. I think that’s what’s actually removing it.

Jimmy Soni
Right. You know, it’s a bit of a detour, but I am curious, because there are very strong opinions on what the NIL changes have done to college sports. And I’m not well versed enough, so if you could give a little bit of a brief on what has changed. But my own sense as a fan from afar is that today’s, particularly college basketball, because that’s the one I follow, but today’s collegiate athletic environment, it feels like the Wild West. Like, there was just a lawsuit in Colorado that allowed an additional year of eligibility for a bunch of NCAA players. And now all of a sudden men’s college basketball for the year ahead is, it’s scrambled. You don’t know what’s going to happen. You don’t know who’s going to come back, how they can come back, how long they can stay. If you get an appeals court to say one thing, it might change the decision. This could rise to the level of the Supreme Court. What do you make, as everybody who’s been there, what do you make of contemporary college athletics?

Ryan Resch
I find it very hard to keep up with, for all of the reasons that you’re describing, which is there are institutions involved now that we would have never considered. Like, at our time, we’re not thinking about, okay, what is the Supreme Court going to decide on this case? And will that affect whether my player is eligible or not?

Jimmy Soni
Right.

Ryan Resch
The rules there were very clear and I think we appreciated the time. I think that the positive side of it is that these players who have this unbelievable gift and these incredible talents, both skill wise, physically, athletically, all of it, they are now receiving compensation for these things. I think that is, like, an economic benefit and a good thing that is occurring. Where it has gone poorly, I think most importantly where it’s gone poorly, is the continuity of teams. And transfers were a problem pre NIL.

Jimmy Soni
Right.

Ryan Resch
So NIL is name, image, likeness, where you are now paid for your name, image, likeness. And there’s a host of rules around how you can receive your money. But it has led to NIL plus what they call the transfer portal in college, where players can now basically leave teams and schools whenever they want to, put your name into the transfer portal, sometimes in an effort to maximize your NIL.

Jimmy Soni
Yeah.

Ryan Resch
It has led to rapid turnover with teams and makes the coaches’ and the now college general managers’ jobs harder. That job did not exist when I was in college.

Jimmy Soni
There was no college GM?

Ryan Resch
There was no college GM when I was there. We were just scraping play by play.

Jimmy Soni
Exactly. Doing it in the Stone Age.

Ryan Resch
Exactly, exactly. And the turnover of these teams is just so high now, where players are leaving, going to the transfer portal, maybe trying to maximize their cash, whatever they deem the most important. And you lose, like, Duke does lose this period of where you guys had Christian Laettner for years, or, yeah, Jahlil Okafor and those guys only stay, Tyus Jones only stayed for one season. But you still had those faces on the team that you recognized year over year. Baylor was the exact same way. You don’t really have a lot of that anymore. And I think that loses, again, back to the human side of sport, that loses, when everybody’s kind of in the foxhole together playing this zero sum game every night, it’s win or lose. Yeah. That is where those bonds are really formed. Where I can still call the coaching staff at Baylor, or the grad assistants at Baylor, or some of the players at Baylor, and we’ll talk about, you know, what the 20, whatever it was, 16 Sweet 16 at Madison Square Garden, where South Carolina completely dismantled us. Like, we still, you know, talk about that. Right? And you just don’t have those memories, that experience or this camaraderie.

Jimmy Soni
I do have one question on this one. It’s interesting. I think about this just as a casual fan, but also kind of the challenge here is, on the one hand, there were always going to be people who were going to be one and dones, right? Who were going to come in, light college basketball on fire, do their year and then go off and play in the NBA. Even before that, you could skip college altogether and go straight to the NBA the way Kobe and others have done. At the same time, you now have money that’s available to you to be paid to stay in college. Right? So isn’t the argument against what you just said, well, yes, it’s true, people can job hop effectively, or college hop, right, and go from one school to another using a transfer portal to maximize their winnings and earnings. But on the other hand, they’re actually getting paid while they’re in school and thus can stay in school longer, right? And then it’s on the program and on the coach and on the university to make that both worth their while financially and make sure that they feel like it’s a place where they want to call home for X number of years. Right? So isn’t there a little bit of, this actually took some of the, it created the safety valve for the pressure to leave for the league, like, too early or skip school or, like, to be a one and done, because now you could be a two or three and done, right? Or a four and done and still get paid for your time. I’m not well versed enough, but does that argument have any weight?

Ryan Resch
I want to say yes, more so in football. Like, I don’t know exactly what that would look like, but anecdotally it feels like I’ve seen more of those stories of someone choosing to stay in college football. Yeah. And NIL money is larger in college football than it is college basketball. Unless you are at a Duke.

Jimmy Soni
Right.

Ryan Resch
Or a Kentucky. So I think it’s more true in football. I could be wrong on the basketball side of things. I don’t know if it has yet reached the NBA side where, yeah, like, the contracts in the NBA are fundamentally different than the NFL, than the Major League Baseball. Each of these leagues has a very different economic structure. Yeah, the NBA’s is extremely player friendly.

Jimmy Soni
Okay.

Ryan Resch
Very, very strong players association, especially back in the 2010s when they were negotiating those really core CBAs. And the players will get, if you’re drafted in the first round, two years guaranteed, two year team option. But you’ll usually look at all four years guaranteed at some point, and then from there, if you’re a good player, you’re making 20 plus million dollars a year now. So the payoff for college basketball may not be there yet. Or I do think your argument has a lot of merit, is that the onus is now on program building. Right? You need to build a program.

Jimmy Soni
Right.

Ryan Resch
Which is where the Baylors and the Dukes and these other schools who have done it are benefiting, with, like, these brand name institutions who have built actual programs. There’s now a value on that, there’s a premium on that.

Jimmy Soni
Right.

Ryan Resch
At some point this will all be, as things always are, regulated to some degree. There will be more rules in place about how much you can pay under what conditions. Like, some kind of salary cap system. Yeah. So I do think that there is a premium that’s now placed on building an actual program. So if you do have one of these brands like a Baylor or a Duke, there is a lot of value there. Once we have some form of a salary cap system, where I think that’ll happen at some point in the future, marry those constraints with what you’ve described of that program culture building, now you’ve got a more professional sport environment there. How do you build an Oklahoma City Thunder in college basketball? How do you build a Pittsburgh Steelers in college basketball? You kind of need both the economic constraints and the recognition of how valuable those programs are.

Jimmy Soni
Right. Ironically, these deals could lead to people, like, completing their degrees, right? The great irony of this might be that so then every worth the student athlete, right? It really could. Because if you think about it, at some point, all other things being equal, if there is a salary cap system and you are constrained on the economic side, then you would just have, you know, all schools would probably reach, like, theoretical limit of whatever those caps are, then program design and, call it, like, student retention matter a great deal. And if you are a coach that has a history of winning and producing NBA level talent and a culture that people actually want to be a part of, and you are at a school where people want to stay to finish their degrees, you as a player, you’d have serious, if you’re not a superstar, if you’re not a one and done, right, you’d have a serious reason to stick around for four years and earn a degree.

Ryan Resch
Incentive alignment. Yeah, that’s right.

Jimmy Soni
Yeah, I like that. And I don’t know, I’m speaking about it in a total vacuum. I don’t know how these decisions actually happen, but it seems to me to be one of the kind of, I know that there’s been a lot of coverage on it and a lot of back and forth on it, sure, but actually I have found this to be one of the most interesting things to be happening in college sports. That is an economics question and a psychology question and a culture question. Not even a, what does the law say and doesn’t say. Because right now what’s interesting is the law isn’t clear. Congress is being petitioned 20 different ways on it. There are already cases underway. So it is interesting to me to think about what is a player who’s good but not good enough to leave and, like, kind of likes where they’re at, but sees that the grass might be greener on the other side. Right? Like, I wonder how people are thinking about this.

Ryan Resch
I do think that you’re probably onto something there, where it is, incentive alignment will happen at some point, it feels like, in this space. And it probably does benefit everybody in the end. I think right now it’s already so hard to recruit in college sports to begin with.

Jimmy Soni
Yeah.

Ryan Resch
That it has made the jobs of these head coaches infinitely harder. Yeah. Only because there aren’t the economic constraints that are specific right now. And because it’s made it so hard, that’s probably where some of the negative, like, publicity and whatnot comes in. It is interesting, though, to think, like, we’re sitting here today and we don’t bat an eye on college basketball players or football players making millions of dollars.

Jimmy Soni
Right.

Ryan Resch
And that was, I mean, unheard of.

Jimmy Soni
Just a few years...

Ryan Resch
Absolutely unheard of. Recruiting visits had very strict budgets and, yeah, you could only do certain things.

Jimmy Soni
Yeah.

Ryan Resch
It is, it’s wild.

Jimmy Soni
It’s wild. It’s also, I remember when I was a freshman at Duke, when by the time I got to my junior year, senior year, they did a deal with Apple where all the freshmen at Duke for a given year got iPods. And I remember being so mad that I had missed the free iPod window. If I was a college athlete who finished up at Duke after these deals went into effect, so the deals weren’t around when I was around, yeah, I’d be livid. I would be livid because the size is actually significant, life changing amounts for these players.

Ryan Resch
It really is. And that’s why the transfer portal is so active.

Jimmy Soni
Right.

Ryan Resch
It really is.

Jimmy Soni
Right. So now we go, you’re at Baylor and you’re a grad assistant and you are furnishing analytics and insights for the team. How long are you at Baylor? And then tell us how the story gets from there to the Phoenix Suns.

Ryan Resch
I would be at Baylor for two years in chapter two, post PhD. The summer after the first year, I got an internship with the Phoenix Suns analytics department on the basketball operations side. So every NBA team, every professional sports team, more or less, is split between sport operation and business operation. So business operation would be tickets, sponsorship, sales, media, kind of everything you’d think under the business banner. And then the sport operation is building and managing and operating the team. Yeah. I was sent by a classmate this analytics internship in Phoenix. I did not have a plan about what I was going to do, and I told myself, probably the only path forward is in the NBA, because, again, it’s not a huge thing in college basketball. Coach Drew would eventually, like, consider bringing on this position, but he would also push me out and say, “You have to go to the NBA,” when that opportunity presented itself, which I’m very grateful for, because it would have been easy to stay.

Jimmy Soni
Yeah.

Ryan Resch
And I got this internship.

Jimmy Soni
So how did that... Well, walk us through it. How, you know, sometimes these internships don’t just happen. Did you just apply? You applied, you interviewed?

Ryan Resch
I applied.

Jimmy Soni
That was it.

Ryan Resch
Applied and interviewed. And I think, you know, again, it’s funny, it comes back to the communication side of it, I think.

Jimmy Soni
Yeah.

Ryan Resch
Where when I was interviewing with the individual who would hire me, the then director of analytics of the Suns, there was a question around, so the Phoenix Suns were really bad.

Jimmy Soni
Yeah.

Ryan Resch
At this time. So one of the worst teams in the league. There was a playoff drought, and the league was just starting to play faster, shoot more threes, have more space, and the Suns were not doing these things. And the Suns were still playing two centers at the time. And I was asked, like, “What would you look at to show the coaching staff not to play two centers?” Very interesting question.

Jimmy Soni
That’s very interesting.

Ryan Resch
Very specific question. Yeah. And I’m sitting there just thinking about it, and I said, “Is the transition defense really bad?” And the response was, “You’re the first person to answer that.”

Jimmy Soni
Huh.

Ryan Resch
And I said, “Well, we can just show them that, like, where do we rank in transition defense? This combination, when they’re together, is very poor.” Yeah. But it has to come back to the why. Well, the why is that, you know, it’s very difficult to play two centers because they’re, you know, the tallest players typically on the floor, the heaviest players on the floor. And they’re usually not the fastest, they’re usually the slowest. And if you’re playing both in a league that is increasing in pace and speed, and they’re just going to outrun you at some point, like, that’s what’s going to happen. Yeah. And the data was showing that.

Jimmy Soni
Yeah.

Ryan Resch
And so my understanding is that answer helped get that internship. And I was very grateful to get the call.

Jimmy Soni
Just out of curiosity, they had not discovered this on their... You didn’t discover it. You knew the answer? Because that was a very...

Ryan Resch
Well, I mean, it was a guess. Yeah, because I didn’t see the data. I didn’t have anything in front of me. I was just proposed the question.

Jimmy Soni
Yeah.

Ryan Resch
And they had the data. They knew the answer.

Jimmy Soni
Got it.

Ryan Resch
I think what they were looking for, which is a very interesting data interview topic, is, can this person creatively identify something? Can you think, I guess, outside the box of whatever the, I don’t know what other answer there might be.

Jimmy Soni
Right.

Ryan Resch
But I get the internship and I do the three months, maybe three or four months over the summer. In the NBA, so the NBA calendar is July 1 to June 30 every year. So the salary cap resets on July 1. So that’s when you can start signing players again. That’s why the draft is at the very end of June. It’s the Finals and the draft at the very end of the NBA calendar. And I started, I believe, right before the draft. Yeah, it was right before the draft. I did a little bit of work on that.

Jimmy Soni
Yeah.

Ryan Resch
Where it’s just basic, hey, interpret these statistics for these draft prospects. This would have been the summer that the Suns drafted Marquese Chriss and Dragan Bender at 4 and 8 in the lottery. That led into Summer League. I’m sorry, free agency, where we’re just doing, again, what would you value, like, this player’s contract at based on what they’ve done in the past? And I was just sitting in my cubicle, which was just doing that work by myself. And went to Summer League, had a good time. August is completely dead. And that was the end of the internship. And I was fortunate enough that they kept my database access on. So for whatever reason, they decided that was worth it. And I just kept producing work when I went back to Baylor.

Jimmy Soni
Oh, wow.

Ryan Resch
So I was still working at Baylor and I was still doing, like, little side projects.

Jimmy Soni
Oh, that’s great.

Ryan Resch
For Suns analytics, eventually building out the web application that they used in the war room, which is where the draft is held, in Phoenix in 2016. No, 2017. And probably because I just kept doing work, they’re like, “We just feel bad. We know we have to hire this guy.” And they hired me as the coaching analytics person, which effectively meant that I was hired to sit with the coaches, sit on the bench during games, and interpret statistics and data for the coaching staff. So, be that communication bridge that looks at the numbers and then is able to relay what exactly is going on.

Jimmy Soni
Got it. Out of curiosity, because having somebody like you in the background makes a lot of sense to me. Game’s done, the week is long, there’s nothing happening, your day job is looking at the analytics and helping to come up with insights. What does someone like you do in that role when you’re on the bench next to the coaches? Are they asking you specific questions? Or is it just, you know what, Ryan? Yeah, this makes you feel real good. We’ll have you here. It’s really just window dressing. You’re gonna have a clipboard. It’s not gonna have anything on it, but when the camera pans to you, you’ll have a clipboard there.

Ryan Resch
I mean, there are clips of me clapping on my clipboard. I laugh because it’s a little bit of a loaded question in that there is no purpose. Like, you kind of realize it, too, when you’re in the moment where it’s like, all right, it’s first quarter. Team’s taken eight shots.

Jimmy Soni
Yeah.

Ryan Resch
Smallest sample size you can possibly imagine.

Jimmy Soni
Right.

Ryan Resch
I can tell you where it may go. Yeah. If we shoot enough shots, it may look like this and, right, regression to mean may occur. There’s a lot of qualitative maybes and, like, we’re kind of theoretically thinking these things. Yes. It’s not helpful in game. Like, it’s really not. And it goes back to something that I used to talk about with one of our coaches at Baylor, Coach T, where we would talk about, what is the best way to prepare for a game?

Jimmy Soni
Yeah.

Ryan Resch
Because I think maybe FiveThirtyEight, back in the day, did a study of how many decisions an NBA coach makes in a game. Some absurd number. Exactly what you would think. And you can’t, no human can process all of this information in real time. In real time, manage the players, manage the emotion of it all, manage your staff. Like, there’s so much going on in the moment. And what we eventually came up with was, like, you have to have plan A, which is we’re going in with this style of play, we’re going to do this offensively, defensively, our team knows how to do these things. And then you have to have plan B, which is, if plan A fails, we’re moving to plan B. Yeah. And then if you get to plan C, guys, we’re probably done. We’re probably losing. And, I mean, on the data side of it, it goes back to, like, whether it’s qualitative or quantitative information, your preparation needs to be there pregame.

Jimmy Soni
Yeah.

Ryan Resch
Before that ball goes up at 7:07pm. Yeah. You need to be prepared. Right? Like, you need to have a coach or someone behind you that taps you on the shoulder and says, “Hey, our goal was, you know, a three point attempt rate of 40% and we’re only at 35%.” Right? But then a good coach, their next question will be, okay, what’s wrong?

Jimmy Soni
Right.

Ryan Resch
Like, why are we so low?

Jimmy Soni
Yeah. And you’re saying this is happening at halftime? Or, well, after the game is over? Or you’re saying after the game’s over, before the next game, to understand what went on?

Ryan Resch
I think that you have to prepare definitely before. Yeah, no doubt. I think at halftime you have to have a very structured process that you go through. Basically you have, like, 15 minutes. Yeah. Some percentage of those minutes must be devoted to talking to your guys. That’s the most important thing. Some percentage at the beginning must be devoted to, okay, let’s review our strategy and our tactics and our style of play. Yeah. There’s a lot of value that can be done there if you can really refine that process. Obviously the pregame prep is extremely valuable. Right? Postgame debrief, hit or miss. Because it’s so emotional after a game. Like, you are coming off of an adrenaline high, whether you win or you lose, everyone is. So it’s really not the best time to chat right after your game.

Jimmy Soni
But as evidenced by any number of press conferences that go so badly awry.

Ryan Resch
Exactly.

Jimmy Soni
Right? And actually it explains the monotone, monosyllabic responses that a lot of players give to questions. Right? There’s no room for creativity after that kind of thing.

Ryan Resch
There’s not. Like, you’re emotionally depleted. Right? And there’s just, you don’t want to talk, you certainly don’t want to talk in front of the camera.

Jimmy Soni
Right.

Ryan Resch
And it’s the in the moment data assistance that I think is, having literally done the job, I don’t think that there’s a lot of value that it’s going to create, because what you should be focusing on instead is training your coaches and the people making decisions in game how to think this way.

Jimmy Soni
Yeah.

Ryan Resch
So instead of me being like, “Hey, we’re not shooting enough threes”...

Jimmy Soni
Your coach, who is in church: “Get back to your cubicle.”

Ryan Resch
Right, exactly. Instead of saying that, you have a coach who says, “Hey, my job is the offense. I know what our threes should look like. I know how they’re generated and know what quality looks like. We are not getting enough off ball screen threes.”

Jimmy Soni
Right.

Ryan Resch
We’re just not.

Jimmy Soni
Right.

Ryan Resch
And that is useful information that helps the coach and helps the players. Whereas, “Hey, we’re not shooting enough threes” is not useful information. That’s a fun fact.

Jimmy Soni
Great. That’s a super fun fact. When you come into the organization, you know, as you mentioned, the Suns were coming off a bad stretch and there was a leadership change. There was also an ownership change. Can you talk a little bit about what it was like being a part of that? Because, so you finished up another year at Baylor, you’re doing all the side hustle work for the Suns. That is what it was. They hire you based on the strength of that side hustle work and then you join them. But you’re in the middle of chaos. Right? I mean, it was, the GM changed and the owners changed. So it was...

Ryan Resch
That changes constantly.

Jimmy Soni
Yeah.

Ryan Resch
I can tell you that it was the exact opposite of what Baylor was, which, I mean, Scott Drew is still the head coach at Baylor. He’s been there for, I mean, my goodness, 25 years now.

Jimmy Soni
Wow.

Ryan Resch
And Phoenix was on, I believe it was the second coach in two years, and it would go on to be the third and then the fourth. Like, there was a whole host of change on the coaching side. We did go through a basketball operations executive change. So our general manager changed when I started full time. James Jones started, who was the player that I mentioned earlier from the Miami Heat. He had just retired, seven straight NBA Finals appearances, played with LeBron James on all of those teams. And LeBron publicly called him the greatest teammate of all time.

Jimmy Soni
Wow.

Ryan Resch
And I can now attest to why. I love James dearly. And he starts full time the time that I start full time. He starts in the role that I would finish in. So there’s a bit of a, like, a bookend here.

Jimmy Soni
Yeah.

Ryan Resch
And he’s coming from winning championships. I’m coming from Baylor basketball, where we’re second weekend NCAA tournament teams. We didn’t win the Big 12 yet, but we were in the championship game in the tournament quite a bit. And you go to losing.

Jimmy Soni
Right.

Ryan Resch
You go to losing.

Jimmy Soni
Yeah.

Ryan Resch
And it is culture shock.

Jimmy Soni
Yeah.

Ryan Resch
James, I believe in his 17 year career, however long it was, missed the playoffs once. I’m coming from spoils and riches at Baylor.

Jimmy Soni
Yeah.

Ryan Resch
And we just kind of bonded over this.

Jimmy Soni
Wow.

Ryan Resch
This weird culture of losing.

Jimmy Soni
Yeah.

Ryan Resch
And there’s really no other way to say it. And I give him so much credit in that he had the perspective when he took over that, it’s very easy, you hire a GM, you hold the press conference: we’re going to compete for championships, we’re going to play hard, we’re going to do all these things. So easy. Like, you can win a press conference. It’s very easy to win a press conference. It’s not easy to win the game.

Jimmy Soni
Right.

Ryan Resch
Like, those are two very different things. And James came in and his very first strategy, well, on day one, he did, you know, change over quite a bit of the staff.

Jimmy Soni
Yeah.

Ryan Resch
Which I think was necessary at the time. And we became a very small, lean operation. I call this now the Startup Suns, for that period of time.

Jimmy Soni
Why were you not part of the changeover? Because you came in under the old management. Yeah. So how did you manage to stick around?

Ryan Resch
I mean, truthfully, I didn’t have an office. I didn’t have a desk. And James, being who James is, told me, like, “Sit on the other side of my desk and work.” Okay. So we just had a really strong relationship from that. He’s also a very rational thinker. He loves data, he loves technology. But he also understands that human component to such a degree as well. And he’s an unbelievable teacher, I think, too. And if you’re willing to learn from him, then you can become one of his people.

Jimmy Soni
Right.

Ryan Resch
But the first strategy that he implemented was raising the floor. It’s not championship ceiling, championship expectations. It was, no, guys, we’re going to raise the floor. Yeah. The floor is way too low. Like, the competitive floor, the talent floor. And this is not just players. And this is the beauty of having a former player as your lead executive.

Jimmy Soni
Yeah.

Ryan Resch
Which I think is so important. Is the individual who has been in those championship games, who has won the title, who has made the threes, who has, you know, defended the best players in the league...

Jimmy Soni
Right.

Ryan Resch
Who understands what these players are going through. They will hold the rest of the organization to that same standard that the players will hold themselves to. And it’s so important. And he literally, he was like, “It’s not sexy, but raise the floor.”

Jimmy Soni
So how did you do that? Like, what are some of the key, both the data and analytics components in your job, but then also just organization wide. How did that happen?

Ryan Resch
You look at age first, and the Suns were extremely young. Yeah, it’s very popular in the NBA to tank. This is another huge thing in sports, is if we lose, then we’ll get a higher draft pick. If we get a higher draft pick, we will maximize our chances of getting an All-Star or franchise player. Yeah. Not incorrect. You know, if you get the number one pick in the draft, then, yeah, you’ll have a much higher chance of drafting an All-Star franchise player from that class than anyone who comes after you. That’s basic logic. Right? What the tanking debate fundamentally misses, because the Suns were publicly tanking and we were there at the very early days and went the exact opposite... What they were missing, the tanking proponents, I should say, are missing the, again, we come back to this, the human factor. Sports is an extremely unique environment. It is the only publicly played zero sum game in the world. I mean, literally everything’s public and there will be a winner, there will be a loser, and it is also time bound. So every year you get one year and then we’re resetting, go again. There’s no rollover effect. You don’t have to carry things over, any of that. When you think about that on a macro level with games, it’s true. But on a micro level as well, where these players, like, we’re drafting the replacements.

Jimmy Soni
Right.

Ryan Resch
It’s crazy when you think about, like, the cycle of this, and it’s arguably, like, deeply unfair as well. Where it’s like, someone who is an NBA player will get pushed out because we’re bringing in this 18 year old high potential. Yeah. And when we talked about, like, James raising the floor, it was finding the value in the older guy. Again, like, finding the value in the four year player, like Cam Johnson, who we drafted at 11, James’s first draft, and we got panned for it.

Jimmy Soni
Right.

Ryan Resch
Cam has since gone on to have an incredible career. He’s a great person, he’s a great player. Like, fantastic.

Jimmy Soni
Yeah.

Ryan Resch
And it’s things like, I mentioned the age. It’s also things like teaching the front office staff what the player is going through when you talk about tanking. Because they hear, “You want to draft my replacement.”

Jimmy Soni
Oh, interesting.

Ryan Resch
“You want to bring in the guy who’s going to take my job away.”

Jimmy Soni
Right.

Ryan Resch
Or the coach hears, “You want me to lose so that you can fire me.”

Jimmy Soni
Right.

Ryan Resch
And then we can continue. And you just can’t, like, it’s so hard to win a championship to begin with. Like, your odds are so infinitesimally small to do this to begin with, that if you don’t realize, like, the consequence of these strategic choices that you’re making, yes, you don’t have a chance.

Jimmy Soni
Right.

Ryan Resch
And this is why, like, Oklahoma City, for example, took you to the tanking process extremely well. I don’t think that they ever publicly called it that, but...

Jimmy Soni
Of course not. I mean, this is one of the curious things about tanking, is you can’t say you’re tanking. If you’re tanking, you’ll get in trouble. Yeah.

Ryan Resch
The integrity of the game. But Oklahoma City, they did an amazing job of keeping their culture so strong. And I give Sam Presti all the credit to that. Like, he is a fantastic executive. Absolutely fantastic. And they built this, you know, this program where it’s, hey, we all know what we’re going to do for the next couple of years and then we hope that we’ll be champions on the other end of it. Yeah. And I think if you do it in that deliberate manner, right, then you definitely increase your chances of success. Yeah. It’s when you do it in kind of the manner that’s, I think we’re supposed to do this because we’re told that you should tank if you’re not good because you don’t want to be in the middle. Right? Like, you know, it comes down to, you understand the strategic consequences of the strategic decisions that you’re making.

Jimmy Soni
Interesting. So when you’re in the day to day of this, how is, I guess, how is the Suns job different than the Baylor job? When you got to that grad-- in both cases you’re looking at analytics, you’re looking at data. What were the differences between those two environments?

Ryan Resch
At face value, the roles were very different post James taking over the Suns. So that was when I became his chief of staff, director of strategy. He would then go on to win the 21 executive of the year. I believe it was 2021. And so the role was more expansive, for sure. Helping out in operations, salary cap if that was needed at the time, traveling with the team quite a bit to basically be a front office presence for them if something happened. Yeah. Whereas, it’s funny now that I say it, it sounds a little bit closer to the manager role, where it was kind of like the catch all situation and just being around to do these things that need to get done. Whereas the Baylor data roles and even those early Suns data roles were very, as you would think they are, behind a computer, looking at numbers, looking at spreadsheets. Thankfully, at that time in the NBA, well, that’s another difference, is the NBA had a much richer data set. So optical tracking data came online right around the time that I was an intern. A company called SportVU, which had installed cameras in all of the arenas, and they could track, I think it was 24 frames a second from six cameras at that time, the XY coordinates of the players directly using the ball. And now it’s XYZ coordinates with Hawk-Eye, which is the new camera provider. And so we were extremely data rich. And so we would spend a lot of time kind of playing in that sandbox of the XY coordinates.

Jimmy Soni
Right.

Ryan Resch
And then as the role increased in scope, it was less of that hands on coding and more of program building, I think, is the way to think about it. And I kind of bounced around. I was very lucky that James trusted me so much. And over the course of my time at the Suns under James, led or managed everything except players and coaches in basketball operations. So scouting at one point for a couple of years, health and performance for a year, operations strategy, so data science, salary cap, those things. Yeah.

Jimmy Soni
So you go from Baylor and doing the data stuff to the Suns at a period of real transition for the Suns. Like, what is different about the job that you were doing in one, you know, in both cases you’re working with data and you’re trying to find insights that are going to help the team. What are the differences between the role in the NBA and the role in college?

Ryan Resch
Kind of at the top level, the NBA is a much richer data set. So when I joined the Suns, this was right around when optical tracking was taking off. So optical tracking was introduced to the NBA through a company called SportVU, which installed, I believe it was, six cameras in the arena, the rafters of the arena, at 24 frames a second, where we could track the XY coordinates of every player, the ball and the referees. And now they can do the XYZ coordinates with the latest technology, which is pretty cool. And so we would spend just quite a bit of time in those early Suns days, not dissimilar to what we did at Baylor, where it’s like, okay, we have our hands on all this data, now let’s build something. And the optical tracking data could produce really cool new metrics. Like, okay, let’s measure how far the screen defender is from the screener, and does that matter if our center is 6ft behind the screen versus 2ft behind the screen? Why does this question matter? Well, at that time, if you’re trying to invite the mid range shot and take away threes, which was the popular style of defensive play back then as teams are shooting more threes, then you want to know, can my seven foot center play at the level of the screen? Does he need to play back? If we do play back, are they going to pull up? Is he going to contest? And there’s a whole kind of, like, chain of thought that goes into that. That’s really interesting. The role itself, though, it grew very quickly under James, and I’m really lucky that he trusted me as much as he did. And I eventually would go on to lead or manage every team within basketball operations outside of the players and the coaches directly. So health and performance for a year, which was athletic training, strength, conditioning, nutrition, sports science, those kinds of things. So keeping the players healthy, getting them stronger, helping them play better from a physical, athletic standpoint. Scouting, which is obvious, professional scouting, amateur scouting, so college basketball. Data science. The salary cap side of things as well, which is super interesting. Kind of ran the whole gamut there. And then eventually my last year ran operations. Yeah. Which was the true day to day of being in it.

Jimmy Soni
So I want to dive in, because, and we’ll link to it in the show notes, but there was this really interesting interview you did about sports and analytics and AI, and you talk a little bit about what happened when data first arrived at the NBA, where you finally have optical tracking data. And then, as I understand it, a company came around and built dashboards. And for the first time, I guess, in the league’s history, this data that, you know, would have had to be cobbled together and, you know, hacked together before is now easily visible to teams. Talk a little bit about that moment, what happened, and kind of what you saw as that happened.

Ryan Resch
Yeah. When SportVU came in and they introduced optical tracking data, it delivered as all nascent forms of data deliver, which is, you know, structured to some degree. But you need to know how to write SQL and you need to know how to write Python or R at a base in order to actually interact with these numbers and make them mean anything of relevance.

Jimmy Soni
Yeah.

Ryan Resch
And, you know, around the mid 2010s too, in the data science community, the tech community, machine learning is really starting to take off. So Facebook algorithms, AlexNet, mentioned previously. You know, it’s insane to talk about it now like, AlphaGo. Right? Like, the things that would then go on to truly change the world are coming into the public conscious. And a company called Second Spectrum, and they did a great job with it. They solved the problem of needing to have technical coding chops to interact with this optical tracking data by building machine learning algorithms to track the actions of these coordinates. So instead of me having to now figure out, okay, a middle pick and roll occurred at 7 minutes and 15 seconds in the second quarter by our players, Second Spectrum built the algorithms, the machine learning algorithms, to actually identify this. And then from there we could split that and filter it into a host of different metrics, whether it’s on the left side of the court, the right side of the court. Basically you’re able to summarize and assess the game at a much more granular level. And they tied film to it. So that was also a huge innovative side of it that again goes towards solving the communication problem. So now coach sees, my middle pick and roll is 1.20 points per possession. And then here’s the 30 clips of our guys doing it. You can reinforce, okay, why is it 1.2? Let’s watch the film to find out.

Jimmy Soni
Right.

Ryan Resch
And super helpful. Yeah. Extremely useful. Very advantageous when you are one of the few teams that has it. But as with all things, it becomes democratized and everybody has access to this data and this information. And something that started happening my last few years in the league was this constant conversation around, is everyone playing the same way? Is there a homogenous style of play?

Jimmy Soni
Yeah.

Ryan Resch
Is everyone running middle pick and roll, trying to shoot threes and either switching ball screens or playing in the deep drop on ball screens? Where is the innovation in our style of play?

Jimmy Soni
Right.

Ryan Resch
And I think it’s a fascinating conversation.

Jimmy Soni
Yeah.

Ryan Resch
And there’s been some studies that say it is happening, some studies that say it isn’t happening. This is one of those topics where, if people are talking about it, if the perception is that it’s happening, then it’s probably important to figure out why that perception exists. Yeah. And it occurred to me one day that we really did all have access to similar data. Right? The same data.

Jimmy Soni
Right.

Ryan Resch
And, you know, you think a program would get, you know, ridiculed if they didn’t shoot, you know, 30, 35, 40 threes. You know, your coach doesn’t have good shot selection, blah, blah. What kind of behavior does that drive?

Jimmy Soni
Right.

Ryan Resch
That the coach now is like, okay, what does the data say I should do?

Jimmy Soni
Yeah.

Ryan Resch
But if you’re basing it off of just what a dashboard says, you’re looking at lagging indicators. You’re looking at what others are doing to win.

Jimmy Soni
Yeah.

Ryan Resch
You’re not drilling down and saying, no, what is it for our team? Back to that two by two. What is it for our team’s context, for how we win? And so when you have this kind of democratized dashboard, instead of proprietary questions, proprietary data, or proprietary metrics built on publicly available data, right, is really the way to do it. With the optical tracking data, you do end up in this kind of path dependency. Okay, middle pick and roll seems to be the most efficient action.

Jimmy Soni
Yeah.

Ryan Resch
Switching ball screens is extremely efficient as well. And then it’s kind of this race toward some kind of false optimization, in a way.

Jimmy Soni
The opposite problem is what many people read in the Moneyball book, right? So on the one end of the spectrum, you’d be like, data is useless. Right? That’s over and done with. Most team owners at this point are going to emphasize the numbers. Right? Now you go to the other place where, because the numbers are the same numbers everybody else is looking at, you get, like, a homogenized style of play, right? Or you’re all doing the same things because the numbers suggest the same things. So that’s an interesting thing to square, whether you’re a GM or a coach, to say to yourself, okay, how do I make sure I’m not captive to the metrics that everybody else is benchmarking against? How did you think about that internally? Like, how did you make the most use of the dashboards that, you know, a company provided, while not then allowing it to drive the same conclusions that everybody else is going to draw, so that you’re basically playing the same game as everybody else?

Ryan Resch
I think it follows a path of what you kind of described, where the information that’s readily available is great for education. It’s great to tell you what is going on. It’s great to tell you what happened. It’s great to tell you, okay, under these conditions, this existed.

Jimmy Soni
Yeah.

Ryan Resch
It does not tell you moving forward, if we face those conditions again, will this outcome still occur? And I think if I could go back, then I would probably emphasize this point stronger with the analytics team, and I would have us just spend more time asking better questions to get us back into the mindset of XY coordinates. How do we build the model that shows whether our center should be 6ft or 2ft or 5ft? Can we get that on what’s available? Yes, but this is different because of how we teach our defense. Like, if we are able to define our shift defense, our help line defense, and we know where these guys are supposed to stand, then we should also be able to code out that logic and get those metrics that are more Suns proprietary or more team proprietary than just taking what is available on the dashboard. Because they don’t know our defense. Right? Nor should they.

Jimmy Soni
Right.

Ryan Resch
And in this, again, it comes back to, I think, like, data is not a holy grail. Like, it is not a panacea for all of this stuff. It is another area where you can find competitive advantage if you know how to use it, just like any other tool. As cliche as that argument is, yes, it is a tool. Yeah, you know how to use it, then you can find advantage with it. And if you do talk to these leagues where it has become kind of more pervasive, like baseball, for example, it’s really hard to find the next differentiation lane of data in baseball, because there’s been 20 years, tons of money, and you’ve had an owner class in Major League Baseball that comes from these more rational worlds that use data in their private equity shops or whatever they’re doing in their business life. And so they almost, like, optimize it to the point where if you don’t have it at an A plus level to begin with, like, you’re just behind. Right? You’re not even talking about eking out advantage at that point. You’re just like, we have... It’s a model that I would use at the Suns, was like, what is the negligence line? Like, if we are below this negligence line, then we must focus everything on getting above it. And if we are above it, now we can start talking about, okay, what are the cool, unique ways that we can differentiate ourselves from this? So you think about, let’s say if we talk about basketball, for example, style of play. So style of play is just literally, how are you going to play offense? How are you going to play defense? What are you going to focus on? Basketball, at the end of the day, just like all sports, is a possession game. You want as many shots on goal as you can get. Field goal attempts plus free throw attempts, you want that number to be higher than your opponent, not in a reckless way. Like, don’t cross half court and just throw the ball up, unless you’re Steph Curry. But you want to just maximize that number. Yeah. So what are the ways to do that? Well, rebounding is one of those ways, and turnovers is one of those ways as well. So either you don’t turn it over, you get your opponent to turn it over, or you grab the ball offensively and defensively, so your opponent cannot grab the ball. It’s really that simple. If you don’t have rebounding and turnovers dialed in, like, if you’re not top 15 in those areas, negligence line would say, focus on that. Focus on defensive rebounding and how you’re going to get better from a roster perspective, from a coaching perspective, from a front office perspective, culturally. How are we going to become a better rebounding team?

Jimmy Soni
Interesting.

Ryan Resch
Before you try to be like, let’s get cute by shooting more threes, like this.

Jimmy Soni
Right.

Ryan Resch
You have to get above the negligence line for your style of play. And so I think that is kind of a helpful model to think about all of these things being tools. When do we start making strategic choices that genuinely differentiate us instead of just having fun with...

Jimmy Soni
Right. Fun with the data.

Ryan Resch
Yeah, exactly.

Jimmy Soni
Yeah. And did you find that, in a way, what you’re describing is the opposite of what the fiercest critics about data in sports would have said, which is, they’re like, it’s going to make the game boring. It’s going to get the game over to eggheads. It’s going to be, you know, bean counters making all the decisions. What you’re actually saying is, no, like, the more information you have, if you’re a bad team, you’re going to lapse into homogeneity anyway. Right? But actually having more information gives you an ability to tailor your particular style of play to your particular opponent or to the group you have. And there’s room for a ton of innovation, even when every movement they’re making has been dissected to the nines.

Ryan Resch
That’s what I believe.

Jimmy Soni
Okay.

Ryan Resch
And I think that is, you know, if humans are just modeling the behavior of other people, at the end of the day, like, teams do the same thing. Programs, institutions, they all do the same thing. So Golden State is going to win all these championships. How do we play more like Golden State? How do we get smaller? Because they’re playing small ball.

Jimmy Soni
Yeah.

Ryan Resch
Well, one of the most important factors of their small ball is they have Draymond Green, who is arguably the smartest defensive player in NBA history. Like, someone who just redefined what it meant to be a small ball center.

Jimmy Soni
Right.

Ryan Resch
And if you don’t have Draymond Green, probably not the path for you to go down. Right? And so, again, if we return to this, like, negligence line model. Basketball is played in a vertical plane. The scoring goal is 10ft above the ground. It’s not like soccer, where it’s, like, low to the ground, you can kick the ball in there. Height and size and jumping ability will always have some level of advantage. So you can’t build a small team in pursuit of playing small ball.

Jimmy Soni
Right.

Ryan Resch
You’re below the negligence line here. Unless you have that defining factor, a Draymond Green type person. And it is exactly what you said, where it’s, okay, if we can get all of this information, as soon as we establish our floor and our foundation. Again, it goes back to James’s model of raising the floor.

Jimmy Soni
Yeah.

Ryan Resch
If we can establish a really high floor here where all of our fundamentals are taken care of. The best coaches will preach fundamentals. Read any John Wooden quote out there. He’s only talking about fundamentals and, like, first principles. Like, you see this in the best tech founders, all of this.

Jimmy Soni
Yeah.

Ryan Resch
Where it is this, like, set the floor really high.

Jimmy Soni
Yeah.

Ryan Resch
Get it there. And then you can start, like, branching off and doing these things. Where you have Steph Curry, who is fundamentally the greatest shooter of all time.

Jimmy Soni
Right.

Ryan Resch
You have Draymond in his role, Klay in his role, Andre Iguodala in his role.

Jimmy Soni
Okay.

Ryan Resch
Now we can start, you know, bringing in these people who can differentiate from there. Or these styles that can differentiate.

Jimmy Soni
So you transitioned at some point from the Suns to your role now in private equity. Walk us through kind of that latest iteration in your career.

Ryan Resch
Like you asked earlier about an ownership change. Yeah. And I like to joke that my NBA bingo card was full except for winning a championship, which is the worst part.

Jimmy Soni
You got to the championship.

Ryan Resch
We got to the Finals. We did lose, unfortunately. And I did go through an ownership change as well. And part of that ownership change, I got to meet Justin Ishbia, who is the founder of Shore Capital Partners. And I spent a lot of time with Justin and with Shore from 2023, when he and his brother bought the team, his brother Mat bought the team, through May of 25, when I did leave Phoenix. And I came to just really appreciate how Shore was built and how Shore was operating. Extremely process driven, very data heavy, very much a sports culture.

Jimmy Soni
Right.

Ryan Resch
In that sports are very much a part of what they’re doing day to day. And I learned so much from them in such a short period of time. Nine years in the NBA is a lifetime. We had done the whole, you know, start from the bottom, get to the top line again. I think one of the through lines of my career has been, like, incessant problem solving. So it is like, just solve the next problem in front of you. And I just wanted a new problem. Like, I wanted a new challenge. And I was very fortunate that Justin gave me an opportunity to join Shore for a year and then recently moving over into 1949 Capital, which is also part of Justin’s world. And it’s been a fascinating look at the difference between the zero sum nature of sports.

Jimmy Soni
Right.

Ryan Resch
And the non zero sum nature of everything else.

Jimmy Soni
Right. And that’s exactly what I was going to ask you, which is, in your prior world, there are winners and there are losers, there are wins and losses. And now you’re in a world, private equity, where there’s still winners and losers, but it’s not zero sum. There are partnerships to be made, there are deals to be made. How have you thought about that transition from one to the other?

Ryan Resch
I would tell you that I miss the games. Yeah. In the sense of, there’s nothing quite like being a part of a winning team in sports. Like, the ride of that.

Jimmy Soni
Yeah.

Ryan Resch
The opposite is also true. It’s extremely hard to be part of a losing team. Right. But what I have really enjoyed about kind of the non zero sum world is what you mentioned, which is, like, you get to finally live out what game theory would tell you, which is cooperation will oftentimes lead to the best outcome.

Jimmy Soni
Yeah.

Ryan Resch
And you get to take these lessons from sport about team building, about setting and raising the floor, about how do different personalities work with each other in the best way, and try to form those partnerships and get the most and the best out of, like, the unit instead of just the individual person. And I’m also very fortunate that, you know, Shore and Justin are very data driven and very AI focused as well. And so the overlap has been that Shore and Justin, in that environment, is very data heavy. Yeah. And very AI forward, I would say, for sure. Shore started an AI team very early. I think it was early 2025 that they started hiring AI specific people to go into the portfolio companies and implement these solutions, which is incredible to think about how early that was. And it was having the opportunity to go to an environment that is that forward looking.

Jimmy Soni
Yeah.

Ryan Resch
That excited me. And helping them roll out a lot of their AI enterprise tools over the last year has been an unbelievable learning experience. Like, tech deployments are one thing, but rolling out frontier models to an entire private equity firm is a whole nother beast. And learned a ton there and have since gone deeper on the AI space and the sports space.

Jimmy Soni
And, you know, there’s that line, like, prediction is always hard, especially about the future. But I’m curious what you make of AI as it has been adopted in sports. Like, where are we at? Are we early innings? Is it far enough along? Because a lot of the things you’re talking about with, like, sabermetrics and all this, did that pave the way for AI use? Is it still kind of where the rest of the world is, which is, we’re figuring ourselves out in this moment? Right? Like, what is the interaction or intersection between sports and AI in 2026?

Ryan Resch
From what I’ve seen, absolutely early innings and absolutely still in this formation of, where are we? Like, what exactly is the impact that this is going to have? So, not dissimilar to what is going on in every other industry. And I think when you zoom back out and you say, okay, who is using AI the best? What can we learn from them? At least in my experience, it’s been, if you think about AI transformation as operations transformation. So operations being, how do we take this unbelievable amount of information that we are receiving, synthesize it and then make a decision on it?

Jimmy Soni
Yeah.

Ryan Resch
And that can happen at a very small level, such as, how are you going to stock the snack bar at your office? All the way up to a very, very high level of, where are we going to move this capital so that we can invest it? If you think about it in that way, then you can start to identify places where having this, I don’t want to call it a logic machine, but this ability to extract structure and synthesize information and pattern match at a scale that we have just never seen. Once you can start finding, like, the links in your chain of operations, be like, okay, this looks like data extraction for the snack room, because we need to have a better sense of how much money we’re spending on whatever, you know, yogurt or whatever, structured in that way. And then AI can help you there. I think that sports is still trying to figure out what that operations chain looks like.

Jimmy Soni
Right.

Ryan Resch
And do I think that there are coders out there who are using Codex and Claude Code?

Jimmy Soni
Of course.

Ryan Resch
And they absolutely should be doing that. How do we now take that capacity and get us back to getting our hands deep in that raw optical tracking data so that we can build new novel metrics, so that we can just answer more novel questions? Like, my whole thing on tanking, where, you know, I think that there is probably a paper waiting to be written by someone who can examine, you know, the kind of perverse incentives of tanking as well. Where, if you were only considering it from the perspective of the general manager trying to acquire an All-Star, yeah, sure, you might have found, like, an equilibrium there. When you consider it from the perspective of players and coaches and owners who need to look good in the community, yeah, maybe it’s a very different calculus. There’s not enough time or attention within a sports team to do that because it moves so fast, because we are on a clock. Every year it restarts. But now that you have AI, like, a good ownership group should be asking, okay, you think that we should tank? Model that for me.

Jimmy Soni
Right.

Ryan Resch
Like, actually run through all of the different scenarios of where this could go well and where this could go wrong. All the way down to, when you think that we’re going to be contending for the number one pick, who’s in that class? And are they Victor Wembanyama roles of generational talent?

Jimmy Soni
Right.

Ryan Resch
Because that is a different proposition than, you know, if you’re just some kind of run of the mill class.

Jimmy Soni
Right.

Ryan Resch
But my hope is that is where AI and sports will get back to, is now that we have the ability at a much lower cost to ask these deeper questions instead of just trying to win the game in front of us. Yeah. We can just produce more novel insights and more interesting ideas.

Jimmy Soni
It’s one thing to be in the front office and doing this. One of the things that AI has done is it’s democratized the ability to ask these questions without knowing how to code in Python or in R or whatever. Do you think that we’re going to see the first generation of players who dive into their own data or into sports data to understand the game?

Ryan Resch
You know, it’s funny, we traded for Chris Paul.

Jimmy Soni
Yeah.

Ryan Resch
And he was a heavy user of Second Spectrum. And I was very impressed by that when I saw that. And it makes sense when you think about how Chris plays. And I have an immense amount of respect for him. He was incredible for us. And some of the best players, you think about James and his career, these players understand themselves. They understand truly their strengths and their weaknesses and they understand what to focus on in practice, what to focus on in warmups. It is very dialed in to a degree that it teaches you the importance of specificity and detail when you watch how these best guys work. And data can help them with that. Yeah, it absolutely can help them with that. Where it’s not, you know, it’s not so much, okay, the front office may use it against me in contract negotiations.

Jimmy Soni
Or somebody’s forcing somebody, like, Ryan, kid Ryan shows up with his glasses and whatever, he’s got his spreadsheet and he’s got his clipboard that has nothing on it, but we let him hang out at the game. He’s telling me something about my spacing when I’m doing a screen. This is like the, you know...

Ryan Resch
Yeah.

Jimmy Soni
It’s more that the player could own this conversation.

Ryan Resch
Exactly. I think that’s what, if we’re moving toward kind of this democratization of information and intelligence, then I hope that is where it goes.

Jimmy Soni
Yeah.

Ryan Resch
Is where the players really understand how they can benefit from it.

Jimmy Soni
Right. So if we take ourselves outside of the work context, and, you know, I want to be respectful of your time, want to wrap up. When you’re thinking about AI right now, what have you personally been most impressed by? Right? Because you came of age in a profession and in day to day work where you were taking huge amounts of data and trying to wring insights out of them. So what’s most exciting to you, or what tools do you use? What’s your day to day interaction with AI like?

Ryan Resch
I don’t know if this will be an exciting answer, but I think the thing that I am most interested in right now is using these coding agents with my workspace. Workspace I would have previously called a working directory.

Jimmy Soni
Yeah.

Ryan Resch
Someone can call it a repo, whatever they want to call it. But having my workspace now be designed not for me to read.

Jimmy Soni
Yeah.

Ryan Resch
But for agents to read, for agents to navigate.

Jimmy Soni
Yeah.

Ryan Resch
It’s been such an interesting problem to solve. Okay, Ryan is not navigating this as much as he otherwise would have been, like an old Dropbox setup. Right? Ryan is building agents who need to read the work of the other agents, or what they’re producing and what they’re writing to this workspace. Yeah. And that is two very different things.

Jimmy Soni
Yeah.

Ryan Resch
And I have torn it down, last month I think I’ve torn it down four times and rebuilt it. I have more copies of a working directory than I ever thought I would have. But I think that speaks to kind of the age that we’re entering also, which is you do have to change your perspective of how you used to approach work fundamentally.

Jimmy Soni
Right.

Ryan Resch
And I think it maybe makes me a better manager of people, to be honest, because you have to be so much more specific in what you’re looking for and asking for. Maybe not five years from now when these models are even better.

Jimmy Soni
Yeah.

Ryan Resch
But again, not an exciting answer. But I think, like, redesigning what your literal workspace digitally looks like.

Jimmy Soni
Yeah.

Ryan Resch
Fascinating. And then day to day, it’s really become an operating system, where I love to write. So, yes, I will still open up Word or whatever, but I don’t really type my writing anymore. I will hand write writing, and then I will build, like, work product writing.

Jimmy Soni
Oh, wow.

Ryan Resch
With Codex or with Claude Code or something like that.

Jimmy Soni
Yeah.

Ryan Resch
It’s very interesting where these worlds are diverging, where professionally I am living very much in these tools as an operating system, and in my personal life, going back to, like, this analog...

Jimmy Soni
The old school.

Ryan Resch
Yeah, back to the analog. Very interesting.

Jimmy Soni
I think that divergence is only going to become sharper. Right? I think it’s going to be, you have this world that you step into that’s almost quasi like the Matrix. But unlike the Matrix, you can pull the cord out of the back.

Ryan Resch
Exactly.

Jimmy Soni
And you do daily, because it’s the only way to stay sane.

Ryan Resch
Yeah.

Jimmy Soni
Right? It’s the reason, we talked about this a little bit earlier, before we were recording, but it’s the reason live events, like the premium on live events, is going to go up. I think it’s ironically the race to the new in AI is going to race many people back to the old. Right? And, like, the things that may have been under indexed in the social media era, I think, because of AI, are going to be over indexed in the next wave. Because I think what’s going to happen, you’re going to be too digitally plugged in. And the relief that you feel when you’re not... Right? The relief I feel now when I read a book, it only rivals what it felt like to read as a kid. And I think that’s entirely because so much of my day is spent in different AI modes that reading a book feels like Christmas. Like, it’s incredible to have the analog experience again.

Ryan Resch
I completely agree with that. I mean, I’m sitting here wearing a $20 Casio watch from Amazon because I did not want a smartwatch. Right? I did not want to wear it and be constantly hooked into these AI tools. Yeah. And it’s interesting because I think I could not have vocalized this in sport, but I can vocalize it now, which is, I love any work where you have to perform. Sports is that, where there’s a performance every night. Hospitality, restaurants, hotels, you have to be on. You have to perform. Broadway, here in New York, where we’re recording this, you have to be on. And I think that element of, someone is going to rehearse, rehearse, practice, practice, and then the curtain is going to go up, the ball is going to go up, the restaurant’s going to open. What an unbelievable thrill that was going to be for, I mean, for people to attend it, to see it, to see that level of talent, but then also to do it, do that work. I don’t think I could have explained that when I was in sports, but I feel that way now.

Jimmy Soni
Right. I think the premium on it goes up because fewer things will become unpredictable. My theory of the case would be that because you don’t know the outcome of how the night’s going to go in a show or how the game’s going to go. Yes. And I can give you very good predictions about most everything else.

Ryan Resch
Right.

Jimmy Soni
Like, it’s going to work from the available set of human data and restrictions and come back with an answer. The sheer unpredictability of some of these things is what’s going to drive the desire for them. Right?

Ryan Resch
Yeah.

Jimmy Soni
Yeah.

Ryan Resch
Randomness is good for us. Right? It turns out.

Jimmy Soni
Right. Exactly. What are some of the, and I promise we’ll finish here, but because we could do this for another three hours, this is basically like what we would do anyway. What are some of the books or podcasts or kind of other media or intellectual influences that this year have helped you, particularly as you’ve made the transition from out of sports to private equity?

Ryan Resch
I read a lot, so I absolutely love to read. Like you, whenever I am reading, I am extremely happy. From a fiction perspective, a mutual... Tyler, a mutual friend of ours, recommended on his website when Dan Simmons passed away, the Hyperion series. And so I did read Hyperion and then I am in the fourth book now, and it’s fascinating to read that, to go back and read some of the other science fiction classics and see how they talked about AI at that time. Deeply philosophical. Not an accident that Silicon Valley in the tech space right now has that slant and that bend to it as well. But I think that has helped me in a way contextualize, maybe societally, like, not so much where it’s going and, like, oh no, things are going to go so poorly, but where things are, like, culturally. Has been really interesting. I am still a huge fan of memoirs and biographies, as you know. So I gave your book out to many people at the Suns. Jimmy came and visited and saw stacks of The Founders. I would give out to the team. And I continue to find myself drawn to those stories more and more. I don’t know, I’m kind of processing this now as we’re talking about it, but I think it’s like reading these stories of these people who accomplished such unbelievable things pre AI.

Jimmy Soni
Pre AI.

Ryan Resch
Yeah. Like, how did they think about these problems before we had the ability to, like, drill down or synthesize all of these random things? Like, how did Steve Jobs approach that? How did, you know, past presidents, how did historical figures solve their problems in an era where it was just much more difficult to see the board clearly with the information that you had access to?

Jimmy Soni
Yeah.

Ryan Resch
What I do really enjoy is the podcast and the media landscape that this industry has birthed, with shows like TBPN. Yeah. And just how much fun people are on space. Or even things like the Dwarkesh podcast, where it’s, no, we’re going to go super deep on these... Kind of 10 years ago we’d have been like, what are we all talking about? But now that we have direct application to KV caches in our life, like, I do want to watch a whiteboard session.

Jimmy Soni
Right.

Ryan Resch
It’s at the point now where I wish I had two more hours in a day...

Jimmy Soni
Same.

Ryan Resch
So that I could read or listen to a show or any of that more.

Jimmy Soni
Yeah. Because the issue is that a whole new category of media has opened up.

Ryan Resch
Exactly.

Jimmy Soni
And it’s so different from the media I had when I was growing up. And it’s so rich, it’s so protein rich, and I just don’t have the time.

Ryan Resch
I agree.

Jimmy Soni
And I do not know from where I will find the time.

Ryan Resch
Exactly right.

Jimmy Soni
And the truth is, it’s like, I don’t know if you felt this way, but I know people have their different opinions about AI. I have found it to be just the most exciting thing to me since I kind of, like, first got on a dial up Internet, to make sure my parents didn’t pick up the phone by accident, interrupt that phone signal so I could interrupt the Internet. It’s that exciting. Because I think, especially if you’re in any kind of creative space, or if you’re in any kind of space where there’s a lot of flux, like what you’re in, where things can go one way or they can go another, AI just, it opens up the universe of possible questions you could ask and begin thinking about in a way that I have never seen. Like, I find myself, what it’s done for me, in addition to, I think, making me a better manager, it’s also made me ask better questions now, because that is just good training for the LLMs. It’s good training for life.

Ryan Resch
I completely agree with all that. There is, like, a default optimism, I think, that I have on these things. Recognizing the risks that exist, obviously. But I think the story of humanity and society is one of progress. And, you know, when you really look back at all of the technological change and the progress and the way that we spoke about those things at the time, there are a lot of overlaps there. I just feel so lucky to be in this. You tell me, when I was, like you said, I consider myself lucky being probably the last generation of millennial that did experience the analog to digital shift. So I did have a CD player. Despite how young I look, I did have a CD player. I also remember Napster.

Jimmy Soni
Yep. Napster was, that was the whole ball game. Finding out ways to download those MP3 files.

Ryan Resch
iPod with the click wheel.

Jimmy Soni
Right.

Ryan Resch
God.

Jimmy Soni
Really dating ourselves here.

Ryan Resch
This is funny. I know.

Jimmy Soni
The funniest interactions I have on these is, I have an 11 year old and she doesn’t realize the digital bounty that she’s been given. Right? She has no idea. So I remember one day we were talking and we were, she was like, we were watching one of our shows we like, and she said, “Oh, let’s go to season two, episode three.” And I stopped in that moment. I said, “Do you know that when I was young and I wanted to watch a show like Sonic the Hedgehog, I had to wake up, like, every Saturday to make sure that I was in front of the TV when that show came on, otherwise I would miss it. You’re done. And you have the ability to just pick a season, episode. This is extraordinary.” And she looks at me and, perfectly seriously, with, like, true pity in her eyes, she goes, “That is so sad.” Like, felt deeply bad for me that the challenge of my life was not being able to pick the season and pick the episode.

Ryan Resch
Amazing. Next time you’ve got to show her how to record it using a VCR, but there has to be something on the VHS tape, so she has to erase that first, and then she has to record it.

Jimmy Soni
Oh my God, that is too funny. So one of the ways we like to finish out Infinite Loops is, Ryan, you’re emperor. You’re named Emperor for a Day. And you get to basically incept two ideas, messages, themes, concepts, quotes, into everyone’s mind in humanity. So they’ll wake up and have these two ideas in their head. What two ideas or thoughts would you want people to carry forward into their lives?

Ryan Resch
There was a quote in my office in Phoenix. I don’t know if he actually said or wrote it, but it is from Voltaire.

Jimmy Soni
Right. Voltaire gets a lot of credit for things he didn’t say.

Ryan Resch
But you know what? Like, good for him.

Jimmy Soni
Yeah, right? Like, “don’t hate the player, hate the game.” I mean, maybe that was Voltaire that said that.

Ryan Resch
Maybe he’s living big in the age of AI. And he allegedly said, “No problem can withstand the assault of sustained thinking.” And I love that because it goes kind of like a core principle of mine, which is, just solve the next problem. Just solve the next problem. And if you do that, then you’ll win the game. Or you think about basketball, the defense is going to change. We’ll solve for that defense, because guess what? They’re going to change again. And then you’ve got to solve for that one, and then just keep solving.

Jimmy Soni
Yeah.

Ryan Resch
And I think that it also goes back to the default optimism point, where it is, if we believe that we can solve these problems and we can get around this, we can get around the risks that these, you know, AI tools may or may not pose, for example, I think that would be one. And then the second, and again, it goes back to, I think, a realization that I’ve only had recently, which is try to do work that has to face some form of reality. And what I mean by that is, you’re an author, you write a ton. You have to publish. At some point, you have to stop editing and send that book out so that I can read it and give it to my team. That is facing reality. Sports is that. Every single night, zero sum, someone’s going to win, someone’s going to lose. What we talked about earlier with the restaurant or the Broadway show, like, let people experience the work that you’re creating. Have the confidence for that so that you can get the feedback from it. But also what you’ll find is, when you find your work and when you find your people to do this work, it is so unbelievably fulfilling to do that thing together with those people, to put that thing out into the world, to actually change something or to introduce something to society. I think that’s so fulfilling, and it’s probably why I like reading biographies and memoirs.

Jimmy Soni
That’s a wonderful place to end it. Ryan, thank you so much for coming on Infinite Loops.

Ryan Resch
Thank you.

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We discuss how AI changes the economics of finding needles in haystacks, Effort’s investigations into hidden funding and government spending, whether AI can actually make journalism more rigorous, and what happens when everyone suddenly has the ability to interrogate the information around them. We also explore the darker side of these tools, including AI-powered persuasion, misinformation, cognitive security and the “crisis of nominalism.”

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

How Journalists Source Stories

Brian Chau
The way that journalism is sourced is totally shocking to me. And maybe you’ve been around the block enough that you kind of just know this and have known this forever. But almost all of investigative journalism is solicited. In other words, it’s someone coming to you, the journalist, with a story they want you to run. And I’m not saying that it’s never good, it’s never ethical, to run with a story that’s solicited. Of course, sometimes people come to you with a story, and that’s really important news. It’s genuinely important. And it’s totally a good thing that they run that. And it’s been like that since Watergate, right? Watergate’s famously a solicited story. And it’s been like that actually long before that.

But that actually warps the entire ecosystem of what you see in front of you. And until very recently, it was physically impossible to have stories that came basically any other way. Because to do something like what we’re doing now, in which, for example, we query every single row of the HHS grant table, and that’s how we find a story. And we do that literally, exhaustively, literally looking at the same criteria for all grants, saying, okay, which grants have spiked in the past five years, which grants have grown a ton, either proportionately or as an absolute value, and what relationship those might have to something that’s newsworthy. And I really don’t blame journalists pre AI, because like you said, if you were to do that manually, that would take you literally a lifetime.

And so, just based on the constraints of practicality, not necessarily due to any particular motivation, it was not possible to do that. And now we can have journalism that we source through these exhaustive investigations into legal and financial records, and we can actually have a more scientific way of approaching these things, where it’s like, okay, here are the data sources that we’ve searched. Here are the prompts that we used. Here are the results that we have. And here are the investigations that we tried to do and that we actually hit a brick wall. We didn’t. We found nothing.

A Conspiracy of Incompetence

Jim O’Shaughnessy
We all love our priors, and that turns us into confirmation bias machines where we literally are blinded to information that conflicts with our priors. So let’s just say that’s the average voter, right, if we keep this in the political realm. So an unkind term would be low information voters, right? And nevertheless you could make, I think, I’m asking you really, I think you could cherry pick real facts, not “I made it the fuck up”, but real facts that are verifiable in, let’s say, one of these many government data sets or private data sets or whatever, and you could turn that into an incredibly persuasive story […]

By the way, I’m amused by most conspiracy theorists, because the real conspiracy is there really is no conspiracy except in filing.

Brian Chau
Yeah, it’s a conspiracy of incompetence. My least favorite phrase in the entire English language is “do not attribute to malice what can be attributed to incompetence.” Because if you’ve ever spent a moment in the real world, you would know that the most malicious people are also extremely incompetent. And very often incompetent people are also malicious. It’s not mutually exclusive. And yeah, I think you’re totally right

Edited Transcript

Jim O’Shaughnessy
Well, hello everyone, it’s Jim O’Shaughnessy with yet another Infinite Loops. I am very excited to have Brian Chau, the founder of Effort News, an innovative open-source investigative journalism site, on as a guest today. Brian, I love this idea so much. We have our own on-prem AI installation, hardware, support software, models, that we use, and this was one of the ideas, and you beat us to it. So congratulations.

Brian Chau
Thank you. It’s been really surprising, both the stories that have gone around and people just didn’t investigate at all, and the underlying infra. Because people have been talking about AI and journalism for basically as long as I’ve been around. This is pre ChatGPT, people are talking about AI and journalism, and just no one has done it to any effective degree at this point. I think everyone tries to do AI for writing, right? Everyone tries to make AI write the articles. And I don’t know if you’ve noticed this, but when AI writes the articles, they are just terrible. They are utterly terrible. And no one has really made a dent in using AI to investigate these troves of legal and financial documents, which is what we’re doing, and we’re changing that.

Jim O’Shaughnessy
So for listeners and viewers who are not familiar with your new endeavor, explain exactly for our listeners and readers what you’re doing, why you’re doing it. I know that I’m a huge fan of tech making things possible that were impossible before, right? So the first book I wrote was called Invest Like the Best: How to Use Your Computer to Unlock the Secrets of the Top Money Managers. And it was literally, hey, no human being can go through the 1600 annual reports of every company that get released on a quarterly basis. But it’s trivial for a computer to do that. That was way back in the 90s. Now we’ve got the supercharged AI. It can go through tens of millions of records. But talk about A, what was the motivation, B, how you put it into practice effectively. And another thing I really want you to comment on is something that I love, and that is you published the null sets. I think that’s really, really important.

Brian Chau
Yeah, it’s really shocking even before you get to the null sets. The way that journalism is sourced is totally shocking to me. And maybe you’ve been around the block enough that you kind of just know this and have known this forever. But almost all of investigative journalism is solicited. In other words, it’s someone coming to you, the journalist, with a story they want you to run. And I’m not saying that it’s never good, it’s never ethical, to run with a story that’s solicited. Of course, sometimes people come to you with a story, and that’s really important news. It’s genuinely important. And it’s totally a good thing that they run that. And it’s been like that since Watergate, right? Watergate’s famously a solicited story. And it’s been like that actually long before that.

But that actually warps the entire ecosystem of what you see in front of you. And until very recently, it was physically impossible to have stories that came basically any other way. Because to do something like what we’re doing now, in which, for example, we query every single row of the HHS grant table, and that’s how we find a story. And we do that literally, exhaustively, literally looking at the same criteria for all grants, saying, okay, which grants have spiked in the past five years, which grants have grown a ton, either proportionately or as an absolute value, and what relationship those might have to something that’s newsworthy. And I really don’t blame journalists pre AI, because like you said, if you were to do that manually, that would take you literally a lifetime.

And so, just based on the constraints of practicality, not necessarily due to any particular motivation, it was not possible to do that. And now we can have journalism that we source through these exhaustive investigations into legal and financial records, and we can actually have a more scientific way of approaching these things, where it’s like, okay, here are the data sources that we’ve searched. Here are the prompts that we used. Here are the results that we have. And here are the investigations that we tried to do and that we actually hit a brick wall. We didn’t. We found nothing.

Jim O’Shaughnessy
Yeah. And I love the nothing, because learning via negativa is something that is not natural to we humans, right, for the most part. I was a big Sherlock Holmes fan when I was a kid, and I remember the story.

Brian Chau
Did you want the Sherlock Holmes cold cases?

Jim O’Shaughnessy
Yeah, yeah. And I always loved the story where he knew that the intruder was known to the family because the dog didn’t bark. And that’s something people just have a hard time getting their heads around, right? All of the null cases that sound very enticing, or like a motivated reasoner could say, well, of course there’s a conspiracy, well, of course this is going on. And then null says, yeah, we scoured 100 million data points and we’re not finding anything.

I wonder though, is, you mentioned a traditional journalist will generally look to sources, right, and then basically go try to either confirm or deny what the source is telling them. Here the sources are a cornucopia of documents that have been required for filing for public information, et cetera. What about situations where there are very little reporting requirements, and/or, for example, the size of the offshore empire, I call it the empire of elsewhere because of the way it gets cleared through the City of London but settles in jurisdictions that used to be part of the British Empire but have very lax financial diligence and paperwork requirements. How do you get into things that aren’t in a Freedom of Information, or aren’t one Freedom of Information Act request away?

Brian Chau
I want to acknowledge that there’s a lot of truth in what you’re saying, but also a lot of the time these barriers are more paper barriers than you might think. So we had one story where we uncovered the donors behind this degrowth organization in Europe called Partners for a New Economy, P4NE. And what we did there is that they were actually hiding their money. It’s funny enough, this degrowth organization calls for an end to growth, shifting of economic policies away from prioritizing growth. Who are they funded by? They’re funded by these 19th century European heirs who are hiding their donations through literal Swiss bank accounts. So they had this big, essentially money mixer, legal version of a money mixer, called Swiss Philanthropy Foundation. And what Swiss Philanthropy Foundation does is that it fiscally sponsors 106 different, essentially like NGOs.

And whenever anyone makes a donation to any of the 106, including the degrowth organization we are investigating, on paper that’s a donation to Swiss Philanthropy Foundation. In theory, no one knows who it’s going to. No one knows if it’s going to P4NE or anyone else or any one of the 106 different foundations that they have in there. So how did we crack this case? We ended up using those donation rows to trace back the donor side disclosures. In other words, in a lot of cases, even if P4NE doesn’t have to disclose their donors because technically it’s being done through the Swiss Philanthropy Foundation, a lot of the time the donors have their own disclosures that they need to do, and you can go line by line and see what matches, and then go to the donor rows and then see if they have a record for those same transactions to Swiss Philanthropy Foundation. And that’s how we traced back a lot of the donors to P4NE.

So there’s both cases where you’re right, there’s more of a layer of obscurity. But I think there’s a big juicy middle there, where there’s a lot of obscurity that does enough to obfuscate you from traditional journalists, or from people who are just doing it by hand or just doing it using traditional software, and from some of the tools and the search mechanisms that we’ve unlocked at Effort. And I think that’s true on a national and also an international level.

You mentioned routing offshore. We know where a lot of these accounts are filed. A lot of them are Hong Kong, a lot of them are Dubai. A lot of them are kind of like vaguely Saudi related accounts. I don’t know if I’m saying anything I shouldn’t on this, but this is all pretty well known, and they’re well known operators that will teach you how to do it as well. And I think that there is a lot more to uncover there. Maybe that’s not the ideal, maybe that’s not the pinnacle of 100% transparency, but I think just as a practical effort, we can put together a lot on that front still.

Jim O’Shaughnessy
Yeah, I’m finally writing a fictional novel that I’ve wanted to write. I had the idea for it like 34 years ago and I’m finally writing it. And we’re using a very experimental technique where we have a writer’s room. It’s me generating all of the story and all of the ideas behind it. But then the writer’s room is like, yeah, Jim, this doesn’t make any sense. And how do you ever think about that? It’s the way a lot of TV shows are produced.

Brian Chau
Yeah. I was just about to say, yeah, you’re writing the Seinfeld sci-fi novel.

Jim O’Shaughnessy
We are actually putting AI editors and writers into the writers room too. So I’m a big believer in the centaur model, which is man plus the tool, right? I look at AI as just an incredible tool that empowers us, we humans, to make the story better, et cetera. One of the things I bring that up because, as I mentioned, if you...

Brian Chau
Can I ask, how well is that going? I think a lot about using AI to improve my writing. And I’ve not really gotten anywhere with this. So I’d be curious on how that’s going with AI editors.

Jim O’Shaughnessy
The editing, certainly on copy edits, it is virtually perfect. On fact checking now that hallucinations have gone way down. Again, it’s difficult because we have our own on-prem which has been fine tuned for the things we’re looking for. So we’re not using just a commercial model off the shelf. And so it’s also very good at that.

On the writing, it’s a very good critic of writing, but that’s up to you. By that I mean you’ve got to come up with a prompt where you get rid of all the sycophancy, where you get rid of. And so I came up with one that was like, I want you to embody one of the most erudite, well-read critics, and I want him to hate everything that I’m going to put in front of him. And oh man, did that hurt. And the thing that is really interesting is it caught things that I would not, and my human writing team and editors also missed. Like, oh, we didn’t even think about that. So it’s really good at all of that. On the writing side it’s getting a lot better. But what you want it to do is you just have to constantly reinforce, no, this is not the voice. This is not my voice. Sorry, gone. But I suspect that as it goes along it will improve dramatically.

But the point I was going to bring up was, as now, remember, this is a fictional novel, but I run it through not only a panel of experts that we generate. So if a chapter happens to be about offshore accounts, we spin up expert panelist members who are expert in that particular thing. We spin up experts in the City of London and the Remembrancer, and on the Bank of International Settlement, et cetera. And then the reasoners are the ones that check all the facts. And we use an adversarial system there. We have one group of agents saying this is true, and we have another group of agents saying, no it’s not, and here’s the evidence.

But I ran a fictional chapter through it just recently and it kind of blew me away, because remember, this is fiction, but it’s looking for the facts around the town I’m using, right? And it comes back, one of our villains starts a terrorist campaign in Europe, and one of the things that is part of that is an electrical grid attack, right? And the AI came back with, yes, that actually did happen at that particular time. But what you maybe didn’t know was the family that electrified that town in this particular country, they had their own house on top of a hill that they had their own electrical system built for. So even if the entire town went black, their house would still be lit up. And I’m like, wait a minute. And so I went the traditional route and went and found the paper records and found all of that. I’m like, damn, it was right. So I suspect that in what you’re doing, you can find all sorts of similar items that don’t intuitively appeal to us.

Brian Chau
Yes. And there’s all sorts of things that become notable via the combination of information. The most obvious example is plagiarism, which is now in the news for other reasons. But you have one person write a thesis, that’s no big deal. You have two people write the exact same thesis, now that’s news. And it’s a lot like that for these entire categories of crimes or of newsworthy findings. Take fraud, for example, right? You have one ledger that’s just all of the expenses. Okay, that’s like, maybe you can look at that and say, oh, they’re paying too much for these services, they’re running inefficiently. Okay. But it is another level of newsworthiness if you have two ledgers, one for the people who are getting paid and one for the people who are paying, and they don’t match. Now that’s an entire different category of information.

Jim O’Shaughnessy
Yeah. And one of the things I thought is, the old way of doing things was a reporter would start with a hypothesis, and then he or she would go and try to find evidence in favor of that hypothesis and, ideally, information that was at odds with that hypothesis. But aren’t the prompts you’re using, isn’t this just like your prompt is your hypothesis?

Brian Chau
No, I think that is true at an abstract, philosophical level, and I think that is less true in practice, where there are degrees to this. For example, when we found the Office of Refugee Resettlement grant story, this was our biggest story at like a hundred, or sorry, it had a million and a half views on Twitter. The prompt that generated that was something like, I had at that point already set up the infra to efficiently fetch and create a mirror of the HHS grant table. But it was, search this database, identify any newsworthy findings, transactions, or evidence of wrongdoing. Look carefully for rapid jumps in absolute and relative values of grants, and cross reference that with other investigative reporting or legal findings.

And what we ended up finding was something that was very specific, was related to these particular religious charities, which claim to represent the viewpoints of religious Americans, both Catholic and other Christian and Jewish Americans, but really had the vast majority of their revenue, 81.8% in one case, coming from these federal migration services grants. So I know a lot of people with different perspectives. You can have whatever perspective you want on refugee resettlement, but the organizations that are moral arbiters for this issue should not be organizations that are actively profiting from these federal grants. They can provide those services or they can be the commentators, but that’s a clear conflict of interest.

But the way that we got these stories was with this open ended query. And in many cases the open ended queries are just more effective. They are just better. And it’s a way that the information flows are shaping the direction of journalism, I think for the better. Because if I set out and I’m like, okay, find me fraud in daycare centers ahead of time, and that’s all I say, then I probably would have missed the story. It’s not overtly fraud. It’s technically legal. It’s not in daycare centers, obviously, it’s in a different funding stream. And in this case, actually having a more exhaustive and more expansive prompt at the start leads you to having a higher likelihood of finding a newsworthy story.

And that is something that is inverted from journalism in the past, where in the past it would almost always be the case, just because of the sheer effort involved, the sheer human quantity of time and labor, that the more narrow your hypothesis, the more likely you were to get somewhere quickly. And that is just the opposite of true at this point, at least in our experience. And I think that this will have a permanent reshaping on what stories end up getting published.

Jim O’Shaughnessy
Okay, so let me ask a question. Imagine we gave your harness and your models to a highly ideological person. And it doesn’t matter what extreme they’re on. Okay, so they’re either a communist or they’re a mega free market type, right? And they were able to run a million queries against a government database. Couldn’t they construct an extraordinarily persuasive but misleading story using only actual factual data that they cherry picked from those government databases?

Brian Chau
I think that’s true in theory, but I think that’s a better equilibrium than what we have now, right? The equilibrium that we have now is basically the “I made it the fuck up” equilibrium, right? It is, you know, all these stories about data center and water usage. It’s like, the real number is like 1%. Of what? Of what? Like, or the real amount is like 1% of total water usage. It’s less than 1%. It’s like a fraction of what, like almond farmers alone?

Jim O’Shaughnessy
Pistachios.

Brian Chau
Yeah, yeah. If you ask me, like, okay, for Lent, you have to give up everything that you use data centers for, or you have to give up almonds. What would be the harder choice? And it would obviously not be almonds.

And it was this incredibly effective campaign of not even laundered, like, misconstructions, necessarily. You could call them misconstructions, you can call them misreadings or misrepresentations of denominators, but really what they were was, there was this one author who basically made it the fuck up and was promoted by the New York Times, was promoted by all these journalistic institutions who clearly had a story they wanted to tell and was grasping at straws in order to tell it.

And I think it’s in theory possible that they could do the same thing using the tools that we have. But in some sense that would be a restraining force, not an amplifying force. And here’s what I mean. We end up making literally hundreds of falsifiable claims when we set out. And actually not even falsifiable claims at the level of, here is the actual amount of water a data center uses, but falsifiable claims in that we’re saying, here is this financial record that is proving what we said, and here’s the link to that record. And really, if we were just full of slop, if we were just making shit up, then you could click on those links and you could verify that and you could very easily dismiss us. You could very easily generate this kind of reputation obliterating point, which is like, oh, you claim to have found this invoice, but actually this is just completely fake.

And that is actually something that has happened in some cases when it comes to either defendants or lawyers, defense attorneys, or attorneys in general, making ChatGPT hallucinated citations, or other news stories. Or famously, in the Nathan Cofnas case, the person who suspended Nathan Cofnas had this university speech which made up quotes by people like Albert Einstein. And apparently this was because that person used, this is Petra De Sutter, used ChatGPT to write the speech, which itself is a little bit suspicious, I think, because if you’re doing that with modern ChatGPT, it will not fabricate quotes so brazenly in that way. I almost think it’s some kind of deflection.

But it’s this information ecosystem where it is the “I made it the fuck up” information ecosystem, and there are all sorts of historical institutional legitimacies that are basically tied to the practice of making things up at the moment. And also, to be fair, a lot of new institutions or just influencers or whatever who are tied to making things up. And I think that when you get to the systematic production effort of actually trying to verify and source and evaluate large scale records, that imposes a discipline on you that doesn’t make it impossible, but that just by having this quality filter makes it less likely that’s the kind of story that you’re doing.

Jim O’Shaughnessy
You make a very logical argument. But the fact is we live in a world where a lot of people are very busy, they have their priors, and we all, myself included...

Brian Chau
Yeah, I love my priors, I’m a huge fan.

Jim O’Shaughnessy
We all love our priors, and that turns us into confirmation bias machines where we literally are blinded to information that conflicts with our priors. So let’s just say that’s the average voter, right, if we keep this in the political realm. So an unkind term would be low information voters, right? And nevertheless you could make, I think, I’m asking you really, I think you could cherry pick real facts, not “I made it the fuck up”, but real facts that are verifiable in, let’s say, one of these many government data sets or private data sets or whatever, and you could turn that into an incredibly persuasive story.

And look, I am 100% on board with AI. I think it is potentially the greatest tool that has certainly been invented in my lifetime. I’ve been waiting for it since I was in my 20s. I keep journals, handwritten journals, and I found one from when I was 22, and I didn’t call it AI, obviously, but this supercomputer, et cetera. But every technology is dual use in my opinion. And so I worry about the cognitive load that is coming for your average person. And I don’t know that we are adequately prepared for it, because as you said, the idea that logically you can go back and tie it into all of the footnoted, et cetera. By the way, I’m amused by most conspiracy theorists, because the real conspiracy is there really is no conspiracy except in filing.

Brian Chau
Yeah, it’s a conspiracy of incompetence. My least favorite phrase in the entire English language is “do not attribute to malice what can be attributed to incompetence.” Because if you’ve ever spent a moment in the real world, you would know that the most malicious people are also extremely incompetent. And very often incompetent people are also malicious. It’s not mutually exclusive. And yeah, I think you’re totally right. You’re totally right on this. You’re totally right on the human nature points.

Jim O’Shaughnessy
And so I think that there’s going to be a lot of potholes, there’s going to be a lot of things that were, whoops, we didn’t mean to do that. But rather than subscribe to the idea, no, shut it all down, make it illegal, et cetera, it’s like the example I always give is fire. Boy, fire was incredibly useful technology for we humans. I’ve read reports that when we started cooking our food, it’s what developed the prefrontal executive function of the prefrontal cortex. But fire is also really fucking dangerous. And so rather than try to ban fire, what we got was fire departments, fire alarms, fire extinguishers, fire exits, et cetera.

And I think that we’re going to have to think out really thoughtfully. We’re going to have to do this here as well, because I could definitely, I don’t know whether you saw the report that said that, I haven’t read the full report yet, so let me add that footnote, but that they were finding in multiple studies that large language models are actually more persuasive for a majority of people than human beings are. You do not have to be a very insightful person to think, oh, what would happen if I put that in the hands of my greatest enemy, right?

Brian Chau
Oh, but you should do a double click on those reports. I’ve read very many of those papers. It’s an area that’s fascinating to me, practically useful to me as well, as you can imagine. But do you know how the LLMs tend to be better persuaders than humans?

Jim O’Shaughnessy
No.

Brian Chau
You know, what are the causal mechanisms that they found? No, it is by being patient, not being condescending, ironically empathizing with the other person’s views. It’s basically by the same epistemic technologies that we’ve known since the time of the Greeks make for good persuasive rhetoric and good persuasive conversation.

Jim O’Shaughnessy
Yeah.

Brian Chau
And a lot of people just don’t want to put in the effort to do that. And that might be the frontier at the end of the day, is that the LLMs, no matter what your problems with them, are infinitely more patient, are by design infinitely more patient than humans are. And that’s going to come with, as you say, its own set of consequences, both positive and negative.

Jim O’Shaughnessy
And do you have any ideas about how that unfolds? And how...

Brian Chau
Oh, yeah. I’ve been thinking about this for so long.

Jim O’Shaughnessy
Enlighten me. Enlighten me.

Brian Chau
Yeah, I remember there were these two dueling camps back when I did AI policy in DC. I was one of the few people who were doing AI policy in favor of having more AI. This is a funny anecdote as well, but when we were deciding on the name, the org ended up being called Alliance for the Future. But when we were deciding on the name, we decided not to put AI in the name, because every single organization that had AI in the name was anti AI. This is an amazing thing. But that really gave me an insight into how policymakers were thinking about this.

And there tended to be two camps. There tended to be one camp which was something like, oh, AI is not a big deal. Maybe it’ll be good for GDP on net, but it will be fundamentally uninteresting, and therefore we shouldn’t regulate it. And that ended up being most of my allies in that situation. And then there was another camp that was something like, AI is going to fundamentally change the world, and therefore we must ban it.

And I don’t know if it’s because I’ve always been a pathologically optimistic person, but my way of thinking about it, that really solidified after leaving DC and building more with AI for myself, was something like, actually, the apocalypse was in the past. This is like reinventing postmillennialism, right? But actually that there has been this massive wave of antisocial and destructive behaviors, and actually most of that is going to be revealed.

There was this concept that was floating around for a long time of something like an encryption jubilee, a time in which we finally crack RSA, maybe that’s with quantum computers, maybe that’s somewhat with the assistance of AI, and we leak everyone’s encrypted messages, and then everyone can be okay with tolerating each other’s strange porn tastes and Google search history and whatever, right? And I think that there is something analogous with people’s either laziness or biased forms of argumentation, or even just, like we were talking about, the lack of effort that many political commentators have in really trying to persuade people.

And when the LLMs become widely diffuse, I think you’re going to see a wave of things that could be, that are on their surface incredibly appealing and invigorating, in a sense that just gets demolished on the thinnest pushback. A lot of those arguments are just going to vanish. Or are going to become these anti-markers of intelligence or of status. They’re going to be much better socially penalized, because any single person can go, you know, “@grok, is this true?” And there’s a certain class of arguments that will just completely be evaporated by Grok or by ChatGPT or Claude or any of these models. Probably even by these 7B models, these tiny models from Google or whoever, like Gemma, where even not even just existing technology, but technology that is well below the frontier of what we have now, can just demolish these arguments. And I think that the biggest societal change that we will undergo is unveiling all of this essentially clown behavior that has gone on for the past really centuries.

Jim O’Shaughnessy
Yeah. And I agree that I joke with people that we’ve always been living in The Truman Show, just now we are having the tools that say, oh, wait a minute, this all seems a lot more managed than we would have thought. And I think part of it came from this anomalous period, and I stress anomalous period, after World War II, through the ending of, I don’t know when the FCC changed the Fairness Doctrine, but we’re literally in America...

Brian Chau
It was under Reagan, right? It was...

Jim O’Shaughnessy
I think so.

Brian Chau
I think ‘82.

Jim O’Shaughnessy
Yeah, the 1980s. But I definitely think that...

Brian Chau
‘87.

Jim O’Shaughnessy
Thank you.

Brian Chau
It was second, second Reagan term.

Jim O’Shaughnessy
One of, I guess I would call it a bug, other people might call it a feature, of human OS is the desire for certainty and a hatred of uncertainty or chaos or what have you. And so we had this period between the end of the war and 1987 when in America there were three major networks that were the source of the news for the vast majority of Americans. There were two national newspapers, the New York Times and the Wall Street Journal. And that was it. And you think, like shooting fish in a barrel, if you want something buried and you have access to those three networks and/or those two newspapers, you can manage society in a much more seemingly orderly way. Now, that started to break down right when television went and started filming the shit we were doing in Vietnam. And that’s another example. And I’m wondering your take on this. Is what you’re doing in any way kind of analogous to what happened when we introduced reporters who, by the way, for much of Vietnam were not censored. They were not, they were just riding along, and the American public for the first time saw what was actually happening. And they’re like, holy shit, we don’t want any part of this. Could you see something similar happening with things like Effort News?

Brian Chau
Yeah, I think it’s totally revolutionary. And it was actually this unfulfilled promise of the Nixon era. The idea was “sunlight is the best disinfectant.” We’d finally have transparency and that would bring a whole new wave of accountability to governments. And funny enough, we got the transparency, at least much more than we had before. And that led to almost nothing. It led to the Bill Clinton sex scandal. And there was some degree that was useful in some degree, but it led to no real systematic change. And some people would argue, I think correctly, that there’s been since then a systematic decline in accountability in all sorts of government areas.

And I think in part that is because the infrastructure to take advantage of that transparency never really materialized. You had all of this dependency on sources reporting. And once again, this isn’t to fully condemn sources reporting, but especially if you’re censoring your own stories as an institution in order to get better sourcing, that itself would be something that is a lot more worthy of condemnation, where the transparency was there. But at that point the news organizations, the centralized news organizations, I think actually by that time both TV and print, were so attached to getting stories through source reporting that they’re no longer able to effectively comment and really effectively counterbalance the measures that were taken in place to control information. And that only became stronger in the COVID and the post social media platform era as well.

And I think that is changing for a number of reasons. Number one is just underlying technology, right? It’s a lot easier to make these queries. It’s a lot easier to just process a sheer amount of documents, many of whom will be hits, right? Or sorry, many of whom will be misses. There will be a much greater number of misses per hit, right? Where for example, if we’re just looking through every grant in the HHS database, a lot of those grants would just be fully legal, and not just fully legal, but fully non controversial stuff that we, at least on balance, I don’t know if it’s fully good as a policy goal, but on balance, do not see as contradicting the purposes of HHS.

And that cost benefit calculus has totally changed, where if it’s something like, oh, maybe we’ll get one scoop, but we’ll really have to burn through thousands of hours and hundreds of thousands of documents of things that we’ll completely not get anywhere with. Before it would just have been, you know, are you kidding me? Let’s move on to the next area. But now that can actually be investigated and actually investigated fairly diligently. So I think the overall trend, like I said, my underlying theme to all of this is that yeah, there are going to be problems, there are going to be misuses of the technology, but the overall trend is towards something better than what we had before.

Jim O’Shaughnessy
Yeah. And that brings me to the economic question I had for you. So if in the past there was a big story that a news organization wanted to own, so to speak, like the Boston newspaper that basically broke all the stories about the child abuse rampant in the Catholic Church, and they made a movie about it, et cetera, that you can quantify. You could say, okay, we need to hire six, a dozen, however many journalists, it’s going to take them six months, a year, okay, we can tote up exactly what their salaries are, what their overtime is, what the cost of travel, et cetera. But you have costs too, right? In other words, you have costs of inference, engineers, a variety of things. How cost advantaged are you over the model I’ve just described?

Brian Chau
The stories that we’ve broken so far, whether it’s the Preferred Communities grant, whether it’s the degrowth donors, all of them are stories that would have just been straightforwardly infeasible under the previous model, which would have, if you were to put a dollar number on it, and it would probably not even be feasible to just recruit that many journalists. It would be this kind of market that eats the entire old market. It would have been like upwards of tens of millions of dollars at least, if you could even physically assemble, like find that many journalists who had those competencies in those areas, to pay. So it is a total sea change in terms of what is capable and what is cost.

Speaking of cost, though, this is actually more of my traditional educational background. I had a degree in pure math and started in machine learning at a really young age, basically when I was still in high school. Anyways, I had been a machine learning engineer before, and this is mostly what we optimize on, because a lot of the harnesses make extremely inefficient queries to databases. It’s shocking, because at the same time I can look at some of the cyber security applications, I can tell that there are a lot of things that the LLMs are a lot better than me on. But in terms of making API requests, not all of them, but many of them, or making efficient database queries, they just will put out tons of fucking slop queries and will consume way more tokens, will just take longer, will have higher latency on these tool calls. And there is just a lot that you could optimize for in many dimensions.

That’s part of what’s so exciting about this. And that’s been super exciting for me. It kind of points to that environment that a lot of people talk about, this is actually before my generation, but of the early Internet, where it seemed like everything was so unoptimized. You could just sit down and think about it and you could optimize these things. You as basically anyone who was reasonably smart, who had a computer, was reasonably familiar with these things. And that’s just this massively inspiring thing. And that’s something I feel like we’re picking up a ton of momentum on every single day on our team.

Jim O’Shaughnessy
So what about the idea that journalism has been misclassified for a century? And by that I mean, I think of H.L. Mencken, right? He was the king of the muckrakers, and he was always great with his quotes and everything else. But I, so at least I, maybe others don’t, but I sort of associate journalists with writers, with the actual act of writing or producing, if it’s TV or radio. But maybe they were actually search and verification engines, and using writers was just a hell of a lot cheaper because we didn’t have the technology. Your model changes the economics of finding needles in haystacks, right?

Brian Chau
Yes, that was one thing that we thought of putting on the website. We find needles in haystacks.

Jim O’Shaughnessy
But my question and pushback on that is, if I was your opposition, right, if I was trying to get up to something nefarious, why wouldn’t I, if I have my own tools that are at least as good as, if not better than yours, why wouldn’t I just make a fuck ton more hay and make it much more difficult to find the true needle, so to speak?

Brian Chau
Oh, it’s already happening. Yeah, I think that’s totally fair, and that’s totally happening. And actually that’s been happening for 30 years. That is the intelligence agency, Defense Department, that is the documented strategy of just producing so many documents, of maliciously complying with FOIA requests. That’s totally happened, and I think there will be another escalation of this. Imagine you make a FOIA request to the CIA and they just give you petabytes of AI slop. That could totally happen, and I think that probably will happen. So I don’t really have a solution to that necessarily. To some extent we will have to AI harder, and it is this Red Queen’s game where you’re staying in the same place, but you’re running faster and faster.

I think in some sense we can outcompete the CIA, at least in this narrow area, or we can outcompete all of the people who would otherwise be trying to obfuscate information. And in part that’s just the pace of technological development. Of course, I think a lot about incentivizing our organization and building up our capacities in that way. In part that’s innovator’s dilemma. There are all these tech theories and why the incumbents will always win, or why the startups will always beat the incumbents. It’s always treated as this kind of predetermined natural course of history thing. I think we just have to win. I think we just have to fight as hard as we can. And I think you’re absolutely right that it’s not just going to be us, it’s going to be people on both sides. It’s going to be people both maliciously complying, maliciously producing information, subverting transparency laws, or at least kind of maliciously complying with transparency laws. That’s totally going to be happening. And at the same time we’ll just have to race on faster and faster.

Jim O’Shaughnessy
Yeah, but again I come back to good old human OS, and I don’t know anyone who reads the terms and conditions before clicking okay. And I agree with you, by the way, that the patient large language models will read all of them and they will point out all of the ones that go against you. But I’m worried about the people, you know, they’re busy with other things in their life, right? They’ve got a family, they’ve got a job, they’ve got hobbies, et cetera. And meanwhile I kind of see this massive battle between two philosophical points of view, if we keep the extremes, right, and the weapons are getting a lot more precise.

And I just wonder, and it’s like, again, the Pandora’s box is opened, and so trying to say no, we want to rethink, that’s not going to happen. But I do wonder if we should spend a little bit more time on cog sec, cognitive security, right? Like maybe freely disseminated. If we could figure out a way to really be able to judge deepfakes, for example, wouldn’t it be cool if you just freely distribute it to everyone, something on their phone that was like, the minute a video showed up, it just went “deepfake” across it. At least that would condition them to start thinking. Oh, you’re absolutely right about history. People have been manipulated by religions, by political ideologies, by a variety of incentives for all of human history. That’s nothing new. But now we’re doing it at weapons-grade and it scales. And so I definitely think some form of cognitive security for everyone might be a good idea.

Brian Chau
Yeah, you’re definitely the best kind of critic, Jim, because I think I really share the same fundamental view of human nature. I have a very Hobbesian view of human nature. Hobbes is still my favorite philosopher to this day.

Jim O’Shaughnessy
Brutish and short, right?

Brian Chau
Yeah, and so much more than that. Both the dual powers of the sovereign, the origins of human reason, goes so far. But I think you’re right in that I think that you want to draw a distinction between the scale of deployment, where you’re absolutely right, it’s bigger than ever before, and the equilibrium harms. I think something that every major tech policy fight has sort of gotten wrong in the past few decades has been this conflation of the possible harms and then the equilibrium, where people will say this, for example, with cyber, that’s something that’s more played out. People will say, oh, there are so many potential hacks. And then you ask the straightforward next question, which is, well, how many of those potential hacks will be prevented by AI? And not only that, how many of the potential hacks from past generations, or just possible with previous levels of software or previous levels of human hackers, will be prevented by AI? And then that equilibrium, that’s not zero, right? That’s not zero harm, but it’s very different. And man, this could really be a long answer. I will try to keep it from being like a 30 minute Hobbes monologue.

Jim O’Shaughnessy
Yeah, yeah, no, obviously, let’s try to make it a little more compressed. But I think this is important. I think that people who are in favor of AI and all of the tools and the powers that they unlock need to examine and acknowledge the other side of the argument. Don’t get me wrong, I’m maybe one of the most pro AI guys out there in terms of the potential for what it can do. We just made a movie about how the Vesuvius, the volcano that destroyed Pompeii...

Brian Chau
Is this the scrolls?

Jim O’Shaughnessy
Yeah, yeah. And love the scrolls. We made a movie about it because to me it’s the coolest thing in the world. It required a particle accelerator and AI to be able to translate these scrolls, but now we’re able to transcribe ancient Greek and Roman scrolls that if you touched them in the past, they just disintegrated. And I’m giddy about the use cases for AI in terms of expanding our knowledge, expanding innovation, expanding discovery, et cetera.

But I definitely think that you need to be, I call myself a pragmatic optimist. And by that I mean I think you need to consider the unintended consequences and try to come up with good solutions for them. Because if you don’t, the people who are on the other side of the argument are going to make hay with those, and they’re going to say, yeah, but, right, like. And most of the objections are going to be way deep in the tail and very unlikely to happen. But if we who are in favor of this new expansive rocket ship for the mind that AI is. And also I hate the artificial intelligence. Brian Roemmele calls it intelligence amplification, which I much prefer, because really that’s, in my opinion, one of the things it’s doing and/or uncovering, right, like you’re doing. But I do think we need to think about these other use cases and have good ideas, because it’s going to happen.

Brian Chau
Oh, absolutely. It’s totally going to happen. And I think one of the most important questions for any philosopher to ask is to step back and ask, is this a matter that will be decided by philosophy, or is this a matter that will be decided by action? And to a large extent, I think that the part that has been decided by philosophy we’ve already talked about, it’s kind of the nature of the story and that kind of epistemic field of what comes. And the part that will be decided by action is essentially, what are the names in the media ecosystem people will trust, what are the solid ground, right? And that can never be fully reliable. You shouldn’t put your absolute faith in any kind of news reporting or any kind of human institution in general.

But you have to have something, and I think about a lot of that on a daily basis as well, where Effort is not merely trying to produce a good technological platform, right? You’re not merely trying to say, like, oh, here is this technology, everyone will have this technology, voila. I’m really concerned, and I think this is very different than a past generation of more optimistic, more maybe Rousseauian founders, even. I don’t know if they’re explicitly Rousseauian, but implicitly Rousseauian. But I’m a lot more concerned about institution building, that this is the specific group of people who will be employees and founders and contributors to Effort. This is a specific kind of culture that I want to calibrate on epistemic openness and of hypothesis testing and of the scientific method and just a very high standard for everything.

Not publishing slop. That’s the most important thing. We do not publish slop, and we do not publish slop in all sorts of ways. We do not publish slop in that we do not publish AI writing, at least at this point, writing still, at least in our experience, not great. We rigorously, we human write all of the articles and thoroughly check for any improvements we can make to the phrasing, any improvements we could make to the clarity. We also, of course, don’t publish slop in terms of records. We verify all of the records, both with a lot of AI tools and by hand. We don’t publish slop in the sense that we don’t bury stories, but we want to make sure we take our stories to completion. We don’t want to just be wildly flinging accusations. We want to get to the point where we have a clear border of, this is what we found, this is what we didn’t find, here is how we can prove what we found, here is the steps that led to us not finding these other things.

And I think that at the end of the day, part of that will be decided by technology. Of course, we would not be able to do most of what we’re doing now without it. But there’s also a large part that will inevitably come down to a form of human judgment. And that is something, in my opinion, that you have to be proactive about. You can’t just completely leave the human judgment to the wind. That you have to be proactive about as we’re building out Effort. And to me in the long term there is no perfectly philosophically consistent defense against all bad actors. That’s just not feasible. Maybe there’s a solution to it. Maybe GPT 7 will come up with one. But it is just beyond me and it’s beyond every philosopher in history. But the practical solution to that looks more like the institution building that I think a lot of people in the previous generation have neglected.

Jim O’Shaughnessy
Yeah, and that’s an interesting point, because it also leads to objectivity. I think that’s a term that we like to use a lot and misuse mostly, because I think that your organization, for example, right, like I would love to see that you don’t get captured because you’re a subscription model, right? There’s always audience capture. And are you dedicated to exposing whatever kind of corruption and/or story that got buried regardless of which political side it helps?

Brian Chau
Yeah, for sure. And I think that at the very beginning you’re going to see actually a different kind of selection bias, which is that we’re reporting on essentially stories that have been dropped. Because for example, the refugee resettlement story, that’s something that could have been reported on for literally five years. So the fact that we are able to report it is a direct consequence of it not having been reported. And honestly, it’s funny because this is going to be a justification for stories that are perceived as more right coded. But honestly it’s because a lot of the right wing media ecosystem are just a bunch of muppets who do not seriously complete their investigations and are comfortable with just publishing slop, publishing accusations, not actually digging into the documents.

And I mean, digging into the documents may not be completely easy, especially without AI. But it is just this completely different equilibrium where, you know, there are obviously biases with the New York Times, but they do actually do investigative reporting at least, and they do actually break stories, and they break stories in a certain direction, and that’s going to leave actually a gap that is not going to be equal. So I think that in the short to medium term you should expect that to be unequal via negativa.

Let me give a more concrete example related to that, though. We’re going to be breaking a story, I don’t know exactly when this will come out, but we will be breaking a story within a few days, reporting on something that the Trump administration has been trying to keep secret, which is the whole Freedom Fuel network. Do you know about this? You know about Freedom Fuel?

Jim O’Shaughnessy
No, I don’t.

Brian Chau
It’s this fascinating mystery. I think it’s been this fascination of journalism world because it’s this particularly enticing thing. Essentially the Trump administration has been promoting this series of gas stations in New Jersey and Pennsylvania that have been selling gas almost certainly at a loss. They originally sold at $3.47, right? This is because Trump is the 47th president. And they’ve in general been somewhere like 40 to 50% below the going gas rates in those areas, almost certainly losing money compared to selling that gas even on the open market. So a classic case of fascinating mystery.

Jim O’Shaughnessy
Yeah, and economists would call that dumping to gain market.

Brian Chau
Yeah, yeah. And so there’s this fascinating mystery of where’s the gas coming from. And all the king’s horses and all the king’s men have tried to figure out where the gas is coming from and they have not figured it out. And we have not, I think we have meaningfully moved forward the Freedom Fuel case, I’ll put it that way. Meaning we’ve not fully found evidence of government subsidy, but we have found fairly conclusive evidence of self-dealing.

Jim O’Shaughnessy
Interesting. Of the stories that you’ve dropped so far, which one got the most reaction, both positive or negative? And then I do want you to, because when I was getting ready to chat with you, I read your story about how to hijack the new X, or as us old timers call it, Twitter, algorithm.

Brian Chau
But wait, am I an old timer?

Jim O’Shaughnessy
Maybe in spirit, maybe learning a lot today. But which stories are the ones that really the lightning hit the rod?

Brian Chau
Yeah, it was definitely the refugee resettlement story, because this one was just something where the financial record was so damning, and also where the players involved were these already very big media entities. US Conference of Catholic Bishops, Church World Service, HIAS, Episcopal Migration Ministries. For a long time they’ve been trotted out. They are the most public of public figures or public entities. They’ve been trotted out to be very critical of any kind of migration restrictions.

And for literally, for upwards of five years in terms of the grants that I reported on, but upwards of 10 years at least for the total body of grants, it had just gone completely unnoticed that they were being majority, that the vast majority of their revenue, 81.8% in the case of USCCB, 89% in the case of Church World Service, was being funded by these resettlement grants. In other words, they were explicitly benefiting from the policies they were advocating for.

It would be like taking a dairy farmer and having them be the object, treating them as the objective moral arbiter of whether the government should subsidize milk. It’s like, there are these well known names who go on TV every time there’s a milk policy debate. And they’re treated as the representatives of Christian Americans worldwide, or Christian Americans across the country. And they come out and they say, “we morally condemn in the strongest terms the President’s opposition to subsidizing milk.” And then it turns out five years later that all this time they’re selling milk. It’s like, what? This is a totally crazy story. And it also goes to show, despite all of the media attention, despite all of the endless commentary on these organizations, for a long time no one went and actually dug into the financials. And now we did, we finally done it.

And yeah, the reaction to that was overwhelming. Interestingly, there’s a certain type of story, there’s a certain type of, I mean, I don’t want to be mean to any individual specifically, but as an institution, there is a certain type of New York Post story that very effectively draws kind of counter criticism, that breaks a real thing, but also taints it in a way and fills it with other sort of inaccuracies or bias, or basically gives this massive attack surface to critics of that story. And of course the most famous one of these was the Hunter Biden laptop, which at its core was a truthful story, it was a real finding, but was distorted in all of these ways, which eventually became used in order to weaponize social media against it.

Anyways, we got very little of that with the refugee resettlement story. I think actually for that reason. And there’s actually a perverse incentive there, I’m going to do my best to avoid it. I think that we shouldn’t be lowering the quality of our story intentionally in order to get more counter reaction from the other side. But I think there’s a certain type of story that gets a ton of negative counter reaction because it, I don’t know if it intentionally introduces flaws, but because of the flaws that are there. And I think that this was sort of the opposite kind of story, where the financials were so clearly laid out, the conflict of interest was so undeniably established, that the other side didn’t even want to touch the story.

Jim O’Shaughnessy
Interesting. And we’re talking a lot about incentives, right? And another point of view that is kind of consistent with my quip about we’re all living in The Truman Show and always have been, is like, what percentage of, in quotes, news is just propaganda, and it’s literally the various sides vying for power trying to win the news cycle? Like that’s another one, winning the news cycle. That’s as old as we have the media, right?

And I just wonder, one of the things that I do worry about is all of this is so new. And I’m not just talking about AI, I’m talking about, Bill Bryson has a great book called America One Summer, in which he’s talking about the first time a single human spoke to more than a thousand humans, right, was the guy on the radio announcing Lindbergh’s return from flying across the Atlantic. And so telegraphs, like, it’s in the scheme of human history, all of these new technologies are brand spanking new. And now we’ve got, we’ve gone from spears to thermonuclear multiple warheads really quickly. Is there going to be some form of way that humans just...

Brian Chau
Yes, I think it’s all resolving now. I think it’s all not resolving to a final conclusion, but a lot of that built up technical debt is now being reevaluated, and that’s the conflict we see. That’s what people are angry on social media 24/7. And not all of that is directed in a productive way. A lot of that is directed towards slop. Those criticisms are totally fair, but largely what I see is a reevaluation of those fundamentals. As Nietzsche called it, “a reevaluation of all values.”

And I think where that starts is something I call the crisis of nominalism. There’s this big phrase that goes around. You’ve caught me at a great time, because I was just on a four-hour hike and I was thinking about this and I have all these thoughts fresh in my mind. But there’s what’s called a crisis of liberalism, which I think is really mislabeled. And the theory behind calling it a crisis of liberalism is like, oh, there’s a ton of premises, but the story is like, oh, we’ve lived in what we now call liberalism for roughly 250 years, basically since the American founding. And that is now coming to various flaws, whether that’s fertility, whether that’s social media, whether that’s foreign influence, whether that’s migration. And what people will say is that liberalism is collapsing under its own values.

And I think a point by point deconstruction of that claim, almost every premise is false. Where we are not living under, we are no longer living under liberalism. It’s not a continuation of older values. Liberalism is not causing the issues that we see. And actually it is not even a crisis. It is a reevaluation of a slave decline.

And I can get into each of those points specifically, but let me try to give a core, something that’s like a useful takeaway from this. Is that nominalism, what it actually is, is people taking a name for granted, right? This is science. It was published in a title, in a journal called Science, therefore it must be science, right? And not actually going looking underneath. Is this the scientific method? Are these neutrally tested hypotheses? Were these in a controlled environment? What was the statistical probabilities, that this was actually a relevant finding, and so on and so forth. That at the very surface level, you kind of look at the cover of the box and you never actually look inside the box.

That problem has persisted. It has persisted, certainly scientifically, it’s persisted in news media, in both the older institutions and the kind of influencer slop type media that’s come up to rival it. Both of those domains are domains where you kind of just get the slop and you never look inside the box.

And this is really the most disastrous version in spending. And you get this in a lot of government spending. I’m very sympathetic with the DOGE people, where they had a complete communication failure and they just got so internally overwhelmed that they ended up being driven crazy and not really being productive in their political actions. Where if you are someone who’s had experience putting together financials for a startup, I’ve done this both in my own company and with previous companies that I’ve worked for, I’ve done this personally, and you are used to that level of accounting, and you know that if you do not present this quality of information to auditors, you will go to jail. And you see the standard that is set in Treasury or in these other government departments, then you will have a meltdown. It is just a completely different standard. It’s a total double standard.

And they were expecting to go to the media or to go to Congress with this, and for them to react with, oh my goodness, this is a total, this is like a five-alarm fire. This is something that, if you were done at a private company, you would go to jail for. This is some crazy stuff. And they were completely not prepared for the reaction that they got, which is, this is how things have always been. And both of these sides are kind of acting rationally in their own narrow context. It is simultaneously true that if you were doing this in a private company or public company, if you’re doing this in any kind of normal corporation, you would go to jail for this. That’s both simultaneously true. And the kind of protests of the senators of, this is how it’s always been, this is maybe not good, but there’s not much we can do about it, this individually, I think that’s also true. So it was this huge kind of Shakespearean tragedy that played out.

But that’s a good illustration of what I mean by the crisis of nominalism, that we have these names, right? We have these names of accountability or auditing or financial record keeping. And under the surface they’ve completely diverged. Under the surface you actually look inside the box and it’s like, what is even going on? It is this chthonic mass. And a lot of that is going to be reevaluated. A lot of that is going to be either split into different names, or there is going to be this type of philosophical colonialism where people who have been more competent over the past 10 or 20 or 30 years will go in and have to clean up these institutions. Part of that is also this new trend of software roll-ups, which could be a completely different rabbit hole. But there’s a lot that’s going to shift, and that’s going to hinge both economically, politically and philosophically on this crisis of nominalism, of the big question of what happens when you finally look inside the box.

Jim O’Shaughnessy
Well, you make, now we’re down to linguistics in my opinion. So for example, I think it was Kierkegaard said, “when you label me, you negate me.” And you were using words like accountability, et cetera. Of course, good old George Orwell understood that a long time ago when he talked about Newspeak and, you know, “war is peace, freedom is slavery,” et cetera. And then, of course, the classic Bill Clinton under questioning during the Monica...

Brian Chau
“What do you mean is?”

Jim O’Shaughnessy
Yeah, it depends on what you mean by the definition of is, is right? But yourself, you’ve said slop I don’t know how many times. You see, we’ve always had slop. We, except it was always just human slop, right? Of the millions...

Brian Chau
When I say slop, I am inclusive. I am not discriminating based on species.

Jim O’Shaughnessy
I understand, but I want to say we get captured. One of the dangers of labels, in my opinion, is it puts thinking aside, right? You label something slop, it goes into that bucket. We call it slop. You no longer really try to disambiguate, is this really slop or is this real? I mean, would Joyce’s early works get put in a slop bucket? Probably. You know, Finnegans Wake and Ulysses. And it was because he was so new, right? His style of writing was so new, people literally didn’t know how to read it, right? And now we know how to read it now, because we evolved into understanding that kind of postmodern way that Joyce approached his novels.

But I just think that I worry too, because labels, the power of labels. You yourself have just made an excellent case, right? Accountability, transparency. When I hear transparency and accountability, I think, okay, wow, it’s going to be accountable, this is going to be transparent. And so the power of language in and of itself, the semantic meaning, the semiotic meaning, is something that we’re going to also have to kind of dig into.

One of the ideas I had would be, how cool would it be to have an AI companion that was, I’m calling it the Reader, right? And when you’re reading a news article, it just points out, like, factually incorrect, appeal to emotion. I don’t know if you’ve read Influence by Cialdini. We talked about it a little earlier. And I joked one of the reasons why the large language models were pretty good at it was because they’ve been trained on the entire corpus of influence. And Cialdini is kind of the king with his book Influence.

But I definitely think if you had a Reader there that was saying, like, who benefits from this? I used to say to younger people, and they’re asking me, like, how do you navigate reading the news, this pre AI, I was just like, ask yourself the question, who benefits if I believe this? What are the objectives of this particular writer? Are they for a particular outcome? Are they just informative? What are they? But if you actually had a reading companion right next to you, or a watching companion, right, I mean, if we had this, I’d put it on this podcast and it would probably contradict me a lot. Well, Jim is doing an appeal to emotion. Jim is doing an appeal to authority, all of those things. But I definitely think that organizations like yours, that’s why I was so excited to talk to you. You’re the beginning stages of this unfolding.

Brian Chau
Yeah, I was just, so when you talked about Joyce and his early works, I immediately flashed back to this experience I had two months ago. So I’m going to read something and tell me what you hear.

Jim O’Shaughnessy
Okay?

Brian Chau
“The old professor, em dash, Calguès by name, em dash, aimed his glass at one of the ships still lit by the sun, then patiently focused the lens until the image was as sharp as he could make it. Like a scientist over his microscope peering in to find his culture swarming with the microbes he knew all the time must be there. The ship was a steamer, a good 60 years old. Her five stacks straight up like pipes showed how old she was. Four of them were lopped off at different levels by time, by rust, by lack of care, by chance, em dash, in short, by gradual decay. She had run around just off the, she had run aground just off the beach and lay there, comma, listing at 10 degrees like all the ships in the phantom fleet. There wasn’t a light to be seen on her once it was dark, not even a glimmer. Everything must have gone dead, em dash, boilers, generators, everything, all at once, em dash, as she ran to meet her self-imposed disaster.”

This is from the second page, I believe, of Camp of the Saints. And I was going to read this, I was going to reread this, and I just couldn’t do. Was too AI coded for me. It just broke my brain. I know it’s obviously not AI, but it’s just like totally broken, broke my brain.

Jim O’Shaughnessy
It’s so funny, serendipitous. I was just rereading, or trying to reread that book. For people who are not familiar with In the Camp of the Saints, it was a book written, I think, in 1970s, right?

Brian Chau
Yeah, a long time ago.

Jim O’Shaughnessy
And it envisions the very migration problems that we are having now, done differently, if my memory serves. I read it back then and was horrified. And I tried to, I picked it up again and, like you, I’m like, wow. But I had a different reaction than you. My reaction was, why do large language models? And if you look at my Twitter account, you’ll see that I have used em dashes copiously my entire, I’ve written four nonfiction books, obviously all before AI. You’re going to find a lot of em dashes in them because I love them. And so on Twitter I say, you can come and pull my em dash out of my cold dead hands.

But isn’t it fascinating, right? It’s like, the same with the, it’s not X, it’s Y. Go back and read mystery novels and things. The reason they use that technique and the reason they use em dashes is because of the training literature they were trained on. We use em dashes all the time previously. And you have the Orient Express. Like it’s all, he wasn’t this, he was this. You know, when she’s describing the villain. And so it’s another part of that axiomatic reaction, right?

Brian Chau
I think I want to add a little nuance to that, because I think that these are actually different cases. I think for em dashes, you’re mostly right on. That is just part of the training data. For the, it’s not this, it’s that, that’s more downstream, I think, of a particular technique called, oh my goodness, just struggling to pronounce this correctly, called contrastive learning. There we go. Called contrastive learning, where the idea was that the models would have a better directional update if they were given both positive and negative examples of something. And this was a specific technique published in papers by OpenAI, by Google, all of the biggest names, that specifically use this format, and was actually effective, at least in the short term, for post training their models. So I think that those two cases actually have slightly different origins. But I think the underlying idea, if you, you shouldn’t necessarily dismiss these literary patterns, that they’re legitimate literary patterns. I think the underlying idea is right.

Jim O’Shaughnessy
Yeah. I think if you are an Agatha Christie fan, that is who I was referring to when I talked about Murder on the Orient Express. She does that. It’s not this, it’s this, all throughout her books, right? And because she wants to surprise the reader, right? You thought that he was a good guy. No, he’s actually the villain. You thought he was steadfast. You thought he was noble. No, he was the villain.

And so I just think that there’s a lot of ignorance about the idea that the models do what they do ultimately, right? Agrippa’s trilemma. You familiar with Agrippa’s trilemma?

Brian Chau
No, I’m not.

Jim O’Shaughnessy
Well, that would take us forever. But the short version of, he destroys logical systems because he ultimately, and Lewis Carroll, a mathematician and logician, actually wrote a book called, not a book, he wrote a piece called What the Tortoise Said to Achilles, and it made the case even better than Agrippa’s trilemma. But basically it’s like every time you have a logical rule, you gotta say, well, why do we have that rule? And then you keep going down, down, down. And you finally get to that base rule where you said earlier in our chat, I just made it the fuck up. But in Carroll’s What the Tortoise Said to Achilles, is ultimately everything is a human choice or a decision, at least now, right? This may change, right, going forward. You mentioned ChatGPT 7 or 10 or 12 or whatever. But for now, and historically, Agrippa’s trilemma is the problem of the infinite regress of. There’s a, let’s, it would take us an entire different podcast to talk about Agrippa’s trilemma, but I think you would definitely be interested in it.

Brian Chau
Yeah, I’m reading it now. Yeah, it is this, it reminds me a ton of formalized set theory. This would be okay. Like it would not be entirely surprising to me, but it would be like a life changing moment, I think, if the LLMs discovered a reduction in the set theory axioms. That would be a moment that I’m here for. It would be like my personal 9/11 is when AI discovers a way to reduce the set theory axioms.

Jim O’Shaughnessy
Yeah, well, I mean, again, because I am very optimistic about the, even knowing that we’re going to have a lot of bad with the good, I definitely think that the power and discovery that AI allows us to use as tools. That’s the other thing that drives me a little crazy, right? Like, I was looking up the thing on our system which we’ve trained on a bunch of different things. And you had said like 80 to 100% of news is sourced, going to the newspaper. Which, well, it gave me the whole history and it was like, yeah, media scholar Jim Macnamara reviewed 150 to 200 studies and he found that up to 80% of media content is sourced from or significantly influenced by PR, with estimates of 50 to 75% common. But then it keeps going. It goes back to Herbert Gans’s classic 1979 content analysis, and it gives me all of the notes that I can actually go and go to the actual book or study and find. And I definitely think that for a certain type of person, the inveterate rabbit hole diver, that is really cool.

My question is, is it cool for non nerds? Like, I’m totally willing to call myself a nerd, right? And I love rabbit holes and I love doing all that. And I would guess that you would be coded nerd.

Brian Chau
Yeah, sure, yeah.

Jim O’Shaughnessy
But I just wonder how much of a difference it’s going to make to the non nerds. In other words, I think of the flat Earthers. If you could do a news story based on all of the data and convince the flat Earthers, right, that would be of interest to me. There, again, we come back to kind of the scientific method, right? If it’s not falsifiable, it’s a religion, in my opinion, right? It’s a belief system.

And what I’ve seen, historically at least, and I don’t mean to pick just on the flat Earthers, there are a lot of cult like beliefs that are patently untrue, but when confronted with data, and I made my career in asset management on doing algorithmic investing using data, so I’m a big believer. But one of the things you see is, here is Mr. Flat Earther, the million reports showing you why you’re wrong. And what happens is, in many cases they double down on the belief and they’re like, yeah, no, that, even though you can show every footnote, every study, everything, now that’s all wrong. Aggressive, I don’t know, I don’t want to say stupidity, but aggressive disbelief. Do you think you ever change those minds?

Brian Chau
I think on operational grounds, on anything where it’s like, oh, you actually have something at stake, you can change those minds. I think when it’s this kind of like, when it’s this Truman show thing and it’s pretty clear that, you know, if you think the earth is flat and the entire system of physics that’s been developed around a circular earth is wrong, like, do you avoid flights? Like a lot of the time the answer is no. And the ones who the answer is yes, actually I would probably respect more, because of course that entire system is based off of an assumption of a flat Earth. Not an unfounded assumption, of course, but that all comes along with the system in play. And so you have this really fake virtualized game of debating about the flat Earth.

And I think in that environment you’re never really going to get anywhere with most of the time. And maybe the AIs will have enough patience to do that and eventually win someone over. But on all practical grounds, that is actually not a particularly effective use of our time, right? Like the flat Earther is not actually particularly harmful to anyone, and in a lot of cases can go about their own life without that cognitive dissonance, right? They’ll go on the flights, they’ll talk to their round Earth colleagues, they’ll in a lot of cases actually work a stable job and so on. And that’s basically fine.

And actually I think there will need to be a slow political reorienting around kind of what Leo Strauss calls the cave below Plato’s cave, right? That we have all this scientism. We’ve now gone to the extent of applying the scientific method to all sorts of ideas and concepts and philosophies and all kinds of new moral rights that are not the ground of the scientific process, are not falsifiable, are not things that you can decide via microscope, and are slowly being unrolled and seen as such.

And I think that political process involves actually, it’s interesting, this is kind of a, I think it’s a tension, but not necessarily a contradiction. We can have the philosophical maturity to realize that there are forces acting on the world that act in opposite directions at once, or that the different forces will act in different directions even if they’re acting at the same time. But I think there’s both a tendency towards developing greater standards for truth, as well as actually an admitting that there are these issues that have been treated as truth or as treated as scientific that are really not scientific at all and are rather more moral or theological issues.

And I think, to add one more thing on this, I think that there’s a big unraveling that goes back to Mill, who I think was actually a traitor to classical liberalism by redefining the goal of classical liberalism around consensus. This was the classical Mill’s trident, right, which was an argument for free speech that I think ultimately undermines free speech when it comes to the modern day. And the idea was, okay, if you think that what someone is saying is wrong, then they should be allowed to say it, because then the free speech, the debate will prove them wrong. You’ll have good information to beat the bad information. And if you think it’s correct, then obviously they should be allowed to say it, because they should be allowed to tell the truth. And then if you think that it’s somewhere in between, or if it’s uncertain, then it’s either case one or case two. So you should still let them have free speech.

And to be clear, I’m for free speech. I’m not anti free speech. But what this did was it redefined the old classical liberal rights established by Locke, and I think established before we even had the term classical liberalism by Hobbes, which was much more around survival and around peace. That the idea was that you would have classical liberalism, you would have freedom of speech, freedom of conscience, the acknowledgement of reason, and you would have that under the grounds of avoiding war. That there were these intractable beliefs that people would have, particularly around religion, that if not dealt with in a mutually tolerant way, would inevitably lead to war. And this was not a hypothetical, of course. This was the Hundred Years War. There’s many religious wars before that. And the idea was that you would have these natural rights that were enshrined in a mutual understanding, that if we did not have these rights, it would be a violent free for all.

And that slowly got displaced with this idea of consensus, that if we have these rights, then not only is it possible, but it is inevitable that we will reach a total consensus. And that broke down in all sorts of ways. Most notably that people realized that wasn’t what was happening. That as social media gave more people not just the right, but the potential to speak, that there was less consensus. And, you know, as we talked about at the beginning, some of those people were just making shit up. But it actually undermined this new theory of classical liberalism, which I think was not a theory of classical liberalism at all. It turned into a theory that was deeply antithetical to classical liberalism.

Jim O’Shaughnessy
You know, Brian, we could make this how long? I’m not a listener usually, but how long does, like... Chris Williamson. Well, I do listen to Chris.

Brian Chau
This could be the eight-hour Lex podcast.

Jim O’Shaughnessy
Yeah, this could be the eight hour. But I am getting my hook for my producer. So what I will do is, we’ve left so much left to be discussed. We’ll arrange for you to come back on. But for now, first off, tell everyone where they can find Effort News and how they can subscribe.

Brian Chau
Yep, effort.news is where you find us. effort.news, slash subscribe. And to find some of the news stories that I’ll publish on socials, you can just find brianchau57 on all of the socials, like X, Instagram, so on. That’s B, R, I, A, N, C, H, A, U, 57.

Jim O’Shaughnessy
Perfect. And next time around we’ll have to talk about all these other fascinating things, because I think we are in a very tumultuous and yet fascinating and innovative time. And I think the more we talk about these things and discuss them, the better people can understand them and reframe them.

You know, we didn’t even get into the difference between the real scientific method and scientism, but I guess the shorthand there could be, if anyone tells you the science is settled, they’re an idiot, because science is never settled, right? It just keeps like, yeah, this works, this works. Oh right. Newtonian physics worked and worked until we, the quantum guys came along and said, actually. So it’s an ongoing process, right? And it should be falsifiable, it should lead to better explanations, it should lead to more explanatory power. But it’s a process, right? It’s not anything that is settled, right? I often think of the true scientific method as being like pure punk rock energy. It’s like, no, I’m not going to take your word for it. No, I’m going to actually...

Brian Chau
Exactly, exactly.

Jim O’Shaughnessy
If you’ve seen or listened to the show, Brian, you know that we do have a final question for you. And that is, we’re going to make you the emperor of the world. You can’t kill anyone, you can’t put anyone in a re-education camp. But what you can do is, we’re going to hand you a magic microphone and you can say two things into it that are going to incept the entire population of the world. Whenever their next morning is, they’re going to wake up and they’re going to say, you know what, I just had two of the greatest ideas, and unlike all the other times, I’m actually going to act on these two ideas. What are you going to incept in the world’s population?

Brian Chau
First has to be the crisis of nominalism. I think that’s right. You have to ask the question of what’s in the box. And not everyone will come to good answers. Some people will ask that question and they’ll answer it by making stuff up. But I think even asking that question, a lot of things cannot survive contact with that question. And almost all of them that cannot survive contact with that question of, is this nominalism, should not survive contact with that question.

Second thing is, I think, maybe this was primed by listening to your podcast with Jonathan Bi, but I think that’s like a question for everyone, and then a question for people who are already doing things about it or who have set out to do things about it, is more like the question we started on. What is the domain of philosophy versus what is more the domain of action? Where there are definitely problems that can be solved by philosophizing around them. I love those problems. Those problems are great in theory. But there are also tons of problems where you just need to go out and do the thing. And I would have them very clearly distinguish, what is the thing, which of these problems are problems of action versus problems of philosophy.

Jim O’Shaughnessy
Both good ones. On the nominalism, it’s funny, my son and I were just having a long conversation about, like, what is wrong with people. And one of his observations was, they have sufficiently made it so that they don’t have to come into contact with reality. In other words, they have sufficiently made it so that the box is there, as you put it, and they’re not opening it. They’re not going to look in that box. They’re just quite happy with assuming what’s in the box and saying, yeah, what’s in the box is true. And that is not going to get you very far. You’re going to have a. Yeah, it’s...

Brian Chau
A very Lovecraftian theory of knowledge, right?

Jim O’Shaughnessy
Yeah. And you’re going to have a look. George Box said “all models are wrong. Some are useful.” If you don’t upgrade yourself to a more useful model, you’re going to suffer, right? If you, as my son puts it, refuse to engage with and contact reality, guess what? Things aren’t going to go your way. And I just put up on Twitter the other day the Jed McKenna quote. If you’re having a little tea party between Lord Lion and Lady Gazelle and somebody comes along who doesn’t buy your fantasy narrative, it isn’t that they are mean, it’s just that your fantasy narrative is a bit fragile, and contact with reality destroys that fragility, I think.

Brian Chau
Oh, absolutely.

Jim O’Shaughnessy
Brian, this has been a ton of fun. I wish you the greatest of success with Effort News, and we will reschedule you to continue the conversation.

Brian Chau
Yeah, this was fantastic. You’re really an amazing interviewer, Jim. And see you next time.

Jim O’Shaughnessy
See you next time. Brian, thanks for coming on.

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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!

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$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.

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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.

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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.

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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.

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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.

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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.

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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.

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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