My friend Packy McCormick is one of the most thoughtful writers in tech and investing. He was also one of my early guests on the show, all the way back in September 2021.
Today, Packy returns to talk about why writing is still the most powerful way to think clearly, how optimism becomes rational when you spend time with people actually building things, and what happens when the internet punishes you for being early and wrong.
I hope you enjoy this conversation as much as I did. We’ve shared some highlights below, together with links & a full transcript. As always, if you like what you hear/read, please leave a comment or drop us a review on your provider of choice.
— Jim
Links
Highlights
The Best Ideas Are Written
Packy McCormick: I talk to founders all the time who are 10 to 1,000 times smarter than I am, and they have these incredible ideas, and they don’t write them because writing is hard if you don’t do it all the time. I actually tried last year to write less frequently. I thought I’d give myself more space and I’d come up with these beautiful big pieces. It’s actually harder if you don’t just go. So this year I’m just going. But they have all these ideas. […] There’s just all these really interesting ideas that people have earned because of what they do, or that they are doing what they do because of this idea that they haven’t written down anywhere. Maybe they’ll write it down in a company blog post, but those are 500 words. And even the best ones are not the full thing. I think people really like the opportunity to go long and have a canon document where it says, this is how I look at the world and why I’m doing the thing that I’m doing. Or this is something really interesting that I’ve learned. I like reading. I listen to podcasts all the time, but I get most of the ideas from reading. And so trying to bring more of that to the world.
Rational Optimism
Packy McCormick: I think I’m naturally optimistic. And I think one of the things that made ‘22, ‘23 weird and made me write a piece called Optimism, then we started this Weekly Dose of Optimism, was that people seem so, at least in our part of the Internet, so down in the dumps. Meanwhile […] the people that we get to talk to every day are doing these unbelievable things that if 5% of them are right, the world is a much better place. And nobody else knows about this stuff. And so it’s kind of like, I’m naturally optimistic. I will look at, I think crypto is a great example. I’ll see that, and I’ll see the positives of what crypto can be way more than I can see what all of the downsides will be. And so it’s not a purely positive thing to be that kind of optimist. There’s rational… I’m not just a total dumb optimist. But that was a real dissonance for me. Getting to see what I saw every day and having people be like, the world is so bad […] Even just three years ago, there was, was it the Atlantic, that article, “How could you possibly have kids in a burning, drowning world?” Or something like that, that I wrote a long response piece to. When you talk to all these companies in nuclear, in solar, in batteries that are doing the actual work to fix the problem. And so I think my natural optimism just was met with this goldmine of all of these people who made me more and more optimistic. So I wanted to go fight the fight.”
🤖 Machine-Generated Transcript
Jim O’Shaughnessy
Packy, welcome.
Packy McCormick
Great to be here.
Jim O’Shaughnessy
You know, I was looking back at the first time you were here, and you had the Not Boring newsletter, which I love. I’m also a subscriber to the paid version.
Packy McCormick
I saw that. Thank you.
Jim O’Shaughnessy
Love your stuff. But you were about 70,000, I think this was in 2021. And, you know, one of my producers said you actually made the announcement of your first $8 million fund on that show. Is that true?
Packy McCormick
I think that might actually be true. I think it was a little leak before there was any official announcement.
Jim O’Shaughnessy
That’s really cool. You’re like king of Substack. You’ve got 250,000. And so, first off, congratulations. But, you know, we just share so many ideas in common, and one of them is about writing. Talk to me about your passion about you got to write it down.
Packy McCormick
Yeah. So I recently just launched Paid. My whole thing with Not Boring in the beginning, I was going to go paid, and then I was having so much fun with it growing that I was like, I just don’t want to limit this in any way at all. I’m going to keep it free. And it’s been wonderful. It’s grown really well. But recently, I think because Substack has these leaderboards, and you’re not on them if you’re not paid, I was like, I need to do something paid, but I don’t want to put my stuff behind a paywall. So what is it? And I was thinking and thinking. I thought about a bunch of different ideas, and then I realized I was just sitting there thinking. I listen to a lot of podcasts, but I couldn’t think of the first time or the last time that I heard a new idea that had been formed on a podcast or in video that really stuck. And then you think about writing. You think about all the Ben Thompson and aggregation theory, everything Chris Dixon’s written in tech. There’s all these canon pieces, and they’re all written things. I talk to founders.
Jim O’Shaughnessy
All you need is attention. Attention is all you need.
Packy McCormick
Attention is all you need. And so I talk to founders all the time who are 10 to 1,000 times smarter than I am, and they have these incredible ideas, and they don’t write them because writing is hard if you don’t do it all the time. I actually tried last year to write less frequently. I thought I’d give myself more space and I’d come up with these beautiful big pieces. It’s actually harder if you don’t just go. So this year I’m just going. But they have all these ideas. And so last year I was having a conversation with this guy, Anjan Katta, who makes the Daylight tablet, and he had this idea. We were just texting back and forth. I was like, we should write that. And he’s like, I don’t write. I’m scared of writing. I was like, you send me voice notes and I’ll write it for you. And it went really well. And so I decided to try to get people to write their very best ideas down. I’m trying to figure out what the right format is. So we just did one on robotics, and it was this company thesis that robotics should actually iterate in small steps instead of there’s not going to be a moment where robots just wake up and can do everything. You need to collect all of the data. And so that was one. I have another guy who’s going to be writing about how the cartels move money because he works in fraud. And so trying to figure out what.
Jim O’Shaughnessy
I thought you were going to say because he works for the cartels.
Packy McCormick
Because he works for the cartels. He’s a good friend of mine. But there’s just all these really interesting ideas that people have earned because of what they do, or that they are doing what they do because of this idea that they haven’t written down anywhere. Maybe they’ll write it down in a company blog post, but those are 500 words. And even the best ones are not the full thing. I think people really like the opportunity to go long and have a canon document where it says, this is how I look at the world and why I’m doing the thing that I’m doing. Or this is something really interesting that I’ve learned. I like reading. I listen to podcasts all the time, but I get most of the ideas from reading. And so trying to bring more of that to the world.
Jim O’Shaughnessy
Which I applaud. I kept journals all my life since I was a teenager. And literally, we have stacks and stacks of them. I think that writing is thinking.
Packy McCormick
Yeah.
Jim O’Shaughnessy
And I got in the habit of doing it. And all of us have these ideas bumping around in our minds, and if you just leave it there, you don’t really know until you try to write it out. Writing things out has killed more stupid ideas that I have had. And believe me, man, I have had a plethora of stupid ideas. But it is only in the writing. And I’m a big believer in writing by hand. And there’s some neuroscience that suggests that engages a different part of the brain and whatnot. But as we were talking about, I’m writing my first fictional novel right now, and kind of a system like yours, you’re co-writing with people. I have a writer’s room and I have some of the best writers in the world in there. And at the last session we had, I was telling you, I told them all about the story that I was building and it’s a thriller and the ideas that they threw my way, I was like, that is brilliant. And so I just, you know, it’s the way they do TV shows, right? They always have a team of writers. So it’s really fun experimenting with it. But take us back to the beginning, because your origin story is really interesting. You were at a company that wasn’t doing so well, and it was the writing that got you on this kick.
Packy McCormick
Totally. So my backstory started my career in finance, did that for a little bit, and then went to a company called Breather, which did on-demand meeting and workspaces. And the product was great. Everybody that I tell that I worked at Breather, oh, we use Breather, we love the product. But the business model was take a five-year lease, do construction, and then rent it out for an hour at a time. And so if you think WeWork’s business model is bad, where you do it for months at a time, we did it for hours at a time. And when it works, it really works because you can charge a lot more for an hour than you could charging for a month hourly. But often it didn’t work. It was compounded by the fact that we had the same investors as Uber and they were like, the thing that you need to do is expand your supply as quickly as humanly possible. Because that’s what Uber did. And it worked for Uber. Uber didn’t sign five-year leases and do construction. We did. And so we ended up with this glut of supply on the map. I think we launched one of these little office spaces every day for an entire year, which is also managing to the metric. We would put a wall in the middle of a space that should have clearly been one space just to be able to get two spaces on the map. But we did it and we were deeply oversupplied. Some spaces, like right around here in Union Square, did really well, a bunch of other spaces didn’t. And so a coworker of mine, Ben Rollert, and I took Christmas break and we came up with a plan to fix the company. And then we wrote the whole thing down. We had read Good Strategy, Bad Strategy by Richard Rumelt. We were high on business strategy. We wrote the thing down, we presented it to the rest of the exec team. They actually gave us, you know, we needed to do something because our margins were negative 25% and we had these fixed leases. Oops. So we did that and then we sold it to the rest of the company. And it meant for a lot of people, if you were somebody whose job it was to set up a space and it was supposed to be set up one way, we said, all of a sudden now, instead of just doing hourly and daily, one space could be hourly. But if it’s underperforming, we’re going to sell it monthly for as low as we can still make money. And then maybe somebody wants it hourly and we want to switch it all back when they’re done. People’s jobs got a lot harder. The sales team had to completely change what they did. And everyone read this thing and everyone got really into it. The idea made sense and it was clear and we put it down on paper. And so that was the first time that I was like, wow, writing actually can change the way that people even work inside of a company. If you can communicate an idea clearly. It worked for a while. Margins went up to positive 25%, which isn’t going to win a Nobel Prize for business, but certainly was better than it was. Did that for a while. Finally, we brought in a professional CEO. We tried to be mini WeWork with a thousandth of the resources. And then I left because I could see the writing on the wall. And then COVID hit and the company fell apart. But I had taken David Perell’s writing course during that whole process. And so when COVID hit and I couldn’t start the physical space-based thing that I wanted to do, I decided to just start writing online for three months. We had just gotten pregnant with our son Devin, and I begged my wife to let me write and she did. And it just started growing. I didn’t make a dollar for nine months, but I was doing the math and I was like, soon I’ll turn on paid subscriptions and if I get a 5% conversion, then at least I’ll maybe be able to pay for rent and food and hopefully insurance if things go really, really well. And then one thing led to another, and here we are.
Jim O’Shaughnessy
I’m a friend of David’s. In fact, we gave scholarships to Write of Passage at O’Shaughnessy Ventures. Let’s talk about that a bit. Were you uncertain of how good a writer you were? What was the reason to take David’s course?
Packy McCormick
The reason to take David’s course was I wasn’t writing. I liked writing. I had maybe a couple of Medium posts, maybe published, maybe just in Google Docs somewhere. Word at the time. I had written… I was a philosophy minor in college, so I wrote a little bit for that and did well there. In high school, I liked being the class clown, but writing well enough that I could still get an A, even if it was a little bit of a satirical piece. And so there was something there, but I was never a writer. I took the course because I saw a tweet and I had said the word enumerate in one of our exec meetings, and I got looked at like I had seven heads and got laughed at. And I was like, well, if I don’t do something here, my brain’s going to fall out of my head. And so I took his course because I saw a tweet that next day, and I was like, yeah, that sounds great. I’ll do something just so I can keep my brain going. And I think what it was really good for was one, just confidence. The first day, there were 50 people in the class. The first day we had to write an essay on one of our favorite Internet writers. And so I wrote something on Ben Thompson’s work, and David called it out as the best piece in the class. And I was like, whoa, I might actually be a writer. This is really cool. And the other thing was just showing up every week and having to write something, but then having to get it edited by your small group. And if you were the asshole who showed up with nothing, then you couldn’t really contribute to the group. You’d break out in small groups on Zoom. And so that was really helpful. And then he had a few, I think, really helpful concepts, the most helpful of which was the idea of a personal monopoly, which sounds cheesier than it is, but it’s really just pick a bunch of your different interests and overlap them until you find something that you’re the only person in the world who’s going to be good at writing or you’ll be the best at writing about that thing. And so I went from being like, how am I going to write about tech when Ben Thompson exists? To going, well, if I combine tech and pop culture. And so I wrote stuff about the Mickey Mouse Club and Joseph Schumpeter and then maybe a little bit of Philly sports. There’s nobody at that overlap. I can win that overlap. And so I started from there and it was very on the nose in the beginning. Here’s this business and tech idea and here’s this pop culture idea and I’m just going to combine the two of them. And I would force myself for the first six months to write about both. That got to. I mean, it was picking two essays. But I’ve tried to keep the tone from that as I started writing a little bit more seriously.
Jim O’Shaughnessy
As you’ve gotten bigger, have you had to deal with audience capture?
Packy McCormick
I think a little bit. The whole thing is a rollercoaster. You know, talking about, I started writing about a topic that you’re bound to fail X percent of the time. I’m writing about startups, so you’re going to be wrong a large percentage of the time, just naturally. But you don’t have the upside that you would in a venture portfolio because you’re not going to get 1000x on your essay. And I was doing it as a new writer on the Internet very publicly because it started growing in the beginning. So I think I had a really fun first two years and wrote a lot of stuff that I’m proud of, but also was totally wrong. And so I think there was more than audience capture. There was just a period for a couple of years, actually where I was just way less confident. And so I’d try to write about things that I thought would do well. And something changed, I guess, the past year and really now, I do not care. Last year I was writing, I wrote 40,000 words on the electric tech stack. I wrote this piece Means and Meanings that we were talking about before, which is more philosophical. I’m a philosophy minor 16 years ago. I’m no philosopher. And then all manner 33,000 words on an Internet startup in Colombia, just whatever I find the most fascinating, I think that comes across on the page. If I find it fascinating, I’ll do a better job on it. And other people will too. So I think I’ve done largely a good job at avoiding audience capture. It was more of just a confidence thing, I would say, in the middle.
Jim O’Shaughnessy
Yeah, I remember. Correct me if I’m wrong, but you went through a period where everyone was being really mean to you.
Packy McCormick
It was a short period. So I am still fascinated by crypto. I think open, decentralized networks are this beautiful thing, but they also, I think I underestimated because I’m this optimistic, that if people see the opportunity to do bad things, they will. And there’s nothing more of an opportunity than an open, decentralized network full of money to attract the cryptos. And so stablecoins are doing really well. Bitcoin is doing, in turbulence, what it’s supposed to. I moved to that in my flight to safety during liberation. There’s a lot that I still really love about crypto, but I got fascinated by it. I was writing about it a bunch in 2021 and 2022, and when that tanked, I got beat over the head with that. There was one in particular where I had gotten on a podcast, Logan Bartlett’s show with Zach Weinberg, when he was. This was the first of a series where he just started ripping anybody who did anything related to crypto. And it was 8 at night, and my son had just thrown up on me and I wiped off my shirt and got on the podcast. And then Zach was like, what’s one real use case for crypto? And so I pulled something out of my ass. And I was like, you know, mortgages on the blockchain, something like that, just was not thinking. And he ripped me apart, which was fine, except this guy Loren took the clip and it went super viral that I was this complete idiot. And that all started happening while, you know, the throw up had turned into RSV. And we were in the hospital with my son. So I was sleeping on the floor of the hospital, looking at Twitter with the whole Internet dunking on me. And it was just the worst possible experience. And so that was actually, I think, a confidence turning point. And not just me, I think actually… and I don’t think I’m just feeling this… I think people lost confidence in anything that I said after that experience, which at the time was brutal. And now I think it was the greatest thing in the world. Because one, I think just going through that, you realize it actually doesn’t matter and people forget. But then two, because now, I don’t know, that’s the worst it’s going to get on the Internet. And it wasn’t that bad. And I think I probably was for being such a novice investor writer. I probably did have too much hubris and confidence in what I was writing. And I think that made the writing fun and fresh. But it is a weird experience to start as a novice on something with that much visibility because now I feel like I’m a 10 times better investor. I probably know what I’m talking about on the writing side and I’m a better writer, but needed to go through that you’re not that hot shit to get to this point.
Jim O’Shaughnessy
I remember when I, because I did see that clip on Twitter and I thought at the time that might be the best thing that ever happened to him. Because I went through something similar. But we didn’t have an Internet during the dot-com boom. All of our stuff was large cap value or small cap growth, which were in nuclear winters back then. I got attacked by the Wall Street Journal, by Jason Zweig, who’s now a good friend. I got attacked in books. In books. You know, O’Shaughnessy should have called his book What Works on Wall Street Until I Wrote This Book. And it was fucking brutal. But in hindsight, it was absolutely liberating because, you know, you gotta get punched in the face.
Packy McCormick
Totally.
Jim O’Shaughnessy
You learn to be much more humble.
Packy McCormick
I could not agree more. It was such a weird time. Just COVID in general on the Internet was weird and everything was moving so fast. And I just had this belief that, I remember I can’t name the company, but there was this company that was like, would you, instead of doing what you’re doing, would you take this absolute dream job? I couldn’t have made up if you told me, make up. I wouldn’t have because it would have been too cool of a job. And I was like, no way. Because next week someone’s going to offer me something even cooler. That was the way that it felt. I’m making myself probably sound like more of an asshole than I was, but it just on an upward slope, it really felt like things were just going to keep going and at some point they’d just be like, do you want to be the president or something? Which would be a terrible job also. And so really to get punched in the face and really think I have to go back and figure out what I care deeply about and want to write about and invest in and all of that. Greatest thing that could possibly happen.
Jim O’Shaughnessy
And my thesis is that it’s required. If you don’t have scar tissue, you’re probably not going to make it. And you get scar tissue by just continuing to persevere and becoming a lot more humble. But one of the great fears is people are terrified to fail. And more importantly, they’re terrified to let other people see them fail 100%. And what I always try to get them to understand is that’s the only road to succeed, right? Because that’s the way it works. And so it just sometimes drives me really crazy when I talk to incredibly talented people and I’m like, you should write a book or you should start a company. Or they’re like, nah. People listening right now. What advice would you give for that kind of person? How can you be brave and actually do it? Because nobody will remember.
Packy McCormick
No. And we’re past that hopefully now. I wouldn’t even say it was from that. It was from the very beginning when I started writing. I’ve told the story before, but I legitimately thought if I start writing on the Internet, as a guy who didn’t, I mean, I worked at this startup that was failing at the time, and now I’m like, here’s what I think about startups. That at the very least, my friends were all going to have a group chat going where they’re like, what is Packy doing? Is he okay? He went from finance to a failing startup to now he’s writing a newsletter called Not Boring on the Internet where he talks about the Mickey Mouse Club. What is going on here? And the truth is that one, people are nicer than you. I went to the playground this weekend with my son. I wrote a little thing on it and he sold for the first time. He made these donut hats out of Play-Doh and put tape on them and went to sell them. Was going up to grownups after getting over his nerves. And he afterwards, I guess like father, like son, just started telling me to write down the lessons that he learned. One of which was, people are nicer than you expect. And so I think that is actually, that is one of them. The other is that people just don’t care. You have to fight for their attention. So if you’re not doing good work, people just don’t waste a second thinking about it. And if you are, it’s only upside. Of course, there’s the downside of getting punched in the face and all of that, but I think it is so asymmetric, the upside for the downside, because it is so hard to grab people’s attention, positive or negative, and even if it’s negative, to hold their attention for more than two hours.
Jim O’Shaughnessy
Yeah. And the other thing you were early on, which was one of the reasons why I was intrigued by you back in ‘21, was optimism. I am what I call a rational optimist, a Deutschian optimist, I guess. I had reread his. I read the book when it came out, The Beginning of Infinity, and I liked it and I enjoyed it and everything, but then I reread it and I got so much more out of it. The second time I read, I did a thread on Twitter. But back then, it was kind of hard to be an optimist. You were really going countercyclical. Are you naturally optimistic?
Packy McCormick
Yeah, I think I’m naturally optimistic. And I think one of the things that made ‘22, ‘23 weird and made me write a piece called Optimism, then we started this Weekly Dose of Optimism was that things like, people seem so, at least in our part of the Internet.
Jim O’Shaughnessy
Yeah.
Packy McCormick
So down in the dumps. Meanwhile, you know, we have mRNA vaccines, and then just everything that’s come out of that, we have now what is AI. We had tech companies that are actually going back into the physical. The people that we get to talk to every day are doing these unbelievable things that if 5% of them are right, the world is a much better place and nobody else knows about this stuff. And so it’s kind of like, I’m naturally optimistic. I will look at, I think crypto is a great example. I’ll see that, and I’ll see the positives of what crypto can be way more than I can see what all of the downsides will be. And so it’s not a purely positive thing to be that kind of optimist. There’s rational. I’m not just a total dumb optimist. But that was a real dissonance for me. Getting to see what I saw every day and having people be like, the world is so bad. We have all these problems. Climate change. This is. It’s crazy. It feels like people don’t think climate change is going to kill us all anymore. But even just three years ago, there was, was it the Atlantic, that article, how could you possibly have kids in a burning, drowning world? Or something like that I wrote a long response piece to. When you talk to all these companies in nuclear, in solar, in batteries that are doing the actual work to fix the problem. And so I think my natural optimism just was met with this goldmine of all of these people who made me more and more optimistic. So I wanted to go fight the fight. Now it feels like we’re just preaching to the choir, because I think everyone’s gotten more optimistic, or not everyone, kind of in our world, at least. But it was very weird for a little while there that people were so pessimistic.
Jim O’Shaughnessy
Yeah. And I think one of the reasons for that is it’s so much easier to be a pessimist. You can naysay anything. I always look for things to root for as opposed to against, because, honestly, it’s fucking easy to root against whatever, and it’s lazy. And it bothers me, though, because I just see so much wasted potential. You know what I mean? And that time in particular, I was feeling like you. I was like, people, you know, honestly, it’s like that old Louis C.K. bit about having Wi-Fi on a plane.
Packy McCormick
Although it is frustrating now, but yes.
Jim O’Shaughnessy
Yeah, but where he’s like, I can’t believe it. I’m 30,000 feet above the air and I can scroll on the Internet. And he goes, then it goes out and you go, what the fuck?
Packy McCormick
Yeah. Everything is amazing and nobody’s happy. I think it was his punchline on that one. And that’s exactly how it felt. And then you had everybody, people who were. I remember listening to one All-In podcast when Chamath was like, I can’t believe people got so irresponsible during. I was like, what are you… People? Come on. And so it was not just the pessimism, but it was the people who led the parade were like, what were you guys?
Jim O’Shaughnessy
You are exhibit A, my friend.
Packy McCormick
You are exhibit A, my friend. And so it was just all of that combined. But I think now, hopefully, people are feeling more optimistic about things.
Jim O’Shaughnessy
Yeah, I do sense that it’s kind of a regime change and the idea that everything’s going to shit is losing ground maybe for the first time in a long time. What do you think some of the reasons for that are?
Packy McCormick
I was just going to ask you that.
Jim O’Shaughnessy
I’m lucky that I’m on the host side of this conversation. Make you do all the hard thinking.
Packy McCormick
I think in our part of the world that’s probably true. I think there still is a lot of, if I say anything good about AI on the Internet still, you’re going to get a bunch of people like, are you kidding me? This is the worst thing in the world. It’s going to kill the planet. It’s going to, I can’t believe you would even use this. And so I think there are plenty of people who are still pessimistic, and rightly so. And you know, the job market can be tough for young people. So I think it’s our part of the world and that’s the part of the world that I know best. Tech and VC. But I think in our part of the world, you get punched in the mouth enough a few times in a row. There was COVID, everything was going to fall apart. And then it did really well. And then ‘22, ‘23 happened and then we’re saved by AI. And then you look around at just again, all the things that are happening right now. I saw Mario Gabriele did a podcast with the founder of Reflect Orbital today. So now we have satellites that are going to reflect the sun’s beams onto solar farms to keep solar farms operating 24/7. And all of this stuff is actually really happening. In the past week, the DOE and NASA said that we’re going to put nuclear reactors on the moon. And then a company said that we’re going to put hotels on the moon. And probably neither is going to happen on the expected timeline. But the fact that we’re actually talking about these things as plausible things is absolutely amazing. What’s happening in medicine is unbelievable. Ozempic and the like are miracle drugs. My friend who used to work with me, Elliot Hirschberg, wrote a piece on the GitLab founder yesterday and his attempt to cure cancer. He was diagnosed with cancer. He’s this great systems thinker, and he’d gotten to the end of the line and they’re like, sorry, bud, this is the end of the line. And he’s like, well, that stinks. That’s not how I want this to end. And so he just flew around the world and came up with all of these different ways to test himself and do different trials on himself. And because he had a ton of money, he was able to be this n of one character who could go figure it out and went into remission and actually beat this incurable cancer. And Elliot’s point was, the thing that this guy is doing is this very bespoke thing that only one rich person can do today. This is going to be accessible to all of us very soon, maybe 20 years. And medicine takes a while to change, but that is incredible if we’re getting to the spot where, one, early detection of cancer really helps. But then, two, we have a bunch of therapeutics that are coming to market that could help just beat it once and for all. It’s pretty hard to be too bummed right now if that’s the soup that you’re swimming in. Not to mention, it’s just, I think the amount of fun people are having impacts their pessimism or optimism. And it’s really fun to wake up every morning and be like, all right, assistant, go do exactly what I want you to do. And then I’m going to go focus on the thing that I want to focus on. The thing that even a couple of years ago we were all saying, which is the AI will do the stuff that you don’t want to do, and then you’ll do the stuff that you want it. Actually, for the first time right now, I kind of feel that where I just get to think about what I want to write about and write while I have this research assistant doing all this stuff for me. And it’s just a really fun time to be doing this. And so hopefully, I think the big important thing will be whether the benefits of all this diffuse and how quickly we can get all this tech that we’re excited about at the early stages benefiting actual people. But there’s just so much cool stuff coming down the pike that I think for at least for our world, it’s hard to be too pessimistic right now.
Jim O’Shaughnessy
It’s also a time when, you know, context is really important and a lot of people don’t have it. You know, I was saying on Drivetime when I was 11 years old, literally, women couldn’t get credit cards without their husband’s signature. My oldest sister, who unfortunately died, was married to a black guy from Trinidad. Their marriage was illegal in half of the states of the United States. I mean, really, seriously fucked up. And people who lack that context really can’t see how much forward progress we as a society have made. And when you know all of that, right? And then you see in just 50 years, the changes that America, I mean I would be hard pressed to find other societies that changed, I think directionally, in a good way, as quickly as the United States. And so context, I think is super important. But I also think that, you know, you’re talking about the AI and so we have our own AI hardware, software installation and we have a genius who’s programming it. You’re going to see some pretty cool things come out commercially ultimately from our AI lab. So one of the things I had the AI lab do was go through every innovation and find out the reaction to it. And there’s a thing called an ur pattern, which is a primitive pattern, right, that if you can extrapolate from that pattern, you can see really cool things. The ur pattern for innovation is unchallenged, go all the way back to writing. Socrates said, no, that’s a bad idea. And it follows the same pattern, right? So what happens, and the reason it happens, in my opinion is let’s take photography. When photography came on the scene, painters of portraits were really unhappy, right? And so, but it happens for novels, it happened for photography. Music, when records came out, symphony orchestras took full page ads out in newspapers saying, that’s not real music. Real music you have to hear live, right? So what’s really happening is the prior regime that was really good at that particular skill gets nuked by an innovation and they’re unhappy about that and they start coming up with every kind of reason. One of the ones that’s really interesting is they shift from outcome. So how should you judge a book or a piece of writing or a movie or whatever? Well, what did you get out of it? Did you enjoy it? Was it a good story? Did you learn something? Did you change your mind about something? Right? The outcome was what was important. What happens, and it happened across all of these innovations, they change the playing field and they stop talking about outcomes and they start talking about process, right? And well, no, if you’re using AI, which by the way, we use in every aspect of O’Shaughnessy Ventures and which I’m using in concert with my human writers. I literally could not be writing this fiction book without AI because the research alone, it would take me. I would have to hire hundreds of people and let them loose on libraries all around the world, and it just wouldn’t get done.
Packy McCormick
You know, that just made me think of that. It does take away the thing I was saying about, it frees you up to do the. For a lot of people, I think that’s uncomfortable to be freed up to do the creative. That is the hard part of this whole thing. And it is really comfortable to say, I can’t get my book out because I have to go to this library. And you can sit in the library for hours and you’re working on your book, and so you feel like you’re doing this really amazing, productive thing. And it, I guess, prevents you from doing the hard work of actually sitting there and thinking about what you want to write about and the questions that you’d want to ask AI and the research that you wanted to do when you have to move faster yourself. And so I’m sure a lot of this is just. I mean, people are bad at change, right? And so they’re used to doing something one way. Their identity is tied to one thing, and we’re bad at change.
Jim O’Shaughnessy
Yeah. And, you know, of course, the paradox. Everyone wants things to improve, but they don’t want anything to change. But then what’s interesting about this pattern is it gets overcome. And, you know, like, movies, when VHS came out, Hollywood spent millions of dollars trying to kill it. They lobbied Congress. They did every. I think the guy’s name was Valenti. And you would see him everywhere on the news. This is piracy. This is not the way movies were meant to be watched. They’re meant to be watched at a theater. And it was a big, huge thing. Until they’re like, oh, we might actually be able to make a buck on this. And then, of course, you look at their revenue streams, they’re making so much more money because of the innovation. And it’s interesting because if you know about how things get innovated and found, I was just reading this great book, The Story of Money, and the piece on Gutenberg is amazing. So Gutenberg was basically a grifter. He was a jeweler. He was obsessed with striking it rich. And not only was he a jeweler, he grew up in wine country. And so wine presses, he was looking at those. The problem with printing before Gutenberg was people had come up with stuff, right. But they could never give uniform pressure when they published it, down to the ink, and so it smeared all over the place. And everyone thought, this is awful. This is horrible. And he figured, no, because he was a jeweler, he could do the fonts much better because that’s what he was trained to do. And then he figured out the way to make the pressure thing. But do you know why he did it? Because he wanted to get rich. And literally the only game in town was the Catholic Church. And so back then, it’s such a great story. Back then, the church was making bank on so-called letters of indulgence. Basically, they were selling you heaven tickets.
Packy McCormick
It’s amazing.
Jim O’Shaughnessy
But there were so many people who wanted them. There was a supply, demand, mismatch, because all of them were done by a scribe with a quill, with the fancy letters and calligraphy and everything, and then signed by the bishop. Right. So even though there was a demand for 100 of these letters, they could only produce 10. And so Gutenberg goes to the local bishop and shows him a printed letter of indulgence. And the bishop almost wets himself. Where do I sign up? They finance him. He gets all the financing from the Catholic Church, which, by the way, was also the lender of choice back then. And the bishop is thrilled, he loves it. But Gutenberg is like, no, I gotta do more. And his eyes set on Pope Pius II, by the way, anything but pious. He had kids in different countries. He wrote erotica.
Packy McCormick
Yes.
Jim O’Shaughnessy
He was also incredibly vain. And because he wrote so much, his eyes started to go. And the thought of having to wear glasses to read to a congregation really offended his vanity. So Gutenberg did a Bible just for Pope Pius. It was beautiful. Being a jeweler, the cover of the Bible was all encrusted with beautiful jewels. But when you opened it up, the fonts were this big so that he could read it without glasses on. And Pius was like, where do I sign? And so literally, they gave him all the financing. But they didn’t think, because they thought, this is amazing. We’re going to get 100x the revenue from the letters of indulgence. We’re going to get these beautiful Bibles. But he forgot that there were other people who might use the printing press too. Enter Martin Luther. But even that Luther came from mining country and they were in a huge bear market. His whole family was in it. And so he got triggered when the Pope sent the prelates and everything to his town to raise money for the beautification of the Vatican. And they’re all in these incredibly fine robes and everything. Meanwhile, Luther’s family is starving and he’s like, fuck that. And thus you got thesis nailed to the church wall, man.
Packy McCormick
They need to teach history differently because this is so cool. And I did not know any of this.
Jim O’Shaughnessy
I didn’t either until I read this book.
Packy McCormick
Did he get rich?
Jim O’Shaughnessy
He was profligate. So he was basically the old-fashioned term for him was he was a bounder. And what’s really fascinating about it is the real history is so much more interesting than what we’ve been taught. Before reading this, I always thought of Gutenberg as this very studious academic type guy. No!
Packy McCormick
I also picture everybody from history as old. Almost same with me. The last portrait they have is what you picture them as. And not a vital young farmer or whatever.
Jim O’Shaughnessy
But the second order effects of publishing created everything. And it gave us the ability for the first time in history to time bind our ideas and send them forward into history and the profound changes of that. But then again, the book I’m reading is The History of Money, right? And The Story of Money. And what was another reason Lutheranism and Protestantism took hold? Well, all of the. Because Germany was a confederacy of duchies. It was not a unified country and they were all competing with each other. That’s why it took hold there. Because as the author of the book points out, the Chinese had already figured out printing, but because they were centralized under the God king of the emperor, they squashed it. They didn’t want ideas that were not supported by the emperor to get out there. In Germany it was like the Wild West. And so all of them could get out. Pamphlets got huge. The thing about Martin Luther, he was literally one of the bestselling authors of all time at that time, but it was all pamphlets. And the key thing was the priesthood spoke Latin. And I always joke that the priesthood says the incantations in Latin because they don’t want the laity to know what they’re on about. And Luther published in German, it was the first time ever. And so most people were illiterate, right? And so the pamphlets were meant to be read in the town square and they were. And then he published hundreds of thousands of these pamphlets. And they made their way all across all of the city states of Germany. And then the princes of those states were like, you know, if I convert to this new form of Christianity, I can seize all of the church’s lands. It’s a, you know, follow the money.
Packy McCormick
Wow.
Jim O’Shaughnessy
And so they’re like, yes, please. I mean, Henry VIII. Yeah, he wanted to get married a couple of times, but the thought just had him salivating that I can seize all of the church’s lands if I convert and you know, Protestantism is born.
Packy McCormick
Humans are amazing.
Jim O’Shaughnessy
We are.
Packy McCormick
Humans are really amazing.
Jim O’Shaughnessy
We really are.
Packy McCormick
I mean, yeah. The fact that so much innovation comes from greed and war is a very weird feature of humanity.
Jim O’Shaughnessy
Yeah. But I mean, it makes sense, right? Of course. And you know, also in this book, do you know what a florin is?
Packy McCormick
Yeah, the money.
Jim O’Shaughnessy
Yeah, the money. Florence minted the florin and created the world’s first reserve currency because it was, you know, 25 karat gold, always uniform. They had the. It was done by merchants. Right. Church was very unhappy about that. But they literally became the world’s reserve currency because of liquidity. And that’s what created the Renaissance, was the ability to trade in your own currency. Because literally the US dollar gives us inordinate privileges and crazy privileges. When you can. When the world uses your currency to price all of the other goods, you have advantages that simply don’t exist for other things. And the same thing happened over in Florence. So one of the ideas that I think somebody like you should explore. There is so much alpha sitting in history books when you start seeing these connections. And this was new for me. I had heard about it earlier, but that’s why I picked up the book and reading it, I’m like, this is amazing. And you know, I learned that Fibonacci, his real name was Leonardo of Pisa. I think he wrote the first bestselling business book.
Packy McCormick
No way.
Jim O’Shaughnessy
Yeah. And it was written for merchants and it was basically defined the time value of money. And it was the book that made lending take off, that made all of it. Took it away from the church and.
Packy McCormick
How do we not know this?
Jim O’Shaughnessy
Same with me, dude. I’m a late night guy. And so I read every night and last night I’m just like, I can’t stop reading this book. This is amazing. But it’s almost kind of like a hidden history. Because it’s the real history.
Packy McCormick
Yeah.
Jim O’Shaughnessy
So the dynamism of eras, sometimes they’re really short lived. Back to Florence. Right. The Florence of the Renaissance was a marvel and it was done by merchants like the Medici. Do you know what that name derives from? Medici. It derives from medicine. They were doctors that I did not know and they were founders of the doctor’s guild and then they took the name Medici. But the church, talk about a network. The church had the most incredible network on earth. Still probably has pretty good network on Earth. But literally they were like, yeah, no this has to stop. And so they sent this crazy monk. And that’s where the term Bonfire of the Vanities comes from. He went and he convinced all these people, you’re going to hell. You are definitely going to hell because of your vanities, which was beautiful art, beautiful furniture, all that kind of stuff. And so they literally had bonfires. A beautiful thing, you know, Florence. One church catches up. But it’s a long winded way to get your opinion on. I think that there are certain elites who really don’t want things to change that much. And what do you think about that? I kind of think we’re entering a battle, but it’s a battle of elites, but it’s intra elite. And I kind of say one side is the Empire and the other side is the Rebel Alliance.
Packy McCormick
Who do you think is on each. Are there surprising people that you would put on each side? Are there surprising factions?
Jim O’Shaughnessy
So World Economic Forum is the Empire. The guys at a16z are the Rebel Alliance. I count myself as a member of the Rebel Alliance.
Packy McCormick
I’m also in the Rebel Alliance and I think that’s completely right. And I think this is not an AI thing. This started with. I think social media probably was a huge driver of this, that anybody could go out there and say the thing that they believed and compete for attention. I think there’s been some bad things about social media and there’s been some very good things about social media, this being one of them. I think Davos is going on right now and I guess there’s a lot of people there that are important, but who cares? And you’re not waiting for Davos to tell you what’s going to be important this year. And it’s actually maybe a negative signal, whereas. I just wrote this piece on a16z.
Jim O’Shaughnessy
I read it. Yeah, I thought it was really well done.
Packy McCormick
Thank you.
Jim O’Shaughnessy
My friend Alex Danco is going to tear that place. I mean, he’s so smart.
Packy McCormick
I’ve called this to people recently a divinely inspired hire. And I think it is. I think Alex Danco is amazing and I was shocked to see it. But it makes all the sense in the world when you think about what they’re trying to do. The impact that he can have by making all of. I mean, it’s kind of what I’m trying to do in a small way with just a16z scale resources and Alex Danco level talent is a pretty crazy thing to think about. But I think one of the things that does not come off about them is how humble they are almost in their philosophy, which is just if there are smart people out there doing a thing, even if we don’t really fully understand the thing yet, we’re going to go find the very smartest of the people who are doing that thing and we’re going to back them. And in that case, they built the best machine to be levered to things being different and better in the future, whereas the empire is levered to things staying exactly the same or they benefit from things staying exactly the same. So there’s just that natural tension there. And I think that’s happening in a very big way. I mean, my whole thesis, and this is another one that maybe seems less interesting now than it did a couple of years ago, like optimism, but just that I think people underestimate just how quickly the largest companies in every industry can change. I mean, and how much bigger those companies will become when they do. The fun example, I mean, like SpaceX obviously, but they were competing with a dead launch market Anduril I think is a really fun one because let’s say you get to even a quarter of the Prime’s revenue, but you’re doing it at 40% margins as opposed to, you know, contractually guaranteed 8% margins. And you’re growing faster. That just becomes a much bigger company. And the world keeps getting bigger. Obviously Internet businesses just have a much larger TAM. And so I think things change really fast, but then I think, you know, the established elites and incumbents more generally are just going to get flipped really quickly. And that is a scary prospect that you can only fight dirty essentially because you’re not going to win the technological battle, you’re not going to win the battle for talent. And probably as a Boeing, you’re not going to win the battle for hearts and minds. And so yeah, I think you’re absolutely spot on that that battle seems to be happening.
Jim O’Shaughnessy
Well and I also think that this is kind of a unique time where for example, the number of people who said to me, why the hell are you opening a publishing company? Well, because the inefficiencies of the. I love to say that. And look, I owe a tremendous amount of my success to the four books I wrote, right? Especially What Works on Wall Street. I was absolutely. My career was turbocharged by McGraw Hill and by other publishers that I published with and loved. Right. But by the same token, the innovation just isn’t there and we now have the tools, right, the means, as you would say, to make meaning for our human readers. And you know, some of it is just so simple. And the fact that they’re not adopting it’s not because they’re stupid. They’re not. There’s a lot of really smart people running legacy publishing companies. But they feel that they need to be backward compatible to the way they used to do things. Right. And so, and they’ve got tons of employees that, you know, who wants to be in the Wall Street Journal for mass layoffs and have those put at the foot of technology, technological improvements. Right. So we can build one from the ground up. And that’s what we’re doing.
Packy McCormick
Well, a lot of people, I think, experience publishing and then said, we’re definitely going to go build a better publisher. I think a lot of people have tried something like this. What do you think people get wrong and what are you doing differently there?
Jim O’Shaughnessy
I think that the traditional publishers are still very much based on status and prestige and they want to be a little mysterious. So, for example, if you’re an author, I still get statements from What Works on Wall Street, but I get them twice a year, royalty statements. I have no idea how they’re calculated. It’s literally a sheet of paper with a check. Which is nice. But they are, in my view, the author has become incredibly underserved by traditional publishing. We are looking at authors as stars and we are going to do everything in our power to make them stars. What does that practically mean? It means that you don’t have a two-week window to market a book. You have a window that never closes. We have AI workflows, we have team members who are constantly monitoring the books. And then we continue marketing it forever. Boys in the Boat. When it came out, nothing, just fun. And it was because they didn’t really think about the fact that, you know, we should probably send this to rowing crews or things like that. And so I don’t know, I’m sure I’m getting the timing wrong. But like six months later they give a two-week window usually to marketing a book and then move on because they have to.
Packy McCormick
Yep.
Jim O’Shaughnessy
Six months later, I think the author himself, Jimmy Soni, my editor in chief, knows this better, but was like, you know what, I’m just gonna start giving this to rowing clubs and all that. And it absolutely exploded. It sold, I think, you know, hundreds of thousands.
Packy McCormick
I read it, yeah, I read it.
Jim O’Shaughnessy
Got made into a movie. The other great example is Slow Horses, which they have on Apple TV now. The story of that is crazy. His publisher there said, no, this type of writing isn’t your lane. And they’re real big on lanes. Right. We erase lanes. But the other thing that we’re doing is we’re faster. We are publishing a book that the author really wanted it published at a particular time. She went to the big publishing houses. They’re like, oh no, that’s going to take three years. We’re like, we’ll do it for you. Utter transparency to the author. They’re going to have dashboards that show where they’re selling, where they’re not. They’re going to be able to see that hopefully in real time. Ongoing marketing, much greater share of royalties. Basically the model is 50% until we recoup our expenses. 70% to the author, 30% to Infinite Books. How can we do that? Technology. That’s the only way you can do it. We look at the author and the reader. Those are our clients. If a book just fits our thesis as well, we can get it done for you really quickly. We market it much more extensively and you’re going to make a lot more money. Literally one of our goals internally. And Jimmy’s going to hate me for saying this in public, but we want to turn every author that works with us into a millionaire. And we can. Right? And that’s just a different way of thinking about it. And you know, simple things like A/B testing, cover art, why are they not doing that?
Packy McCormick
What I love about this answer is I think a lot of people see AI and technology and they’re like, we’re just gonna be faster and that’s half of it. But the counter positioning piece or understanding where legacy is stuck respecting them realizing they’re smart, but knowing that either because of tradition or probably because of business model, they’re stuck doing a particular thing. So if you can run fast at that weak spot, then that’s the holy grail there. That’s really cool.
Jim O’Shaughnessy
Absolutely. And you know, kind of our internal mantra is we only do win-win things. We’re not going to do anything, any zero sum, we’re not going to do anything that disadvantages. And I’ve been like that for a long time. So, for example, we got a lot of opportunities back when the payday loan companies were coming online. And I was just like, no, I will not do that. Because that’s predatory lending on the people who can least afford it. No. And then after we sold OSAM, I’m like, you know what? I think I’m just going to make that the mantra of the new company. It’s just everything has to be win-win. And the way we look at it is the author is going to win huge. Right. Because they’re going to have a view into their books and writing that they’ve never had before. And authors are very clever people and they’re going to be, oh, I didn’t even think about that. Yeah, I should do that. That and this and that and they’re going to get a much greater share of the revenue again because the margins work for us because of technology. I just think that cultural evolution, company evolution takes a lot longer than a lot of people think. But it’s, you know you mentioned Schumpeter earlier, creative destruction. Yep, it happens and it will continue to happen. And so my view is always just embrace it. And you with the newsletter, which is brilliant, you’re putting out really good material. I love the co-written thing. I think that’s a really genius idea actually. But you’re also using it as top of funnel for your venture activities. What are you excited about now in venture?
Packy McCormick
Oh my gosh. I mean kind of everything that I was just talking about and again I think the hardware thing and even complex businesses is a thing that’s gotten a little bit more attention over the past couple of years. But I think it was 2022, it was in the midst of all this bear stuff I realized like we’d invested in Replit, we’d spent a bunch of time in crypto where there’s composability. And I was like, man, it seems like it’s gonna be really hard to build enduring software businesses de novo now. And obviously there are exceptions to that rule in very big ways and certainly AI put in a different category but started getting really excited and I think I’ve always been really excited about this idea of just hard things that are really, really hard to do. And the manifestation of that now is these just complex vertically integrated businesses that are trying to compete directly with incumbents and just win categories of Anduril and SpaceX for everything we did along with Patrick actually Basepower Company, which is this battery company starting down in Texas, but will go everywhere and I think because there are a million things that go into why a company like that would be exciting. But I’ve spent a lot of time studying energy. I think the stuff happening on the generation side, on the nuclear side and the solar side is really exciting. On the usage side, the demand side, electric vehicles and drones and smart everything, all of that AI, certainly a big user of energy. All really exciting. If both of those continue to grow, the thing that you need is batteries. And if you want batteries, the best place to put them actually to balance the grid is next to the home. And if you want to be next to the home with a battery, the best place to start for a million different reasons is in Texas. And so finding the company that has the battery next to the home in Texas with the great people is what I dream of. We invested in this company that I wrote about, Somos Internet, that I think is probably the most similar business in the world to what Basepower Company is doing. They’re down in Colombia, they’re building what looks like, you know, regular ISP. And so half the investors who look at it are like, why in the world would I ever want to do an ISP? In Colombia they’re fully vertically integrated on a new architecture, building all of their own hardware pretty much at this point. In China they are doing active Ethernet with now they’re going to have two fibers directly into the home. So it’s almost like your home is a node in a data center. 10 gigabit Internet, for practically no money compared to what you’d be getting today, are laying their own national backbone, just this fully vertically integrated thing. But because of all of that, you can give this better experience to the consumer than they’re used to having. And you own one of three utilities into the home. I don’t think there’s going to be a water or gas company. So it’s essentially your power and your Internet are the two things that there can be a startup. And so if you own that real estate next to the home, the things that you can do both integrating up and down are just tremendous. And so I’m looking for these businesses that are doing a lot of really hard stuff. It took Somos five years to get to the spot that they’re at now where they’re just humming and really growing fast. But I think if that doesn’t become the largest telco in Latin America, at the very least something has gone horribly wrong because they have a product that’s better, faster and cheaper in a way that no incumbent is going to be able to hire the team to go out and do that. They have all this fiber that they’ve already laid that they’re not going to go want to rip up. They’re buying all of their equipment from Huawei and they don’t know how to do it themselves. If you look at it even in American telco, the R&D line item is like $0. They don’t do any of their own R&D. And that’s exactly who you want to compete with. And what I love about the opportunities right now is that I think for the first time in a while, instead of just saying we’re going to build software to help industries, people are saying oh cool, we have all this software, we have all this technology, let’s just build a better thing and go compete. And people think that’s possible and it’s starting to happen in a real way. So those are the types of things I’m excited about.
Jim O’Shaughnessy
On the venture side, do you look outside the United States? Because you’re mentioning obviously this is outside of the U.S. One of the things that we experimented with was a dedicated fund that we don’t run. So it’s. We’re an LP, but it’s in Bangladesh. Right. And literally the valuations there for an idea here that would be pre-money 100 million, it’s like 5. And what’s really cool is all the young people there are like a nation of entrepreneurs. And do you primarily, what’s your geography look like?
Packy McCormick
I do it mostly US. And then if there is a version of this business model, this vertical integrator business model that is happening that I think is the best version of that in their industry somewhere in the world, great. We did a mining company in Australia called Earth AI that’s doing really, really well and we did that in Colombia. Just personally just put a small early check in a drone delivery company in India. And so if the best version of a thing is happening somewhere else in the world, great. I think a lot of it happens in the United States, but if the best version of it’s happening elsewhere, I’m happy to do that.
Jim O’Shaughnessy
Yeah. And one of the things we’ve seen in Bangladesh is they just pore over ideas that start here, but they actually make them better because they’re doing the second iteration. The valuations are much lower. They can learn from the US startups’ mistakes. That’s a very interesting line for us. The other thing, what’s your view on all the startups? Because I have a pretty specific view that are wrappers of large language models.
Packy McCormick
I was very bearish. Back to the humility point. I think one of the things that continues to happen is you’re bearish. Then you get. There was one, it looked like a wrapper company. I’m not going to give specific valuations because we’ll give it away, but even 18 months I talked to the founder and I was like, what do you think about. I know this is, I’m a loser for asking this, but how do you think about over time building moats in this business? And he’s like, I build good products. And I was like, all right, well, it’s been good talking to you. 18 months later, it’s worth 33 times more than it was when I talked to him. So joke’s on me. And I don’t know if that’s a short term thing or a long term thing. I think each use case, I think each example, each situation ends up being probably a little bit different. I mean, Cursor. Now moving down into the models, I think is a really interesting company doing something really unique that people seem to love. Will they be worth 10x in 5 years? Potentially. Will they be worth 10 times less in 5 years? Potentially. I think the Anthropic OpenAI fight is even super interesting right now. As we were saying before, Claude has by far become my favorite model to use. I just think it’s moving so, so fast. I’ve largely, I have probably a fairly uninformed view because I’ve largely stayed away. I think there’s so many smart people fully focused on AI software and foundation models that I have no. I mean, I could write about companies and invest that way. And so there’s some edge. But there’s just so much to keep up with. And I’m so fascinated by this other part of the world that fewer people are fascinated by that. There’s some comparative advantage, at least that I have there. But I don’t know what’s your very specific view?
Jim O’Shaughnessy
My specific view is there’s an ur pattern there, a primitive there as well. And whenever a new technology really ignites the imagination of the society, hundreds of companies get started. So for example, at the turn of the 20th century, 1900, there was something like 200 car companies in America. One of them was actually an electric car company. And what happens is they try everything and then slowly the winner emerges. And the winner that emerges is not always the best product. Right. And so I think, you know the classic VHS beta.
Packy McCormick
Brian Arthur stuff, yeah.
Jim O’Shaughnessy
Yeah. I mean, but so I think that most of them are going to get nuked. Because very difficult to establish a moat. One of the things that we are working on in terms of commercializing some of the AI workflows that we’re doing and the actual AI itself, just really good picks and shovels. I’m not going to name what it is, but there’s a very common thing that everybody uses. Everybody uses. And our CTO has made that 50x better. I was talking to another friend of another portfolio company of ours and he’s like, do you realize how if you just sell this, just this thing alone, you’re gonna do incredibly well. So I do think that there is lots of room there. Yep. But wrappers.
Packy McCormick
I know. And then the fun part about what we do though is, I’ll sit. I have been sitting at wrappers. I will continue to sit at wrappers. And one thing that I pass on inevitably will have made up for all of the things that I got wrong. Probably if you had invested. I’m going to get the numbers wrong on this, but you might actually know. If you’d invested in Amazon at the peak of the dot-com bubble, I think you would have made up all of your losses. You know, I think I forget exactly. I’ve run this before, but there’s something like it. It outreturned all of the losses of the dot-com crash.
Jim O’Shaughnessy
Yeah, it’s actually true. I wrote a piece for which I was vilified in April of 1999 called The Internet Contrarian. And in it I said, the crash that is going to come is going to have 85% of these companies carried out feet first. DOA. But the example that I gave of a company that would probably survive was Amazon.
Packy McCormick
No way.
Jim O’Shaughnessy
Yeah.
Packy McCormick
And you bought too.
Jim O’Shaughnessy
Hang on. Because I had a thesis. I said Amazon will probably go on to do extraordinarily well, but first it’s going to go down 90%. It went down 93%. And then one of our models picked it up because we’re quants.
Packy McCormick
Right.
Jim O’Shaughnessy
So. But you know, it’s really interesting because that was the first time I experienced information cascades and homophily leading to homogeneity of views. And back in April of 1999, you were a heretic that was going to get burned at the stake for saying anything negative about dot-com companies. And I was like, I was 39 and the comments that I got on because it was a blog post for my company. The comments I got were like, you’re an old fogey. You’re only 39. You sound like you’re 95 years old. You don’t know what the fuck you’re talking about. And all that. In my journals, I wrote about it saying I have never experienced this uniformity of opinion. And it made me feel I’m right because literally when you have that kind of thing, and I made bad decisions because of that too. If you think that you’re not going to be affected by the just everyone thinking the same thing at the same time and the information cascades, you’re crazy.
Packy McCormick
How much of what’s happening now feels like that and how much is it different?
Jim O’Shaughnessy
It’s pretty different this time around. I think that there is still a lot of skepticism around it. We haven’t seen. Now we have on the investment side, but we haven’t seen. What was fueling a lot of that was the public loving the Internet. Wait a minute, I can buy any book I want on this website? Are you kidding me? Right? And so the novelty of that was different. I mean, because we’re all been so used to being online now. Listen, I think, you know, Jobs said computers were bicycles for the mind. I think AI is rocket ships for the mind. And but like anything else, it’s only going to be as good as the user, right? And the same power laws are going to apply. Don’t use a free version of one of the big large language models and ask it a stupid question and get a stupid answer and then say, oh, that sucks. Right? You need to come up that learning curve. But what’s interesting is it’s capping that incredible excitement that the general public had. I do not think that this is nearly the same kind of situation.
Packy McCormick
Were there more public Internet stocks than there are public AI? That has to be a big piece of this.
Jim O’Shaughnessy
Huge piece of it. The minute public markets are available to the public’s imagination and like Globe.com, the valuations of these companies when they went public and then they would go public at a ludicrous valuation and then triple after it. And I remember getting a call during this time period because you got to remember, and let’s be really clear, a lot of my success was being born at the right time, right? I was born in 1960. I was one of the first Gen X users of computers. If Ben Graham had access to my computers and the database, he would have written What Works on Wall Street, right? But the other thing that was super nice for me was I got married at 22 in 1982, and we began the longest decline in interest rates in 100 years. If interest rates are going down, stocks are going this way. Talk about a tailwind, right? And so, I was just incredibly lucky to be fascinated, really obsessed by the stock market at that time. So super lucky around that. Starting to feel. Because I experienced the crash of 1987. I fucked that up. I had a bunch of puts, and I let my emotions. That’s how I became a quant. I was always quantitatively oriented, but I had all these puts because I had a model, right? A quant model, and it said, bearish. And so I had amassed in my young life the largest put position I had ever had. And I let my emotion. Because most people don’t know before the real crash, there was a mini crash the day before. I was getting called by all the brokers who I was using, right? Because you called everyone back then and they’re like, dude, close your position. You just got back to even. You close your position because these are going to expire. And I was totally emotional about it. The model said, don’t close your position. I close my position. The next day, the market crashed. I would have made a fortune in all of those puts. And that was the push that was like, you know what? Maybe I’m the enemy here. Maybe my human OS. I’m no different than anyone else, right? I’m emotional. I get. I let emotions get to me. But then going in, it also tempered me, right? Because it’s like, okay, you might be able to see some signs that things are getting a little frothy. So I was a year early on the Internet call. The crash dot-com bomb didn’t happen until early 2000. But I got a call from the president of my company, who was in Arkansas in a McDonald’s, and he’s like, Jim, you know, all this stuff you’ve been gotten. You’ve gotten pretty bearish on a lot of stuff. And I went, yeah. And he goes, I think this is going to increase your bearishness. And I went, what? And he goes, I’m in a McDonald’s in Arkansas. There’s a bunch of people with their shotguns and hunting gear on, and CNBC is on the TV. And I’m like, oh, fuck. That was kind of the version of, you know, the shoeshine boy telling Joe Kennedy. But so I don’t see that as much, but I definitely see the adoption cycle is speeding up. Are you finding that as well?
Packy McCormick
Yes. Even in my personal usage, I’ve been almost proud of myself for how removed I’ve been. And I’m not going to invest in the app layer and I’ll be fine sleeping at night if I miss out on things that I don’t believe in the business case for. I think just even talking about my personal adoption curve went from using it a lot to over the break, I think a lot of people and in the past few weeks since Claude has gotten better using it all the time. And even now I’m like, shit, did I miss this whole thing? Was I wrong here? And so I’m just trying to be, you know, trying to be more conscious of those thoughts and emotions because that’s probably, you know, either a sign that this time is different for the first time and this is.
Jim O’Shaughnessy
The big one, most dangerous words in the market. This time it’s different.
Packy McCormick
Exactly. Or I’m starting to lean into that. And so I’m just, I really try to, I meditate daily now. I really want to actually watch my thoughts and understand if I’m getting swept up because I very clearly can. But it does seem like on the Internet, so there’s that echo chamber. And so it feels like the adoption cycle is faster. But even talking to my friends who are not, you know, part of tech, Twitter, people are using it all of the time and people are amazed and they want to talk about it. And so that is starting to happen. But then there’s no. Unless you want to be like, there’s a lot of people now who just become online. You talk to a lot of Uber drivers who are just online stock pickers now. And so unless you’re that level where you want to, you’re doing second order stuff and you’re buying nuclear because of. Or starting to buy quantum because of something that might happen.
Jim O’Shaughnessy
You’re right.
Packy McCormick
There’s not as easy an outlet for someone to get excited and be like, oh, there’s a fairly cheap thing that I can go buy and express my belief. And so that probably, yeah, it probably breaks that adoption total craziness.
Jim O’Shaughnessy
Yeah. The challenge with that is time horizons, right? We really do not want to turn the younger generation into hopped up. I want to double my money in a day because that usually leads to tragedy and despair. But by the same token, I love the idea that we’ve really democratized the tools that make it available. But again, it’s all how you can end up using it. If you’re going to end up using it like a slot machine, that’s going to lead to bad things if you’re not. The world is your oyster as a young investor right now. And things like. Again, back to context. I wish more people knew that Isaac Newton lost his entire fortune in an Internet AI company of the day. But it was a South Sea trading company. The graphs are identical. You plot the South Sea, right? And you plot the NASDAQ. They’re identical. And that’s not because they’re completely different industry, completely different thing. It’s because of us.
Packy McCormick
My takeaway from that Jim Simons book was essentially that his machines were just really good at understanding when humans were being irrational and just trading against us when we’re irrational.
Jim O’Shaughnessy
And that’s basically what my thesis was too. It was basically technology, innovation, industry change minute by minute. Markets change minute by minute. Human OS, millennia by millennia doesn’t budge a bit. So arbitraging human nature is the most sustainable edge. And it works for public markets super well. But it also works in private markets, right? What do you ever see? Because you must see huge deal flow now what are the ones? And don’t name any companies please. But just give me categories or pitches just you’re just like. Yep, nope. Goes right into the circular filing.
Packy McCormick
I have to confess something that if current or future LPs are listening. Sorry, I do a lot more subject line straight to the trash. I really am trying to be more, just more thoughtful about what I even take into the top of funnel. And I’ll be super happy if I invest in five companies this year and they’re things that I love. I don’t have a thesis because if the fusion company that I invested in when I thought fusion was a completely uninvestable category, if I had studied for the rest of my life, I never would have come up with the idea that he had come up with that makes it feel more investable. So I’m not thesis driven in that way. But there’s just I have a tighter box now and so there’s a lot of small ideas that go right into the trash. That’s obvious. Anything that’s not differentiated for me goes right into the trash. Differentiated, short term, structurally different, built in a way to maintain that differentiation over time. So there’s not a particular category. There’s nothing even for me to pick on in particular. I think people are trying a lot of really interesting things and we will see what works. I have not made a robotics investment yet, although I think there’s a lot of single use case stuff that’s really interesting. But really for me, it’s, is this thing something that not 12 other people are building and I just don’t have the time of day to pick the best of the 15 entrepreneurs going after the same thing when there’s so many other really big opportunities out there. Yeah, I don’t know. It’s a pretty boring answer, but it’s just my top of funnel used to be like this.
Jim O’Shaughnessy
Your entire brand is not boring.
Packy McCormick
I know. I used to take. It must have been 20 pitches a week in the beginning and now it’s four or five.
Jim O’Shaughnessy
Right.
Packy McCormick
It just. I really want to tighten all of that.
Jim O’Shaughnessy
And let’s flip it around. What innovative business models are you seeing that you’re like, wow, okay, this is really, really intriguing?
Packy McCormick
Man. I’m going super off brand here and I’m going to come up with boring ones again.
Jim O’Shaughnessy
You know what? I think I’ve got now the title for the podcast Boring.
Packy McCormick
I don’t know. I mean, there’s a lot of interesting stuff that’s going to happen. How do you pay for workers as opposed to, you know, for seats or all the different AI stuff I think is super interesting. I think the interesting business model to me is whatever works best for the industry that it’s in. A way that’s kind of, I’m bad at doing these answers because it’s so use case specific. I think I mentioned that company Earth AI and so to go back to them a little bit, they started out building, you know, back in 2018. So pre-AI started building AI models to do mineral discovery in Australia where a Y Combinator company they sold to explorers and they could actually make themselves because explorers will raise some cash and then they’ll be willing to spend it and then they disappear.
Jim O’Shaughnessy
Right.
Packy McCormick
You’ll get a $50,000 contract selling them this thing. Either they go under or you just never hear from them again because they’ve either found something they haven’t. So you can’t train your model on that. You have no idea if your business is doing well. And so finally the guy was like, you know what? I’m going to go out, I’m going to build my own drilling rig. And I’m going to go out into the field, I’m going to actually see if this thing works. I’m just going to build one and I’m going to see if we’re actually coming close to anything. We’ll go with. We will tell our explorer customers that we will go with you and dig the hole for you, drill the hole for you, just to know if we’re actually finding something or not. And so he did that and then they decided to build their own rigs and now they’re just, you know what? And I think this is true in most of these categories and these vertically integrated things where you start out selling software, you sell to a customer that is a really bad customer. And if someone’s a bad customer, that they’re probably a pretty good competitor to have. And so they started just competing. Now they make their own drilling rigs. They’ve made three discoveries with potentially a fourth. And I bring all of this up because the business model here is essentially where in Australia, where they’re starting, if you can find something that’s not brownfield, which means not next to an existing site or something that people have done before, if you can actually find greenfield discoveries and no one’s been there but you plant your flag that is yours in perpetuity. So you find that you have a cheaper drilling rig, you go out to the spot, you drill it’s yours, and then you develop it a little bit. And if you can drill cheaper and faster, then you can develop it faster. Sell a stake in that business. The drilling rigs are not particularly expensive, but you sell a stake in that deposit to a miner, to somebody midstream, and then you take that cash and you buy more drilling rigs and you work down this 650 target list in Australia and that just spins in this unbelievably beautiful way. Literally the first time that you sell a stake in a deposit, you can just spin this machine that keeps going forever and ever as long as people need metals and minerals, which I think we will for a while. And so that’s not a trend that I’m seeing in the market. But that is something that in that particular use case, and I actually said no to it at first because I’m not going to invest in the Ukrainian guy who started up a mining company in Australia. But we’d been doing Elliot, who I mentioned earlier, and I were doing some biotech investing and I was like, this actually feels like what the biotech platform business model is where you use technology to develop an asset and then sell it off and then take that and invest in more. But it’s that with perpetual rights on the deposit that you’re finding. And so all of what I do is trying to find these one-off things and by building this top of funnel, that’s what I’m looking for. Are these really one-off things that specifically work for the industry that they’re trying to beat?
Jim O’Shaughnessy
Yeah. Our first really big client at my first company, O’Shaughnessy Capital Management, had done extraordinarily well in mining and gold mining. And he was a wonderful man and gave me my time horizon. I was sitting with him out west. There were pictures of all of his grandkids on the table next to where we were sitting. I had. Because he was elderly at the time, and so I had brought these really conservative portfolios, right? And he’s looking at him, he’s this, you know, cowboy to the boots, right? Weathered face, loved this man. Anyway. And he goes, what you bring me this shit for? And I’m like, well, I mean, given your age. And he looked at me and he goes, you don’t get it. You don’t get it. And he points at his grandkids, he goes, my time horizon is infinite. And I loved that. And it changed my own thinking because that’s the answer I give now. Because I have grandchildren, I hope to have great grandchildren, I have organizations that I would like to continue to support, et cetera. And what that does is almost like a magic spell. My time horizon is infinite, meaning you will make decisions in a completely different manner. But the reason I bring him up was he also, gold miners in general are the biggest risk junkies that I have ever met in my life. And he told me this really funny joke. He’s like, he also was a pilot and that’s how he actually found. He trained his eye to see certain impressions that meant there’s gold in them hills. Anyway, so we’re in the plane and we’re on the thing and he’s showing me all the stuff that he sold to this big company. And he goes, did you hear about the miner who died and went up to heaven? And I went, no, tell me about him. He goes, well, yeah, he got up there to heaven and St. Peter came out and said, I’m sorry, this is really unusual, but we’re full up with miners. You know, we got a quota, we normally don’t ever get many of them up here because you guys are so crazy. But all these are wonderful guys and they’re in heaven. And miner goes, so you’re telling me. He goes, you got to go to the other place. He goes, but I’ve led a great life. And he goes, listen, I’ll make you a deal. They’re all over there because they love hanging out together. You can go over there and say something to him and if anyone leaves, then we’ll open a slot for you. And the guy goes, okay. He goes over and shouts to the other miners, gold found in hell. And they all dash for the elevator to go down to hell and St. Peter goes, that’s brilliant. Welcome. And he goes, and then St. Peter goes, because he’s walking away. And he goes, what are you doing? And he goes, I’m joining those guys. There might be something to that rumor. So.
Packy McCormick
Yep.
Jim O’Shaughnessy
I mean it is a super high risk, you know. And the other joke he told me was what do you call most gold mines? A dark hole with a liar at the other end. But if you can figure out a way to innovate like you’ve just described, potentially.
Packy McCormick
And what you want I think is none of the explorers have the resources to go out and do 12 of them, but if you have a portfolio, actually you’re in a pretty good spot. And so that’s the innovation on this one.
Jim O’Shaughnessy
So. And let’s go back to writing. What are you most excited about? Do you plan out what you’re going to be presenting or does it just grab you and then you go with that?
Packy McCormick
Yeah. So now actually a little bit more now that I’m doing these co-written essays with people. So I have to have some sort of a content calendar just because I’m working with other people on it. The thing that is most exciting me about those is that I would not have predicted the ideas that particular people would have given their industry. You have to get through layer one and get through the pitch idea. And then you talk for a while and you’re like, nope, that is the thing that we should be writing about. And that just keeps happening over and over again. So I’m really excited for the, that this year, probably the category that I want to explore the most that I haven’t done yet and that I just need to take the time to go do I think bioelectricity, all the Michael Levin work is the most fascinating thing in the world and my very dumb take on it. I wrote that electric stack piece. And if we’re in this electric era, I bet just cosmically that the body is going to turn out to be more electric and more electrically controllable than previously thought. But the results that they’re getting.
Jim O’Shaughnessy
Doesn’t the heart have its own generate its own electrical field? I think that it does.
Packy McCormick
That sounds right to me.
Jim O’Shaughnessy
But everyone listening, I will look that up after we’re done.
Packy McCormick
Yeah, but I mean the whole body is just more electrical.
Jim O’Shaughnessy
I Sing the Body Electric.
Packy McCormick
I Sing the Body Electric. I went back and the book was terribly written, but really interesting.
Jim O’Shaughnessy
Great title.
Packy McCormick
But you could regrow amphibian legs by applying. Just by putting a cuff around it and applying the right current to it. And I think there’s just a lot there.
Jim O’Shaughnessy
Well, you know, Maxwell is a great example of a guy who I don’t think gets enough credit. His work spawned more innovation than almost any other one from that period. And right now a lot of people say Maxwell who? Right.
Packy McCormick
We have, we have a piece coming up that is Maxwell adjacent. A piece with a quantum magneticist. So I’m not the one who’s actually going to be writing that, but talking about why humans are so bad at grokking.
Jim O’Shaughnessy
And is that the strategy going forward for the paid is are they all going to be co-written or are you going to sometimes do solos?
Packy McCormick
I think it’ll be a... I think free. I want to keep the big tentpole pieces just out there, but there might be ones like that piece that I was saying I wrote about my son selling stuff. That’s probably…
Jim O’Shaughnessy
That’s cool.
Packy McCormick
Yeah, that probably stays. I want to have a spot actually where I can feel free to write more short stuff that I don’t feel like I’m spamming 257,000 people with. I’m only spamming the people who’ve been nice enough to pay me. So thank you and sorry in advance, but that’s the spot where I want to just experiment a lot more.
Jim O’Shaughnessy
And is that going forward? Is that going to be the twin engines going to be the paid, always keeping the free and using both as top of funnel for the venture. Any plans to raise another fund or. Yeah. Okay. And you can’t talk about it.
Packy McCormick
Incredibly excited about that opportunity set that we’re talking about right now. And I’ve been surprised. I think in the beginning, my thesis on the original fund was maybe if I have this newsletter, people will let me write about them and then they’ll let me invest. And that was. More people read it than I thought and were just like, oh, yeah, you write a small check and we read Not Boring. So come on in. I think now the way that I’m thinking about it is I want to be the best in the world at this one thing, which is telling stories about these companies and then everything that goes around that it can’t just all be company stories, but I want to be the best in the world at that one thing. And I think, particularly for the type of business that I’m interested in, but for companies generally, you see a lot of companies out there hiring chief storytellers or narrative officers or whatever. I think I can do that, but then apply, add distribution to it. Add just the fact that the audience likes to come to Not Boring to read these really deep, long things that we’ve been told that people don’t read anymore. So I think this combination of investing in this type of company and writing just is way more fun than I thought and way cooler than I thought. So either am or we’ll be raising against that thesis soon.
Jim O’Shaughnessy
Cool. That kind of brings me full circle to the original. Your idea that I never got an actionable idea from a podcast. I think that you’re gonna see this type. And of course, obviously I’m reasoning based on my priors, let’s be very clear. But the kind where a conversation. It’s more of a freewheeling conversation, but then the people who are listening or watching can go to a piece of writing that you mentioned. Right. And that’s where the idea discovery comes. They get it by listening to it. But there needs to be a next step. And I think that type of podcast is going to continue to do really well.
Packy McCormick
Totally. I think I put it in the piece, but I think that podcasts are unbelievably good for getting to know people. This type of conversation where we’re just sitting here and talking about a bunch of different things. This would be the weirdest essay, you know, the weirdest written thing of all time. Nobody would sit through this whole. Maybe you said that you read transcripts sometimes. It’s not the kind of thing that you’d want to ever read because there’s this back and forth. There’s our faces, there’s all of that. But any idea that I’ve said on this, at least me personally, I would do a much better job expressing that idea in writing. And I think a lot of people, given the time and a week to work on something or a month to work on something, will do a much better job expressing that idea. And then to your point, once they have it, then you can go out and just repeat it over and over.
Jim O’Shaughnessy
And it’s the conversation that introduces them to the concept. And so I’m still very bullish on that and I think that will continue. But I’m also completely agree with your thesis that you got to get it in writing. Right. Because if you don’t have it in writing, you haven’t really thought about it because writing is thinking. And you know, these kinds of things can be great and lead you to all of those cool pieces. But you probably. Because again, imagine if we were going to talk the way we write, then you’d get really fucking boring.
Packy McCormick
Yes, 100%. That doesn’t work. Writing has just been so oversold and video is great and podcasts are great. And part of this is just, this could be me. I’m about to be 39, so maybe this is me being old. But writing doesn’t feel like something that’s going to go away. And so I think it’s really oversold. And I’m, you know, I think having just announced this to the world, the amount of people that are like, yeah, I actually do want to come on and write my thing.
Jim O’Shaughnessy
Yeah.
Packy McCormick
Has really blown me away. So I think writing is coming back.
Jim O’Shaughnessy
Yeah. As investors call it a deep value opportunity. Because I agree with you, it’s not going away. And in fact, I think quite the opposite. I think that the people, if I was giving advice to a young person today, I would say learn how to write really well. And because not only is it going to improve your ideas because writing is thinking, but everyone else is doing TikTok. Go the other way and you’re probably going to end up really well. Well, Packy, this has been, as I anticipated, super fun. I love talking to you because I love your optimism. I remember when I first saw you, I’m like, oh, finally. Finally we have a young person out there saying, not the sky is falling and oh, woe is me. But look at all these great things that are going on in the world. As you might remember, even though it was a long time ago. Our final question is, we’re going to make you the emperor of the world. You cannot kill anyone. You cannot put anyone in a re-education camp, but we are going to hand you a magical microphone and you can say two things into it. And the two things that you say into it are going to incept the entire population of the world. They’re going to wake up whenever their next morning is and they’re going to say, you know, unlike all the other times when I woke up with a great idea, I got two this time. And I’m actually going to start acting on them right now. What two things are you going to incept into the world?
Packy McCormick
Be you. I think that’s a big one. That’s my goal for the year, probably the rest of my life. And I don’t know. Be joyful and energetic. I’m giving advice to myself now, but these are the things that I’m telling myself, we’re so lucky to be in the situation that we’re in right now. And so I think one, there’s just differentiation and just being unique and interesting and authentic to who you are. I think you have to learn as you get older that is the most important thing. But I’m really also just trying to be as joyful and energetic as I can because the world just becomes more fun that way.
Jim O’Shaughnessy
Oh, totally.
Packy McCormick
And you’re the prime example of this. But the world just becomes. As soon as you’re like, hey, I’m gonna experience whatever happens with joy, it just gets joyful. It’s wonderful. So those are the two things.
Jim O’Shaughnessy
I love both of them. I’m reminded of Oscar Wilde’s be yourself. Everyone else is taken. But I also like the idea of authenticity is just you. I see so much advice online, right? Be authentic. In other words, be a fake and ape this person over here.
Packy McCormick
Here’s how you talk authentically.
Jim O’Shaughnessy
Exactly. This has been a blast. We’ll have all of your info on the show notes and can’t wait till next time.
Packy McCormick
This is so much fun. I can’t wait.
Jim O’Shaughnessy
Thanks.
