The Daily Stoic - How High Risk-Takers Are Shaping Our World | Nate Silver

Episode Date: September 11, 2024

Nate Silver is an American statistician, poker player, and New York Times bestselling author of The Signal and the Noise: Why So Many Predictions Fail -- but Some Don't . Nate’s latest book is On The Edge: The Art of Risking Everything, where he dives into the worlds of Doyle Brunson, Peter Thiel, Sam Bankman-Fried, Sam Altman, and more. These professional high risk-takers fall into the group that Nate describes as “The River”, a community of people that have increasing amounts of wealth and power in our society.Nate came to the Daily Stoic studio to talk with Ryan about incentives in large media corporations with independent media, ethical challenges of audience capture, financial motives in journalism, conflicts between truth-seeking and profitability, the dynamics of tech versus traditional media, effective altruism, and much more. Nate is the founder of FiveThirtyEight and the New York Times bestselling author of The Signal and The Noise. 📚 Grab a signed copy of On The Edge: The Art of Risking Everything by Nate Silver| https://www.thepaintedporch.com/Subscribe to Nate Silver’s Substack: Silver BulletinConnect with Nate Silver on X: @NateSilver538🎟 Ryan Holiday is going on tour! Grab tickets for London, Rotterdam, Dublin, Vancouver, and Toronto at ryanholiday.net/tour✉️ Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail🏛 Get Stoic inspired books, medallions, and prints to remember these lessons at the Daily Stoic Store: https://store.dailystoic.com/📱 Follow us:  Instagram, Twitter, YouTube, TikTok, and FacebookSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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Welcome to the Daily Stoic Podcast, where each weekday we bring you a meditation inspired by the ancient Stoics, a short passage of ancient wisdom designed to help you find strength and insight here in everyday life. And on Wednesdays we talk to some of our fellow students of ancient philosophy, well-known and obscure, fascinating, and powerful. With them we discuss the strategies and habits that have helped them become who they are, and also to find peace and wisdom in their actual lives. But first, we've got a quick message from one of our sponsors. Hey, it's Ryan. Welcome to another episode of the Daily Stoic podcast.

It's funny, I'm working on the wisdom book now, and I had this chapter that I wanted to do on risk, just like how does a wise person understand and relate to risk? It's interesting, right? All the cardinal virtues are so interrelated. Obviously the courage book is about when you defy the odds, when you take that gamble, when you put yourself out there. And yet wisdom is also sometimes rendered as prudence, right? So not taking unnecessary risks,

knowing the dangers, almost kind of a cautiousness. But the reality is that life is inherently risky. I was just thinking about this as I was preparing for today's guest. There's a chapter about bravery in stillness is the key that I went. So it was like a specific person that I wanted to talk to them about. It's like the second to last chapter in Stillness. And I'm talking about this French philosopher. I wanted you to tell you her story

because she's like amazing. I talk about the main character in Camus, the fall, and I contrast him to a French philosopher, Anne Dufour-Montel. I say, who died in 2017, age 53, rushing into the surf to save two drowning children who were not her own. In her writing, Anne had spoken often of risk,

saying that it was impossible to live life without risk and that in fact life is risk. It is in the presence of danger, she once said in an interview that we are gifted with the strong incentive for action, dedication, and surpassing oneself. And when on a beach in San Tropez she was faced with a moment of danger and risk, an opportunity to turn away or do good, she committed the full measure of devotion to her ordeals. What is better, to live as a coward or to die as a hero, to fall woefully short of what you know, to be right or coward or to die as a hero, to fall woefully short of what you know,

to be right or to fall in the line of duty? And which is more natural, to refuse a call from your fellow humans or to dive in bravely and help them when they need you? Obviously, not all risk is so existential. A lot of it is much more statistical, which is the subject of today's interview. And I'll connect this to another writing of mine,

not because I'm just trying to promote my own stuff, because I really want you to read Nate Silver's new book, On the Edge, The Art of Risking Everything, because it's incredible. I took a bunch of notes, I really, really liked it. And I'm somewhat related to the book, because he had reached out to me. I wrote a book a number of years ago called Conspiracy,

which is about this billionaire Peter Thiel and his sort of secret daring gamble to go after this media company. And I sort of use it as an excuse to explore the idea of strategy and risk and contrarian thinking and doing what people don't expect. It's not like any of my other books, but it's a book I'm very proud of. They're actually making it into a movie.

And Peter Thiel is the main subject of that book. Also this guy, Nick Denton, is a main subject of the book. And Nate knew Nick, but didn't know Peter. And after the book came out, he had reached out to me and asked if I might introduce him to Peter Thiel, who is one of the most fascinating subjects of Silver's new book, as I was saying, On the Edge. So look, this kind of a rambling introduction, I understand, and I'm sure my editor will have cleaned up some of it

by the time you get to it. These are all things that I have been thinking a lot about. Like I literally have this stack of note cards here on my desk. Life is risk, I wrote. There is one in every decision. There is risks to questioning, right? To curiosity, right?

It kills the cat ultimately. There is no learning without risk. I wrote, it killed the cat again. So clearly I wanted to do that. The point is, I've been thinking a lot about the themes of this book, so I was very excited to have it. And then when I finished this discussion, I said to our producer, Claire,

I wanna have more conversations like this on the podcast. So I hope you really like listening to it. I took a risk. I was supposed to be out of town to go do something. And I decided to stay because I thought this interview was worth doing in person. And Nate's flight was delayed, but he ultimately ended up coming.

And I think we had an awesome conversation and we got a bunch of shared people we know in common, so I think this interview is really interesting. And then as it happens, my wife found out the next week that he had left our interview and then went and had dinner with a woman she's friends with and her husband. So small world, great interview. His new book, On the Edge, The Art of Risking Everything is incredible.

His book, The Signal and the Noise, it's also great. You might be familiar with Nate's work at FiveThirtyEight, which has been an incredible predictor of presidential elections. He has a substack. We talk a lot about substacks and audience capture in the interview. You can check that out.

It's called Silver Bulletin. And I'll leave you now with me and Nate Silver talking about risk. ["Silver Bulletin"] Are you technically sort of of the village because you're in media? But what if you're a media entrepreneur and then you're taking a certain amount of risk and there's a difference there? I mean, one is that like, before I got into the media, I played poker for a living and stuff like that, right?

But yeah, if you have a more entrepreneurial vent and kind of like, I think it's a big advantage. I think like on Substack, you find ways to like, it's not game the system, but just like, you know, you have some understanding of what the value of your time is and what tends to move the numbers and what doesn't, right? You're not insulated from the economics of what you do. Yeah. By definition, you are as an employee.

Yeah, you know, for years, I was employed by one of the world's largest media companies, the Walt Disney Company, and no incentive-based compensation whatsoever. And so it's like, okay, if I go and play in a poker tournament, which is something that I love to do, then it's kind of free, right? It's like basically you're kind of burning time

on the clock now, right? And like this year I was at the World Series of Poker, we had launched the newsletter, and there's all this news, right? It's like, oh, Trump just got convicted of all these felonies, right? And I'm playing in a $1,000 buy-in tournament. And I'm like, if I write a post right now, the expected value of that is like a lot greater than $1,000, right?

So should I just punt the tournament? And probably you should. Although you also get in a situation where like, I think people need constraints. And like when you have a thing where you can kind of like publish a post and make, I'm not gonna say how much, but there's certain topics where you can't drive yourself crazy and what are you really maximizing for, I guess. But it's very different. Well, especially, I would say, for people who are trying

to think about how the sausage is made journalistically, if you're a journalist and there's always been somewhat of a ceiling on what you can make, and journalists are upper middle class if you are successful at it. And then suddenly the economics of being your own media company where you are selling directly to consumers, suddenly it's like lots of money,

potentially could be lots of money. And that can be a very wicked set of incentives operating on someone who's never, what they write or think has never been influenced by how much it will or won't make them. And that's where obviously audience capture and stuff like that comes in. Yeah, I mean, there's kind of a short run and long run,

right? I mean, like, two days ago, I wrote a post that was very critical of Joe Biden, right? And even though there's no news value exactly, I mean, I think there's historical value in putting his stubbornness about dropping out in Biden, right? And even though, you know, there's no news value exactly. I mean, I think there's historical value in putting his stubbornness about dropping out in perspective, right? But like, that's just, you know, a post that like,

it got lots of page views. It did not convert very well to subscribers, relatively speaking. And it probably, I know I've got like a lot of Kamala friendly audience because she's been rising in the forecast. But like in the long run, like people are paying me in many cases for my, you know, uncorrelated takes and for my independent takes and like

you're going to get what you're going to get. And I think that's really important. The trick is like, I don't like politics, right? I like elections. I think election forecasting is an interesting problem and that like it's a little gamified and that part's fascinating. But I don't care about like the state of the union address. I have as a citizen policy preferences, I have an economics degree, but like I'm not like, I'm't care about like the State of the Union address. I have as a citizen policy preferences, I have an economics degree, but like I'm not like I'm not concerned about like congressional procedure, for example, or things like that or obscure special elections. I don't have any national implication.

So yeah, I'm just not going to write about it, right? I mean, you know, and then you also hit this thing where if you have like a newsletter, you either kind of just you're the brand or it's like a brand like in the sub-stack ecosystem like the Free Press or something, right? either kind of just you're the brand or it's like a brand like in the sub-stack ecosystem, like the free press or something, right? Where now all of a sudden it's like 35 people and is there any in between there that kind of works? I mean, you can hire people to help you,

but like you're your own brand, right? And you can do some degree of expansion, but if you stray too far, then it undermines that, it undermines the quality a little bit, I think. And because you're a kind of man of the quality a little bit, I think. And because you're a kind of man of contradictions in some ways, and I am too, right? What are my contradictions? So I don't know that much about all the stoicism stuff.

I was trying to bone up on it, but then I had all this political news, so I didn't really get to, yeah. Because on the one hand, there's a stoic side, but you're also a terrific entrepreneur, right? That's a little, I mean, maybe on some deeper vector, it all makes sense, right? But on the surface, a little bit of tension, I suppose, right? Like it's a little, I mean, maybe on some deeper vector, it all makes sense, right? But on the surface, a little bit of tension, I suppose, right? I guess, I mean, that's the same as this sort of journalistic tension where it's like, I care about truth and information and reporting,

but if it's not actionable to someone, no one would pay for it. So I think there's always that tension. I think it's interesting too, because yeah, sometimes I get that about the entrepreneurial side. And then I go like, but what about the bargains to speak of the village that you talk a lot about

in the book? Like I'm not charging undergraduates $40,000 a year. Do you know what I mean? Is that somehow more ethical or less? That creates its own set of incentives, which arguably first have moral implications and then incentives. And I'm not sure they're any better,

but sometimes we're just used to those incentives. So they kind of operate in the background. And then when something new comes up, then we're like questioning all parts of it, even though it might actually be pure and get a better outcome. Yeah, look, I think in the long run, it converges more than in the short run sometimes. It maybe doesn't, you know, in my career, I've always done stuff that I loved and that

I worked really hard at and I thought added value and was differentiated and, you know, you're getting something you can't get anywhere else. And like, there's no tricks involved. But at the same time, if like, you know, post A is going to make me, you know, 2X post B and I'm otherwise indifferent or mostly indifferent. Or if I'm gonna flight from Seattle to Austin, I can be like, I could go and like relax and have a beer

and listen to your podcast and things like that. Or I could like write an important post on Kamala Harris and her convention speech, then that affects the incentives quite a bit. But can you turn that off? So like, when you think like I'm writing this or that, are you thinking like, this is its expected return or this is the expected value?

Because obviously that's partly how your mind works. I feel like I've had to work pretty hard at not thinking about that at all. Like so I don't check stats on most things. I don't look at the replies of the, I wanna have an audience rather than an audience have me. Yeah, I think I'm in a phase where the newsletter is still relatively new.

I mean, the paid product's been up for less than a year. So I think it's still pretty informative to have a sense for what works better than what doesn't, but it's often hard to predict. Like I did a post a month ago that was just seven quick thoughts about the Kamala Harris slash Trump polling, right? And it was like, I don't think it's quite dashed off.

I mean, explain in a minute, right? But it took 45 minutes to actually write. I write very fast and like, that got some like insane number of signups. I don't know quite why. Maybe the timing of it just hit right. And sometimes these more informal headlines convey more honesty and like authenticity.

The other thing is like, I'm always processing stuff in the background. If you're a writer, then if you go, I did a speaking gig in San Francisco, right? And sometimes on these book tours, they don't really bother to like feed you very well, right? So I went out and got like some late night tacos and had a beer, right? And I'm like, you know, but I'm thinking about like articles for the next five days and like processing stuff. So you're not like really off the clock with creative content, I don't think. And so you're trying to like, I call it like nose to tail blogging, where like, if you've

put X amount of effort into thinking about something, even if it's something that's not necessarily in your venue, you're thinking about like, you know, why is a certain sport popular in a certain part of the country and you get really into this problem and things like that. And then, like, I think she kind of used those and not let defer that you've made go to waste, you know? Yeah, or metrics decide that it's not worth doing. Right, yeah.

I try to avoid having throwaway posts in an email newsletter. Because people will stop opening? People will, and we really, we have like insanely, we have 60% open rates still, which is kind of insane. No, because like you're pushing into someone else's space. And I don't want to have an email that like, I mean, if there's three things, it's like,

oh, here's a link to a cool interview I did with Ryan, right? And here's a book tour event coming up and here's a little gimmick or something, right? Or a cool book I read. You have to respect the access that you have. Yeah. I mean, cause you're, you know, it's not, it's very different than pure web publishing. I mean, we're kind of a hybrid, like basically half our traffic is from the web and some people use like a traditional website, but I want to respect the email list. Yeah, I think about that. Although when I was thinking that when you talk about decoupling in the book and one of the things I, one version of sort of accidental decoupling for me is like you

learn, you do it long enough. The thing you think is going to do amazing does terrible. Yeah. And then the thing that you don't think is going gonna do well does amazing. And you sort of, you kind of learn to decouple like sometimes your own intuition from what you do or don't do, or you learn maybe just to actually trust the intuition and ignore the data because more often than not, you're right.

So it's like, as you said, short term versus long term sort of evaluations of things. The thing that really took the product off was actually not politics stuff, but the NCAA basketball model. And it was a Sunday. I didn't have too busy a day. But I'm like, I bet if I spent all day on this, I could get the NCAA basketball model revived.

But is it worth it? It'd be really nice to have a mental day off. I just did finish the book. And then you do it. And then by the time I'm going down my driveway, you're like adding like dozens of, it's just kind of crazy. And I had no idea that there was that much demand for it

until you do it and you experiment. Well, I thought that Peter Tilstuff was fascinating in the book, and I think you asked me for his email. Am I, is that- You did, I was gonna, yeah, I wasn't sure if it was, and that was actually like a door opening interview for me, right? In the original proposal for the book, there was a lot more about Wall Street.

I mean, I'm based in New York and I thought like, oh, a hedge fund or something is like a more direct analogy as you're like moving out of like poker and sports betting and things like that. But, you know, the VCs were interested in talking to me and they're interesting people. Right. I mean, they're they're more, you know, multifaceted than the hedge fund guys. And the hedge fund guys are like, I have hedge fund friends, right? But they're a little bit more, I don't know, somewhere on the spectrum sometimes.

And also they're guarded because they understand that they're a finite number of $20 bills lying on the street and they don't want someone else to pick them up. Whereas VCs kind of want some degree of contagion for their ideas. Yeah, the Wall Street guys seem to be like, this is how to make the numbers go up or like it's a math oriented thing with with the VC ones that I've met. It's a philosophical right approach to it as much as it's a data driven financial.

Yeah, I mean, I think I, you know, I don't think they are particularly materialistic exactly. You know, you go to, you know, rich people's homes in Silicon Valley and they're kind of low key and understated. It's not Hollywood, it's not a penthouse apartment in Central Park, New York or something like that. You know, I mean, ironically, I think they're kind of irrational on some level, right?

If you have basically reached a point where you have infinite money and you keep competing, you're doing it for the love of the game is a maybe more charitable way to put it or because something in your DNA or your upbringing causes you to have this intrinsic property to like always battle, always battle, always battle. Yeah. Yeah, that's what it's like Peter's thing. I watched this interview with Seinfeld once and he was saying that like a comedian is like a wood chuck,

like you don't know why the chuck would, they just do it. And it's like, you just have this thing that you can't turn off. And he strikes me as like a theorizing machine. Like he can't not come up with theories about why things are the way that they are. And then he happens to have joined that with investing in said theories. Like Eric Weinstein, who was much more of a sane figure when he told me this, said that he thinks Peter Thiel is the world's

richest applied philosopher. And I was like, oh yeah, that kind of, I think that's also kind of how he sees himself. You look, I think one of the ways in which people are lucky is that you come along at times and like Certain skill sets happen to be like really rewarded right and like you know on a much smaller scale than Peter Thiel I have this weird overlap of skills that in the exact way the media industry is working with these newsletters in 2024 Plus you have a book coming out which was supposed to come out a year and a half ago, right? Oh, we wouldn't intend to have this whole cluster bomb approach newsletters in 2024. Plus you have a book coming out which was supposed to come out a year and a half ago, right? We wouldn't intend to have this whole cluster bomb approach

where like the podcast and the book and the newsletter like all launch at once. It was supposed to be like staggered so I could transition out of politics. But then you have this election, turns out to be really interesting, right? It was gonna be deathly boring. Biden versus Trump and every poll is plus one Trump

or plus one Biden for months. Then you have this much more dynamic campaign. But if something like that happens, you have to be like, this is very much being in the right place at the right time, several times over really. But Peter Thiel doesn't believe in luck, only cause and effect.

Yeah, maybe I do think it's, I think maybe it's in some ways, he's a little bit more at peace with himself. Because if you are like, Elon Musk or any like reasonably successful VC, and you're like, I am in the 0.0001%. I mean, one of the 20 richest people out of the 80 billion people that ever lived, it gets a little bit weird, right? You're like, how am I so the center of my own narrative as much? And especially if you're like a little bit, if you are independent minded and you have this kind of great life,

then like, I think it gets a little weird. And you maybe start having to ask some like, from like a, from like a basic, like if I won the World Series of Poker, if I finished fifth or something, then that would be normal. It wouldn't change you that much. But if I won, I'd be like, is this really happening?

You know what I mean? It would be like a little, a little bit weird. It would be, you know, and you wonder, is this like, is there some type of simulation, or is there some type of intervention? Right? I mean, I think as a Bayesian, you

start to have to ask questions like those a little bit. Yeah, but I would wonder if the explanation's a bit more simple. So you have some theories about the universe. They make you billions of dollars. Because they were interesting, or you made for a couple of good interviews, they make you billions of dollars because they were interesting or you made for a couple of good interviews, you also develop kind of a public following

or you sought out a public following. Like there's plenty of VCs that are incredibly successful and nobody knows their names. For sure. And they don't tweet a lot and they don't want an audience. But so you already have the proclivity of sort of wanting the recognition. You need to be the smartest guy in the room. And now you're basically only

hearing from people that want something from you, or are attracted to because they think you're brilliant. And so like, I, I, and then and then let's add on top of this, the toxicity that is the sort of Twitter algorithm. If what you do is like, spew out theories and that's what they do, they're like, well, what about this? Maybe this is going to happen. Here's where the future is going.

And early on, people would say that's crazy or that's what about this? And what it more and more you're only hearing from people that say that's brilliant. I think those theories are going to get weirder and weirder. Because I've gone through different like epicycles of this, right? Where like your status like waxes and wanes and like for me to have like a lot of longevity. And yeah, absolutely.

You kind of like right now I'm in like an upcycle and you know, have more opportunities than ever. And now it's relatively new again, and it feels good. But I'm very afraid that, because there are guys that just kind of get lost in their rich person shit, right? Where they're never gonna have any real criticism. If they do, they have infinite optionality

to move on to something else, right? And there's kind of no touching grass and no reality check. And how do you avoid that? I mean, believe me, there's kind of no touching grass and like no reality check. And like, how do you avoid that? I mean, believe me, it's like the better problem to have than in the way around, right? But if you see yourself and also if you are looking at a newsletter or looking at book sales where you actually have data, right? Like, okay, I am right now as we're talking like in this exponential phase, which will inevitably end. And in fact,

in my case, because we're very seasonal, will reverse, right? So if you're running the lobster boat truck in Maine, right, selling lobster rolls, and you're gonna be busy in August, right? You can't extrapolate that to 12 months a year. Yeah, one of my theories of Peter is, Peter Thiel is fascinated by René Girard, but René Girard's theories are nonsense.

And people only like him because Peter Thiel likes them, which of course proves Girard's theories. Like there's something about the effect of being powerful and important and right about some big things that makes it hard to then, like my friend was saying the other day that having a contrarian theory that turns out to be correct can be a brain destroying experience. And how do you think about that with some of these figures and people you talk about where it's like,

they were the one out of 100. And so 99% of the population was wrong. And now they have a view that's insane or stupid or weird. And the same 99 are saying that's stupid or weird. It feels exactly the same way as last time. It's very intoxicating, right? You know, the most intoxicating thing in poker is when you make a daring play, like you call down a bluff in a spot where ordinarily you're not supposed to call

according to the game theory, right? Or you make a really big bet for spot where ordinarily you're not supposed to call according to the game theory, right? Or you make a really big bet for value because someone thinks you're bluffing and you extract a huge pot when you're supposed to win a small pot instead, right? So the combination of the validation from being right and then also winning a lot of money from it, those two stimulus at the same time, that's very intoxicating and very hard. I mean, you play poker, the good thing is you do reach the long run. You've had great days and bad days. You kind of simulate the world at a much quicker rate.

And so you kind of learn that way. I think poker, again, I'm probably not using terms like stoicism correctly, but I think when you go to a tournament, I played the world's first poker, I play a lot of poker. The main event, final 100 players out of 10,000 last year, 2013. And by the time you get to day six, which is as far as I made it, every hand is worth the equivalent of a couple hundred thousand dollars in expected value. And I had a hand where I made this good call down and then doubled my chips. I go from having probably $200,000 in expected value in front of me to the equivalent of

400,000. In question I think about it, it's like, oh, it's monopoly money, right? You can't just get up and walk away in the World Series of Poker. You could, but they would blind you off, right? So you'd just be paying a penalty. You have to play to the end of the tournament. You could leave and you'd blind off and get whatever prize you want, but you're competing for like $12 million.

But it's not like a regular casino where you can take your winnings and be like, I'm good. Well, even in like, you know, the best spots in poker are probably high stakes private cash games, right? And even then, you know, you play a game and you have like a really good, often they're like six hours long or something. You play a game and you have like a really good first three hours, there are lots of times

and be like, I just want to go home and get a nice dinner or something, right? But you, I mean, that's considered like bad etiquette and you wouldn't be invited back to the game. So it's actually a similar dynamic in high stakes cash and regular cash in the casino where it's open invitation to anybody, then you don't have that dynamic. Sure, sure. You can quit and you often should quit probably because there's winner's tilt, it's called.

When you're on a winning streak, people think, oh, tilt is when like you take a bad beat or you're on a losing streak and you're emotionally distressed about it. But like winner's tilt, when you think you're like God's gift to poker're emotionally distressed about it. But like, winners tilt when you think you're like God's gift to poker or sports betting or venture capital or media entrepreneurship or whatever else is, you know, very toxic as well. Yeah. Yeah, yeah, that makes sense. I'm Afua Hirsch. I'm Peterua Hirsch. I'm Peter Frankenpem.

And in our podcast, Legacy, we explore the lives of some of the biggest characters in history. This season we are revisiting the life of Cecil Rhodes. From sickly child to diamond tycoon to leading colonialist in South Africa, he was a bastion of British imperialism. Over the past few years campuses around the world have been met with students chanting, roads must fall. His legacy has been completely transformed. Follow legacy now wherever you get your podcasts. Welcome to Origins with me, Kushtumbo, the show

with the biggest names in entertainment tell me the stories that made them who they are today. Origins is a conversation about my guests' early inspirations and growing up. Guests this season include Dame Anna Winter, Poppy Delevingne, Pete Capaldi, and Golda Rushaval, aka Queen Charlotte in Bridgerton. I only kind of discovered my sexuality when I went to drama school.

Join me every week to hear where it all began. From Sony Music Entertainment, this is Origins with Kushtumbo. when I went to drama school. Join me every week to hear where it all began. From Sony Music Entertainment, this is Origins with Kushtumbo. Like I think about this, when I went to my publisher and I was like, I want to write a book about an obscure school of ancient philosophy, they were like, what?

Yeah. You know? And then, so it worked. And fundamentally all entrepreneurs have some version of this dilemma, which is like, you did a thing that wasn't supposed to be possible, that everyone said wasn't gonna work.

And so do you take from that, like don't listen to other people or that you were a genius. You know, like the story you tell yourself coming out of having defied odds is a pivot point in your life. I mean, I think there is some kind of social intelligence and kind of reading what's on the periphery

of the acceptable, right? That could become mainstream. I think there's gotta be some skill there. I don't think it's totally random. No, no, I don't think it's random. It's just like, but thinking about it that way versus like, I can predict the future, I'm a trend maker, I will this into, the story you tell yourself determines,

like, does Google see itself as this like, revolutionary, like, world changing company? Or they're like, hey, we bought YouTube, that turned out to work good. And then Gmail was this internal experiment that worked out okay. You know, like your story about yourself is going to determine how you interpret risk in the future and how you estimate your own capacities and competencies. Look, I do believe that life experiences teach you a lot, which I know was a cliche, but for some people, they have a hugely high motor in their 20s and 30s, and then they settle down, which is a normal, healthy thing to do, right?

But the thing they learn in their 20s and 30s, they're no longer able to apply those lessons in a higher leverage way. Whereas if you've had nine lives in think like I still have as much energy intellectually as ever, right? And I know where I fucked things up and can course correct. And you just develop over time, like different types of skills. I think I've gone from more introverted

to more extroverted. And if you have, you know, your intuition, this is a big lesson for poker too. If you have lots of experience, lots of data, then your intuition is extremely valuable, right? The problem people make is like when they're in a novel situation that they have no experience in or no good direct analogy for, then their intuition sucks, right? They should slow down and be more rigorous about a problem. Like COVID, people don't think very well about exponentials and how they work. So it's like, okay, well, let's have like,

you know, Bill de Blasio, the mayor of New York at the time, was like, we're gonna have to shut things down for a little bit, so go have like one big blowout at the bar the day before we shut down. If you worked out like the day before. Yeah, and like that's like literally the worst time possible to do it, right? That is gonna offset like weeks and weeks

of social distancing, whatever you call it. And like people's intuitions don't grasp that, I don't think. Where you guys say, hey, everyone, let's fly home. Like everyone fly home on the same planes from those countries. Just the think, the ability, yeah. Well, I think you have, so it's like you have your intuition

and in some cases getting stronger. And then you're also gonna be finding yourself in novel situations like that. Physicist John Wheeler talked about how like, as your island of knowledge grows, so does the shoreline of ignorance. So you're going to be bumping up into stuff. And so that's where ego is such a problem,

because ego says like, well, whatever you intuitively felt, it served you well, all these points. Like you talk about Musk in the book, and Peter, I've heard Peter talk about this, but like Musk is this guy who just goes all in, both in poker, but also with his companies. So there's some version where Elon Musk, this sounds very dismissive

because he's obviously a genius in many ways, but it's like he's gone all in on each one of his companies and not blown up. That doesn't mean it was a good idea. It just means he didn't blow up each of those times. And invariably, one of the times it will blow up. Invariably, although he has, I think, many, many levels he could fall through

before he gets into too much trouble. Of course, of course. Yeah, look, I mean, again, I mean, a lot of the books about poker, so I don't feel too guilty about going back to the analogies there. In poker, you actually get enough data to calibrate, right? If I'm saying, Ryan, I know I have it really, we can,

but it just feels to me like you're bluffing. And maybe I can kind of semi-art and semi not. You can have like some meta macro tracker in your head of like, okay, it seems like of all the times I make a counter intuitive play based on my intuition, I guess therefore it's an intuitive play, a counter math play based on my intuition. Actually, I'm making a profit on those plays. Let me steer toward doing that more often. And then sometimes, especially if you've been on a winning streak, then you go overboard, right? Then you're like, oh, I'm going to make this really unusual play. It's like where the math just doesn't support

it at all. Or you misread an opponent because in poker, the signals are ambiguous, right? Some players get very nervous when they're bluffing. Some players are actually very calm when they're bluffing and get very nervous when they have like the opportunity to win a huge pot with a good hand. They have aces, they can't control their heartbeat or whatever. And so like you can pick up a signal, but interpret it wrongly where it's actually the opposite signal from what you think. Yeah. The thing about poker is you're getting lots of reps with similar situations and yeah, mathematical situations. Whereas like think about it. So it's, you add some intuition from your first book, then you have intuition, the experience of book. But like, even if you live for a long time and write a lot more books,

like three, four, five more reps, like, like, that's the tricky thing about life is that you don't, like I just interviewed yesterday, interviewed Francis Ford Coppola. And he went all he basically went all in on this like movie that he's doing. Like he sold his wine company, he's like betting everything on this movie. And if you saw the last trailer, like the trailer is like all the negative reviews for his other movies.

And he's basically saying like, the critics have always been wrong. The early reviews for this new movie haven't been good, but just like, let's just wait. And so it's like, that could be true, but it's not like he has like, it's not like he's done it a thousand times because it's so hard to do a movie.

So that would be so like, when are you actually making a data or probabilistic decision and when are you just fooling yourself that you are? You know, with books in particular, I mean, books actually have this kind of, you know, exponential success curve a little bit. And like with books, I mean, they can always totally flop. Right. I was talking with a very well-known author.

It's very successful. He's like, you never know a lot of books and like, you've probably never heard of three of them, right. Because three of them totally bombed and you know, yeah, Michael Lewis has a book that no one's heard of because it came out like on September 11th. Yeah. Oh, that's funny. Yeah. So books you inherently, I mean, anytime you have a book even have, I mean, I only had two. So now I'm being ridiculous

by trying to generalize from it. But- That's what I mean. It's hard, like, because the thing is so big. And like, you even think about this with some of the entrepreneurs you talk about in the book, like they founded one company or two companies. And then, so you're generalizing from this experience,

but it's not that much experience given the immensity of the possible experiences. Yeah, look, I am interested in reading about the business of the media broadly, right? And I'm talking to other people who are and just kind of doing case studies. It's not necessarily like where you apply like lesson A from point X to point Z or whatever,

but I think being like a little bit immersed in that. And, you know, I guess I'm not afraid to admit that I like games of strategy. You know what I mean? And like, I think it's a good product. I think it's a really good product. I worked my ass off. You know, I've been up for like, I mean, I took a little bit of rest, right, this morning. But like, but like, why not figure out ways to to market it?

Well, it's like you go to like a restaurant and you're like, you have this worst fucking name. You have great food, but you have the stupidest fucking name in the history of the world, right? And you're on this street that gets no foot traffic. Whereas for 10% more rent, you can go to the street across the block

where they get tons of foot traffic. And it's like, you just wanna like, come on. You made a bunch of decisions. Even if luck has a lot to do with it, you made a bunch of decisions that were like objectively constraining or self-defeating. Yeah, as a creative, if you're not willing to market yourself,

maybe you don't care, right? Maybe you just are totally non-materialistic and you find a small audience and you go to some independent bookstores and you live a good life and that's fine, right? But I think creatives need to get better at like the, at the business side of things. Well, that's, but that's the hard part is so like,

if you're a novelist, you might write five novels in your life, so you can't get that much experience. I got very lucky because I was in marketing before and then I worked in book marketing. So I got to run the campaigns on a bunch of books. Like I did both Will Magascos books. So all different kinds of books, all different genres, people with platforms, not with platforms,

famous people and not famous people. So I could like see, be involved in decisions that like where you're supposed to have skin in the game, but it was nice to not have skin in the game. Like I got to learn from other people's experiences to sort of widen my data set. But yeah, you make, people make a lot of dumb decisions. They're, they wrote the book because people's experiences to sort of widen my data set. But yeah, you make people make a lot of dumb decisions there. They wrote the book because it's exciting to them and they didn't think like, well,

how is this actually going to be relevant to people? Or why would anyone have you come talk to their employee? Like you should write about the thing because you're interested in it. You should make the movie about it because you're passionate, whatever it is. But if you haven't also sat down and thought like, how is this going to play to people? Why is it relevant? Why is it going to work all of those things? You've made it unlikely that you're going to be that successful and I'm sick of extrapolating from the line going up must keep going up

So the one smart thing I'll give myself credit for for this book because I read the proposal right proposals in February March 2021 We're still emerging from the pandemic Yeah, all the books are about how bad Trump is or about racial equity and things like that, or gender equity, things like that. Whatever the trends of the moment were. Right, and I'm like, look, people are gonna get sick and tired of this stuff after, especially with Biden in the White House,

for two or three, after two or three more years. So having a book that's kind of unexpected and fun, so you're kind of predicting a vibe shift in the desire for consuming politically adjacent. We also have to think about the way books work, which is books have the longest shelf life of any of the forms of entertainment, right? And so, or one of the longest shelf lives.

And so a lot of people write books that are very much of the moment, even though the curve for adoption for a book, like how many, like you ask people, like what was the last book you pre-ordered? Or was the last book you read like even within the month that came out, like I always get around to books like, unless I'm interviewing the person like a year later,

two years later. So if you chose to write about something that's not gonna last for a minimum of one year, you've already eliminated a huge chunk of its potential audience, right? And so people don't really think about those things. And as they just make creative decisions when they really needed to make creative decisions that were then weighing some of the stuff you talk about

with like risk and expected value, just a slightly different decision or a different way of positioning it could have allowed the thing to last for 10 years as opposed to 18 months. And then, you know, we're in Austin, so the, you know, home of like slow cooked barbecue, the probably technical term for it.

Like that boiling process or the slow cooking process allows certain things to happen, right? That you see worlds evolve, you see narratives actually get tied together in unexpected ways, right? Sand bake been freed is maybe one of the most important figures in the book, was like not even on my initial list in 2021. His entire rise and fall kind of happens in the timeframe of the book.

Or like someone like Sam Altman, where I talked to Sam in August, 2022, when they kind of knew behind the scenes that like GPT 3.5 and four are gonna be really cool, but they're not as high profile, right? And so later I tried to re-interview him and he's like, you know, the biggest busiest man in the world, we do a little bit by email. I'm like, actually, this is much given the choice to have an interview after the breakout

or kind of in the middle of their process when he's less guarded in August, 2022. Like this interview is actually much better, the one I already had in the bag. So things like that are helpful with the book. Yeah, yeah. You never know where things are going to go. But if you are trying to think of optionality as opposed to locking things in, you have more. Well, that's the other kind of, I feel like if you understand optionality, that might be like the single most important skill if you're anywhere on kind of the entrepreneurial mindset.

That cultivating opportunities that lead to more opportunities instead of nodes that are closed is just this incredibly valuable, exponentially better skillset. And it might mean saying yes to more things, to more, you know. I think about how I've made friends,

then it's often through some friend of a friend, you met at a party that you didn't actually want to go to that night or something, right? But you just wanna like, you wanna go where doors are likely to open and lead to other doors. And if you don't do that, then I think you're making a big mistake.

I struggle with that because obviously to be good at something, you have to say no to things a lot and you have to be disciplined. things a lot and be disciplined. And at the same time, when I think about the things, like I met my book agent and some of my best friends at like a conference I went to like 12 years ago, and I wasn't gonna go and then I went. And then now I spend most of my time

trying to not go to conferences. You know, these random serendipitous things change the course, the trajectory of your life. And also though, if you went to all of them, you would never have time to do what you do. And so how do you let that randomness in without being ruled by it? So one thing that helps me a lot, it's kind of unique circumstance, is because elections are these four year cycles, you naturally have up cycles and down cycles, right? So you're going at warp speed in like the June

through November of an election year, and the other seven out of eight times through the rest of the year, then you can pick your pace a little bit more. Interesting. One of the things I was curious about in the book, so like it seems like these VC guys, what they're really good at is realizing,

okay, you can only lose the amount of money you put in, but you could potentially make an unlimited amount of money. So they kind of developed this mindset of taking these kinds of chancy bets. I'm wondering if part of the world we're living in is their struggle to realize that most things in life are not that way. For sure, right?

I think they, you know, things like their intuitions about politics tend not to be very good. Like, you know, Peter Thiel's a smart political thinker, but like the candidates that he's kind of endorsed tend not to sell very well to mainstream America necessarily. But I think it's more, what I'm saying is like, okay, so Peter and I sensed this very much when I was writing the book,

because I remember I was in his office the day he announced that he was donating that first money to Trump. And I remember sort of asking him what he was doing. And he was like, well, you know, it could work, you know, and it ultimately did work in that Trump was elected. But I think he was thinking about it's like, okay, it's only a million and a half dollars, which is something only a billionaire would say. And someone who has a sense of how much money gets thrown in politics, that seems like not a lot of money. But he's thinking like, all I can do is lose this money. But actually what happens is that donation,

just like the Gawker thing, you know, he's like, hey, I'll spend $10 million, who knows what happened? Well, it also changes the trajectory of his life in the sense that, like, I don't think the Trump thing would have happened without the Gawker thing. And I don't think being right about the Trump thing. If he had not made that bet, I think being right about something can radicalize you, it changes the people you spend

time with, it changes how the world sees you. I know he wasn't thinking about what other people would think because that's not how he thinks. And yet you end up having to live with your reputation and, and your place in the world every day. Yeah. If people who want doing the kind of meta rationality stuff, don't realize the extent to which, I mean, when I started like writing and tweeting more

about COVID where I don't know, I think I actually have a very centrist viewpoint, right? I thought the lockdowns were bad. I think the vaccines are good, right? I thought we had to get back to normal at some point after vaccines were available. But yeah, when you're identified with a certain political bent and you're more outspoken about things than the people that you meet change in like types of subtle ways, right? It's like not like I've ever had a friend like maybe one cancel me over politics. Yeah. But it just kind of changes your trajectories a little bit and if you don't realize it, then I mean, the other thing too is, look, I think if you have a general bias, the average

person is too conformist. Yes. But you see people in Silicon Valley and these different sub communities and the rationalist community where they maybe they have some successes and then just go way overboard or maybe they're living their great life. I don't know. But yeah, that first succulent taste of success by making a contrarian bet and having it be right is very, I think, addictive. Yeah, it's addictive and then yeah, it's changing the reality you're in. But I remember he said something like, and I don't mean to make this all about him, is you could do this with Mark Andreessen or Ackman or whatever,

but he said something that was like the Trump thing. He's like, there's a 20% or 30% chances could all end in disaster, but you know, whatever. And so it's like, if you're betting on a company going like there's a high chance of success, that failure is capped at zero, it's great. But like the presidency ending in disaster is, you know, one of the possibilities there

is nuclear Holocaust. Like you need a balance of the sort of swashbuckling risk taker and that attitude is particularly conducive and successful in places conducive to it. And then there's this other part of our world where like, I'm not sure you want to introduce the river mentality. Yeah, I mean, part of it too is having some like

meta rationality about where are the weak points in your mental model? Yeah. And how fragile are they? This sounds like Taleb a little bit more. But yeah, if you're sometimes you're making a model, like an election model, which is pretty complex, right? There's several thousand lines of code and you'll focus so much on some very small detail

like the second congressional district of Nebraska, which awards one electoral vote, right? But then some very major parameter like how much error do we expect there to be in the polls? You just estimate really quickly and that's, or there are bugs in your code. Every year I go through and kind of not really rewrite the code, but go through and say, is there anything I should change? And you discover, oh, there was a minus sign where there should have been a plus sign, right? And that's a very minor operation. It doesn't matter, but it's been there for 12 years now. It's not really affected or

anything. But you have to be... Yeah, people I think are... They focus on the parts of the problems that are nerd sniped, right? Where they're fun and intricate and interesting and don't kind of zoom out. And that's kind of where some of the skill comes in. And I think, you know, if you actually have experience having skin in the game and gambling or doing things adjacent or analogous to gambling, like that makes you a lot better.

Like the pure academics are almost always like really bad at modeling. Yeah, because they don't live in the real world. Like, I mean, is there anything less real than tenure? I don't know, maybe, I mean, you have- I can see its value. I'm just saying like there's something inherently, like we're accepting that the people we want to think

about our world, we give them a kind of career where they exist in a different reality than 90%. Yeah, maybe we should, it's the same with the Supreme Court appointments, right? Yes. Maybe we should have like five-year grants of tenure where you have five years, like a MacArthur grant that's sponsored by the University of Texas or whatever, where you have five years where you can't be fired for any reason except for like, whatever, severe crimes, felonies.

Sure. And you can do whatever you want, there's no obligation. And I think maybe you're awarded by some type of weighted lottery. So, you know, maybe you have some people who you wouldn't think are obvious candidates who get one and some people who are more obvious or whatever else. And like, that might be valuable for society, I think.

I mean, the teal funds for like kids to drop out of college is kind of a little bit trollish but it's produced some good. Yeah, a bunch of incredibly successful, interesting, interesting people. Yeah. You know, I do think we're still on like a trajectory away from interesting stuff happening in in the Academy. I mean, AI is happening almost entirely outside of academia. Yeah. And outside of government, for that matter, really. I don't know what the DOD is doing or whatnot. That's that's pretty interesting. Yeah. The idea of like, well, we don't have this. I don't know what the DOD is doing or whatnot. That's pretty interesting. Yeah, the idea of like, well, we don't have this

because I don't know the government, you have 10 years so the government can't persecute you, but are there that many academics doing work interesting enough that the government would persecute you? Do you know what I mean? Like they're inherently kind of not super transgressive. Like it's mostly people saying the same things. Yeah, I mean, look, the most interesting

philosophical movement in academia is probably effective altruism. But they have, which you're responsible for, I guess now in part, right? They have really good marketing. They have really good engagement with the outside world and they're kind of like straddling these lines a little bit more and yeah, the pure academic stuff.

I mean, look, I think there are some course corrections. The fact that you have schools re-requiring standardized tests, I think, is probably good and things like that. Oh, sure. Yeah, the effective altruism thing is really interesting because I really like Will McGaskill and I think his work's important,

but it was fascinating to watch the difference between the first book and the second book, just how much money they had to throw at the book. Like, the first time they were like, okay, we've got this little marketing budget, what could we do? And we came up with a bunch of interesting ideas. And then the second one, we'd get on these phone calls

and they'd be like, well, what if we just bought a million copies? And I was like, well, definitely don't do that. Like, doesn't your thing say that if you have what, $25 million to spend, you should save hundreds of thousands of lives in Africa and not buy books. But they were like, but if we get the ideas out in the world, and then it's spread, you know, our ability, our mind's ability to like corrupt itself and find ways to do what ultimately just assages the ego or makes us feel important or win

recognition is just such a fascinating force to watch it happen to supposedly these hyper-rational and fundamentally decent human beings who want to make a positive difference. They went from like, save the child drowning in a puddle or eradicate malaria to like, thought experiments about AI a thousand years from now. No, I think EA and maybe utilitarians in general wind up in this very weird space

where like sometimes you're supposed to do politics, sometimes you're not. Right. Remember when like I agree that Will is like a very thoughtful person who is a smart guy who wants to do good and has done good, like done good more than most people who talk about doing good, just like from his own salary donations. Yeah, but it's a bit like, okay, so Tyler Cowen asked him about abortion and personally I'm pro-choice, right? So it's not a concern for me.

But if you're concerned about future life forms, which is what it's all about, how can we maximize the happiness of future utilitarians in the world, right? And like, then, you know, abortion becomes complicated from that framework. And he's like, oh no, oh no, it's a woman's right to choose, of course, of course.

And you can kind of rationalize it, but I think it's probably a little bit inconsistent. But then you can say, oh well, most of my donors are liberals or center left, and they're very pro-choice, and we already have a woman problem in EA, so I can't be pro-life, and so on some grander level and it's just kind of like, there's no there there on some level, you know what I mean?

Yeah, it's a moving target that they get to define, I guess. Which is why I think you can't have like, I don't think pure utilitarianism, I think it falls apart on some grander level, right? It falls apart without some constraints or principles that you establish. Welcome to the Offensive Line. You guys, on this podcast, we're going to make some picks, talk some s***, and hopefully make you some money in the process. I'm your host, Annie Hagar. So here's how this show is going to work, okay? We're going to run through the weekly

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and my podcast is back with a new season and let me tell you it's too good and I'm diving into the brains of entertainment's best and brightest, okay? Every episode I bring on a friend and have a real conversation. And I don't mean just friends, I mean the likes of Amy Poehler, Kel Mitchell, Vivica Fox, the list goes on.

So follow, watch, and listen to, baby, this is Kiki Palmer on the Wondery app or wherever you get your podcasts. In retrospect, I think you end up, the more I kind of think about the founders, the more impressed I am with the complexity of the checks and balances that they came up with in such a short amount of time.

Because yeah, we see these movements happen, whether it's EA or I don't know, like Wikipedia, or then you see these things happen and then how quickly just like human nature manages to find whatever the vulnerability is. So EA is like, it's this great pure thing, it's struggling. And then they get the money they always wanted. And that money, like in some ways just breaks

the whole thing because they just didn't have, Black Lives Matter is another good example where it's like they just get hundreds of millions of dollars. And because what they actually wanted was not clear to themselves, they were actually harmed by the influx of support and money and the internal contradictions of the movement. But then also the personality flaws

of the people at the head of it, eventually it just collapses under its own weight. Yeah, the obsession with scale, which is partly something you can blame the VCs for, is like, you know, businesses in Europe classically, you just have like one manufacturer of Parmesan cheese that makes the best Parmesan cheese in their region of Italy for 500 years, right?

Zildogen Symbols has been in business since the 11th century. Yeah. And that's a great business. And we don't tend to appreciate that type of business in America as much, especially in the content to bring it back to our field, right? I think VCs tend to analogize media startups

like tech companies when it's more like running a restaurant, right? You more like running a restaurant. You can run one really nice restaurant. If you're very lucky, you can even franchise that to a couple of locations and you can write a cookbook and you can do one Iron Chef or whatever. But there's not 100X scale unless you want to be Chipotle or something, which is fine. Yeah. Or you spin off Shake Shack from Danny Meyer's thing. Yeah, and they're not part of the same. Danny, there are exceptions, right?

David Chang or Danny Meyer, right, are people that have managed to kind of keep a high quality product and they have their flagships and they have their expansion. But they're, you know, but they're kind of like once in a generation geniuses pretty much. Yeah, I know. That's an interesting point. Like the New York Times is a family owned company. And that's probably interesting. It Like the New York Times is a family owned company and that's probably-

That's interesting. It's publicly traded, but family owned and that check balance has worked, although the Washington Post is in trouble because it's just all owned by one guy. Yeah, I mean, look, I think we're probably moving toward winner take all in everything, right? And the Times I think is becoming like a winner take all

media company, but to their credit, they have become, you know, I had kind of a bad falling out with The Times when I left, right? But they brought me back in to like, you know, and do op-eds with them and be in their podcasts and things like that. And so, you know, they're not holding a grudge because they're like, yeah, we're the best media brand in the world right now. And like, we're not going to worry about like having grudges if it makes our product better and like we have more interesting content. So I think, yeah, they become a uniquely well-run business, I think. But it's also like the treadmill of human capital or the accelerator of human capital where once you start to do well, then you develop better context and hire better talent, right? And then at some point it stops. I mean,

you know, the reason why like the Xerox Corporation didn't become the dominant Google of today is because you do develop these encumbrances where the founders lose their motivation and then with every node of management that you add, then you just become a lot slower about things. And I'm thinking about this stuff because the Stoosler is now doing kind of insanely well and I have one part-time employee and then my partner helps out de

facto two part-time employees basically, right? And we're meeting all these companies with like 30 employees and things like that. And it's like- The discipline to not scale is actually really interesting. Like Robert Greene talks about it via Machiavelli, but the idea of not going past the mark you aimed for and just be like, I wanted to run a newsletter. I wasn't trying to start a multimedia company. And to like, I've had to really go like,

yeah, I want this to just be about this big and to put a ceiling on what you're doing. To turn down money is a really hard thing, especially if a VC person is offering you no strings attached money, but there are strings attached. No, it's like, so I call it like the dessert analogy where like you'll go in and you have your dinner and you're like, I'm not gonna have dessert.

I know how to satiate myself with my main course, right? But the person selling dessert, i.e. the waiter, they know that you're kind of full and they know how to say, oh, here's a dessert that sounds light. It's just some strawberries and cream or something, right? Or why don't you indulge? Why don't you, you deserve it.

I know that you're, it's an indulgence, but now it's time to indulge. Or there's like something fruity. You're like, so they always kind of, or savory. It's gonna feel bad afterwards, but you can't. Yeah, so you have to prepare for the fact that like people, it's like whenever there's like a big scandal where like everyone's emails get leaked,

like Sony corporation or something, it's like, yeah, my expectations are probably some pretty bad shit in there. So the fact that you identify some particular bad shit doesn't really change my priors very much, but. Yeah, yeah, yeah. Yeah, to just be like, hey, I'm willing to stay. Like, WeWork is a really good idea.

It's not a $40 billion idea. And it shouldn't be in every city and they don't need 50 buildings in every city. But like, yeah, so the discipline to be like, I'm gonna have an extremely profitable, interesting this is that takes a lot of discipline, especially if you're surrounded by lots of people who don't have discipline.

Yeah, maybe you need some like VC firms that focus on that. I mean, maybe Y Combinator is kind of a little bit fair. They seem to be more okay with. But they're investing really early, hoping you become one of those companies and then their 1% becomes worth like a trillion dollars. Yeah, it's hard. I mean, this is one of the things too, is like the inevitability in a capitalist system where people are in an independent-minded country, like the inevitability is that there's going to be competition and you can't turn that off. And so you may as well compete, figure out what you want,

but you may as well compete or you just get trampled, right? Or you're just screwed. It's a capitalist system kind of in an evolutionary way, attempts to rein that in, inherently don't seem to work well and or substantially lower human welfare. But to go to your casino metaphor, you have to have the ability to win money

and then walk away. Yeah, which most people don't. Because you know it's gonna go away if you don't. Yeah, yeah. That's the hard, yeah. The other thing I thought was interesting, you were talking about this in the book, because there's lots to critique in the village,

but the idea of peer review or a culture of criticism, I was on this text thread with a bunch of like some of the some of the people in your book, and the degree to which they were always complaining about media coverage of them, that they interpreted as extremely negative, which a normal person like me would go, No, your company is worth $8 billion. This is like is actually very nice coverage. This is the expected coverage when you are not the underdog anymore. And so you noted that there is kind of a culture of like,

we're all supposed to root for each other. And that's not one how the world works, nor is it ultimately the way the world should work. When you go from underdog to established incumbent, that can switch very quickly. I've experienced that. You see people turn on you, not in a personal way. I have loyal friends and I'm loyal to my friends, but the general zeitgeist, whatever you want to call it, can turn-

You're not Nate, you're a news story now. Yeah, so Garrett Adelstein's a poker player who was involved in this famous scandal where he accused another player of cheating, right? And he was like, beloved, and he's a sensitive guy, right? He's talked about his battles with depression and things like that. And he's like, you know, I couldn't handle

with now being perceived as the villain because I went maybe overboard in accusing a player who might have cheated before there was proof. And like that's very difficult. Yeah, like the idea that Silicon Valley, it's like you guys are all rooting for each other, not because it's like this love of the weird and the innovative or whatever,

it's that you're all invested in each other and there's some element of a hype, like a pump and dump thing that's going on here. That's accusing them of criminality in a way that they're not. But they are all incentivized to inflate the evaluations of their companies. And then they're like surprised that the New York Times

or random, like a 20 something, you know, reporter in New York City who's just tweeting about stuff is not equally incentivized to help them inflate the values of their company. It's like, they're doing their job. And the inability to grasp that and then also to see the good that comes from like, if Silicon Valley had been exposed to more criticism internally, maybe the WeWork thing doesn't happen. Yeah. Look, you can always have overcompensation. I think the tech press was kind of very friendly to tech in like the Obama era. And then things

started to shift and sometimes it's unfair. I mean, I think like, like I'm not a giant fan of like the company Facebook or Metta, I suppose, a neutral opinion, but I think they were unfairly accused of the whole Trump Russian bot thing was a very minor story that blew up and memeified a little bit. But yeah, most of the people are doing exceptionally well and don't need to worry about the haters so much. But if you're someone like an Elon Musk who was very popular in both the river and the village, because it's like electric cars and rocket ships and things like that, safe since they're left, when people turn on you, then you can just kind of lose your shit, right?

Yeah. I'm fascinated by that. I'm writing about it in the book that I'm doing now, and it's extra interesting because he moved into this little town the the Tesla factory is just on the other side of Bastrop County in Travis County, but like in this little town like SpaceX Boring company Starlink is here. He's moving all of Twitter's customer service here He like owns this town now, which was like not the case like just a few years ago. It wasn't it wasn't the case I've been here a long time, But like it's fascinating to watch. I like that thing that came up with Trump

where people say like every accusation is a confession. I think it's interesting to watch someone rail about the woke mind virus when they very clearly have caught some kind of virus that it's utterly changed how they perceive the world and act in that world. And typically there are people that are more, I mean, rationality is a loaded term.

But there's like, you know, Michael Moritz seems like a pretty sane and well-rounded person, for example, or, you know, Vinod Khosla, am I saying that right? Conway. Yeah. There are people who are quite sane. And like, if you're writing, you know, one bias that I think every author will confess to

is like the subjects that are more willing to talk and that are more interesting story-wise are gonna get like, A, over-emphasizing the text originally, and then B, when you do like the media for the book, right? Yeah, sure, that's what we wanna talk about. Elon, the two Sams, Peter Thiel, and people like that. Yeah, yeah.

Maybe Mark Andreessen. Those are the big five bad boys basically, even though they're not all bad. Right. Yeah. But what do you think about this? It does seem to be kind of a process where it's like, they tweeted about this, then they tweeted about this,

then they gave these comments. It's almost like, it's not a cliche, but it's like, I know the cycle when someone's like, we're like, oh, we call it being red-pilled, I guess, but you can kind of, you could almost predict where and when it happens for someone. I think there's like an autoimmune response

that can happen, I think. What's really tricky too is that like, you could have the same kind of emergent behavior with things that are organic or coordinated. And it's like very hard to recognize kind of what the pathogen is. You know, you might notice that like, I don't know, I have a good example offhand,

sometimes certain phrases that may have nothing to do with anything just kind of go through ebbs and flows of how often they're used. And that just occurs over time. Maybe you read in a popular book and so you start using those phrases and there's lots of subliminal shit.

But also when Penguin is dropping my book, that's a coordinated marketing campaign where we're doing 30 interviews and months beforehand you've emailed influential people, say, hey, you want a galley dropping my book, that's a coordinated marketing campaign where we're doing 30 interviews and months beforehand, you've emailed influential people, say, hey, you won a galley of my book. And so that's very non-viral. I mean, it can become viral, but the spark for it is coordinated.

And it's hard to tell which is which sometimes on Twitter. I think 98% of the time it's actually not coordinated, but you can get paranoid about the 98% of the time, it's actually not coordinated, but you can get paranoid about the 2% of the time when there are, whether it's bot farms, I mean, you have obsession with bots, right? So it's coordinated or whatever. No, it's mostly just like people are similar to one another and behaviors contagious,

and mostly it's spontaneous and organic. And the fact that there are exceptions to that, where you have media groups that are trying to shape a narrative that can happen sometimes and it may make sense to have a scapegoat in those times to focus on Elon or Nate Silver or Ryan Holiday, whatever else, instead of having some diffuse focus. Who can embody the trend or the problem

that we're talking about. It's mostly emergent properties of inherently complex systems and the internet. It's interesting to me. You have a person who's incredibly smart, has unlimited resources, etc. They're not immune from whatever the algorithm can do to a person. I just think that's so interesting. Although if you imagine Nick Denton, he's like, oh, things are going strangely here. I think that's so interesting. Although if you imagine like Nick Denton, he's like, oh, things are going kind of strangely here, right?

Maybe there is some, because it sounds so paranoid. What if there's a secret billionaire secretly funding this lawsuit against me? I mean, it sounds like completely fucking paranoid. And it probably is 95% of the time, but then he's in the 5% of the 2% when it's exactly right. Yeah, that's true. There was an interview where somebody put it out

and Peter, I remember Peter saying that they thought they'd been caught, but it was too preposterous and so nobody believed it. Absolutely. So yeah then with the time the conspiracy theorist is correct that's the brain-destroying experience because now you see it everywhere. Like I I noticed like of the people the people that I knew and I don't know exactly how I came to know these people, but I knew a lot of people that were in like the paleo space, like the paleo diet.

Almost to a man, they all became during the pandemic, like hyper radicalized about COVID and vaccines and whatever. And when I'm trying to be charitable to what happened, it's that they grew up with the food pyramid and the food pyramid is bullshit and not the diet you should eat. And so there kind of was this conspiracy

like to tell people that what is healthy is unhealthy and what's unhealthy is healthy. And so the people that would be attracted to that are, and then they've seen it and had it confirmed, it's gonna be hard for them to trust the consensus going forward. No, it's also because people are, language and political positioning can be,

there can be an element of bluffing, for example, right? Like if I say, oh, I wonder, this is a slightly spicy example, right? Some people when they say, I wonder about trans athletes in college athletics or something, but otherwise I'm very supportive of trans rights. And they mean that.

So this is just an edge case, right? Some people say that to test the waters because they're super anti-trans. And without more information, then you kind of don't know which is which. Yeah, yeah. The village is very bad or has a lot of trouble separating good faith

from bad faith. For sure. And that's kind of a weakness of trouble separating good faith from bad faith. For sure. And that's kind of a weakness of our system. So like you think about the lab leak thing, right? Like the village rushes to kind of shut that down as a hypothesis. And part of the reason they rushed to shut it down is that a good chunk of the people who are bringing it up

were bringing it up in bad faith. These were the same people that doubted literally every other part of COVID. And so intellectually, how do you deal with ideas that may or may not be true, but are being weaponized either by foreign actors or weaponized by influencers or grifters or just people arguing in bad faith?

That's a really tricky thing that I don't think we've figured out well as a society. No, look, I think people in effective altruism have something of the same problem, right? Where they are, it's a small community and they were like way too trusting of SBF in particular. There are a few other examples. But yeah, this is a big problem in the villages.

They don't understand that like, there are people that for political reasons or for personal gain or for clout building, or it's because they're wrong, but happen to be wrong, but persuasive. They're people who would take advantage of your trust and take advantage of the trust that people have in this expert institution and therefore undermine the institution. So you have to police from within a little bit more. And if they're a culture of consensus, whereas in the river, we criticize and, or we bet, right?

Maybe betting is a better mechanism actually. But in the river, you're supposed to be critical. You're supposed to look for opportunities. You're supposed to look for an opponent whose play of a poker hand doesn't make any sense or a bad betting line that DraftKings posts or whatever else. And so like, I think that's actually a healthy impulse up to a fairly high point. I'm saying kind of the opposite though.

Like, so if someone is arguing something from bad faith, like they're not smart, they're a conspiracy theorist, they're whatever, it doesn't necessarily mean that that idea is untrue. That's probably true. And so how, like, I think that's during the pandemic, there were like, when you had a group of people who were just deciding that the virus did not exist

and it had no consequences, and they were politically motivated to continue to just resist whatever the people in power were doing, there kind of became this reflective dismissal of every concern and doubt. So like when they were like, hey, I think it's time, like in Texas, we reopened everything in June of 2020, which was objectively too early.

But then when people were trying to reopen schools in June of 21 in California, those people were treated as though they were the same people and they're not, right? Yeah, I think we should look at political beliefs as kind of not that important in terms of forming interpersonal relationships. Cause like for religion,

I guess I call myself agnostic or something, right? But probably a phase, right? I call myself more aggressively atheist, right? Someone's like, I'm a practicing Catholic. I wouldn't have been in that phase like, oh, fuck you. I'm never talking to you again. You must be crazy, right? It's like, okay'm a practicing Catholic. I wouldn't have been in that phase like, oh, fuck you, I'm never talking to you again. You must be crazy, right? It's like, okay, you have a belief system

and we can still go and get a beer together or enjoy hobbies together or whatever, right? Have a friendship or relationship. People I think need to indulge other people's incorrectness, sometimes more often knowing that you have, it's reciprocal, that you undoubtedly have beliefs that they find wrong or objectionable or annoying, and they're still your friend.

So I think people should think about that. It's funny, Obama talked about this in his convention speech. Yeah. That like, especially for Democrats who are trying, who by definition, having to create a fairly large consensus. Like you need a lot of people.

So you are a coalition. A minority position can be intellectually pure. But if you're trying to create a broad consensus, you can't. I mean, Democrats have always been the party of misfit toys, right? People who are intellectuals, people who are struggling, right, you know, gay people and immigrants and things like that.

It's misfit toys and you have to tell, I mean, one thing I love about New York City, where I live is like, in New York, we have to tolerate one of those eccentricities, right? You cannot, because you just will not survive a day without like having like high practical tolerance, which is like different than like the Dutch tolerance, right, which is, you know, I have some like Dutch friends,

like you can do what you want, but they're judging you the whole time. You know what I mean? Yeah, yeah, I saw this TikTok and they were talking about it and they were just like, the rules of New York City is like, you didn't see shit. You know, like I, not like you're embracing it.

It's just like you're fucking minding your own business and you're not, somebody's jumping the subway turnstile. I don't know, I didn't see, just like that, that's kind of the,stile. I don't know, I didn't see just like that. That's kind of the, don't ask, don't tell is obviously a bad phrase given what it was used to do, but it's not a bad policy for the rest of life. It might not have been a bad policy for the military

in that environment, right? It's better than persecuting somebody for having gay relations, right? And the maybe- I'm saying it doesn't go far. It was inherently discriminatory. You're right. There was some good intention there,

but I just generally not asking, not telling, as Tim Walz has been saying, mind your damn business. It's a good strategy for life. No, I think, another poker thing. Sorry to go keep going back to poker, but there is a cost to giving away information, that there are reasons why you want ambiguity sometimes and you don't want complete transparency. And you are communicating by not saying something and you can increase optionality with ambiguity.

Sometimes one reason why I think that large language models prove surprisingly good is that language is very game-like in many respects. So they're good at solving chess or poker It shouldn't be surprising that they understand how speech works. Well shutting the fuck up is a way to increase optionality William Tecunza Sherman had this thing He's like never explain why you think what you think because you might change your mind. So like so Your reasons could change the conclusion might say like, so your reasons could change. The conclusion might stay the same, but your reasons for it could complain.

But so the optionality of like, I'm not gonna explain my opinion on everything or verbalize every thought as it's coming into existence is a way to preserve optionality, your reputation, and then also your sanity because you're not locking yourself into stuff. Or there might be kind of different equilibria, right? Either being really reserved or, you know, look,

if you're running a newsletter, then like a confessional style really works. Like I'm not posting this newsletter day because I'm, you know, I don't know, you know, on a plane right now and the wifi's not working, I just want to relax. And like, like that can work, I think, or being like quite selective and quite reserved.

And I think one problem that I had kind of working for the Walt Disney Company is I was stuck kind of exactly in the middle ground where I felt constrained, but then the constraints come out in Twitter or in different ways and like, it wasn't very ideal. I was thinking about this the other day. Like if I was going to inflict a horrible fate on someone, like I was kind of coming up with a torture,

like, you know, there's that Chinese curse, like may you live in interesting times. One torture would be, you're going to have strong opinions about everything you see, hear and read. And so you see how people inflict this fate on themselves. I mean, Twitter and social media is designed around prodding you and nudging you to have more opinions, concise opinions, polarizing opinions.

And so you not only get yourself into trouble because you can say things you regret, but I think it also, it changes you as a person because it opens you up. First off, you're now thinking that way, but also you are getting feedback for thinking that way and it becomes this kind of vicious cycle where you just become hardened and cynical. And also just like, I interviewed Stephen A. Smith one time and I was like, you have a thing that you can't turn off. Which like, you ever see him, like they'll ask him

like opinions about like, who would win? Like this Disney character or that Disney character. And he can like off the top of his head, just like create minutes of opinions about things that he's never thought of before. That strikes me as I like he's actually funny. But like seems kind of kind of genius, actually. But yeah, to do that to someone would be like a horrible thing.

It feels like I mean, I feel like I have trouble turning it on. Yeah, we can absorb and read and you don't have to like participate. But yeah, it is hard. I mean, you know, one thing I like about poker is it kind of because you can't leave a poker tournament without paying a price, it kind of is a commitment device a little bit, you know? Yeah. And how does that help?

It helps because it's probably good to have some downtime to reflect. And I enjoy poker and in principle, you're making, I'm in games where I'm in principle making money, but usually the opportunity cost would make it negative relative to some other way to spend my time. But I mean the commitment device, it just makes you have to stick with the thing you're doing, is that what you mean?

Yeah, so say, okay, I'm going to the World Series of Poker June 5th through June 22nd and I can't schedule any meetings, go to any conventions, right? Anything else during this time and like it's nice, probably you're better off like going to Japan or something, although I really like poker. But I think it's very important if you're creative to have downtime, right?

I'm not one of those people who like, I mean, now I'm supposed to say that I have to do it. But the people who are like, oh my gosh, I have a 20 minute Uber ride from downtown SF to SFO airport, I'm gonna bang out these six emails. Like you can't do that, or at least my metabolism doesn't work that way. Yeah, Churchill wrote this book

called Painting as a Pastime. And he said that every like important public person has to have like one or two hobbies. And his was painting and brick laying. And you have to have this thing that's very different than what you do. Or it doesn't have to be super different, but it has to be kind of use different muscles, put you in different scenarios. And the having that conduit,

I think prevents you from going crazy in your work life and using that as the your only means of expression and your only form of meaning in your life. Yeah, or something like the local equilibria, maximizing that and not the global equilibria is a very nerdy way to put it, I guess. Yeah, I think that's right. All right, I want to show you some books. Okay. You got a second?

Of course. Yeah. Thanks so much for listening. If you could rate this podcast and leave a review on iTunes, that would mean so much to us and it would really help the show. We appreciate it. And I'll see you next episode. If you like The Daily Stoic and thanks for listening, you can listen early and ad free

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