The Question That Haunts the World’s Most Successful People | Andrew Ross Sorkin (PT. 2)

Even the giants of history couldn’t outrun insecurity, comparison, or the feeling of not having enough. In today’s episode, Ryan continues his conversation with Andrew Ross Sorkin to talk about why success rarely feels satisfying in the way you expect, why the goalposts always seem to move, and how Andrew has seen this pattern play out in some of the wealthiest and most accomplished people in the world. Andrew Ross Sorkin is a financial columnist for The New York Times and a co-anchor of CNBC's Squawk Box. He is also the founder and editor of DealBook https://www.nytimes.com/section/business/dealbook, a financial news service published by The New York Times. He wrote the bestselling book Too Big to Fail https://www.thepaintedporch.com/products/too-big-to-fail-the-inside-story-of-how-wall-street-and-washington-fought-to-save-the-financial-system-and-themselves?_pos=3&_sid=4d3da5615&_ss=r and co-produced a movie adaptation of the book for HBO Films. He is also a co-creator of the Showtime series Billions. His new book is 1929: Inside the Greatest Crash in Wall Street History--and How It Shattered a Nation https://www.thepaintedporch.com/products/1929-the-inside-story-of-the-greatest-crash-in-wall-street-history-1?_pos=1&_sid=4d3da5615&_ss=r. You can grab signed copies of 1929 https://www.thepaintedporch.com/products/1929-the-inside-story-of-the-greatest-crash-in-wall-street-history-1?_pos=1&_sid=4d3da5615&_ss=r by Andrew Ross Sorkin at The Painted Porch: https://www.thepaintedporch.com/ https://www.thepaintedporch.com/products/1929-the-inside-story-of-the-greatest-crash-in-wall-street-history-1?_pos=1&_sid=4d3da5615&_ss=r Follow Andrew Ross Sorkin on Instagram @SorkinSays https://www.instagram.com/sorkinsays/?hl=en and on X @AndrewRSorkin https://x.com/andrewrsorkin?lang=en 👉 Support the podcast and go deeper into Stoicism by subscribing toThe Daily Stoic Premium https://dailystoic.supercast.com/ - unlock ad-free listening, early access, and bonus content:https://dailystoic.supercast.com/ 🎥 Watch the video episodes onThe Daily Stoic YouTube channel https://www.youtube.com/@DailyStoic/videos:https://www.youtube.com/@DailyStoic/videos 🎙️ Follow The Daily Stoic Podcast onInstagram https://www.instagram.com/dailystoicpodcast/?hl=en:https://www.instagram.com/dailystoicpodcast ✉️ Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email athttps://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 https://www.instagram.com/dailystoic/,Twitter https://twitter.com/dailystoic,YouTube https://www.youtube.com/@DailyStoic,TikTok https://www.tiktok.com/@daily_stoic?lang=en, andFacebook https://www.facebook.com/dailystoic See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:03Ryan Holiday?

  Welcome to the weekend edition of the Daily Stoic. Each weekday, we bring you a meditation inspired by the ancient Stoics, something to help you live up to those four Stoic virtues of courage, justice, temperance, and wisdom. And then here on the weekend, we take a deeper dive into those same topics. We interview Stoic philosophers. We explore at length how these Stoic ideas can be applied to our actual lives and the challenging issues of our time. Here on the weekend, when you have a little bit more space, when things have slowed down, be sure to take some time to think, to go for a walk, to sit with your journal,

• 0:46Ryan Holiday?

  and most importantly, to prepare for what the week ahead may bring.

• 0:54Ryan Holiday?

  Hey, it's Ryan. Welcome to another episode of the Daily Stoic Podcast. So back in last summer, I guess, when was it? I don't know exactly. I just go where they tell me when I'm doing press for a project. And they booked me on Squawk Box, which I was surprised and excited about. It's a show I've seen on TV many times. Try not to follow the market day to day. But if you're going to turn on a TV show and watch what's happened in the market, Squawk Box is like the morning show that people watch. And I didn't know exactly what to expect, but I showed up. We had a little great interview. Let me run you a little clip there.

• 1:32Ryan Holiday?

  Here he is. He's at our table, Ryan Holiday, bestselling author of multiple books on Stoicism. His new book, Write Thing Right Now, is out this week. Here it is. And this is book number 16. Yes. That's a lot of books you've been writing over the years. Are you a Stoic? I try to be. Can we define Stoicism for the audience? My working definition is Stoic doesn't control what happens, but they focus on how they respond to what happens. And the idea that the verges of Stoicism are courage, discipline, justice, and wisdom. So we try to respond with those things, the best of our abilities. How much are you an author? And how much are you like a psychiatrist to all of these people that come on your podcast? Uh, you know, it's surreal.

• 2:14Ryan Holiday?

  When I went to my publisher in 2012 and I said, I want to write a book about an obscure school of ancient philosophy. I'm not sure I envisioned any of this and certainly they didn't envision any of this. So it's been surreal to hear from military leaders and tech leaders and athletes and actors that this thing from so long ago could have so much relevance, particularly amongst elite performers.

• 2:39Speaker 01

  Do you feel like you live a stoical life?

• 2:41Ryan Holiday?

  Yeah, well, I'm certainly not writing the books from the perspective of having mastered these things and I'm explaining to you how easy they are. I'm writing about them first and foremost to myself because I need reminders of them as much as anyone else. I try to be stoic. I think I'm good at it, good at some of the stuff, not so good at the other stuff, but I'm working on it.

• 3:01Speaker 01

  What are you good at and what are you not good at?

• 3:03Ryan Holiday?

  You know, the discipline thing comes easier to me than courage or justice. I think I'm reasonably intelligent. I'm always trying to learn.

• 3:13Speaker 01

  But break those other pieces down, the justice piece and the courage piece, what that even means.

• 3:18Ryan Holiday?

  Yeah, so the cardinal virtues are courage, discipline, justice, wisdom. So, you know, courage is important, but in pursuit of what? Wisdom is important, but without the discipline, the strength to bring it into reality, what can you do? So these sort of interlocking virtues are what try to shape us as aspiring stoics.

• 3:40Speaker 01

  Have you found, I mean, you talk to athletes and you talk to CEOs and all sorts of other people. Do you find that there's one type of winner, if you will, that's better at this? I actually would think athletes would be because you have to go through pain.

• 3:53Ryan Holiday?

  Yeah, I think.

• 3:54Speaker 01

  And discipline and there's sort of, it's sort of, it's sort of such so physical.

• 3:58Ryan Holiday?

  Well, what's fascinating is, yeah, that what they all share in common is that at the elite level, it comes down to the mental side of things. So that, you know, you go into these locker rooms and what they're really thinking about is not the X's and O's or how to get 1% stronger, but how to bounce back from injuries, how to deal with, you know, things not going your way, how to deal with stress, how to find peace and stillness inside the craziness. To me, that's where the philosophy side of things really comes in. And that's what it was doing 2,000 years ago for a general or an emperor.

• 4:36Ryan Holiday?

  But anyways, I was surprised after to find out that Andrew Ross Sorkin, who is the co-host of the show, was a fan. And he and I sort of stayed in touch. We have some mutual friends. And I said, hey, if you're ever in Texas, I want to show you the bookstore and come do the podcast. And then it turned out he was going to be in Texas because he has a new book, which I loved, 1929 Inside the Greatest Crash in Wall Street History and How It Shattered a Nation, came out not too long ago, and it is a fantastic book. So he was here for the Texas Book Fest. I was doing something for them the following week, which I'll bring you something about that here shortly. But anyway, he was in town, so we came out to the studio and we had a lovely talk. And I think you're really going to like this episode.

• 5:21Ryan Holiday?

  In part one, Andrew talks about sort of the behind the scenes of the book, and we just sort of nerd out about writing and thinking and research. But in part two, he talked about something that I was fascinated to ask him about, like how he keeps his bearing when he's interviewing powerful people, talking about expertise, talking about putting a book out into the world and a bunch of other things. I think you're really going to like this episode. If you didn't hear my part one intro, Andrew is a financial columnist for The New York Times. He's the co-anchor of Squawk Box. He's the founder and editor of Dealbook. He wrote Too Big to Fail, which was not just a bestselling book, but a movie for HBO. And then he's the co-creator of Billions, if you haven't seen that show.

• 6:04Ryan Holiday?

  And his new book, 1929 Inside the Greatest Crash in Wall Street History and How It Shattered a Nation, is really, really good. He signed a bunch of copies at the Painted Porch. I think you should read it. And you can follow him on Instagram, @Sorkinsays, or on Twitter, @AndrewRSorkin. I'll just get into it.

• 6:27Speaker 01

  You've talked about procrastination on this, on the show before. I tell myself that procrastination is not really procrastination.

• 6:35Ryan Holiday?

  Okay.

• 6:36Speaker 01

  Meaning like even when you're tooling around the internet, looking at other things.

• 6:41Ryan Holiday?

  Sure.

• 6:41Speaker 01

  It may be a way of like creating a little bit of space in your brain to like then figure out the other thing.

• 6:47Ryan Holiday?

  For me, I'm like, did I make a positive contribution to the project today? I used to have this rule of like, and which I got from someone, which was like, like two crappy pages a day. Like that's what you did. But then I realized that was too focused on out on sort of tangible output, which is not always. Like when I look back at a book, I go, sure, obviously I wrote all these pages, but some of the best things were when I discovered connections between two things. Or I had an idea for something, or I thought I should go read about this person. So it's really like, just did I do something that moved the ball forward today? As long as I check that box, then you know, enough of those days eventually are done. So yes, it might be that you had two hours and you wasted an hour and 58 minutes of them.

• 7:30Ryan Holiday?

  But in the last two minutes, you were like, oh, you know what? This would be a good opening sentence for chapter 16.

• 7:36Speaker 01

  Totally.

• 7:36Ryan Holiday?

  And then that's moved the ball forward.

• 7:39Speaker 01

  Though, because I didn't really have a firm deadline, at least in the beginning, I think I was able to sort of take my time. When I wrote Too Big to Fail, which I literally started on, I think in November of 2008 and handed in the summer of 2009.

• 7:55Ryan Holiday?

  Yeah.

• 7:56Speaker 01

  And it was out by October. In fact, I think I had to have the draft done by June of 2009. I used to have on my, talk about blocking on the calendar. I used to have the number of words that had to be done every single day. I had sort of built a schedule where I think at minimum I had to really have about 800 words a day. And then there were certain days where I would just. Maybe the splattering we were talking about that was probably anchoring me to the wrong thing, but I would, you know, sometimes pound out like 3,000 words in a day. And then the problem was I then spend the next two days fixing them.

• 8:33Ryan Holiday?

  Yes, but you had a lot less going on then.

• 8:35Speaker 01

  I did have a lot less going on than I did was not involved in any kind of TV shows. I was writing my column for the New York Times and I was working hard on this book.

• 8:44Ryan Holiday?

  Yeah.

• 8:44Speaker 01

  And I took some time off too. I mean, from, and this I never really took real time off.

• 8:49Ryan Holiday?

  Yeah, it's like, sometimes the forcing function of it's coming out is exactly what you need. And then sometimes the, no, no, you should take as much time as you need.

• 8:57Speaker 01

  But I used to back then act like I was back in college. I would often write, I used to go to a bodega. I would get Tostitos and a six pack of Diet Coke and oftentimes a six pack of Corona beer. For some reason, I'll explain why this is not something that anybody should follow. And I would write from like 10 o'clock at night till five in the morning. I would, I would drink the Diet Coke to, to get myself up.

• 9:23Ryan Holiday?

  Yeah.

• 9:24Speaker 01

  And then I would start eating the chips and drinking the beer like four in the morning. Go to sleep from like five in the morning to like 11 in the morning. And maybe I'd show up at the office at noon. Maybe I'd stay at the office till like seven.

• 9:38Ryan Holiday?

  Yeah.

• 9:38Speaker 01

  Sort of a full day ish, and then go back home and do it all over again. It was very.

• 9:44Ryan Holiday?

  Did you just feel disgusting all the time?

• 9:46Speaker 01

  So disgusting. I felt so disgusting. I gained, everything was bad about it.

• 9:49Ryan Holiday?

  Yeah, it's funny how you do stuff like that and you're like, you're operating at some level of peak performance and then, then you like, you decide to take health seriously, you do something. And now it's like, you have a Diet Coke and you feel disgusting.

• 10:01Speaker 01

  Yes, completely. Oh, now I could never do that. I could never do that.

• 10:04Ryan Holiday?

  Yeah.

• 10:05Speaker 01

  I'm 48 now. I was 30, 30 years old then, 31.

• 10:09Ryan Holiday?

  I like, for instance, I used to write on airplanes and now if I sit on an airplane, I fall asleep. Like I can't, ever since I had kids, I'm like just running a sleep deficit all the time.

• 10:19Speaker 01

  Right.

• 10:19Ryan Holiday?

  And so I'm, I'm never like, oh, this, I'm like quiet time. This is, this is sleep time. So I never get any writing.

• 10:25Speaker 01

  Sleeper on a plane, but yeah, no, with health, I mean, by the way, you have, you have a book that I used to have called Abs Diet.

• 10:34Speaker 01

  There's a book right there.

• 10:35Ryan Holiday?

  It probably doesn't include.

• 10:36Speaker 01

  A Diet Coke.

• 10:37Ryan Holiday?

  Six Diet Cokes and.

• 10:38Speaker 01

  Yeah, it just, you can't do it anymore. You can't do it. You couldn't do it then either.

• 10:42Ryan Holiday?

  There is something about, like, if I'm, like, getting in the zone, I can eat an unlimited amount while I'm focusing.

• 10:48Speaker 01

  Yeah. Oh, for me, I could.

• 10:49Ryan Holiday?

  Or reading.

• 10:50Speaker 01

  Yes. The bad news for me is a weekend writing this book meant that I was just, like, living in the kitchen.

• 10:56Ryan Holiday?

  Yeah.

• 10:56Speaker 01

  I was trying to be good. I'd be eating, like, faillie yogurts and this and that. But then I was always looking for crunchy things, which is sort of a problem.

• 11:02Ryan Holiday?

  Yeah. Well, it's because you're not able to chain smoke, like, 200 cigarettes, which is, you know, like, that, that, there's probably something about that. It's just kind of there. So you're having to replace it. And, like, I think writers were meant to do that, and it's not good for you. So then you gotta, you have something.

• 11:20Speaker 01

  Can't drink and write. I know people who do that.

• 11:22Ryan Holiday?

  But what, what was the Corona?

• 11:24Speaker 01

  No, that was really just to go to sleep. Really, that was to, that was because the Diet Coke was so, I was five Diet Cokes in. I needed to stay awake. Now I need to go to sleep.

• 11:33Ryan Holiday?

  This is before children's melatonin?

• 11:35Speaker 01

  Before melatonin, yes. Now, now, now I'm a melatonin addict. I go, because I go to sleep early now.

• 11:40Ryan Holiday?

  Yeah.

• 11:41Speaker 01

  And I try to be asleep by 9:30, 10, because I gotta be up so early.

• 11:44Ryan Holiday?

  So one of the, one of the little things that pop up in the book that, it goes to one of my favorite books. Have you read this book, No More Champagne, about Churchill and his finances?

• 11:51Speaker 01

  And it's fabulous. And by the way, I use that as I cite it in the, in the end notes there.

• 11:57Ryan Holiday?

  Oh, I didn't know. I didn't read the end notes. But you mentioned Mitchell is, like, going to a dinner with Churchill.

• 12:02Speaker 01

  Yes.

• 12:02Ryan Holiday?

  But we tend to think of the depression or the, the, the market crash as this American thing.

• 12:07Speaker 01

  Yes.

• 12:07Ryan Holiday?

  As opposed to a thing that, like, had sucked in the entire world. Churchill, like Churchill being a great example of, of a rube who's, like, sucked into the market. And doesn't he, he gets, like, sucked into the market, and then he gets, like, hit by a cab in New York City all at the same time?

• 12:22Speaker 01

  Great story. No, I mean, the craziest part, Churchill, is he shows up in New York in October of 1929. Literally, he's on the floor of the stock exchange.

• 12:30Ryan Holiday?

  Yeah.

• 12:31Speaker 01

  As this whole thing is going down. He had come to New York, by the way, because he was out of money. And he came to the US to do a lecture tour to try to make some money, and then got bitten by this sort of speculative bug, like the rest of, you know, America, and starts trading like crazy. He's sending these letters back to his wife, asking for more money. He had met a broker for E. F. Hutton, who was advising him. And then, of course, he, he loses, he loses it all like everybody else. But interestingly, unlike. I think a lot of people in the US that sort of looked at this crash as a horrific thing, he looked at it completely differently. His reaction was America's sort of optimism, this sort of speculative nature of America was actually something that should be adopted more in the UK and elsewhere.

• 13:16Ryan Holiday?

  That you could make money, like new fortunes could be made.

• 13:19Speaker 01

  And that the great sort of attribute of America was its resilience.

• 13:24Ryan Holiday?

  Yeah.

• 13:24Speaker 01

  I don't think he appreciated that we're going to go through a decade plus long depression as a result of what had just happened. But yeah, he did not walk away scarred the way I think a lot of people did. He actually admired us for it. And then interestingly, comes back to New York just a little bit later. And he was supposed to have drinks at Bernard Baruch's house up on Fifth Avenue, maybe it's a Park Avenue, and he gets hit by a car.

• 13:49Ryan Holiday?

  Yeah.

• 13:49Speaker 01

  It's an amazing, amazing little story.

• 13:51Ryan Holiday?

  That's a metaphor there. He gets hit by a New York City cat crossing the street.

• 13:54Speaker 01

  Exactly.

• 13:56Ryan Holiday?

  Yeah, there's, the way that smart people get sucked into it is fascinating to me. Like you have churn out blurbs of book, like that's the most fascinating part.

• 14:05Speaker 01

  Which by the way, I almost cried when he decided to do that. I mean, that was beyond.

• 14:09Ryan Holiday?

  So I did cry. So he was here and did you, I'll send you a link.

• 14:12Speaker 01

  I've seen it. I've watched it.

• 14:13Ryan Holiday?

  Did you see my son talking to him? So my nine year old is obsessed with Hamilton. And so we like let him come out of school. He got like late.

• 14:22Speaker 01

  I just saw him on your show talking about Mark Twain.

• 14:24Ryan Holiday?

  Yeah. At the end, basically my nine year old like kicks this door open and he's like, I have some questions. And he sits here and he asks him a bunch of Hamilton questions.

• 14:31Speaker 01

  I did not see this.

• 14:31Ryan Holiday?

  It's very funny. There's a part in it where he's, they're singing the first song of Hamilton together. And my son, I can't quite wrap his head around how insane like the experience is, but I was sitting right there. It was nuts. But the craziest parts of the Mark Twain thing are you're watching this guy who's making an ungodly amount of money as a writer, get caught up in the sort of mania of his time. It's never enough. And he can't restrain himself and he makes and loses several fortunes as an investor.

• 15:05Speaker 01

  But isn't that ultimately the lesson of all of us? Isn't that

• 15:08Ryan Holiday?

  Yeah.

• 15:09Speaker 01

  the problem with, I don't know if it's a problem. By the way, it may actually be a good thing with humanity. We all want. More, I mean, some people call that greed.

• 15:18Ryan Holiday?

  I mean, I was curious, like, I think it's because Mark Twain becomes so famous. His peers are suddenly not writers, so he's not competing like who's getting the most royalties. It's he knows all these titans of industry and the inherent keeping up with the Joneses. He realizes like, oh, no, no, no, making a lot of money from the sales of Huckleberry Finn. You gotta invent a company, you gotta go public, you gotta, you know, speculate in stocks. It must be interesting for you, I mean, you're around talking to some of the richest, most successful people in the world. How do you keep your bearings?

• 15:53Speaker 01

  Well, look, how do I keep my bearings?

• 15:54Ryan Holiday?

  How do you keep your eyes on your own paper, like, literally and figuratively, you know? Like, how do you, how do you go, I'm doing my thing, we're running different races?

• 16:01Speaker 01

  So a combination of things are going on. One is we are running different races.

• 16:04Ryan Holiday?

  Yeah.

• 16:05Speaker 01

  And I acknowledge we're running different races. I tell myself we're running different races. I know that I'm not going to be running a race that lands me on a private plane, flying to wherever with a bajillion homes. It's just not, for better or worse, it's not in the cards.

• 16:21Ryan Holiday?

  Yeah.

• 16:22Speaker 01

  I feel like I'm running my own race. My, my own race is, is working out frankly, better than I ever thought it was supposed to. So I'm, I'm pretty pleased with it. But yeah, I'm sure there's an element of me, but I think it's, this was probably the human part of it, which is, this is why I was saying we were all trying to fill a hole.

• 16:37Ryan Holiday?

  Yeah.

• 16:38Speaker 01

  Like, yeah, can you ever be enough, have enough, is it enough? You know, there's this great clip of Jim Carrey, have you ever seen this clip?

• 16:46Ryan Holiday?

  This is about the wants everyone to be rich?

• 16:48Speaker 01

  No, it's, it, he's winning a Golden Globe.

• 16:51Ryan Holiday?

  Yeah.

• 16:51Speaker 01

  And he talks about, is it enough? Like, he's maybe one or two times or something, is he enough?

• 16:58Ryan Holiday?

  Yeah.

• 16:58Speaker 01

  And I think that's a question that everybody asks themselves all the time, like, is it enough? When's it enough? By the way, I'm somebody who's probably always trying to find the next thing.

• 17:08Ryan Holiday?

  Yeah.

• 17:09Speaker 01

  Right? Like, I have to think that's probably why I'm, part of writing that book was because I was curious about the topic and part of it was like, Can I prove to myself that I can actually do this?

• 17:18Ryan Holiday?

  Yeah.

• 17:19Speaker 01

  There are other people. My wife is the opposite of me. She is the most content person. She is not somebody who's like professionally, she wants, she wants to do more and more, but she really is like a very grounded person.

• 17:32Ryan Holiday?

  It's kind of aggravating, isn't it? When you realize you're like, you're just good. Like that, it feels almost like unfair or almost feels like it's like threatening because they're like, I don't.

• 17:42Speaker 01

  She's, she's cool.

• 17:43Ryan Holiday?

  Doesn't matter to me at all.

• 17:44Speaker 01

  For her, it's like, it's all going to come out of the wash.

• 17:46Ryan Holiday?

  Yeah.

• 17:47Speaker 01

  You know, I always say I'm worrying so she doesn't have to.

• 17:51Ryan Holiday?

  Yeah. The best enough story is, and I think it's in the guy who wrote the Vanguard guy's book. He wrote a book about the idea of having enough, but Joseph Heller and Kurt Vonnegut are at a, some finance billionaire's house in New York City. And Vonnegut is teasing Heller and he says, you know, this guy made this week more than all of the sales of Catch 22. How does that make you feel? And he's like, I don't care at all. And he's like, what do you mean you don't care? And he says, you know, I have something this guy doesn't have. And, and Vonnegut says, what could that possibly be? And he says, I have enough.

• 18:25Speaker 01

  Right.

• 18:25Ryan Holiday?

  Which is a pretty powerful.

• 18:26Speaker 01

  But do you think most people feel that way? Do they feel like they have enough?

• 18:30Ryan Holiday?

  No, I think it's an exceedingly rare thing. And I imagine Heller, I mean, Heller wrote one of the greatest books of all time. He didn't go like, he didn't pull a Harper Lee and just stop. Clearly he didn't have enough.

• 18:43Speaker 01

  Right.

• 18:43Ryan Holiday?

  It's probably not financially, but there's something he was trying to do or make or prove. I think it's just money is a bad one to never have enough of.

• 18:52Speaker 01

  You ever seen the movie Wall Street 2?

• 18:54Ryan Holiday?

  No.

• 18:54Speaker 01

  Okay. Not nearly as good as Wall Street 1. And there's a scene in the movie where I think Shia LaBeouf says to Josh Brolin, what's your number?

• 19:05Ryan Holiday?

  Yeah.

• 19:05Speaker 01

  Like, what's your number? Like where you'd feel like financially dependent or like, it would be enough. Basically top of the mountain. What's the number that would let you feel like you could ski down the mountain and be done? And he looks back at him and he goes, more.

• 19:21Ryan Holiday?

  I had a very revealing conversation with someone. I'll tell you who it is off there, but they'd written a couple of books. They'd done really well and they decided to go into investing instead. And I was like, why? Like, I was like, so you're raising this fund, you know, I was curious about it. And they were walking me through the math, you know, it's like two and 20. So, so I was like, okay, so let's say, you know, this fund goes to X and you walk away with $50 million or $100 million, which would be the bet. I was like, what are you gonna do? And he was like, he was like, do you know who Alain de Batton is, you know, the philosopher? And I was like, yeah. And he's like, well, he has this thing. He was basically like, he wanted to be this philosopher. And it was like, you could, you're doing that right now. Like, he didn't make $100 million in the hedge

• 20:06Ryan Holiday?

  fund business before he became a philosopher. He just did it. And so it was, it was hilarious. It was literally embodiment of that famous, there's that famous story about like the, the fisherman on some island, right? Which actually, by the way, people don't know, that story dates back to like the 15th century, and it's an advisor talking to a king. The king has to conquer Europe so he can live in peace.

• 20:29Speaker 01

  Oh, I didn't know that.

• 20:29Ryan Holiday?

  And he's art, like, he's in peace. He has to conquer Europe so he can live in peace. I watched someone with no awareness tell me that they needed to go make tens of millions, a writer needed to go make tens of millions of dollars so then they could go back to being a writer. And I thought that's like the craziness of it right there.

• 20:59Speaker 01

  I had a question for you, because you've written a lot of books.

• 21:01Ryan Holiday?

  Yeah.

• 21:02Speaker 01

  And I was actually discussing this with my wife just a couple of days ago, talking about enough.

• 21:06Ryan Holiday?

  Yeah.

• 21:06Speaker 01

  Or whatever that even means these days. When you've finished the book, and the book's out in the wild, people get to see the book and read the book. Do you feel enough? Do you feel great satisfaction? Do you feel great euphoria? Or something else?

• 21:27Ryan Holiday?

  So two, two thoughts there. So number one is I have come to realize that my job is to write. That's

• 21:37Speaker 01

  Euphoria is in the, is in the journey.

• 21:39Ryan Holiday?

  Yes, like I've, I've been saying like, I'm, I'm no longer, I'm very ambitious as a writer, but I'm not ambitious as an author. Like, I just don't, I don't think about the other things as much anymore, which I think has been wonderful and rewarding in that like, I love what I'm doing. Like I was, I told my wife the other day, like, I was like, I'm loving this thing I'm working on right now. I'm like, why am I, I'm not going to rush through it. I'm just going to let it take as long as it takes. Cause actually the worst part is at the end. And she's like, oh, that's very interesting. And then I would say the only downside to that is that it makes the launch thing, which there is some part of you that always wants and thinks it's going to be rewarding, to be much more anticlimactic. Like the wisdom book came out in, on the 21st of October.

• 22:24Ryan Holiday?

  And I, I honestly, I don't know what anyone thinks of it. Like, because I, I don't check reviews anymore. People can't send me emails about it.

• 22:32Speaker 01

  You don't check reviews?

• 22:34Ryan Holiday?

  No. Well, my books tend not to be reviewed by publications.

• 22:38Speaker 01

  Okay.

• 22:38Ryan Holiday?

  So like every once in a while, they, I think I've had maybe one book reviewed in the times. But for the most part, I'm not getting critical reviews. I'm getting like random people on Amazon or whatever. I was like, I'm not going to work for six years on something and let some random ass person.

• 22:53Speaker 01

  Good for you.

• 22:54Ryan Holiday?

  So that requires not checking, but that also just means I just, let's say they all got stolen before it, they came out. I like, wouldn't know, you know? And that, that's a little weird. Like I've got to find some slight middle ground where I would like just a little bit of information that like, right, it's out, it did okay. But I, I try to focus on the part of it that I control, which is everything up until launch day.

• 23:17Speaker 01

  So I was going to say that I thought I was going to feel a sense of euphoria, actually, when the book came out. And the truth is, I just felt a sense of relief.

• 23:28Ryan Holiday?

  Yeah.

• 23:29Speaker 01

  Which is weird.

• 23:30Ryan Holiday?

  Yeah.

• 23:31Speaker 01

  But I do think now, retroactively, again, I don't know if my family feels the same way, whether I was euphoric the whole time I was working on it. I think I really did enjoy it, even though it probably looked and did feel painful and I complained about it.

• 23:45Ryan Holiday?

  Yeah, like the euphoria was the day you discovered that document in the library. That that part was was yours and yours alone and no one can take it away. And then, yeah, how it what the list says or what the rewards say or what, you know, when you get nominated or not nominated, those are all goals that are not up to you and worth maybe not thinking about so much. But you did do it for someone other than yourself. So you do want to make sure, hey, it landed.

• 24:10Speaker 01

  I am not a stoic. I wish I was. I wish I was.

• 24:13Ryan Holiday?

  I'm only aspiring to be one, but I remember on my first book, the week. So, you know, for people don't know, the books come out on a two, all books, all traditional books come out on Tuesday.

• 24:24Speaker 01

  Should we pause?

• 24:26Ryan Holiday?

  For people don't know, they're making a lemonade outside.

• 24:29Speaker 01

  Is that what that is?

• 24:30Ryan Holiday?

  Yeah. So, so this shop is weird, right? Because like, we're taking it off the real, like, Main Street real estate. So I feel kind of bad. Like, I don't want to like, kill the town.

• 24:40Speaker 01

  Right.

• 24:40Ryan Holiday?

  So we let people set up shop. Like, when they have these festivals, we let them. But then sometimes we do stuff and it's very loud and they're going through a cooler to get the ice for the lemonade. But what was I saying?

• 24:50Speaker 01

  You were saying, what you were saying was that books come out on Tuesday.

• 24:53Ryan Holiday?

  Oh, yeah. Books come out on Tuesday. And so it's basically all the preorders before Tuesday to Sunday, and then you find out the subsequent Wednesday, whether you hit the list or not. And then there used to be the Wall Street Journalist, which would come out on Friday.

• 25:06Speaker 01

  Right.

• 25:06Ryan Holiday?

  And so that period after the book was done, but before the news, that was one of the shittiest weeks of my life.

• 25:14Speaker 01

  Yes.

• 25:15Ryan Holiday?

  And when I did find out that my first book had hit the list, not the Times, the Washington Journal one, I wasn't like, proud. I was, all I felt was relief because I'd so tortured myself leading up to it. And this wasn't a overnight transformation, but I just realized that's a really shitty way to live your life. And I I feel like I've over time flipped. If I was 90% waiting to hear the news and 10% like, I can't believe I got to put out my first book. I'm like 90%, I did this, I'm proud, I'm happy I got to do it.

• 25:49Speaker 01

  Okay, so you have a lot of authors who come through this beautiful book story that you've created here. Sometimes first time authors, sometimes multi-

• 25:56Ryan Holiday?

  Yeah.

• 25:57Speaker 01

  -book authors. Do you think most of them feel this way?

• 26:00Ryan Holiday?

  Probably not. It's all, I mean, and I don't feel that way all the time. It takes work. But I remember when Chernow was in here, that was the week a really shitty review in the Times came out.

• 26:08Speaker 01

  Right.

• 26:08Ryan Holiday?

  And so should he, should Dwight Garner get to decide that Ron Chernow, who wrote a thousand-page, epically researched, riveting biography of one of the greatest authors of all time, should he get to decide how he feels about that whole process? That's just like a, there's no way that makes sense.

• 26:28Speaker 01

  I don't disagree with you at all.

• 26:29Ryan Holiday?

  The Marcus Aurelius line is, "We all love ourselves more than other people, but for some reason, we care about their opinions more than our own." It's like, they're paying you to do it. You're the one. And then you're like, but tell me if I did it or not. And it's like, it can't work that way.

• 26:43Speaker 01

  Oh, I love that.

• 26:44Ryan Holiday?

  Is your wife your book agent?

• 26:45Speaker 01

  She is not. She is a, she is a literary agent, but she is not mine. I always thought that would prove to be too complicated.

• 26:52Ryan Holiday?

  Yeah, I was curious about that.

• 26:54Speaker 01

  Conflict-y kind of perspective.

• 26:56Ryan Holiday?

  A conflict of interest or a conflict of just cause conflict?

• 27:00Speaker 01

  It's just, you know, sometimes the agents have to call the publisher or the editor and ask them to do things that they don't want to do, whatever that is. And I just thought, you know, better to have somebody else do that.

• 27:11Ryan Holiday?

  Yeah, it's like, I want to be able to, like, you call your agent and then you don't care what they have to tell the publisher to get, you could, they could be like, Ryan's being a little bitch right now.

• 27:19Speaker 01

  Yes.

• 27:20Ryan Holiday?

  But can you just do this to make him happy? You don't want to, you don't want to overhear that your wife did that. You want, you want the plausible deniability that you are taken seriously.

• 27:28Speaker 01

  That's what I, that's what I tell myself.

• 27:30Ryan Holiday?

  Does she read your work or do you guys exist in different literary worlds?

• 27:33Speaker 01

  We live in almost like parallel universes. I did not really even let her read the book until I was pretty much done. I just felt like it was better not to.

• 27:44Ryan Holiday?

  Yeah, it's weird because you obviously care about this person's opinion more than basically anyone else's opinion. And maybe that's why you're like, let's not even get into it.

• 27:55Speaker 01

  Yeah. By the way, she had some good suggestions. I made, I made the changes and I was happy that she liked it.

• 28:01Ryan Holiday?

  My problem is I've written too many books. It's just too much to ask any one person to have read all of that. Do you know, like, if someone came up to me and they said, I've read literally every book you've written, I'd be like,

• 28:11Speaker 01

  Does your wife read everything?

• 28:12Ryan Holiday?

  Well, that's what I'm saying. Like, early on, I was like, you gotta read that. Like, you're hurting my feelings. You're not reading this. And then I'm like, 16 books is a lot to ask one person to read about, even if it's over a long period of time. You're just tired of this.

• 28:25Speaker 01

  I only got her to subscribe to the Deal Book newsletter a couple of years ago.

• 28:29Ryan Holiday?

  Just to save, save like, so she's vaguely aware of what you're working on?

• 28:33Speaker 01

  Yeah, I just, I, I actually thought that she used to get the newsletter and that she was like up on, because she'd always be talking to me and she'd know what I was working on.

• 28:40Ryan Holiday?

  Yeah.

• 28:40Speaker 01

  And then I discovered that she didn't read it.

• 28:44Ryan Holiday?

  Did that hurt your feelings?

• 28:45Speaker 01

  Of course it did. Now, now she opens it every day to hopefully increase the open rate.

• 28:50Ryan Holiday?

  Yes, yes. That's funny. Mark Twain's obviously the great, a good example if someone gets caught up in it. But the most tragic example, I think, in American history is, is, is Grant. Alyssa S. Grant.

• 29:00Speaker 01

  Yeah.

• 29:01Ryan Holiday?

  Just had no business being in the market and just gets eaten alive by it.

• 29:05Speaker 01

  Look, most of us have no business, not being in the market, but being stock pickers. It is very, it's just a very, very hard business. And it's why Warren Buffett famously tells his family members,

• 29:17Ryan Holiday?

  Yeah.

• 29:18Speaker 01

  just buy an index.

• 29:20Ryan Holiday?

  Right.

• 29:20Speaker 01

  Close your eyes and look up a decade later and you should be in better shape.

• 29:26Ryan Holiday?

  There's a famous Sherman quote, because it, so for people that know, Grant, after the war and then after the presidency, he not just like gets invested in the market, he like opens a brokerage house.

• 29:38Speaker 01

  Oh, yeah. No, he gets totally engaged.

• 29:39Ryan Holiday?

  And is basically this guy stealing money and speculating wildly. He loses everything. And Sherman was saying how tragic it was that this dude, who, he said, like, these Wall Street financiers would

• 29:54Ryan Holiday?

  Given every penny they had to have won just one of his battles. And Grant is like trying to compete with them to do what they do. And that's why you get the hubris of being like, hey, I'm good at like for Mark Twain. It's like, hey, I know I'm one of the greatest authors of all time, but I should also be a great financier, investor, inventor. That's where you get yourself in trouble, I think, that the

• 30:18Speaker 01

  But that's also But that's also human nature. You people have success in one thing. By the way, this is true of all of the, you know, CEOs and politicians in the world and other people. You get to the top of the mountain and then they think to themselves, I can do this, this, this and this. And I can do it as well, if not better than everybody else. Because somehow these skills are, you know, completely transferable. And of course, most of the time they're not.

• 30:41Ryan Holiday?

  Yes, I think it's like, who's the, who's the investor that desperately wants to be an author? The algorithm hedge fund guy, what's his name?

• 30:50Speaker 01

  Algorithm hedge fund guy.

• 30:52Ryan Holiday?

  Ray Dalio. Ray Dalio.

• 30:53Speaker 01

  Yeah.

• 30:54Ryan Holiday?

  Yeah, it's like you have all the money in the world. You run this huge company, but he seems to want to be a thought leader more than.

• 30:59Speaker 01

  Well, I think in retirement now, he's trying to figure out what the, the next thing is.

• 31:03Ryan Holiday?

  Yeah.

• 31:04Speaker 01

  And he, he wants to be a writer.

• 31:06Ryan Holiday?

  Yeah, the idea that domain expertise is transferable is fascinating because sometimes it is. And sometimes it's not. Obviously you see this a lot, like people make a lot of money in one industry and then they think they can crack Hollywood.

• 31:19Speaker 01

  Right.

• 31:19Ryan Holiday?

  That doesn't work or they made a lot of money, had a lot of success and they think, well, I'll do politics now.

• 31:26Speaker 01

  Right.

• 31:26Ryan Holiday?

  And that doesn't always work.

• 31:39Speaker 01

  By the way, I was going to say, there's a character in this book, John Raskov.

• 31:43Ryan Holiday?

  Yeah.

• 31:44Speaker 01

  Sometimes it works and sometimes it doesn't. He was like the Elon Musk of it all. And there are these people, these sort of singular talents that somehow are able to sort of apply their logic over like everything.

• 31:55Ryan Holiday?

  Yeah.

• 31:56Speaker 01

  And he did that. He was running General Motors. He ends up becoming sort of a

• 32:00Ryan Holiday?

  Head of the DNC, basically?

• 32:01Speaker 01

  He runs the DNC, by the way, switches from being a Republican to a Democrat. He then ends up building the Empire State Building. He is to some degree responsible for the fact that we have a five day work week. He was also like a philosopher king.

• 32:15Ryan Holiday?

  Huh.

• 32:16Speaker 01

  What he thought in the fall of 1929, he had this idea not to be nice to everybody. Back then, we worked on Saturdays.

• 32:24Ryan Holiday?

  Yeah.

• 32:25Speaker 01

  He thought that if we had two days off, you could create a much bigger consumer economy. More people would buy cars because they'd have two days to go places. They'd buy gardening equipment, they'd buy different outfits.

• 32:37Ryan Holiday?

  Yeah.

• 32:38Speaker 01

  All of the things.

• 32:39Ryan Holiday?

  Yeah.

• 32:39Speaker 01

  All of the things. He wrote a paper about it, actually in the middle of the crash. So there are some people who do have these sort of like outsized ideas and approaches that that can work sometimes, but most don't.

• 32:52Ryan Holiday?

  Well, and the tricky thing is being great in one thing and then you go to another thing. And then that, if it does transfer, that's almost like the most dangerous. Because now you believe you're the Renaissance man who can do anything and everything. And it's statistically inevitable that you will find the thing that you actually can't do.

• 33:14Speaker 01

  Okay, so how do you feel about that in the context of writing? And I thought about that a lot. So I had never written anything that was but history.

• 33:21Ryan Holiday?

  Yeah.

• 33:21Speaker 01

  Right, I'd always written about sort of modern stuff, almost in the moment. And for me, this was like a stretch goal.

• 33:30Ryan Holiday?

  Yeah.

• 33:30Speaker 01

  Kind of thing, because I thought, can I apply these things?

• 33:33Ryan Holiday?

  Yeah.

• 33:34Speaker 01

  And, you know, I have friends who do journalism or write nonfiction books who have ambitions to write novels.

• 33:42Ryan Holiday?

  Yeah, I usually get nervous when my friends tell me they're working on a novel. It's usually a sign of like, something's going on at home. And there's some forces swirling about and it usually tends not to go well. But yeah, like, how do you know when it is a stretch goal and when it's delusional? That's a fine line. And sometimes, I guess, the results tell you the answer.

• 34:05Speaker 01

  Right.

• 34:06Ryan Holiday?

  But sometimes the result telling you the answer doesn't mean that it wasn't insane. Like, you make the huge bet, like, some of the characters, I think, in the book, and then obviously in financial history, it's like, they made a totally reckless, insane bet that statistically sometimes pays off. And when it does, do they learn the lesson that they like, they just played Russian roulette and didn't die? Or do they emerge from that going like, no, no, no, I know in my gut when it's crazy or not? So like the, let's say you decided to write a novel and, and then it somehow worked. Doesn't necessarily mean it was a good idea.

• 34:43Speaker 01

  Right.

• 34:43Ryan Holiday?

  Because it could have been.

• 34:44Speaker 01

  Could have been a terrible idea.

• 34:45Ryan Holiday?

  Yes.

• 34:46Speaker 01

  But that's the thing about everything, right? And then, but this goes back to what is actually satisfying to you.

• 34:51Ryan Holiday?

  Yeah.

• 34:51Speaker 01

  Meaning where's the euphoria come from?

• 34:53Ryan Holiday?

  Sure.

• 34:53Speaker 01

  If the euphoria comes from writing the novel.

• 34:56Ryan Holiday?

  Maybe, yeah. But are you writing the novel because you want to write a novel? Or are you writing the novel because you want to be a novelist?

• 35:01Speaker 01

  Right. All good questions and depends.

• 35:04Ryan Holiday?

  Like it would be very, it would be, I'm sympathetic to it as often as I am critical to, critical of him. It would be very difficult to be Elon Musk and know what's a good idea and a bad idea. At this point in his life and career.

• 35:18Speaker 01

  No, and especially when you're told that you're wrong all the time.

• 35:21Ryan Holiday?

  Yes.

• 35:21Speaker 01

  And then you seem to be able to shoot the moon and win.

• 35:26Ryan Holiday?

  Yeah.

• 35:26Speaker 01

  Yeah, I actually think it would be very hard to actually be able to tell yourself that you're wrong.

• 35:31Ryan Holiday?

  Well, Peter Thiel said, if you were writing a book about Elon Musk, it would be titled The Man Who Knows Nothing About Risk.

• 35:37Speaker 01

  Yeah.

• 35:38Ryan Holiday?

  Because he just takes, he goes all in all the time and then doesn't die. And how do you walk around not feeling like you're invincible? When?

• 35:51Speaker 01

  Yeah.

• 35:51Ryan Holiday?

  Like, but the Midas touch story is a cautionary tale. Like it doesn't, it sucks to be King Midas.

• 35:57Speaker 01

  Well, it can be lonely too.

• 35:59Ryan Holiday?

  Yeah.

• 35:59Speaker 01

  Yeah.

• 35:59Ryan Holiday?

  Right. So yeah, how do you, how do you stay in touch with reality? When you are, when you have what Steve Jobs called the reality distortion field? And that's kind of what makes you do what you do. That, that would be a very tricky balance.

• 36:15Speaker 01

  I think it's, it's a particularly tricky balance if you're, if you're Elon Musk. I think it's a tricky balance, by the way, given that I cover a lot of wealthy people back in the 1920s. In the 1920s, I think it was difficult. I think it's difficult for them today. It's not that I have great sympathy for them.

• 36:29Ryan Holiday?

  Yeah.

• 36:30Speaker 01

  In this regard, but I do think that when you sort of live in a cloistered world.

• 36:35Ryan Holiday?

  Yeah.

• 36:35Speaker 01

  Where a lot of things just get done for you.

• 36:38Ryan Holiday?

  Yeah.

• 36:39Speaker 01

  It's hard to, this is where I have, I guess, maybe it's not sympathy, but empathy. Like, I understand why sometimes that lack of either curiosity or understanding of some of the other things that are happening in the world are sort of lost on people.

• 36:54Ryan Holiday?

  Yeah, I think I find they get used to sitting around at dinners pontificating and there's no longer any intellectual give and take. It's just, we're listening to the genius or to the guru. And then sometimes they'll say the things that they've been pontificating about in public and people are like, what the fuck are you talking about? It's suddenly subjected to market forces in the way that in their personal and private life, it no longer is.

• 37:20Speaker 01

  So sometimes I tell myself, when that happens, in my approach of like trying to put myself in their shoes, either they're just delusional.

• 37:28Ryan Holiday?

  Yeah.

• 37:29Speaker 01

  And that's the answer. Or I tell myself, part of the problem is that professionally, they get put in a situation where they're just being asked questions all the time.

• 37:38Ryan Holiday?

  Oh, yeah.

• 37:38Speaker 01

  And they just get so used to

• 37:40Ryan Holiday?

  Yes.

• 37:41Speaker 01

  being asked the question and thinking that it is, that they, they're like a wind-up toy and they're supposed to now pontificate. Like, that's what they're supposed to do.

• 37:48Ryan Holiday?

  Yeah.

• 37:48Speaker 01

  And so they do that.

• 37:50Ryan Holiday?

  Yeah, no, I think podcasting is dangerous in that regard, too. You, you don't say, I don't know. You never say, I don't know, whatever, I don't care, haven't thought that much about it. You have to answer. And so you get used to just pulling stuff out of your ass and you say it enough times and it starts to feel like it has something to it and it's, it's just nonsense. Did you, have you read?

• 38:15Speaker 01

  I feel like, I feel like that's getting clipped, by the way, for the gram.

• 38:18Ryan Holiday?

  Maybe. Well, have you read Mark Twain's letter to Vanderbilt?

• 38:22Speaker 01

  I don't know if I have.

• 38:23Ryan Holiday?

  He famously writes this letter to Vanderbilt and he says, "You don't understand that some of your ideas have no inherent significance or genius. They are just reflecting the glitter of your 70 millions." Because that was his fort-

• 38:37Speaker 01

  Right.

• 38:37Ryan Holiday?

  He was just saying that, like, you think you're a genius, but you're, it's, it's the halo effect, which obviously wasn't a term then, but that it just seems true because everyone around you is saying it's true. Like the, you know, the emperor's new clothes and you're not, you don't live in reality anymore. And this is the, the fundamental peril of, of that level of success and inequality is that it can't help but corrode and change your perception of reality. It's a fascinating letter.

• 39:10Speaker 01

  I get it.

• 39:11Ryan Holiday?

  Which he then falls prey to himself.

• 39:13Speaker 01

  Of course.

• 39:13Ryan Holiday?

  As an inventor.

• 39:14Speaker 01

  Of course.

• 39:15Ryan Holiday?

  I mean, he was wealthy, but not even close to what wealth is conceivable now.

• 39:21Speaker 01

  What year was that?

• 39:22Ryan Holiday?

  I don't know. When, when does?

• 39:25Speaker 01

  Seventy billion, seventy million, you said?

• 39:26Ryan Holiday?

  Yeah. Late eighteen hundreds.

• 39:28Speaker 01

  Seventy million was still a lot of money in.

• 39:30Ryan Holiday?

  No, it's a lot of money, but it's just, uh, you know, it's not a trillion dollar.

• 39:34Speaker 01

  Right.

• 39:35Ryan Holiday?

  Pay package.

• 39:36Speaker 01

  Our first billionaire was Rockefeller.

• 39:39Ryan Holiday?

  Yeah.

• 39:40Speaker 01

  Our second billionaire, by the way, there was an article in nineteen twenty nine. The headline was our second billionaire.

• 39:46Ryan Holiday?

  You quote that in the book. It's Ford, right?

• 39:47Speaker 01

  Henry Ford. Yeah. Non-inflation adjusted. I often think about those characters because I'm often thinking about, you know, how much money is, you know, yes, a trillion dollars, a whole nother.

• 39:56Ryan Holiday?

  Yeah.

• 39:57Speaker 01

  Whole nother level.

• 39:58Ryan Holiday?

  Also, what could money buy you then? It's like, okay, it gets you a, gets you a nicer train car, but you can't control how fast the train is going. But now you could buy a jet to fly over the world or you could buy, the amount of money and what can be purchased with it is like.

• 40:13Speaker 01

  Is different.

• 40:14Ryan Holiday?

  You take the emperor of Rome two thousand years ago and it's like, sure, this is incredible past, these other things, but it's still, it's fucking cold during the winter and.

• 40:24Speaker 01

  Okay. I don't know if I should share this story with you though, because now you're making me think about a billionaire who once said to me, Andrew, once you get to about five or six hundred million dollars, there's nothing that makes me different than.

• 40:40Speaker 01

  The guy who's got $20 billion or $100 billion.

• 40:43Ryan Holiday?

  Right.

• 40:43Speaker 01

  This goes to your, you know, you can only make the train go so fast.

• 40:46Ryan Holiday?

  Yes.

• 40:48Speaker 01

  And I said, okay, break it down for me. Why is 500? What's 500 million? He said, well, once you have the plane and you have two or three homes, said, maybe if there's some art and the staff, it's like, there's not much else that you can do.

• 41:02Ryan Holiday?

  Right.

• 41:03Speaker 01

  He said, you could have a boat. He said, a boat.

• 41:05Ryan Holiday?

  Oh, a super yacht.

• 41:06Speaker 01

  A super yacht. He said, that's, that's maybe in a different league.

• 41:09Ryan Holiday?

  Yeah.

• 41:10Speaker 01

  I mean, I remember that conversation sort of walking away on, huh?

• 41:12Ryan Holiday?

  Well, I remember there was some reporting about Jeff Bezos's wedding and they were saying like, he was going to spend this much. And I remember I saw an article where, where Bill Ackman was saying, it's not possible to spend that much on a wedding. Like, the reporting was wrong.

• 41:25Speaker 01

  Right.

• 41:25Ryan Holiday?

  He knew because you could, you can't actually spend $500 million on a wedding. And you go, oh yeah, at some level, there's actually just like some ceiling of like what it is possible to spend on.

• 41:38Speaker 01

  Right.

• 41:38Ryan Holiday?

  And yet, there's some human compulsion to go beyond that money. Well, you've probably met, you go to your point about the number.

• 41:45Speaker 01

  Right.

• 41:45Ryan Holiday?

  How many people get to that number and then the number changes?

• 41:50Speaker 01

  Oh, I think for almost everybody, the number changes.

• 41:52Ryan Holiday?

  Yeah.

• 41:53Speaker 01

  By the way, even for myself, I remember, you know, I was 20 or 25, thinking, you know, what would it take to feel?

• 42:00Ryan Holiday?

  I wanted to write a book. I thought that would be a like.

• 42:03Speaker 01

  That would do it.

• 42:03Ryan Holiday?

  That's it. I wrote, that's the goal.

• 42:05Speaker 01

  Touch the base, I'm done.

• 42:06Ryan Holiday?

  Yeah.

• 42:07Speaker 01

  Right.

• 42:08Ryan Holiday?

  And then you're like, let's do the next one.

• 42:09Speaker 01

  Exactly.

• 42:10Ryan Holiday?

  You can't stop.

• 42:11Speaker 01

  But I do think, and maybe this is Winston Churchill's point, that's what makes our society actually work. Meaning that people do have this drive.

• 42:21Ryan Holiday?

  Yeah.

• 42:22Speaker 01

  And maybe it's a drive for more. And I know it can go, it can be too much, but it is the thing that sort of propels everything.

• 42:28Ryan Holiday?

  Well, from an evolutionary standpoint, it makes sense. And from a societal and economic sense, it's probably the least bad of this. Like, it's better to harness that force.

• 42:39Speaker 01

  Right.

• 42:39Ryan Holiday?

  To innovate and create and make a forward moving society than to try to, you know, like throw those people in gulags and make them not want.

• 42:48Speaker 01

  Right.

• 42:48Ryan Holiday?

  To succeed anymore. That doesn't mean it's good for the individual who never has enough, right?

• 42:54Speaker 01

  Totally. Yeah.

• 42:55Ryan Holiday?

  There are these two, it's these two contradictory ideas that you have to hold in your head at the same time, which is like our ceaseless desire for more and. Wanting to know what's on the other side of the hill and the grass is greener, blah, blah, blah. That's what propels humans from where we were even 30 years ago, 50 years ago, 100 years ago. And then if you don't figure out some way to turn that off or turn it down, you'll end up in ruin.

• 43:20Speaker 01

  But I will also say, we've been lucky in that you could argue we're either high performers or good things have happened. There are a lot of people today that think they want more, but they think that they can't get more, meaning that the system unto itself just doesn't work.

• 43:34Ryan Holiday?

  Yes.

• 43:34Speaker 01

  By the way, there were people, obviously in the late 20s or 30s, when there was 25% unemployment, who thought that there, you know, it was an oppressive society. I mean, you could even argue politically right now, in parts of our country, there's questions about

• 43:46Ryan Holiday?

  Sure.

• 43:47Speaker 01

  whether this sort of more and more capitalistic world even works at all. And then this is, I live in New York City where we have a democratic socialist.

• 43:54Ryan Holiday?

  If you're 25, what have you seen the system do well in your lifetime?

• 43:58Speaker 01

  Right. No, and that's, and that's a fundamental question in terms of like,

• 44:02Ryan Holiday?

  Sure.

• 44:02Speaker 01

  what we're talking about in a way.

• 44:04Ryan Holiday?

  Yeah, yeah, of course. You want to check out some books?

• 44:06Speaker 01

  I'd love to.

• 44:06Ryan Holiday?

  Let's do it.

• 44:13Ryan Holiday?

  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.