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

Episode Date: December 6, 2025

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, a financial news service published by The New York Times. He wrote the bestselling book Too Big to Fail 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. You can grab signed copies of 1929 by Andrew Ross Sorkin at The Painted Porch: https://www.thepaintedporch.com/Follow Andrew Ross Sorkin on Instagram @SorkinSays and on X @AndrewRSorkin 👉 Support the podcast and go deeper into Stoicism by subscribing to The Daily Stoic Premium - unlock ad-free listening, early access, and bonus content: https://dailystoic.supercast.com/🎥 Watch the video episodes on The Daily Stoic YouTube channel: https://www.youtube.com/@DailyStoic/videos🎙️ Follow The Daily Stoic Podcast on Instagram: https://www.instagram.com/dailystoicpodcast✉️ 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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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 Squackbox, 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, squack 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. Here he is. He's at our table. Ryan Holiday, bestselling author of multiple books on Stoicism. His new book, Right Thing, right now, is out this week.

Here it is, and this is book number 16. Yes. That's a lot of books. That's probably two many years. Are you a Stoic? I try to be. Can we define Stoicism for the audience? It's 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 virtues 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? You know, it's surreal. When I went to my publisher in 2012 and I said I want to write a book about an obscure school of ancient philosophy, me, I'm not sure I envisioned any of this, and certainly they didn't envision any of this. So it's been surreal, the hero 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. Do you feel like you live a stoical life? Yeah. 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 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 this stuff, not so good at the other stuff, but I'm working on it when you're not good at. 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, but break those other pieces down, the justice piece and the courage piece, what that even means. 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 still. 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. Yeah. I think discipline and there's sort of, it's sort of, it's sort of such so physical. Well, what's fascinating to become mental. It is, 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, is not the X's and O's or how to get one percent 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. But anyways, I was surprised after to find out that Andrew Ross Orkin, 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 a 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 he came out to the studio and we had a lovely talk. I think you are really going to like this episode. In part one, Andrew talks about sort of the behind the scenes of the book and we're 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. It's the co-anchor of Squawk Box. He's the founder and editor of Deal Book. He wrote Too Big to Fail, which was not just a best-selling book, but a movie for HBO. And then he's the co-creator of Billions, if you haven't seen that show. 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 at Sorferday. Sorkin says or on Twitter at Andrew R. Sorkin. I'll just get into it. You've talked about procrastination on this on the show before. I tell myself the procrastination is not really procrastination. Okay. Meaning like even when you're tooling around the internet looking at other things. Sure. It may be a way of like creating a little bit of space in your brain to like then figure out the other thing. For me, I'm like, did I make a positive contribution to the project today?

I used to have this rule of like, in which I got from someone, which was 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

they 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, but in the last two minutes, you were like, oh, you know what? This would be a good opening sentence for chapter 16. And then that's moved the ball forward. 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. Yeah. 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 do 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'd then spend the next two days fixing them. Yes. But you had a lot less going on then. I did have a lot less going on that. I was not involved in any kind of TV shows. I was writing my column from the New York times and I was working hard on this book. Yeah. And I took some time off too. I mean from and this I never really took real time off. Yeah. It's like sometimes the forcing function of it's coming out is

exactly what you need. And then sometimes the no, no, no, you should take as much time as you need. 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. A six, 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 5 in the morning. I would drink the Diet Coke to get myself up. Yeah. And then I would start eating the chips and drinking the beer like 4 in the morning, go to sleep from like 5 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 to like 7. Yeah. Sort of a full day,

ish and then go back home and do it all over again. It was very... Did you just feel disgusting all the time? It's so disgusting. I felt so disgusting. I gained everything was bad about it. 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. Yes, completely. Oh, now I could never do that. I could never do that. Yeah. I'm 48 now. I was 30, 30 years old then, 31. 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. Right. And so I'm never like, oh, this, I'm like, quiet time. This is sleep time. I'm not going to be writing. 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 Ab's Diet.

There's a book right there. It probably doesn't include six Diet Coke. Yeah, it just, you can't do it. anymore you can't do it you couldn't do it then either there is something about like if i'm like getting in the zone i can eat an unlimited amount while i'm focusing yeah oh for me i can or reading yes the bad news for me is a weekend writing this book meant that i was just like living in the kitchen yeah i was trying to be good i'm eating like fayi yogurts and this and that but then i was always looking for crunchy things which is sort of a problem yeah well it's because you're not able to chain smoke like

200 cigarettes, which is, you know, like that, there's probably something about that. It's just kind of there. So you're having to replace it in the, like, I think writers were meant to do that and it's not good for you. So then you got to have something. Can't drink and write. I know people would do that. But what was the Corona? No, that was really just to go to sleep. That was to, that was because the Diet Coke was so, I was five Diet Coke's in. I need to stay awake. Now I need to go to sleep. This is before children's melatonin. Before melatonin. Yes. Now I'm now I'm a melatonin addict. I go to sleep early now. Yeah. I try to be asleep by 93010 because I got to be up so early. 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? And it's fabulous. And by the way, I use that as I cited in the end notes there. Oh, I didn't know. I didn't read the end notes. But you mentioned Mitchell is like going to a dinner with Churchill. Yes. Like we tend to Think of the depression or the market crash as this American thing as opposed to a thing that like had sucked in the entire world. Churchill, like Churchill being a great example of a Rube who's like sucked into the market. And doesn't he gets like sucked into the market? And then he gets like hit by a cab in New York all at the same time. It's such a 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. Yeah. As this whole thing is going down. come to New York, by the way, because he was out of money. And he came to the U.S. 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 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 loses it all like everybody else. But interestingly, unlike, I think a lot of people in the U.S. 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. That you could make money, like new fortunes could be made. And that the great sort of attribute of America was its resilience. Yeah. I don't think you appreciated that we're going to go through a decade plus long depression as a result of what it just happened. But yeah, he did not walk away, you know, 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 he's a park avenue. And he gets hit by a car. Yeah. It's an amazing, amazing little story. That's a metaphor there. Yes. Gets hit by a New York City cab. Exactly. Exactly. Yeah, there's, the way that smart people get sucked into it is fascinating to me. Like, you have turnout blurbs the book. That's the most fascinating. Which, by the way, I almost cried when he decided to do that. I mean, that was beyond. So I did cry. So he was here and did you, I'll send you. I've seen it. I've watched it. 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. I just saw him on your show talking about Mark Twain. Yeah. At the end, basically my nine-year-old like kicks his door open and he's like, I have some questions. And he sits here and asked him a bunch of Hamilton questions. How did I not see this? 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 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. But isn't that ultimately the lesson of all of us? Isn't that 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. 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. He knows all these titans of industry. and the inherent keeping up with the Jones is he realizes like, oh, no, no, no, making a lot of money from the sales of Huckleberry Finn, you got to invent a company, you got to go public, you got to, 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? Well, look, how do I keep my bearing? How do you keep your eyes on your own paper, like literally and figuratively, you know? Like, how do you go, I'm doing my bearings? thing. We're running different races. So a combination of things are going on. One is we are running different races. 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 bejillion homes. It's not, for better or worse, it's not in the cards. I feel like I'm running my own race. My own race is working out, frankly, better than I ever thought it was supposed to, so I'm pretty pleased with it. But yeah, I'm sure there's an element of me, but I think this is probably the human part of it, which is this is why I was saying, we were all trying to fill a hole. Yeah. Like, yeah, can you ever be enough, have enough, is it enough? You know, this is this great clip of Jim Carrey? Have you ever seen this? Is this about the wants everyone to be rich? No, it's, it's, it's, he's winning a golden globe.

Yeah. And he talks about, is it enough? Like, he's maybe one or two times or something. is he enough? Yeah. And I think that's a question that everybody asks themselves all that's like, is it enough? When's it enough? By the way, I'm somebody who's probably always trying to find the next thing. Yeah. 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? Yeah. 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 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 she's cool doesn't matter to me at all

her it's like it's all going to come out of the wash yeah you know I always say I'm worrying so she doesn't have to 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 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 Vonnegut says, what could that possibly be? And he says, I have enough. right, which is a pretty powerful thing. But do you think most people feel that way, that they feel like they have enough? 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. 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. You ever seen the movie Wall Street, too? No. Okay, not nearly as good as Wolfram won. Sure. And there's a scene in the movie where I think Shy LaBuff says to Josh Brolin, what's your number?

Yeah. Like, what's your number, like, where you'd feel like financial independence 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. I had a very revealing conversation with someone. and I'll tell you who it is off there, but they'd written a couple 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 a math, you know, it's like two and 20. 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. What are you going to do? And he was like, he was like, do you know who Elaine de Baton 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 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.

Oh, I didn't know that. And 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. I thought that's like the craziness of it right there. Function is the only health platform that gives you the data that most people never get, and it gives you the insights to start doing something about it too. With Function, you get access to over 160 lab tests annually,

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auraframes.com to get $35 off or his best-selling carver mat frames named number number one by wirecutter by using promo code Stoic at checkout. That's A-U-R-A-Frames.com promo code Stoic. This deal is exclusive to listeners and frames sell-out fast, so order yours now to get it in time for the holidays. Support the show by mentioning us at checkout. Terms and conditions apply. I got a question for you, because you've written a lot of books.

Yeah. And I was actually discussing this with my wife just a couple days ago, talking about enough. or whatever that even means these days. When you've finished the book and the book's out in the while, 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? So two thoughts there. So number one is I have come to realize that my job is to write that's that euphoria is in the journey 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 because 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 on the 21st of October. And I honestly, I don't know what anyone thinks of it. Like, because I

don't check reviews anymore, people can't send me emails about it. You don't check reviews. No. Well, my books tend not to be reviewed by publications. Okay. So, like, every once in a while, 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.

Good for you. 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'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, it's out, it did okay. But I try to focus on the part of it that I control, which is everything up until launch day.

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. Yeah. Which is weird. Yeah. 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. Yeah. Like the euphoria was the day you discovered that document in a library. That part was yours and yours alone and no one can take it away. And then, yeah, what the list says or what the reward 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. You do want to make sure, hey, it landed. I am not a stoic. I wish I was. I wish I was. 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 tradition bonus books come out on Tuesday. Should we pause? For people don't know, they're making a

lemonade outside. Is that what that is? Yeah. So, 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. Right. So we let people set up shot. 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, get the ice for the lemonade. But what was I saying. You were saying, what you were saying was that books come out on to Tuesday. Oh, yeah. Books come out on Tuesday. And so it's basically all the pre-orders 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. And so that period, after the book was done, but before the news, that was one of the shittiest weeks of my life. Yes. And when I did find out that my first book had hit the list, not the Times of the Wall Street 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 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. 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 book authors.

Do you think most of them feel this way? 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 of really shitty review in the Times came out. Right. 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.

I don't disagree with you at all. The Markets Realist 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. Oh, I love that. Is your wife, your book agent?

She is not. She is a literary agent, but she is not mine. I always thought that that would prove to be too complicated. Yeah, I was curious about that. Conflicty kind of perspective. A conflict of interest or a conflict of just. No, 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. Yes.

And I just thought, you know, better to have somebody else do that. 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 what you could, they could be like Ryan's being a little bitch right now. Yes. 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 the plausible deniability that you were taken seriously. That's what I, that's what I tell. myself. Does she read your work or do you guys exist in different literary worlds?

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. 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. Yeah. By the way, she had some good suggestions. I made I made the changes, and I was happy that she liked it. My problem is I've written too many books. It's just too much to ask any one person to have read all of them. Like, if someone came up to me and they said, I've read literally every book you've read

and I'd be like, does your wife read everything? Well, that's what I'm saying. Like, early on, I was like, you've got to 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.

I only got her to subscribe to the deal book newsletter. a couple years ago. Just to save, so she's vaguely aware of what you're working on? Yeah, I just felt, 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. Yeah. And then I discovered that she didn't read it with. Did that hurt your feelings?

Of course it did. Now, now she opens it every day to hopefully increase the open rate. Yes, yes, that's funny. Mark Twain's obviously a good example of someone gets caught up in it. But the most tragic example I think in American history is Grant, Ulysses S. Grant, just had no business being in the market and just gets eaten alive by it. Look, most of us have no business, not being in the market, but being stock pickers. It's just a very, very, very hard business. And it's why Warren Buffett famously tells his family members, just buy an index, close your eyes and look up a decade later and,

you should be in better shape. There's a famous Sherman quote. So for people don't 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. Oh, yeah. No, he gets totally engaged. And he's basically this guy stealing money and speculating.

Wow, he loses everything. And Sherman was saying how tragic it was that this dude who, he said, like, these Wall Street financiers would have 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, the doing the two things. But that's also human nature. People have success in one thing. By the

Yeah. This is true of all of the, you know, CEOs and politicians in the world and other people who, you know, 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. 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? Alch algorithm hedge fund guy. Ray Dalio. Ray Dalio. Yeah. Yeah, it's like you have all the money in the world. You're in this huge company, but he seems to want to be a thought leader more than anything. Well, I think in retirement now, he's trying to figure out what the next thing is. Sure. Yeah. He wants to be a writer. 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. Right. That doesn't work. Or they made a lot of money, had a lot of success. And they've made a lot of money, had a lot of success. And they, obviously. think, well, I'll do politics now. Right. And that doesn't always work.

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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. Yeah. And he did that. He was running General Motors. He ends up becoming sort of a head of the DNC, basically. 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. Huh. He thought in the fall of 1929 had this idea not to be nice to everybody.

Back then we worked on Saturdays. 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. Yeah. Work on their houses. Yeah.

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. 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. 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. Yeah. Right? I'd always written about sort of modern stuff almost in the moment.

And for me, this was like a stretch goal kind of thing because I thought, can I apply these things? Yeah. And, you know, I have friends who do journalism or write nonfiction books who have ambitions to write novels. 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. Right. 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. Right. Because it could have been terrible idea. Yes. But that's the thing about everything, right? And then, but this goes back to what is actually satisfying to you. Yeah. Meaning where's the euphoria come from? Sure. If the euphoria comes from writing the novel. 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. Right. All good questions and

depends. 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. No, and especially when you're told that you're wrong all the time. Yes. And then you seem to be able to shoot the moon and win. Yeah. Yeah. I actually think it would be very hard to actually be able to tell yourself that you're wrong. Well, Peter Thiel said if you were writing a book about Elon Musk, it would be titled The Man Who Knows Nothing About Risk. Yeah.

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, like, but the Midas touch story is a cautionary tale. Like it doesn't, it sucks to be King Mike. Well, it can be lonely, too. Yeah. Yeah. Right.

So, yeah, 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 would be a very tricky balance. I think it's a particularly tricky balance 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, I think it was difficult. think it's difficult for them today. It's not that I have great sympathy for them. Yeah.

In this regard. But I do think that when you sort of live in a cloistered world where a lot of things just get done for you. Yeah. It's hard to, and 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. 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 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. 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, 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. And they just get so used to being asked the question and thinking that they're like a wind-up toy and they're supposed to now pontificate. Like, that's what they're supposed to do. And so they do that. Yeah. No, I think podcasting is dangerous in that regard, too. 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 just nonsense. Did you, have you read? I feel like that's getting clipped, by the way, for the ground. Maybe. Well, have you read Mark Twain's letter to Vanderbilt? I don't know if I have. He famously writes this letter to Vanderbilt and he says, you don't know.

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 fortune. He was just saying that like you think you're a genius, but you're, 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 just like the, you know, the emperor's new clothes. And you're not, you don't live in reality. And anymore. And this is the fundamental peril 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, which he then falls prey to himself as an inventor. I mean, he was wealthy, but not

even close to what wealth is conceivable now. What year was that? I don't know. When is Or 70 billion, 70 million, you said? Yeah. Late 1800s. 70 million was still a lot of money in late 18 years. No, it's a lot of money, but it's just, you know, it's not a trillion dollar. Right. Pay package.

Our first billionaire was Rockefeller. Yeah. Our second billionaire, by the way, there was an article in 1929. The headline was our second billionaire. I know you quote that in the book. It's Ford, right? Henry Ford, yeah. Not inflation adjusted.

I often think about those characters because I'm often thinking about, you know, how much money is, yes, a trillion dollars a whole other level. Also, what could money buy you then? It's like, okay, it 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. It's different. You take the Emperor of Rome 2,000 years ago and it's like, sure, this is an incredible palace and these other things, but it's still like, it's fucking cold during the winter. And okay, I don't know if I should share the 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 $500 or $600 million, there's nothing that makes me different than the guy who's got $20 billion or $100 billion. Right.

This goes to your, you know, you can only make the train gustave fast. Yes. And I said, okay, break it down for me. Why's $500? What's $500 million? He said, well, once you have the plane. and you have two or three homes, which said maybe if there's some art and the staff,

it's like there's not much else that you can do. Right. He said you could have a boat. You said a boat. Oh, a super yacht. A super yacht. He said that's maybe in a different week. Yeah.

I remember that conversation sort of walking. 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 Bill Akman was saying, it's not possible to spend that much on a wedding. Like, the reporting was wrong. Right. 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. Right. And yet, there's some human compulsion to go beyond that money. Well, you probably met, you go to your point about the number. Right. How many people get to that number and then the number changes? Oh, I think for almost everybody, the number changes. Yeah.

By the way, even for myself, I remember, you know, when I was 20 or 25, thinking, you know, what would it take to feel? I wanted to write a book. I thought that would be a, like, that would do it. That's it. That's the goal. Touch the base. I'm done. Yeah.

Right. And then you're like, let's do the next one. Exactly. You can't stop. But I do think, and maybe this is Winston Churchill's point, that's what makes our society actually work, meaning that people do you have this drive. Yeah. 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. 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 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 to succeed anymore. That doesn't mean it's good for the individual who never has enough, right? So it's like there are these two, it's these two contradictory. 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.

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. By the way, there were people, obviously, in the late 20s or 30s, when there was 25% unemployment who thought that it was an oppressive society. I mean, you can even argue politically right now in parts of our country. There's questions about whether the sort of more and more capitalistic world even works at all. I live in New York City where we have a democratic socialists.

just have what have you seen the system do well in your lifetime right no and that's and that's a fundamental question in terms of like sure what we're talking about in a way yeah yeah of course you want to check out some books i'd love to let's do it 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 You know,