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

Summary

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

Date: December 6, 2025
Host: Ryan Holiday
Guest: Andrew Ross Sorkin

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Overview

In this engaging and thoughtful weekend episode, Ryan Holiday sits down with celebrated financial journalist and author Andrew Ross Sorkin for a wide-ranging conversation that delves into ambition, the meaning of "enough," creativity, and the psychological complexities of success. Building on their previous discussion (Part 1), the two address what drives high performers, how to remain grounded amidst “success mania,” and what lessons can be drawn from history’s titans—from Mark Twain to Elon Musk. The episode is laced with candid stories, memorable quotes, and a deep dive into why even the most accomplished find themselves haunted by the question, "Is it ever enough?"

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Key Discussion Points & Insights

1. Defining Stoicism and Personal Practice

Timestamps:
[05:25] – [06:56]

• Ryan Holiday's Take: Stoicism is not about controlling events, but about controlling one's response, using the virtues of courage, discipline, justice, and wisdom.
  • "My working definition is a stoic doesn’t control what happens, but they focus on how they respond to what happens... and the idea is the virtues of stoicism are courage, discipline, justice, and wisdom." —Ryan Holiday [05:28]
• Andrew’s Reflection: Even as a writer of stoicism, Ryan admits he's not mastered it—writing is as much to remind himself as to teach others.
  • "I’m writing about them first and foremost to myself, because I need reminders as much as anyone else." —Ryan Holiday [06:19]

2. The Real Challenges Behind High Performance

Timestamps:
[07:18] – [08:14]

• Elite performers (athletes, CEOs, generals) are all grappling with the mental side of things—the need to bounce back from setbacks, manage stress, and find inner stillness.
  • "At the elite level, it comes down to the mental side of things… that’s where the philosophy side of things really comes in." —Ryan Holiday [07:35]

3. The Writing Process: Procrastination, Output, and Health

Timestamps:
[10:04] – [15:18]

• On Procrastination: Sorkin recasts his own procrastination as mental space for ideation; Ryan values small daily contributions over strict word counts.
  • "Even when you’re tooling around the Internet looking at other things… it may be a way of like creating a little bit of space in your brain to then figure out the other thing." —Andrew Ross Sorkin [10:13]
  • "Did I do something that moved the ball forward today?... It might be that you had two hours and you wasted an hour and 58 minutes, but in the last two minutes, you’re like, 'oh, you know what? This would be a good opening sentence for chapter 16.'" —Ryan Holiday [10:25]
• Writing Rituals: Sorkin's early book processes were unhealthy—night writing powered by Diet Coke and beer, with little sleep.
  • "I used to get Tostitos and a six pack of Diet Coke and oftentimes a six pack of Corona Beer… I would write from like 10 o'clock at night till 5 in the morning." —Andrew Ross Sorkin [12:35]
  • "Did you just feel disgusting all the time?" —Ryan Holiday [13:21]
  • "So disgusting. I felt so disgusting. I gained… Everything was bad about it." —Andrew Ross Sorkin [13:23]

4. Financial Mania and the Allure of More

Timestamps:
[15:21] – [18:43]

• Vivid examples from history—such as Winston Churchill and Mark Twain—who, despite intelligence and fame, fell victim to speculative bubbles and the drive for more.
  • "Churchill being a great example of a rube who's like sucked into the market and... he gets like hit by a cab in New York City." —Ryan Holiday [15:45]
  • "He starts trading like crazy… then of course, he loses it all like everybody else. But interestingly… his reaction was America’s sort of optimism… was actually something that should be adopted more in the UK." —Andrew Ross Sorkin [15:59]
• On Mark Twain: Twain got caught up in "the mania of his time," unable to restrain himself, making and losing multiple fortunes.
  • "It’s never enough. And he can’t restrain himself and he makes and loses several fortunes as an investor." —Ryan Holiday [18:02]

5. The Eternal Question: “Is it Ever Enough?”

Timestamps:
[18:43] – [22:08]

• Alluding to Jim Carrey, Wall Street, and literary anecdotes, both discuss the insecurity driving success and the rare skill of feeling satisfied.
  • "Isn’t that ultimately the lesson of all of us? … We all want more. I mean, some people call that greed." —Andrew Ross Sorkin [18:43]
  • "How do you keep your eyes on your own paper? ... Like, how do you go, I’m doing my thing. We’re running different races." —Ryan Holiday [19:32]
  • "Can you ever be enough, have enough? Is it enough?" —Andrew Ross Sorkin [20:16]
  • "I have something this guy doesn’t have… I have enough." —Ryan Holiday re: Joseph Heller [22:02]

6. Ambition, Satisfaction, and the Joy of the Work Itself

Timestamps:
[26:42] – [32:10]

• Both reflect on the emotional aftermath of publishing a book. Relief, not triumph, is the common feeling. Ryan fixates on the “journey” of writing, less on accolades or external validation.
  • "I have come to realize that my job is to write… The euphoria is in the journey." —Ryan Holiday [27:17; 27:20]
  • "I thought I was going to feel a sense of euphoria… and the truth is, I just felt a sense of relief." —Andrew Ross Sorkin [28:58]
  • "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." —Ryan Holiday [32:10]

7. Transferable Success, Domain Expertise, and the Midas Paradox

Timestamps:
[34:32] – [43:21]

• Grant, Mark Twain, and Ray Dalio exemplify how prowess in one field tempts people to overreach into others—with disastrous results.
  • "The hubris of being like, hey, I’m good at… I should also be a great financier... That’s where you get yourself in trouble." —Ryan Holiday [35:19]
  • "People have success in one thing... and then they think, I can do this, this, this and this, as well… of course, most of the time they’re not." —Andrew Ross Sorkin [35:59]
• On Elon Musk and Big Bets: The perils of winning big, often, is the inability to recognize real risk or hear “no.”
  • "If you were writing a book about Elon Musk, it would be titled The Man Who Knows Nothing About Risk. Because he just takes—he goes all in all the time and then doesn’t die." —Ryan Holiday [44:05]

8. The Dangers of Success: Isolation, Distortion, and Self-Delusion

Timestamps:
[44:27] – [47:56]

• Success breeds a lack of honest feedback, creating "reality distortion fields."
  • "There’s no longer any intellectual give and take. It’s just we’re listening to the genius or to the guru… suddenly subjected to market forces in the way that in their life, it no longer is." —Ryan Holiday [45:22]
  • "Some of your ideas have no inherent significance or genius. They are just reflecting the glitter of your 70 millions." —Mark Twain’s letter, paraphrased [46:44]

9. Wealth, "Enough," and the Social Contract

Timestamps:
[48:08] – [51:48]

• Discussion of the material ceiling of wealth—how, past a certain point, money no longer changes quality of life, yet the desire for “more” remains.
  • "Once you get to about 5 or $600 million, there’s nothing that makes me different than the guy who’s got $20 billion or $100 billion." —Anonymous billionaire via Andrew Ross Sorkin [49:08]
  • "For almost everybody the number changes." —Andrew Ross Sorkin [50:17]
  • "It’s that ceaseless desire for more… that propels humans from where we were even 30 years ago… but if you don’t figure out some way to turn that off or turn it down, you end up in ruin." —Ryan Holiday [51:48]

10. Social Friction, Systemic Opportunity, and Disillusionment

Timestamps:
[51:48] – [52:32]

• Recognition that ambition and opportunity are not universal—many feel shut out of the system, fueling social and political tensions.

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Notable Quotes & Memorable Moments

"Can you ever be enough, have enough? Is it enough?... That’s a question that everybody asks themselves all the time."
—Andrew Ross Sorkin [20:16]

"I have something this guy doesn’t have… I have enough."
—Ryan Holiday, recounting Joseph Heller’s remark [22:02]

"My job is to write… the euphoria is in the journey."
—Ryan Holiday [27:17–27:20]

"There’s no longer any intellectual give and take. It’s just—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?'"
—Ryan Holiday [45:22]

"We all love ourselves more than other people, but for some reason, we care about their opinions more than our own."
—Ryan Holiday [32:10]

"People have success in one thing... they think... I can do this and this... and of course, most of the time they’re not."
—Andrew Ross Sorkin [35:59]

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Highlighted Timestamp Index

| Segment / Topic | Start | Key Quote / Moment | |:---------------------------------------------------------|----------:|:------------------------------| | Stoicism for modern life | 05:28 | "A stoic doesn’t control..." | | The elusive “enough” question | 20:16 | "Can you ever be enough..." | | The Heller/Vonnegut anecdote | 22:02 | "I have enough." | | Actual satisfaction: writing as a joy, not just output | 27:17 | "The euphoria is in the journey." | | The dangers of celebrity self-delusion | 45:22 | "No longer any intellectual give and take..." | | Money’s real limits | 49:08 | "Once you get to about 5 or $600 million..." |

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Final Thoughts

This conversation is an honest deep-dive into the strivings, insecurities, and philosophical questions faced by even the world’s most accomplished. Both Ryan and Andrew peel back the layers of status envy, creative drive, and existential doubt—to reveal that all the acclaim, wealth, and success in the world can’t answer the question alone: “Do you have enough?” Through stories of past greats and their own confessions, the episode offers not just caution, but comfort: the real fulfillment lies in the work, in recognizing your own race, and occasionally, in stepping back to say, "enough."

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Transcript

[Ryan Holiday]

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

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 Squawkbox, 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, Squawkbox is like the market 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.

[Andrew Ross Sorkin]

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 you've been writing over the years. Are you a stoic?

[Ryan Holiday]

I try to be.

[Andrew Ross Sorkin]

Can we define stoicism for the audience?

[Ryan Holiday]

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 to the best of our abilities.

[Andrew Ross Sorkin]

How much are you an author and how much are you, like, a psychiatrist to all of these people that come on your podcast?

[Ryan Holiday]

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. I'm not sure I envisioned any of this, and certainly they didn't envision any of this. So it's been. 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.

[Andrew Ross Sorkin]

Do you feel like you live a stoical life?

[Ryan Holiday]

Yeah, well, I'm. I'm certainly not writing the books from the perspective of having mastered these things. And I'm explaining to you how. How easy they are. I'm. I'm writing about them first and foremost to. To myself, because I need reminders as much as anyone else. I. 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.

[Andrew Ross Sorkin]

When you're not good at, you know.

[Ryan Holiday]

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

[Andrew Ross Sorkin]

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

[Ryan Holiday]

Yeah.

[Andrew Ross Sorkin]

So the.

[Ryan Holiday]

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. What can you do? So these sort of interlocking virtues are what try to shape us as. As aspiring still.

[Andrew Ross Sorkin]

Have you found. I mean, you. You talk to athletes and you talk to CEOs and all sorts of other people. Do you find that there's one type of. 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 so physical.

[Ryan Holiday]

Well, what's fascinating is, is, yeah, that. 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 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. So 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 Horkin, who is the co host of the show, was a fan. And he and I sort of stayed in touch. We had 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.

[Andrew Ross Sorkin]

And.

[Ryan Holiday]

And then it turns out he was gonna be in Texas. Cause 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. And I think you are really going to like this, this episode. 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 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's Saturday 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 Orkin says or on Twitter Drew are sorkin. I'll just get into it.

[Andrew Ross Sorkin]

You've talked about procrastination on this on the show before. I tell myself that procrastination is not really procrastination. Okay, meaning like even when you're tooling around the Internet looking at other things.

[Ryan Holiday]

Sure.

[Andrew Ross Sorkin]

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

[Ryan Holiday]

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, 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 thing 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. 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.

[Andrew Ross Sorkin]

Though because I didn't really have a, 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.

[Ryan Holiday]

Yeah.

[Andrew Ross Sorkin]

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.

[Ryan Holiday]

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

[Andrew Ross Sorkin]

I did have a lot less going on then. I 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.

[Ryan Holiday]

Yeah.

[Andrew Ross Sorkin]

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

[Ryan 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.

[Andrew Ross Sorkin]

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 5 in the morning.

[Ryan Holiday]

I would.

[Andrew Ross Sorkin]

I would drink the Diet Coke to sort of get myself up.

[Ryan Holiday]

Yeah.

[Andrew Ross Sorkin]

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 till like seven.

[Ryan Holiday]

Yeah.

[Andrew Ross Sorkin]

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

[Ryan Holiday]

Did you just feel disgusting all the time?

[Andrew Ross Sorkin]

So disgusting. I felt so disgusting. I gained. Everything was bad about it.

[Ryan 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 stuff. And now it's like you have a Diet Coke and you feel disgusting.

[Andrew Ross Sorkin]

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.

[Ryan 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.

[Andrew Ross Sorkin]

Right.

[Ryan Holiday]

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

[Andrew Ross Sorkin]

So I never sleep around 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.

There's a book right there.

[Ryan Holiday]

It doesn't include a Diet Coke. Diet Cokes. And.

[Andrew Ross Sorkin]

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

[Ryan Holiday]

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

[Andrew Ross Sorkin]

Oh, for me, I can.

[Ryan Holiday]

Reading.

[Andrew Ross Sorkin]

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

[Ryan Holiday]

Yeah.

[Andrew Ross Sorkin]

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

[Ryan 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 in the. Like. I think writers were meant to do that and it's not good for you. So then you gotta. You have something.

[Andrew Ross Sorkin]

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

[Ryan Holiday]

But what. What was the Corona?

[Andrew Ross Sorkin]

No, that was really just to go to sleep. To really. That was to tell us. Because the Diet Coke was so I. I was five Diet Cokes in. I need to stay awake now. I need to go to sleep.

[Ryan Holiday]

This is before children's melatonin.

[Andrew Ross Sorkin]

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

[Ryan Holiday]

Yeah.

[Andrew Ross Sorkin]

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

[Ryan 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.

[Andrew Ross Sorkin]

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

[Ryan Holiday]

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

[Andrew Ross Sorkin]

Yes.

[Ryan Holiday]

Like, we tend to think of the Depression or the market crash as this American thing.

[Andrew Ross Sorkin]

Yes.

[Ryan Holiday]

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 in the market and then he gets like hit by a cab in New York City all of a sudden.

[Andrew Ross Sorkin]

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 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, sending these letters back to his wife asking for more money. He had met a broker for EF Hutton who was advising him and. And then of course 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.

[Ryan Holiday]

That you could make money like new fortunes could be made and that the.

[Andrew Ross Sorkin]

Great sort of attribute of America was its resilience.

[Ryan Holiday]

Yeah.

[Andrew Ross Sorkin]

I don't think he appreciated that we were going to go through a, a decade plus long depression as a result of what had just happened. But yeah, he did not walk away, you know, scarred the way I think a lot of people did. He, he actually admired us for it. 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.

[Ryan Holiday]

And.

[Andrew Ross Sorkin]

And he gets hit by a car. Yeah, it's an amazing, amazing metaphor there.

[Ryan Holiday]

Yes. Gets hit by a New York City.

[Andrew Ross Sorkin]

Exactly.

[Ryan Holiday]

Crossing the street.

[Andrew Ross Sorkin]

Exactly.

[Ryan Holiday]

Yeah. There's the way that smart people get sucked into it is fascinating to me. Like you have Chernow blurbs. The book, like, that's the most fascinating.

[Andrew Ross Sorkin]

By the way. I almost cried when he decided to do that. I mean that was beyond.

[Ryan Holiday]

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

[Andrew Ross Sorkin]

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

[Ryan Holiday]

Did you see my son talking to him? So my 9 year old is obsessed with Hamilton and so we like let him come out of school. He got like.

[Andrew Ross Sorkin]

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

[Ryan Holiday]

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 he asks him a bunch of Hamilton questions.

[Andrew Ross Sorkin]

I see this.

[Ryan 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 can't quite wrap his head around how insane like, the experience is. But that's it. 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.

[Andrew Ross Sorkin]

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.

[Ryan 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. 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?

[Andrew Ross Sorkin]

Well, look, how do I keep my bearing?

[Ryan 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, so a combination.

[Andrew Ross Sorkin]

Of things are going on. One is we are running different races.

[Ryan Holiday]

Yeah.

[Andrew Ross Sorkin]

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. Yeah, 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 was probably the human part of it, which is. This is why I was saying we were all trying to fill a hole.

[Ryan Holiday]

Yeah.

[Andrew Ross Sorkin]

Like. Yeah. Can you ever be enough, have enough? Is it enough? You know, this is great clip of Jim Carrey. Have you ever seen this clip of.

[Ryan Holiday]

Wants everyone to be rich?

[Andrew Ross Sorkin]

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

[Ryan Holiday]

Yeah.

[Andrew Ross Sorkin]

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

[Ryan Holiday]

Yeah.

[Andrew Ross Sorkin]

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

[Ryan Holiday]

Yeah.

[Andrew Ross Sorkin]

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

[Ryan Holiday]

Yeah.

[Andrew Ross Sorkin]

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.

[Ryan 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.

[Andrew Ross Sorkin]

She's cool.

[Ryan Holiday]

It doesn't matter to me at all.

[Andrew Ross Sorkin]

For her, it's like, it's all gonna come out in the wash. Yeah. You know, I always say I'm worrying so she doesn't have to.

[Ryan 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 some finance billionaire's house in New York City, and Vonnegut is teasing. Hel 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.

[Andrew Ross Sorkin]

Right.

[Ryan Holiday]

Which is a pretty powerful.

[Andrew Ross Sorkin]

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

[Ryan 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. 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.

[Andrew Ross Sorkin]

You ever seen the movie Wall Street 2?

[Ryan Holiday]

No.

[Andrew Ross Sorkin]

Okay. Not nearly as good as Wall Street 1.

[Ryan Holiday]

Sure.

[Andrew Ross Sorkin]

And there's a scene in the movie where I think Shia LaBeouf says to Josh Brolin, what's your number? Yeah, like, what's your number? Like, where you'd feel, like, financial independence or, like, yeah, 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.

[Ryan Holiday]

I had a very revealing conversation with someone. 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 the math. You know, it's like 2 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 going to do? And he was like. He was like, do you know who Alain 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 fishermen 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.

[Andrew Ross Sorkin]

Oh, I didn't know that.

[Ryan Holiday]

And he's already 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. I thought that's, like, the craziness of it right there.

Thanks to Toyota Trucks for sponsoring this episode. When I bought my ranch in 2015 out here in Bastrop County, I drove my car about halfway down the dirt road that we live on. Thought, this isn't going to work. Stopped, parked. It walked the rest of the way home, borrowed my wife's car, drove into Austin, and bought a truck. What I bought was a Toyota Tacoma. And this truck wasn't just split transportation getting me to and from my house. It unlocked a whole different style of living for us, not just on the ranch, but in our little Texas towns. There were places I could go now that I couldn't go before, especially out here in the piney forests, through the fields, and on the unpaved roads like the one that I lived in. We got to go deep into the hill country's wild beauty. We've driven all the way out to East Texas. We've driven it across the country. And by we, I mean not just my wife, but both my kids, who I drove home from the hospital in that truck. Toyota trucks are built for those who understand that the best adventures happen when you're willing to veer off course, because you never know when you'll end up on a Toyota adventure detour. And, of course, this is stoicism, too, because every detour, every obstacle is an opportunity. But it's helpful if you can handle the difficulty inherent in that. If you've got the resilience and the right companion to make it wherever the road takes you, discover your uncharted territory. Learn [e-mail] Trucks Adventure detours.

[Andrew Ross Sorkin]

You hear that? That's not just a Toyota truck. That's the sound of no crowds, no alerts, no distractions, and no telling what you'll find next. You know, like a detour. So why would you ever take a tour when you could take a detour? Toyota trucks.

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

[Ryan Holiday]

Yeah.

[Andrew Ross Sorkin]

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 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?

[Ryan Holiday]

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

[Andrew Ross Sorkin]

That euphoria is in the. Is in the journey.

[Ryan Holiday]

Yes. Like, I've. I. 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 in on the 21st of October. 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.

[Andrew Ross Sorkin]

Don't check reviews?

[Ryan Holiday]

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

[Andrew Ross Sorkin]

Okay.

[Ryan 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's some random ass person.

[Andrew Ross Sorkin]

Good for you.

[Ryan Holiday]

So that requires not checking. But that also just means I just. Let's say they all got stolen before they came out. I like, wouldn't know, you know, and that's a little weird. Like I gotta 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.

[Andrew Ross Sorkin]

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

[Ryan Holiday]

Yeah.

[Andrew Ross Sorkin]

Which is weird.

[Ryan Holiday]

Yeah.

[Andrew Ross Sorkin]

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.

[Ryan Holiday]

Yeah. Like the euphoria was the day you discovered that document in the library. That part was yours and yours alone, and no one can take it away. And then, yeah, how it come what the list says, 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.

[Andrew Ross Sorkin]

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

[Ryan Holiday]

I was only aspiring to be one. But I remember on my first book, the week, so, you know, for people who don't know, the books come out on a two. All books, all traditional bonus books come out on Tuesday.

[Andrew Ross Sorkin]

Should we pause for people?

[Ryan Holiday]

I know they're making a lemonade outside.

[Andrew Ross Sorkin]

Is that what that is?

[Ryan Holiday]

Yeah.

[Andrew Ross Sorkin]

So.

[Ryan Holiday]

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.

[Andrew Ross Sorkin]

Right.

[Ryan 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. Get the ice for the lemonade. But what was I saying?

[Andrew Ross Sorkin]

You were saying you. What you were saying was that books come out on a Tuesday.

[Ryan Holiday]

Oh, yeah. Books come out on a 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. Right. And so that period after the book was done, but before the news, that was one of the shittiest weeks of my life.

[Andrew Ross Sorkin]

Yes.

[Ryan Holiday]

And when I did find out that my first book had hit the list, not the Times, the Wall Street Journal 1, 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.

[Andrew Ross Sorkin]

Oh, so you have a lot of authors who come through this beautiful bookstore that you've created here? Sometimes first time authors, sometimes multi book authors. Do you think most of them feel this way?

[Ryan Holiday]

Probably not. It's a lot. 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.

[Andrew Ross Sorkin]

Right.

[Ryan 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.

[Andrew Ross Sorkin]

I don't disagree with you at all.

[Ryan 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.

[Andrew Ross Sorkin]

Oh, I love that.

[Ryan Holiday]

Is your wife your book agent?

[Andrew Ross Sorkin]

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.

[Ryan Holiday]

Yeah, I was curious.

[Andrew Ross Sorkin]

Conflict kind of perspective.

[Ryan Holiday]

A conflict of interest or a conflict of just.

[Andrew Ross Sorkin]

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.

[Ryan Holiday]

Yes.

[Andrew Ross Sorkin]

And I just thought, you know, better to have somebody else do that.

[Ryan 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. They could be like, Ryan's being a little bitch right now.

[Andrew Ross Sorkin]

Yes.

[Ryan 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 were taken seriously.

[Andrew Ross Sorkin]

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

[Ryan Holiday]

Does she read your work, or do you guys exist in different literary.

[Andrew Ross Sorkin]

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.

[Ryan 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.

[Andrew Ross Sorkin]

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

[Ryan 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, read everything. Well, that's what I'm saying. Like, early on, I was like, 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.

[Andrew Ross Sorkin]

I only got her to subscribe to the DealBook newsletter A couple years ago just to save.

[Ryan Holiday]

Save, like. So she's vaguely aware of what you're working on.

[Andrew Ross Sorkin]

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.

[Ryan Holiday]

Yeah.

[Andrew Ross Sorkin]

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

[Ryan Holiday]

Did that hurt your feelings?

[Andrew Ross Sorkin]

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

[Ryan Holiday]

Yes.

[Andrew Ross Sorkin]

Yeah.

[Ryan Holiday]

Yes. That's funny. Mark Twain's obviously the great. A good example. Someone gets caught up in it. But the most tragic example, I think, in American history is. Is Grant. Ulysses S. Grant.

[Andrew Ross Sorkin]

Yeah.

[Ryan Holiday]

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

[Andrew Ross Sorkin]

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

[Ryan Holiday]

Right.

[Andrew Ross Sorkin]

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

[Ryan Holiday]

There's a famous Sherman quote because it. 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.

[Andrew Ross Sorkin]

Oh, yeah.

[Ryan Holiday]

No. He gets totally engaged 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 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, he's like, hey, I know I'm one of the great. 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 doing the two.

[Andrew Ross Sorkin]

Things, but that's also human nature. People have success in one thing. By the way, this is true of all of the CEOs and politicians in the world and other people who 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 completely transferable. And of course, most of the time they'. Not.

[Ryan Holiday]

Yes. I think it's like a. Who's the. Who's the investor that desperately wants to be an author? The algorithm hedge fund guy. What's his name?

[Andrew Ross Sorkin]

Algorithm hedge fund guy. Ray Dalio.

[Ryan Holiday]

Ray Dalio, yeah. 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 in retirement.

[Andrew Ross Sorkin]

Now he's trying to figure out what the next thing is.

[Ryan Holiday]

Yeah, sure.

[Andrew Ross Sorkin]

And yeah, he wants to be a writer.

[Ryan 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. 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. And that doesn't always work.

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[Andrew Ross Sorkin]

By the way, I was gonna say there's a character in this book, John Rascob. Yeah, 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. Yeah, and he did that. He was running General Motors. He ends up becoming sort of a.

[Ryan Holiday]

Head of the dnc.

[Andrew Ross Sorkin]

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

[Ryan Holiday]

Huh.

[Andrew Ross Sorkin]

What he thought. In the fall of 1929, he 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, all the 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.

[Ryan 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.

[Andrew Ross Sorkin]

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.

[Ryan Holiday]

Yeah, right.

[Andrew Ross Sorkin]

I'd always written about sort of modern stuff, almost in the mode, almost in the moment. And for me, this was like a stretch goal kind of thing because I thought, can I apply these things? And, you know, I have friends who do journalism or write nonfiction books who have ambitions to write novels.

[Ryan 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. 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 then it somehow worked doesn't necessarily mean it was a good idea.

[Andrew Ross Sorkin]

Right.

[Ryan Holiday]

Because it could have been.

[Andrew Ross Sorkin]

Could have been a terrible idea. Yes, but that's the thing about everything. Right. And then. But this goes back to what is actually satisfying to you. Meaning, where's the euphoria come from?

[Ryan Holiday]

Sure.

[Andrew Ross Sorkin]

If the euphoria comes from writing the novel, maybe.

[Ryan Holiday]

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?

[Andrew Ross Sorkin]

Right. All good questions and depends.

[Ryan Holiday]

Like, it would be very. It would be. I'm sympathetic to it as often as I am 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.

[Andrew Ross Sorkin]

And especially when you're told that you're wrong all the time.

[Ryan Holiday]

Yes.

[Andrew Ross Sorkin]

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

[Ryan Holiday]

Yeah.

[Andrew Ross Sorkin]

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

[Ryan 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.

[Andrew Ross Sorkin]

Yeah.

[Ryan 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.

[Andrew Ross Sorkin]

Yeah, like.

[Ryan Holiday]

But the Midas Touch Story is a cautionary tale. Like, it doesn't. It sucks to be King Midas.

[Andrew Ross Sorkin]

Well, it can be lonely, too.

[Ryan Holiday]

Yeah.

[Andrew Ross Sorkin]

Yeah.

[Ryan 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.

[Andrew Ross Sorkin]

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. I think it's difficult for them today. It's not that I have great sympathy for them 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.

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.

[Ryan 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. 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.

[Andrew Ross Sorkin]

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 it is that they, they're like a wind up. They're supposed to now pontificate like that's what they're supposed to do. And so they do that.

[Ryan 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.

[Andrew Ross Sorkin]

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

[Ryan Holiday]

Well, have you read Mark Twain's letter to Vanderbilt? I don't know if I 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 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 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, which he then falls prey to himself as an inventor, of course. I mean, he was wealthy, but not even close to what wealth is conceivable.

[Andrew Ross Sorkin]

Now, what year was that?

[Ryan Holiday]

I don't Know when does corn.

[Andrew Ross Sorkin]

70 billion. 70 million, you said?

[Ryan Holiday]

Yeah, late 1800s.

[Andrew Ross Sorkin]

70 million was still a lot of money.

[Ryan Holiday]

No, it's a lot of money, but it's just, you know. You know, it's not a trillion dollar. Right. Pay package.

[Andrew Ross Sorkin]

Our first billionaire was Rockefeller.

[Ryan Holiday]

Yeah.

[Andrew Ross Sorkin]

Our second billionaire. By the way, there was an article in 1929. The headline was our second billionaire.

[Ryan Holiday]

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

[Andrew Ross Sorkin]

Henry Ford. Yeah. Not 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. Yeah, whole nother level.

[Ryan 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 you take the emperor of Rome 2,000 years ago, and it's like, sure, this is incredible palace. These other things. But it's still. It's fucking cold during the winter.

[Andrew Ross Sorkin]

And 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 5 or $600 million, there's nothing that makes me different than.

The guy who's got $20 billion or $100 billion. This goes to your. You can only make the train go so fast. 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 you have some art and the staff. He's like, there's not much else that you can do.

[Ryan Holiday]

Right.

[Andrew Ross Sorkin]

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

[Ryan Holiday]

Oh, a super yacht.

[Andrew Ross Sorkin]

A super yacht. That's. That's maybe in a different league. Yeah, I mean, I remember that conversation sort of walking away going, huh.

[Ryan 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. 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've probably met, you go to your point about the number, Right. How many people get to that number and then the number changes.

[Andrew Ross Sorkin]

Oh, I think for almost everybody the number changes.

[Ryan Holiday]

Yeah.

[Andrew Ross Sorkin]

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.

[Ryan Holiday]

I thought that would be a, like.

[Andrew Ross Sorkin]

That would do it.

[Ryan Holiday]

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

[Andrew Ross Sorkin]

That's the base. I'm done.

[Ryan Holiday]

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

[Andrew Ross Sorkin]

Exactly.

[Ryan Holiday]

You can't stop.

[Andrew Ross Sorkin]

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

[Ryan Holiday]

Yeah.

[Andrew Ross Sorkin]

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.

[Ryan 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 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. Right. To succeed anymore. That doesn't mean it's good for the individual who never has enough. Right. So like 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 end up in ruin.

[Andrew Ross Sorkin]

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.

[Ryan Holiday]

Yes.

[Andrew Ross Sorkin]

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

[Ryan Holiday]

Sure.

[Andrew Ross Sorkin]

Whether the sort of more and more capitalistic world even works at all. I mean this is, I live in New York City, where we have just.

[Ryan Holiday]

What have you seen the system do well in your lifetime? Right.

[Andrew Ross Sorkin]

No, and that's, and that's a fundamental question in terms of like, sure. What we're talking about in a way.

[Ryan Holiday]

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

[Andrew Ross Sorkin]

I'd love to.

[Ryan Holiday]

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.

Foreign.

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[Andrew Ross Sorkin]

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