The Daily Stoic - Can a Billionaire Be a Stoic? | Robert Rosenkranz (PT. 1)

Episode Date: May 7, 2025

Wealth can free you—or consume you. Self-made billionaire Robert Rosenkranz joins Ryan to discuss how Stoicism can transform our approach to money, ambition, and identity. Robert shares how Stoicism has shaped his decision-making, honed his intuition, and influenced his mindset on wealth and living a fulfilling life. Robert Rosenkranz became a self-made billionaire as a pioneer in private equity, multi-strategy hedge funds, and the insurance industry. He launched the acclaimed NPR program, Open to Debate, funded Impetus Grants to extend human healthspans, and is founding an innovative cultural institution in New York to showcase immersive work at the intersection of visual art, sound, music, and technology.📕 Grab a copy of The Stoic Capitalist: Advice for the Exceptionally Ambitious by Robert Rosenkranz💡The Wealthy Stoic: A Daily Stoic Guide to Being Rich, Happy, and Free explores how stoic ideas can be applied to personal finance, wealth-building, financial mindset, and how it can help you overcome common financial obstacles and challengesGet The Wealthy Stoic: A Daily Stoic Guide to Being Rich, Happy, and Free & all other Daily Stoic courses for FREE when you join Daily Stoic Life | dailystoic.com/life🎙️ Follow The Daily Stoic Podcast on Instagram: https://www.instagram.com/dailystoicpodcast🎥 Watch top moments from The Daily Stoic Podcast on YouTube: https://www.youtube.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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Welcome to the Daily Stoic Podcast, where each weekday we bring you a meditation inspired by the ancient Stoics, a short passage of ancient wisdom designed to help you find strength and insight here in everyday life. And on Wednesdays, we talk to some of our fellow students of ancient philosophy, well-known and obscure, fascinating and powerful. With them, we discuss the strategies and habits that have helped them become who they are and also to find peace and wisdom in their lives. Hey, it's Ryan. Welcome to another episode of the Daily Stoic Podcast. So how rich was

Seneca? Right? We know he's wealthy. He's supposedly the second richest man in Rome. I just was giving a talk at JP Morgan Chase a couple of weeks ago, and I was explaining to them that Seneca was such a powerful financial force inside the Roman Empire, that when he calls in some loans to the Roman colony in Britain, it causes so much unrest. It so upends their economy that it leads to what's called the Boudica rebellion, which sets in motion over time,

eventually the independence of Britain as its own sort of nation. That's like one of the earliest sort of British stories, this Boudicca rebellion. So Seneca is not just wealthy, but he is like in the mix. He is like a JP Morgan Chase rich. He is a Elon Musk rich. Now, even then, even back then,

people thought this made him a hypocrite. They contrast, you know, his talking about practicing poverty, his talk about discipline, his talk about moderation, his talk about virtue with his enormous wealth. Some of this is from sort of sour grapes critics. Some of it is just from people who didn't like Seneca, but there is a kernel of truth to that.

There's something not exactly right about Seneca in many ways, right? Not just that he has lots of money, but how he gets his money. He gets it in largely in the service of Nero, although he comes also from a wealthy family. I guess what I'm meaning to say is that the debate about stoicism and money or philosophy

and whether it was incongruent with money, this is like as old a discussion as there possibly could be. Even back to Diogenes and Plato, Diogenes sort of skews all worldly things like in this sort of transgressive punk fashion. And, you know, he walks into Plato's fancy house one day and starts stomping on the carpets and he goes, I trample on Plato's vanity.

And Plato points out that this itself, this scorning of wealth and any kind of material niceties is itself a kind of vanity. So again, this goes way, way back. That's why I thought it was so fascinating when I got an email about this book called The Stoic Capitalist, Advice for the Exceptionally Ambitious.

Now, look, anyone could write a book about stoicism and money, and I'm sure there are some academics out there that have, but the guy that wrote this, Robert Rosencrantz, is a self-made billionaire. He's one of the pioneers of private equity, hedge funds, insurance. He's also like an ancient Roman,

a patron of the arts and medicine. He's been a sort of quiet donor and the champion of civil discourse and free speech. He launched this acclaimed NPR program called Open to Debate. He did this thing called the Impetus Grants, which is designed to extend human health spans and done a bunch of other interesting things, all of which is to say he's got skin in the game of the debate. He's not writing about wealth and

philosophy from some academic perch, but as a person who as a capitalist has made more than he could spend in many lifetimes. And so I thought he would be fascinating to talk to. The idea of the book is actually really interesting and quite good. And I think you will like it, especially if you are an exceptionally ambitious person. If you are interested in exploring this idea of wealth and stoicism,

the thing we put together called the wealthy stoic, a daily stoic guide to being rich, happy and free is all about personal finance and wealth building and how to think about money. But again, not how to just accumulate lots of it, but how to be wealthy, whether you have a lot or a little. And there are plenty of people who have a little and feel quite wealthy and plenty of people who have a lot

and feel quite poor, as Seneca himself noted. A lot of Seneca's criticism of wealth, you have to understand, are probably directed at himself first and foremost. And he says, slavery lurks beneath marble and gold. What do you think he's talking about? He must've been talking about his own sense of being less free than he would like to be.

I really enjoyed this interview. You know, they don't always go this long. So we're splitting this one up into two. And I think that's a sign that I enjoyed the conversation and I found Robert to be very fascinating. And I think that you will too. You can grab the Stoic Capitalist, Advice for the Exceptionally Ambitious,

and you can check out the wealthy Stoic. I'll link to that in today's show notes. Or if you sign up for Daily Stoic Life, you get it and all the Daily Stoic courses for free. Is there anything better than one of those like doorstopper of a biographies of like a great historical figure? You seem like someone who likes those books. I do. I mean, it was it was critical for me as a kid

because it gave me the role models that I absolutely did not have at home. Yeah. And when you dig into into the full life of someone, both what makes them great and their sort of tragic flaws, that's what I'm fascinated by. Yeah. Well, I mean, I was reading these biographies, like I say in the book, as sort of how to do it manuals for success in life. How do you get to be powerful and famous? And once you are that thing, what do you do?

What do you do about public service? What do you do about your kids? What do you do about relationships? Did you want to be powerful and famous as a kid? I had no idea. I mean, I just knew I didn't want to be like my parents. Yes, I felt the same way. But I didn't know if it was necessarily possible

to be different than your parents. As a kid, I didn't, one of my parents friends had a job and most of them were civil servants in some form or the so the idea of like Running your own company or being an artist or I don't know doing anything other than having a job I wasn't I didn't know if that was I knew I didn't want to do that But I didn't know you really could do that. Well read some biographies. Exactly. Yes really could do that.talking about biography Exactly.

Get some good ideas. Yes, that's what a biography does is it gives you a glimpse into another world or another way of going through the world that chances are is very different than your own. Yeah, in my case, radically different. Well, you know, that's how Stoicism is founded. Zeno gets this prophecy as a young man that wisdom comes from talking to the dead. And it's only when he suffers this shipwreck and he loses everything, he washes up in Athens, and he ends up in a bookstore, that he realizes that that's how you talk to the dead. Ah, yeah. There's a great line that I like from Seneca where he says, we can't choose

our parents. That's given to us by accident, but we can choose whose children we want to be. And that's sort of the same idea. And then Marcus Aurelius starts off meditations with the people whose lives he's tried to learn from. Well, yeah, I mean, he loses his father as a young man, but he's given this incredible gift of a stepfather who chooses him and he doesn't have to like Antoninus. He doesn't have to learn anything from this person. And like historically, they should have hated each other.

Like they should have been at odds with each other. Why do you say that? Well first off, I guess you'd call this a regent. How often does the prince plot against the regent? This is like the plot of every Shakespearean play or sort of medieval story. There should have been an assassination attempt or, I mean, most of the Greek myths are like

the prince being sent away to live as a pauper somewhere. The idea that these two who are thrown together by fate, right? Hadrian chooses Antoninus in return, that he has to choose Marcus Aurelius. And that the two get along for two decades and learn from each other and love each other and refer to each other as father and son. I mean, that's pretty unusual.

Even in the business world, how often does the CEO's chosen successor get along with, you know, they hate each other by the end. It definitely has stresses associated with the relationship. Yeah, well, it starts off well, and then in that limbo period, it tends not to go well. I mean, and how often even afterwards do they, I mean, this is the story of Disney

right now, right? The CEO chooses a successor and then decides they want to come back or disagree. This is the story of Theodore Roosevelt and his successor. It never works, but it did work in this one case. It's pretty remarkable. Well, it's sort of that stoic idea. Things change and you have to expect them to change. Yes. I always loved that line from Seneca about how we choose who our parents are going

to be. And to me, that's the story of mentorship. You can't choose who they're going to be. We can choose who we wish they were. Yeah. But we can choose additional parents. And I think there is something in what Seneca is talking about that is kind of a quirk of Roman life, which back then, families would often adopt adult children into the family to take over the business. Seneca's brother is adopted by a family and changes his name, and he's in the Bible. You know, that also embodies an idea of meritocracy that, you know, to me was like a really central

American value and it's a bit under threat. Yeah. Well, I mean, even we have these emperors and kings generally terrible system, but Rome has sort of five good ones in a row. And the reason it has five good ones in a row good ones in a row. And the reason it has five good ones in a row is because they each chose their successor. And then the last one that was terrible, and this is on Marcus Aurelius, is his son, Commodus, who's as bad as Joaquin Phoenix's character portrays him to be or even worse. So yeah, nepotism, family business, it doesn't usually work that well. So when did you come to the Stoics? Because you're clearly pretty well versed in them. Well, I got into it really through a relationship I developed with a guy called Baruch Fishman,

who's one of the leading thinkers in cognitive behavioral therapy. And he kind of introduced me to the Stoics as the intellectual forebears of cognitive theory. And I started reading the Stoics and I realized that this was my natural mode of thought. This was the way I was reacting as a child to the challenges that I was facing. And I couldn't have articulated it in the same way, but it was my natural response. And I felt like there were lessons here. I mean, it gave me a framework for taking I mean, he gave me a framework for taking a very ambitious life in my own case and seeing a pattern where I could hopefully tell stories that could help other people realize their childhood dreams, just as this mode of thought helped me realize mine. A young man fakes his own death and impersonates his cousin to collect a huge inheritance. What could possibly go wrong?

Don't miss this side-splitting comedy, Tons of Money at the Shaw. For tickets go to shawfest.com I'm John Robbins and on my podcast I sit down with incredible people to ask the very simple question, how do you cope? From confronting grief and mental health struggles to finding strength in failure, every episode is a raw and honest exploration of what it means to be human. It's not always easy, but it's always real. Whether you're looking for inspiration, comfort or just a reminder that you're not alone

in life's messier moments, join me on How Do You Cope? Follow now wherever you get your podcasts or listen to episodes early and ad free on Wondery Plus. How Do You Cope? is brought to you by Audible, who make it easy to embark on a wellness journey that fits your life with thousands of audiobooks, guided meditations, and motivational series. So was it early in life or later in life that you came for the sort of confirmation that Stoicism was your sort of mode of thinking? Where are you in life when you go,

oh, that's what I've been doing? That was pretty late, actually. That was in the last 15 years or so. Wow. Interesting. Yeah, I do get the sense there's a lot of people who are sort of intuitively stoic or not naturally stoic because that implies they're not consciously doing it. But it is kind of a thing they learned by trial and error rather than something that in the ancient world you would have been sort of inculcated in and taught from birth.

You sort of figure it out. And then maybe there's something too about the investing world that really either you think this way or you're going to get yourself in trouble. Do you know what I mean? Like the market not caring about you, the market not being in your control, I think does sort of force you to deduce certain stoic lessons if you want to exist and thrive in that world. Yeah, I would agree with that. Although, I mean, for me, it started so much earlier.

Interesting. My early experiences, as I had mentioned, were that my mother was a clerk in a drug store. My father was unemployed. I was totally aware as a six or seven-year-old kid that they were struggling, they were afraid that their electricity was going to get cut off or their phones were going to get a cut off or they couldn't pay the butcher. And I mean, this was an upsetting thing for a kid. And, I mean, this was an upsetting thing for a kid. But I had this innate resilience and I kind of had this idea that, okay, my parents haven't figured out how the world works and

my mother can't deal emotionally with the stresses that she's under. So I've got to figure this out for myself. And it's that idea of resilience, that idea of self-reliance, and that idea of critical thinking. Because my mother was a communist, and the kind of stuff she would say just seemed wrong to me. Interesting.

So I kind of took from this sort of set of bad ideas and bad circumstances, stuff that was really, really useful, the idea of critical thinking, the idea of self-reliance, the idea of reading biographies, that was a critical element in my development because, as we said earlier, you can choose who you'd like your parents to be.

And if you don't have role models at home, reading biographies and reading them as how to do it manuals for success in life can be transformative for me. Yeah, I just mean, you know, the market isn't good or bad. It just is. Yes, exactly. And you have to figure out, just like life,

like your circumstances aren't, the stoics would say it weren't actually good or bad. They just were. That's when you were born, that's who your parents were, and you don't control that, but you do control what you make of it, the decisions that you make in response to it, where you go from here.

And I think there is, I just mean from all the different investors and traders that I've met over the years, there is something about sometimes the stocks go up, sometimes they go down, sometimes this happens, sometimes that happens, and you just have to figure out what you're going to do because your opinion about it is irrelevant. Whether you like it, whether it's good for your portfolio in the short term or not is irrelevant. It is.

Yeah. There's a chapter in the book called Behold the Earthlings. And it deals with the idea of observe the conduct of people in the marketplace. You're not judging, oh, this stock is cheap or this asset is rich. You're just looking at how the earthlings are behaving. And you're not passing a judgment on it. You're just trying to figure out what they're doing and benefit from trends, get out of the way of things that are going against you, that kind of idea. Yeah, well, the Stoics talk about getting to like Plato's view, like zooming out and seeing it from above, because in the middle of it, it can seem like it's the worst

because in the middle of it, it can seem like it's the worst conditions ever, or it can seem like the most exciting lucrative conditions ever. The part of being a good investor, I imagine, is putting aside what everyone else thinks and going to what you think, but then also simultaneously being able to hold in your head, this is what other people think. And that's why, like the market's not rational either, right? What's that expression about how the market can remain irrational longer than you remain solvent? So just being right also isn't enough. You have to understand other people are wrong. Other people might be in positions of power. This trend might be likely to continue

for this amount of time. So the ability to think not just about what you think, likely to continue for this amount of time. So the ability to think not just about what you think, but hold in your mind what other people are thinking without letting it change your thinking. Well, the particularly tricky thing about markets is that consensus thinking is by definition wrong at key turning points. What makes a market top is that everybody is bullish. What makes a market bottom is that everybody is bearish. So you can go along with the crowd and be okay most of the time. But when it really matters, you've got to be, go against the crowd, be independent. And certain strategies require that.

I've always liked that about the Stoics. There's kind of a contrarian streak to them. Yep, absolutely. Like one of the Stoics, Chrysippus said the whole point of being a philosopher is to not be a part of the mob, meaning the rabble, like to not think what everyone else is thinking. And if you are thinking what everyone else is thinking, you're probably not thinking for yourself. Yeah, I couldn't agree more. How do you manage your emotions? Which, you know, Stoics makes sound really simple,

but it's probably not easy when there's millions or billions of dollars on the line. I mean, you talk about you started your company, putting your entire net worth into it. So that's not, that's not easy to be like you win some, you lose some, sometimes it goes up, sometimes it goes down. But that's not easy to be like, you win some, you lose some, sometimes it goes up, sometimes it goes down. No, that was a real commitment. You know, there's a chapter in the book that is about when to go all in. And it's sort of, it's my story of how I applied the stoic virtue of using rationality to overcome fear basically.

So in this episode, which was a key turning point in my life, I was starting my own business. I had a gentleman who was putting up the money that I needed to get started. And the conventional way to do it was that the person running the money, or in this case, running the firm, would get 20% of the profits and have no investment. And he pushed back against that. And I said, okay, I'll put up 100% of my liquid net

worth, which is about $400,000. I was 35 years old. That $400,000 in those days was the equivalent of about $4 million today. So substantial amount of money. And I said I'd put it all at risk. And not only would I put it all at risk, but I'd put it at risk in a leveraged way so that I wanted 50% of the profits, but I would absorb 50% of the losses. So if he's down 10%, I'm wiped out. And that was the most courageous business decision I've ever made, but it was a triumph of rationality. How so? It seems fundamentally irrational. Well, because if you look at the odds, it looked to me, I felt based on my experience

in as a pioneer in leveraged buyouts, that there was maybe one chance in three that we could make $100 million out of this original $4 million stake that he was putting up, again multiplied by 10 for today's purchasing power. So I thought there was a one chance in three of that. And by going from a 20% share, if it worked out, to a 50 percent share, that had a mathematical value of about an extra $10 million. I thought there was one third chance that I could lose everything. But that had a mathematical value of $167,000.

So I was looking at $167,000 loss versus a $10 million gain. That's the rational calculation. And the rationality trump the fear in my case. And another thing that the Stoics teach is that if you're afraid of an outcome, it helps to assert rational control. If you think about what's really the worst that can happen. So yeah, the worst that could happen in my case, I would have lost all of my liquid assets. But I had some illiquid positions that I thought would eventually turn into cash.

I thought I could replace, get back the kind of job or junior partnership that I had at a comparable firm or even return to Oppenheimer, which was where I was leaving. So it didn't seem that bad, by really trying to imagine realistically what the bad outcome looked like, and not so terrible.

I didn't catastrophize. I didn't say, oh my God, I'd be homeless. Oh my God, I'd be destitute. Oh my God, I'd be in my parents' position of not being able to pay the electric bill. Yeah, we sort of lump all of our fears into this kind of vague dread that we associate almost with death or something.

And so we go, I can't do it because the worst case scenario is unthinkable. But the worst case scenario is really just unthinkable because we haven't really thought about it. And then you think about it and you go, yeah, I could just get it. Get my job back. I remember when I dropped out of college, I remember as I was thinking about doing it, it's like, if this doesn't work out, I'm going to end up under a bridge somewhere, you know?

And someone who was older was like, you know, you can just go back at any time. Like he's like, he's like, he was telling me he was like, I spent a year of college in the hospital. Like he got some sickness. He's like, so it took me five years to graduate from college. And he's like, it's not once ever come up with anyone. You know, we don't think about the worst case scenario. And so it's unthinkable to us.

And then we're not able to balance it out against, as I think you did in this case, also the rational upside. And we've evolved as a species to prefer the certain win over the possibility of a larger payoff and particularly if that larger payoff involves taking some risks that you can avoid. Was that expected return or expected? The calculation where you go, hey, if there's a 10% chance of making $100 million, I should spend $10 million to try to get that. How investors think about that is really interesting. Obviously, the Stoics didn't have the market as we understand it now, so they weren't really doing those math equations. But that math equation is always interesting to me,

because it's a way to add some rationality to an unpredictable thing, I guess. Well, there's also, I mean, there's a lot of complicated thinking around, even if the odds are in your favor, how big do I bet? You know, if I said, okay, you can go to Las Vegas and just special day for you, the roulette table is going to to pay instead of 30 to one, it's going to pay a hundred to one. The odds are in your favor. Big time. Yeah. Would you bet your whole net worth on it? Hell no. I would think. Yeah, probably not. But how big a bet should you make? Yes.

And it's a question to some degree of how many chances you're going to get. You know, if you think you're going to have a hundred chances to make this bet, you might do it very differently than if you think you only have one chance in a lifetime. And for me, I felt like I was literally dealing with a chance of a lifetime when I started my firm. I mean, the firm, the point of the firm was really to buy operating businesses in a leveraged

way. So put up as little money as we can, borrow as much as we could. And the chance of, I mean, that was an unusual confluence of circumstances where you could buy companies at reasonable prices and get banks or insurance companies to lend you 90%. That was not likely to last. I mean, either the prices were going to go up or the availability of financing was going to go down. But this was a really unusual confluence of circumstances. A moment in time. A moment in time. And I was influenced by the Shakespeare quote from, again, Julius Caesar, there's a tide in the affairs of men which if taken at the flood leads on to fortune.

And I kind of believed that. I thought this was my tide and I better ride it as far and fast as I could. Well, it's funny because you're riding it as far as fast as you can, but there's also something stoic about you're gonna do something, you're gonna take this bet. I think most people just sort of trust like intuition or gut. And I think what great investors do is they slow things down and

they stop. They think not just, hey, should I make this bet? But as you said, mathematically, how big of a bet should I make? And that ability to kind of challenge your doubts or your fears or your like, obviously, at some some level we all have intuition that's good but not letting that make you either do something too risky or not risky enough is really interesting. Like the sort of stopping down, hey, I'm going to really look at the odds here. And then once I know the odds, I want to look at what I'm comfortable doing, what's okay to do, what has the most upside, the least downside.

That kind of calculation, again, the Stokes don't explicitly talk about that, but I think that is kind of the idea, is to slow it down and really think about it, to put every impression to the test. There's a line from Epictetus II where he talks about how, if you train enough in the philosophy,

you should become like a money changer. And he talked about how in the old days, like they had, you know, coins made of precious metals, but there were counterfeiters then too, and they would try to dilute the metal inside the coin or they'd melt it down and steal some of it. And he said a great money changer can bang a coin on the table and know from the sound of it alone, whether it's pure or not, whether it's been diluted or not. To me, that's what intuition was really allowing us to do is to sort of, we have these thoughts,

we have these opinions, there's this conventional wisdom, and you have the ability to know whether that's true or not, whether that requires further examination or not. And it's in those things where everyone thinks this, and you actually sense there's something not right about it, in those things where everyone thinks this and you actually sense there's something not right about it or you sense there's more here, that there is the opportunity of a lifetime here. Developing that kind of intuition and know when to delve into something or really get to the bottom of it. I like that.

But intuition sort of implies that it's a kind of a inbred quality. To me, it's more the habit of critical thinking, of not absorbing beliefs just because it's what you read in the Times, or it's not just because it's what your parents are telling you, or not just it's the consensus of your friends, but subjecting almost everything you hear to kind of critical thought. And to me that is like so central

and was kind of why I started Open to Debate as a philanthropic initiative was the idea that our world needed something like this, needed a place where people could talk about contentious issues in a civil way, where an audience could listen to both sides because it's something that you rarely get. And by listening to both sides and listening respectively and thinking about the facts, you're both coming to better conclusions about contentious issues, but you're also exercising a part of your mind

that is incredibly important. The world can seem pretty chaotic sometimes, and if you're a parent, that's the last thing you need. Which is why I think you'll appreciate a podcast that offers clarity, perspective, and hopefully a little serenity to your world. Each week on Janet Lansbury Anne Ruffold, I strive to help with your most confounding issues and offer practical, holistic advice so you can be the parent you want to be, calm, connected, confident, even in the most challenging moments.

My goal is to help take the chaos out of parenting, to shed light on the root causes of our kids' behavior so we can respond effectively without anger, threats, or even bribes. By embracing our role as respectful leaders, establishing both trust and boundaries, we can enjoy a loving relationship with our kids that encourages mutual cooperation and respect. So check out Janet Lansbury on Ruffled, on Wondery, or wherever you listen to podcasts. We can do this. Whole Foods started in the counterculture city of Austin, Texas, and it took pride in being anti-corporate and outside the mainstream.

But like the city itself, Whole Foods has morphed over the years for better and perhaps for worse and is now a multi-billion dollar brand. In the latest season of Business Wars we explore the meteoric rise of the Whole Foods brand. On its surface it's a story of how an idealistic founder made good on his dream of changing American food culture. But it's also a case study in the conflict between ambition and idealism. how lofty goals can wilt under the harsh light of financial realities, and what gets lost on the way to the top.

Follow Business Wars on the Wondery app or wherever you get your podcasts. You can binge Business Wars, The Whole Foods Rebellion early and ad-free right now on Wondery Plus. Intuition is based on experience, having been exposed to lots of things like this before. Someone gave me a report the other day, they were pulling some data. I was like, pull this thing. And they're like, okay, there was a thousand or something.

And I was like, no, there's not. And they were like, how do you know? I was like, I just know that's bullshit. I don't know what the actual number is, but I'm telling you there's some problem with how that segment was pulled. I know that it's higher. I don't know why I know, but, and so they went back and of course it was higher

and it's just because I've pulled many versions of similar reports before. And so I have a vague sense of the parameters where it probably should be. Now, one time out of 10, maybe it'll turn out that I'm actually incorrect and that is correct. But that sense of, I think being good at sussing out things that are obviously incorrect, things that don't add up,

or being able to spot bullshit, these are really good skills. Yes. I think they're gonna be especially important in an age of artificial intelligence, where I think people are thinking like these large language learning models are going to be like magic. And actually, they're just going to dilute everyone in more information and more data. And some of it's going to be good and some of it's not going to be good. And if you're not able to sift through what's good and not good, true or not true, you're just going

to get eaten alive. Like you already have, like, you know what I mean? Like people who are susceptible to bullshit are going to be victimized, misled, overwhelmed. And yeah, developing that ability to see through things to me is a really important trait. That's the definition of critical thinking. Yep. I'm kind of a relentless techno-optimist. I'm really excited about what AI can do for human productivity. Oh, I am too.

I'm just saying that it'll be great for people who know how to work with tools and know how to add human wisdom and critical thinking on top of it. And people who think that it's just gonna do stuff for them and they don't have to think about this anymore, you're gonna get in a lot of trouble. You know?

I mean, even like in the world of writing, like it can do a pretty good job writing stuff, but it can't do a great job. And so the ability to go from good to great, that's the skill. So if you're average, I think these things are gonna be hard for you. I'm gonna share with you after the program, something, I think these things are gonna be hard for you.

I'm gonna share with you after the program something that I think you'll get a kick out of. Which is I fed into Chat GPT, the entire manuscript of this book. Nothing else, just the manuscript. And I said, write a review of this book in the style of the Wall Street Journal was uncannily good.

Were you doing that in the feedback phase or you're doing it just to see what it would look like? No, the book was done. I mean, I was just playing around with AI. Yeah, yeah. No, I think the ability to use tools is our, that's the superpower of humans. You could have done that while the manuscript was still being written and then anticipated criticisms then anticipated criticisms and then address them in the book. To me, that's what you could be usable for. I mean, AI wasn't even quite at its stage then, but yes, that would have been very helpful. Are you going to do that in your next book?

So my next book opens with this story from Seneca where Seneca talks about this wealthy Roman who wanted to be seen as very smart. And so instead of doing the work, you know, reading a bunch of books, getting teachers, whatever, he purchases this group of very educated slaves, each one a master of the Odyssey, another a master of the poetry plays. And then he would just have these servants whisper in his ear whenever he needed to like answer a question or entertaining guests at a dinner party. And he thinks he's getting away with it. I'm sure you've met people who have done the equivalent

that you make a bunch of money and then you wanna impress people at parties and you wanna be cultured and smart. And so he thinks he's getting away with it until one of his friends comes up to him and says, this is a wonderful party. Have you thought about becoming a wrestler? And he says, a wrestler?

I'm an old man. And he says, oh, but your slaves are so young. And Seneca's lesson from this story is that no one becomes wise without doing a lot of work. That it's hard. It's difficult. And if you think there's a shortcut, if you think there's a secret, if you think there's a hack, if you think there's this tool, this AI thing is going to magically make you amazing at something, you're not just fooling yourself. You're fooling yourself in a way that people have fooled themselves for thousands of years. Yeah. No, I totally agree. There's a chapter in the book called Get Rich Slowly. And it

really, I mean, I think you can get rich quick if you're lucky, but it's a lot wiser to plan on doing it slowly. It's true, there are no shortcuts. There are ways of doing things a lot more efficiently. One of the stoic principles that really is very important in my life is controlling your time, realizing that time is our most precious resource and using it very, very consciously to live a purposeful life and not just fritter time away. Yeah, there's always things that you can do to be smarter, faster, better, but if you think you can skip ahead,

you're gonna get yourself in trouble. Like there's a Zen story about this kid. He goes to this master and he says, "'How long will it take to be a master?' And he says, you know, 10 years. And he goes, "'Okay, well, I'm gonna work really hard and really fast. I mean, this is gonna be the main thing. How long will it take?' And he says, you know, 10 years. And he goes, okay, well, I'm going to work really hard and really fast. I mean, this is going to be the main thing. How long will it take? And he says,

15 years. And he goes, no, no, no, you don't understand. I'm going to be super committed. I'm going to work super hard. I'm going to do this extra fast. How long? And he says, okay, 30 years. You know, if you think you can speed it up or that you can get something for nothing, it's going to take you longer than the person who is just, I think, willing to sit down and do the work and trust the process as opposed to try to outsmart or outmaneuver the process. Now you've gotta be, at least would work for me,

is being a serious student of anything I was trying to do. Yes. And just learning from people I met or if I go into some new business, learning as much as I could about it. The biggest business I built in my lifetime was this company, Delphi Insurance Company, and there's a chapter about that. But I was actively studying who succeeded most in the insurance business and how. And I was actively studying what's the culture of a successful enterprise. And it was a totally

different model. I was using the Rand Corporation, where I had defense intellectual place as a model for culture, while I was using a very successful insurance company as a model for culture while I was using a very successful insurance company as a model for strategy. But the point was, I was approaching it as a student. Yes. And in my whole life, I think what's worked for me is I approach almost everything I do, that's particularly anything new, as a student. I want to learn. Well, that's where ego gets you in trouble, especially if you have already succeeded at something, is that it makes you think that you know everything

or that you're just naturally brilliant. And that makes it hard for you to learn and understand a new domain because you're not coming to it as a student. Like Epictetus's line was, you can't learn that what you think you already know. And so if you go into it and you have a humility and an openness, you can get better and you can take in new information.

But if being a know-it-all is a self-fulfilling prophecy in the sense that it becomes impossible for you to know anything more, whereas the student can always learn more. There's a bit in Spinoza where he talks about self-esteem and he says rational self-esteem is really the golden mean here. If you overestimate your abilities, you're going to make rash decisions, you'll do heedless things. If you underestimate your ability, you'll demand less of yourself in life, you'll be an underachiever. So it's that if your self-esteem arises from the opinion of others, that's a very fragile basis for it as well. But if your self-esteem is rational.

Based on evidence. Exactly. That is what you should be striving for. Yeah, I like to say I don't believe in myself. I have evidence. And that belief in yourself to me is dangerously close to ego or delusion. You know? And this is why it's important to go out and do things. Like to try hard things, to have hobbies, to get out of your comfort zone is, is you're not just developing a competency

in whatever you're doing, you're also just developing competency and evidence of your own ability to start at something poorly and end up proficient at it. And that's like, that's probably why when you went all in on your business, it wasn't even so much the math that worked out, but your understanding that even if you did end up destitute, you still had skills and traits and relationships that you could build upon and use.

You know what I mean? Like you can lose everything, but they can't take away from you your determination, your creativity, your ability to learn, all these, those are sort of priceless. Exactly. A little bit of a controversial take here, I think you might have an interesting

take on it. I think Epictetus is the wealthiest of the Stoics, even though he's literally the poorest. Seneca talked a good game about these things, but at the end of the day, he's Rome's richest man or second richest man. And clearly some level of the desire to live the high life makes him complicit and caught up in Nero's regime. But Epictetus has a self-sufficiency to him. His desires are low enough that he's wealthy and can satisfy his needs, whatever his bank balance is. There's a story about Epictetus, a man breaks into his house and steals his like prized

possession, this lamp that he has, a silver lamp. And Epictetus says, that was on me. You can only lose what you have. And he goes the next day and he buys an earthenware lamp, like a clay lamp. His point being, you know, the less I have, the less can be stolen from me. And I think, I just think in that way, Seneca was afraid to lose his power and influence and money. And in a way, this cost him his freedom and his dignity. What do you think about that? Well, you probably know Seneca better than I do. But to me, at least what I took from reading

Seneca was that, I mean, I was fascinated that he was the richest man by repute in Rome. And of course, Marcus Aurelius was emperor when he wrote meditation. So, I love the idea that stoic philosophy was coming from people who were right at the very top and from the very bottom of the society, and it was the ideas that really mattered rather than where they were. But it seemed to me that Seneca was sort of saying that wealth could be an asset if it enables you to live a richer and fuller life. That material abundance can be an element of joy, can open up possibilities for you in life that are absolutely enriching, but it could also be a source of jealousy, it can be a source of fear that you're going to lose what you've got. And it's all in the way we think about it. If we think about material

wealth in a positive and constructive way, it can be a very good thing. But if you think about it again as kind of jealousy, comparing yourself to other people, fear of loss, then it can be a bad thing. So it's, again, it's this stoic idea that it's not the thing in itself, but it's the way we interpret it. Yeah. Seneca has an interesting definition of poverty. He says, it's not having too little, it's wanting more. Now, obviously, there is such a thing as real poverty. But I imagine you've met some very poor rich people. For sure.

Who have an inability to be satisfied, there's never enough, or they are endlessly comparing themselves to other people. Well, it's also a question of, I mean, my notion, at least of the well-lived life, sort of sees money or wealth as a means to an end. It's not an end in and of itself. It might enable you to hang out with people that you're going to learn from in politics or learn from in culture. In my case, one of the most satisfying things that financial success led to was the ability to be philanthropic. Because that seemed to me a fundamental idea of the well-lived life. But I took from my biographical role models like Carnegie and

Rockefeller the idea that philanthropy was not just writing a check. It was trying to build the institutions or create the institutions that you thought the society needed. Well, that's a hugely satisfying thing to do, but you need money to do it. Can wealth become an end to itself for some people? The things you own end up owning you. Seneca talks about how sometimes slavery lurks beneath marble and gold. You know, you have these expensive things and then you're worried about losing them. People buy a multimillion dollar house and then spend millions more renovating it and decorating it and showing off. Like, how easily does the wealth become almost a full-time job for people?

the wealth become almost a full-time job for people? Dr. like when I think of Carnegie, Rockefeller, Joe Kennedy, those were three that I talk about in the biography section. They were called robber barons. And to me, I mean, again, applying critical thinking, I thought of them as kind of heroes. They built great American industry, not Kennedy so much, but Rockefeller and Carnegie. But they also established what I thought was a great American tradition of philanthropy and this kind of active philanthropy, not just giving to poor people, but creating institutions in a society. And that gave them an opportunity to use their talents and their abilities for the greater good. And it's a basic stoic precept of Marcus Aurelius, that we should act for the benefit of society.

And to me, these guys were exemplars of doing that. So wealth is not a goal. Wealth is a tool that can help you achieve a well-lived life if you're being conscious. Marcus Aurelius, obviously a very wealthy man. You know, he talks about one of the things he learned from his mother, which I always thought was interesting. He says, my mother, her reverence for the divine, her generosity, her inability not only to not do wrong, but to not conceive of it, and the simple way she lived, not in the least like the rich.

But then he says he sort of gives his definition of wealth at the end where he thanks the gods for the sort of breaks that he gets in life. And it would be different, you know, inheriting an enormous fortune. It's not like he built a huge business or even ran for office. So I think he had maybe a greater sense than some people do today of the role that fortune had played in the fortune that he had, right? Which I think is great. Sometimes people are born on third base and then congratulate themselves

rating a home run as they say. But he says that whenever I felt like helping someone who was short of money or otherwise in need, that I never had to be told that I had no resources to do it with. And I was never need, that I never had to be told that I had no resources to do it with. And I was never put in that position of having to take something from someone else. I just think that's a great definition.

Well, to be able to be self-sufficient and not need to rely on the resources of others. So you're not a burden to anyone. And at the same time, to be free to help as many people as you see fit because you have an excess of resources yourself. That to me is a great way to think about it. You also made an interesting distinction between people who inherit wealth and people who create

wealth. Yeah. And it's just a fact that I've thought was kind of interesting that the philanthropists in America who've given more than a billion dollars away, all made their money themselves. People with inherited wealth, they sort of feel, well, this is given to me and I have sort of an obligation to give it to my children. They're a steward of this fortune.

You could think of them as stewards, you could think of that, or they could think of it as sort of, I have something that I don't quite deserve. But people who've built fortunes by building businesses, I think have contributed in a very meaningful way to society. They don't have to give anything back, quote unquote. Right. Because they pay a lot of people's salaries and yeah. To build a successful business, you have to contribute something to society, but you also feel like you've earned the money and that you don't, you can do with it what you think is right.

It doesn't come with a burden of, you know, my parents gave me this and therefore I have to give my children that. Yeah. And there's probably also hopefully an understanding that they made this, they can keep making money. Like an entrepreneur or an investor is maybe, hopefully, less, has less of a worldview that thinks there's a finite amount or that it's a set amount. I mean, like, Warren Buffett has obviously given billions of dollars away, but his sort of net worth seems to remain stubbornly around the same number because he's so good at what he does. And he made these decisions a long time ago that continue to pay off. For sure.

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