Ryan Holiday on the Case for Stoicism in an Age of Distraction

While the Greek and Roman philosophy of Stoicism has been around for millennia, author and media strategist Ryan Holiday is bringing its teachings to a modern audience by way of his popular books and his podcast, “The Daily Stoic.” He says ancient writings by the likes of Seneca, Marcus Aurelius, and Epictetus resonate in times that feel especially chaotic. Kara and Ryan talk about why young men in particular seem drawn to Stoicism and what powerful figures in the worlds of tech, MAGA politics, and the man-o-sphere get wrong about its teachings. He tells Kara their actions frequently run counter to Stoicism’s foundational tenet: our obligation and responsibility to — and with — other people. Questions? Comments? Email us at [email protected] or find us on YouTube, Instagram, TikTok, Threads, and Bluesky @onwithkaraswisher. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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

• 0:00Speaker 00

  I do think about Rome all the time, like Rome is my Roman Empire. It was the center of the world. It was the most powerful empire on earth. And so a lot of the predicaments and dilemmas that America is in, a lot of the forces acting on America are the forces that were acting on Rome, just as it was acting on, on the Greeks in the Socratic period.

• 0:32Kara Swisher?

  Hi, everyone. From New York Magazine and the Vox Media Podcast Network, this is On with Kara Swisher, and I'm Kara Swisher. The Greek and Roman philosophy of Stoicism has been around for millennia, since the ancient Greeks and Romans, obviously. Anyone who has read Meditations by the Roman Emperor Marcus Aurelius has had a taste of it. Generally speaking, Stoicism centers on the ideas of self-control, rational thought, and letting go of the things we cannot control as a means of living a better life. So maybe unsurprisingly, it's finding new resonance in a world where we've lost sight of some of these virtues. And one of the biggest evangelists right now is author and media strategist Ryan Holiday. He's written around a dozen books on the subject and has a website and popular podcast

• 1:14Kara Swisher?

  called The Daily Stoic, where he shares meditations, lessons, and interviews inspired by the great Stoic thinkers. And Holiday is willing to call out the ways tech leaders, MAGA politicians, and manosphere influencers are getting it wrong. I think it's important to talk about Stoicism right now, because one of the things that Silicon Valley companies I have covered over the years have done is perverted it in a way that I find distressing. And at the same time, it's a great way to think about your life and how you want to lead it. And we are at a perfect moment in all this chaos to do so. And I think Ryan is an excellent teacher at doing that. All right, let's get to my conversation with Ryan. Our expert question comes from my eldest son, Louis Swisher, who is a fan of the topic. This

• 1:56Kara Swisher?

  is a thoughtful conversation with a thoughtful person, so don't go anywhere.

• 2:08Speaker 02

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• 2:39Speaker 03

  I'm Anna Garten, and each week on Happy Hour, I invite new and old friends for a drink and a fun conversation at my kitchen table in New York City. On this week's episode, I'm joined by Julia Louis-Dreyfus. We talk all about attending a fashion show in Paris together, throwing dinner parties, and making her Broadway debut in other desert cities. New episodes of Happy Hour are available every Wednesday. You can watch on YouTube or listen wherever you get your podcasts. Cheers.

• 3:16Speaker 04

  Hey, guys. Cassidy Hubbard here. This week on Ann Mom, we spoke with three-time WNBA All-Star De'Arri Gahanbi about navigating pregnancy in the public eye, employer supports for expectant mothers in pro sports, and what it was like returning to the court after giving birth. Check out the latest episode of Ann Mom wherever you get your podcasts.

• 3:40Kara Swisher?

  Ryan, thanks for coming on On.

• 3:41Speaker 00

  Yeah, thanks for having me.

• 3:43Kara Swisher?

  So there's a lot I want to talk about, about modern Stoicism, its appeal to young men, how leaders in tech and politics are getting it wrong. My first clue, I have four kids, but two of the older boys were carrying around Marcus Aurelius suddenly, and I didn't know what was happening, although I was thrilled for them to do so. But to start, what do people get wrong about Stoicism?

• 4:03Speaker 00

  Well, I think that the word stoic is unfortunate in the English language, just as the word Epicurean is, right? We think an Epicurean is a pleasure-loving hedonist, and then we think a stoic is an emotionless robot.

• 4:16Kara Swisher?

  Right, grin and bear it, essentially, right?

• 4:19Speaker 00

  Yeah, which is not what either of the philosophies are about. So I think the stereotype as the emotionlessness is the big one. And then as Stoicism has become sort of popular again here in the 21st century, it's hyper masculine. You know, it's like the ChatGPT rendering of Marcus Aurelius has him absolutely shredded with a 12-pack. And so it's become this like anti-intellectual thing, almost, when in fact, as a philosophy, it's based on, on reason and virtue and decency and goodness and, and some, some big things that I think are missing in some of the popular conceptions of the philosophy.

• 5:00Kara Swisher?

  So they get that it's sort of the strong man kind of thing, like a strong silent type kind of thing?

• 5:06Speaker 00

  Yeah, exactly. I mean, look, Marcus Aurelius is the most powerful man in the world. There's, is the Emperor of Rome. I think there's a reason that that is attractive to young men in particular. It's different than the sort of academic philosopher. It's different than the, the nerdy philosopher. It's different than the egghead, you know, all these things. So I think there's an attraction there. The irony being that Marcus Aurelius, although he is the Emperor of Rome, is known in his time for how thoughtful and considerate and patient and all the, all the opposite of these things we're now projecting onto him.

• 5:40Kara Swisher?

  Absolutely. So let's then define what Stoicism and why I've seen the resurgence popularity. And again, you're not talking about the modern dictionary definition of the word Stoicism, which is to endure pain and difficulty without showing any emotion, the grin and bear it thing I was talking about. What you're talking about is a philosophy that goes back millennia.

• 5:57Speaker 00

  Yes.

• 5:57Kara Swisher?

  Give us the, and I hate to say Cliff's Notes version of the philosophy of Stoicism, but how you define it and how you're putting it out there in quite a popular way, speaking of popular.

• 6:08Speaker 00

  Yeah, it's interesting to think like Stoicism is an ancient philosophy to the Romans, right? It starts in Greece, you know, sometime around the 4th century B.C. It's rooted in, in cynic philosophy, first and foremost. But basically, this guy named Zeno suffers this shipwreck. He washes up in Athens totally penniless, and he starts talking about this philosophy as he's rebuilding his life on what's called the sto apo kilae. That's the painted porch in, in the agora in Athens. And so it's this philosophy that ultimately comes to be rooted around these four virtues of courage, temperance or moderation, justice and wisdom. And it makes its way ultimately from Greece into Rome. But as a philosophy, I sort of summarize it as it's this idea that we don't control, you know,

• 6:52Speaker 00

  much of what's happening in the world around us, but we control how we respond to the world around us. We control who we are inside that world. And so you can imagine Zeno coming out of this disaster, living in a Greek world that's constantly at war and in this state of flux, and then ultimately the Romans. You know, so much was outside of their control, you know? Most children died in infancy. You could be thrown in jail by a tyrant. They couldn't predict the weather. There were plagues. Like, the ancient world, although we, we see it now as this kind of golden age, was a horrible place to be alive, a violent, dark, disturbing place. And so a philosophy that said, okay, well, inside

• 7:34Speaker 00

  all of this, what's up to me? Where should I focus my energy? How can I both survive and thrive inside that? That's what the philosophers were, were thinking about then, as opposed to, you know, how we think about philosophy now, which is, you know, so removed from the day-to-day-ness.

• 7:51Kara Swisher?

  So how to cope? I mean, like, like you just mentioned, the four foundational values are, as, as you say, courage, discipline, justice, and wisdom. Can you apply those today, you know, even with yourself, as a way of explaining what they are and how they intersect? Because intersection is critical for all four of them.

• 8:08Speaker 00

  Yeah, Zeno would talk about how the, the four virtues are distinct and yet inseparable from each other. I'll, I'll give you a great example. So courage, we, we know what courage is. It's running into a burning building. It's also the moral courage to stand up and speak out. But courage, inseparable from the virtue of justice, that is to say, in pursuit of the right, in pursuit of the good, is obviously not a virtue. And so they all inform each other. Discipline would be not just, you know, what time do you wake up? What do you eat? How, how fast can you run? Discipline is also rooted in the idea of temperance or moderation. What is the right amount? So, so even Aristotle was talking about how, you know, too much courage becomes recklessness, and not enough courage is, of course, cowardice.

• 8:53Speaker 00

  You know, YOLO-ing everything isn't courage, it's just wildly irresponsible.

• 8:59Kara Swisher?

  Right.

• 9:00Speaker 00

  And then all of the virtues are then informed by the virtue of wisdom, which we could say is sort of discretion and judgment. It's not just like how smart you are, but it's your understanding of things, the value of things, the truth of things. So all the virtues inform each other and are, are difficult to separate, but you can't really have one without the other.

• 9:22Kara Swisher?

  Did you have some, point to something in your own life recently where you were trying to balance them out?

• 9:27Speaker 00

  Ooh, I mean,

• 9:30Speaker 00

  I'll give you a good one I struggle with with discipline. I, and this sounds like, you know, my, my problem is I just care too much. My, my problem for, for like, like, I love, I love exercise. I love, I love working out, I love running. For me, it's harder to go, hey, like, my ankle hurts today. So, so the discipline for me is I'm going to rest and I'm going to recover and take care of myself as opposed to pushing myself and injuring myself further. So like, the, the discipline there, it's not always pushing to do more. Sometimes it's pushing to do less. I have two young kids. So for me, the, the discipline that I think about the most is just the, do I need to get upset about this? Am I keeping my cool here?

• 10:13Speaker 00

  How am I expressing myself both firmly and reasonably? So, so I would say I, I deal with the, the virtue of sort of, maybe the best way to describe discipline in, in the Stoic concept is the idea of self mastery, right? Not being a slave to your passions, not being a slave to your urges, not being a slave to your emotions, not being a slave to, you know, your first reaction to things. So that's probably the, the day to day one that I'm thinking about the most.

• 10:41Kara Swisher?

  That's a good one. I'm very disciplined. I didn't run this morning. I'm like, I'm tired, tired as fuck and I'm staying in bed. I'm very disciplined about that. Again, we're talking about a philosophy that dates back to before the birth of Christ. And yet your, your YouTube videos and podcasts are hugely popular, millions of views. You've said the interest in Stoicism seems to pick up when the world feels out of control. And you were just talking about the chaos of the ancients. Do you think that's what's happening now? Or, or is it linked to that in your mind?

• 11:08Speaker 00

  Yeah, I mean, look, one of the great Stoics is Epictetus, who is, actually, two of the great Stoics. We have Epictetus and Seneca, both lived through the reign of Nero. So you can imagine Seneca and Epictetus turning to Stoicism when they're like, the guy in charge is insane. And there's not that much we can do about it.

• 11:28Kara Swisher?

  Epictetus was a slave too.

• 11:30Speaker 00

  Yeah, Epictetus has been slaved. He spends the first 30 years of his life as a slave. It's really interesting just how much of the social spectrum the Stoics end up taking up. You know, we have Epictetus on one end of the social spectrum. And then he's the primary philosophical influence on Marcus Aurelius. You know, Marcus Aurelius lives through a plague. He lives through these wars. I do think like, when everything is awesome and everything is going well, you know, it's a little easier to be an Epicurean. It's, it's when it feels like things are changing fast. It feels like they're falling apart when the political system isn't working. Like, what do you do when you wake up and the world is filled with injustices and cruelty

• 12:15Speaker 00

  and stupidity and corruption? And you know that it's wrong and you would like to think that everyone agrees with you that it's wrong. But that's actually a minority view. You know, I, I think there's a, a reason that the Stoics are resonating today. But it's worth going back and thinking, you know, 250 years ago, at the time of the founding, the most popular play in the world is this play called Cato by Joseph Addison, which is all about Stoic philosophy. And all the founders know it by heart, like in the way that we could sing lines from Hamilton today. George Washington is quoting lines from Cato in his letters. He puts on Cato at Valley Forge. So it's in the, you know, the times that try men's souls that, that I think we turn to

• 13:00Speaker 00

  our forebears who, who went through difficulties and, and we try to go, well, what did they figure out about getting through this? And, and I think Stoicism has long been that.

• 13:09Kara Swisher?

  Absolutely. There's also a lot of overlap with Stoicism and the three Abrahamic faiths, Judaism, Christianity and Islam. And church attendance seems to have at least flatlined after decades of decline. Oddly enough, one of my other sons is going to church every week now. And we never took him to church, which I'm very supportive of. Do you see this as part of that trend? To me, it's community is what he's searching for, or, or non-online life, I guess, something like that, or real life.

• 13:37Speaker 00

  I think, I think community is part of it, but I, I also do think spiritual guidance and moral direction is something we are thirsting for. Like, you, you take church out of public life, you take moral instruction out of school because we don't want to be judgmental, we don't want to yuck anyone's yum. We want to look at history and, and go, well, this person was a slave owner and this person was a tyrant and this person was a this and a that. And all of that is well and good, but what it does create is a bit of a vacuum. Like, who should I look up to? What is good? What is evil? How should I live my life? I, I think particularly for young men, there is a hunger for direction.

• 14:22Speaker 00

  I think of all the faiths to have a resurgence, you know, Catholicism is interesting. And, and, and I do think, you know, I grew up Catholic. So there, there is something about Stoicism that I think is resonant there. They share the same cardinal virtues. I just think people are, they know that what they're doing isn't working for them, but it's not totally clear what would work better. And we often look to the past to, to answer some of those questions.

• 14:49Kara Swisher?

  There's also some attraction to this Pope, I think, and the previous one. I think that's one thing, which is it's just interesting because I never took them, took them to church. Never did. I happen to be Catholic. I never, I haven't been to church in a hundred years. But, and again, I'm, I'm very supportive. I'm like, great, this is, makes you feel better. It makes you feel like you can cope. It gives you direction. It makes him more rounded. Great, this is really good for you. It, it seems very good.

• 15:12Speaker 00

  Did you read the Pope's thing on AI, his essay?

• 15:14Kara Swisher?

  Of course I did. I did a whole show on it. Yeah, what did you think of that? Magnificent humanity.

• 15:19Speaker 00

  I, I thought it was so fascinating because, you know, for my whole life, but, but I think for a generation or so now, we've been looking at this technology and then asking ourselves, is it economically good or bad? Is it unavoidable or not? And what's so interesting about that work is, is you have him looking at it from a moral perspective. Like, is this right and wrong? Is this the direction we want to go as a society? How will this change our obligations to each other? What are our obligations to each other? So I do think it goes to that idea of like, we just live in this, unfortunately, I think, like a fundamentally amoral society where we have stripped out the ability to, to even ask those questions about like, is this right or wrong?

• 16:03Speaker 00

  Should I be doing this or not? It's just like, hey, can this get funding or not? Will this go viral or not? And I think the Pope is, is sparking something there, which I think great philosophers and spiritual leaders are supposed to spark, which is go like, hey, that's all well and good, but there are some other questions to consider here. And, and these are in fact, the most essential questions to consider.

• 16:25Kara Swisher?

  It's also not anti-tech, actually, if you read it carefully, if you read every word. And that's what I thought he did and really, I wonder if the Pope is a Stoic. He feels a little bit.

• 16:35Speaker 00

  You know, I was just in Rome and, and we went and saw Blessing of the Pope. And you see him going around in the little Pope mobile. And it, it was funny, you know, they, they'd be like, oh, you're American. You're like, Bob from Chicago. Like, the idea of the Pope being a human being that's accessible to Americans is interesting. I like to point out that, that Marcus Aurelius and the Pope have, have the same title, pontifex maximus. That Rome absorbs, Rome as the Catholic Rome absorbs so much of the iconography and the, the names and the words and the titles of, of the Romans and then the Stoics. This sort of continuity is interesting to me. But yeah, I thought the work was really interesting and I just wish we would, I wish we were having those

• 17:20Speaker 00

  kinds of discussion. I think this is what's really great about the Odyssey. Like, I hate that so much of the dialogue about the Odyssey is, is about like, who should have been cast? And, you know, this or that. But, but the Odyssey is supposed to be contentious and create debate. And, and Odysseus is, is a hero and a villain for, for the purposes of spurring.

• 17:43Kara Swisher?

  He's a complex man.

• 17:44Speaker 00

  Yes, it says it right there in the first line. That's the whole point is you're supposed to, to argue at these different ways and then make different choices in your own life.

• 17:55Kara Swisher?

  100%. We're, we'll get to tech in a second, but every episode we get a question from an outside expert. Here's yours.

• 18:01Speaker 05

  Hello, my name is Louis Swisher. I'm Kara's eldest son. And like many young people, I've found comfort in the words of Marcus Aurelius and Seneca. But I do wonder, what is the purpose of a philosophy of self-regulation in a modern world that incentivizes self-excess and indulgence?

• 18:17Speaker 00

  Ooh, that's a great question. I love, I love that.

• 18:21Kara Swisher?

  Yeah, I raised him right.

• 18:22Speaker 00

  Yeah. I mean, the Stoics were thinking about this themselves, right? So Marcus Aurelius can do anything he wants, right? And we know, we can guess at what some of those things might be based on the behaviors that we know from the other emperors. Like, they were remarkably creative at the excesses they figured out how to go to. So Marcus Aurelius could do all that. But I think what he realizes is that that's a, actually not freedom, but a kind of a punishment. That, that Tiberius isn't actually having a good time on this pleasure island that he's, you know, throwing people off of cliffs when they fall out of favor with him or whatever. That, that this is, that this sort of excess is a kind of a prison.

• 19:05Speaker 00

  And so the idea for the Stoics is like, not whether you can or can't, but whether you should or shouldn't. And I think in a way, it's remarkable that, that your average person in America 2,000 years later could relate to the luxuries and temptations of, of a Roman emperor. But that is how fortunate we are as a society, right? And, and that we have a, a level of choice and agency that would be unimaginable, not just to the ancients, but even to people a couple of generations ago. So it then becomes imperative on us to go, well, how should I live? What should I do? And what kind of person do I want to be? And so those are the questions that we have to ask. And, and the answer becomes, what kind of life do you want to live?

• 19:50Speaker 00

  Do you want to, because you're free to do anything, actually become a slave to whatever your impulses are? Like Epictetus looking around at Nero's court, even though he's literally enslaved. I think what's striking to him is that he's actually freer than many of these people. Like, he, he tells, one of my favorite scenes, he, he sees this guy sucking up to Nero's cobbler to win favor with the emperor. And he goes like, this guy's to blow smoke up the ass of a guy who makes shoes because he doesn't want, you know, to lose favor with this deranged emperor.

• 20:23Kara Swisher?

  Yeah, that sounds familiar.

• 20:24Speaker 00

  It does, it does, right? It's like, do I want to go to the Melania premiere? And, and you go, okay, if a billionaire can't say no to doing something that they obviously don't want to do. Is it actually that great to be a billionaire?

• 20:40Kara Swisher?

  Correct.

• 20:41Speaker 00

  I'm sure it's great. Is it, is the billionaire as powerful as you think they are? And the answer is no, because there's things that they can't not do.

• 20:48Kara Swisher?

  Yeah, we'll, we'll get to these billionaires in a second. It's, it's sort of like the, why would you have fuck you money if you can't say fuck you?

• 20:54Speaker 00

  Totally.

• 20:55Kara Swisher?

  Essentially, right?

• 20:55Speaker 00

  Totally.

• 20:56Kara Swisher?

  And, and to me, it's more like, I always think, I did a podcast on succession. I call them cashmere prisons, right? They're in prisons. When I, and then when I look at a lot of the tech people, I'm like, I can leave, you can't. You're a cashmere prison. Like, you have so much stuff around you now, you can't move. And I feel much freer. But how do you grapple with the idea that Marcus really is, of course, was a dictator? If you can apply that to our modern era.

• 21:22Speaker 00

  Mm hmm.

• 21:22Kara Swisher?

  He had every choice. But I guess we're like that, too. We have every choice, or at least in the United States.

• 21:27Speaker 00

  I, I, I like to think of, of Marcus a little bit like, uh, Thomas Jefferson. You know, he said, all men are created equal, but we have to take him literally, even though he probably didn't mean it. There's an interesting passage at the, at the beginning of Meditations where Marcus really says, I encountered Thrasia, Helvidius, Cato and Brutus, and conceived of a society of equal laws governed by equality of status and of speech, and of rulers who respect the liberty of their subjects above all else. So I like the idea of it. And then it's hard to escape the fact that Rome had ceased to be a republic and it's now this, this empire. Um, he doesn't choose this, doesn't, how much can he change the system? I don't know.

• 22:12Speaker 00

  I, I'm fascinated by the moral predicaments that these philosophers get themselves into.

• 22:18Kara Swisher?

  Yeah. I owe slaves and yet I'm asking for freedom.

• 22:21Speaker 00

  Yeah. And, and look, it's easy to, to talk about it from where I sit or where a Harvard professor sits, where you don't have the same ethical conflicts because you're not actually in the arena, like literally or figuratively. So I, I like that the Stoics were involved to a degree that their philosophical principles are being tested. Um, I don't like that they didn't always pass these tests, right? Like Seneca would, would be a familiar character in our era in that he starts off as Nero's sort of governor and teacher and guardrails. And towards the end is widely seen as his enabler and doesn't break with him until far too late. So I have no problem criticizing the Stoics.

• 23:04Speaker 00

  I have no problem putting them up and analyzing their moral predicaments. I just, I think ultimately, uh, the game should be thinking about, you know, what choices are we making in our own lives that give us evidence that if we were thrust in such a position, we would do anything differently?

• 23:25Kara Swisher?

  Yeah. How often do you have to think about the Roman Empire? Because the relationships you can make very easily between now and then.

• 23:31Speaker 00

  I mean, uh, uh, look, our, our system is based on Rome. They're called senators because that's what they were called in Rome. It's called the capital because in Rome, there was Capitoline Hill. Like, we are living, we are living in a system designed by people who are cosplaying as the Greeks and Romans. And, and so I, I do think about Rome all the time. Like Rome is my Roman Empire. Um, and I, I love it and I find it endlessly fascinating. It's also just there. It's like, it was the center of the world. It was the most powerful empire on earth. And so a lot of the predicaments and dilemmas that America is in, a lot of the forces acting on America are the forces that were acting on Rome, just as it was acting on, on the Greeks, you know, in the, in the Socratic period.

• 24:16Kara Swisher?

  And the British.

• 24:18Speaker 00

  Yeah, sure. I mean, the reason you study history is to understand the present. And I think that they have a lot to teach us, both good and bad.

• 24:29Kara Swisher?

  We'll be back in a minute.

• 24:39Speaker 06

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• 25:09Kara Swisher?

  I'm Kara Swisher and I like people who say the quiet part out loud. In fact, I love it. That's Tiger Sisters, a new podcast that recently joined the Vox Media Podcast Network. Cherie Brooke Lu and Jean Lu are real sisters who built their careers at LinkedIn and Goldman Sachs. On their weekly podcast, they're giving the next generation practical tips on how to get ahead, how to write emails people actually answer, how to make your LinkedIn profile stand out and how to keep learning as an adult. It's straight talk about money, career and relationships every Monday. Follow Tiger Sisters wherever you get your podcasts.

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• 26:28Kara Swisher?

  So as we noted, Stoicism has gained a lot of popularity with young men today. There's been much written about the ways young men, in particular, are struggling in modern society. Scott, my partner on Pivot, writes and talks a lot about this. So it makes sense that young men would turn to Stoicism as a means of finding resilience and strength. It's either that or peptides and tea, I guess. Um, but can also be warped into a more problematic message of be tougher, hide your feelings, or that it holds secrets to becoming rich and powerful. Um, be, be very clear with people. Um, what does it says about what it actually means to be a man for people who sort of take it and use it for whatever purposes?

• 27:07Speaker 00

  Well, one of the most interesting pieces of, of writing, or I guess it was speaking, uh, that, that survives to us as a little essay is from Musonius Rufus, who's the teacher of Epictetus. And he asks, should women be taught philosophy? And ultimately where he comes down is the idea that virtue is virtue. It doesn't matter if you're a man or a woman. You know, he says like, you don't really care what the sex of your hunting dog is, just whether they do their job. Um, or, you know, is the horse fast or not? That's all that really matters. And so although Stoicism, because the ancient world was inherently patriarchal, 95% of the Stoics we know about are, are men. And a lot of the metaphors are wrestling and fighting and, you know, things women

• 27:52Speaker 00

  weren't allowed to do. That being said, um, there were plenty of Stoic women. One of the most impressive Stoic women in history is, is Cato's daughter, Portia, who, um, assassinates Julius Caesar with her husband Brutus, uh, though she gets sort of short shrift in, in both Shakespeare and, and the Plutarchian histories of it. Um, I guess what I'm, what I would say is that Stoicism does talk a lot about being a man, but it primarily talks about what it means to be a good person. Like what are obligations as a human being is as a member of society, of which I think, uh, obviously being a man or a woman is, is a part of. So I, I, I do think there's this like sort of over, overemphasis on what it can teach young men.

• 28:33Speaker 00

  Like, I know from my talks that like, uh, a good chunk of the audience is, is women in positions of leadership. It's not like women are not stressed out and overwhelmed and dealing with things. Like, of course they are. So, um, I, I don't want it to be a particularly gendered philosophy.

• 28:49Kara Swisher?

  You know, you found Stoicism as a young man across those lives. You were in early twenties. You were director of marketing for American Apparel. It faced many PR crises under its problematic founder, Doug Charney. What a job. And in your first book, Trust Me, I'm Lying, which I, I read, I liked a lot. You admit to using some pretty unseemly publicity strategies to generate buzz. Is that what brought you to it? Like, what the fuck am I doing?

• 29:14Speaker 00

  It's one of those things where it, it takes a while to sort of get its teeth into you. I think the reason that young men are attracted to Stoicism is that it speaks so clearly about mastering your emotions, about, you know, fulfilling your potential, about being great, about accomplishment. It is a philosophy that can make you stronger and faster and more productive and tougher and, and all these things that I think young men are particularly after. So if that's the, the way in, I'm all about it. And that was certainly the way in for me. I, I was thinking like, hey, how does this make me better professionally? Um, it took a good chunk of my twenties for the ethical framework of the philosophy

• 29:59Speaker 00

  to trickle all the way down. And for me to see that actually these things are related to each other, that they're equally essential. So I, I think as a motivational philosophy, the entry point is often there, um, which is good. You know, I, I mean, the early stuff that even someone like Jordan Peterson was talking about is great. You know, make your bed, read the great books, you know, find your purpose. All that stuff's really important. The, the problem is, uh, when that gets yoked to sort of grievance politics and stuff.

• 30:32Kara Swisher?

  I call it the grievance industrial complex.

• 30:35Speaker 00

  Totally.

• 30:36Kara Swisher?

  So what, what motivated you? What got you there to actually start living Stoicism as opposed to chewing on it in your head like that?

• 30:42Speaker 00

  Yeah. I, I mean, watching somebody destroy a billion dollar company because they were a slave to their appetites and their ego was quite eye opening, you know? I, Doug Charney built an incredible company that was making the world a better place. Like, a garment worker should not work for 50 cents an hour in a sweatshop in Guatemala, especially when that T-shirt is being sold for $50, right? Like, he, he used to say, like, you can't make a bikini for $6 without fucking somebody over. And he's totally right. You know, like, the, so much of the fashion industry is built on exploitation and people make millions of dollars for it, but it comes at the expense of the workers. It comes at the expense of the environment, comes at the expense of all these things.

• 31:25Speaker 00

  So, so I very much believed in that company and I was very inspired by it and I, I loved it. And then watching him destroy it, to, to, to choose, you know, he could have walked away. They, they offered him a bunch of money that said, look, you basically took this thing as far as you can take it and it's not going well. The stock price is 70 cents. Like, we gotta bring in some adults. And he was like, I'd rather burn it to the ground. And so to why?

• 31:52Kara Swisher?

  I know. Yeah.

• 31:53Speaker 00

  Right. Watching somebody do that, I think it, first off, again, we talked about the timelessness of these things. Like, that character exists in all sorts of works of history and literature. And so to watch that, I think it was eye opening. And I never was part of the sort of the scene of that company. My wife and I have been together for 20 years. I didn't go to the parties or do any of that stuff. But just realizing that that sort of chaos and dysfunction and megalomania was ultimately like it, it always ended in the same place was, was for me, a really powerful inoculation against Trumpism is a powerful inoculation against some of the Silicon Valley-ism, the Elon Musk-ism. It's like I've, I've seen,

• 32:38Speaker 00

  I saw a microcosm of this.

• 32:39Kara Swisher?

  When you were, yeah, no, absolutely. Now, in your interview with comedian Hasan Minaj, you talked about the thing that Marcus Rilis wrote about most was the common good and how Stoicism is inherently a philosophy about our obligations and responsibility to other people.

• 32:53Speaker 00

  Yes.

• 32:54Kara Swisher?

  But as we were talking about earlier, and our tech and social media puts a premium on the opposite, on the individual, on self-projection, on performative behavior. And it's turned us all into marketers ourselves, our personal brands. Talk about how you counsel young people about the way social media takes us away from that. It's the opposite direction of Stoicism.

• 33:14Speaker 00

  Yeah, it's like a recipe for being a hyper sociopath. Like, it's, it's like, hey, let me take your worst impulses and exaggerate them and incentivize them and monetize them. And I, look, I do think this is why mentally ill people do so well on social media. Like, they lack some of the restraints and the shame that is a kind of a final check on some of our worst behaviors. They can fully turn themselves over to the algorithm in a way that I don't, I don't think the rest of us can. What I love about Stoic philosophy is that ethical core that we're talking about, that it says, you know, there's a great passage

• 33:57Speaker 00

  in Meditations that I've been thinking about lately. Marx Rilis is talking about like how everything is going wrong and it's sideways. And he says, you know, I was once fortunate, and then at some point, fortune abandoned me. And then he says, but, but that's not true. We make our own luck. He says, like, we make our own good fortune. And so you might think he's about to say, you know, like this pull yourself up by your bootstraps, kind of make your own luck. And he says, like, good luck and good fortune is, is good actions, good character, and good intentions. And so you, you think about what a refreshing frame of reference that is for someone who has power and responsibility over a lot of people. And then you sort of compare that to the model we have today, whether it's

• 34:40Speaker 00

  political or, you know, economic, we're talking about the leaders of big companies. Like, this transition towards like, hey, my fundamental obligation is to shareholder value, or to my investors, or to scale, or to my own, you know, my own self-interest. You see just how fundamentally distortive that is.

• 35:01Kara Swisher?

  Now, what's interesting, though, at the same time, I think about this a lot, how to reconcile the inherent tension, myself, and you would probably have the same thing, you're growing your platform, so am I, and making money, in no small part to social media, and you have millions of followers. Talk about how you reconcile that, because I don't think all of it is bad, for sure.

• 35:21Speaker 00

  No.

• 35:21Kara Swisher?

  But it does, it does incentivize, as you said, narcissism.

• 35:25Speaker 00

  And look, like, book publishers are multi-billion dollar companies, selling through multi-billion dollar companies, selling through multi-billion dollar companies, moved by multi-billion dollar trucking companies. Like, there's really no way to sort of operate in this world or in this system with totally sort of clean hands. Like, you're always going to be dealing with unsavory trade-offs or dilemmas. So I think that's part of it. The thing I get a lot is people go, well, what would Seneca think about, you know, you doing this or that? I go, look, Seneca inherited wealth and lived on an estate tended by his many slaves. Like, there is something fundamentally more honest and decent about our system where you make something, and if someone likes it, they purchase it under their free will.

• 36:09Speaker 00

  And if they don't like it, they can get their money back or not purchase it. Like, I, I do think, like, the, the sort of world of commerce is not inherently in conflict with, you know, art or the exchange of ideas. So I, I don't have a problem with, with making money or working on these platforms. I think about, am I contributing a positive message? Am I carrying water for people that shouldn't have water carried for them? Am I providing intellectual cover for bad things? I, I think more about that. Like, I, I don't think about so much of like, what platforms am I on? I think about what ideas or people

• 36:52Speaker 00

  am I having on my platform? Like, I've had, the number of friends I've texted that said, look, I realize this episode will get lots of downloads, but you don't have to have RFK Jr. on your podcast. Like, you don't, there's no law that says you have to interview this person. And in fact, you should think about, when you are interviewing him, you know, what message you are allowing him to propagate into the world. Like, you can't silence him or shut him down, but you can decide not to contribute to the propagation of fundamentally horrible ideas.

• 37:25Kara Swisher?

  We'll be back in a minute.

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• 38:34Kara Swisher?

  So like we've been talking about, a lot of major figures in tech, maga politics, and the manosphere claim the mantle of Stoicism. I have listened to them. But you correctly say they get a lot of things wrong. They did a similar dance around Yuval Harari, who surprised them by thinking they're awful in many ways. You have said, you said there are worse things these tech people can study than Stoicism. But in tech, we'll embrace the philosophy. It feels like it's been stripped of its essential parts, like courage and justice. Talk a little bit about that, because they, they feel betrayed by some, they definitely are betrayed by me, and I have betrayed them. But you, talk about you. Yuval went under this, Sam Harris had this moment with them.

• 39:16Speaker 00

  Yeah, I, I have been slowly removed from all the group texts that I was once on. And, and some of the, the conference invites have certainly evaporated.

• 39:27Kara Swisher?

  That's a favor to you. Yeah.

• 39:29Speaker 00

  It's, it's been weird. I don't feel like I've changed that much. And, and it's been interesting to watch people radicalize. Like, I talked about this in the book I did on wisdom, like, watching Elon Musk go from reading Soviet rocket manuals to, like, getting all his news from, from social media. You realize just how easily smart people can fry their brains. And I think that's kind of the main problem of our time, is like, how to avoid getting brain fucked. And watching some of these people.

• 39:57Kara Swisher?

  That's your next book, Brain Fuck.

• 39:58Speaker 00

  Yeah. Watching, watching some of these people who are incredibly smart, who have had all sorts of interesting intellectual conversations, just like, say the most deranged things. And to say them sincerely is, is almost the most alarming part.

• 40:14Kara Swisher?

  With certainty is the thing. You know, I always say they're frequently wrong, but never in doubt. Like, one time, Mark Zuckerberg was talking about the First Amendment, and I was like, that's not what it said. Like, like, did you read it? It's short. It's really easy, kind of stuff. And so it's often that case. So if Marcus Rilis or Seneca walked through Silicon Valley today, what would they make of the kind of Stoicism practiced by some of these elite figures? Because they do think of themselves that way. They actually do.

• 40:39Speaker 00

  Yeah. It's, someone tweeted a couple of years ago, it was like, every athlete wants to be a VC, and every VC wants to be a Stoic philosopher. And again, there's worse aspirations than being a philosopher. But ultimately, I think, the most important philosophical questions are not the things they're hammering out on these group texts or at these dinner parties that I'm sure you used to go to as well, where they would talk about things.

• 41:07Kara Swisher?

  I did.

• 41:08Speaker 00

  The interesting philosophical question, this is what I love actually about having a business, about being an entrepreneur, is that all of a sudden, theoretical or abstract issues are decisions you have to make. Like, you have to decide whether you want to be on this platform or that platform, whether you want to do a deal with this company or that company. What advert, like, I don't, I don't accept gambling advertising. I don't accept alcohol advertising. I don't accept weed advertising. This, you know, cumulatively will cost me ultimately millions of dollars over the course of my life. And so, to me, the, the philosophy and philosophy in general is about the dilemmas and situations we find ourselves, particularly where there's money on the line, or status on the line, or access

• 41:49Speaker 00

  on the line. I think what's been fascinating to me and also disappointing to me with the Silicon Valley people is with billions of dollars on the line, and real questions about national security, about the future of our democracy, they've all made the decision about what's good for, you know, the, the investors in VC Fund 17, or whatever it is that they just raised money for, and not, like, hey, what kind of worlds do I want my grandchildren to live in?

• 42:18Kara Swisher?

  What would you, when you think about why they've become this way, and I'm just using technologists, because they're the current power, right? They're the current power. Why do you think that is? And what would change if they actually did follow these principles? I'm thinking of someone like Peter Thiel or Mark Andreessen. Now, Thiel is not a Stoic. In fact, he's criticized Stoicism at times for being too passive. Andreessen has occasionally talked about it, but also infamously said he practices zero introspection. This is not true. This is a lie. Talk about how it would be different and why they're practicing it the way they are. But they seem attached to it in some fashion at the same time.

• 42:54Speaker 00

  Yeah, it's probably worth stipulating there's not a single American industry that has distinguished itself particularly well in the particularly the the second Trump era as far as living up to these philosophical principles.

• 43:06Kara Swisher?

  Yes.

• 43:07Speaker 00

  But I trace it back a little bit to when the media turned hostile on tech. They took it very personally.

• 43:17Kara Swisher?

  They did.

• 43:18Speaker 00

  And they all kind of hunkered down in this bubble and created their own media ecosystem that's actually not that dissimilar to Trump itself, which is like, I don't think they're all living in reality. Like, sometimes when I see some of these extremely bad takes, they remind me of things that I heard when I used to get invited to the dinners that reminded me of bad takes that they would say at the dinners. But when you looked around and everyone there was on their payroll or wanted a deal of some kind, no one would go like, that was spectacularly dumb, or that is, that's not just politically incorrect, it's like, it's mean, and it's offensive, and it's stupid.

• 43:56Kara Swisher?

  I have to say, I've been in those rooms, and I actually would say, that's stupid. And then people would stare at me. And I, because it drove me insane. And then I stopped going, because it was like pointless.

• 44:06Speaker 00

  Totally.

• 44:07Kara Swisher?

  Now, you're an outspoken critic of President, but you say you're not out here to be a regular political commentator. How do you decide when to use your platform for political criticism, when to use restraint? You could very easily just stay in Stoicism.

• 44:21Speaker 00

  I could, except, you know, the Stoics are all involved in politics, right? Like, it is hard to be philosophical or ethical and then just simply tune out what's happening in the world. So I think it's, I don't know about you, but I find it particularly obnoxious when people get mad. They say, why do you have to get political? And I go, you know, I'm not talking about like, the House budget, or, you know, state referendums. I like, I don't talk about these policies. I talk about where politics intersects with the most basic parts of the social contract, or with the most basic obligations that we have as human beings. Like, I don't know how you can say, sure, the government is running around with masked

• 45:03Speaker 00

  agents in unmarked cars and throwing people in concentration camps and then deporting them either to foreign gulags or countries they've never been to before, and go, well, look, I write about personal philosophy, and that's just not my pack, right? Like, I just, I don't know.

• 45:25Kara Swisher?

  Yeah, yeah, yeah, I get it.

• 45:26Speaker 00

  What is the point of having a platform if that's not the line that you draw about what you're going to speak up? Especially as a grandchild of immigrants, people who came here as refugees, like, look, everyone should pick their issue, the thing that resonates with them. But I do think there are some things that no one is excused from.

• 45:47Kara Swisher?

  Commenting.

• 45:48Speaker 00

  Commenting on, completely. And commenting is only the start, right? Like, you also have to be involved locally and as a citizen, too.

• 45:55Kara Swisher?

  But has it, do you feel like it's cost you? I don't think it's cost me at all. I think the cost is fine.

• 46:00Speaker 00

  It's, it has certainly cost me people who would have, who disagree with me on those things, right? But like, one of the realities of having a newsletter, having a podcast, having social media is like, do you have the audience, or does the audience have you? And I think this, this goes to the Stoic idea is like, you look, you could have 10 million YouTube subscribers, or newsletter subscribers, or whatever, and then, is that something that frees you to say what you think is important? Or is that something that constrains you from saying what those people might not want to hear? And then you go, okay, well, actually, is this person, is that a form of power, or is it a form of slavery?

• 46:44Kara Swisher?

  Right, yeah, I agree. You talk a lot about that Stoicism is ultimately a call to get involved, not just accept things as they are. Give us an idea of what that looks like in practice, from your point of view.

• 46:53Speaker 00

  So there's this idea that Stoicism is about not being affected, right? Like, not being affected by what's, what's happening. And, and I think we can stipulate to that, if by not affected, we mean, in corrupt times, you do not become corrupted. If, in times of cruelty, you do not become cruel. In times of mass distraction, you don't get distracted. You know, if you're able to maintain your moral compass, your decency, your goodness in a fundamentally indecent, screwed up, broken world, then that's great. I think it was Montaigne said, you know, the, the job is to remain human in an inhuman time. So I think first and foremost, that, that's really important.

• 47:36Speaker 00

  And we're, I don't know about you, but I talk to people I know that are like, I can't write, I'm just so upset about what's happening in the world. I go, you're letting them win, like you are.

• 47:46Kara Swisher?

  Yeah, that's nice. Same thing.

• 47:48Speaker 00

  If they came in and tried to physically prevent you from writing, you would see that as, as textbook oppression. But if you just let the vibes get in your head and prevent you from doing your work, then that's, in a way, it's even worse. And then I think practically, like, how involved are you other than just talking about things on, on social media, you know?

• 48:09Kara Swisher?

  Hashtag-ism, right?

• 48:10Speaker 00

  Yes, yes. Like, have you actually been to a protest? Do you actually vote? So I think it, it's about being involved. Like, unless something is preventing you from being involved, like, your parents are dying, or, you know, you're living hand to mouth, you should be involved. And, and not just, you vote every two years, but like, really, really involved.

• 48:32Kara Swisher?

  You are very obviously steeped in teachings of these ancient philosophers. You own a bookstore near Austin and advocate not just reading books like The Odyssey, but reading them multiple times. I completely agree with you on that. There's a big conversation happening right now about whether we're witnessing the end of reading. One study found that fewer than half adults reported on reading a book in 2022. Talk about the tension here of interesting people to these works without reducing them to digestible content, because you want them to actually read it.

• 49:00Speaker 00

  Yeah, I think people are consuming too much news and not reading enough books. And the ancient texts are about all of the dilemmas that we are talking about today. I mean, that's what's so fascinating about this movie edition of The Odyssey is like, The Odyssey is about a collapse in the order of things, and the contradictory and conflicting desires of the human heart against itself. And so.

• 49:25Kara Swisher?

  And people like it. They seem to be attracted to it.

• 49:29Speaker 00

  Yes. But I just think people are reading too much contemporary news, and they're not rooted enough in history and psychology and humanity. It's like, I would love for you just to be reading more literature and poetry, and, and these are all going to help maintain that, again, ethical moral core, that fundamental humanity that all these people are talking about preserving Western civilization. That's what Western civilization is, what we owe the stranger, you know, what's beautiful and good, what are our, our values? That's Western civilization, not blond hair and blue eyes, or whatever. Like, skin color is not Western civilization.

• 50:09Speaker 00

  It's the texts, which by the way, would have been lost if it weren't for the, the writers and thinkers in the East. So this, this silliness of racial distinctions is absurd.

• 50:21Kara Swisher?

  Well, that's a whole nother show. But a lot of people are understandably skeptical of the world of self-help and the people evangelizing self-improvement. It's all, it's been around forever. But if there's one thing that even someone who's not on board ought to try, what would it be, from your perspective?

• 50:36Speaker 00

  If I could give like, a basic thing, you know, a sort of a make your bed kind of a piece of advice that people should do, just to, to push back on that idea from Marc Andreessen about not being introspective, like, actually, the smartest, most successful, big prime movers of history, most of them kept journals or wrote memoirs because they were putting themselves up for review. They were thinking about what they were doing. And one of the incredible things about Marcus Lewis's meditations is we have the private thoughts of the most powerful man in the world, who is trying to get better. And I do think spending some time off of a screen with a pen and a piece of paper,

• 51:18Speaker 00

  and writing and analyzing your own thoughts, is an extremely powerful, transgressive, life-changing thing that we would be better if more people did.

• 51:29Kara Swisher?

  Yeah, I think, I agree with you. I think the reason Marc Andreessen doesn't do it is because in the quiet moments, he knows exactly the damaged, troubled person he is.

• 51:40Speaker 00

  He would have to make some changes.

• 51:41Kara Swisher?

  So that is an excellent piece of advice. Write things down and read the text. Please read the text.

• 51:46Speaker 00

  Yes.

• 51:47Kara Swisher?

  Anyway, Ryan, you're a wonderful person. I really enjoy a lot of your stuff. I'm a big fan.

• 51:50Speaker 00

  Thank you.

• 51:51Kara Swisher?

  And I really appreciate it.

• 51:52Speaker 00

  Oh, well, that's so nice. Thank you very much.

• 51:57Kara Swisher?

  Today's show was produced by Nishat Purwa, Michelle Aloy, Catherine Millsap, Madeline LaPlante Doobie, Megan Burney, and Kalen Lynch. Special thanks to Rosemarie Ho, Dave Shaw, Jim Mackel, and Manolo Moreno. Our engineers are Fernando Aruda and Lich Kwan, and our theme music is by Trackademics. If you're already following the show, you think about the Roman Empire a reasonable number of times each week. If not, you've practiced zero introspection. Go wherever you listen to podcasts, search for On with Kara Swisher, and hit follow. Thanks for listening to On with Kara Swisher from Podium Media, New York Magazine, the Vox Media Podcast Network, and us. We'll be back on Thursday with more.

• 52:42Speaker 02

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