On with Kara Swisher - Ryan Holiday on the Case for Stoicism in an Age of Distraction

Episode Date: August 17, 2026

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 [e-mail] or find us on YouTube, Instagram, TikTok, Threads, and Bluesky @onwithkaraswisher.  Learn more about your ad choices. Visit podcastchoices.com/adchoices

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 the Greeks in the Socratic period. 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 service. strategist, Ryan Holliday. He's written around a dozen books on the subject and has a website and popular podcast called The Daily Stoic, where he shares meditations, lessons, and interviews inspired by the great Stoic thinkers. And Holliday is willing to call out the ways tech leaders,

mega-politicians, and Manosphere influences 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 of 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 is a thoughtful conversation with a thoughtful person, so don't go anywhere. Support for this show comes from Odu. Running a business shouldn't feel

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Hire the right pro today. Our earliest childhood memories can feel so visceral. I have this memory of my mother standing on the beach, you know, the wind whipping her hair and her jacket, calling into the wind with my siblings out in the lake and the dam, you know, looming in the distance. But none of these memories were true.

This week, Unexplained It to me from Vox. Why can't I remember being a baby? Ryan, thanks for coming on on. Yeah, thanks for having me. 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 had 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? Well, I think 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. Right. Grin and Barrett, essentially, right? Yeah, which is not what either 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 chat GPT 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 reason and virtue and decency and goodness. and some big things that I think are missing in some of the popular conceptions of the philosophy.

So they get that it's sort of a strong man kind of thing, like a strong, silent type kind of thing. Yeah, exactly. I mean, look, Marx-Sirilis 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 nerdy philosophy. philosopher, it's different than the egghead, you know, all these things. So I think there's an attraction there that the irony being that Marcus Reelis, although he is, the Emperor of Rome, is known in his time for how thoughtful and considerate and patient and all the opposite of these things we're now projecting onto him. Absolutely. So let's then just find with Stoicism

and why it's seeing 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 Barrett thing I was talking about. What you're talking about as a philosophy goes back millennia. Yes. Give us the, and I hate to say, Cliffs no 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, popular. 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 BC. It's rooted in cynic philosophy, first and foremost. But basically this guy named Zinian,

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 Stoapokile. That's the painted porch 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, 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 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 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 thinking about then, as opposed to, you know, how we think about philosophy now, which is, you know, so removed, from the day-to-dayness.

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

and how they intersect? Because intersection is critical for all four of them. Yeah, Zeno would talk about how the four virtues are distinct and yet inseparable from each other. I'll give you a great example. So courage, 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 fast can you run? Discipline is also rooted in the idea of temperance or moderation.

What is the right amount? So even Aristotle was talking about how, you know, too much courage becomes requisite. and not enough courage is, of course, cowardice. You know, yoloing everything. It isn't courage. It's just wildly irresponsible. 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 difficult to separate. but you can't really have one without the other. Did you have some point to something in your own life recently where you were trying to balance them out? Ooh, I mean, I'll give you a good one I struggle with with discipline. I, and this sounds like, you know, my problem is I just care too much. My problem for like I love exercise, I love working out, I love running. For me, it's harder to go, hey, like my ankle hurts today.

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 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 discipline that I think about the most is just the do I need to get upset about this? Am I keeping my cool here?

How am I expressing myself both firmly and reasonably? So I would say I deal with the virtue of maybe the best way to describe discipline 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 your first reaction to things. So that's probably the day-to-day one that I'm thinking about the most. That's a good one. I'm very disciplined. I didn't run this morning. I'm like, I'm tired. I'm 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 before the birth of Christ,

and yet your YouTube videos and podcasts are hugely popular, millions of views. You've said the interest in socialism 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 is it linked to that in your mind? Yeah, I mean, look, one of the great stoics is Epictetus, who is, actually two of the great stokes. We have Epictetus and Seneca, both live through the reign of Neuro. 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.

Epictetus was a slave, too. 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 Rialius. You know, Marx Trilis lives through a plague. You live 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 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 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 think there's 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 times that try men's souls that I think we turn to our forebears who went through difficulties

and we try to go, well, what do they figure out about getting through this? And I think Stoicism has long been that. Absolutely. There's also a lot of overlap with Stoicism and the three Abrahamic phase, Judaism. Christianity in 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 them 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 non-online life, I guess, something like that, or real life. I think community is part of it,

but I also do think spiritual guidance and moral direction is something we are thinking. thirsting for. Like, 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 go, well, this person was a slave owner and this person was a tyrant and this person was a this and 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? Um, how. How should I live my life? I think particularly for young men, there is a hunger for direction.

I think of all the faiths to have a resurgence, you know, Catholicism is interesting. And I do think, you know, I grew up Catholic. So 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 answer some of those questions. 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 to church.

Never did. I happen to be Catholic. I haven't been in church in 100 years. But, again, I'm very supportive. I'm like, great, this makes you feel better. It makes you feel like you can cope. It gives you direction. It makes them more rounded.

Great. This is really good for you. It seems very good. Did you read the Pope's thing on AI, his essay? Of course I did. I did a whole show on it. Yeah, what did you think of that? Magnificent humanity. I thought it was so fascinating because, you know, for my whole life, 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 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 a moral society where we have stripped out the ability to even ask those questions about like, is this right or wrong? 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 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 these are, in fact, the most essential questions to consider. 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 I wonder if the Pope is a stoic. He feels a little bit.

You know, I was just in Rome and we went and saw a blessing of the Pope and you see him going. going around in the little Pope mobile. And it was funny, you know, 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 Marcus Relius and the Pope have the same title, Pontifix Maximus, that Rome absorbs, Rome as the Catholic Rome, absorbs so much of the iconography and 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 were having those kinds of discussion. I think this is what's really great about The Odyssey. I hate that so much of the dialogue about the Odyssey is about, like, who should have been cast and, you know, this or that. But the Odyssey is supposed to be contentious and create debate, and Odysseus is a hero,

and a villain for the purposes of spurring. It's a complex man. Yes. It says it right there in the first line. That's the whole point, is you're supposed to argue at these different ways and then make different choices in your own life. 100%. We'll get to tech in a second, but every episode we get a question from an outside expert.

Here's yours. Hello, my name is Louis Swisher. I'm Kara's eldest son. And like many young people, I 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? Ooh, that's a great question. Thank you. I love that.

What a kid. I raised him right. Yeah. I mean, the Stoics were thinking about this themselves, right? So Mark Sirelius 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. they were remarkably creative at the excesses they figured out how to go to. So Marcus Aureus could do all that.

But I think what he realizes is that that's actually not freedom but a kind of a punishment, 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 this sort of excess is a kind of a prison. 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 your average person in America, 2,000 years later, could relate to the luxuries and temptations of a Roman emperor. But that is how fortunate we are as a society, right? And that we have 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 the answer becomes, what kind of life do you want to live? 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 tells one of my favorite scenes, 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. Yeah, that sounds familiar. It does, it does, right? It's like, do I want to go to the Melania premiere? Yeah, yeah.

And you go, okay, if a billionaire can't say no, Right. To doing something that they obviously don't want to do. Is it actually that great to be a billionaire? I'm sure it's great. 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. Yeah, we'll get to these billionaires in a second.

It's sort of like the, why would you have fuck you money if you can't say fuck you, essentially, right? Totally. And to me, it's more like I always think I did a podcast on Succession. I called them Kashmir prisons, right? they're in prisons. And then when I look at a lot of the tech people, I'm like, I can leave. You can't your Kashmir 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 Marx really, of course, was a dictator, if you can apply that to our modern era? He had every choice. But I guess we're like that, too. We have every choice, or at least in the United States.

I like to think of Marcus a little bit like 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 beginning of meditations where Marksruis 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 empire. He doesn't choose this. It doesn't, how much can he change the system? I don't know. I'm fascinated by the moral predicaments that these

philosophers get themselves into. Yeah. I own slaves and yet I'm asking for freedom. Yeah. And look, it's easy 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 like that the Stoics were involved to a degree that their philosophical principles are being tested. I don't like that they didn't always pass these tests, right? Like Seneca 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. I have no problem putting them up and analyzing their moral predicaments. I just, I think ultimately, 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.

Yeah. How often do you have to think about the Roman Empire? Because the relationships you can make very easily between now and then. I mean, look, 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 in a system designed by people who are cosplaying as the Greeks and Romans. And so I do think about Rome all the time. Like Rome is my Roman Empire. And 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 the Greeks, you know, in the, in the Socratic period. So. And the British? Yeah. Sure. I mean, the reason you study history is to understand the present. And I think they have a lot to teach us both good and bad.

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would turn to stoicism as a means of finding resilience and strength. It's either that or peptides and tea, I guess. 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. Be very clear with people what it says about what it actually means to be a man for people who sort of take it and use for whatever purposes. Well, one of the most interesting pieces of writing, or I guess it was speaking 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. 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 patriarchical, 95% of the Stoics we know about are men and a lot of the metaphors are wrestling and fighting and, you know, things women weren't allowed to do, that being said, there were plenty of Stoic women. One of the most impressive Stoic women in history is Cato's daughter, Portia, who assassinations Julius Caesar with her husband, Brutus, though she gets sort of short shrift in both Shakespeare and the Plutarchian histories of it. I guess what I would say is that socialism 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 obviously being a man or a woman is a part of. So I do think there's this like,

sort of over-emphasis on what it can teach young men. Like, I know from my talks that, like, a good chunk of the audience 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 I don't want it to be a particularly gendered philosophy. You know, you found Stozoism as a young man acrossroads and lives. You were in early 20s.

You were a director of marketing for American Apparel. It faced many PR crises under its problematic founder, Dub Charney. What a job. And in your first book, trust me, I'm lying, which 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? It's one of those things where it takes a while to sort of get its teeth into you. I think the reason that young men are attracted to stochism 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 all these things that I think young men are particularly after. So if that's the way in, I'm all about it. And that was certainly the way in for me. I was thinking like, hey, how does this make me better professionally? It took a good chunk of my 20s for the ethical framework of the philosophy 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 think as a motivational philosophy, the entry point is often there, which is good. You know, 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 problem is when that gets yoked to sort of grievance politics and stuff. I call it the grievance industrial complex. Totally. So what motivated you, what got you there to actually start living stoises as opposed to chewing on it in your head like that? Yeah. I mean, watching somebody distrary. a billion dollar company because they were a slave to their appetites and their ego was quite

eye-opening, you know, Doug Charnney 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 used to say, like, you can't make a bikini for $6 without fucking somebody over. And he's totally right. You know, like 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 expense at the environment, comes at the expense of all these things. So I very much believed in that company. I was very

inspired by it, and I loved it. And then watching him destroy it to choose, you know, he could have walked away. 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 got to bring in some adults. And he was like, I'd rather burn it to the ground. And so to watch. Yeah, I know that. Yeah. 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 in it. 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 Meglomania was ultimately, like, it always ended in the same place, was for me a really powerful inoculation against Trumpism as a powerful inoculation against some of the Silicon Valley ism, that Elon Muskism. It's like, I've seen, I saw a microcosm of this. When you were, yeah, no, absolutely. Now, in your interview with comedian Hassan Minaj, you talked about the thing that Marcus really just wrote about most was the common good and how stoicism is inherently a philosophy about our obligations and responsibility to other people.

Yes. But as we were talking about earlier, 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, or 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. Yeah, it's like a recipe for being a hyper-sociopath. Like, it's like, hey, let me take your worst impulses and exaggerate them and incentivize them and monetize them. And 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 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 think the rest of us can. What I love about Stoic philosophy is that ethical core that we're talking about. There's a great passage of meditations that I've been thinking about lately. Mark Srealis is talking about how everything is going wrong and it's sideways. And he says, I was once fortunate and then at some point fortune abandoned me. And then he says, 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 good actions, good character, and good intentions. And so 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 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. 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, saw mine 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. No.

But it does incentivize, as you said, narcissism. 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 tradeoffs or dilemma. 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? And 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. And if they don't like it, they can get their money back or not purchase it. I do think the sort of world of commerce is not inherently in conflict with art or the exchange of ideas. So I don't have a problem 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 think more about that.

Like, I don't think about so much of, like, what platforms am I on? I think about what ideas or people am I having on my platform. Like, I've had to, 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.

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Megan Rapino here. This week on Why Are You Like This, I got to sit. with legendary Minnesota links coach Cheryl Reeve in Chicago during All-Star Weekend. We get into her personal style of activism, how she supports her players as people, and why she proudly considers herself a dyke. Then we learn if she's more of a mommy, daddy, or baby. Check out the latest episode of Why Are You Like This, wherever you get your podcast, and on YouTube. So like we've been talking about, a lot of major figures in tech, megapolitics, 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 there are worse things these tech people can study than stoicism. But in tech, the world 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 feel betrayed by some, they definitely betrayed by me, and I have betrayed them. But you, talk about you. You've all went under this. Sam Harris had this moment with them. Yeah, I have been slowly removed from all the group texts that I was once on. And some of the conference invites have certainly evaporated. That's a favor to you. Yeah. It's been weird. I don't feel like I've changed that much. And it's been interesting to watch people

radicalized. 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- That's your next book, brain fuck. Yeah. 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 almost the most alarming part. With certainty is the thing. Yeah. I always say they're frequently wrong, but never in doubt. Like one time Mark Zuckerberg was talking to First Amendment,

and I was like, that's not what it said. Like did you read it? It's short. It's really easy kind of stuff. And so it's often that case. So if markets really is there's done like a walk through Silicon Valley 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. Yeah. It's like 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. I did. 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 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 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 question. about national security, about the future of our democracy, they've all made the decision about what's good for, you know, 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? What would you, when you think about why they've become this way, and I'm just using technology because they're the current power, right?

Sure. Why do you think that is, and what would change if they actually, actually did follow these principles. I'm thinking of someone like Peter Thiel or Mark Endries, and now, Teal is not a stoic. In fact, he's criticized stoicism at times from being too passive. Andreson has occasionally talked about it, and 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. Yeah, it's probably worth stipulating there's not a single American industry that

has distinguished itself particularly well in the, particularly the second Trump era as far as living up to these philosophical principles. But I trace it back a little bit to when the media turned hostile on tech, they took it very personally. They did. 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. 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 I did, then I stopped going because it was like pointless. Totally. 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. I could, except, you know, the stoics are all involved in politics, right? Like, it 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 mass agents and 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 back. Right? Like, I just, I don't know. 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 commenting on, completely. And commenting is only the start, right? Like, you also have to be involved. locally and as a citizen too. But does 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.

It is 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 goes to the stoic idea is like, 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? Right. Yeah, I agree. You talk about hostosism 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. So there's this idea that stoicism is about not being affected, right? Like not being affected by what's happening.

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 job is to remain human in an inhuman time. So I think first and foremost, that that's really important. And we're, I don't know about you, but I talk to people that 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. Yeah, that's nice. Same day. If they came in and tried to physically prevent you from writing, you would see that as textbook oppression. But if you just let the vibes get in your head and prevent you from doing your work, then in a way, it's even worse. And then I think practically, like, how involved are you other than just talking about things on social media, you know? Hashtagism, right?

Yes, yes. Like, have you actually been to a protest? Do you actually vote? So I think it's about being involved. Like, unless something is preventing you from being involved, like your parents are dying or, you know, your living hand to mouth, you should be involved. And not just you vote every two years, but like really, really involved. You were very obviously steeped in teaching of these ancient philosophers. You want 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. But 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 reporter 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. 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, Yeah. 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... And people like it. Yes. 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 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 values. That's Western civilization, not blonde hair and blue eyes or whatever. Like, skin color is not Western civilization. It's the texts, which, by the way, would have been lost if it weren't for the writers and thinkers in the East. So this silliness of racial distinctions is absurd. Well, that's a whole other show. But a lot of people are understanding extremely skeptical of the world of self-help and the people evangelizing self-improvement.

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? 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 push back on that idea from Mark 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 Mark's Reuss's meditations is we have the private thoughts of the most powerful man in the world who was trying to get better. And I do think spending some time off of a screen with a pen and a piece of paper and writing and analyzing your own thoughts is an extremely powerful, transgressive, life-changing thing that we would be better if more people did. Yeah, I agree with you.

I think the reason Mark Andrewsend doesn't do it is because in the quiet moments, he knows exactly the damaged, troubled person he is. You would have to make some changes. So that is an excellent piece of advice. Write things down and read the text. Please read the text. Anyway, Ryan, you're a wonderful person. I really enjoy a lot of your stuff. I'm a big fan.

Thank you. And I really appreciate it. Oh, well, that's so nice. Thank you very much. Today's show was produced by Nishat Perwa, Michelle Alloy, Catherine Millsopp, Madeline LaPlante, Ubi. Megan Bernie and Kaylin Lynch. Special thanks to Rosemary Ho, Dave Shaw, Jim Mackle, and Manolo Moreno. Our engineers are Fernando Aruta and Rick Juan, and our theme music is by Trachidemics. If you're already following the show, you think about the Roman Empire a reasonable number of times each week.

If not, you practiced zero introspection. Go wherever you listen to podcast, search for On with Caroswisher and hit follow. Thanks for listening to On With Caroswisher from Podium Media, New York Magazine, the Vox Media Podcast Network and us. We'll be back on Thursday with more.