Young men love stoicism. So do tech oligarchs. Why is it resonating?

1. 0:00 – 1:20

   Intro

   1. RHRyan Holiday0:00

      I, 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-

   2. KSKara Swisher0:17

      Right

   3. RHRyan Holiday0:17

      ... was acting on, on the Greeks in the Socratic period. It is on.

   4. KSKara Swisher0:26

      Hi, everyone. Today we're talking about the Internet's favorite brand of philosophy, Stoicism. Stoicism arose in a time of chaos, which might explain why it's resonating with so many people today. My guest this episode is Ryan Holiday, who's made a name for himself in the space. He's written about a dozen books on Stoicism. He's also the host of a popular podcast, The Daily Stoic, and he's not afraid to call out tech leaders, MAGA politicians, and manosphere influencers for getting Stoicism wrong. I really think it's an important thing to talk about. I love talking about philosophy. I am the mother of young men, and a lot of young men are attracted to this. It's a really interesting philosophy, and it's one that's important to get right, and to think about how you wanna live your life is going to be topic A going forward in this time of real chaos. This was a thoughtful conversation, so let's get into it.

2. 1:20 – 3:35

   What people get wrong about Stoicism

   1. KSKara Swisher1:20

      Ryan, thanks for coming on, on.

   2. RHRyan Holiday1:22

      Yeah, thanks for having me.

   3. KSKara Swisher1:24

      So, uh, there's a lot I wanna talk about, about modern Stoicism, its appeal to young men, how leaders in tech and politics are getting it wrong. Um, my first clue, I have two... 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. Um, but to start, wh- why do pe- what do people get wrong about Stoicism?

   4. RHRyan Holiday1:46

      Well, I think that the word Stoic is, uh, unfortunate in the English language, uh, just as the word Epicurean is, right? We te-

   5. KSKara Swisher1:54

      Mm-hmm

   6. RHRyan Holiday1:55

      ... we think an Epicurean is a, is a pleasure-loving hedonist.

   7. KSKara Swisher1:58

      Mm-hmm.

   8. RHRyan Holiday1:58

      And then we think a Stoic is an emotionless robot.

   9. KSKara Swisher2:01

      Right.

   10. RHRyan Holiday2:02

       And that's-

   11. KSKara Swisher2:02

       Grin, grin and bear it, essentially.

   12. RHRyan Holiday2:03

       Yeah.

   13. KSKara Swisher2:04

       Right?

   14. RHRyan Holiday2:04

       Yeah, which is not what either of the philosophies are about. Um, so, so I think the stereotype as the, the emotionlessness, uh, is, 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, and, 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.

   15. KSKara Swisher2:48

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

   16. RHRyan Holiday2:55

       Yeah. Yeah, exactly. I, I mean, look, Marcus Aurelius is the most powerful man in the world. Uh, there's, he's the Emperor of Rome. I think there's a reason that that is attractive to young men in particular. Um, it's different than the sort of academic philosopher. It's different than the, um, the nerdy philosopher. It's different than the egghead, you know, all these things. So I think there's an attraction there, the, the irony being that Marcus Aurelius, although he is, uh, 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.

   17. KSKara Swisher3:32

       Absolutely. So let, let's then define

3. 3:35 – 9:00

   Why Stoicism Is Seeing A Surge in Popularity

   1. KSKara Swisher3:35

      what Stoicism is and why it's m- i- it's seeing the resurgence in popularity. And again, you're not talking about modern dictionary definition of the word Stoicism, which is to endure pain and difficulty without showing any emotion. What you're talking about is a philosophy that goes back millennia. Um-

   2. RHRyan Holiday3:49

      Yes

   3. KSKara Swisher3:49

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

   4. RHRyan Holiday4:00

      Yeah, it's interesting to think, like, Stoicism is an ancient philosophy to the Romans, right? It starts in, in Greece, you know, sometime around the fourth century BC. Uh, it, it's, it's rooted in, in Cynic philosophy, uh, 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 Stoa Poikile. That's the painted porch in, in the Agora in Athens. And so it's this philosophy that, that ultimately comes to be rooted around these four virtues of courage, temperance or moderation, uh, justice, and wisdom. And it makes its way ultimately from Greece into Rome. But as a philosophy, I, 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, uh, 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. Um, you know, it, it, so much was outside of their control, you know. Most children died in infancy. You could be thrown in jail by a tyrant. Uh, 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.

   5. KSKara Swisher5:25

      Yeah.

   6. RHRyan Holiday5:25

      A, 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, 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.

   7. KSKara Swisher5:47

      From our daily lives.

   8. RHRyan Holiday5:48

      Totally.

   9. KSKara Swisher5:48

      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. Um, can you, um, can you apply those today, you know, even with yourself, um, of, of how, h- as a way of explaining what they are and how they intersect? 'Cause intersection is critical-

   10. RHRyan Holiday6:08

       Sure

   11. KSKara Swisher6:08

       ... for all four of them.

   12. RHRyan Holiday6:09

       Yeah, the, it... 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. Um, 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. Um, and so, so the- they all inform each other. Uh, uh, discipline would be, um, the right, uh, 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. Um, you know, YOLOing everything-

   13. KSKara Swisher6:59

       Mm-hmm. Yeah

   14. RHRyan Holiday6:59

       ... um, i- isn't courage. It's just wildly irresponsible.

   15. KSKara Swisher7:03

       Right. Right.

   16. RHRyan Holiday7:03

       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, it's your understanding of things, the value of things, the truth of things. So all the virtues inf- inform each other and are, are difficult to separate. Um, but, uh, you know, you can't really have one without the other.

   17. KSKara Swisher7:28

       Do, do, do you have some point to something in your own life recently where those things were bal- trying, you were trying to balance them out?

   18. RHRyan Holiday7:34

       Ooh. Um, uh, I mean, I'll give you a good, uh, one I struggle with with d- with discipline. Um, I, uh, and this sounds like a, you know, my, my, my problem is I, I just care too much.

   19. KSKara Swisher7:46

       [laughs]

   20. RHRyan Holiday7:46

       My, my problem for, for, like, like, I love, I love exercise. I love, uh, 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, d- the discipline there, it- it's not always pushing to do more. Uh, 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? How am I, how am I expressing myself both firmly and reasonably? Um, so, so I, I, 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.

   21. KSKara Swisher8:51

       That's a good one. I'm very disciplined. I didn't run this morning. I'm like, "I'm tired."

   22. RHRyan Holiday8:54

       [laughs] Good for you.

   23. KSKara Swisher8:54

       I'm tired as fuck, and I'm staying in bed. Um, I'm very disciplined about that. Um,

4. 9:00 – 17:00

   Why Stoicism Thrives in Times of Chaos

   1. KSKara Swisher9:00

      uh, again, we're talking about a philosophy that dates back to before the birth of Christ, and yet your, y- your, your YouTube videos and, uh, 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-

   2. RHRyan Holiday9:15

      Yeah

   3. KSKara Swisher9:15

      ... or particularly unjust. Uh, do you think that's what's happening now, or d- or, or not? Or is, is it, is it linked to that in your, in your mind?

   4. RHRyan Holiday9:24

      Yeah, I mean, look, uh, one of the, one of the great Stoics is Epictetus, who is... Actually, the, the two, 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, and there's not that much we can do about it." Um, so, so I think-

   5. KSKara Swisher9:46

      Mm-hmm. Epictetus w- was a slave too.

   6. RHRyan Holiday9:47

      Epic-

   7. KSKara Swisher9:48

      But go ahead.

   8. RHRyan Holiday9:48

      Yeah, Epictetus is enslaved. He, he spends the first 30 years of his life as a slave. The, it, it's really interesting just how much of the social spectrum the, the Stoics end up taking up. You know, we have, uh, Epictetus on one end of the social spectrum, and then his, uh, 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, uh, everything is going well, you know, it's a little easier to be an Epicurean.

   9. KSKara Swisher10:19

      Mm-hmm. Mm-hmm.

   10. RHRyan Holiday10:19

       [laughs] It's, um, 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, I think there's, there's, um, there's a, a reason that, that, that the Stoics are resonating today. But it's worth going back and thinking, you know, uh, 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 n- 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, it's, it's in the, you know, the times that try men's souls that, that I think we turn to 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.

   11. KSKara Swisher11:32

       Absolutely. Cato was hugely popular with the Founders, and church attendance seems to have at least flatlined after decades of decline. I think it's because people are searching for community right now. There's been much written about the ways young men in particular are struggling in modern society. Scott Galloway, who I do a podcast with, obviously 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.

   12. RHRyan Holiday11:56

       Yeah.

   13. KSKara Swisher11:56

       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. Um, do you see this as part of that trend? Uh, to me, it's community is what he's searching for, or, or non-online life, I guess, something like that, or real life.

   14. RHRyan Holiday12:13

       I think, I think community's part of it, but I, I also do think spiritual guidance and moral direction is something we are thirsting for. You, you take, uh, church out of public life, you take moral instruction out of school because we don't wanna be judgmental, we don't wanna yuck anyone's yum. We wanna 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, and, and all of that is well and good, but what it does create is a bit of a vacuum. Like, who, who should I look up to? What is, what is good? Uh, what is, what is evil? Um, how should I live my life? I, I think particularly for young men, there is a hunger for direction. I think, um, you know, 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 resna- resonant there. They, they, they share the same cardinal virtues. There, there is... I just, I just think people are... They know what they... 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-

   15. KSKara Swisher13:32

       Mm-hmm

   16. RHRyan Holiday13:32

       ... some of those questions.

   17. KSKara Swisher13:33

       There's also some attraction to this pope, I think, and the previous one. I think that's one thing.

   18. RHRyan Holiday13:37

       Mm-hmm.

   19. KSKara Swisher13:38

       Which is, it's just interesting 'cause I never took them, took him to church, never did. I happen to be Catholic. I never, haven't been to church in 100 years. But it was a really interesting thing. I was really... I, and again, I'm dri- I'm very supportive. I'm like, "Great. This is what makes you feel better. It makes you feel like you can cope. It gives you direction. Um, it makes him more, uh, rounded. Great. This is really good for you." It, it seems very good, at least at this point.

   20. RHRyan Holiday14:00

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

   21. KSKara Swisher14:03

       Of course I did. I did a whole show on it.

   22. RHRyan Holiday14:05

       [laughs]

   23. KSKara Swisher14:05

       I did, yeah. Yeah, what did you think of that? Mag-

   24. RHRyan Holiday14:07

       Well, I just-

   25. KSKara Swisher14:08

       ... magnificent humanity.

   26. RHRyan Holiday14:09

       I, I thought it was so fascinating because, you know, for the last, for, 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 wanna 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, what, like-

   27. KSKara Swisher14:44

       Yeah

   28. RHRyan Holiday14:44

       ... we just live in this, u- 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? Should I be doing this or not?" Um, it's just like, "Hey, can this get funding or not?"

   29. KSKara Swisher15:01

       Right.

   30. RHRyan Holiday15:01

       "Will this go viral or not?"
5. 17:00 – 22:50

   A Philosophy of Self-Regulation in a Time of Excess

   1. KSKara Swisher17:00

      from an outside expert. Here's yours.

   2. SPSpeaker17:03

      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?

   3. RHRyan Holiday17:19

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

   4. KSKara Swisher17:21

      Thank you.

   5. RHRyan Holiday17:21

      I love that. Um, what a kid.

   6. KSKara Swisher17:23

      Yeah, I raised him right.

   7. RHRyan Holiday17:24

      Yeah.

   8. KSKara Swisher17:24

      Yeah.

   9. RHRyan Holiday17:25

      I mean, the, the Stoics were thinking about this themselves, right? So Marcus Aurelius can do anything he wants, right? Um, and we know, uh, we, we have a, 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, um- That's a pu- uh, 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, uh, throwing people off of cliffs when they fall out of favor with him or, or whatever. That, that this i- 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, that your average person in America 2,000 years later could relate to the, 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.

   10. KSKara Swisher18:41

       Right.

   11. RHRyan Holiday18:41

       So it, it, it then becomes imperative on us to go, "Well, how should I live? What should I do? And what kind of person do I wanna be?" Those are the questions that we have to ask and, and, and the answer becomes, um, you know, what, what kind of life do you wanna live? Do you wanna l- do you want to, because you're free to do anything, actually become a slave to whatever your impulses are? Like, E- Epict- 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-

   12. KSKara Swisher19:15

       Right

   13. RHRyan Holiday19:15

       ... he, he tells it, one of my favorite scenes, he, he sees, um, this guy sucking up to Nero's, uh, cobbler to win favor with the emperor, and he has to blow smoke up the ass of a guy who makes shoes because he doesn't want, uh, you know, to lose favor with this deranged emperor. And-

   14. KSKara Swisher19:31

       Yeah, that sounds familiar. That sounds familiar.

   15. RHRyan Holiday19:33

       It does. It does, right?

   16. KSKara Swisher19:34

       Yeah, yeah.

   17. RHRyan Holiday19:34

       It's like, uh, do I wanna go to the Melania premiere? Uh-

   18. KSKara Swisher19:38

       Yeah, yeah

   19. RHRyan Holiday19:38

       ... and, and you go, okay, if a billionaire can't say no-

   20. KSKara Swisher19:42

       Right

   21. RHRyan Holiday19:42

       ... to doing something that they obviously don't wanna do, is it actually that great to be a billionaire? I'm-

   22. KSKara Swisher19:49

       Correct

   23. RHRyan Holiday19:49

       ... I'm sure it's great.

   24. KSKara Swisher19:50

       I always say that.

   25. RHRyan Holiday19:50

       Is it, is it that, is the billionaire as powerful as you think they are?

   26. KSKara Swisher19:54

       Right. It's, it-

   27. RHRyan Holiday19:54

       And the answer is no, because there's things that they can't not do.

   28. KSKara Swisher19:58

       Yeah.

   29. RHRyan Holiday19:58

       And-

   30. KSKara Swisher19:58

       We'll, we'll get to these billionaires in a second. It's, it's sort of like the, that h- how why would you have fuck you money if you can't say fuck you, essentially.
6. 22:50 – 24:00

   The parallels between Roman Empire and the U.S.

   1. KSKara Swisher22:50

      easily between now and then, obviously.

   2. RHRyan Holiday22:52

      I mean, uh, uh, look, our, our system is based on Rome. They're called senators 'cause that's what they were called in Rome. It's called the Capitol because in Rome there was Capitoline Hill. Like this is, this is, we are living, we are living in a system designed by people who were cosplaying as the Greeks and Romans. Like, um-

   3. KSKara Swisher23:10

      Mm-hmm. Absolutely

   4. RHRyan Holiday23:11

      ... a- and so I, I do think, uh, I, I do think about Rome all the time. Like Rome is my Roman Empire, um, a- and I, I love it and I find it, and find it endlessly fascinating.

   5. KSKara Swisher23:21

      It is.

   6. RHRyan Holiday23:22

      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-

   7. KSKara Swisher23:37

      Correct

   8. RHRyan Holiday23:37

      ... was acting on, on the Greeks, you know, in the, in the Socratic period.

   9. KSKara Swisher23:41

      Mm-hmm.

   10. RHRyan Holiday23:42

       So-

   11. KSKara Swisher23:42

       And the British. The British

   12. RHRyan Holiday23:43

       ... yeah. Uh, th- sure. I mean, uh, this, the reason you study history is to understand the present, and I think th- they have a lot to teach us, um, both, both good and bad.

   13. KSKara Swisher23:57

       Support for this show comes from Built. Your brain loves

7. 24:00 – 31:00

   Why young men are drawn to Stoicism

   1. KSKara Swisher24:00

      rewards. In fact, there's a whole system in there nicknamed the reward system. So why not take a page out of your brain's book and create a reward system for when you make your housing payments? That's exactly what Built did. You can redeem Built points for flights, hotels, Lyft rides, amazon.com purchases, future housing payments, and more. Built also gives every member access to its agentic neighborhood concierge in the Built app. It's basically an assistant that's connected to both your home and over 50,000 merchant partners. You can also ask it to pay your rent, make a dinner reservation, book a fitness class, schedule a Lyft, and more. It can help you out while automatically applying your member benefits along the way. It's not just for renters. Built works for mortgages too. When your housing payment is one of your biggest monthly expenses, you might as well earn points on it. Download the Built app and join membership for where you live at joinbuilt.com/kara. That's J-O-I-N-B-I-L-T.com/kara, K-A-R-A. Use our link so they know we sent you. So as, 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, uh, Galloway writes and talks a lot about this. Uh, 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.

   2. RHRyan Holiday25:33

      Yeah.

   3. KSKara Swisher25:33

      Um, what do- be, be very clear with people. Um, what it says about what it actually means to be a man for people who sort of take it f- and use it for whatever, uh, purposes.

   4. RHRyan Holiday25:47

      Well, one of the, one of the most interesting pieces of, of writing, or I guess it was speaking, uh, that, that survives to us a-a-as a, as a little essay is from Musonius Rufus, who's the teacher of Epictetus, and he, he, he asks, "Should women be taught philosophy?" And ultimately, where he comes down i- 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 the... Al- although Stoicism, because the ancient world was i-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 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, who assassinates Julius Caesar with her husband, Brutus, uh, though she gets sort of short shrift in, in both Shakespeare and, and the Plutarchan histories of it. Um, I guess what I'm, what, 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 our obligations as a human being is as a member of society, um, o-of which I think, uh, o-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. 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, uh, of course they are. So, um-

   5. KSKara Swisher27:30

      Yeah

   6. RHRyan Holiday27:30

      ... I, I don't want it to be a particularly gendered philosophy.

   7. KSKara Swisher27:33

      Gendered philosophies. You know, you found Stoicism as a young man at a crossroads-

   8. RHRyan Holiday27:37

      Yes

   9. KSKara Swisher27:37

      ... in life. You were in early 20s. You were director of marketing for American Apparel. It faced many PR crisises under its problematic founder, Dov Charney.

   10. RHRyan Holiday27:45

       Yes.

   11. KSKara Swisher27:45

       And in your f- [laughs] 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-

   12. RHRyan Holiday27:53

       Sure

   13. KSKara Swisher27:53

       ... publicity strategies to generate buzz. W- w- is, is that what brought you to it? Like, "What the fuck am I doing?"

   14. RHRyan Holiday28:00

       It's, it's one of those things where it, it, it takes a while to, 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, it, it, 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, I was thinking, like, "Hey, how does this make me better professionally?" Um, I think it, it took a good chunk of my 20s for the ethical framework of the philosophy to, to, to trickle all, all the way down, and for me to see that actually these things are, are, are related to each other, uh, that, that they're, 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, um, you know, like the, the early stuff that even someone like Jordan Peterson was talking about-

   15. KSKara Swisher29:12

       Mm-hmm

   16. RHRyan Holiday29:12

       ... it's great. You know, make your bed.

   17. KSKara Swisher29:14

       Yeah, early.

   18. RHRyan Holiday29:14

       Read the great books.

   19. KSKara Swisher29:16

       Early stuff.

   20. RHRyan Holiday29:16

       You know, um, 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.

   21. KSKara Swisher29:27

       Yes. Yeah.

   22. RHRyan Holiday29:27

       And-

   23. KSKara Swisher29:27

       I call it the grievance industrial complex. I'm like, "Oh my God."

   24. RHRyan Holiday29:29

       To- totally.

   25. KSKara Swisher29:30

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

   26. RHRyan Holiday29:37

       Yeah. I, I mean, watching somebody destroy a billion-dollar company because they were a slave to their appetites and their ego was, was quite eye-opening, you know? I, I... Dov 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, w- uh, 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 about, is built on exploitation.

   27. KSKara Swisher30:13

       Mm-hmm.

   28. RHRyan Holiday30:14

       And people make millions-

   29. KSKara Swisher30:14

       And extraction

   30. RHRyan Holiday30:15

       ... of dollars for it. But, but it's, it comes at the expense of the workers, it comes the expense at the environment, comes at the expense of all these things. So, so I very much believed in that company, and I was very, uh, 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. They said, "Look, you basically took this thing as far as you can take it, and, um, 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."
8. 31:00 – 35:40

   Social Media’s Anti-Stoic incentives

   1. RHRyan Holiday31:00

      that character exists in all sorts of works of history and literature. And so to watch that, I think it was eye-opening, and 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, um, just realizing that, that, that sort of, um, that sort of chaos and dysfunction and it, 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, I saw a microcosm of this. I-

   2. KSKara Swisher31:41

      When you were... Yeah, yeah. No.

   3. RHRyan Holiday31:42

      Yeah.

   4. KSKara Swisher31:42

      Absolutely. Now, in your, y- in your interview for, with comedian, uh, Hasan Minhaj, you talked about the thing that Marcus Aurelius wrote was the most, w- uh, about most was the common good and how Stoicism is inherently a philosophy about our obligations and responsibility to other people.

   5. RHRyan Holiday31:57

      Yes.

   6. KSKara Swisher31:58

      Um, but as we were talking about earlier in, uh, our tech and social media puts a premium on the opposite, on the individual-

   7. RHRyan Holiday32:04

      Yeah

   8. KSKara Swisher32:04

      ... on self-projection, on performative behavior, and it's turned us all into marketers of ourselves, our personal brands. Talk about how you counsel young people about the way social media takes us away from that resp- it's the opposite direction of Stoicism, for certain.

   9. RHRyan Holiday32:19

      Yeah, it's like, it's like, um, it's like a recipe for being a, a, a hyper sociopath. Like, it, 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, I do think this is why mentally ill people do so well on social media. [laughs] Like, it, it, it, they, they lack some of the restraints and the shame that is a, kind of a final check on some of our, our worst behaviors. They, they, they can fully turn themselves over to the algorithm in a way that I, I don't, I don't think, um, the rest of us can. Um, what I, what I love about Stoic philosophy is that ethical core that we're talking about, that it, it says... You know, there, there's a great, there's a great passage in Meditations that I've been thinking about lately. Marcus Aurelius is talking about, like, how everything is going wrong, and it's, it's sideways. And he, and he says, you know, "I was once fortunate," and, and he says, "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 your own, 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, and, and so you, you think about w- if that's your frame, like, uh, what a refreshing frame of reference that is, uh, for someone who has power and responsibility over a lot of people.

   10. KSKara Swisher33:51

       Right, right, right.

   11. RHRyan Holiday33:51

       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, of big companies. This, this transition towards, like, "Hey, my fundamental obligation is to shareholder value-

   12. KSKara Swisher34:06

       Shareholders, yeah

   13. RHRyan Holiday34:07

       ... 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.

   14. KSKara Swisher34:16

       Now, what's interesting, though, at the same time, I think about this a lot, it, to, 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, um, in no small part to social media. And you have millions of followers. Um, h- how, talk about how you reconcile that 'cause I don't think all of it is bad, for sure.

   15. RHRyan Holiday34:37

       No, and-

   16. KSKara Swisher34:38

       But it does, it does incentivize, as you said, narcissism and-

   17. RHRyan Holiday34:41

       And, and, and look, like, uh, publishers are multi-billion dollar companies. 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, to, to sort of operate in this world or in this system with totally sort of clean hand. Like, you're always gonna 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, uh, his many slaves." Like, th- 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. Like, I, I do think, like, the, the sort of world of commerce is not inherently at, in conflict with, you know-

9. 35:40 – 37:50

   What Tech and MAGA get wrong about Stoicism

   1. RHRyan Holiday35:41

      ... art or the exchange of ideas. So I, I don't have a problem, uh, with, with making money or working on these platforms. I think about, um, 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 f- I don't think about so much of, like, what platforms am I on. I think about what ideas or people am I having-

   2. KSKara Swisher36:12

      That you're putting forth

   3. RHRyan Holiday36:13

      ... on my platform. Like I've had to t-

   4. KSKara Swisher36:14

      Yeah

   5. RHRyan Holiday36:14

      ... I, 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-

   6. KSKara Swisher36:34

      Yeah

   7. RHRyan Holiday36:34

      ... you can't silence him or shut him down, but you can decide not to contribute to the propagation of fundamentally horrible ideas.

   8. KSKara Swisher36:44

      So like we've been talking about, a lot of major figures in tech, MAGA, and politics, and the manosphere claim the mantle of Stoicism, but you 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. Um, so you said there are worse things these tech people can study than Stoicism.

   9. RHRyan Holiday37:05

      Yeah.

   10. KSKara Swisher37:05

       But when tech 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, they feel betrayed by some. Uh, they definitely are betrayed by me, and I have betrayed them. But y- you, talk about you. Yuval had went on to Sam Harris, had this moment with them.

   11. RHRyan Holiday37:24

       Yeah, I, I have been slowly, um, removed from all the group texts that I was o- once on, and, and some of the, uh, the conference invites-

   12. KSKara Swisher37:33

       It's a favor to you

   13. RHRyan Holiday37:33

       ... have certainly evaporated.

   14. KSKara Swisher37:35

       Yeah, yeah.

   15. RHRyan Holiday37:36

       Um, it's, it's been weird. I don't feel like I've changed that much.

   16. KSKara Swisher37:40

       You haven't.

   17. RHRyan Holiday37:40

       And-

   18. KSKara Swisher37:41

       You have not

   19. RHRyan Holiday37:41

       ... and it's, 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

10. 37:50 – 44:40

    What Would Marcus Aurelius and Seneca Think About Silicon Valley Today

    1. RHRyan Holiday37:50

       manuals to, like, getting all his news from, from social media, you, 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.

    2. KSKara Swisher38:03

       Mm-hmm.

    3. RHRyan Holiday38:03

       And watching some of these people-

    4. KSKara Swisher38:05

       That's your next book, Brain Fuck.

    5. RHRyan Holiday38:07

       Yeah.

    6. KSKara Swisher38:07

       Go ahead.

    7. RHRyan Holiday38:08

       Wa- watching, watching some of these people who are incredibly smart, who I've had all sorts of interesting intellectual conversations, just, like, say the most deranged things. Um, and, and, and to say them not like, like, uh, to say them sincerely is, is almost the most alarming part.

    8. KSKara Swisher38:28

       With certainty. Certainty is the thing. The, the, the-

    9. RHRyan Holiday38:31

       Yeah

    10. KSKara Swisher38:31

        ... you know. I always say they're frequently wrong but never in doubt. They're like, like that's not what it s- Of- one time Mark, uh, Mark Zuckerberg was talking about First Amendment, and I was like, "That's not what it said." [chuckles] Like, like, "Did you read it? It's short. It's first. It's not long. It's really easy" kind of stuff. And so it's often that case. So if Marcus Aurelius or Seneca walked through Silicon Valley today, what would they make of the kind of Stoicism practiced by some of these elite figures? 'Cause they do think of themselves that way. They actually-

    11. RHRyan Holiday38:59

        Yeah

    12. KSKara Swisher38:59

        ... do.

    13. RHRyan Holiday39:00

        Yeah. Uh, yeah. [chuckles] It's, uh, so someone tweeted a couple of years ago, it was like, "Every athlete wants to be a VC, and every VC-

    14. KSKara Swisher39:09

        Mm-hmm

    15. RHRyan Holiday39:09

        ... wants to be a Stoic philosopher."

    16. KSKara Swisher39:11

        Mm-hmm.

    17. RHRyan Holiday39:11

        And, um, again, there's worse aspirations than being a, a philosopher. Um, but, um, 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-

    18. KSKara Swisher39:29

        I did

    19. RHRyan Holiday39:29

        ... where they would talk about things. 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 wanna be on this platform or that platform, whether you wanna do a deal with this company or that company. What adverti- 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 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 world, uh, do I want my grandchildren to live in?"

    20. KSKara Swisher40:41

        What would you, when you think about why they've become this way, and I, I'm just using tech leaders 'cause they're the current power, right? They're the current power. Why do you think that is? Why do you... And what would change if they actually did follow these principles? Um, I'm thinking of someone like Peter Thiel or Marc 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. Um, uh, what, what, 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.

    21. RHRyan Holiday41:20

        Yeah. It's pr- it's probably worth stipulating there's not a single American in- industry that has distinguished itself particularly well in the, s- particularly the, the second Trump era as far as living up to these philosophical principles. Um, but um- I, I, I, I trace it back a little bit to when the media turned hostile on tech. They all took that as, uh, they took it very personally.

    22. KSKara Swisher41:51

        They did.

    23. RHRyan Holiday41:51

        Um, 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, I, I don't think they're all living in reality. Like, sometimes when I see some of these extremely bad takes, um, 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, um, no one would go like, "That was-

    24. KSKara Swisher42:25

        Yes

    25. RHRyan Holiday42:25

        ... spectacularly dumb," or, "That is-

    26. KSKara Swisher42:27

        Mm-hmm.

    27. RHRyan Holiday42:27

        That's not just politically-

    28. KSKara Swisher42:28

        That's exactly

    29. RHRyan Holiday42:28

        ... incorrect. It's like, it's, it's, um, it's mean, and it's offensive, and it's stupid. Um, so I, I think, I, I sort of-

    30. KSKara Swisher42:37

        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-
11. 44:40 – 48:30

    Stoicism Is A Call To Get Involved In Politics, Not Sit Out

    1. RHRyan Holiday44:40

       there are some, there are some things that no one is excused from-

    2. KSKara Swisher44:45

       Commenting on

    3. RHRyan Holiday44:45

       ... commenting on.

    4. KSKara Swisher44:46

       Yeah.

    5. RHRyan Holiday44:47

       Completely.

    6. KSKara Swisher44:47

       Yeah. Yeah.

    7. RHRyan Holiday44:47

       And, and commenting is only the start, right? Like, you also have to, you have to be-

    8. KSKara Swisher44:51

       Do something

    9. RHRyan Holiday44:51

       ... involved locally and, and as a, as a, as an, as a citizen-

    10. KSKara Swisher44:54

        As a citizen

    11. RHRyan Holiday44:55

        ... too. But-

    12. KSKara Swisher44:55

        So-

    13. RHRyan Holiday44:56

        Um, yeah

    14. KSKara Swisher44:56

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

    15. RHRyan Holiday45:01

        I mean, I, I, it's, it has certainly cost me people who would have, who disagree with me on those things, right? But, like, one of the, one of the realities of having a, 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, uh, you look, you could have 10 million, uh, YouTube subscribers or newsletter subscribers or whatever, and then i-i- is that something that frees you to say what you think is important? Or is that-

    16. KSKara Swisher45:36

        Right

    17. RHRyan Holiday45:36

        ... something that constrains you-

    18. KSKara Swisher45:38

        Mm-hmm

    19. RHRyan Holiday45:38

        ... from saying what those people might not wanna hear? And then-

    20. KSKara Swisher45:41

        Right

    21. RHRyan Holiday45:41

        ... you go, "Okay. Well, actually, is this person, is that a form of power, or is it a form of slavery and-"

    22. KSKara Swisher45:47

        Prison. Right. Yeah. I agree. You talk a lot about how Stoicism is ultimately a call to get involved, not just accept things as they are. Uh, give us an idea of what does Stoicism look like in practice from your point of view.

    23. RHRyan Holiday45:58

        Sure. There's, so there's this idea that Stoicism is, is, is about not being affected, right? Like, not being affected by what's, what's happening. And, and I, I think we can, we can stipulate to that if by not affected, we mean, uh, 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, i- if, if you're able to maintain your moral compass, your decency, your, uh, your goodness in a, in a fundamentally indecent, screwed-up, broken world, then that's great. Um, I think it was Montaigne said, you know, the, the job i- is to remain human in an inhuman time. So I think first and foremost, that, that, that's really important. And, and we're s- uh, I don't know about you, but I s- 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."

    24. KSKara Swisher46:52

        Mm-hmm.

    25. RHRyan Holiday46:52

        I go, "You're letting them win. Like, you are-"

    26. KSKara Swisher46:55

        Yeah, that's right.

    27. RHRyan Holiday46:55

        Like-

    28. KSKara Swisher46:56

        I, same thing

    29. RHRyan Holiday46:56

        ... if, if you're, if, if they came and, and tried to physically prevent-

    30. KSKara Swisher46:59

        Yeah
12. 48:30 – 52:03

    A Stoic Practice We Can All Adopt

    1. RHRyan Holiday48:30

       the contradictory and conflicting desires of the human heart against itself. And so, um-

    2. KSKara Swisher48:37

       And people like it.

    3. RHRyan Holiday48:38

       Yes.

    4. KSKara Swisher48:38

       They seem to be attracted to it. That, yeah.

    5. RHRyan Holiday48:41

       Yes. But I just think people, 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, and these are all gonna help maintain that, a- again, 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, um, what's beautiful and good, what are our, our values? That's Western civilization, not blonde hair and blue eyes or whatever.

    6. KSKara Swisher49:18

       Right, right.

    7. RHRyan Holiday49:19

       Like, skin color is not Western civilization. It's the, it's the texts, which by the way, would've been lost if it weren't for the c- the, the writers and thinkers in the East. So, uh, th- this, this silliness of, of d- racial dist- distinctions is, is, is absurd. Um-

    8. KSKara Swisher49:37

       Well, that's a whole nother show. A lot of people are understandably extremely skeptical of the world of self-help and the people evangelizing self-improvement. But if there's one thing that even someone who's not on board ought to try, what would it be-

    9. RHRyan Holiday49:50

       Hmm

    10. KSKara Swisher49:50

        ... from your perspective?

    11. RHRyan Holiday49:51

        If I could give, like, a basic thing, you know, a, 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, the, actually, the smartest, most successful, big prime movers of history, most of them kept journals or wrote memoirs because they were, they were putting themselves up for review. They were thinking about what they were doing, and one of the incredible things about Marcus Aurelius's Meditations is we have the private thoughts of the most powerful man in the world, who was trying to get better. And I, I do think spending some time off of a screen with a pen and a piece of paper and writing-

    12. KSKara Swisher50:35

        That's a great piece of advice

    13. RHRyan Holiday50:35

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

    14. KSKara Swisher50:46

        Yeah, I th- I agree with you. I think the reason Marc Andreessen doesn't do it is 'cause in the quiet moments, he knows exactly-

    15. RHRyan Holiday50:52

        Mm-hmm

    16. KSKara Swisher50:53

        ... the f- the, the damaged, troubled person he is. [laughs]

    17. RHRyan Holiday50:57

        He would have to make some changes.

    18. KSKara Swisher50:58

        So, uh, that is an excellent piece of advice. Write things down and read the text. Please read the text. I'm always like, "Just read it. It's so easy."

    19. RHRyan Holiday51:05

        Yes.

    20. KSKara Swisher51:05

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

    21. RHRyan Holiday51:09

        Well, thank you.

    22. KSKara Swisher51:09

        I'm a big fan, and I really appreciate it.

    23. RHRyan Holiday51:12

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

    24. KSKara Swisher51:14

        Today's show was produced by Nishat Kurwa, Michelle Aloy, Katherine Millsap, Madeline Laplant-Dubé, Megan Bernie, and Kaylin Lynch. Special thanks to Rose Marie Ho, Dave Shaw, Jim Mackle, and Manolo Moreno. Our engineers are Fernando Arruda and Rick Quan, 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 practice 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. [upbeat music]

Episode duration: 52:03