The Most Misunderstood Philosopher of All Time | Diogenes Expert Inger Kuin

Diogenes wasn’t a Stoic… but without him, the Stoics don’t exist. His life was so bold, so uncompromising, and so brutally honest that it reshaped the entire philosophical world the Stoics inherited. In today’s episode, Ryan sits down with classicist Inger Kuin to unpack the wild and brilliant philosophy of Diogenes, the original cynic. Inger Kuin https://ingerkuin.com/ is a researcher, writer, and teacher focused on the intellectual history of ancient Greece and Rome. She is Associate Professor of Classics at the University of Virginia https://classics.as.virginia.edu/inger-ni-kuin. Originally from The Netherlands, she publishes both in English and in Dutch. Be sure to pick up a copy of Inger’s new book Diogenes: The Rebellious Life and Revolutionary Philosophy of the Original Cynic https://www.amazon.com/Diogenes-Rebellious-Revolutionary-Philosophy-Original/dp/1541606477. Check out Inger’s website: https://ingerkuin.com/ 📚 If you’re interested in learning more about Diogenes and Cynicism, check out these books: The Cynic Philosophers: From Diogenes to Julian https://www.thepaintedporch.com/products/the-cynic-philosophers-from-diogenes-to-julian-penguin-classics?_pos=1&_sid=333ffa06d&_ss=r How to Say No: An Ancient Guide to the Art of Cynicism https://www.thepaintedporch.com/products/how-to-say-no-an-ancient-guide-to-the-art-of-cynicism?_pos=2&_sid=333ffa06d&_ss=r 🎟️ Come see Ryan Holiday LIVE https://www.dailystoiclive.com/: https://www.dailystoiclive.com/ Seattle, WA - December 3, 2025 https://www.eventbrite.com/e/daily-stoic-live-onstage-with-ryan-holiday-tickets-1830976292379?aff=oddtdtcreatorSan Diego, CA - February 5, 2026 https://www.eventbrite.com/e/daily-stoic-live-onstage-with-ryan-holiday-tickets-1527497619499?aff=oddtdtcreatorPhoenix, AZ - February 27, 2026 https://www.eventbrite.com/e/daily-stoic-live-onstage-with-ryan-holiday-tickets-1830981698549?aff=oddtdtcreator 👉 Support the podcast and go deeper into Stoicism by subscribing to The Daily Stoic Premium https://dailystoic.supercast.com/ - unlock ad-free listening, early access, and bonus content: https://dailystoic.supercast.com/ 🎥 Watch the video episodes on The Daily Stoic YouTube channel https://www.youtube.com/@DailyStoic/videos: https://www.youtube.com/@DailyStoic/videos https://www.youtube.com/@DailyStoic/videos 🎙️ Follow The Daily Stoic Podcast on Instagram https://www.instagram.com/dailystoicpodcast/?hl=en: https://www.instagram.com/dailystoicpodcast https://www.instagram.com/dailystoicpodcast ✉️ Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail https://dailystoic.com/dailyemail 🏛 Get Stoic inspired books, medallions, and prints to remember these lessons at the Daily Stoic Store: https://store.dailystoic.com/ https://store.dailystoic.com/ 📱 Follow us: Instagram https://www.instagram.com/dailystoic/, Twitter https://twitter.com/dailystoic, YouTube https://www.youtube.com/@DailyStoic, TikTok https://www.tiktok.com/@daily_stoic?lang=en, and Facebook https://www.facebook.com/dailystoic See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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

• 0:06Ryan Holiday?

  Welcome to the Daily Stoic Podcast where each weekday we bring you a meditation inspired by the ancient Stoics, a short passage of ancient wisdom designed to help you find strength and insight here in everyday life. And on Wednesdays, we talk to some of our fellow students of ancient philosophy, well-known and obscure, fascinating and powerful. With them, we discuss the strategies and habits that have helped them become who they are, and also to find peace and wisdom in their lives.

• 0:51Ryan Holiday?

  Hey, it's Ryan. Welcome to another episode of the Daily Stoic Podcast. I remember very vividly, I went to a talk that Robert Greene gave at this bookstore in Silverlake, whose name is escaping me. You know what? I want to look this up. Bookstore Los Feliz. Ah, that's what it's called. Skylight Books. Okay. Robert Greene gave a talk at Skylight Books, like, this would have been 20 years ago? I don't know. But I remember, he was talking about this philosopher, Diogenes the Cynic. And not having gotten a philosophy degree, I had never heard of Diogenes the Cynic. And so I went and I read about him. And I've

• 1:34Ryan Holiday?

  been, he's someone I've been reading about, you know, ever since, fascinated by him. And actually, when I was in Australia last summer, to do some talks, by the way, I'm gonna do some more talks. I'm in Seattle next month, and then I'm in Phoenix and San Diego, I believe, in February. You can grab all those tickets at dailystoiclive.com, check the dates. And then I believe, we have another tour in the works for the fall. But that's neither here nor there. When I was in Australia, we went to this bookstore in Australia, and I saw they had this book about Diogenes the Cynic. And I was like, oh, I'd love to read more about him. So I grabbed this book, I'm reading the intro, and, well, I caught a stray bullet

• 2:17Ryan Holiday?

  while I'm reading it. I mentioned it onstage while I was in Australia. Let me play this for you. When I got here, a couple of weeks ago, I got this book on Diogenes the Cynic. I went to Abby's Bookstore there, not far from here, right near Hyde Park. And reading this book, I'm researching it for something I'm writing, and this is what it says. It says, "Considering Stoicism's unexpected resurgence in today's pop culture marketplace, it may be worth pointing out that the teachings of Zeno, Cleanthes, and Chrysippus, the school's original triumvirate, have precious little in common with the vulgar forms of Stoic doctrine now being hawked from all corners of the internet and dispensed at weekend retreats for Wall Street and Silicon Valley warriors who come together

• 2:59Ryan Holiday?

  to enjoy manly companionship fortified by selective readings from Epictetus and Marcus Aurelius. So I came all the way to your lovely country and I caught some stray bullets from this random book I bought."

• 3:12Ryan Holiday?

  So the point is, there was some interesting stuff in the book. I took a bunch of notes. I actually liked it, even though the author clearly doesn't like me, but I was hoping for something a little better. And maybe someone who I think understands how Diogenes can apply to everyday people in everyday life. And as it happens, Diogenes has a lot in common with the Stoics. Actually, let me read you this, because here's someone a little bit smarter than me describing how the Stoics and the Cynics, which is a misunderstood school, are connected. "Just like Diogenes, Stoics are concerned with the dangers of

• 3:55Ryan Holiday?

  desire, but unlike him and Epicurus, they privilege mental over physical well-being. Also, even though they adopted the phrase 'living in accordance with nature' from Diogenes, they mean something else by it. For the Stoics, what suits someone and is therefore in accordance with their individual nature is whatever divine providence has assigned this person. As a result, options that would not seem at all natural to Diogenes and the Epicurians, like choosing to participate in public life, this can be natural to the Stoics if it's something that was fated for you. Nevertheless, the idea that your task is to find out through philosophy and reason what is in accordance with your nature was formulated by Diogenes and taken over by the Stoics."

• 4:38Ryan Holiday?

  Also, the central Stoic notion that it's possible to train yourself through a case to live without luxury goods and to be happy under all sorts of different conditions comes straight from Diogenes' playbook.

• 4:51Ryan Holiday?

  I think that's, that's well said, and we should study and learn from all the different philosophical schools, even when they might be critical of what we think, or us personally, from time to time. Nietzsche, of course, having some good things this day about the Stoics, and negative things. Seneca reminding us that we should read like a spy in the enemy's camp. So with that being said, I wanted to have Inger Kuin on the podcast to talk about her fascinating biography of Diogenes. It's called Diogenes: The Rebellious Life and Revolutionary Philosophy of the Original Cynic. She is a researcher, writer, and teacher focused on the intellectual history of ancient Greece and Rome. She is an associate professor of the

• 5:36Ryan Holiday?

  classics at the University of Virginia. We had a lovely little chat about George Long, one of the original translators of Marx-Realist, who was also there. Gregory Hayes is at the University of Virginia. So it's a great school, source, school and source of Stoic teachings. She's originally from the Netherlands, thus the name and the accent you'll hear in today's episode. And she publishes in both English and in Dutch. You can check out Inger's website, ingerkuin.com. And as I said, check out the new book, Diogenes: The Rebellious Life and Revolutionary Philosophy of the Original Cynic. Inger and I share our favorite Diogenes stories, how he practiced living in accordance with nature, that critical phrase that he coined, and the Stoics picked up on. This is going to be part one of the episode, and I will bring

• 6:21Ryan Holiday?

  you part two later in the week. I think you're really gonna like this episode. Enjoy.

• 6:36Speaker 01

  See, I don't have that.

• 6:38Ryan Holiday?

  You don't even have a galley?

• 6:39Speaker 01

  I don't.

• 6:40Ryan Holiday?

  Oh, wow.

• 6:40Speaker 01

  They didn't send me one. And I realized at some point, oh, maybe I should ask for one. And now I've heard that the real books are coming, like, are gonna be ready so soon that I was like, oh, it's fine.

• 6:50Ryan Holiday?

  Yeah.

• 6:51Speaker 01

  But it's fun to see.

• 6:52Ryan Holiday?

  Well, it's, it's a kind of an interesting experience. Like, I have a book out in October, and I don't have books at all. But yeah, they send you the galleys, and you're like, oh, it's so exciting. And then you're like, after it comes out, you're like, well, what am I supposed to do with these? Like? So you just like pile up all the different.

• 7:07Speaker 01

  Right, yeah, yeah, yeah. No, it's an intermediate.

• 7:09Ryan Holiday?

  And then if you're lucky and you get lots of foreign translations, they send you those. And they're cool for like five seconds. And then I'm like, well, what am I supposed to do with a Mandarin version of the books?

• 7:20Speaker 01

  Yeah.

• 7:20Ryan Holiday?

  Uh, I've not met one person that I could ever even give it to.

• 7:24Speaker 01

  Right. And then they take up space.

• 7:26Ryan Holiday?

  Yeah, I have hundreds of foreign translations that I feel. Do you ever have those things? This would be like, this would be a feeling that Diogenes is not familiar with at all. But do you ever have like something that someone gives you and then you feel you don't want it, but you feel bad throwing it away?

• 7:43Speaker 01

  For sure.

• 7:44Ryan Holiday?

  And so it's like, I can't throw away a French translation of one of my books.

• 7:48Speaker 01

  Yeah.

• 7:49Ryan Holiday?

  But I literally have no reason to have this whatsoever. And I, I sometimes think about that famous story about Diogenes where he's, uh, he, he goes to the well and he's drinking with the cup and he sees the boy drinking from his hands and he shatters the cup. You're like, I don't need this. It's totally superfluous.

• 8:06Speaker 01

  Yeah.

• 8:07Ryan Holiday?

  But I'm not going to throw it away.

• 8:08Speaker 01

  Right. Especially because it was, you know, a gift and somebody gave it to you.

• 8:12Ryan Holiday?

  Well, I mean, I don't even know if they give it to you. They're just contractually obligated to send me my copies. And then I'm like, what am I supposed to do with it?

• 8:18Speaker 01

  Yeah. Yeah. No, I, I was thinking of the other situation where somebody has really picked out a gift for you. And that's, that's even more difficult.

• 8:25Ryan Holiday?

  Yes. Or you ever get something that comes in like a fancy box, like all Apple products?

• 8:30Speaker 01

  Right.

• 8:30Ryan Holiday?

  And then you're like, I should probably keep this iPhone box.

• 8:32Speaker 01

  Right.

• 8:33Ryan Holiday?

  And it's like, only because it, it's like perfectly designed to feel like it's significant, but it's literally garbage.

• 8:41Speaker 01

  Right. No, it's hard. I think I've moved enough times to have gotten a rid of, like, have gotten rid of things like that. And also I've become a little bit better at not keeping them in the first place.

• 8:52Ryan Holiday?

  I'm so mad at it. And then like, I just, I actually just found that they sponsored the podcast, which was nice. But like, what are you supposed to do with all your kids' art?

• 9:02Speaker 01

  Oh, that's really hard.

• 9:03Ryan Holiday?

  Yes.

• 9:04Speaker 01

  That's really hard. And, you know, my, my mother is always in, in the process of like.

• 9:09Ryan Holiday?

  Sending me all my shit back.

• 9:11Speaker 01

  Exactly. Yeah, exactly. This is also something to me and. I mean, most of the time, I'm like, oh, I'm so excited to have this.

• 9:18Ryan Holiday?

  Yeah.

• 9:19Speaker 01

  Which then sort of proves her right for having kept it. But now it's in my, in my place.

• 9:24Ryan Holiday?

  And I go, wait, okay, so you kept this for 30 years? Cause this is my third grade art project or like, you know, a plate that I made. And it's like, I have an eight year old. Do I have to keep this for 30 years before I forced it back onto him?

• 9:39Speaker 01

  Yeah.

• 9:40Ryan Holiday?

  But actually this company that just sponsored the thing and they, that you mail them all the art and they take a picture of it and then they just put it in a book.

• 9:46Speaker 01

  Okay.

• 9:47Ryan Holiday?

  And you have a digital version of it.

• 9:48Speaker 01

  Yeah.

• 9:49Ryan Holiday?

  So then it's like, you know, it's like the box of the stuff is this big, but then the book is this. So it's just slight compression.

• 9:55Speaker 01

  No, that's great. And then do they, they then get rid of the art for you?

• 9:58Ryan Holiday?

  Well, that's what they were supposed to do, but then they mailed me back the art. And now I have the same problem again. Cause now I have the book and the art, so I actually have twice the problem.

• 10:06Speaker 01

  Okay. Yeah, no, that, that's, they should take care of that for you. That should be part of the service.

• 10:12Ryan Holiday?

  I know.

• 10:12Speaker 01

  Because that's the hardest part.

• 10:13Ryan Holiday?

  Throw this away.

• 10:14Speaker 01

  Yeah.

• 10:14Ryan Holiday?

  Yeah. But it is funny, like, I think people think philosophy is impractical or theoretical or academic or whatever. And then you go, wait, this guy at a well 2,500 years ago, actually is perfectly expressing this timeless dilemma of modern life. And, and in fact, it's, it's more of a modern problem than an ancient problem because like having one cup is not that big a deal. It's like, what happens when you can mass produce unlimited cups in China? And now we're drowning in cups.

• 10:44Speaker 01

  Yeah. No, and that makes, and that for me is what makes it so powerful is that even Diogenes, having just the one cup.

• 10:51Ryan Holiday?

  Yeah.

• 10:52Speaker 01

  Decided that he didn't need that.

• 10:53Ryan Holiday?

  Yeah.

• 10:53Speaker 01

  So what am I doing with my 25 dresses, right? I mean, it's just, yeah, it's just sort of so much more crazy.

• 11:01Ryan Holiday?

  Well, and that Athens was such an affluent society that even then there's like the people who have too much and the people who don't have enough. And there's just the like, why do I need this? Do I need this water by, like, that, that people were wrestling with some of these ideas of minimalism 25 centuries ago is pretty nuts.

• 11:19Speaker 01

  Absolutely. I mean, I think, I mean, I am a classicist by training. I, I, I read and teach and. Think this for most of my waking hours. And for me, it's still completely mind blowing that A, we can read anything that they wrote or read anything about what they said and thought.

• 11:41Ryan Holiday?

  Yeah.

• 11:42Speaker 01

  And that B, it's meaningful that it translates and that it, you know, it has, has an effect that it touches you, that it makes you think about your own everyday life, that it has application.

• 11:54Ryan Holiday?

  Yeah. And that this guy, like if just the cup story would be one.

• 11:58Speaker 01

  Right.

• 11:59Ryan Holiday?

  But there's like 15 or 20 of these kind of great Diogenes things that just cut to the bone of what it means to be a person. I mean, his greatest hits album, you could put it up against any philosopher and it might actually like, there's like a couple Aristotle stories that stick with people, a couple Plato. I mean, he might have a better greatest hits than Socrates.

• 12:21Speaker 01

  Mm hmm. Especially because they are so taken from life and like, from everyday life situations. And because the way they have been passed down to us is sort of, they've been totally reduced to their essence, to their core.

• 12:39Ryan Holiday?

  Yeah.

• 12:39Speaker 01

  That's how they've been transmitted and that's why they're so powerful.

• 12:43Ryan Holiday?

  No, that's a great point. They don't survive to us in these complicated books with titles you can't pronounce. It's not Diogenes and Nicomanchian Ethics or whatever.

• 12:52Speaker 01

  Yeah.

• 12:53Ryan Holiday?

  It's just these little bits, these little stories that were powerful then, and they echoed down. Do you have a favorite?

• 13:01Speaker 01

  Oh, I was worried this kind of a question would come. I think, I'm going to say two favorites.

• 13:09Ryan Holiday?

  You can say as many as you want.

• 13:11Speaker 01

  Okay, good. So one of my favorites is when Diogenes meets Antisthenes, who has been a student of Socrates and who is living a sober, simple life. And Diogenes is very impressed with Antisthenes and he wants to study with him. But Antisthenes does not want a student, does not want anyone following him around. So Antisthenes actually beats Diogenes with his staff, right?

• 13:43Ryan Holiday?

  Yeah.

• 13:44Speaker 01

  And then Diogenes says, As long as I think I can learn something from you, you won't find a stick that's hard enough to keep me away.

• 13:54Ryan Holiday?

  Wow.

• 13:55Speaker 01

  And I, I just find sort of that, that devotion to learning and, and, and sort of that devotion to, to Antisthenes and to sort of, you know, he latched on to Antisthenes and thought there's, there's some truth there. There's something there that I need. And sort of that, that clarity I find very, very beautiful and, and sort of really, really speaks to me.

• 14:22Ryan Holiday?

  I'll give you one and then you give me your other one.

• 14:24Speaker 01

  Okay.

• 14:24Ryan Holiday?

  I like the one where somebody goes up to Diogenes and said, well, you're saying this now, but you used to say this. And he goes, yeah, well, there was a time I used to piss my bed.

• 14:33Speaker 01

  Right.

• 14:34Ryan Holiday?

  And, and so his, his ability to be a free agent and change his mind and evolve. I feel like there's not a greater expression of that idea until, you know, 2,000 years later Churchill switches parties and someone says, why are you switching parties? And he says, well, I used to think a lot of stupid things when I was a conservative. There's no implication about modern or, you know, whatever. This is British conservatives. I, I used to think a lot of stupid things and I decided not to do that anymore.

• 15:03Speaker 01

  Yes.

• 15:04Ryan Holiday?

  And, and, and this idea of like, yeah, you change your mind. So again, he just expresses just the, in such a, it's such an uncouth, but like perfect way. This is what it's about.

• 15:16Speaker 01

  Yeah, absolutely. And also it's sort of, he will always take the truth and the heart of the matter over what people expect of him. What sort of the pattern might be, what corner they want to put him in, right?

• 15:31Ryan Holiday?

  He could have said, well, it's complicated. Here's why, or actually I didn't change my, like the politician who tries to, does the somersaults to be like, well, they're not actually flip flopping. He's like, I did, I was dumb before, I'm not dumb anymore.

• 15:43Speaker 01

  Yeah, yeah, yeah, yeah. No, I mean, yeah, I mean, it boils down to. An honesty and not, you know, not trying to pretend that things are are different than they are. And yeah, and there's such a such a straightforwardness in that. And yeah, I mean, I think other anecdotes that I really like a lot are in this same vein where people take Diogenes to task for drinking a glass of wine or for eating like a certain type of food that he's supposed to abstain from, right?

• 16:14Ryan Holiday?

  Yeah.

• 16:14Speaker 01

  And, you know, for instance, someone sees him in a bar and he's like, I, you know, I saw you drinking a glass of wine in a bar. And then Diogenes says, well, if I'm at the barber's, I get my hair cut, right? If I'm in a bar, I'm gonna drink a glass of wine, right? And and it's sort of, it comes down to that same notion of, yes, in general, I don't drink wine because I don't need it and it's superfluous. But if I'm in a bar and somebody offers me a glass of wine, then there's no reason why not.

• 16:47Ryan Holiday?

  And he's not always the hero in the stories.

• 16:49Speaker 01

  Mm hmm.

• 16:50Ryan Holiday?

  Like, one of my favorite ones is the exchange between him and Plato, where he goes to Plato's house. And, you know, he's notorious for rejecting fancy things. And he gets to Plato's house and he sees Plato has lots of fancy things and he begins to stamp on his carpets. And he says, I am stamping on Plato's vanity.

• 17:07Speaker 01

  Yeah.

• 17:08Ryan Holiday?

  And Plato gets the better of him when he says, you know, how vain you are when you stamp on other people's vanity. Basically, there is a kind of like immaturity and egotism to Diogenes. He's better than everyone, smarter than everyone, less attached than everyone. And it must have also been pretty insufferable.

• 17:31Speaker 01

  For sure. Yeah. And this is where Plato is so right in that moment, that Diogenes needs an audience.

• 17:41Ryan Holiday?

  Yes.

• 17:41Speaker 01

  And that that is.

• 17:42Ryan Holiday?

  He's like a punk performance artist.

• 17:44Speaker 01

  Exactly. Exactly. And people need to see him, right? He needs to be seen for his message to come across. And that is the. Fundamental impurity of his thought.

• 17:57Ryan Holiday?

  Yeah.

• 17:57Speaker 01

  That he cannot fully live out his independence unless somebody sees it.

• 18:03Ryan Holiday?

  Yeah.

• 18:03Speaker 01

  Right? But I think that the fact that he embraces that impurity.

• 18:08Ryan Holiday?

  Yeah.

• 18:09Speaker 01

  Right? That he does not try to reason it away or deny it or sort of, you know, find a loophole to make sense of it.

• 18:16Ryan Holiday?

  Yeah.

• 18:17Speaker 01

  I find really disarming. Right? And I think that there's something so important about that impurity.

• 18:24Ryan Holiday?

  Yes.

• 18:25Speaker 01

  Because I think it's precisely sort of the search for watertight, complete philosophical systems.

• 18:33Ryan Holiday?

  Lama or the pope. He's not infallible, perfect.

• 18:36Speaker 01

  Yeah.

• 18:37Ryan Holiday?

  He's not this like holy figure. He is this flawed human being who in challenging the conventions as aggressively as he does, often finds wisdom and truth. And sometimes you go, well, I'm glad you tested that hypothesis for us, but I don't think I want to live in a jar.

• 18:55Speaker 01

  Right? Yeah. And it's also like, the way that he is living is the way in which he interprets what it means to live in accordance with nature.

• 19:07Ryan Holiday?

  Yes.

• 19:07Speaker 01

  And he is offering that to us as a performance that we can then interpret. But if we think about the course of antiquity and if we think about what people in the past did with Diogenes and how they responded to him, they didn't copy his behavior.

• 19:25Ryan Holiday?

  Right.

• 19:25Speaker 01

  Exactly. But they were still very inspired by it.

• 19:29Ryan Holiday?

  Yeah.

• 19:30Speaker 01

  And sort of a good example of this is where in a later period in time, Dio Chrysostom and Julian, right? These are people who live a few centuries later, try to make sense of Diogenes defecating in public in the marketplace.

• 19:47Ryan Holiday?

  Right? And worse things.

• 19:48Speaker 01

  And worse things.

• 19:49Ryan Holiday?

  Let's say more inappropriate things.

• 19:51Speaker 01

  Yes. Yeah. Exactly. Exactly. And for Dio Chrysostom, there's this sort of real emphasis on the shamelessness and that he is not threatened by people trying to destroy his reputation.

• 20:07Ryan Holiday?

  Yeah.

• 20:08Speaker 01

  Right? And for Dio Chrysostom, this is really important because he is being exiled by imperdomination and is having his. Honor removed, he can no longer be an abstending member of the polity. And he's trying to come to terms with that. And he sees and hears this story about Diogenes in his mind's eye. And he thinks, well, Diogenes was not ashamed in that moment. Diogenes was not ashamed in that act. So I'm not going to be ashamed about being chased out of Rome. Right? And I think sort of that, the fact that he can take that moment and, and take something out of it that's useful for him and that he can sort of understand Diogenes's behavior

• 20:51Speaker 01

  in his way, instead of making fun of it, or sort of like, you know, being horrified or being disgusted, right? But, but actually take something from it that's not a carbon copy, right? He doesn't go around pretending to be Diogenes, but he still gets so much out of it.

• 21:07Ryan Holiday?

  Yeah, in a way, he's, he's a performance artist and a philosopher. So he's kind of like a Marina Abramovic kind of character where you're like, okay, the message of the artist is present is not that you have to sit at a table for 30 consecutive days. It's like, can you do it for five minutes? It's a statement about how society is missing a thing, or how hard a thing actually is. And should it be hard? And what does it mean that it's hard? And so, yeah, a lot of the extremeness that his stunts go to, like an artist, are designed to shock and catch your attention. And then when that wears off, make you question some underlying convention, or status quo, or, you know, your own participation in that world.

• 21:49Ryan Holiday?

  You're not supposed to sell all your things and move into a barrel. He already did that.

• 21:54Speaker 01

  Right.

• 21:54Ryan Holiday?

  And then you can fall somewhere along that spectrum after you've derived the lessons from that.

• 22:01Speaker 01

  Yeah, and I, I think that if Diogenes were alive today, and if it was possible to talk with him, you know, I do think he would keep pressing us.

• 22:12Ryan Holiday?

  Sure.

• 22:12Speaker 01

  I, I do think that like every step of the way, he would say, well, Do you think you have done enough?

• 22:18Ryan Holiday?

  Sure.

• 22:18Speaker 01

  And do you really think that this is the best, most just way that you think you can live? Right? He always turns it back to us.

• 22:27Ryan Holiday?

  Right.

• 22:28Speaker 01

  So he would keep asking the questions, but he's not expecting anyone to become exactly him.

• 22:36Ryan Holiday?

  Right.

• 22:37Speaker 01

  That would horrify him, right? That like runs totally counter to the way that he thinks and the way that he is.

• 22:43Ryan Holiday?

  So for people who aren't familiar with him at all, let's start where he starts. How does he end up as a philosopher in Athens? He's in exile, right?

• 22:50Speaker 01

  Yes, that's right. So Diogenes is born in probably a pretty well-to-do family in a town that's called Sinope. And it's on the coast of the Black Sea. And today it's in Turkey. And he grows up there with his, with his family. And at a certain point, either just him or him and his father get exiled from Sinope. So they have to leave. They cannot live there anymore, most likely because there was some problem with the coinage, with the, with the mint. So Diogenes's dad was in charge of, of the mint. And there was some irregularity that led to them having to leave.

• 23:33Ryan Holiday?

  He could have been a counterfeiter. He could have been stealing in some way.

• 23:37Speaker 01

  Yes. Yeah. I mean, the sort of, there's, there's, there's a Greek word that's used to describe it that can mean both making, making false coins or damaging coins that have already been made.

• 23:49Ryan Holiday?

  Yeah.

• 23:49Speaker 01

  So, so that's sort of where the ambiguity is. Then, you know, the amazing thing is that there are some coins that have Diogenes's dad's name on it. And there's also some damaged coins, you know? So there's some corroboration, but it's, you know, it still doesn't get us quite to knowing exactly what happened. But, you know,

• 24:09Ryan Holiday?

  That's insane. Just like the level, that like the level of detail would still survive to this day, that you can verify some tiny claim in one ancient philosopher's text.

• 24:20Speaker 01

  Especially for Diogenes, because about him, like people are always ready to say, oh, it's just sensationalism. Oh, it's just made up. Right? So when for Diogenes, you find like a snippet like that in, in the material record, that's just amazing. It's just insane.

• 24:35Ryan Holiday?

  Yeah.

• 24:36Speaker 01

  In any case, Diogenes can stay in Sinope, and he goes first to Athens, which at the time really is the intellectual center of the world. So I should say, Sinope, where he's from, is not a backwater either. It's an important trading city and it's sort of very interestingly on the border between the Greek and Persian spheres of influence. And it sort of, you know, changes pans a couple of times in Diogenes's lifetime. So that's an important city too. But he gets exile, which means he loses his citizens' citizen rights in that place and ends up in Athens, which to him ends up being really exciting.

• 25:19Speaker 01

  Right? A few times he says like, well, the Sinopians might have convicted me to exile, but they have convicted themselves to staying in Sinope. So not all that bad out.

• 25:40Speaker 01

  In Athens, he meets Antisthenes, who was a student of Socrates and who sort of sets him most likely on the path of philosophy, even though in Sinope already he might have sort of picked up on some of his ideas from influences from the north in Skithia and influences from the east in India. It's really in Athens that he comes into his own and also people get to know about him. That's sort of, that's the nice thing about being at the intellectual center of your time, that people also get to know about your ideas.

• 26:14Ryan Holiday?

  This is right after the death of Socrates?

• 26:17Speaker 01

  Yes. Yeah. Yeah. Yeah. So a few decades after the death of Socrates, which is still, you know, very reverberating for people and Socrates is-

• 26:26Ryan Holiday?

  And this philosophy thing is kind of new. Like not, obviously we go, there's the pre-Socratics and then the post-Socratics, but it's like, it's still up for grabs what this philosophy thing is going to be and mean to the Western world, because it's all being figured out just then.

• 26:45Speaker 01

  Yeah. I mean, it's a very vibrant time for it. And if we think about ancient wisdom and people trying to figure out how the world works, if there are gods, what they are like, I mean, this is something that people have- Been doing for at least two centuries already at this point. But at this time, 4th century BCE in Athens, there is a very vibrant competition over what philosophy should be, what it should be like, what kind of questions should be pursued, and in what way they should be pursued. So in that sense, this is a perfect time for Diogenes to show up there.

• 27:25Ryan Holiday?

  And I think we sometimes think of the kind of classical Athens as this like, you know, people walking around in togas, the statues are shiny, or the marble is shiny, the statues are painted. It's this beautiful kind of like, we've, it's like, oh, this is like before it turned into ruins, which it was, but it was also like in quite a lot of flux. And like, Socrates lives through a great power conflict, there's wars, and then Diogenes is right there in the middle of the reign of Alexander the Great, who's in the middle of gobbling up the world, not unlike, now he's exactly comparable, but not unlike a Napoleon or a Hitler, where just one guy is just remaking the world violently in his image.

• 28:09Speaker 01

  Yes, yes. And, and this is something that people don't know and can't know at the time, but when Diogenes is born, there's still sort of notional independence for, for the Greek city-states. And by the time he dies, there is not, and it's never really going to come back. So, so in that sense, he, he lives through this pivotal time. And, and it's also this sort of really deep irony that sort of the most anti-authoritarian, anti-autocratic philosopher lives through the advent of Philip and then Alexander taking

• 28:53Speaker 01

  over in the Greek-speaking world, who, who are Autocrats and, you know, ultimately with some twists and turns still will pave the way for Rome to take over, which ultimately also devolves into autocracy. So, so it is sort of this really strange moment to think that Diogenes still had, you know, both feet in these two worlds.

• 29:15Ryan Holiday?

  Well, and that's why I think their philosophy is so relevant throughout history is that it wasn't like it, they had all the same problems that we have now. And they had demagogues and disruption and I mean, they, they lived in an uncertain future. They did not know they lived in classical antiquity.

• 29:33Speaker 01

  Absolutely.

• 29:34Ryan Holiday?

  Like it was all topsy turvy, scary. What's happening today? Here's the new latest news from, you know, the distant lands of the like, they were experiencing most of the same feelings that we're experiencing today.

• 29:47Speaker 01

  Yeah. Yeah. And I also, I also really like what you said about when we think about ancient Athens, we think about opulence, shiny temples, people having their lovely dinner parties. And obviously that was going on. People were wealthy and were sort of engaging in these amazing building projects, but people were also trying to scrape by and sort of make a living and have this hard knock life on, you know, on the margins of society. And there again, Diogenes is such an interesting figure because he interacts with both worlds. He is invited to Plato's house to a dinner party and can trample on his carpet, but he

• 30:30Speaker 01

  does live with the poorest of the poorest and ajar on the streets. So he's also sort of experiencing both sides of that.

• 30:40Ryan Holiday?

  And at least according to the legend, interacts with Alexander the Great directly.

• 30:45Speaker 01

  Yes.

• 30:46Ryan Holiday?

  So you have the intersection very, there's a couple of these examples in antiquity of like a powerless philosopher interacting with a incredibly powerful emperor type.

• 30:58Speaker 01

  Yeah. Yeah. So the, the story of Alexander and Diogenes, especially because as you say, it conforms to this type.

• 31:06Ryan Holiday?

  Yeah.

• 31:07Speaker 01

  Right? There are quite a few people who will say it's too good to be true. It's, you know, as a story, it's too good to be true and it probably didn't happen. And what I did in doing my research was, well, I'm really interested in finding out.

• 31:23Speaker 01

  When people first started to say that it didn't happen.

• 31:26Ryan Holiday?

  Sure.

• 31:26Speaker 01

  Right? So I sort of like went back in time in the, in the research and sort of like tracing people's footnotes and who refers to whom and like, how, like, how does this get started? And then what I found was sort of that this suspicion of, of the, of the meeting actually happening starts with this French scholar who himself does not doubt the meeting at all.

• 31:53Ryan Holiday?

  Oh.

• 31:53Speaker 01

  He just says that some of the sources about the meeting are questionable. This guy's name is Pierre Bale and what he starts to do is he takes all of these narratives about the ancient philosophers and sort of starts to subject them to criticism. Like, like, do we think this actually happened? Right? Which is a fairly revolutionary thing.

• 32:14Ryan Holiday?

  Does Chrysippus actually laugh himself to death?

• 32:16Speaker 01

  Exactly.

• 32:16Ryan Holiday?

  Probably not.

• 32:17Speaker 01

  Right, yeah.

• 32:17Ryan Holiday?

  But, but, but these things were presented unquestioned by the ancients, like in book after book after book.

• 32:24Speaker 01

  Yeah, for the most part, yeah. I mean, you know, even in antiquity, some people will say, ah, some people believe this, some people don't, right? Even in antiquity.

• 32:34Ryan Holiday?

  But it'll be like, this happened and this happened, but clearly only one of them could have happened.

• 32:37Speaker 01

  Right, exactly.

• 32:38Ryan Holiday?

  But it's more like, no, my job was just to list to you all the things that people have said happened.

• 32:42Speaker 01

  Yeah, yeah, yeah.

• 32:43Ryan Holiday?

  It's a different understanding of history, not the singular narrative, but the, but the multitude, yeah.

• 32:47Speaker 01

  Yeah, the multitude and, you know, the importance of passing down these multiple versions so that, you know, at a later moment in time, people can make up their own minds, right? But, but I would say that before this guy Pierre Bale comes along, there is a little bit of a sense of like, well, let's just go with the best story.

• 33:05Ryan Holiday?

  Yeah.

• 33:05Speaker 01

  Right? And let's just go with the stories that we have. Uh, and then he starts to be much more critical. Um, but when it comes to the meeting of Diogenes and Alexander, Pierre Bale, like, he actually does believe it happened. He just thinks that Seneca's version of it in particular contains some problems in the sense that in that version, Alexander is already presented as being godlike and ruler of the world. And the reason why that is a problem is because Alexander and Diogenes, they actually meet before Alexander goes on his eastern campaigns and then Alexander famously never comes back to Greece.

• 33:42Ryan Holiday?

  Sure, he does, yeah.

• 33:43Speaker 01

  Yeah, exactly. So, so the language that's used in that description of the meeting can't be right because it causes a chronological problem.

• 33:51Ryan Holiday?

  Sure.

• 33:52Speaker 01

  At the same time, there are other accounts of the meeting, right?

• 33:57Ryan Holiday?

  Yeah.

• 33:57Speaker 01

  That don't have that problem at all.

• 33:59Ryan Holiday?

  Right.

• 33:59Speaker 01

  And this is why Baio himself says, well, Seneca's version is not great, but it did happen. And then there's, and there's these other versions. But sort of then later scholars only take, Seneca's version cannot be right.

• 34:13Ryan Holiday?

  Yeah.

• 34:14Speaker 01

  Right? And they

• 34:14Ryan Holiday?

  Interesting.

• 34:15Speaker 01

  run with that, right?

• 34:16Ryan Holiday?

  And Seneca's like 500 years after this happened.

• 34:18Speaker 01

  Yeah.

• 34:18Ryan Holiday?

  Yeah, 400 years after this happened.

• 34:20Speaker 01

  And then very quickly, it becomes the meeting of Alexander and Diogenes, which has been roundly dismissed so many times, we don't even have to think about it anymore.

• 34:28Ryan Holiday?

  Right.

• 34:29Speaker 01

  And the, I mean, when I sort of went back this, you know, went back down this chain of transmission, I was really dissatisfied with the case that people were making for the meeting not happening. And I end up saying in my book that I think, you know, as, as far as we can know anything for sure about antiquity, I think it's very likely that it didn't happen. They were in the same place at the same time. Alexander could very easily have known about Diogenes from Aristotle and from this other guy, Onasichritus, who they knew in common. Alexander has an interest in philosophy. And, and we have sort of good reasons for why the meeting would have been reported on,

• 35:10Speaker 01

  namely by, by this guy that they know in common, Onasichritus. So for me, it seems like sort of this whole notion of, oh, it's too good a story to be true.

• 35:22Ryan Holiday?

  Yes.

• 35:22Speaker 01

  Right? And then one of the other lines of argument is like, well, why would Alexander have wanted to meet Diogenes, which sort of, you know, goes to the heart of Diogenes's reputation problem and this idea of, of Alexander being, you know, being sort of this very elevated, regal, royal figure who would not go and talk to essentially a homeless person.

• 35:43Ryan Holiday?

  Yeah.

• 35:44Speaker 01

  And that, I mean, for me, those, for me, those arguments against just Weren't good enough anymore.

• 35:50Ryan Holiday?

  No, I don't think so.

• 35:51Speaker 01

  And then precisely because we have this connection for how the story might have gotten to be recorded and some of the Greek texts that we can still read about it, that for me is like, you know what? I think this actually happened.

• 36:05Ryan Holiday?

  Well, if it didn't, we would have to invent it happening because it's so perfect, right? The most powerful man in the world and the powerless person. And ultimately, one is more powerful than the other.

• 36:14Speaker 01

  Right.

• 36:14Ryan Holiday?

  Right? Like, you know, one conquers the world, the other conquers the need to conquer the world. And that's so, the symmetry of it is beautiful. Are we sure that Diogenes exists? Like, I know with Socrates, it's like, how do we know? Or Jesus, how do we know? There's not so much evidence. Where does he fit on that spectrum? Like, are we absolutely positive that it's not all a literary invention?

• 36:37Speaker 01

  I think that the coin that has his father's name on it, right, is a really, really powerful sort of point in his favor of existing. And then there's also a Papyrus text that describes an anecdote which features Diogenes, which is not as famous as some of the other texts because the Papyrus scrap itself was discovered relatively late. So it sort of doesn't come part of the stories that we tell about Diogenes. But this Papyrus text is, the text is sort of dated as having been written within, let's say, 60, 70 years after Diogenes's lifetime. So I think.

• 37:21Ryan Holiday?

  There was a guy named Diogenes.

• 37:22Speaker 01

  Exactly.

• 37:23Ryan Holiday?

  It would be, yes.

• 37:24Speaker 01

  Yeah.

• 37:24Ryan Holiday?

  Guy.

• 37:28Ryan Holiday?

  Thanks so much for listening. If you could rate this podcast and leave a review on iTunes, that would mean so much to us and it would really help the show. We appreciate it and I'll see you next episode.