Timothy Denevi on the Power of Reading and Learning from the Past (Part 2)

Ryan speaks with assistant professor and MFA program at George Mason University, Timothy Denevi The economics of a book being different than the media, How much do you internalize the tumult and danger around you as a journalist, Fundamentally journalism is a form of lying and an act of aggression and his book Freak Kingdom · Hunter S. Thompson's Manic Ten-Year Crusade Against American Fascism.✉️ Sign up for the Daily Stoic email: https://dailystoic.com/dailyemail🏛 Check out the Daily Stoic Store for Stoic inspired products, signed books, and more.📱 Follow us: Instagram, Twitter, YouTube, TikTok, FacebookSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. 📢 Share | ⚙️ Manage Subscription

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

• 0:03Ryan Holiday?

  Welcome to the weekend edition of the Daily Stoic. Each weekday, we bring you a meditation inspired by the ancient Stoics, something to help you live up to those four Stoic virtues of courage, justice, temperance, and wisdom. And then here on the weekend, we take a deeper dive into those same topics. We interview Stoic philosophers. We explore at length how these Stoic ideas can be applied to our actual lives and the challenging issues of our time. Here on the weekend, when you have a little bit more space, when things have slowed down, be sure to take some time to think, to go for a walk, to sit with your journal,

• 0:46Ryan Holiday?

  and most importantly, to prepare for what the week ahead may bring.

• 0:53Ryan Holiday?

  Hey, it's Ryan Holiday. Welcome to another episode of the Daily Stoic Podcast. Last week, I brought you part one of my conversation with Timothy Dennehy, who wrote this awesome book called Freak Kingdom, Hunter S. Thompson's manic tenure crusade against American fascism. One book that I absolutely adore, Carrying in the Painted Porch. We don't carry a lot of sort of current events, like books that don't fit in clear categories. And this is one, and I really think you should read it. He's written for The Paris Review, The New York Magazine, Literary Hub. I read this great piece he wrote about Joan Didion, who, by the way, you've listened to the podcast more than once. You've already picked up on this. I'm a huge Joan Didion fan, and so it's cool for him to sit on the table, which is Joan Didion's table, was sit in the chair in my office where I'm sitting in as I'm reading to you right now.

• 1:38Ryan Holiday?

  I really liked this book. Again, when I rave about books, I'm really raving about books. Like, I took some notes when I was writing this book. I was like, this book is better written than it should be. Like, Tim is an academic. He's a professor at George Mason. And a lot of books written by professors, they're factually correct. The scholarly work is important, but they're not great at writing. And you can tell this dude has been schooled in creative writing. He knows what he's talking about. And it was just a really awesome conversation. I think you're going to enjoy part two. If you haven't checked out Freak Kingdom, you absolutely should. I'll link to it in today's show notes. But go ahead and check it out. And here's my conversation on Hunter S. Thompson, America, and what we can learn from the past political moments about the moment we're in right now.

• 2:27Speaker 01

  I don't, I don't, I don't know what's happening to the Western mind, but I will say the literal relationship to fact, especially in the last 10 years, is mind blowing to me. We don't just have to go back to the 60s and the idea of exaggeration and art, you know, and all of these different emotional versus, you know, other types of truth. I, I wrote a lot about the historical Jesus in gospels. That idea that you could keep two things in the human mind at once, that of course, this is exaggerated to prove a point. And still, this is a narrative that feels true or I want. You know, it doesn't have to be either or.

• 3:07Ryan Holiday?

  Sure.

• 3:07Speaker 01

  And I, our either or moment blows my mind right now, you know? And then, I mean, at least hypocrisy, which is what Thompson was talking about so much then, but which is really dangerous because it's, my, my fiance will say like, "We're not thinking well, like, we're not thinking well if everything has to be a dichotomy or a black and white, yes or no situation." And that response is similar to what you're talking about to what I think's going wrong right now. You know, and I, I just think Thompson was so good and so many of those. I mean, what is, what is, Conrad would say like, "Life is short and art is long and success is very far off." You know, that this is something that's been practiced and engaged for so many thousands of years by so many people. And to take not just our lens right now and map it on to the more recent American past

• 3:51Speaker 01

  or whatever, but to think that it's always been this way. And we're not in a conversation with the technology that's all around us, you know, the voices of people that are long gone. To me is mind blowing and I, I think we're getting stupider because of that. And I, I sound so old, it kind of blows my mind, but we need to think, I don't know how we're going to think better if we can only think in yes or no.

• 4:10Ryan Holiday?

  I mean, I think if you watched the tape of Hunter S. Thompson at the Kentucky Derby, and then you read the story, you'd be like, "Oh, you made the entire thing up." But that's not what that story is about. He's, he's, and the same if you, if you actually, what could you verify from those trips to Las Vegas? Probably more of it is not true than is true.

• 4:32Speaker 01

  Yeah.

• 4:33Ryan Holiday?

  But the book's not about what happened in Las Vegas. The, the book is about the high watermark of the 60s. It's all about that observation. It's about... The essence and the vibe and the feeling that he's trying to capture. And what new journalism was, was a kind of emerging of fiction and nonfiction.

• 4:51Speaker 01

  Exactly.

• 4:51Ryan Holiday?

  And comedy does that now, too. And you're, yeah, you're missing the point if you try to be this sort of strict literate. Like, there's a difference between, the irony then of simultaneously being a culture where you have someone like Trump who is objectively a liar, but people accept it because they want it to be true, or because it feel like, like to have literally the most dishonest person to ever hold the office, simultaneously be popular with a large segment of the population because he is a truth teller, is this weird double standard where like, the people that we should be hearing

• 5:35Ryan Holiday?

  the emotional truth from, we hold literally, we hold to the standard of literalness. And then the people who are actual officials or scientists, except who we need to be holding to a literal standard, we allow to get off with, well, they're telling me what I want to hear. It's a very strange situation.

• 5:54Speaker 01

  And I mean, it reminds me of in kind of a gentle way, but you know, the passage in Didion's The White Album, where she's with Jim Morrison?

• 6:01Ryan Holiday?

  Yeah.

• 6:02Speaker 01

  You know, and you know how she writes about it, it's, she goes to the recording session, they're waiting for Jim Morrison, he shows up, he doesn't talk to anybody, you know, he's like, should we do this? And, you know, and they're like, we can't. And Didion's like, I don't even know in whose favor the conversation, you know, was determined. In real life, what happened, Evie Babitz, her friend talks about this, who had dated Morrison, brought her there, she was flirting with Jim Morrison, he was throwing the matches at her. It was such a different reality than how she articulated it. That piece's emotional truth is mind blowing. I love that passage about how she captures. What the doors are expected to be, what they are.

• 6:37Ryan Holiday?

  Yeah, they're like, should we go, they're like making like trap, they're supposed to be this revolutionary artistic, you know, whatever group and there's like, should we drive back from West Cove?

• 6:45Speaker 01

  Yeah, exactly.

• 6:46Ryan Holiday?

  It's just this, it's so, she presents them as so pedantic and ordinary that it essentially like flays them.

• 6:53Speaker 01

  Yeah.

• 6:53Ryan Holiday?

  And yeah, why is she doing that? That's I guess a different question, but yeah, the idea that it could have happened very differently.

• 7:00Speaker 01

  Exactly. And then still, everything's true there. She had a fact checker. She just chose to leave out certain other parts. And I think she did a very nice job of capturing what we thought a rock band was.

• 7:10Ryan Holiday?

  Yeah.

• 7:10Speaker 01

  Leather pants.

• 7:11Ryan Holiday?

  Yeah.

• 7:11Speaker 01

  Sex and death, you know, and then the kind of everyday nature of it and that, you know, is.

• 7:16Ryan Holiday?

  Like four coworkers or whatever.

• 7:17Speaker 01

  Yeah, exactly. And there's like, they're eating like boiled eggs out of a paper bag.

• 7:20Ryan Holiday?

  Yeah.

• 7:21Speaker 01

  Like she's counting the number of buttons on the control panel. But even then, she's narrowing from reality, all the different things that did happen that night.

• 7:30Ryan Holiday?

  Yeah.

• 7:30Speaker 01

  Into her version of what she wants to say and nothing is untrue.

• 7:33Ryan Holiday?

  Yeah.

• 7:34Speaker 01

  About that. It's just think of all she leaves out to get there. And I, I think we are even struggling to understand that in terms of subjectivity and nonfiction and truth.

• 7:42Ryan Holiday?

  Yes.

• 7:43Speaker 01

  Being present right now.

• 7:44Ryan Holiday?

  Well, I, I actually, this is the epigraph is to Trust Me, I'm Lying is the James Aggie quote, where he's basically saying that fundamentally journalism is a form of lying. Because you're taking disparate events and coordinating them to tell a story that you want to tell. And, and you're leaving things out. And then there's that famous, what's her name? The journal Janet Malcolm thing about how fundamentally journalism is also this act of aggression and hostility.

• 8:09Speaker 01

  Yes.

• 8:10Ryan Holiday?

  Didion talks about this too, where you're like, you're, you and the source have an adversarial relationship. And you're just looking for where you're going to bury the knife.

• 8:20Speaker 01

  Yeah.

• 8:21Ryan Holiday?

  And if you don't put the knife in, it's only because you're using them in some ways to get up to someone else or something else, or they fit your, and so, yeah, we don't see journalism that way. Because again, coming out of the sixties, we see it as this.

• 8:41Ryan Holiday?

  Inherently noble pursuit is speaks truth to power, brings out presidents, which it does. I was telling Hassan that, I was saying like, obviously post writing, trust me, I'm lying. I have this relationship where I see clearly the importance of journalism. I mean, especially when you have sort of a neo fascist movement. You have disinformation and misinformation where real lives are hanging the balance. And at the same time, when I watch stories like what happened to him, or I watch. So miss the boat on other things, you go, oh, yeah, you're like, you are also part of the problem. You're like, you're like, the, I don't know what the alternative is, but like, you're complicit

• 9:24Ryan Holiday?

  in the whole system too, and you are as much a vehicle for untruth as you are truth.

• 9:29Speaker 01

  Exactly. I think Barry Weiss's response to the, it's been amazing, the Israel Palestine conflict, we got to that topic very quickly, but the way that she's covering that ever since, and since early October has been brilliant and has a way to cut through what's inhibiting or the failures of major journalistic outlets right now.

• 9:50Ryan Holiday?

  Yeah.

• 9:50Speaker 01

  And dealing with, I mean, sending reporters out, talking to people on the ground. She, with her podcast and with the Free Press has done an amazing job. That's kind of the more, I mean, in a tough time, saving lives, a brilliant way, I think, of dealing with it right now.

• 10:03Ryan Holiday?

  Well, and then that, there is no such thing as a perfect messenger, right? So like, I, I know Barry, I like Barry, I think she's carried water for the wrong people quite often, and then there are moments where she really nails it, right? And I think you could make the same point about Hunter Stop there are a lot of great, and it's like, they're, sometimes they get it right, and sometimes they don't, right? And some, you sort of, that's why you have to have this broad group of people you get your information from, you can't just, oh, I just read this, you know? The dumbest people I know just get their news from the television. Do you know what I mean? Like, you go, oh, okay, this is a problem.

• 10:41Speaker 01

  And that's, it's so hard though, because I wish my father would watch CBS News, you know, like instead it's on Facebook. Like, I, I think that you're right. I, I think that. We've also lost the idea of getting news, of getting an information and perspective by a four hundred page book.

• 10:59Ryan Holiday?

  Yeah.

• 10:59Speaker 01

  Written forty or fifty years ago.

• 11:00Ryan Holiday?

  So that's why I loved your book. So like I have found like, okay, the best book I read during COVID was John M. Berry's book, The Great Influenza.

• 11:08Speaker 01

  Oh, wow.

• 11:09Ryan Holiday?

  Right? So you're reading about the Spanish flu and you're like, okay, here's everything that's true, right? The best way I understood Trump was Sinclair Lewis's It Can't Happen Here. And I feel like your book actually, which was based on the generation right after that book, like you're talking about, no longer does the fascist movement look like Mussolini or Hitler. It's figure out how to dress better. It's figured out how to co-opt certain kinds of speech and language. It's less, it's more velvet glove, you know, than than iron fist. But Hunter S. Thompson is writing about the exact same things that are happening right now. The same types of politicians, like my understanding of

• 11:53Ryan Holiday?

  the civil rights movement and has changed how, when I look at some of these governors, like when I look at the governor of Texas, when I look at DeSantis, I understand them now through the lens of George Wallace or this certain kind of southern governor. Same with some of the senators, but you're like, oh, this, this is a type of person, just like there's types of movies. This is a type of person. And this person has something that resonates with large groups of people for long periods of time. You have to understand the game that they are playing.

• 12:28Ryan Holiday?

  And you have to take that very seriously. And I I found that people don't have the historical basis to do that. So they just look at, oh, DeSantis doesn't like the people that I like or whatever. And and you're not getting the game that he's playing and how dangerous it actually is and where where it inevitably ends up.

• 12:47Speaker 01

  Where it leads to.

• 12:48Ryan Holiday?

  Yeah.

• 12:48Speaker 01

  And the inherent like. Fragility to our system that we kind of take for granted. You know, how can be co-opted, very, it can be co-opted in the ways you're exactly talking about. I mean, I always think about how George Wallace Thompson wrote about this. You know, is running for president in 1972 on an independent platform. Will be shot eventually in only Maryland, but this is when he's still kind of ramping up. There's other candidates, other Democratic candidates going to Florida, trying to win. You have Muskie taking the whistle stop tour, you know, down, trying to coordinate everything perfectly. And George Wallace just goes to a NASCAR event. He has 300,000 people in the audience. He speaks beforehand and he is reaching everyone.

• 13:30Speaker 01

  He is getting the free publicity and the exposure that the other candidates are paying everything they have and positioning themselves to somehow reach and instead are just getting further away from the voters that they want.

• 13:42Ryan Holiday?

  Yeah, he understands where the people are and what they want to hear.

• 13:45Speaker 01

  Yeah.

• 13:45Ryan Holiday?

  And, yeah, right. And if you don't have the conscience that protects you, it's a problem. So you, you need politicians who are astute, artists who are astute, critics who are astute, to understand what's happening and to not just let it happen and report on it as it's happening.

• 14:06Speaker 01

  Exactly. And I, you know, I thought about that a lot when, you know, it was whatever our present day moment is, it's not any more difficult than all the ones from the repeated past, you know, going back thousands and thousands of years. And it's not more singular, but it is, you know, like all those other moments, it's its own version. And when I was in a bad media diet where I still am, I'm sure, you know, outrage was generating what I was reading in the New York Times, what I was reading in the New Yorker.

• 14:33Ryan Holiday?

  Sure.

• 14:34Speaker 01

  Well, I find the writer that's expressing the emotion I feel right now.

• 14:37Ryan Holiday?

  Yeah.

• 14:37Speaker 01

  You know, please, Adam Gopnik, like say what I feel. I, I realized like going just back into the past, even a few generations, to, to try to look at the same issues and the, and the same, you know, human conflicts that we're seeing now was a way to kind of access both the present and what I was trying to say or think about the present in a better way.

• 15:00Ryan Holiday?

  Well, the idea, the, the economics of a book are fundamentally different than the economics of media, right? Like a book is designed.

• 15:09Ryan Holiday?

  The newspaper story you read or the online article, whatever, is designed to be replaced immediately by the next thing the next day. We're now on the internet, the next tweet five minutes later. A book, because it takes so long to do, by definition, has to have a little more staying power, right? It has to have, it has to continue to be true for longer, has to have a larger view normally. And then I think this is the most important part. It's fundamentally different about what we would call journalism, is that you pay for it individually, right? Not even, there's a problem with, like, as they say, if it's free, you're the product that's being sold. But an article inside a package of other information, right,

• 15:52Ryan Holiday?

  is different than this, which is designed to be self-sufficient and self-justifying. Like, you buy this, you read it, it is worth what you paid for it. That is a different value proposition with a different set of incentives. And people don't really think about the incentives that are operating under the information that they're consuming and how those incentives are warping and changing that information. And if you can't see that, then you fall prey to that bias. Just like people who spend too much time on Twitter get their brain warped, people watch too much news, TV get their brain warped. If you're only reading books, you also can live in this world

• 16:33Ryan Holiday?

  where there's only these big truths and not real events happening on the ground. So you need a balance, but I think fundamentally, it's better to go back further, it's better to read things that are older. It's better to read things where the significance of the partisanship has gone away, right? So when you're reading about Hunter S. Thompson and his judgments on Nixon, even if you're a Republican, you don't give a shit that Nixon is a Republican. Do you know what I mean? It's so long ago. And he's not gonna come back. It's like, oh no, he's gonna come back and take over. Yeah, you're just, you're just thinking of him and whether his judgments of that person's character or flaws or decisions were right or wrong.

• 17:17Ryan Holiday?

  The greatest biographer of all time is Plutarch, right? Plutarch is writing not whether, and he admits, he goes, "I don't know if all this stuff is true or not." And, and he's like, "And I'm not gonna tell you exactly where they were born, what they lived, how this happened." He's like, "Because an action or a word or an anecdote is more revealing about the essence of what's true than anything else." And so when you read about Alexander the Great, or when you read about the Catiline conspiracy, you know, you're thinking, um, oh, this is what human beings do. This is bad. This is why, you know, this or that. Well, the same thing is happening right now on January 6th or whatever. And then you're able to go, okay, what, what my party is saying I should think here,

• 18:00Ryan Holiday?

  or this outlet is saying, oh, you're able to get to the, at the historical essence and the timelessness of that, um, which is really ultimately what matters.

• 18:09Speaker 01

  Yeah, I mean, I, I had read the Catalinian orations probably 25 years ago. Some of the first Latin.

• 18:15Ryan Holiday?

  Yeah.

• 18:15Speaker 01

  I was like trying to find the verb and the tense. But still, um, Cicero, like indicting Catiline. And I didn't think of it again, I mean, 25 years later, until after January 6th, I had been there reporting and I, I remember the Catalinian orations. Now, I'm not going to tell you that he, I remember the devices and I remember the stakes in a way that I had forgotten, you know, the way that that came back. It kind of blew my mind.

• 18:36Ryan Holiday?

  Well, yeah, you have this guy who feels entitled and like he's earned it and that he should be in charge. And then somebody else wins. And then he's, he, even though he couldn't be close, he couldn't be further from the mob or the, the population. He stirs them up and six them on the establishment. And then, you know, then there's also, interestingly enough in there, I've kind of, kind of the overreaction of Cicero. Like Cicero wants this to be the crisis of his lifetime. And the irony is it's not. It's, it, it, it's not minor, but it's the, the, it was probably never going to work.

• 19:21Ryan Holiday?

  And in his overreaction to it ironically sets up

• 19:28Ryan Holiday?

  his lack of credibility when he really could have been necessary when the Republic is overthrown, you know, just a few years later. And so like,

• 19:38Ryan Holiday?

  We previously would have had a culture where everyone read that when they were learning Latin. And then they didn't learn Latin, so you don't read it. And then you go, why? If it's not about learning Latin, why would we study this? It's a long time ago. It's old, dead, white guys, whatever. And then we don't have the shared cultural consciousness to be able to draw, like, to understand why we have the norms that we have, why we have the words that we have. Like, how many people even know that it's the riot at the Capitol is named after Capitoline Hill? You know what I mean? And that the center, all these words come from the thing. And if you don't understand that, the significance of each one of the things don't matter. And you can end up in a place where it's all kind of emptied of significance.

• 20:23Ryan Holiday?

  And then the stakes, which are quite high, don't feel as high as they are.

• 20:27Speaker 01

  You know, I was on a panel last week at the University of Virginia called the Canonical and the Band. This is about the canon and banned books. You know, and I, I, I, one thing I thought about talking with the Pheno-Polo, they were great. The canon's a living thing. We think of the canon as this old thing that needs to be rejected or accepted. But, and this is a more, you know, recent experience. The canon is something we're constantly responding to and saying like, was Cicero as good as we thought? You know, like, was Thucydides complicit or correct? Like, I think even going back to Herodotus, look at how he hedges his bets when he says, I don't know if this is true, but, you know, and the way that, not just in terms of rhetoric, but in terms of honesty, truth and art,

• 21:13Speaker 01

  all these different voices for over thousands of years. Of course, there's gaps. Of course, people have been left out. I've tried to articulate their experience. Is one of the most valuable things humanity has today are all these voices through a technology of the book that still are here. And my students sometimes will, and my students are great creative writing, MFA students. Again, the idea that it's harmful or wrong or will be bad for you to read somebody else's perspective or point of view from the past, or you should shrug it off because You know, they were a terrible tyrant or what have you. Like, what the canon offers us is a conversation to respond to.

• 21:49Ryan Holiday?

  Yeah.

• 21:50Speaker 01

  And, and I, I think that's what's missing today, you know?

• 21:53Ryan Holiday?

  Well, there's even this sense like that the Greeks and the Romans were all these old, dead white guys, right? And like even in the case of the Stoics, Seneca's born in Spain, right? Epictetus is a slave, Marcus Aurelius is an emperor. That's an incredible swath of diversity, just in those three characters, right? Zeno, some people think he might have been African or had some African blood in him. And, and so you have this actually incredibly diverse group, diverse not just in, in terms of, of race or origin, but also in experience, which is a stand-in for the larger sense of diversity. So it's so closed-minded to say that.

• 22:33Ryan Holiday?

  And then there, of course, like it, it was largely male-centric, but like it, it was only in, when I really studied it, I go,

• 22:43Ryan Holiday?

  Brutus's wife is Cato's daughter. And so, and, and there's this even in the Shakespeare play and in Plutarch, you get this interesting interplay between Brutus and his wife. His wife, we have, we, we make Brutus the main character. But if you were presenting that today, you would show Brutus almost certainly as somewhat cowardly and vacillating. And it's his wife who steals him with courage and sort of puts him to it. And so actually, it's not like, it's not that there weren't women involved. It's just, just in how we've talked about it. And so it is, the canon and our understanding of history and the story can be changed.

• 23:27Ryan Holiday?

  Without even adding anything new, it's just what are you emphasizing and how? Like Plutarch renders Portia Cato as, as a not heroic figure. But you could just as easily reimagine that, which is by the way, what they were doing, that there's a thousand plays about Hercules and a thousand plays about. All the, you know, Oedipus, every generation, they were just rewriting the same, in the same way that we make and remake the Marvel movies. And even just the early Marvel movies versus now, they're more diverse. You know, there's, women have greater roles, they're tackling the issues of the day. That's what the classics were. The problem was we just stopped at some point and we said, this is, it's baked.

• 24:09Ryan Holiday?

  And in fact, it's never been baked and it's always been possible to reimagine and add. And just, it's really an anachronism that we see them all the same, in the same way that we see all white people today as the same. When a generation ago here in America, Italian people didn't feel white. That's why they put up statues of Columbus. They were trying to celebrate one of their guys, you know? Which again, is, it's interesting how that, that experience is literally incomprehensible to us. We can't see, we see Columbus as a racist figure, which, you know, as a figure of colonialism.

• 24:51Ryan Holiday?

  But in 1922, if you're an Italian immigrant, you see representation in Columbus.

• 25:00Speaker 01

  And you could be whiter.

• 25:02Ryan Holiday?

  Yeah.

• 25:02Speaker 01

  If you could identify with Columbus. It was a way to pass within society.

• 25:07Ryan Holiday?

  Or to just be proud of something in yourself.

• 25:09Speaker 01

  Exactly. I know, one thing I try to do in my writing and my perspective, which I'm as guilty as anybody, but we, how do we not map this American moment and its recent history onto all of the conflicts and problems we see in the world now and also in the past? I mean, how do we not bring our idea of power, identity, culture, gender, which we have, we have a different way of talking about it now than we did even 20 years ago, 40 years ago.

• 25:37Speaker 01

  To these moments from 4,000, 2,000, 3,000 years ago. I love the podcast, The Rest Is History, the two British guys that do it. I mean, I just love it because they are able to say, you know, I don't think you understood what was happening, you know, when Nero's first wife died, and then he forced the slave to become a eunuch, you know, that he named after that. So to bring our current perspective on to that, it may be insightful right now, but there's also a logic there that's like a relic been lost to time that we have to work to understand again through the writings that exist and through the engagement we're still offered by, again, the technology of writing.

• 26:10Ryan Holiday?

  Well, these labels and these ideas don't always hold true. So like, I remember in Ron Chernow's biography of Grant, which I'm fascinated by Grant, I've read pretty much everything I've ever written on Grant, and Chernow talks about him repeatedly as an alcoholic, which he may or may not have been, but certainly Grant did not know he was an alcoholic, because that wasn't a thing, right?

• 26:32Speaker 01

  Yes, that's our language now.

• 26:33Ryan Holiday?

  Yeah, and so the conceit is inherently problematic, right? So Grant might be drinking, might not be drinking, but the sense that he is addicted to a thing and he can't stop doing the thing is a modern conception, right? Another, another version of this is there are these students at Brown University every couple of years, they protest this statue of Marcus Aurelius that's on campus, because Marcus Aurelius was an imperialist or a colonizer. And he, literally, literally that is true. That's what Rome was, like the imperial empire. But first off, it's a fundamentally different form of colonization. And second of all, it was 2,000 years ago, right?

• 27:17Ryan Holiday?

  And the idea that you're going to take a label about a thing we're struggling with now and project it backwards is problematic. It doesn't mean that that's not in interest, that there's not interesting. Thinking to be done about how did Rome conceive of its role as an imperial country? And what's fascinating is that they had all the same debates that we had now. The idea was you, an enterprising politician, would get assigned to one of the colonies, which they would proceed to loot, right? But not everyone thought that was fair or a good idea. And there was lots of criticism even of that at the time.

• 28:00Ryan Holiday?

  And so to reduce it as, as this singular thing that everyone was on board with that we now say is bad is to miss actually the more timeless thing that's happening, which is there are sort of good incentives, bad incentives, good actors and bad actors within a society. And society and the way history judges a group depends on how that battle plays out. And in fact, that same battle is playing out now. So to dismiss the Romans as imperialists is,

• 28:32Ryan Holiday?

  I think, academic and somewhat pointless. It's, it's better to go where we like them. Yes. Why did the good guys win or lose? And what lessons can we take from that? In, in, in the same way that we have to like, it's a slightly different discussion with, I think, you know, monuments to Confederates or the lost cause, because that is an ongoing myth that is, that was, those, those were put up to wage a certain kind of intellectual warfare to prop up a system that continues to exist to this day. And there's a difference between that happening in a museum

• 29:13Ryan Holiday?

  as a historical artifact and as a civic monument that you pay to upkeep now. But like, you, you can't, it's, you can't just reduce it as this all one or the other thing. You have to understand what's happening, why it's happening. And, and to not be able to do that is to me the sign of a weak mind and a self-righteous mind that is actually incapable of. Making the world better.

• 29:37Speaker 01

  And it makes me sad because that used to be a starting point. We all got things wrong. We're like, oh, Rome is an imperialist power. It's like, okay, well, now read everything that you can and use your current day lens to come to a new opinion. But that's a way to not have to do that or not have to keep engaging. It's the end of the conversation. Instead of the beginning of a conversation. You know, and I, I see liberal arts education as, you know, spending four years reading other people's perspectives and within fiction or nonfiction or poetry, going into their perspective and seeing the world for however long you're reading as somebody different than yourself. And then you come back out into your perspective and you can't see the world the same way. You know, you expand through um

• 30:18Speaker 01

  looking at the world via these stories that other people have left. And I just always remember, I don't know if it's a conservative and liberal thing, but like at the 2016 convention, I was writing about it. And this is the fear of outside information. Like, we have to remember on both sides, like especially liberal side, the more information you have, the more time you spend seeing through somebody else's mind, whether it's an emperor from 2000 years ago, you know, um, whether it's whoever it is, then coming back to yours, you can do again what I think is the hardest thing. And this isn't just in writing, but in life, to understand or try to see what's necessary from what's not, you know, and I, I just, I think that we're so lucky

• 31:00Speaker 01

  to have had a conversation going on for so long, to have all, you know, like I, I was walking through your bookstore and I saw the Peloponnesian War, you know, one of my favorite books. And I, again, I don't know, I only make two nuclear war jokes a semester. That's my, my limit with my students. But I think I've already reached it. But, you know, in the last 10 years before the president and how we um kind of slant it, that hadn't been as large a conversation nuclear war is in the past. But that conversation between Sparta and Athens and whether to aggressively go on the Athenian part and invade, um, and what could happen, what the consequences could be, still feels as relevant and ever there. And not like a piece or not, but I always think of Syracuse, you know, and sending the fleet to Syracuse.

• 31:43Speaker 01

  And it was so awful that when people came back, the few survivors of the fleet to tell the Athenians what had happened, they wouldn't believe them, that the whole fleet could be gone. They were executed for even saying it.

• 31:53Ryan Holiday?

  Well, when General Mattis was Secretary of Defense, he Assigned the history of the Peloponnesian War as a book for people to read. Because the, what they call it, the Thucydides trap. The idea of an ascendant, a dominant power and an ascendant power. And China and America would maybe talk about which one is ascendant, which one's dominant, which is ironic. But the idea of how these clashes play out. So instead of, you know, obviously the state and the Defense Department have access to the latest cables, latest studies, greatest intelligence. And here they are, reading a 2,500 year old book about a war fought by ships that had oars. You know, to give you a sense of how long ago it was.

• 32:39Ryan Holiday?

  The, the ships would clash and then the men would jump off and fight each other with swords, like as if it was the ground. That's how long ago this was. And yet, the same things are happening.

• 32:50Ryan Holiday?

  I'm just writing about this in the book I'm doing now, the, the, the Melian Dialogue or Melian Dialogue. Like, the most famous passage in the history of the Peloponnesian War is basically Athens going to this little proxy client state and going, might makes right, is the strong do what they can and the weak struggle as they must. Right? As today, we talk about, you know, systemic racism and structural problems and intersection. That is the same discussion, right? It, it's, it's, and, but how many people that throw these buzzwords around could actually connect it to some sort of classical understanding of that, some real insight into human nature

• 33:35Ryan Holiday?

  that goes back far enough that you're not thinking Republican, Democrat, white, black, America, whatever. It's, it's taking it back far enough, you can see what humans do. And how a lot of the systems we developed, the stories we tell, the institutions we build, were designed to counteract those impulses. Yes. Right? Like, the UN being one such invention, right? Or treaties being another invention, or the Geneva Convention. We've, we've invented stuff to deal with things.

• 34:10Ryan Holiday?

  And sometimes we forget the source of that insight or that hard-won lesson. And so to not have that historical basis is just an enormous liability. So people talk about STEM and how we need to learn math, whatever. But if you don't have an understanding of how humans work and how they've always worked, what good is your ability to build really good rockets or whatever?

• 34:33Speaker 01

  I mean, I couldn't agree more. And I, you know, it goes back, like, I guess, to two ways. One is, um, there's such a human element to all of this writing, too. Like, when you, you, you talk about Seneca a lot, like, I'll never forget, um, his Practicing Death essay. You know, when he's talking about, um, is it tuberculosis? He's, he had a really bad attack. He's like, I am practicing death. You know, and reading that the first time, that was, you know, it's a letter, I think. And it's, I read it in Latin and then I read it again in a translation. The Latin's like, having done, you know, with all the participles. But then the translation, John to God, it's a great translation, goes, I am practicing death. You know, and that's the first line as the, as the translation comes off. And so even within, you know, these larger issues, those moments of human, you know,

• 35:17Speaker 01

  suffering and, and perspective, how is that not going to make somebody a better writer today to read that, you know? And, and I guess the second thing is like with Thomson, exactly what you're talking about, these different structures, he understood their inventedness and their fragility.

• 35:32Ryan Holiday?

  Yeah.

• 35:32Speaker 01

  You know, and, and if, if somebody gets enough power, especially in the post-war world with nuclear weapons, where you have to make a decision in five minutes whether to respond, you know, we're dealing with stakes that the human mind can't really, you know, conceptualize. I think that's the Susan Sontag quote is like, we can understand the death of a person. We can't understand the death of a species.

• 35:52Ryan Holiday?

  Yeah.

• 35:52Speaker 01

  You know, of us, of, of humankind.

• 35:55Ryan Holiday?

  Well, I mean, even in the pandemic, it's clear people have real trouble thinking about.

• 36:04Ryan Holiday?

  The effect of their decisions on other people, right? And so, of course, we're going to struggle with bigger, you know, tragedy of the commons issues like the environment or public trust or what, you know, we're, that's going to be, if, if we can't just go, hey, I have this, or I might have this, so I'm going to stay home, or I'm going to get this vaccine, or I'm going to wear this mask, or whatever it is. Or that the, the whole reason that governments exist is to bind people together to solve problems like that.

• 36:41Ryan Holiday?

  Because instant groups of people can't self-organize quickly enough or voluntarily enough, it like, that's what it's all there for. And so if you can't do that, and, and in meditations, Marcus Aurelius is going, there's two types of plagues. There's a plague that can destroy your life and a plague that can destroy your character. He was writing that during the Antonine Plague. He would have understood how these extreme, difficult, disorienting, scary events fuck with people and, and bring out the worst in some people and the best in other people. And, and yet, none of these problems or issues are new. And all of the great literature is about this. I, I forget, I was reading one of the, the Greek players.

• 37:26Ryan Holiday?

  It might have been Euripides, or it might have been Aeschylus. But it's like, I'm reading this play and I go, oh, it's like about somebody getting revenge and then this jury gets set up and you go, oh, this is the invention of juries.

• 37:36Speaker 01

  Yeah, exactly.

• 37:36Ryan Holiday?

  Like, some, somebody came up with that. They were like, hey, somebody gets wronged, they try to get justice by themselves, they end up hurting themselves and other people in the process. So let's come up with a system that solves that. And you're like, this is a play, it's not art, but it's, it's a play designed to try to solve this problem that is clearly fundamental to societies, which is groups of people living together. And that that's what all this stuff is. And it was all invented at some point, didn't like, wasn't given to us, invented it.

• 38:07Speaker 01

  Think then, three, or 2,500 years later, on the night that Martin Luther King is shot, Bobby Kennedy, you know, who was a Philistine for most of his life, but after his very public tragedy, began to read the Greeks, began to read.

• 38:22Ryan Holiday?

  I have the book in the bookstore. He has Edith.

• 38:26Ryan Holiday?

  Edith, what's her name?

• 38:27Speaker 01

  Promen, no, Edith.

• 38:28Ryan Holiday?

  Wharton, I don't know. So is it some Edith something? And she wrote this book called The Greek Way, which is a sample survey course of all the Greek plays. And that's where he gets, what does he say? Drop by drop, we suffer unto truth or something like that?

• 38:43Speaker 01

  He quotes, she admitted like monotheistic, like even in our sleep, you know, pain or suffering, you know, drop by drop comes onto the heart. Until, you know, through the awful grace of God, you know, we arrive at understanding.

• 38:58Ryan Holiday?

  Yes. Basically, we learn through pain and suffering. And he was saying, I've learned through pain and suffering the loss of my brother. You're now mourning Martin Luther King. Rioting, anger, pain, whatever, won't do any, won't solve this. We gotta come together. And then I think the irony then, you know, 50 years later, his son is clearly motivated by some profound grievance. And maybe he got kicked in the head by a horse or something. But, you know, like something, something broke inside that person. And he is now a vehicle for a more modern version of those same things, which is now you don't have to, a group doesn't have to get together and burn down buildings and whatever.

• 39:39Ryan Holiday?

  You can just spread like a virus, bad destructive ideas that tear at the fabric of society and, and what underpins the modern health system, and it's just as destructive.

• 39:52Speaker 01

  And there's a great book on immunity by Yulie Biss. And it was the first time reading it, she's a nonfiction writer. It was the first time I began to understand. She articulated that immunity is not about you. You know, it's about how the participation. And she had been writing it while she was pregnant in the 2010s. You know, and she'd, a great writer had gone to Iowa. And it was the first time I stepped back and realized like those systems you talk about, it's about your participation in them, not to protect you, but so all of us can come together and get a different outcome than we used to get individually.

• 40:25Ryan Holiday?

  We have this understanding of America being about liberty, which it is. But there's liberty and then there's responsibility. And they were seen, the idea was government would create liberty and then philosophy and culture would create virtue. And these two things have to coexist or operate together for the package to work.

• 40:53Ryan Holiday?

  Washington orders the vaccination of his troops against smallpox when like one in four people died from the vaccine, like when it was so, but, but it's, they're, they're just even in that early moment wrestling with individual versus collective and how do these things come together. And so again, when you can read about the ethics of this issue 300 years ago, it helps inform how you think about it now. There's this super moving thing that Benjamin Franklin writes about his decision not to vaccinate his son and he dies and it tears apart his marriage and his life, not to get on a vaccine tangent, but the, the point is almost none of the issues are new. They're struggling, we're

• 41:38Ryan Holiday?

  struggling with them in the same way, just the names and dates and places and characters, they change, but the, the problems stay the same, you know, and, and that's, that's just kind of what's always been happening.

• 41:52Speaker 01

  And I, you, you've written about this a lot too, but you talked about it a little bit just now, where bad information, really virulent information is like a virus. And this goes back to antisemitism, the elders of Zion. It's a way of thinking, you know, that actually infects the way the rest of your mind thinks. There's a great book, Wasteland, about Ezra Pound and T S Eliot that came out recently as a biography of the poem, The Wasteland. And you just saw Ezra Pound's mind deteriorating with like, not syphilis, but antisemitic conspiracy theories.

• 42:25Ryan Holiday?

  It's, it is really interesting, like the way, I was talking to someone about this recently, I was saying that antisemitism may be the oldest virus. Like, and it's this thing that's in, I mean, it infects the Romans, different emperors at different times, different leaders at different times. And, and then you have these different tropes or different, like that the elders of the protocol of not Zion, or what's it called? It's not that old, right?

• 42:48Speaker 01

  No.

• 42:49Ryan Holiday?

  And

• 42:49Speaker 01

  And it's like Russian propaganda.

• 42:51Ryan Holiday?

  Yeah, it's just this thing, this horrible thing that someone puts out in the world and then it, it can't be eradicated. And, and you can be immunized against it with information and understanding, but it's just going around affecting, but if you lack the firewalls for it, it can, my metaphors are getting very mixed here, but if you lack the different, you know, some, it can go big or small. And yeah, there, there are these certain viruses and I've, I've watched it. I've watched it happen with people I know, even people who are fans of mine where it's like, you can kind of see it, like, you know, okay, you know, like you follow people on Instagram, and then it's like, oh, I haven't seen a picture of their spouse in a while. And then, then it's like announcing they're separated, and then announcing that.

• 43:36Ryan Holiday?

  You kind of sensed, you're like, oh, you kind of keep this mental tab, like, you know where they are in that transition, right? And you kind of go, okay, they just retweeted something from Elon Musk. And then, you know, now they're talking about trans women in sports. And you kind of watch this, it's like this evolution. You know, the metaphor they use is about taking the red pill, but it's actually not a thing, and you get it. You don't actually, there's this latency period where it's kind of working on you, and you don't understand it, and maybe it was escapable, maybe it wasn't.

• 44:17Ryan Holiday?

  But I'm very fascinated with the way that, yeah, these kind of idea viruses get into a person and how they, how they change. I mean, Elon Musk is, on the one hand, antisemitism goes way back to his grandfather, who fled to South Africa precisely because he was an antisemite and thought there should be like, an apartheid regime in South Africa. Like, he didn't go there and there was apartheid. He was like, this is, this is our chance, you know? So there's this predisposition towards it, clearly, in that family. And then you kind of watch, like, towards conspiratorial thinking, right?

• 45:01Ryan Holiday?

  And then you watch as his information diet changes and his place in the world changes. And then maybe he gets criticized here or there. And then all of a sudden, who he was five years ago. I read the first bio, the Ashley Vance bio of Elon Musk, and then I read that Walter Asner. It's the same person, but it's not the same person. He's been fundamentally changed and remade by the information that he's consumed.

• 45:25Speaker 01

  It's terrifying too, because you would talk about it, imagine as immunity or a set system and then it comes through. I think of Steve Bannon, like, I'll go to CPAC and write about what's going on there. And this year, I saw him at his private party, and I know he's read everything, but I know it's not an immunity to the conspiracies. But I asked him, I was, you know, everybody's there, they want to be him, which is very strange. That's like the podcasters, like, how do I do my podcast? How do I be a Steve Bannon? So I was, you know, what's your favorite George Orwell? Because I know he's talked about it. And he said Homage to Catalonia. I'm like, that's my favorite George Orwell. But, but you then realize that may have been it a long time ago. Now he's mapping a completely different narrative onto that, that even exists now with some of it there. And so if that was

• 46:09Speaker 01

  part of his immunity, or anybody's immunity, is reading other people's perspectives, what happens when the virus goes so far, that now every pre-existing thing can just be, like, taken apart piecemeal to prove what you already feel or believe. And that was kind of terrifying to me.

• 46:23Ryan Holiday?

  Or you could have this almost kind of schizophrenic, where you, you, you know all this stuff, but that gets in the way of what you want to do. Like, you're not even seeing yourself as the person who's doing what you're, you know what I mean? Like, you're doing, you're, you can't, what's that question? Are we the baddies? You know, like, you can't even ask that question anymore, because something has happened, or your self-interest is dependent on you kind of not understanding. It's a, it's a weird, but the idea that, yeah, this is, this is what happens to Catalina. You know what I mean? Like, 20, 200 years ago, or 2100 years ago, whatever it is, this guy, you know, he's probably has these dinner parties, and they go, you'd be way better, man, you know? And he grew up with his parents

• 47:06Ryan Holiday?

  telling him how great he was. And then he goes, well, I bet I could, you know, he's just looking at it in pieces on the chessboard and not going... Am I burning this whole thing down just for me, you know?

• 47:19Speaker 01

  I, I, I just think it's, it's tough when we, um, you know, it gets back to part of our censorship talks too. Like I teach Shooting an Elephant Today, you know, by George Orwell. I, I love homage to Catalonia. I, there's parts of it where he's talking about what Orwell's talking about what it was like as a colonial administrator and how he knew colonialism was wrong, but it's a lot like Thompson. He was caught up in enforcing it. So he shows how it destroys him.

• 47:43Ryan Holiday?

  Sure.

• 47:44Speaker 01

  As a way to argue against it, which Thompson does a very good job of too. But, you know, the talk of editing parts of Orwell now.

• 47:50Ryan Holiday?

  Right.

• 47:51Speaker 01

  You know, instead of dealing with some of the, you know, like language that he has in it, to me is, is mind blowing. Like within our present and just scrambles that goodie or baddie argument immediately.

• 48:01Ryan Holiday?

  Yeah.

• 48:01Speaker 01

  You know, and, and it's to me really dangerous because it's like the example you give with Roosevelt. It's tinkering with, um, something so essential, information that is essential to us. Like, you know, his perspective. So I don't know, you know, I think about our, our current media situation. I, it freaks me out a lot when, and this gets back to the canon and banned books. It freaks me out a lot when we're going beyond our online, like fights with each other. And there's the idea that because our lens is the latest and the most important.

• 48:30Ryan Holiday?

  Yeah.

• 48:30Speaker 01

  We now can begin to take out certain passages of Orwell.

• 48:33Ryan Holiday?

  Sure.

• 48:33Speaker 01

  Or edit them. And I mean, I, I, I don't think that's anyway inherent to the present. But I do think so much is magnified right now by the way that we wake up in the morning and become accustomed to communicating with our phones or with everybody else.

• 48:47Ryan Holiday?

  Yes. I, I, I noticed this the other day. So I was reading my kids, uh, I was telling them the story of the Odyssey. And, uh, you know, I told them the story of, um, Cyclops and forgetting his name, but, uh, you know, Odysseus says, you know. What's his name?

• 49:02Speaker 01

  Is it Polyphemus?

• 49:02Ryan Holiday?

  Yeah, Polyphemus. Uh, you know, he says, what's your name? And he says, no man. And then so they go, hey, who poked out my eyes? No man, no, no man picked out my, and my kids just lose their mind. Like this is the funniest joke. And now they do, they do all this, anytime they do anything wrong, you know, I go like, who punched your brother? And they go, no man punched my brother. You know, like they're, they're just, they're just playing with this language in a way that someone almost 3,000 years ago or more. Was playing with language is incredible, right? And so we could be celebrating the sort of timelessness and and the the uniquely humanness of all of that. And so there's there, yeah, there are these things that sort of ring true and good.

• 49:40Ryan Holiday?

  And then there's the same kind of dark urges that tyrants and dictators and populists and demagogues have also been playing up. And you have to understand both of those, right? What makes Lincoln so great is his understanding of biblical language and story, right? This king draws on the same ideas. And then, yeah, what what people are throwing out today, of course, it's not going to resonate. Like, you're not draw, you don't have the, you don't have the underlying understanding or information to make this more than what it is.

• 50:19Ryan Holiday?

  And to really speak to that part of people that you have to bring out to get them to do things. It's, yeah, it's like, it's exactly what Hunter S. Thompson is saying, that just like, our energy will prevail alone, or the righteousness of our cause will prevail alone. And it's so much, so much more than that.

• 50:38Speaker 01

  Yeah, I mean, I, I think of when I was like, again, 18, my whole Latin class Jesuit high school bellman in California was the first six books of the Aeneid. And so translating that, and I'll never forget, there's a passage where, you know, Virgil's writing, and there's a lot of different backgrounds of what's going on. But in the epic poem, you know, and someday Rome won't exist anymore either, and stepping back, it's, it's a fact, there'll be a day, America does not exist, but being an 18 year old boy with my boy brain, and sitting back and looking around and being like, this country's not going to exist someday, too.

• 51:11Ryan Holiday?

  Sure.

• 51:12Speaker 01

  You know, and having that realization, the presentness of our lives, the instantaneousness of our lives, it doesn't just make us, you know, focused on our phones or screens or who said something. It makes us blind in the way humans want to be to very clear facts that this country, these people were all gonna die someday anyways, as the Stoics will tell you, they're already dead. But you know better than anybody, but this country itself, just in the way Romans is gonna be gone. And whatever an eighteen year old boy's brain is, it is malleable. You can give it good writing and good perspectives. And those magnets, they're not gonna hurt, you know? And so I've always remembered that moment of looking up and stepping back from the book.

• 51:51Ryan Holiday?

  When to think, why is Virgil putting it in there? He's writing to Augustus, right? And he's trying to get that to him. And so like the, just even the, it's heightened by the sense of like, what's the author trying to do here? What's the message that they're delivering, right? To see Meditations as a book being written in a plague, right? Or to see, you know, I think it's Euripides is writing as a veteran of this horrible war and trying to process the trauma of what he went through. You know, Seneca's plays being his inability to outwardly criticize Nero and the regime and having to sublimate it in fiction.

• 52:32Ryan Holiday?

  Shakespeare basically makes one overt mention of current day issues, and it basically nearly ends his life. And so the rest of Shakespeare is all about Greece and Rome and things hundreds of years in the past, because that's the only way he can speak to it. The benefit, though, is that it also speaks to us and it disarms, it gets underneath our resistance to you, who are you to tell me about this or that? And so to understand, yeah, that's what art is supposed to do, is to touch us in these places. And when you, yeah, when you're banning it because it's politically incorrect or not diverse enough or whatever, you're missing actually what it is,

• 53:16Ryan Holiday?

  the truth of how representative it is, and the fact that the point is that there really is only one human experience.

• 53:27Speaker 01

  I did a political writing class. I teach graduate students, but this was undergraduates during the pandemic. So we read a lot of Thompson. We read a lot of Didion. We read James Baldwin. We read, you know, a lot of different writers from the 20th century. And what I wanted my students to see was look at how they're doing exactly what you said.

• 53:45Ryan Holiday?

  Yeah.

• 53:45Speaker 01

  Even in these really like political instances at a convention, taking and dramatizing the moment so the reader can do the work to come and arrive at their own conclusion. An op ed is the opposite of art, you know, and an op ed is the answer, you know, I love the line from Claudia Rankine, Claudia Rankine quotes it, but you know, you know, art are the questions like we arrive at after we've gone through all the answers.

• 54:12Ryan Holiday?

  Yeah.

• 54:13Speaker 01

  You know, and like, I'm probably mangling, but this idea that in that class, they needed to dramatize or write a story about maybe something political in Washington DC. And these, I don't usually teach undergrad, they were undergraduates, all op eds.

• 54:26Ryan Holiday?

  Yeah.

• 54:27Speaker 01

  And I'd be like, well, where did you see this kind of writing earlier in our examples? They'd be like, well, John Didion says we tell ourselves stories in order to live.

• 54:33Ryan Holiday?

  Yeah.

• 54:33Speaker 01

  So I'm like, did you miss the rest of that essay? That's all dramatized to make the reader do work.

• 54:37Ryan Holiday?

  Yeah.

• 54:38Speaker 01

  To engage it the same way Shakespeare had to move around something and tell that story in a different way and say how, you know, I think through my scene is like Virgil had to reach somehow. He had to reach Augustus.

• 54:49Ryan Holiday?

  Yes.

• 54:49Speaker 01

  And if he just told Augustus in op ed fashion.

• 54:51Ryan Holiday?

  These are your exile or worse.

• 54:53Speaker 01

  Yes, or worse. You're exactly right. And I, I think, I think a lot of students want to arrive at op eds now as, as somehow the purest form of the expression they want. Or that's the starting place, maybe to figure out what you think or feel. And now put the messiness of humanity and the world around you into a story that might articulate it where the reader can do work and not just be given an answer.

• 55:12Ryan Holiday?

  Yeah, to, to think that it's, it's harder to do, but it ultimately reaches more people because the defenses are down. Hunter S. Thompson is writing Fear and Loving in Las Vegas, not about drugs, but about the American dream. That to me, Hells Angels is captured by the quote, he says, myths and legends die hard in America because they prove to us that the tyranny of the rat race is not yet final. It's a, it's a, the Hells Angels were a revolt against the corporatization and the.

• 55:46Ryan Holiday?

  You know, the buzz cut, you know, buttoned down sort of world that had come out of the Second World War. But Thompson is basically, Thompson isn't celebrating them. He's saying that the cure is maybe worse than the disease. These are, he shows them, you know, doing a gang rape, right? I think there's all this criticism now about the new Michael Lewis book about Sam Bankman-Fried. It's like, he fillets this dude. He presents, there's a quote in the book where he goes, "I don't think I have a soul." Right? You know, like Lewis's job as the journalist is to present the story as it happens. If he's going, "This dude sucks. Fuck this dude," you don't read the book.

• 56:30Ryan Holiday?

  It's the work of the book is how do you get someone to read from start to finish about an unlikable person? And capture attention along the way? And like, it's funny with my stuff on ancient philosophy, you know, people go, "Oh, this is just self-help." And I go, "Yes, that's the point." Like, if writing about ancient philosophy was enough to get people to read ancient philosophy, I wouldn't have to do it. Like, the ancient philosophers did ancient philosophy. The problem is, we now exist in a world where the vast majority of people can't read ancient philosophy or have no interest in ancient philosophy. So by taking self-help, which people pick up when they walk through the airport

• 57:14Ryan Holiday?

  or somebody buys for someone who's going through something, and I use it as an entry point into ancient philosophy, I'm doing that, precisely that kind of jujitsu. And people, people don't like that because they want to speak only to people like them, which is this sort of 1% sliver who really likes the original stuff or could, could take the full factual breakdown. And that's not where most people are, and that's not where opinions are changed and worlds are opened up. It's, it's much more, like, if you just wrote a book about Richard Nixon, for instance, and corrupt politics in the middle of the 20th century, you know, that's going to sell less copies than doing that through a lens of Hunter S. Thompson, who has a different reputation, right?

• 57:57Ryan Holiday?

  And, and so that, the art of it is, is they think you're doing one thing, and really you're doing another thing. And that's what- The ancients were doing too.

• 58:06Speaker 01

  Yeah, and I don't know why we don't think that to make art, they were dealing with the same wagers.

• 58:12Ryan Holiday?

  Yes.

• 58:12Speaker 01

  And stakes.

• 58:13Ryan Holiday?

  Yeah.

• 58:13Speaker 01

  You know, when at every move even more so than we are and, you know, and had to not just like that idea of, you know, getting the reader to do work or that metaphor of Jiu Jitsu, you're exactly right. But that, you know, if they made one more mention than they did.

• 58:32Ryan Holiday?

  Yeah.

• 58:33Speaker 01

  Their lives are over.

• 58:34Ryan Holiday?

  Yeah.

• 58:34Speaker 01

  You know, that they're, they're no longer, and we've talked a lot in the 20th, 21st century about this in a kind of global way. But I, it always blows my mind that the historical conversation, or when we talk about it in a historical sense, that gets left off.

• 58:47Ryan Holiday?

  Well, yeah, it's like, there's two forms of death. One, like you are too on the nose and the emperor cuts off your head. The other, you're too on the nose, you're too lechery, you're too boring, you're too factual. And the reader cuts off your head.

• 59:01Speaker 01

  Yeah.

• 59:01Ryan Holiday?

  Cause they say, I don't want to read this anymore. And you think Plutarch is going, you think you want to read about Alexander the Great because you think he's a hero. Let me present to you why he was great in many ways, but ultimately a tragic case. And maybe you totally missed the point. You're Napoleon, you read it and you're like, fuck, I love Alexander the Great. But if you're somebody who can be persuaded, you're seeing the more nuanced picture. This is why he's, he, he writes parallel lives. So it's, it's Cato and Caesar, how they're contrasting with each other, right? And he's, he's comparing them without saying who's better, but it's obvious who's better, right? And, and you have the artfulness of having to persuade the audience who will kill you if you're boring.

• 59:46Ryan Holiday?

  And then speak truth to power without threatening truth to power. This is also, Machiavelli is the most tragic example of this. Machiavelli is writing a book to the people who tortured him. Like Machiavellian is a Republican in the sense that he did not think there should be a prince. And he's having to write about how princes get power. As a historian, he's writing about this and he's having to find a way to both say, this is how it works. But also this probably isn't how it should work without tipping off the people who have already.

• 1:00:27Ryan Holiday?

  Tied him to the rack and spun him around, you know? And, and the, the subtlety to which he's doing it. And then today we're like, oh, that's very Machiavellian. Like, dude, th- this dude was threading a fucking needle with his life on the line. And you're missing the way that this can both be, be read from both perspectives and has this kind of dual lesson in it. And I think Hunter S. Thompson is doing that in his own way. It's fun and ridiculous and excess. And it's also this profound sadness and indictment ultimately of the same culture. It's just the tragedy of he gets hooked on the stuff and he can't get out.

• 1:01:08Speaker 01

  His son, his son wrote a great book called Stories I Tell Myself, one Thompson. And so I tried to end with Nixon leaving, but those years after are really tough because it's the way we understand alcoholism now, coupled with how Thompson would take Dexedrine.

• 1:01:24Ryan Holiday?

  Yeah.

• 1:01:24Speaker 01

  And there was a price to be paid later.

• 1:01:26Ryan Holiday?

  Yeah.

• 1:01:26Speaker 01

  And his son writes about getting hooked on the stuff. I mean, he was drinking a seven hundred and fifty, a seven hundred and fifty milliliter bottle of Jack Daniels.

• 1:01:34Ryan Holiday?

  Yeah.

• 1:01:34Speaker 01

  Every day, starting when he woke up. And it just dissolved him from the inside out in his mind, too.

• 1:01:39Ryan Holiday?

  Yeah.

• 1:01:40Speaker 01

  You know, and so you're right, like that's, he, he is seen in this kind of extreme way and he would present himself that way. But eventually it became, um, he became the caricature.

• 1:01:50Ryan Holiday?

  Yeah.

• 1:01:50Speaker 01

  He would promote, you know, and that happened later. And it wasn't through tons of acid or drug, which are, you know, whatever, but it was, it was just through alcoholism, you know? And it was eventually, you know, speed and cocaine and all these different things, but he was just dissolving his body with that. And I, I, I think that that, that gets lost. Um, and I think one of the hardest questions is how much do you internalize in both your writing and your sensitivity, you know, that tumults around you?

• 1:02:17Ryan Holiday?

  Yeah.

• 1:02:18Speaker 01

  You know, like think of Didion, like having her panic attacks and, you know, passing out and going into a psychiatric treatment, um, facility in the summer of 1968. And her great line is, In retrospect, I don't think nausea, you know, or, um, you know, bouts of dizziness were entirely the wrong reaction to the summer of nineteen sixty-eight. And the same with Thompson, you know, how much do you internalize that tumult and danger around you? Um, and, and what's the line where then that becomes too much? You're not been able to express your perspective on it because of your proximity or sensitivity to it.

• 1:02:49Ryan Holiday?

  Yeah, the toxicity of the people he's around, he absorbs it, he doesn't have a a mechanism for filtering it and processing it, it kind of turns against him himself.

• 1:03:00Speaker 01

  And he just runs, he burned very brightly. I mean, James Salter's a fascinating comparison because Salter wrote until he was eighty-five, eighty-six, ninety, was still writing his next book when he, when he passed away. Um, and, and Thompson, you know, from what I've seen, there were still brilliant pieces later, never really wrote in the same way as he did.

• 1:03:19Ryan Holiday?

  Yeah.

• 1:03:19Speaker 01

  When he was younger and healthier.

• 1:03:20Ryan Holiday?

  No, there's a F. Scott Fitzgeraldness to it.

• 1:03:23Speaker 01

  Yeah.

• 1:03:23Ryan Holiday?

  Well, I think with Dorothy Parker looked at his corpse and just said, you poor son of a bitch. You know, and that's like, that's Turner's Thompson.

• 1:03:29Speaker 01

  It is, you know, except there's a kind of terrifying sense of doom that imagine if Fitzgerald lived those next thirty years with that kind of

• 1:03:37Ryan Holiday?

  But as a shell of a person, like, like he didn't successfully kill himself earlier, which is what Fitzgerald did.

• 1:03:43Speaker 01

  Yes, you know, with alcohol, exactly right. And I, you know, I think art doesn't have to be seen as self-destructive.

• 1:03:51Ryan Holiday?

  Yeah.

• 1:03:52Speaker 01

  But to think that somehow, and again, this goes back to baseball, I would think of Barry Bonds, a player I enjoyed watching growing up. You know, and he was very difficult with the media, he was very guarded. To think that his success, his incredible ability, and then also love the issues with Stereot, to think that his uniqueness is somehow separate from his personality. And who he is, is mind blowing and the way we often separate writers from their work. I mean, it's been a conversation that's going on a long time. I think it's just another form of reduction that we have now, you know, and Thompson was, he wasn't a good writer because he was an alcoholic, but there was a terrible, terrible wager going on.

• 1:04:30Ryan Holiday?

  Yeah.

• 1:04:30Speaker 01

  That he didn't even know what side he was coming down on, you know, and, and I, there's no one right answer to it. It's, I find it to be, you know, that it gets back to that. I quoted it earlier, but that line from Conrad, it's like, "Life is short, art is long, and success is really far off." That's not a good thing.

• 1:04:49Ryan Holiday?

  No, no, no.

• 1:04:51Speaker 01

  It's not heartening, you know? It's like, oh, my book will eventually be written. It's like, no, there are a lot of things that could go wrong at any moment. And I, you know, how could somebody's athletic brilliance be separate from the way they see the world? You know, and especially the wager Barry Bonds made then to-

• 1:05:07Ryan Holiday?

  Yeah, of course, they're gonna do anything it takes to be able to express that.

• 1:05:10Speaker 01

  Yeah.

• 1:05:11Ryan Holiday?

  It's like almost a form of like body dysmorphia, where it's like, I have this thing that has to get out. The world has to see me the way I see myself. And I'll turn myself into whatever kind of art monster I have to be to be able to do it.

• 1:05:26Speaker 01

  Or a steroid monster.

• 1:05:27Ryan Holiday?

  Right.

• 1:05:27Speaker 01

  You know, and it's, it's, it's, and then there's the moral argument too, where it's like, Mark McGuire wasn't a better hitter than Barry Bonds, but on steroids, he was succeeding more. Why should that person be able to do it when I'm the one who has more talent?

• 1:05:40Ryan Holiday?

  Yeah, sure.

• 1:05:40Speaker 01

  And I'm not rising, you know, going up to that level.

• 1:05:43Ryan Holiday?

  Well, this was awesome. I love the book and thanks so much for doing this.

• 1:05:46Speaker 01

  I really enjoyed talking.

• 1:05:58Ryan 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.