The Art and Obsession of Writing with Rich Cohen

After more than a dozen books and decades writing for publications like Vanity Fair and Rolling Stone, Rich Cohen knows how a great story can change the way we see both the past and ourselves. In today’s episode, Rich and Ryan trade stories about the books and writers that shaped them, the ambition behind creative work, how discarded material influences a finished book, the myths that can take over a writer’s life, and more. Rich Cohen is a bestselling author, journalist, and screenwriter. His writing has appeared in The New Yorker, The Atlantic, Harper’s Magazine, Rolling Stone, Vanity Fair, and The Wall Street Journal. He is also the co-creator, with Martin Scorsese, Mick Jagger, and Terence Winter, of the HBO series Vinyl. 👉 Follow Rich Cohen on Instagram:https://www.instagram.com/author.richcohen/?hl=en 📚Grab signed copies of Rich Cohen’s books at The Painted Porch: https://www.thepaintedporch.com/search?type=product&q=rich+cohen* https://www.thepaintedporch.com/search?type=product&q=rich+cohen Murder in the Dollhouse: The Jennifer Dulos Story https://www.thepaintedporch.com/products/murder-in-the-dollhouse-the-jennifer-dulos-story-signed?_pos=1&_sid=c4cdd41b4&_ss=r: https://www.thepaintedporch.com/products/murder-in-the-dollhouse-the-jennifer-dulos-story-signed?_pos=1&_sid=c4cdd41b4&_ss=r https://www.thepaintedporch.com/products/murder-in-the-dollhouse-the-jennifer-dulos-story-signed?_pos=1&_sid=c4cdd41b4&_ss=r Monsters: The 1985 Chicago Bears and the Wild Heart of Football: https://www.thepaintedporch.com/products/monsters-the-1985-chicago-bears-and-the-wild-heart-of-football-signed?_pos=5&_sid=c4cdd41b4&_ss=r https://www.thepaintedporch.com/products/monsters-the-1985-chicago-bears-and-the-wild-heart-of-football-signed?_pos=5&_sid=c4cdd41b4&_ss=r https://www.thepaintedporch.com/products/monsters-the-1985-chicago-bears-and-the-wild-heart-of-football-signed?_pos=5&_sid=c4cdd41b4&_ss=r The Fish That Ate the Whale https://www.thepaintedporch.com/products/fish-that-ate-the-whale-the-life-and-times-of-americas-banana-king-signed?_pos=3&_sid=c4cdd41b4&_ss=r: https://www.thepaintedporch.com/products/fish-that-ate-the-whale-the-life-and-times-of-americas-banana-king-signed?_pos=3&_sid=c4cdd41b4&_ss=r https://www.thepaintedporch.com/products/fish-that-ate-the-whale-the-life-and-times-of-americas-banana-king-signed?_pos=3&_sid=c4cdd41b4&_ss=r Pee Wees: Confessions of a Hockey Parent: https://www.thepaintedporch.com/products/pee-wees-confessions-of-a-hockey-parent-signed?_pos=4&_sid=c4cdd41b4&_ss=r https://www.thepaintedporch.com/products/pee-wees-confessions-of-a-hockey-parent-signed?_pos=4&_sid=c4cdd41b4&_ss=r 📕 Pick up a copy of The Moviegoer by Walker Percy https://www.thepaintedporch.com/products/moviegoer?_pos=1&_sid=bbe80a52c&_ss=r: https://www.thepaintedporch.com/products/moviegoer?_pos=1&_sid=bbe80a52c&_ss=r https://www.thepaintedporch.com/products/moviegoer?_pos=1&_sid=bbe80a52c&_ss=r 🎟️https://www.dailystoiclive.com/DAILY STOIC LIVE https://www.dailystoiclive.com/| Ryan Holiday is coming to a city near you https://www.dailystoiclive.com/! Grab tickets here https://www.dailystoiclive.com/ | https://www.dailystoiclive.com/ 🎙️AD-FREE https://dailystoic.supercast.com/| Support the podcast and go deeper into Stoicism by subscribing toThe Daily Stoic Premium https://dailystoic.supercast.com/ - unlock ad-free listening, early access, and bonus content:https://dailystoic.supercast.com/ ✉️ FREE STOIC WISDOM https://dailystoic.com/dailyemail | Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email athttps://dailystoic.com/dailyemail -- Stop online threats before they become real-world attacks. Visit ironwall.com/DAILYSTOIC and request a free Risk Assessment to see exactly how exposed your executives are. Hosted on Acast. See acast.com/privacy https://acast.com/privacy for more information.

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

• 0:00Ryan Holiday?

  We were looking to spruce up our, our front porch. The weather's finally getting better and we wanted to spend some time hanging out outside with the kids. So we got these awesome hammocks and we actually got them from today's sponsor, Wayfair. If you drove by our, our house, you'd see us out there with our kids reading. We've got this new kitten all hanging out in the hammocks. It's been awesome. And that's because on Wayfair, you'll find quality materials that stand up to real life. They sell furniture and decor that's built to last. And when you shop with Wayfair verified, it's your shortcut to durable pieces that are hand vetted by product specialists using their 10-point quality inspection. They've got thousands of products at every style and budget, whether you're simply replacing an appliance or transforming your home from top to bottom this holiday season.

• 0:42Ryan Holiday?

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• 1:04Speaker 01

  Wayfair, every style, every home.

• 1:06Speaker 02

  One of the reasons people think that they're not introspective people in the past is because it's hard to accept the reality of somebody that's not alive right now. It's just very hard to make them anything but kind of a character in your mind and not real. Most of the people in the past thought that they were doing the right thing.

• 1:22Ryan Holiday?

  Yes.

• 1:23Speaker 02

  So in order to judge them, it's not just that you're having more information and everything, you have to believe that you are doing the right thing right now.

• 1:31Ryan Holiday?

  Rich is one of my favorite writers, so I was honored to have him on the show. He has just brought to life things that I didn't know about, things that I didn't know I wanted. He had this book called Tough Jews that I love. His father is fascinating, who we wrote a book about called The Adventures of Herbie Cohen, who wrote that book about negotiation. He wrote a book about youth hockey. He wrote a book about the Rolling Stones. He wrote a book about the Jewish resistance in World War II. He created this show with Martin Scorsese and Mick Jagger called Vinyl on HBO. That's also incredible. I guess what I'm saying is this is one of my favorite authors. I've gotten so many stories from his books. I've learned so much from his books and I just loved this conversation. We dove into history and memory and writing and parenting and sports and grief. Great conversation.

• 2:16Ryan Holiday?

  I think you're really going to like it. Let's get into it.

• 2:24Ryan Holiday?

  So I was thinking about a conversation you and I had like 10 years ago when I was working on Obstacle. I'd just read The Fish That Ate The Whale. But we were talking about Zemurray, who is a fascinating figure. And you said something that I've been thinking about, which is like, you thought that he thought he would be appreciated by future generations.

• 2:45Speaker 02

  Yeah.

• 2:45Ryan Holiday?

  Like, like they all thought history would judge them kindly or the future would be grateful to them. And of course, the exact opposite.

• 2:54Speaker 02

  Right.

• 2:54Ryan Holiday?

  Is true. How do you think about that?

• 2:58Speaker 02

  I think that the people that try to stretch themselves and go further than their time warrants, or that it's typical for their time, then get blamed a lot of times because they're the ones we remember.

• 3:09Ryan Holiday?

  Yeah.

• 3:10Speaker 02

  So out of the millions and millions and millions and millions of people that lived in the past, there's only a couple of names that survive.

• 3:15Ryan Holiday?

  Right.

• 3:16Speaker 02

  And a lot of times, you know, you'll, you'll find people that get blamed for even their very awkward reaching across lines that people haven't reached across. They left a record and they get blamed for their prejudices and for being stuck in their time. I think that Zemurray basically entered, if you think about it, there was a football game going on and he entered the game. He didn't really think about the rules of the game, if the game was moral or immoral. He just was trying to compete in the game.

• 3:42Ryan Holiday?

  Yeah.

• 3:42Speaker 02

  The irony is that he started his own company that competed with United Fruit and was a much better company, a more moral, a cleaner company. But because of his success, he was ultimately forced to merge with United Fruit. And then he took on the legacy of this other company, which really wasn't his legacy.

• 3:59Ryan Holiday?

  Yeah.

• 3:59Speaker 02

  And that company itself has its own interesting past, which is more complicated. Everywhere you look, it's more complicated than you think, you know?

• 4:06Ryan Holiday?

  But have you seen that clip, what, you know, Mark Andreessen is, the venture capitalist? That is a clip, he's on a podcast and then they're talking about introspection. Seen this? The guy's like, you know, I've read all these biographies. None of the figures were introspective in any way. And Mark Andreessen, obviously a very successful, sort of larger than life figure goes, I'm not introspective at all. I don't, I never look inward. I never look back. I only look forward. And they're sort of, I think what they're trying to make the argument of, and it's not historically without basis, which is that like to be a great success, to be a world mover, to do huge things, you can't get caught up in these niceties about thinking about other people, thinking about moral questions.

• 4:49Ryan Holiday?

  Like, I think they're trying to say that today's generation is too conscientious and deliberative and not sort of bold and swaggering and ambitious enough. I'm not sure that's true, but it's an interesting argument that someone like Zemurray falls right in the middle of, because he didn't strike me as a particularly introspective figure.

• 5:09Speaker 02

  Well, the thing about introspection is it leaves no evidence.

• 5:12Ryan Holiday?

  Yes.

• 5:12Speaker 02

  You know what I mean? So you're judging based on what somebody did, not what they, what they're thinking, which is a problem you always run into with nonfiction, which is I really don't really know what this person was thinking. There's no way to know. So you look for little hints of introspection. So the amount of charity Zemurray did, he set up this free school in South America. He's, he did, that shows a level of introspection. Plus, I think he saw himself one way.

• 5:36Ryan Holiday?

  Yeah.

• 5:36Speaker 02

  You know, he was a member kind of of FDR's cabinet and all this stuff. And he saw himself as kind of with the good guys. And the values, he lived long enough that the values all changed. And all the things he did were suddenly judged not so good. So I think of him like a guy that's holding a hand of cards all night. And suddenly at dawn, all the cards change meaning. Suddenly the aces and the jacks are now like the twos and the threes, and the twos and the threes are like the aces and jacks. And it all turned around on him at the very end of his life and it confused him. But one thing about people today and their, this is what always drives me nuts, which is most of the people in the past thought that they were doing the right thing.

• 6:15Ryan Holiday?

  Yeah.

• 6:15Speaker 02

  So in order to judge them, it's not just that you're having more information and everything, you have to believe that you are doing the right thing right now. You have to believe that what you're doing, the things you're not even thinking of, won't be judged very harshly in 30 or 40 years by your grandkids. And the fact is, we don't, you try your best, but you don't really know how you're going to be judged. And it takes an incredible lack of humility and a sense of certainty to judge people about their actions, a lot of people about their actions in the past, who were born into a particular time, lived in that particular time. And if they're lucky and they lived a long time, you know, lived long enough to see that some of the things they thought were good, were not going to look good in the long run.

• 6:56Ryan Holiday?

  Do you really think they were always doing their best though? Like, I was just really, this fascinating essay about Thomas Jefferson. And, you know, obviously Thomas Jefferson says all this world shattering and changing ideas about how we're all created equal and he condemns slavery and he understands the sort of moral rot of it. But they're sort of looking at some of the things that have been omitted from the history that actually was much more involved in running these slave plantations than people thought. And that, that the sort of big breakthrough for him, the pivot point and the change of his views, the essay is arguing, is when he starts to calculate the rate of return on the birth of new slaves.

• 7:29Speaker 02

  Uh huh.

• 7:29Ryan Holiday?

  And that, that this becomes, it's like the Upton Sinclair thing. It becomes very hard to, to understand something that your salary depends on you not understanding. It's like, he basically goes, he thinks slavery as this dying institution, this financially sort of inefficient industry. But then he starts to realize, oh, I'm making like a 4% return a year just on the birth of new slaves.

• 7:51Speaker 02

  Right.

• 7:51Ryan Holiday?

  And that it's this calculation that ultimately gets in the way of him doing what, say, Washington is able to do. So I don't know if it's true that they were all, that everyone was always doing their best.

• 8:03Speaker 02

  Well, you're talking about slavery, which is, I mean, generally, there's some things that are universal and they're always evil. Slavery, I would think would be one of them. I think what's interesting about Thomas Jefferson was I think he was really introspective and he was a genius.

• 8:14Ryan Holiday?

  Yeah.

• 8:15Speaker 02

  And he was smart enough to know that what he was doing was not defensible and would not be defended after his death. He understood all that and he wasn't willing to pay the price. So he was hoping that they were on a downward slope where it would slowly fade away.

• 8:28Ryan Holiday?

  Would solve itself.

• 8:29Speaker 02

  Right. And that would allow him to escape and live his life the way he wanted to live and the way he wanted to live it. Almost, you know, for his own sanity, maybe it would have been better to be a little stupider than he was. But he's sort of, you know, stupid people have the advantage of that. So I think that, you know, he's a really unique case because he sort of made America what America is. And built into that is the fact that he knew that he was engaged in something un-evil.

• 8:51Ryan Holiday?

  Yeah, it is, it is funny that they, the argument that they weren't introspective. Because actually, when you really dig into the lives of the people, you find that they were quite introspective. There's all sorts of things that we sort of assume were cut and dried, but actually they, they, they went back and forth on, they, they tortured themselves without. And then also, it seems like a silly argument to me because like, when I look at the flaws of those people, when I look at the, the most indefensible or the most egregious things they, they did, I see that as part and parcel of whatever that not, that trait of not being introspective was. It's like, if, if they could have thought a little bit more.

• 9:29Speaker 02

  Yeah.

• 9:30Ryan Holiday?

  It probably would have been better.

• 9:32Speaker 02

  I mean, I think one of the reasons people think that they're not introspective people in the past is because it's hard to accept the reality of somebody that's not alive right now. It's just very hard to make them anything but kind of a character in your mind and not real.

• 9:45Ryan Holiday?

  Yeah.

• 9:46Speaker 02

  And what I meant by, you know, right now, I assume that Jefferson was involved in very evil behavior and knew it.

• 9:52Ryan Holiday?

  Yeah.

• 9:53Speaker 02

  And I think that the same is true today.

• 9:56Ryan Holiday?

  Sure.

• 9:56Speaker 02

  You just don't know what, you know, it's not, whatever it is, the people are kind of letting themselves off the hook now.

• 10:03Ryan Holiday?

  Yeah.

• 10:04Speaker 02

  By sort of, sort of relegating it all to the past. Like now we have it figured out and now we're, we got our heads on right. I just think that you run into this problem where it's very hard to understand what people were thinking in the past and what was going on. But I do think that people are basically the same.

• 10:21Ryan Holiday?

  Yeah.

• 10:22Speaker 02

  And there might be some outliers. So I wrote this book, Murder in the Dollhouse, about this guy, Fotis Dulos, who killed his wife. I think that I came across him, I didn't understand him at all. Like, he was an outlier, like a murderer. But mostly like 99% of people are basically the same. If you put them in the same situation, they'd behave the same way that the other people in that situation did.

• 10:42Ryan Holiday?

  Yeah.

• 10:43Speaker 02

  And as a writer, I think my whole premise is based on that, which is if I kind of feel something, most other people are going to feel the same way. If they were in my shoes, they'd feel the same way. And if I was in their shoes, I'd feel the same way. And that's also true with people like Sam Zemurray. Even though he was incredibly talented, ambitious, smart, had a lot of energy, did all these things, he still, at the end of the day, wanted to do the right thing. And he still felt at some level that he wasn't doing the right thing. Which is why he tried to make it right.

• 11:11Ryan Holiday?

  Yes.

• 11:11Speaker 02

  You know, by a charity and everything else he did, and those things are appreciated. I mean, people are still benefiting from them. And I assume that with Thomas Jefferson, at some level, he was operating the same way.

• 11:21Ryan Holiday?

  Yeah, I mean, that's what is so remarkable about philosophy and, and art and music is how they manage to capture emotional states or human experiences that reach across centuries or generations. And you're like, oh, I feel the exact same way like that.

• 11:38Speaker 02

  Because the fundamental problems haven't changed. They're still the same problems.

• 11:42Ryan Holiday?

  Yeah.

• 11:42Speaker 02

  Still the same fears, still the same homes. People have not changed.

• 11:45Ryan Holiday?

  Right, not in 2000 years, maybe in 10,000 or 20,000. But even you look at cave paintings and you're like, there's something sort of fundamentally.

• 11:55Speaker 02

  What this does is it gives you like a degree of humility.

• 11:58Ryan Holiday?

  Yeah.

• 11:59Speaker 02

  Which is, it's like Ecclesiastes.

• 12:02Ryan Holiday?

  Yeah.

• 12:02Speaker 02

  That's my Stoics, you know? Which is all these problems that you have now, people have had not once before, but innumerable times before. Until it disappears, until the event horizon, you know? And what you're dealing with has been dealt with and will be forgotten and will be dealt with again and again and again.

• 12:17Ryan Holiday?

  Yeah, yeah. And, and maybe the only thing we can do is practice a little introspection and try to share some of those lessons. I mean, some of the things are ones you can only learn from experience, but I think often you look at the sort of larger than life lives and you sort of go, okay, like at that level, if it doesn't solve it, you know, at that level, if it doesn't fill the hole or, you know, make them feel secure or good, like, why am I thinking that if I just accomplish enough or achieve enough or make my mark like deep enough, it'll do it for me?

• 12:56Speaker 02

  Right, because that's why sports are a good model. If you ever played sports, which is, you don't play sports thinking you're going to change the game, you're going to change the rules of the game, you're going to solve the game and there will be no more reason to play a game anymore. You're just thinking of that particular game and your particular teammates and that you want to do as well as you can. Mostly your first motivation is not to make a fool of yourself and to prove that you belong in the game, you know? And then if you get ambitious, you want to be good at the game. And that's basically what we got is, you know what I feel like? My father just turned 93. You're making me think of my father. And he gave this, I taped it, he gave a little, he must have prepared it, but he said this thing, he said that he sees his kids and his grandkids as ambassadors he sends into the future.

• 13:41Speaker 02

  Past his death.

• 13:42Ryan Holiday?

  Yeah.

• 13:43Speaker 02

  And I think that there's something, that's the best you can do. I mean, that was, he doesn't really, he's 93, he hasn't said a lot of things that I haven't heard before, you know?

• 13:50Ryan Holiday?

  Yeah, yeah.

• 13:50Speaker 02

  But I hadn't heard him say that before and it was, uh, it's inspiring to think like you do what you, what you can do, what is in your power to do, you try to do the best you can and don't really worry about.

• 14:01Ryan Holiday?

  Well, there's like different levels of that sort of multi-generational impact that people try to have. And then there's this for people trying to sort of bend the, the world to their will, trying to, you know, sort of make their dent in the universe. The irony is how often those people like neglect the ambassadors that they're sending to the future that live at home.

• 14:20Speaker 02

  Yeah, well, they don't, maybe don't think of them that way.

• 14:21Ryan Holiday?

  Right, right.

• 14:22Speaker 02

  You know, I mean, it's like, I, I once wanted to write a book just about little brothers, a little, because I'm a little brother.

• 14:28Ryan Holiday?

  Yeah.

• 14:29Speaker 02

  And when you're a little brother, you have humility usually. I mean, you can become very angry, I guess, but little brothers, because when you arrive, it's already happening.

• 14:37Ryan Holiday?

  Yeah.

• 14:37Speaker 02

  The game is underway, you know? And so much of what your personality becomes depends on your birth order.

• 14:43Ryan Holiday?

  Yeah.

• 14:43Speaker 02

  So when you're a little brother, you have to figure out, or little sister, I guess, or the youngest sibling, have to figure out how to fit in an existing paradigm.

• 14:50Ryan Holiday?

  Yeah.

• 14:51Speaker 02

  It gives you like a lot of humility and realizes that you're not inventing new tools, you're working with tools that are already there.

• 14:56Ryan Holiday?

  I thought about a line from one of your books two weeks ago, it was my son's like second to last lacrosse game. You have that great scene in Peewee's where you like go up to the coach and you're like, hey, like my son needs more, more playing time or what's going on? And the coach is like, hey, let me, let me ask you a question, is, is he having fun? And then you're like, yeah. And, um, he's, he's like, what the fuck do you care?

• 15:17Speaker 02

  Right.

• 15:17Ryan Holiday?

  You know? And my, my son had like basically played like 40 seconds in this whole game.

• 15:22Speaker 02

  Right.

• 15:22Ryan Holiday?

  I was going to go up to him and be like, it's okay, like it's cool. And like before I could even say anything to like console him, he's like, hey, can I do lacrosse again next year? And I was like, I mean, sure, like I thought you were going to be upset and like, you didn't even know, I don't think, I don't think it computed for him that it wasn't good, like that it didn't go well. And then, so you just think about like, that is our, our sort of ambassador of the future is, is like our children, obviously, but then it's also these little lessons, hard one or otherwise, and we're either paying them for it in books or in, in art or in conversations. That is, that is the, we don't learn a lot and we don't change, but like there are little things here or there.

• 16:02Speaker 02

  Well, to me, the big lesson for Peewee's was, so I've seen crazy sports parents.

• 16:07Ryan Holiday?

  Yeah.

• 16:07Speaker 02

  I judge them harshly. I make fun of them, I mock them and I don't like them.

• 16:11Ryan Holiday?

  Yeah.

• 16:12Speaker 02

  And then when my kid showed a little bit of talent for hockey, I became one of them immediately, instantly.

• 16:17Ryan Holiday?

  Yeah.

• 16:18Speaker 02

  And I couldn't, it was like a possession, was like a kind of rabies of the soul. That's the big, which is when it's your kid, it's so deep. And when your kid does something well, there's nothing like it, man. It's like nothing, so it's, the point is that just because you understand these things doesn't mean you won't spare yourself or others while going through them. And only later do you gain a little bit of perspective, only because it's not happening. And I assume if it happened again, I would act the same way again, I would try not to. But it was like a big check on me, which is what I was valuing, which was not, not what my kid was valuing. My kid was valuing the experience, the, a lot of these even NHL players, when they're interviewed, they say their best moment in pro hockey was, actually, there was a book

• 17:00Speaker 02

  about this guy, Derek Bogard, who played for the Rangers, a really good book, I'm forgetting the name of it. And he would became a fighter in the NHL and he got CTE and he has a tragic story. But in the book, he says that his favorite moment in all of hockey, playing in the NHL and everything, was just driving to the games with his father.

• 17:16Ryan Holiday?

  Wow.

• 17:17Speaker 02

  That was it.

• 17:17Ryan Holiday?

  Yeah.

• 17:18Speaker 02

  You know, and there was a really funny, it just sort of encapsulated, which is there was a really funny meme or whatever going around among kids my kid's age, which is, it showed you how kids view the game, like it was, it was a kid tweeted, basically when you've driven three hours to a hockey tournament and you suddenly realize you forgot your hockey bag and have to tell your father.

• 17:38Ryan Holiday?

  Yeah.

• 17:39Speaker 02

  You know?

• 17:40Ryan Holiday?

  Yeah.

• 17:40Speaker 02

  And that was actually retweeted by a bunch of guys in the NHL and stuff, because everyone had that, you know, experiences, having to buy all new equipment or something like that, or borrow a bunch of equipment at the rink. So, but that's what they're thinking about.

• 17:50Ryan Holiday?

  I think about that one all the time that like is attributed to the Sandlot and it feels so true, but it's actually not in the movie, the Sandlot. It's like, it's quoting the movie, it's not real, but it's, it says like, you know, at some point, there was the last time that you went outside with all your friends to play baseball and none of you realized it.

• 18:06Speaker 02

  Yeah.

• 18:07Ryan Holiday?

  And like, that's more what your kids are thinking about, like, because they still like it, they're still having fun with it. They're, they're thinking about it as this thing they like to do. And our instinct is to sort of professionalize it or to raise the stakes of it.

• 18:22Speaker 02

  Well, it's funny, because I, the funnest I ever had playing sports was an adult league softball team that played just with my friends, no coaches, we won the championship and we got really bad. We won the championship, then we went to college, everybody came back, whatever they were, overweight, on drugs, not paying attention. And we went from a great team to a horrible team.

• 18:41Ryan Holiday?

  Yeah.

• 18:41Speaker 02

  And I got, everyone said I should make my father the coach. Okay, because my father looks a lot like, or looked a lot like Walter Matthau in the Bad News Bears here, so they call them, you know, butter maker, boiler maker. And my father took it super seriously and attempted to, to do all this. And we couldn't explain to him, this is a joke, man. Like you've just made us like, you're having us run, run wind sprints.

• 19:05Ryan Holiday?

  And you finally think of that memory as well, like it's probably time you enjoy getting to spend together.

• 19:10Speaker 02

  Oh, yeah, it's really, really, really funny. My friends all talk about it. He had us doing very advanced shifts that they now use computer models for, because he grew up with the Ted Williams shift, you know? And we're like, I'm not going to do it because I think it looks, I'm not putting the short stop in right field. He's like, why it'll work? I'm like, because it looks stupid and we'll be made fun of. That's another huge motivation in life, which is just not to get made fun of. So it's another, a great thing for me in a book is in the Tom Wolfe book, The Right Stuff, where he's got the astronauts sitting upside down in the capsule, waiting for the blast off. And everybody's wondering what he's thinking and all attention's focused on this guy. And they say what he's thinking is, I don't want to screw the pooch, man.

• 19:46Ryan Holiday?

  Yeah.

• 19:47Speaker 02

  Just don't let me fuck up.

• 19:49Ryan Holiday?

  Dude, I just read this Tom Wolfe thing for the book that I'm researching right now. He wrote this weird sort of very new journalism piece about these two aircraft carrier pilots flying over Vietnam. It's called like Nick and Charlie Go Jousting or something. It's so incredible.

• 20:04Speaker 02

  I think I've heard of it. I mean, I'm sort of a Tom Wolfe fanatic a bit. It's weird that I've never read it. It must've been running some like New York, in New York Magazine.

• 20:11Ryan Holiday?

  Some weird magazine that you've never heard of.

• 20:13Speaker 02

  And there's some reason probably why he didn't anthologize it.

• 20:15Ryan Holiday?

  I know, but it was really good. It was like exactly what I needed. But did you watch the Man in Full TV show?

• 20:20Speaker 02

  I watched part of it.

• 20:22Ryan Holiday?

  I was so mad.

• 20:23Speaker 02

  Yeah.

• 20:24Ryan Holiday?

  I was so mad.

• 20:24Speaker 02

  Yeah. Well, it's really hard because the better the book is, usually the worse the movie is gonna be. Because so much of what makes a book good is the voice.

• 20:33Ryan Holiday?

  Yeah.

• 20:34Speaker 02

  And there's no way to get the voice. So they try to other ways to get the voice and they can't figure out what's missing. It's why there's never been a good movie of On the Road. There'll never be a good movie of The Great Gatsby. Because they're all about the voice. And when you're a reader, you get hypnotized by the voice of the writer.

• 20:49Ryan Holiday?

  And the rhythms of the speech and the descriptions and yeah.

• 20:54Speaker 02

  The books that make good movies are dependent on plot. If you have a clever plot or something like that, or if they take a classic and kind of completely rip it up and start over. So we'll see about The Odyssey this summer, I guess. But The Odyssey is different anyway.

• 21:07Ryan Holiday?

  But it's also got an incredible plot, right?

• 21:09Speaker 02

  Yeah, that's right. I'm saying The Odyssey is different. It's not about the, it can't be about the voice because it's been translated and blah, blah, blah, blah, blah. So Tom Wolfe, no one's figured out. I guess the movie, The Right Stuff is pretty good.

• 21:17Ryan Holiday?

  Yeah. But again, it's because it's a very action-packed story.

• 21:20Speaker 02

  Right. And because Philip Kaufman, who was a director, was a great director, underrated director, I think. And he understood that what he could do was just about images. So he has an image at the beginning of that, you know, movie where you have Sam Shepard, like the coolest guy of all time, riding through. It could be a Western, it could be a John Ford movie, riding on a horse through the brush, you know? Could be John Wayne in The Searchers. And he comes over a rise and there's the plane that's gonna break the sound barrier just with the flames coming out of the tail. And it's this moment of the cowboy and the rocket, and you realize it's the same guys and it's the same moment.

• 21:58Ryan Holiday?

  Of every era, just it's, it's the archetype just on a new horse.

• 22:02Speaker 02

  Right. And the pilot is the cowboy.

• 22:04Ryan Holiday?

  Yes.

• 22:05Speaker 02

  Right. And, and, and that's all registered subconsciously in a moment with an image. And that's what movies can do. And so that's why I think that that was actually a good movie.

• 22:13Ryan Holiday?

  I am ready for the weather to turn because I'm, uh, I'm tired of t-shirts. I want to go back to my sweaters. Usually wear sweaters when I'm on stage or when I'm recording stuff, but not like around, not during the day. Because it's like, I don't know, 100 degrees here still. But I got some great sweaters from Quince that I am excited to wear. I got some last year. I picked some new ones out. And they're just hanging on the shelf, ready to go into the rotation. Quince has got great t-shirts. They've got great light sweaters. And everything at Quince is priced 50 to 80% less than similar brands. They work directly with ethical factories and cut out the middlemen. So you're paying for quality, not brand markup.

• 22:55Ryan Holiday?

  And Quince goes way beyond clothing. They've got sofas and ceramic cookware, premium bedding. It's the kind of brand you can end up recommending to everyone for everything. Find your next fall favorites at Quince. Download the Quince app for app exclusive offers or go to quince.com. Get free shipping on your order and 365 day returns, now available in Canada and the UK too. And when Quince asks you where you heard about them, let them know it was The Daily Stoic. It's the best way to support the show. This is the busy season, right? More calls, more customers, more chances that something can slip through the cracks. Staying ahead means having the right system, not just working harder.

• 23:35Ryan Holiday?

  And that's why today's episode is brought to you by QUO, Q U O, the business phone system built so that you never miss a call. It is the number one rated business phone system on G2, trusted by over 90,000 businesses who rely on it to stay reachable and look professional every day. All your calls, texts and voicemails live in one place. So anyone on your team can pick up the conversation, see the full history and respond fast. And QUO integrates with the tools your team already uses. HubSpot, Zapier, Claude, whatever. And it helps you save time, stay organized and spend less effort chasing down information between systems. Money is on the line. Always say hello with QUO.

• 24:14Ryan Holiday?

  Try QUO for free. Plus get 20% off your first six months when you go to quo.com/dailystoic, Q U O dot com slash daily stoic. You think they'll ever make a good movie of Confederacy of Dunces?

• 24:26Speaker 02

  No, I don't think so. For the same reason. It's, it's the voice. And what I always really loved is that I go back to again and again and again and again for sustenance is Walker Percy. So how could you ever make a good movie, a good movie of The Moviegoer?

• 24:39Ryan Holiday?

  Yeah, that would, that's like some adaptation level, like.

• 24:43Speaker 02

  It's gotta be something completely different. It's all internal and it's all the voice and it's all the detachment that he feels from his own life. He is a detached person.

• 24:53Ryan Holiday?

  Well, Confederacy of Dunces is funny. So you could potentially get to the dialogue and the absurdity. Yep. You know, you have the hot dog vendor eating all the hot dogs and making fun of everyone. A comedic actor could probably make hay of that in a good way. Like, I think you, you could probably do it. But making a good movie of The Moviegoer might, might be genuinely impossible. Because it is, yeah, it's about the alienation. It's about the weirdness. It's about the aimlessness. And there's not a good movie of The Catcher in the Rye either, for the same reason. And I, I sometimes say that Walker Percy's The Moviegoer is, is Catcher in the Rye for adults.

• 25:29Speaker 02

  Yeah. Well, they're very, I'd say they're both for adults, you know?

• 25:32Ryan Holiday?

  Yeah. But I'm just, it's instead of being a 17-year-old who's alienated, it's a 31-year-old who's alienated.

• 25:39Speaker 02

  Yeah. And by the way, just making me think like the, maybe the best that I think of off the top of my head, movie adaption is No Country for Old Men, which I understand was written originally as a script, I think. And then he adapted it the other way. That's why, there's another really great book by James Salter called Solo Faces. You ever read that book?

• 25:58Ryan Holiday?

  I am on a huge James Salter kick right now. And I was just thinking, when you were talking about great books that got butchered. He wrote, did you read The Hunters?

• 26:06Speaker 02

  Yes.

• 26:06Ryan Holiday?

  And that was a Robert Mitchum movie. But it's like not about, there's, there's nothing from the book in the movie, other than it's about fighter pilots and.

• 26:14Speaker 02

  Right. Like, because they want the IP and they can sort of slap this thing underneath it.

• 26:18Ryan Holiday?

  Yeah.

• 26:19Speaker 02

  And, um.

• 26:20Ryan Holiday?

  But Solo Faces started as a, as a screenplay for Robert Redford and he rejected it.

• 26:23Speaker 02

  Right. And it's great, man. It's, I had a really good friend growing up who died really young. And he kind of had gone off and lived that kind of life.

• 26:32Ryan Holiday?

  Yeah.

• 26:33Speaker 02

  And I never really knew what happened to him after like early twenties. He died like in his early thirties.

• 26:38Ryan Holiday?

  Yeah.

• 26:38Speaker 02

  And I felt like reading that book, I was reading about his, his life. Which is a power of that, of that, of his writing and his voice.

• 26:45Ryan Holiday?

  I loved The Hunters. I loved Burning the Days, which I think was an incredible memoir. And then I just read Light Years, which is the one about like a marriage falling apart. I haven't, I, I don't know if I've actually read Solo Faces.

• 26:58Speaker 02

  Well, his famous book, you know, is A Sport in a Pastime.

• 27:01Ryan Holiday?

  Yeah.

• 27:02Speaker 02

  Which is very dirty.

• 27:03Ryan Holiday?

  Yeah. Yeah.

• 27:04Speaker 02

  Somebody came up to me once at the gym and I was reading it. I just, it was like on page one. And they started talking about it. And like later I had to rethink what that conversation was really about.

• 27:13Ryan Holiday?

  That's like not a book you should be reading in public.

• 27:15Speaker 02

  I didn't know.

• 27:15Ryan Holiday?

  Yeah, yeah.

• 27:16Speaker 02

  I was in my twenties and I was at the gym, yeah, reading it. But, you know, and also his short stories.

• 27:22Ryan Holiday?

  Yeah.

• 27:22Speaker 02

  I think somebody, when I turned like 22 or 23, somebody gave me his book of short stories, Dusk.

• 27:27Ryan Holiday?

  Yeah.

• 27:28Speaker 02

  Which, there's this thing that old European novels have, like, I mean, like the Camus era that captures something about how strange it is to be in a city that you don't live in. That I've never read an American novel capture it in the same way until James Salter. So he clearly must have been hugely influenced by those books.

• 27:44Ryan Holiday?

  Yeah.

• 27:45Speaker 02

  You know, so when you read Dusk, like a story like American Express or something, just what it's like to be young and in a place that you have no reason for being.

• 27:53Ryan Holiday?

  Yeah. Yeah. I thought, when I was rereading The Hunters, I, I thought of it as like these fighter pilots. It's the same story. Like these guys are just desperate to make their mark. They all want to make ace. They, they're, they're a Silicon Valley entrepreneur. They're a cowboy. They're a, they're an athlete. They're just whatever that thing is that you think, if I just achieve some, some semblance of immortality, I will matter. I will be important. If I can be the best in the world at this thing. That just, I think he just captures that sort of timeless, human drive. But in it, it's always fascinating when someone does it in like a profession or a domain that you don't expect to see that.

• 28:38Speaker 02

  Yeah. And he changes how you see the world.

• 28:40Ryan Holiday?

  Yeah.

• 28:40Speaker 02

  I mean, you can't really see, and he's, it's really about competition. It's like the same as sports. And the fact that he himself was like this pilot adds to it. But he was very introspective, probably so introspective that it inhibited his career as a, in the air force, which is ultimately he left the air force. And I think that, um, it is good sometimes for certain things to be not so introspective, to be, it's a huge advantage to be a little dumb. And I say that as somebody who considers himself a little dumb. Takes me a little long to get things. I'm a little slow about a lot of things. Have to reverse engineer them to understand what's happening. Sometimes somebody, I was talking about this this morning, sometimes if somebody were to come up to me and say, nice to see you. With and shake my hand, but stab me in the back with the left hand. I will come away thinking,

• 29:25Speaker 02

  oh, it was nice to see him. That is a nice person. He said, nice to see me. It'll take me years to realize I've been shanked.

• 29:31Ryan Holiday?

  Yeah.

• 29:31Speaker 02

  You know?

• 29:32Ryan Holiday?

  That's funny. I thought the interesting part of Burning the Days is where he talks about, cause he flew with Buzz Aldrin and Ed White. When they land on the moon and they go into space, he's like fucking pissed.

• 29:44Speaker 02

  Right.

• 29:44Ryan Holiday?

  And you go, oh, yes. Like from the outside, these are selfless public servants who are motivated by duty and honor and country, and they are, but they also want to be the best in the world. And the people they're flying with are their, are their buddies and their wingmen and their compatriots. And then they're also competition to be number one on the equivalent of call sheet.

• 30:07Speaker 02

  It's everybody's in that situation where the person you're friends with is also your competition. And if that person succeeds, you don't succeed.

• 30:14Ryan Holiday?

  Yeah.

• 30:14Speaker 02

  And when they succeed, you have to pretend like you're happy for them.

• 30:18Ryan Holiday?

  Yes.

• 30:18Speaker 02

  You know, and that's just something that we've learned to do. And especially in a book like James Salters, because it's about the Cold War and what's good for the West and good for America. So there's this other level of self sacrifice, but he feels like he's made a terrible mistake.

• 30:33Ryan Holiday?

  Yeah.

• 30:33Speaker 02

  Because he was on the path.

• 30:35Ryan Holiday?

  Yeah.

• 30:35Speaker 02

  You know, I have a friend, when my son was playing hockey, I have a friend who said, oh, so he's on the path. He was a very, this guy's a great hockey player.

• 30:43Ryan Holiday?

  Yeah.

• 30:43Speaker 02

  And I'm like, what fricking path, you know? And he's like talking about the NHL path, which my son was never on. I've never known anybody on, but just that he kind of saw it that way, which is, what's the goal here?

• 30:55Ryan Holiday?

  Yeah.

• 30:55Speaker 02

  You know?

• 30:56Ryan Holiday?

  Yeah.

• 30:56Speaker 02

  The goal is, in the case of me and all the people I know, adult hockey on Tuesday nights. That's the goal.

• 31:02Ryan Holiday?

  Yeah.

• 31:02Speaker 02

  You know?

• 31:02Ryan Holiday?

  Right.

• 31:02Speaker 02

  But so there are people that see the goal as the goal.

• 31:06Ryan Holiday?

  But it is interesting how much in common the people on the path, whether they're trying to be a fighter pilot, or a Navy SEAL, or a professional basketball player, or, you know, a billionaire, or a senator, like the path is the path is the path. And all these kind of elite domains, it's not just like the same path, but it's the same personality type in there too.

• 31:27Speaker 02

  Yeah. And I'm a writer, so I don't have that. I don't understand it. I'm fascinated by it. It's human nature, you know?

• 31:33Ryan Holiday?

  But of course you have in that league, in as a magazine writer and as an author. No, and it probably as a TV writer also, like.

• 31:41Speaker 02

  It's very kind of you to say that. Thank you very much.

• 31:43Ryan Holiday?

  It's very true. I mean, that's the funny thing is it doesn't feel that way sometimes to the person, but all you have to think about is like, how many people would literally kill someone to have what you have? And that's a sense of where you are on the path. Do you know what I mean?

• 31:56Speaker 02

  Yeah.

• 31:57Ryan Holiday?

  Like.

• 31:57Speaker 02

  I mean, thank you. That's, I mean, but I, but I'm not, I'm so focused on,

• 32:04Speaker 02

  you know, what, what a great story is and watching these other people. I do, I guess there have been times where I think about like where I am in the whole blah, blah, blah, blah, blah. But I also know that the writers from 20 years ago that were considered great are forgotten. And the writers that were forgotten are considered great. And one of the great examples for me is like the, the painter Chardin, who he, when he painted his paint little scenes, they were kept like in people's kitchens so they could look at food while they ate, you know?

• 32:33Ryan Holiday?

  Yeah.

• 32:33Speaker 02

  And the, in the main rooms in the museums were the giant pictures of Napoleon on horseback.

• 32:38Ryan Holiday?

  Yeah.

• 32:38Speaker 02

  And now you go to like the Met in New York and it's reversed, man. Those big giant paintings of Napoleon are out by the elevators and the Chardin paintings are in the main room.

• 32:47Ryan Holiday?

  Yeah.

• 32:48Speaker 02

  And so you, you can't really know in the long run, how any of it's going to turn out.

• 32:52Ryan Holiday?

  Well, also it doesn't make a fucking difference to either of those painters.

• 32:56Speaker 02

  No.

• 32:56Ryan Holiday?

  Cause they're both, like it, it evened out for both of them. And the fact that one is now here and one is here is totally irrelevant to either of them.

• 33:03Speaker 02

  So you think, would you rather be successful in the long run or have a much better life? And you think probably the much better life.

• 33:09Ryan Holiday?

  Or would you just, what it ultimately comes down to is like, who, who enjoyed doing the thing the most and didn't torture themselves so fucking much? Like Salter, who we're just talking about, was like a great writer and, you know, maybe at his peak, although he did make some money from some movie stuff, was considered a writer's writer. But you do get the sense that he felt somewhat tortured and inadequate as a writer. Like it, I'm not sure he always had the best time, you know?

• 33:39Speaker 02

  Yes.

• 33:39Ryan Holiday?

  And, and, and so.

• 33:41Speaker 02

  By the way, I knew somebody, a person that was involved in his career, who was kind of making fun of his lack of success, which is unbelievable.

• 33:47Ryan Holiday?

  Right. But then the fact that he's been slowly subsequently vindicated and that his star is rising, again, doesn't matter. Like he's, he's not able to, you can't dine out on, on your

• 33:58Speaker 02

  Well, think about it. This is how I always think about it. Like, think about it like a band.

• 34:02Ryan Holiday?

  Yeah.

• 34:02Speaker 02

  Okay. What do most people want from a new record? All the records aren't the thing they were when, they want a slightly different version of the record they already like.

• 34:10Ryan Holiday?

  Yeah.

• 34:11Speaker 02

  Okay. So if you come to them with something new, they're going to fricking hate it.

• 34:15Ryan Holiday?

  Yeah.

• 34:15Speaker 02

  Until they learn how to listen to it, the record itself has to teach the people how to listen to it. So the best records usually get hammered by most critics and they don't sell. They sell over a period of 20 years as people figure out how to listen to them.

• 34:30Ryan Holiday?

  Yeah. It's hard to be ahead of your time. It means that you're not of the time.

• 34:35Speaker 02

  Right.

• 34:35Ryan Holiday?

  Which is now.

• 34:36Speaker 02

  And not that, you'll get resistance from everybody, from agents, from editors who don't want you to do this thing, whereas you know that this is the thing you gotta do.

• 34:43Ryan Holiday?

  Right.

• 34:43Speaker 02

  So it takes a, like a lot of confidence to do that. And James Salter did that for years. You know, and he finally, at the end of his life, he started to be recognized, like you say. And by then he was old.

• 34:56Ryan Holiday?

  Yeah.

• 34:56Speaker 02

  You know, he wanted what he wanted when he was young, which was to be an ace. He writes about being an ace.

• 35:02Ryan Holiday?

  Yeah.

• 35:02Speaker 02

  Shooting down three MiGs.

• 35:03Ryan Holiday?

  Five.

• 35:04Speaker 02

  Five MiGs. Sorry, I messed it up. And he did, he, he didn't get it.

• 35:06Ryan Holiday?

  He got one and a half.

• 35:08Speaker 02

  Yeah, in Korea.

• 35:09Ryan Holiday?

  Yes.

• 35:09Speaker 02

  And then when he became a writer, he wanted the same thing.

• 35:12Ryan Holiday?

  Yeah.

• 35:13Speaker 02

  You know, and again, he shot down one and a half MiGs.

• 35:15Ryan Holiday?

  Yeah, totally, totally. Except that's really fucking hard. Like, like as, as time passes, in a way, you're just like, you did it. You were in, you were in the league.

• 35:26Speaker 02

  Right.

• 35:26Ryan Holiday?

  You know, like you were, you were one of a small number of people to ever do this thing.

• 35:32Speaker 02

  Yeah.

• 35:33Ryan Holiday?

  Obviously what he couldn't anticipate is almost no one shoots down planes anymore. That's not how, like by the time Vietnam comes along, planes don't fight each other in the air anymore. It's just not, it's not.

• 35:44Speaker 02

  I know. Well, that's the other thing, which is the, the, the language that you live your life in.

• 35:48Ryan Holiday?

  Yeah.

• 35:48Speaker 02

  Becomes unintelligible to the generations that follow.

• 35:51Ryan Holiday?

  Yes.

• 35:51Speaker 02

  You know? So like a lot of my career was about magazine writing. And a kind of magazine writing that doesn't really exist anymore.

• 35:59Ryan Holiday?

  Yeah.

• 35:59Speaker 02

  You know? I mean, it's writing, it's writing is writing, but like the Tom Wolfe stories, where would he write those? Some of them he would sell here and there, but.

• 36:06Ryan Holiday?

  They'd be fucking TikTok videos.

• 36:08Speaker 02

  Yeah. So we're, we're like looking at his accomplishment, but to people that are growing up now, it doesn't, it wouldn't even make sense. It's like a different language.

• 36:16Ryan Holiday?

  Yeah. And look, that happens not just in, in sort of art or whatever. Like I was the director of marketing at American Apparel, which was at one point a very cool job. And I thought, I thought at that time, when I was walking away to be a writer, I would be like, well, it's like, hey, I was the whatever at Apple or like now people don't, the company doesn't even exist. It was bankrupt twice. It has no, like, and it might come back around as like a sort of a retro company at some point in the future. But like, if you think that, that this thing is gonna have staying power or matter, like.

• 36:48Speaker 02

  Not like that. The meaning changes. So like you're making me think of like my father, go back to my father. He was a pretty high level executive at Sears.

• 36:55Ryan Holiday?

  Yeah.

• 36:56Speaker 02

  You say people that now they're like, they have this idea of this old tired store at the mall.

• 37:01Ryan Holiday?

  Kmart or something.

• 37:02Speaker 02

  Yeah.

• 37:02Ryan Holiday?

  Yeah.

• 37:03Speaker 02

  But at the time, you're like, no, Sears was like, Sears gave Muddy Waters his first guitar, man. You could order a house from Sears.

• 37:09Ryan Holiday?

  Right.

• 37:09Speaker 02

  Sears was like Amazon.

• 37:10Ryan Holiday?

  So yeah, being an executive at OpenAI, right? It's like the biggest company in the world. Yeah. Like, yeah, exactly. And then it, so there's a ticking clock on all this stuff. And to attach your value or your identity to it is a fragile thing.

• 37:24Speaker 02

  Well, it's funny, cause there's like, one of the things that made me want to be a writer was, it was all about that voice, was freshman year in high school, in a class I got, I think a Dean. Okay. So that class, which is English, tended up making me want to be a writer.

• 37:40Ryan Holiday?

  Yeah.

• 37:40Speaker 02

  Because she had, we had to read a book of short stories. And I read the Hemingway story in our time. And from the first line of that story, it was like, made you feel something different than you ever felt before. The lesson of that story is, the guy says, you should never love anything you can lose. Okay, but that's what life is. I mean, there's no way that's, that always, that you can lose everything.

• 38:05Ryan Holiday?

  But what you fell in love with, the way those words worked and the feeling it evokes, like magazines can go away.

• 38:13Speaker 02

  Right.

• 38:14Ryan Holiday?

  But that's the, the doing the thing can. That's what I mean. It's like, if you look back and you're like, hey, I'm proud of the things I wrote. I'm proud of my growth as a writer. I'm, I'm proud of who I was in this industry or whatever, then, then you can have a pretty good go of it.

• 38:28Speaker 02

  Right.

• 38:29Ryan Holiday?

  But if you're like, no, no, no, I need to be one of the guys. I need to have won the great prizes. I need to get the best slots. That's something you can lose.

• 38:37Speaker 02

  Yeah. But, but by the way, so like, if you're like, have a slightly less optimistic turn of mind, you worry that people now aren't reading. Okay. So, and it's not just like my career. Who cares about my career? It's really bad because the kind of literate mind is a different kind of mind. You process the world differently. It's like slow cooked food, man. You need to take time.

• 38:59Ryan Holiday?

  Yeah.

• 39:00Speaker 02

  For things to register, to understand them, to see them. And it's scary that the people that ultimately will judge. Are people that don't really, you're doing something that they're never gonna notice because they're not reading other, it's like when you're writing, you're coming, you're trying to be like the best writer there is, you have the great advantage of you don't need school or any of that, cause it's all available to you in books.

• 39:20Ryan Holiday?

  Right.

• 39:21Speaker 02

  And you find the writers that speak to you and you're basically operating on a sentence level. That's the whole thing.

• 39:27Ryan Holiday?

  Yeah.

• 39:27Speaker 02

  And then you're being read by people who don't know about a sentence or care about a sentence, or you're gonna speak, you know what I mean? And that's.

• 39:33Ryan Holiday?

  But that's the point is like, it has to light you up. And then, you know, if a fraction of the audience appreciates everything that goes into it, great. If the rest of the people just appreciate the, the final product, great. I'm struck by this, and I wanna come back to The Moviegoer, but I'm also struck by the devaluing of, of not just writing and really good writing, but the thinking that goes into really good writing. And I've been talking about this, probably too much for people, but it's like, like what we're talking about here is obviously interesting, and I think we, we've spent some time thinking about it clearly, but like, this is nothing compared to what you and I might sit down and write about this exact topic. Like, I think people, people go like, oh, I heard them talking about this on a podcast. There's also an audiobook about it.

• 40:18Ryan Holiday?

  Those are the same thing.

• 40:19Speaker 02

  Yeah.

• 40:19Ryan Holiday?

  And it's like, no, no, the, like, like Joan Didion had this great line that she said, writing is a hostile act, that like, you're, you're having to like, you're like mounting this invasion. You're like, you're like attacking this other person and trying to replace their thinking and their narrative and their sense of the world with, with the ones you made up.

• 40:38Speaker 02

  Genius.

• 40:39Ryan Holiday?

  Do you know this was her table?

• 40:40Speaker 02

  No.

• 40:40Ryan Holiday?

  Yeah, this is the table she, she put her robe at this table. What's his name could have died at this table.

• 40:46Speaker 02

  John Gregory.

• 40:47Ryan Holiday?

  Dunn?

• 40:47Speaker 02

  Yeah. I always think of that scene where he just collapses at the, very scary. So, but yeah, so what I'd say is like, people have an idea, I think, that you think of something, you have an idea.

• 40:58Ryan Holiday?

  Yeah.

• 40:59Speaker 02

  And then you write it.

• 41:00Ryan Holiday?

  Yes.

• 41:00Speaker 02

  But in fact, all the thinking happens while you're writing. It doesn't make sense until you write. It's like a different part of your brain turns on.

• 41:07Ryan Holiday?

  Yeah.

• 41:08Speaker 02

  And you have access to a different part of your brain, which is when we're talking about ambition and career and all that, doesn't get to that, which is the main thing, which is the actual writing itself. It, it's like.

• 41:17Ryan Holiday?

  It's otherworldly. It's this magical thing, but then also that's step one of the process. And then the other process, like in music of the, of the producing and the, the re-recording and the, the mixing and all, all the stuff that goes into it at, like, these books are not first drafts of these books. These are like so many drafts down the road. And so that refining and that improving and rereading it and realizing, oh, I, I missed this, or I made this assumption here, like, how much thinking and craft and deliberation goes into what the finished product of a thing that you've read.

• 41:52Speaker 02

  Also, like, just speaking of Joan Didion's hostile act, okay, which is, to put it at a very personal level.

• 41:58Ryan Holiday?

  Yeah.

• 41:59Speaker 02

  So, and this goes back to James Salter too, which is, he said, I think in his last book, he has a quote from himself, which is weird. Slightly, slight, slight Van Gogh.

• 42:08Ryan Holiday?

  If you're quoting yourself, just say it again. Like, I don't, I, it bothers me.

• 42:11Speaker 02

  Well, I remember once, when I got, when I was a kid, I got the John Cougar Mellencamp record Scarecrow, and he had a quote on the dust jacket that said, there's nothing more sad nor beautiful than watching generations change hands. And it said, John Cougar Mellencamp.

• 42:24Ryan Holiday?

  Yeah, just, you don't need that second part, it's yours.

• 42:27Speaker 02

  So, but anyway, he said, like, only, that, only that which is written down has a chance to last, something like that.

• 42:33Ryan Holiday?

  Yeah.

• 42:33Speaker 02

  Which is, by the way, it doesn't say it will last, he says it has a chance to last. But, like, I wrote, my third book was about growing up and my best friend growing up and all that. It's a memoir about growing up. And you realize that as you're writing it, you're basically taking a bunch of memories and replacing them.

• 42:49Ryan Holiday?

  Yeah.

• 42:49Speaker 02

  Because writing is never the same, it's just a translation of what you feel and, and that's what I'm gonna remember. So when you write something down, you kind of freeze it and you lose everything else in a way. You preserve, but you also destroy without really meaning to. So it's like a very serious, you know, thing. And that's what, you can even replace people's memories of their own lives. And that's, I think, what she said, so you write about your father, he reads it.

• 43:14Ryan Holiday?

  Yeah.

• 43:14Speaker 02

  That's what he remembers as happening.

• 43:16Ryan Holiday?

  Yeah.

• 43:16Speaker 02

  You know, except maybe not my father, who's a helpfully hostile reader, but, you know.

• 43:21Ryan Holiday?

  Yes.

• 43:21Speaker 02

  There's different versions, but you can see that there's, it's, it's a very intense thing where you kind of save, preserve and destroy while preserving, which is probably maybe what all.

• 43:31Ryan Holiday?

  Well, that's her other famous line, you know, we tell ourselves stories in order to live. People think that's like this beautiful meditation on the role of creativity and art in humanity. And she's saying, no, no, we fucking lie to ourselves so we can live with ourselves.

• 43:46Speaker 02

  I mean, that seems obvious to me, what she's talking about, which is, you have to, see, the whole idea like now about sort of, let's say, destroying the American myth.

• 43:54Ryan Holiday?

  Yeah.

• 43:54Speaker 02

  Okay. If you destroy the American myth, which I happen to love and grew up with and everything else, it's not like it's replaced by the truth. It's just replaced by another myth, which might, but not be helpful, actually.

• 44:07Ryan Holiday?

  Yeah.

• 44:07Speaker 02

  I mean, the myth that we have, that, there's some things about it are helpful. The myth that we'd replace it with might be less true and might be unhelpful.

• 44:14Ryan Holiday?

  Yeah.

• 44:15Speaker 02

  You know, so you gotta be careful about destroying a myth kind of thing. It's like taking someone's legs out.

• 44:20Ryan Holiday?

  Well, I've, I've said this also before, but I, I think a city we both love, which is New Orleans, you, you take down the Robert E. Lee statue.

• 44:28Speaker 02

  Yeah.

• 44:28Ryan Holiday?

  Great. Now there's just a column there for, for eight years or however long it's been, like.

• 44:35Speaker 02

  It's like, you know what it's like? It's like, you know, remember those stories, create your own story, your own, create your own statue? Imagine your own statue. I imagine my friend Mark on that statue, being, celebrating the time he drank 17 shots at Fat Harry's.

• 44:47Ryan Holiday?

  But I mean, that would, almost that would be better than an empty, like, like deciding, hey, we're gonna turn this into an art, like, actually, we're gonna say, I want you to envision your own thing there. That is replacing it. The problem is, what we do with these myths, we have this tendency in, in American culture to, to point someone out as shitty or hypocritical or contradictory or whatever, and then they destroy the myth of Lance Armstrong, and then they have to go so far down the list to, to find the actual winner, that they're just like, nobody won the Tour de France.

• 45:18Speaker 02

  Right.

• 45:19Ryan Holiday?

  And so, so then you're like, okay, but now who are we supposed to say was the greatest in that era?

• 45:24Speaker 02

  And there you need, I mean, I always, that's in the Bible, you know, when David, King David gives his eulogy for Saul and his son Jonathan, he says, oh, how the mighty have fallen. It's about, yeah, these mighty figures of yore, you need them. And they, they make life kind of interesting. You know, but it's, if you, you think about, I'm a little older than you, I'm a bunch older than you, maybe. And I grew up, I was born in 1968, so I grew up with the constant threat of the permanent record. Okay? The permanent record was, you do this in this class.

• 45:57Ryan Holiday?

  File.

• 45:58Speaker 02

  Yeah. Yeah, it's going in your permanent record. And I always expected someday I would find my permanent record, when, say in third grade, rather than engage in cleanup, he jumped out the window and ran home, which I did.

• 46:08Ryan Holiday?

  Yeah.

• 46:09Speaker 02

  You know, or he threw a firework in the, whatever. So, and then I got older and I realized that, oh, the permanent record's a lie, man. There's no permanent record, I'm free, I'm absolutely free.

• 46:18Ryan Holiday?

  Right.

• 46:19Speaker 02

  And then now, because of all the technology, there's a fricking permanent record. There actually is a permanent record. And it's, it's kind of, you, you gotta be able to forget.

• 46:27Ryan Holiday?

  Yeah.

• 46:27Speaker 02

  You know? You gotta be able to like, leave your past behind you. Even like Hemingway, going back to Hemingway. Hemingway wrote his first book about people in Michigan, near Traverse City, Potoske, Michigan, where he spent his summers, like kind of a rich kid spending his summers at a country cottage. And he took all those stories and he wrote them up. And they, he was so hated that he couldn't go back to Potoske for like 50 years. Now Potoske has a bookstore just with his books, but he couldn't go back. And he would not have done that in the age of Facebook or Instagram or anything, cause he would have heard from all those people.

• 47:01Ryan Holiday?

  Yeah.

• 47:02Speaker 02

  You know what I mean?

• 47:02Ryan Holiday?

  No, no, totally. I, I also think, I think about this with my kids, like, how many things I got temporarily into when I was younger?

• 47:09Speaker 02

  Yeah.

• 47:09Ryan Holiday?

  And there wasn't an algorithm keeping a record of what I liked.

• 47:13Speaker 02

  Yeah.

• 47:13Ryan Holiday?

  And then feeding me more of that thing over and over and over again, until that became who I, like, like, I, I do.

• 47:19Speaker 02

  Also gives you a completely distorted view of the world.

• 47:21Ryan Holiday?

  Yeah, yeah, of course. But I, I just even mean like, it's hard to go down rabbit holes and then entirely abandon them.

• 47:27Speaker 02

  Yeah.

• 47:27Ryan Holiday?

  You know, in a world where the algorithm is incentivized to, and so stupid in a way, that it can't understand that you have fleeting and changing interests.

• 47:37Speaker 02

  I mean, basically, there should be a button, you can press it, it forgets everything about you.

• 47:40Ryan Holiday?

  Yeah, like turn, turn limits on.

• 47:42Speaker 02

  Yeah, just like, forget everything you know about me.

• 47:44Ryan Holiday?

  Yeah, yeah, I wanna start, I don't like, I don't like what I like, I'd like to start over.

• 47:47Speaker 02

  You know? So like, a year ago, I hurt my foot, and I was searching for stuff about, I could do about my foot. And now I'm like, I'd like to see a movie about, what's a good western I could see? They go, well, someone with your foot condition.

• 48:00Ryan Holiday?

  Exactly, yeah. No, and, and like, you at least have a whole lifetime of experience, but if you're like 17, these things, like, that's like 40% of what it knows about you is that, that period where you got really into gospel music or something, and now it's like, it, it won't let you grow out of the thing.

• 48:19Speaker 02

  No, it's, it's crippling in some ways.

• 48:22Ryan Holiday?

  So why is The Moviegoer one of the greatest novels ever written?

• 48:26Speaker 02

  Well, I'll give you my experience with Walker Percy, which was, I went to Tulane, and I had like a bit of culture shock when I first got there, just as simple as the way things smelled, the way things looked, the lack of, you know, I loved in Chicago when it was time to put on your jean jacket, and that was gone.

• 48:41Ryan Holiday?

  Yeah.

• 48:42Speaker 02

  There were drunken people roaming around on the street, that was unusual. I was just completely, like, where am I? What's going on?

• 48:48Ryan Holiday?

  It's another world.

• 48:49Speaker 02

  Yeah. And I found at the Tulane bookstore, for whatever reason, no one, I picked up the book by Walker Percy, Lancelot, which is, you know, and it blew me away, like, it's what writing is for, which is it named and described things I had felt, but I had never articulated. And it gave me a way to understand what was happening and in the world, in my life and where I was.

• 49:12Ryan Holiday?

  Yeah.

• 49:12Speaker 02

  And then I went, read everything by Walker Percy, and The Moviegoer is sort of the book.

• 49:17Ryan Holiday?

  Yes.

• 49:17Speaker 02

  And I think it's that. I mean, it's good that I came upon it, like, I didn't get the Grand Canyon, the first run out, I got like some smaller.

• 49:24Ryan Holiday?

  Yeah.

• 49:25Speaker 02

  Feature, which was Lancelot, because that's what he does, which is, he takes something you feel, but have never put into words, and think you're the only one who feels it.

• 49:33Ryan Holiday?

  Yeah.

• 49:34Speaker 02

  And he puts it in language, so you can understand, one, you're not alone, you're not unusual, and two, you can understand what's happening. And it, it gives you this sense that only books can do this, which is, he can take the incoherent, you know, and actually put it into words, make it a real thing. And that's what, to me, what Walker Percy did. And I just recently read that book again, and of, of course, like a great book, I pick up a million things that I didn't even notice the first time around, even though I've, not the first time around, the fifth time around.

• 50:05Ryan Holiday?

  I don't think the first handful of times, I saw him so much as a veteran, struggling to readjust to normal, modern life.

• 50:15Speaker 02

  Yeah.

• 50:16Ryan Holiday?

  Like, I didn't, I didn't sort of see the PTSD. I mean, he's a Korean, he's, there's a Don Draper element to him that you don't really think about.

• 50:23Speaker 02

  But that was common.

• 50:24Ryan Holiday?

  Yes.

• 50:24Speaker 02

  So like, my father was during the Korean War and everything, that was just, that was something everybody did.

• 50:28Ryan Holiday?

  Right. But that doesn't mean it wasn't incredibly alien disorienting.

• 50:32Speaker 02

  It was presented as. Just life.

• 50:36Ryan Holiday?

  Yeah.

• 50:36Speaker 02

  Whereas now it's very notable because it's unusual.

• 50:40Ryan Holiday?

  Yeah.

• 50:40Speaker 02

  I mean, it was, you know, I don't know what the percentage of people who went into the, it was a huge, it was probably a good part of life. So I mean, I think that, and then the terminology PTSD and the way you would treat it. And there were, you know, just a lot of people that had gone through this big experience when they were young and they were trying to deal with it.

• 51:00Ryan Holiday?

  Yeah.

• 51:00Speaker 02

  Trying to recover from it, or whatever you want to say. Even when I was a kid, the movies, I was talking about this, every movie had like a Vietnam veteran character who was just wandering around the fringes, scaring the crap out of kids.

• 51:12Ryan Holiday?

  Scared about, uh, about backfires and just a weirdo.

• 51:16Speaker 02

  Yeah. And by the way, so I, it seemed like the Vietnam war was ancient history to me.

• 51:21Ryan Holiday?

  Yeah.

• 51:21Speaker 02

  You know, but it wasn't really.

• 51:24Ryan Holiday?

  No.

• 51:24Speaker 02

  I mean, in 1978, when I was 10, that was just a few years before.

• 51:28Ryan Holiday?

  Sure.

• 51:29Speaker 02

  But it was sort of quickly covered over, you know, we moved into a different era and it wasn't really talked about. And the only hint of it you got was these movies. I'm thinking of the movies, specifically the river's edge, which scared the crap out of me. I don't know if you remember that movie with.

• 51:41Ryan Holiday?

  No.

• 51:42Speaker 02

  Oh, it's, I'm not even going to describe it, but it's Crispin Glover and Keanu Reeves. And I saw it when I was a kid and it scared the crap out of me.

• 51:48Ryan Holiday?

  Obviously the, the idea of certification in the novel is like one of my favorites. I remember I read that book.

• 51:52Speaker 02

  Sum that up for me again.

• 51:53Ryan Holiday?

  So like, he's in a movie theater and like, when he thinks from his actual life, appear in the movie, like, I think the scene is he's in that movie theater and then that movie theater is in the movie that they're watching. Like, I remember I, I read that, that certification thing was so funny. I was like, oh, that is a great thing. Like, there is something, like you go to New York and people are like, I want to go on the Sex and the City tour. Like, I want to see like the, the establishing shots from a movie, from a TV show that I liked, even though it's like, I could go to museums, I could see historical buildings. We want to see the stuff that we've seen on TV.

• 52:28Speaker 02

  Remind me of a couple of things. One is when my son, who's now an adult, was like four, we went into the supermarket and there was some product, like a Clorox type product, and he went crazy as if he'd seen like George Harrison or something. He's like, there.

• 52:41Ryan Holiday?

  It's from a commercial?

• 52:41Speaker 02

  Yeah, he'd seen it on TV. It was like a celebrity to him. The other thing is, I grew up in a Glencoe, Illinois, a suburb of Chicago. And John Hughes filmed all those movies there and said, I feel like at my high school, which was Nutria High School in Winnetka. And so that was our, like our life, man. Our life was made valid by the fact that the Glencoe Beach was in Ferris Bueller.

• 53:02Ryan Holiday?

  Right.

• 53:02Speaker 02

  And the Home Alone house was in Winnetka and all, and Nutria West was in Uncle Buck. You know, so I understood it. It made us feel seen, like it was real.

• 53:15Ryan Holiday?

  I remember I read this in, in Walker Percy's, The Moviegoer. I was like, oh, that's such an interesting concept. And then I'm watching the first season of True Detective and my storage unit in New Orleans is like the storage unit they go to where he has all this stuff. And I'm like, this is it. And it's like, it should, like, I have no attachment to this storage unit in Shell Net or whatever. And I'm just like, there it is. Like, so there's something about like a novel that captures or explains a thing that didn't have a name before. And you're just like, that's fucking.

• 53:45Speaker 02

  Yeah.

• 53:46Ryan Holiday?

  It's got a couple of little.

• 53:47Speaker 02

  And he's good. There's other, there are other.

• 53:48Ryan Holiday?

  Everydane-ness. He says that word, the every, and you're like, yeah, that is, I'm stuck in the everydane-ness of life.

• 53:53Speaker 02

  Yeah. And I think, no, I think it's probably not that book. It might be Confederacy Dungeons. It gave me a lifelong fear of buses. Where I spent a lot of time, because in the fact that in The Moviegoer, he loves his car because it's, it's basically resistant to malaise.

• 54:07Ryan Holiday?

  Yes, yes. Yeah, totally.

• 54:09Speaker 02

  You know, so, and I always think about that when I, you know, but get anything, which is this thing going to be covered in malaise in a couple of years? You know, what's this going to look like on a Sunday afternoon?

• 54:18Ryan Holiday?

  Yeah.

• 54:19Speaker 02

  And that's like a very Walker Percy, he's got a line in there in one of his, but might not, I don't think it's in The Moviegoer. He says, how do you make it through a Wednesday?

• 54:26Ryan Holiday?

  Yeah. It's, and it's weird to have this person. I think one of the other things that's great about that book is like, it feels so modern. Like it's so capturing perfectly the modern moment. And then you're like checking and you're like, 1962 or whatever.

• 54:41Speaker 02

  Dude, I'll tell you, I had this experience in college. This just shows how fucking stupid I am. It was an introductory philosophy class and we read a Kierkegaard book called like On The Current Situation or the, I forget, something like that. And it's like 60, 70 pages and I just, I just, I just connected to it very deeply. And he asked us to guess when it was written. I didn't, and I said, I thought it was written like maybe five, six years ago.

• 55:04Ryan Holiday?

  Right. That's incredible. I mean, when that happens, that's like, I mean, that's my experience. You read Marx's meditations. You're like, this cannot be from a god king 2000 years ago. Like, how could he possibly?

• 55:17Speaker 02

  We think so much of, of what we are dealing with has to do with whatever the current technology is, or the current political scene, or the current this or that. But it's not.

• 55:25Ryan Holiday?

  Yeah.

• 55:26Speaker 02

  All that stuff's just an expression of the deep thing, which doesn't change, you know?

• 55:30Ryan Holiday?

  The malaise, the everydane-ness.

• 55:32Speaker 02

  Yeah.

• 55:32Ryan Holiday?

  The alienation. My kids actually saw an ad for this the other day on YouTube and, um, they asked if we could try it and we did. We had a lot of fun. Whatnot is a totally different platform for buying stuff. It is a live shopping app. It's really fun because I think you want to see who's selling you the stuff. You want to see what they have to say about it. Whatnot is where sellers shine and find their people. Repeat customers that come back to see your face instead of just a logo. Whatnot is the largest dedicated live shopping platform. Beauty, collectibles, electronics, luxury fashion, even cookies. Sellers are building real thriving businesses. Anyone can sell. Your business can be big or small, can be just starting. And people selling on Whatnot sell 10 times more than on other marketplaces.

• 56:16Ryan Holiday?

  Cause you're not just listing products, you're building real connections with buyers. Whatnot users spend something like an hour a day on the app. They're not just browsing, they're engaged, they're buying, they're coming back. You go live, you show up products in real time and you turn what you love into real income. Search Whatnot, W H A T N O T in the app store, download and start selling right away. Violent threats against executives are growing at an alarming rate. When a company experiences backlash, executives are the first people that are blamed. And, uh, people try to track them down through their address, the personal details that are available online. So that backlash can lead right to someone's front door.

• 56:55Ryan Holiday?

  The team at Ironwall knows this better than anyone. They've protected some of the most targeted executives and individuals on the planet for almost two decades. As a white glove enterprise security service, they protect your people with continuous personal data removal, proactive prevention tools and human led emergency support. Someone goes looking for your executives, Ironwall ensures they hit a dead end. So here's what to do. Go to ironwall.com/dailystoic. You fill out a quick form and you can request a free risk assessment. Their team will show you just how exposed your executives are and how to lock it down before the threat reaches their front door. Ironwall.com/dailystoic. Learn how to stop online threats before they become real world attacks. The link is in the show notes.

• 57:38Ryan Holiday?

  And Walker Percy had another thing they love where he's talking about reentry, that life is about reentry.

• 57:44Speaker 02

  Yeah, yes.

• 57:44Ryan Holiday?

  And, and like, I think about that every time I'm like, coming out of a book, like reentry into normal life, where I'm no longer living in this fantasy world.

• 57:53Speaker 02

  Well, I think that Walker Percy thought that his books would change the world in some way.

• 58:02Ryan Holiday?

  Yeah. He saw himself as this kind of philosopher evangelist.

• 58:06Speaker 02

  I think he was depressed that it didn't have the impact he thought it did, but it did.

• 58:09Ryan Holiday?

  Yeah.

• 58:10Speaker 02

  Because that's the thing about a book. Like, look at me, me and you are here sitting, he died, I remember when he died because I was in college.

• 58:15Ryan Holiday?

  Yeah.

• 58:15Speaker 02

  Actually got a book signed by him.

• 58:17Ryan Holiday?

  Cause he was at Loyola when you were doing.

• 58:19Speaker 02

  He, the book Thanatos Syndrome came out and I stood in line at the bookstore that's not there anymore. I forget what it's called in New Orleans. And, um, he signed it and he was, you know, whatever. But I think he thought that he would, you know, he would become a national figure. He would change the world and all this stuff. And he didn't see that happen, but it did.

• 58:40Ryan Holiday?

  Yeah.

• 58:40Speaker 02

  It just happened inside the brains and the heads and sensibilities of thousands and thousands and thousands of people who he helped figure out how to get through life.

• 58:49Ryan Holiday?

  Yeah. I think, I think to go to our point about competition, I got to imagine when he surprise wins the National Book Award, Shelby Foote was both happy and fucking pissed. And then when Shelby Foote became a celebrity in a way that Walker Percy never was through the Ken Burns documentary. Probably the exact same feeling.

• 59:09Speaker 02

  Well, do you know the story? You must know the story about how he won the National Book Award?

• 59:12Ryan Holiday?

  Yeah, wasn't it A.J. Liebling like gave it to his wife or something?

• 59:15Speaker 02

  Yeah, well, what, uh, Gene Stafford, I think. I think what happened is, is Liebling was writing the book about Earl Long in Louisiana. Now, he was writing a New Yorker article. So he said, I want to read everything to his publisher. Give me everything you have.

• 59:28Ryan Holiday?

  Yeah.

• 59:29Speaker 02

  About New Orleans. And The Movie Guard had just come out, published by Knopf.

• 59:32Ryan Holiday?

  Yeah.

• 59:33Speaker 02

  And so they gave him that book.

• 59:34Ryan Holiday?

  And Knopf didn't really like the book, I don't think.

• 59:36Speaker 02

  Well, they let him go.

• 59:37Ryan Holiday?

  Yeah.

• 59:38Speaker 02

  And by the way, this summer, I bought a first edition of The Movie Guard, uh, published by Knopf. I'm never like into, I like, I don't save things. I don't, there were too many great things I had that were destroyed by somebody in my family or given away by my mom for me to think, I'm not going to start collecting things now. It's too late. I've already lost, I had a complete uncut sheet of 1974 Topps baseball cards from the factory and that got given away. So I'm like, I lost that. There's no point, man. But I did, I was very excited to get this first edition of this Knopf. But anyway, he read it and he basically said, this really has nothing to do with what I'm writing about, but this is a great book.

• 1:00:13Ryan Holiday?

  Yeah.

• 1:00:13Speaker 02

  And he gave it to his wife and he won the National Book Award, even though he hadn't been nominated.

• 1:00:17Ryan Holiday?

  Right.

• 1:00:18Speaker 02

  Okay. Which is, by the way, similar to Hemingway. I don't know if you know this story about Hemingway, which is Hemingway, uh, one of his stories was published and they gave it the best American short stories, like the best story of the year, like in 1920, whatever. Even though it wasn't like nominated, it wasn't listed, they did, because it was so outstanding. It was so friggin' great. And the story with Hemingway is he had all these short stories and his wife at the time, you know this story?

• 1:00:45Ryan Holiday?

  She lost him all?

• 1:00:46Speaker 02

  She lost him on the train, which she always thought was intentional. It was some kind of Freudian attempt to kill him.

• 1:00:51Ryan Holiday?

  Yeah.

• 1:00:51Speaker 02

  You know, the only story that survives from that earlier batch, it's like an earlier era. It's like the ancient aliens, man. The only one to survive was the one that won Best American Short Stories because it was out with, you know, being considered.

• 1:01:04Ryan Holiday?

  I told that story in, uh, when I updated, uh, The Obstacle is the Way, because there's this great letter that Hemingway writes to Ezra Pound after. And he's like, I know you're going to tell me it's all for the best, whatever. And he's like, and I know, but I'm not there yet.

• 1:01:18Speaker 02

  Yeah.

• 1:01:19Ryan Holiday?

  And I think that's such a great way of putting it because like, you do know that the devastating breakup or the bankruptcy or the what, you know, this is what humans do. We're going to derive meaning from this. We're going to learn from it. It's, it's going to be in retrospect, part of the trajectory that we couldn't have anticipated. But, but in the moment.

• 1:01:38Speaker 02

  Yeah.

• 1:01:38Ryan Holiday?

  You're like, don't tell me this is all for the best.

• 1:01:41Speaker 02

  Well, it's interesting because I think the story that survived is My Old Man, uh, which is about a jockey's son telling the story of his father's decline.

• 1:01:50Ryan Holiday?

  Yeah.

• 1:01:50Speaker 02

  And it's different.

• 1:01:51Ryan Holiday?

  Yeah.

• 1:01:52Speaker 02

  It's not as severe. It's not as harsh, you know? And that's editing. But another, I don't know if you've had this experience where you lose something and you got to rewrite it. And it is good because basically that's editing, you know? And what's kind of really freaky and, and also reassuring and also, also a little bit depressing is sometimes you rewrite something and you find the original and it's pretty close to the same.

• 1:02:15Ryan Holiday?

  Yes. I had a weird, similar experience. So I, I read Fish that ate the whale when it came out, this hardcover. And then I reread it a couple of years ago. And I was going through, it was fascinating to me to see how I marked several of the same passages.

• 1:02:29Speaker 02

  Yeah.

• 1:02:29Ryan Holiday?

  And, and took an almost identical note.

• 1:02:32Speaker 02

  Yeah. It makes you feel like a machine.

• 1:02:34Ryan Holiday?

  Or, or just like, but it's not like I remembered that that passage was meaningful to me. It's just, it struck me, the same note hit me.

• 1:02:42Speaker 02

  But it's reassuring because you know it's real.

• 1:02:44Ryan Holiday?

  Yes.

• 1:02:45Speaker 02

  It's not just because you had a big lunch. You know what I mean? Or, or you, whatever, you're hungover or something. It's, there's something real about it. And same with the writing. So like one example, people, I, I mentioned On the Road earlier, a book that I really like. And is often derided, but I really like it. By the way, one of the great audiobooks of all time is David Carradine reading On the Road. I don't know if you ever. So, but anyway, the, the thing is always, uh, Truman Capote famously said, that's not writing, it's typing. Because he would say he just wrote in one draft and all that. But if you read about Jack Kerouac, he kept writing the same stories over and over again. And every time he wrote them, he was honing them. That was all, that was, those were rewrites.

• 1:03:23Ryan Holiday?

  Well, the myth is that he wrote that in like 24 hours on some drug binge or whatever. But it, it was actually like, yeah, meticulously edited and rewritten for like months and months and months after.

• 1:03:34Speaker 02

  But even before he wrote that version, he'd written those stories. Oh, and somebody who writes the same stories again and again and again. I know that every time you go back over the same ground, you kind of like, the story becomes tighter and you hone it and you realize what about it makes it work.

• 1:03:47Ryan Holiday?

  Yeah.

• 1:03:48Speaker 02

  And that thing, by the way, that he wrote the books famously on kind of computer paper and it's like a holy scroll.

• 1:03:53Ryan Holiday?

  Yeah.

• 1:03:54Speaker 02

  Actually, one of the weirdest story assignments I ever had for a magazine was to write about Jim Ursay. Remember Jim Ursay? He owned the Colts. He died just a couple of years ago.

• 1:04:03Ryan Holiday?

  He's a drug addict and.

• 1:04:05Speaker 02

  Yeah, he's the only guy I ever interviewed who fell asleep while he was talking.

• 1:04:10Speaker 02

  Creating a very awkward social situation. Like, what do I do? Do I wake him up? Do I quietly leave? You know? So, um, or just wait.

• 1:04:18Ryan Holiday?

  Right.

• 1:04:18Speaker 02

  Anyway, he bought that scroll.

• 1:04:20Ryan Holiday?

  Oh, yeah. He was a weird collector of stuff, right?

• 1:04:23Speaker 02

  Yeah. And he would hire like musicians, like big deal musicians to come to his studio to play with him and he, and he would record. I mean, he was kind of nuts.

• 1:04:30Ryan Holiday?

  Yeah.

• 1:04:31Speaker 02

  And he was another guy who went to my same high school. And his father's super interesting because his father's the one who moved the Baltimore Colts to Indianapolis in the middle of the night. Anyway, got to see that scroll. Which is amazing because it's at the University of Indiana, along with like a first folio of Shakespeare and an early edition of the Bible. It's a crazy collection.

• 1:04:48Ryan Holiday?

  Yeah.

• 1:04:49Speaker 02

  That he gave it to. But it makes you think like, there is something about the physical object that we kind of lose when everything's on computers.

• 1:04:57Ryan Holiday?

  Right.

• 1:04:58Speaker 02

  You know, so we're talking about ambition. So the nature of Jack Kerouac's ambition is captured somehow in the mania of that scroll. And the fact that he did, I always heard, took a lot of Benzer dream to write a bunch of stories he'd been telling for years and years and years. And the Benzer dream was about the art.

• 1:05:15Ryan Holiday?

  Right.

• 1:05:15Speaker 02

  You know what I mean? And I always think about it like, you can't really cheat in art. Like the, like you, you would test him, give him a drug test if you're in the major leagues and say, those home runs don't count.

• 1:05:29Speaker 02

  But they count.

• 1:05:30Ryan Holiday?

  Yes.

• 1:05:30Speaker 02

  Even if he took all the Benzer dream or whatever in the world, the home runs still count in the book.

• 1:05:35Ryan Holiday?

  Yeah. Yeah, there's, uh,

• 1:05:39Ryan Holiday?

  there, there is something to about, was it, was it, uh, Hemingway where he, he wrote this book and then he just like cut the first like two chapters?

• 1:05:47Speaker 02

  Yeah.

• 1:05:47Ryan Holiday?

  Is that in?

• 1:05:48Speaker 02

  Well.

• 1:05:49Ryan Holiday?

  The Sun Also Rises?

• 1:05:49Speaker 02

  No, that's, um, yeah, I think it's, I think it's, I think it's, it's funny because my, my friend, David Lipsky, who's a really great writer.

• 1:05:57Ryan Holiday?

  Yeah.

• 1:05:57Speaker 02

  He always talks about that, which is he opened The Sun Also Rises with a joke about the boxer, I think Benny Leonard. And he had Fitzgerald read it. And Fitzgerald said, oh, that's an old joke. Everybody knows. Get rid of that joke. So he cut the beginning.

• 1:06:13Ryan Holiday?

  Yeah.

• 1:06:13Speaker 02

  So it has this very stark modernist beginning, which hadn't been the beginning. And then Hemingway found out later that he had heard the joke from the same person Fitzgerald heard the joke from. Wasn't an old joke, was just they both had the same friend.

• 1:06:24Ryan Holiday?

  Yes, yes, yes, yes. But, but there's something about like that, that's all gone and yet it's, it's there, it's there. It's, it's under it and there's something powerful about that.

• 1:06:34Speaker 02

  I mean, that's his idea about the iceberg and all that, which he put it, but it's true that like for me, I don't know how you write your books, but my first drafts are like, like the first draft of The Fish that ate the whale was probably like 130,000 words. And the book is probably like 65,000 words.

• 1:06:54Ryan Holiday?

  Yeah.

• 1:06:54Speaker 02

  So that's the kind of thing where it's good to be a little stupid because I've done that with basically every book I've ever written, except for the first couple of books, maybe. If you're aware of that at the time, you realize half of what I'm working, I'm throwing out.

• 1:07:06Ryan Holiday?

  Yeah.

• 1:07:06Speaker 02

  So today's, all today's effort is just nothing. I'm throwing it all out. But of course, you can't think of that when you're writing or you go friggin' nuts. But the, the truth is, it's like censoring people for stuff they say online.

• 1:07:19Ryan Holiday?

  Yeah.

• 1:07:19Speaker 02

  Okay. Which is, maybe they shouldn't be saying it online, but you got to go through the bad stuff to get to the good stuff. Like you have nine bad ideas and one good idea. And then in the book, you just go with the good idea and get rid of the bad ideas. You have to write all the boring parts to get to the interesting parts.

• 1:07:32Ryan Holiday?

  No, it's where you can't think about it because I'm, I'm on the project I'm working on now. It's like, oh, I want to say this. And then so that requires, I don't know, a week of research or find all this stuff. And then I'm trying not to think about the fact that my editor is probably going to tell me to cut it at some point. And like, I have to remember though, it's not actually lost. Like e- even if this paragraph gets distilled down into three words, that's a tag on the end of a sentence or whatever, I earned it. And it, it is there informing my understanding of the subject and the person and all that.

• 1:08:02Speaker 02

  Well, ideally for me, if it's working, you want to be right on the edge.

• 1:08:06Ryan Holiday?

  Yeah.

• 1:08:06Speaker 02

  Okay. But the only way to find the edge is to go over the edge, as Townes Van Zandt taught us. I don't know if you know that story, but, um, do you know that story?

• 1:08:13Ryan Holiday?

  No.

• 1:08:14Speaker 02

  Which is he wanted to, he was on a balcony at a party and he wanted to see how far he could lean back without falling off the balcony. And he realized the only way to really know is to fall off the balcony, which he then did. So.

• 1:08:22Ryan Holiday?

  I was thinking there's a, because there's a great passage in, in Hunter S. Thompson's, uh, Hell's Angels, where he says something very similar about going over the edge on a motorcycle.

• 1:08:29Speaker 02

  Oh yeah, I remember. I just read that recently too. So basically, what I try to do is like, because you get those people in your head, like your editor or imaginary editor, what's going to, so I, each day I try to write something that I think will make my wife guffaw or, or recoil in disgust.

• 1:08:48Ryan Holiday?

  Yeah.

• 1:08:48Speaker 02

  You know, try to get a reaction, you know, like get read on the mood ring.

• 1:08:52Ryan Holiday?

  Yeah.

• 1:08:52Speaker 02

  So it's just a good exercise as a way to keep pushing yourself to what is uncomfortable to say.

• 1:08:57Ryan Holiday?

  Yeah.

• 1:08:58Speaker 02

  You know, and the idea is, you know, most of the writing happens in the rewriting anyway.

• 1:09:04Ryan Holiday?

  Yeah.

• 1:09:04Speaker 02

  So I think the weird thing about a writer is it's like, you're like a sculptor, but you got to like create the block of marble and then carve the statue out of what you created. But the first whole part of it is creating the block of marble.

• 1:09:13Ryan Holiday?

  Right. I ended up putting in this paragraph, I'm writing about this fighter pilot and I was like, I, I found every single pilot from his graduating class that died in an accident and how they died. And so that was like a lot. I had to go through newspaper article after newspaper article and read obituaries and find their gravestones. I'm writing all this stuff and it's like, I, I'm imagining this on the page, just getting an X through it.

• 1:09:37Speaker 02

  Yeah.

• 1:09:37Ryan Holiday?

  And yet I'm informed by the fact that this guy would have been aware of this graveyard of people, these ghosts following him.

• 1:09:48Speaker 02

  Right.

• 1:09:48Ryan Holiday?

  Do you know what I mean?

• 1:09:49Speaker 02

  Yeah. But so a couple of things. One is that kind of thing could be great.

• 1:09:53Ryan Holiday?

  Yeah.

• 1:09:53Speaker 02

  I mean, well, it could be great. It's like, do you ever read the Ian Fraser book, Family?

• 1:09:58Ryan Holiday?

  No.

• 1:09:59Speaker 02

  It's a great book. He's a great writer. He's one of the best writers. And he's got this whole chapter, which was excerpted, I think in The Atlantic, where he goes through every kid in every house on the street that he grew up in and says, what happened to them? And it's like a X-ray of a society, of an American society. It's like, you know, so that that could be like that. I'm saying like, don't be so quick to throw it out because it could be, it's like, when you're talking about the fates of a lot of different people, you're talking about a picture of a whole generation.

• 1:10:27Ryan Holiday?

  Yeah.

• 1:10:27Speaker 02

  The second thing is, this is like a danger when you're a nonfiction writer and you're doing research and you find something really cool.

• 1:10:34Ryan Holiday?

  Yes.

• 1:10:35Speaker 02

  It's very hard to cut. I'm going through that right now.

• 1:10:37Ryan Holiday?

  Yeah.

• 1:10:38Speaker 02

  So it's like, you're kind of like, you're like the dog with the bone. You want to show everybody the bone you got. And it's really hard to cut, man, because it's like, I got something no one else got.

• 1:10:46Ryan Holiday?

  Yeah.

• 1:10:46Speaker 02

  And now I'm just gonna act like that didn't happen. It's like when I'm watching a lot of NHL right now. And you see an incredible play, but nothing results from it. You're like, that's just gone. There's no statistical record. They're not going to show it in a highlight, but it's the best pass I've seen all season.

• 1:11:00Ryan Holiday?

  Right.

• 1:11:00Speaker 02

  And that's kind of like the research that you end up cutting, the, the, those 10 pages that you cut down to a sentence.

• 1:11:05Ryan Holiday?

  And that's why I, I think about that Hemingway thing because he does, he just cuts the chapters whole cloth. But none of the other chapters could have been written without those chapters. It's not like he wrote the book. Then he wrote two prologue chapters and then cut two prologue chapters. Like, it's like, that's the scaffolding and then you remove the scaffolding and the building stands.

• 1:11:27Speaker 02

  I mean, all that's still there. It's like the ghost of it is still there.

• 1:11:30Ryan Holiday?

  Exactly.

• 1:11:30Speaker 02

  And even if you don't read it, you can still feel it. And it's, that's what I mean. Like you gotta go through the bad to get to the good. Like, not that it's bad, but that, you know, behind the story that you're reading is this other story that you feel.

• 1:11:42Ryan Holiday?

  Yes.

• 1:11:43Speaker 02

  And a lot of times you're writing sentences in support of or at the culmination of sentences that you've cut. So literally it's there in the sentence structure. You can feel it.

• 1:11:53Ryan Holiday?

  Right.

• 1:11:53Speaker 02

  I mean, that's all like the nitty gritty of it. And, and it's, and it's really interesting. I really believe in, if you can take a hundred and 20,000 word book and cut it to 60,000 words, ideally whatever power was in that is concentrated.

• 1:12:08Ryan Holiday?

  It's, there's no fat, there's nothing extraneous.

• 1:12:11Speaker 02

  And it's all concentrated.

• 1:12:12Ryan Holiday?

  Yeah.

• 1:12:12Speaker 02

  So I think there was a Hemingway quote, because we're talking about Hemingway, where he talked about wanting to concentrate everything, boil it down to as few sentences as possible. And he said, the only writer that he'd read that was better at that than him was Isaac Babel.

• 1:12:26Speaker 02

  And that's another huge writer for me, which is like Red Cavalry stories. And if you've ever read any of that stuff, it's so fricking intense.

• 1:12:32Ryan Holiday?

  Have you looked at the alternate endings for A Farewell to Arms?

• 1:12:36Speaker 02

  No, I've heard about them.

• 1:12:37Ryan Holiday?

  I bought a copy of that book in an airport in Norway that like, they were clearly trying to like add stuff. So they just, they included all the different paragraphs that he did and like different, there's like ending number, it's got like 30 endings. It's like ending number one, two, three. And you realize just how many directions he tried.

• 1:12:56Speaker 02

  I'm assuming that was published after he died because he would have just never stopped vomiting.

• 1:13:00Ryan Holiday?

  Yeah, but, but you can tell like,

• 1:13:02Speaker 02

  Yeah.

• 1:13:02Ryan Holiday?

  It's, it's like he's, he's riffing all these different notes and trying it. And then he goes with one that's really good, but some of them are close to being as good or better.

• 1:13:12Speaker 02

  The ending is so great.

• 1:13:13Ryan Holiday?

  Yeah.

• 1:13:14Speaker 02

  But I think.

• 1:13:14Ryan Holiday?

  There's just more, like you can tell how he boiled it down to the essence and all this other stuff is there.

• 1:13:20Speaker 02

  Right.

• 1:13:20Ryan Holiday?

  But it wouldn't be there had he not tried these other ways in.

• 1:13:23Speaker 02

  I mean, okay, first of all, you made me think of two, you keep making me think of two things. For some reason, everything you say makes me think of two things. I'm like Jimmy two times.

• 1:13:30Ryan Holiday?

  Yeah.

• 1:13:30Speaker 02

  So the first is again, Ian Frazier, he writes about, and I think his story about Brooklyn, he writes about seeing a page of a book on the beach, like at Coney Island or something. And he picks it up and it's a page from Anna Karenina.

• 1:13:42Ryan Holiday?

  Yeah.

• 1:13:43Speaker 02

  And just a random page because, and he writes that it's a great book. Every page is great. Okay, so I always heard, you'll see how this is connected, that the movie Breathless, you know, the Jean-Luc Godard movie?

• 1:13:55Ryan Holiday?

  Yeah.

• 1:13:56Speaker 02

  It's a great movie, French New Wave. And he turned it in and it was kind of semi-conventional. And it was like, let's say three hours long or something. I, this story might not be true, but it's what I, I'm using it because it's useful as a writer to think about. So the studio said, this story, it has to be 120 minutes or 90 minutes or whatever. And you have to cut and, and he couldn't do it. He just couldn't bring him, couldn't do it.

• 1:14:20Ryan Holiday?

  Yeah.

• 1:14:20Speaker 02

  So he gave it to an editor friend and said, you make the cuts. And the editor cut at random.

• 1:14:26Speaker 02

  Take 10 minutes off here, 10 minutes off here. And it became, this movie's famous for its jump cuts.

• 1:14:30Ryan Holiday?

  Yeah.

• 1:14:31Speaker 02

  Scenes start with no explanation. They start in the middle. And it turns out to be this kind of revolution in how movies are told.

• 1:14:37Ryan Holiday?

  Yeah.

• 1:14:37Speaker 02

  And this movie telling, and it works because the movie's so great.

• 1:14:40Ryan Holiday?

  Right.

• 1:14:41Speaker 02

  That every page is great, like Anna Karenina. You could pick Anna Karenina up at random and start reading it and you wouldn't really need much more than that, you know? So my point is that Hemingway, like in cutting the beginning of Sun Also Rises, even if he started five pages after that, it would have been great.

• 1:14:58Ryan Holiday?

  Right, right. And probably still be great even if you left the two pages.

• 1:15:01Speaker 02

  Yeah.

• 1:15:02Ryan Holiday?

  Or the, the two chapters.

• 1:15:03Speaker 02

  It would have been a very funny joke about Benny Leonard.

• 1:15:04Ryan Holiday?

  Yeah.

• 1:15:05Speaker 02

  The joke which I heard is, how do you beat Benny Leonard? He's such a smart, such a smart fighter. And the, uh, the guy says, yeah, he's such a smart fighter. He's thinking all the time and all the time he's thinking, I'm hitting him in the face.

• 1:15:19Ryan Holiday?

  Yeah, it, it also though, there is something powerful about like, there's something about Hemingway where you think, and this is, I found this on anything that you do that's short, the reader thinks that they're reading quickly and finish it, and they finish it in one sitting or two sittings or whatever, because it's so fucking good. And it's, it's because it's short.

• 1:15:38Speaker 02

  Yeah.

• 1:15:39Ryan Holiday?

  You know what I mean? Like, they're like, oh, I burned through that book. It was incredible. And it's like, you burned through that book because it's half the length of a normal book. That's why you finish it on an airplane because it was finishable on an airplane.

• 1:15:50Speaker 02

  Right.

• 1:15:51Ryan Holiday?

  Like, and, and so there is something just powerful about being short and to the point.

• 1:15:54Speaker 02

  Yeah, well, that's that first story in another country, which, by the way, that book begins, this was a sentence, the first sentence got me. It's something like, I'm quoting from my memory, "In the fall, the war was always there, but we did not go to it anymore." Okay, that's fricking Walker Percy.

• 1:16:07Ryan Holiday?

  Yeah.

• 1:16:08Speaker 02

  That's detachment. That means the entire society is engaged in a war.

• 1:16:13Ryan Holiday?

  Yeah.

• 1:16:13Speaker 02

  And he's been injured out of it.

• 1:16:14Ryan Holiday?

  And they've been going to it over and over and over again, and now he's not.

• 1:16:17Speaker 02

  Right. He's with the, he's with a few other people who are, and by the way, another thing, Hemingway's another person who's a prisoner of his myth.

• 1:16:25Ryan Holiday?

  Yeah.

• 1:16:25Speaker 02

  Which is people have this idea about what he is and it's not what he is at all. Like, it's not what his writing is at all. And in that story is the soldiers about how all the other soldiers were war heroes. And he was a pretend war hero. And when they figured out he was a pretend war hero, like his medals were a joke. He had all these medals, but all they said was, he showed up.

• 1:16:44Ryan Holiday?

  Yeah.

• 1:16:44Speaker 02

  Basically. And there's another guy, the only guy he can be friends with is a guy who was injured before he got to see battle. So he doesn't know if he would be a hero or not. So he could be friends with him. So, but it's, it's super, super interesting. And you also mentioned Hunter Thompson, who, I think I did the last interview with Hunter Thompson. Did you know that?

• 1:17:00Ryan Holiday?

  No.

• 1:17:01Speaker 02

  So, you know, I was at Rolling Stone and Hunter had left Rolling Stone. He was in a kind of a fight with Jan Wenner, who owned Rolling Stone. And Hunter was writing for Vanity Fair, which I had also was writing for.

• 1:17:12Ryan Holiday?

  Yeah.

• 1:17:12Speaker 02

  And Jan, I always thought, wanted to get Hunter in the magazine one way or the other. So he asked me to go out and profile Hunter as he is today. So I went out to Woody Creek, I went out to Aspen, and Hunter was sort of like suspicious because Jan had sent me. I always think it's like in Apocalypse Now, he's like, you're a messenger boy sent by a grossly clerk to collect the bill, you know? But I spent like about a week with him and it was not long before he killed himself. I felt like this was a guy that the myth of him had become so great that it prevented him from functioning.

• 1:17:41Ryan Holiday?

  Yeah.

• 1:17:41Speaker 02

  You know, because he felt, he wasn't selfish enough. He felt like he kind of had to entertain people. And Hemingway writes about this too. About people showing up in Cuba and wanting him to be Hemingway.

• 1:17:52Ryan Holiday?

  Yeah.

• 1:17:52Speaker 02

  And demanding he go out and get drunk with them and go fishing with them. And he just needed to write.

• 1:17:56Ryan Holiday?

  Yeah.

• 1:17:57Speaker 02

  You know, and I really felt that that way about Hunter too. So my point is that when you get down to what makes Hunter great, it's great.

• 1:18:03Ryan Holiday?

  Yeah.

• 1:18:03Speaker 02

  He was a great, great writer.

• 1:18:05Ryan Holiday?

  Yeah.

• 1:18:05Speaker 02

  Whose writing has been obscured by all the sort of fans who want something else from him, which is drugs or something. I always thought the drugs were a weird way to give him complete liberty in writing nonfiction.

• 1:18:15Ryan Holiday?

  Well, I think the drugs ultimately destroy him and the work. I'm forgetting the name, but I have it in there. That, did you read that Tim DeVaney book about Hunter Thompson? It's about him as a political thinker, like a political journalist. And then you're like, when you think about him as the fear and loathing in Las Vegas guy, not the guy writing the best, most insightful political commentary, both, both sort of about America as a whole and the current political landscape of that era.

• 1:18:42Speaker 02

  Right.

• 1:18:43Ryan Holiday?

  And that he was an astute sort of observer and critic of fascism. And the American version of fascism. And then you, you think back and you're like, oh yeah, where does he go? In like, not only is Fear and Loathing in Las Vegas about sort of the emptiness of the American dream, but he goes to that FBI convention.

• 1:18:59Speaker 02

  That's, yeah.

• 1:19:00Ryan Holiday?

  And he's like sort of perfectly caricaturizing that sort of figure of American authority in that time. Those are the people that are, you know, the stooges of J. Edgar Hoover and spying on Martin Luther King Jr. And, you know.

• 1:19:16Speaker 02

  And he had, and he had this, he had the magazine.

• 1:19:19Ryan Holiday?

  Yeah.

• 1:19:20Speaker 02

  That he could write, that would let him do whatever he wanted.

• 1:19:22Ryan Holiday?

  Yeah.

• 1:19:22Speaker 02

  And that's sort of the sadness about the death of magazines in some way. But the thing is like Hunter Thompson, like you're saying, the drugs kind of destroyed him. Like, he felt like he had to deliver Hunter Thompson.

• 1:19:30Ryan Holiday?

  Yeah.

• 1:19:31Speaker 02

  So like a lot of his great things, there's like, the first two pages are all the Hunter Thompson stuff. And then he just gets into writing.

• 1:19:37Ryan Holiday?

  Yes.

• 1:19:37Speaker 02

  And that's where cutting, like the jump cuts is good. Like the, cut the first three pages or whatever.

• 1:19:42Ryan Holiday?

  Yeah.

• 1:19:42Speaker 02

  For me. The book that I like, the first book is the best, which is The Hells Angels.

• 1:19:48Ryan Holiday?

  Incredible book.

• 1:19:50Speaker 02

  And it's, you see where Tom Wolfe must have been hugely influenced by him because they were shared work, they shared material. He gave Tom Wolfe all the stuff, the reporting that became electrocute acid test. He gave him the tapes of The Hells Angels and at Ken Kesey's house.

• 1:20:04Ryan Holiday?

  I had to reread that recently. They, they asked me if I would write a foreword to it and I was like, no. I was like, I'm not remotely qualified to write a foreword to a Tom, a Tom Wolfe book. That seemed insane. But rereading that, it just made, because I know a lot of the people in the sort of psychedelic space now that are like, but now it's like all official and it's about research and healing or whatever. And you're just like, this is the same fucking bullshit clown show as it was, you know, then.

• 1:20:32Speaker 02

  Yeah.

• 1:20:32Ryan Holiday?

  The book held up amazingly well. But no, there's a sentence in, in Hells Angels where he goes, myths and legends die hard in America because they prove to the average person that the tyranny of the rat race is not yet final.

• 1:20:46Speaker 02

  Uh huh.

• 1:20:47Ryan Holiday?

  And then you're like, oh, that's first off, an incredible line. And then it explains, like, why are The Hells Angels famous? Why tough Jews? Why do we, why do we hold up the mafia? Like, why do, why do drug dealers and the storylines and the arcs and the characters we love in rap music? Like, these are horrible people doing horrible things that if they were in your neighborhood or you knew them, you'd be like-

• 1:21:09Speaker 02

  Or you were sitting next to them on a six hour flight.

• 1:21:11Ryan Holiday?

  Yeah, you would want nothing to do with them. These are bad people doing bad things. But from a distance, you know, why do they feel, why do we celebrate those, you know, John Dillinger and stuff? It's because it's like, oh, there's an untraditional path.

• 1:21:25Speaker 02

  Right. Well, it's because they represent kind of an underground.

• 1:21:27Ryan Holiday?

  Yeah.

• 1:21:27Speaker 02

  Which is, everybody's kind of broken into the system and there's no other way. And here's another way.

• 1:21:32Ryan Holiday?

  Yeah.

• 1:21:33Speaker 02

  And it sort of suggests, just knowing it's going on gives you a sense at a distance, like you say, of kind of freedom.

• 1:21:38Ryan Holiday?

  Yeah.

• 1:21:39Speaker 02

  That somebody's not doing it that way.

• 1:21:41Ryan Holiday?

  Yeah. It's beautiful from far away. If you look close.

• 1:21:43Speaker 02

  Yeah.

• 1:21:44Ryan Holiday?

  It's hideous.

• 1:21:44Speaker 02

  Also, a lot of the gangsters, like, because you mentioned tough Jews, they were really, they wanted the status quo. They're all about the status quo because they're getting rich off the status quo.

• 1:21:52Ryan Holiday?

  Yeah.

• 1:21:53Speaker 02

  It's interesting, like The Hells Angels, because that's more pure.

• 1:21:55Ryan Holiday?

  Yeah.

• 1:21:56Speaker 02

  Because that's not, I mean, it becomes a money-making thing, but it starts out as like, and it's again, a PTSD thing.

• 1:22:01Ryan Holiday?

  Yeah.

• 1:22:02Speaker 02

  Which is all these guys that come back from World War II, I think originally, and they don't, they're not quite ready to be Don Draper or whatever. They're not ready to have a nine to five job.

• 1:22:10Ryan Holiday?

  Well, before that, World War I, it's the same, like, you watch Boardwalk Empire and you're like, oh, it's the same.

• 1:22:14Speaker 02

  Well, that's Hemingway too. I mean, that's the whole thing. It's all, they're all veterans trying to get over what happened. So, but I think like the Hunter S. Thompson is, and the Tom Wolfe is, they just, they're kind of opposed to whatever's happening.

• 1:22:27Ryan Holiday?

  Yeah.

• 1:22:28Speaker 02

  Which gives them a way to, to get some distance and to recognize it. So, like, to me, like, the idea of being a writer, the whole idea is to be outside and to see it from a distance and describe it. And so much of, like, a lot of writing now feels like it's all about being inside.

• 1:22:40Ryan Holiday?

  Yeah.

• 1:22:41Speaker 02

  Which is exactly where you don't want to be, man. Is like, it's much easier life, better way to be inside, but you gotta try to get outside. And by the way, you write about things and you think you have one opinion, and then you write about them and your opinion changes by writing about them.

• 1:22:57Ryan Holiday?

  Yeah. If you want to go next door, I got something I want to show you. Some books up.

• 1:23:12Speaker 03

  Talking about guns with others might not always feel comfortable, but it could save a life. Here's a way to start a conversation. Your family is going over to your neighbor's home for dinner for the first time. How would you ask if there are any unlocked guns in the home?

• 1:23:25Speaker 04

  Hey.

• 1:23:26Speaker 03

  Hey, we're so excited for tonight. Before we come over though, may I ask if there are any unlocked guns in your home?

• 1:23:32Speaker 04

  Our guns are stored securely, locked in a safe that the kids can't access.

• 1:23:37Speaker 03

  Awesome. Learn how to have the conversation at agree to agree.org. Brought to you by the Ad Council.