This Conversation Will Make You Rethink Everything You Create | James Altucher (PT. 2)

James Altucher and Ryan return for Part 2 to talk about creativity, aging, and why most ideas don’t last. Ryan explains why he avoids personal stories in his Stoic Virtues series, a research skill he learned while working for Robert Greene, and what most writers get wrong. James opens up about his renewed obsession with an old passion and the painful truth of chasing a past version of yourself. James Altucher is the podcast host of The James Altucher Show , an investor, venture capitalist, writer, and an expert in emerging technologies like crypto and AI. Follow James on Instagram @Altucher and X @JAltucherWatch Ryan's latest interview on The James Altucher Show: https://www.youtube.com/watch?v=cTe49rKcAEA📚 Grab signed copies of James’ book Choose Yourself! at The Painted Porch | https://www.thepaintedporch.com/📖 Preorder the final book in Ryan Holiday's The Stoic Virtues Series: "Wisdom Takes Work": https://store.dailystoic.com/pages/wisdom-takes-work🎙️ Follow The Daily Stoic Podcast on Instagram: https://www.instagram.com/dailystoicpodcast🎥 Watch top moments from The Daily Stoic Podcast on YouTube: https://www.youtube.com/@dailystoicpodcast✉️ Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail🏛 Get Stoic inspired books, medallions, and prints to remember these lessons at the Daily Stoic Store: https://store.dailystoic.com/📱 Follow us: Instagram, Twitter, YouTube, TikTok, and FacebookSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. 📢 Share | ⚙️ Manage Subscription

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

• 0:03Ryan Holiday?

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

• 0:46Ryan Holiday?

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

• 0:54Ryan Holiday?

  Hey, it's Ryan. Welcome to another episode of the Daily Stoic Podcast. So back in 2011, I was thinking about leaving my job. I've talked about this before. Robert Greene gives me the alive time, dead time advice. And I choose it's going to be alive time. I'm really going to work on it. But then I have to sort of stew in those juices. I have to spend six months sort of knowing I'm not going to do this for the rest of my life and I'm about to go off this cliff in not that long from now. And it was a scary time. I told you in the last episode, I showed you this email that I sent to James Altucher. And it's crazy for me to read it back to see that I was saying then that I was anxious and stressed and impatient.

• 1:37Ryan Holiday?

  It's also weird to me that I sent this to like a total stranger, someone I didn't even know, but I just read an article that they'd wrote. And it had struck me. And James's articles are great like that. He has a bunch of articles that I've thought a lot about over the years. And a little lesson as we start today's episode, which is like, when you feel that impulse to... Shoot a note or ask a question. You should do it. I mean, my whole life has been changed by emails like that. It's just a habit I've built. Like, if I have a question, if I like something, I'm concerned about something. If I appreciate something someone's doing and it's helped me, I fire off a note.

• 2:19Ryan Holiday?

  I'll send a DM or an email. I'll find a way to get in touch. And now, look, most of the time, you hear nothing. The vast majority of the time, you hear nothing. But every once in a while, you're back. And that's what I thought was so striking, looking back at this email chain with James Altucher, who's today's guest. We're bringing part two of the episode. I sent it at April 11, 2011, 3:58 PM, and he responded on April 14, 2011, at 4:01 PM. Like, three minutes. And I told him some stuff about American Apparel, and he said, "Seems like you have a lot of great energy and you're an example of why I think most kids should skip the college routine and go straight into getting experience. Good luck on your next endeavor. Let's keep in touch." And now, I'm just looking at my email here.

• 3:00Ryan Holiday?

  I mean, we've got emails, oh, man, like 14 years of emails back and forth. And we worked on all these projects together. I sent guests his podcasts. I advised on his podcasts. He connected me with people. He sent clients to my marketing business. When I did, trust me, I'm lying. My first book came out, we had like a dinner. Someone threw me sort of a book party dinner, and James was there. That was the first time I met him. And we've been friends. Like, we've fallen in and out of touch. We text sometimes. We've spent a lot of time together. And I've been shaped by his work, but I've been shaped by the advice and the thoughts that he gave me. It's been really great, and you never know where these things go. I guess that's what I'm saying. I think people think mentorship is this like official thing.

• 3:45Ryan Holiday?

  "Will you be my mentor?" No, that's not how James shaped or improved my life. It's because I sent him an email and he replied. And then, months later, I sent him another email, and then we bumped into each other. And it develops. It ensues. It's not something you pursue. It's something that ensues, like any good relationships, right? They happen. Slowly over time, that's what they are. And so you never know. And that's why you gotta take the chance. That's why you gotta get them started. Anyways, thanks to James for coming on the podcast. I've been on his podcast many, many times. You can listen to those episodes. He's always been a generous supporter of my work and I try to support his work where I can. I've sent many people his articles over the years. And then we carry Choose Yourself,

• 4:29Ryan Holiday?

  which I think is one of the best self-help books in the genre, certainly over the last 10 years. There's a reason it's sold super well. And he sort of followed his own advice there in that he self-published it and I think made a killing on it. His podcast is big, his email newsletters have been big. He's an investor, venture capitalist, a writer, he's an expert on crypto and AI, and just a person I really like. I always enjoy watching him sort of develop and do stuff over the years. You can follow him on Instagram, at Altucher, on Twitter, Jay Altucher, and grab signed copies of Choose Yourself at the Painted Porch. I'll link to that in today's show notes.

• 5:11Speaker 01

  I would say writing is really hard to do well. And a little bit of the issue right now is everybody thinks they're a writer because you go, oh, I could write something on and put it on LinkedIn. I could actually have AI write it and put it on LinkedIn and now I'm the writer. So, but it's actually really hard to like tell that story. And we see so many different examples. Like, let me ask you. So you write, obviously you write these great, amazing books, bringing Stoicism into the modern day, and you tell it with modern stories, you know, ideas, I always say ideas piggyback on the stories you're telling. And so you have to be a good storyteller, which you are. But you usually use, almost always, I would say, you use his great historical examples that are really

• 5:53Speaker 01

  worth remembering and you tell it in such a way that I remember them. You don't tell as many personal stories. And I'm sure you must have been asked this before, but, and I'm the opposite. I tend, when I write, I tend to write personal stories, some historical, but some are most personal. Why don't you write more? I want to know more personal stories. I really love the personal stories. I know you. I want to hear the personal stories.

• 6:14Ryan Holiday?

  I would say it is deliberate. In some ways, it's cheating because I'm saying, I'm picking, the historical story has a significance and a weight to it that-

• 6:27Speaker 01

  History has chosen those stories for you. It's survivorship bias of story.

• 6:30Ryan Holiday?

  And there's a vague- There's a vague sort of familiarity or myth or significance to it by the fact that it existed, it happened a long time ago, and this person accomplished X, Y, or Z. There's, there's just, I'm starting, I'm standing on the shoulders of giants or something, right? Like I'm pick, and so I think because I'm trying to, I'm already facing a pretty strong headwind, which is that I am trying to persuade people to be interested in an obscure school of ancient philosophy. I'm trying to use every advantage that I can. I always find it super lame when I pick up a book and it starts with, like, so I was consulting with one of my clients, or, you know, I was giving a talk

• 7:13Ryan Holiday?

  to 300 healthcare professionals in Cleveland. I just find it super lame.

• 7:18Speaker 01

  Right. But, but do you find it lame because they're talking to a bunch of pharmacists in Cleveland? Or is it lame because it just might be poor storytelling?

• 7:28Ryan Holiday?

  I think it's both. Like, my last book was about justice, right? Or ethics. Do I want to talk about, you know, me deciding the tip I'm going to leave at this restaurant that I got poor service at? Is that really the, the sort of, the, the raw materials I want to use to have this discussion about how we treat the little guy? Or do I want to pick a story from history where like a great king was-

• 7:54Speaker 01

  That's true.

• 7:54Ryan Holiday?

  You know, so, so I think it mostly has to do with the context in which I'm writing, or what I'm trying to, the idea I'm trying to be in service of. If I'm writing a book about marketing, I put myself in there because I have real experience. I think I have interesting stories.

• 8:08Speaker 01

  Yeah, right. So that is where you did personal stories.

• 8:11Ryan Holiday?

  Yeah. So it just, I think it just, you have to ask yourself, what am I trying to accomplish? And then you think about what's the best means of doing. And this is why ego, I think, is a problem, because if what I really want to do is talk about myself, I'm going to shoehorn myself into things I have no business in being in. Or I'm going to act like my stories are much more interesting than they are. I think I just decided, hey, I'm more interested in these other people for the most part than I am in myself. But I think in your writing, which is much more personal- You you don't just tell your stories aren't, oh, hey, let me tell you about this like

• 8:51Ryan Holiday?

  conversation I had. There it's usually like, let me tell you this moment, my life was falling apart. So there's a vulnerability and rawness to it that doesn't feel like you're trying to make yourself look good.

• 9:04Speaker 01

  Right. If you just say, oh, I'm the greatest basketball player in history, that's going to fail as a story.

• 9:09Ryan Holiday?

  Unless you are the greatest basketball player in history. Yes.

• 9:12Speaker 01

  Right. Otherwise, it's just like bragging. No one wants to listen to that. But I forgot who said, I think Carrie Fisher said, no one wants to watch a movie about beautiful people all the time.

• 9:21Ryan Holiday?

  Yeah.

• 9:21Speaker 01

  So but you're right. It's a smart approach where this historical stories is like a cheat code. So out of like the six or seven billion people who have lived in human history, history itself has chosen the 50 or 60 best stories.

• 9:36Ryan Holiday?

  Yeah.

• 9:36Speaker 01

  And you could just tell those even that have been told many times before, but you could tell it in your own angle. And you know, everyone, you know, you know, let's just take the most obvious story of all, Jesus.

• 9:48Ryan Holiday?

  Yeah.

• 9:49Speaker 01

  We know that billions of people think that this is the best story ever. So if you write about it, you're not gonna, you know that history's already chosen this story for you. Like, it's gonna be good depending on your angle. But whereas if you just write about yourself, like you said, it's a very hit or miss. You've got to be careful and you can have more, you can have more wider range of reaction.

• 10:09Ryan Holiday?

  And I think it's about the medium. When I'm sitting down, and this is my point about books versus some of the other ways, if I'm sitting down and writing a book, that I'm going to try to make a very difficult argument that I want you to pay for and then give hours of your life, I'm going to pick the best, most interesting representations of that idea. If I'm shooting this shit on a podcast, I'll talk about myself. Or if I'm doing a social media video, or if I'm writing an article that I'm going to send out to my emails, those are very different. Do you know what I mean?

• 10:39Speaker 01

  Yeah, like I remember when, when, maybe this was 2016, or it was right before the 2016 election, you wrote an article about you and your dad having a political disagreement. And we did an entire podcast about just that article, because that was important to me, like, or that was interesting. Interesting to me because you're someone I read and pay attention to. And how you dealt with this disagreement with someone very close to you, who you love. That's something that everybody goes through that and it's interesting. And, and so, so I want, as opposed to you writing about, you know, Dwight Eisenhower had a disagreement with his dad and this is how they resolved it. Like some categories are more interesting to be personal.

• 11:19Ryan Holiday?

  No, no. And, and I think I learned from Robert that even when you're picking historical stories, you have to be super selective. And just because you know this one, doesn't mean it's the best one. And so I just try to go like, hey, here's the argument that I'm trying to make. What is the best way to illustrate that or persuade people of that? And you have to sort of do that work. And that's what separates like a okay book from a really good book or a book that lasts and a book that doesn't last.

• 11:48Speaker 01

  I think that's true and it's more particularly interesting now that, because books aren't lasting as long now. Like people don't really read Hemingway anymore for, for pleasure. I mean, I will, but I also grew up on classic books, so maybe that's why. But I feel like the next generation, certainly the generation after that, when it exists, will not read Hemingway as much for pleasure.

• 12:12Ryan Holiday?

  I don't know. I would be curious what the sales say. You know what I mean? Like, I don't know. I, I wouldn't be surprised if they're basically stable.

• 12:19Speaker 01

  Yeah.

• 12:31Speaker 01

  You know, let me ask you a question, like sort of related to what we were just talking about. Is Jesus a Stoic?

• 12:37Ryan Holiday?

  Well, what's interesting is St. Paul, his disciple, studies the Stoics in Tarsus. And then when he gets arrested and he comes before this Roman judge, that judge is Seneca's brother.

• 12:50Speaker 01

  Oh, really?

• 12:51Ryan Holiday?

  Yeah. So these things are like, there's a, I do every Christmas, I do this, um, this email. And I, I go like, he was born in a province of the Roman Empire. You know, he begins to speak, he speaks and writes about philosophy. It reaches, you know, in millions of people. He talks about like loving your brother. He talks about treating people with kindness. He talks about, you know, controlling your desires. He talks, I sort of go through all the, the sort of philosophy of it. And then I go, obviously I'm talking about Jesus, right? He's put to death by the Roman state. He goes bravely. He doesn't hold any gr- and I go, no, actually I'm talking about Seneca. Cause they're born, they have almost the exact same story. They're born in the same year in different parts of the Roman Empire.

• 13:35Ryan Holiday?

  And they, they come at odds with the sort of sovereign power and then are forced, you know, in their dying. They're given this sort of ultimate test of their philosophy, which is like, do they disavow it upon pain of death? And so I, I think what's interesting to me, sort of studying and writing a lot about that period, is it sort of changes my opinion on the Bible. Because, you know, you read the Bible and there's parts of it that make sense and then parts where you're like, what is this? Right? This is weird and strange and why don't they just say what they mean? And, and then if, if that's the only book of ancient literature you know, you could go, oh, that's just how they were back then.

• 14:15Ryan Holiday?

  And then you read Seneca or any of the Stoics or Socrates, and they're just normal people talking about regular life. They're not speaking in riddles. They don't claim to hear voices, you know, they're, and you go, oh, actually like Jesus was weird. And it's very discordant. It makes it harder for me to appreciate that message in some ways. In other ways, I appreciate it more, but this isn't the only philosopher talking about this stuff. There were other people.

• 14:46Speaker 01

  Right.

• 14:47Ryan Holiday?

  Who are much more accessible, much less mystical, maybe even more helpful to people. And we just went, we went with this other myth instead. I've always found that strange.

• 15:02Speaker 01

  I wonder if it's because back then Stoicism to let's say, what was the Greek religion, but we now call Greek mythology. There was a distance of many centuries from the beginnings of the Greek religion to Stoicism. So maybe people were kind of like, okay, those are good stories, but what else? And I feel like now in modern society, now of course there are very, there are a lot of literalists who take the Bible literally. But probably most people are secular and. They believe in turn the other cheek, but they don't necessarily believe in every miracle and so on. So I wonder if now we're at that point where religion needs to be more philosophical because it's hard to take it literally. And maybe back in 0 AD, people like Seneca were similarly,

• 15:46Speaker 01

  okay, well, obviously Zeus doesn't create all lightning storms and I need to understand what the actual philosophy is here.

• 15:54Ryan Holiday?

  Well, it's also weird. So Hadrian has this like boyfriend lover who drowns in the like the Nile River or something, right? And he's so bereft and, and full of grief that he like sets up this temple and this cult to his, he like anoints him as a god and they set up this cult that worships like his dead boyfriend. And it becomes like enormously popular, like rivaling Christianity in the early days.

• 16:20Speaker 01

  Well, who was it? I never even heard of it.

• 16:22Ryan Holiday?

  I'm forgetting his name. But yeah, the point is you've never even heard of it. This was just like a thing that happened, which is like these different cults or different sort of adherents to these different deities or figures would sort of take on popularity. And then some of them kept going and some of them didn't. And so I always think that's interesting that like we just sort of choose which ones thousands of years later, it seems like it all makes sense. But at some point, it was kind of a new thing.

• 16:51Speaker 01

  Yeah. And it'd be interesting to see what, why different things survive. Like, why did, why did Judaism and then Judeo-Christianism survive?

• 17:00Ryan Holiday?

  Yeah.

• 17:00Speaker 01

  Like, it was just, Israelites were just one tribe of people in Israel and they were all just like fighting it out.

• 17:07Ryan Holiday?

  Yeah.

• 17:07Speaker 01

  And I guess around 900 B.C., for a brief period, for several hundred years, the Israelites won. They won all the battles, killed all the other people. And then they wrote down their, about their gods. And that's the one, then they were invaded and only one small group, the Judea, the Jews, lived and survived and organized. And somehow that group

• 17:31Speaker 01

  Became everything.

• 17:32Ryan Holiday?

  Yes.

• 17:32Speaker 01

  And so it's, it's interesting. And like you say, though, every tribe, there's thousands of tribes that we never know about again.

• 17:39Ryan Holiday?

  Yes.

• 17:39Speaker 01

  So like, what happened?

• 17:41Ryan Holiday?

  Or, or like, the Odyssey is the myth that survived, right? Somebody wrote that one down. It was an oral tradition that somebody wrote down. And then it's not just that they wrote it down and it survived. It maintained its popularity for 2,000, 2,500 years or whatever, right? Like, we only discovered Gilgamesh, which is a similar epic myth, also really interesting, also a foundational cultural idea for a group of people. But it was basically lost until the 1850s. So it's only had 150, it's not that it's however old that it is. It's however old it is and has remained in circulation. Right? So it's, it's that we've been telling and retell, like, Matt Damon's gonna star on The Odyssey and Christopher Nolan's making-

• 18:24Speaker 01

  It's a bad choice. Christopher Nolan is great, but okay.

• 18:27Ryan Holiday?

  But you know what? Like, then there was a, like, Ralph Fiennes is, is also in a movie about Odysseus that is coming out. Like, we've just been retelling this story for thousands of years in every medium possible, right? And so it's not that it's old, it's that it's perpetually made new that's made it so powerful. Whereas Gilgamesh, for 2,000 of the years, was obscured and unknown. And then for the last 150 years, some people have been reading it.

• 18:58Speaker 01

  I mean, I would say Gilgamesh, Gilgamesh is less a story about survival than, you know, Odysseus and, and Jesus and Buddha and, you know-

• 19:10Ryan Holiday?

  It's still the hero's journey. I'm just saying.

• 19:11Speaker 01

  Yeah.

• 19:12Ryan Holiday?

  But it, but what I'm saying is that because schoolchildren weren't taught Gilgamesh from the year one to the year 1850.

• 19:22Speaker 01

  Yeah.

• 19:22Ryan Holiday?

  Is why it's not as culturally salient. It's not that it's better or worse. It's just, it wasn't told and retold and retold and told and retold and reinterpreted and mean something new to each generation. It missed 18 generations.

• 19:37Speaker 01

  But then I see, so then you take your books on Stoicism. They are using this idea of what you just described, which is, okay, how do I take this beautiful philosophy that you personally believe in and bring it into a modern context? So perhaps it is taught and so that it does at least bridge from this generation to the next. And you so you tell these modern stories like here's Harry Truman, here's, you know, John McCain and you kind of, and by the way, which are good choices because you have Democrats, Republicans, you're kind of neutral there. And you bring these stories together to tell this, to tell, talk about this philosophy, which really is a modern philosophy. It just previously has been told in these ancient ways.

• 20:21Speaker 01

  Like it's not that obscure, the idea of being a virtuous person and overcoming hardship and, and, you know, doing these, but let's, let's stop saying it in terms of Socrates, you know, taking hemlock and let's put it in terms of, you know, a prisoner of war in the, in the Korean War and so on.

• 20:38Ryan Holiday?

  Yeah, I'm trying to take the ideas and illustrate them and demonstrate them and put them up for discussion, which is what philosophy is supposed to be, but sort of isn't anymore. And so, yeah, you're supposed to agree with some of the stories, disagree about some of the stories, raise different questions, or what about this? Or, you know, okay, Rockefeller is interesting here, but isn't he also a shitty person? Like that's part, it's supposed to generate those kinds of questions. It's not supposed to be definitive.

• 21:07Speaker 01

  Which Robert Greene is like such an expert at, like, because he'll take all these historical stories, some you know, some you don't. And when you don't know them, you're like, oh my God, Shi Shu was the empress of China in 400 B.C. Like it was a war. And like, you know, like all these stories that are, so you get this sense that he is... Such an amazing historian, but then he's bringing into these discussing these laws of power. But then there's the opposite side of each story, like the opposite of each law of power, which also could apply. It's just a, his books are genius.

• 21:39Ryan Holiday?

  Well, the big breakthrough moment for me when I was Robert Green's research assistant is, is so he talks a lot in the 48 Laws of Power about the Peloponnesian War and what predates it, obviously. I was curious, he has this great chapter in the 48 Laws of Power on the Battle of Marathon. And I, so I messaged him, or I saw him one day and I said, Robert, what book did you read to write about the Battle of Marathon? And he recommended some book by some academic. And I went and I read it. And so I read his thing. And then I went and I read this, you know, big book about, when I finished it, I was, I saw what he did. Like, I saw how this book became these pages. And like Brian Koppelman talks

• 22:22Ryan Holiday?

  about like the moment, like the moment you realize you can do it, or how it works. That was just like a huge breakthrough moment in my career and my understanding of sort of history and writing, where I saw the finished product, and then the source material. And I, I just realized like, oh, that's a, that's, that's the magic trick. It's not actually magic. This is how the magician does it.

• 22:48Speaker 01

  So, so what, what was the bridge between the source and?

• 22:51Ryan Holiday?

  I did like, I think there was even, oh, I saw how like these five sentences became one sentence. Or that Robert read this, like this academic studied this thing for 30 years. And Robert Green read it and realized that the critic, like he distilled it all down to the, he took, he had a take on what this guy's sort of historical explanation. And Robert reduced it all down to this very specific lesson. And then he used the raw materials to, to tell that story in a way that demonstrates that lesson in a couple paragraphs. And that's basically the same magic trick that I do in my books. I read, you know, I, I have a story about Lincoln in my new book. And I thought I'd already read a lot about Lincoln.

• 23:35Ryan Holiday?

  And I went down to write it and I realized it didn't have the material that I needed. And so I went and I, I probably cumulatively read 10,000 pages on Lincoln. And that is maybe a 7,000 word chapter in the book. And so

• 23:54Speaker 01

  This coming book, this next book.

• 23:55Ryan Holiday?

  Yeah. So 10,000 pages to 7,000 words. That's

• 24:00Speaker 01

  7,000 words is still a lot. I mean, that's 20 pages or

• 24:02Ryan Holiday?

  Longer than I normally do. But yeah, the, the process of going, like, I stacked all the books up. It's like taller than me, like from the floor to my, much taller than me. And what I was looking for is the, the, the sort of essence of like, not Lincoln, every biographical detail and every place and thing that he ever said. But the argument I was making about Lincoln as this sort of man who fused both sort of pragmatism and wisdom and understanding of human nature with also this sort of aspiration, this sort of belief in something better. That's what I was trying to get at, and I had to go consume all this material

• 24:42Ryan Holiday?

  to get the pieces that I wanted to make to portray, to, to take the reader on a journey from here to here. And reading this book from, that Robert recommended and seeing that that's how it became two paragraphs. I just did some, that's what I do every day is I am reading and finding and developing stuff. And then, you know, trying to put it in some form or some story. But that's the magic trick.

• 25:09Speaker 01

  And, and it's not that easy because you always have to have a unique take.

• 25:14Ryan Holiday?

  Yeah.

• 25:14Speaker 01

  Like if it's not unique, then don't, then no one should read your book.

• 25:18Ryan Holiday?

  Sure.

• 25:18Speaker 01

  So like, and, and Robert does it very well. You do that very well. It's, it's even though it's a cheat code to take these historical stories that have survived. It's to turn it into your own story about this person is still very, a difficult skill.

• 25:33Ryan Holiday?

  Well, every writer or every sort of filmmaker or whatever has like their sort of thing. Like it's very clear to me that what Michael Lewis does is he finds characters. Like he wants to write about the financial crisis, but he doesn't sit down and tell you about the financial crisis. He finds a handful of weirdos.

• 25:52Speaker 01

  Yeah.

• 25:52Ryan Holiday?

  Who are his way in, or he doesn't want to talk about a pandemic. He talks about, you know, a bunch of different public health officials, or he wants to talk about bureaucrats and he finds, it's very clear that he must go look. He has an idea for a story he wants to tell. And then he doesn't start until he finds the people. Right. And you have to, so that's his thing. He's a character driven. His magic trick is he finds a group of people who you and I would probably not Think are that interesting.

• 26:22Speaker 01

  Yeah.

• 26:22Ryan Holiday?

  Or pass right over. His, his skill, what he's honed over tens of thousands of hours is like, he can identify who those characters is. He wants to talk about football. He finds the story of the, the blindside kid, this, you know, uh, and, and how that position in football explains everything. And, and that's his genius. Malcolm Gladwell is, you know, he finds sort of counterintuitive scientific research and then he finds stories that illustrates the, but, but every person kind of has their thing.

• 26:54Speaker 01

  Michael Lewis is interesting because his first book, which arguably might be his best book, it's hard to.

• 26:59Ryan Holiday?

  Yes.

• 27:00Speaker 01

  Decide, but I loved his first book, Liar's Poker is about him. That is the personal story.

• 27:04Ryan Holiday?

  Yes, it's less character driven, but all the other guys are these weird maniacs.

• 27:09Speaker 01

  Yeah.

• 27:09Ryan Holiday?

  He's, yes, he's more of a character in that book, but he's kind of the, he's more the Nick Carraway of that book. He's not actually like, Nick Carraway is not the main character of The Great Gatsby. He's looking up at Gatsby and that's what Liar's Poker is.

• 27:23Speaker 01

  Yeah, that's true. I enjoyed Liar's Poker, but it inspired a generation of people to like work on Wall Street.

• 27:29Ryan Holiday?

  To do the opposite of what he was trying to say.

• 27:31Speaker 01

  Yeah. Even though he portrays the worst kind of world in Liar's Poker, it's like, everyone reads that, then that's it. I'm working on Wall Street.

• 27:37Ryan Holiday?

  I gave a talk at this thing yesterday and this guy came up to me and he was like, I read your book, Trust Me, I'm Lying. It's changed my life. It's why I got into marketing. And I was just like, that, that exact thing, like the opposite of what I was trying to do in that book.

• 27:52Speaker 01

  Well, that, I guess it's because A, it's a fascinating world and subculture. Like all of these books also, their characters exist in cultures.

• 28:02Ryan Holiday?

  Sure.

• 28:02Speaker 01

  But really more in subcultures, which exist in cultures.

• 28:04Ryan Holiday?

  Yeah.

• 28:04Speaker 01

  And so the Trust Me, I'm Lying describes this magic. So this is, it's your first book, right? Trust Me, I'm Lying. I mean, it just came, that's how I met you.

• 28:13Ryan Holiday?

  Yeah. You were at, you were at, we had a dinner for that.

• 28:16Speaker 01

  Yeah. The dinner for the day was book was published or the week the book was published. And I remember you, I was sitting next to you, said to me, it's, and you said to me about my writing. You said, it's like you came out of nowhere. You just started writing and I, and I felt it was like you, you came out of nowhere because it was your first book that just was getting published. So Trust Me, I'm Lying also portrays this subculture of marketing where there is this group of guys, like, like what you started out as an 18 year old, who somehow know, or are creative enough to figure out these tricks almost to. You know, inspire thousands or millions of people to do something. Oh, I'm gonna buy an American Apparel shirt. Or I'm gonna buy, you know, Tucker's book or whatever. So all the fascinating stuff you've worked on.

• 29:13Ryan Holiday?

  So are you gonna do one more book, you think?

• 29:15Speaker 01

  Well, OK, here's a question. This is, you know, I remember I was talking to Robert Greene and I was describing offline something I was doing and he's like, oh, my gosh, this is the best book. You've got to write this book. And but now I'm having a problem. I was gonna ask you your advice. So I was good at something as a kid and I stopped doing that thing for 30 years almost. And now I'm trying to be good as an adult. So it's chess. I was a chess master as a kid.

• 29:40Ryan Holiday?

  Chess, right?

• 29:40Speaker 01

  Yeah. And I stopped playing for 30 years. And during that 30 years, I became successful in a lot of other ways. And but of course, if you're not doing something at all, you lose ability. And it's a very hard game. Like, it requires thousands of hours of discipline to even get as good as I was, let alone someone who's a professional player. But I'm trying now to get the same kind of ranking that I had back then. And you would think it doesn't matter your age.

• 30:07Ryan Holiday?

  Yeah.

• 30:07Speaker 01

  But somehow, it does.

• 30:10Ryan Holiday?

  Sure.

• 30:10Speaker 01

  And and the interesting thing is, because I've now had success in other areas and my life has built up, OK, now I could have, I've had, you know, dinner with Magnus Carlsen. I've been friends with Garry Kasparov, like, all these people who are my heroes.

• 30:26Ryan Holiday?

  Yeah.

• 30:26Speaker 01

  You know, all throughout, I could be part of their culture in ways that I couldn't as a kid. But at the same time, I'm just not, no matter how much I study, discipline myself, you know, work on this, get advice from people like Carlsen or Carlsen's coach or whoever, it doesn't seem like I'm gonna be able to achieve.

• 30:46Ryan Holiday?

  That seems like that should be the book. If the book ends with you becoming a great flawless chess player who like, I don't even know if people would believe it. I think it should be, there's something about the struggle and then ultimately the falling short and the sort of bittersweetness of you got as close as you could, but some moments are lost forever. I think that's the struggle and the relatability and the essence of the book. Do you know what I mean? If you could just... Stop what you're doing and become an Olympic swimmer at age 70. Like, who's actually gonna do that and who actually could do that? Like, it doesn't, the coming back to the thing that you used to love and getting really good at it and learning from it,

• 31:26Ryan Holiday?

  but also the pain of having lost 30 years of it and the new appreciation. All, that's all what makes it relatable. Cause most people can't just go back and give everything to an old hobby anyway. Do you know what I mean? I think part, that, that should be part of it. I do have, sometimes.

• 31:43Speaker 01

  And that's, that's what the second, next time, the very next time I spoke to Robert Greene after that, he said, you gotta write a book. I said, I can't, I have no ending for this book. I, I failed.

• 31:52Ryan Holiday?

  Yeah.

• 31:52Speaker 01

  And he's like, are you, you know, you can imagine the way he talks. He's like, are you kidding me? You know, you did it. What are you gonna be like back to turn, turn yourself back to an 18 year old again? Of course not. You did it, but I don't really know what that means.

• 32:06Ryan Holiday?

  No, no, I think that is the ending. The ending is life, not a story, you know, not a Disney movie.

• 32:12Speaker 01

  Yeah.

• 32:13Ryan Holiday?

  Sometimes I feel like when you're working on a project, you need like a, you need a comp title. You need something that's like similar, but it's different enough that it doesn't feel like somebody already did it. There's this historian, her name is Nell Painter. And she's a great, she's a historian of like sort of African American life. And anyway, she wrote this book called Old in Art School about her af, she's like the peak of her profession. She's done everything you could. She could just sort of live out her life as a, you know, as just a professor emeritus, uh, you know, sort of person. And instead she retires as a historian and she goes back to art school. And the book's called Old in Art School. And it's about her doing something similar to chess, but also different than chess. And like, what, what makes a good painter, right?

• 32:58Ryan Holiday?

  Like, but she's deciding not just to be an old person who paints for fun, but to like be rigorous and serious about the thing and to go back and get the education and the basis and the skills that she never seriously pursued before. And then to also, you know, be humbled by the fact that she's this established person, starting over as a beginner in a new. Field and it's a really interesting book. I think you would like it.

• 33:25Speaker 01

  I'm definitely going to read it. But what's interesting to me there too, is that she put the word old in the title.

• 33:31Ryan Holiday?

  Yeah.

• 33:31Speaker 01

  So I never realized I was, I always have thought I was young. I always think of myself as, that's why I would go up in a comedy club. I didn't even think twice about starting to do stand up comedy, even though it's a young person's game.

• 33:43Ryan Holiday?

  Sure.

• 33:43Speaker 01

  But somehow doing it in the past few years, doing this chest up, I realized, oh, this is the problem. I'm old.

• 33:52Ryan Holiday?

  Yes.

• 33:52Speaker 01

  Like they're young and I'm old. And that's actually the main problem. It's like if I was trying to play basketball again or something like, oh, I can't do it. I can't jump. So.

• 34:02Ryan Holiday?

  Well, like when I met you, I was a kid, right? And I was like, that was a big, my identity was partly rooted in the fact that I was always the youngest person in every room. And now I have some gray hairs and I'm not, and I've been doing this thing a long time. And yeah, you're, you just realize you sort of take for granted parts of your identity that are actually not stable, that they're changing and the world is changing around you. And that's, I think that's a, think about how much, how relatable that is though, for the reader, because.

• 34:32Speaker 01

  Really good point.

• 34:33Ryan Holiday?

  You're, everyone is, most people reading your book are old in the sense that they're not 20.

• 34:38Speaker 01

  Yeah.

• 34:39Ryan Holiday?

  Right? They're going to be, they're having some reckoning with that. Like LeBron James is like one of the last athletes that started when I was a kid. You know what I mean? And like, so there's this part of life where just all the things from a period in your life, they seem stable, but actually day to day, they're dying and falling off. And then you have these sort of wake up call moments and you go, oh, that's like Seneca tells this story about returning to his childhood estate. And you know, it's in terrible shape. Like these trees are dying and he's about to, he calls up the overseer and he's, you know, you're not taking care of this place.

• 35:21Ryan Holiday?

  What it, you know, and the overseer is like, do you not recognize me? Like I was a kid when you were a kid here. We're both old now. And he's like, these trees are dying, not because they're not taken care of. They're dying of old age. This is how the lifespan of these trees. And it's in this moment that Seneca realizes he's old and the same process is happening to him. I just had the same experience. I checked into this hotel in Boulder that I realized I gave one of my first ever talks to. And I didn't realize that till I was walking down the hall. And the first thought I had is this hotel is really going to shit. And then I realized, no, this hotel was nice when I was here last.

• 36:06Ryan Holiday?

  And it's been 15 years. Like, and, and then I thought, oh, like, I'm beat to shit too. You know, like-

• 36:13Speaker 01

  That, that is the experience like, and I had never felt that before. It really was a wake up call, like in every way, like the way my brain works, the way my health works, my response to winning or losing, like everything has aged.

• 36:28Ryan Holiday?

  Yeah.

• 36:28Speaker 01

  And I never had that experience before. I never, I always felt like, oh, I've avoided aging.

• 36:33Ryan Holiday?

  Yeah.

• 36:33Speaker 01

  Somehow. And now I realized, A, everyone's younger.

• 36:39Ryan Holiday?

  Yeah.

• 36:39Speaker 01

  And B, oh, I just made a move. I remember thinking when I was a kid playing my dad, oh, this is, I would think he just made an old man move. Now I just made that same type of move.

• 36:51Ryan Holiday?

  Yes.

• 36:52Speaker 01

  And it's just gross.

• 36:53Ryan Holiday?

  Yeah.

• 36:54Speaker 01

  But at the same time, it's like, okay, well, what do I do to stop it? I'm gonna stop, completely stop drinking alcohol. That'll help. I'm gonna make sure I sleep eight hours a day and follow all the Andrew Huberman advice about sleeping eight hours a day. I'm gonna, you know, work out more. I'm gonna be more disciplined about studying and, and, you know, the types of games I play and tournament selection. And so you do all these things because you're older, but it's still, and you know more, but it still doesn't help.

• 37:23Ryan Holiday?

  Yeah, you're just arresting the decline. You're not, you can't actually get back. You can just slow the process. And yeah, realizing that you used to be able to get away with not bringing a hundred percent of yourself to something. And then now- You, if you're not at your A game, you suck.

• 37:42Speaker 01

  Yeah, and they, and they all know that, right? Cause it's a very competitive game and so it's a safe way to practice war. So, and these younger people are, they will kill you in an alley, like if they could. So it's like they know, oh, just keep this guy going till the fourth hour of play.

• 37:59Ryan Holiday?

  And he's just gonna Fall apart.

• 38:00Speaker 01

  Yeah, which is what happens.

• 38:02Ryan Holiday?

  Yeah.

• 38:02Speaker 01

  So unless I win, I mean, I'm not, I'm not saying I'm horrible. I'm just saying I can't get back to where I was.

• 38:07Ryan Holiday?

  No, you have to have a certain amount of self-awareness about this. Or, I mean, obviously this is what we just went through with the last president. If you're not aware of your decline as it's happening and you're not able to mitigate it and you're not able to compensate for it and you're not able to ultimately know what your limitations are, you'll find yourself in an impossible situation.

• 38:26Speaker 01

  And, and you also have to know what sort of areas of life benefit with age as opposed to decline. Cause I would say most things decline, but for instance, I was talking to Arthur Brooks who's written a lot about this topic. The peak age, of course, for mathematicians in their twenties, like 25 years old, but the peak age for historian is 69 years old.

• 38:44Ryan Holiday?

  Right.

• 38:44Speaker 01

  Because they've

• 38:46Ryan Holiday?

  You've lived through history now.

• 38:47Speaker 01

  Yeah, you've lived through history and you know how to like, you don't have to come up with original ideas, but you're really good at connecting old ideas. So you could say, oh, this experience in COVID is like this other experience during the Great Depression.

• 39:00Ryan Holiday?

  Yeah.

• 39:00Speaker 01

  So younger people can't synthesize these ideas.

• 39:02Ryan Holiday?

  Larger cumulative base of not, you have these sort of cumulative advantages in some ways, and then you have cumulative disadvantages in the sense that you're tired, your eyes hurt more, you know, whatever. You have, you have to figure out where that advantage, it's like, like musicians, you become less cool as you get older, but you actually become probably a better performer because you've done it longer.

• 39:25Speaker 01

  Well, okay, why with every band though, like let's just take Led Zeppelin or the Beatles or, I mean, and they're like among the two Judas priests, let's take them.

• 39:33Ryan Holiday?

  I just saw them a couple of weeks, a month ago.

• 39:35Speaker 01

  Really?

• 39:35Ryan Holiday?

  Yeah.

• 39:35Speaker 01

  But okay, they're playing their songs from the 1970s, right? Cause that every band, it seems, has their five year window where they're amazing. They're the best in the world. And then they're never again able to write a, even one song.

• 39:49Ryan Holiday?

  Well, that's what I mean. I think creatively, being a musician is not just writing songs. It's also performing songs.

• 39:56Speaker 01

  Yeah.

• 39:56Ryan Holiday?

  Right? And so this, it's like, maybe their, their window, which isn't just raw skill. It's also what culturally you're allowed, you know, you only have this sort of cultural window also. It's not like if we, if we suddenly decided to value older musicians, they have hits. It's that we don't, right?

• 40:13Speaker 01

  I wonder if that's true, cause again, I don't, I just don't like, I mean, if Led Zeppelin tried to make a new song now, I probably wouldn't like it. Whereas I love.

• 40:19Ryan Holiday?

  I, I think it's both, but I guess my, my point is they might be less great at writing new songs. But they also now have three decades or four decades of performing the song. And so the show is incredible.

• 40:31Speaker 01

  Yeah.

• 40:31Ryan Holiday?

  You know, and so what, what are you optimizing for? You optimizing for the thing that you're, you know, a game you're likely, unlikely to win? Or are you optimizing for the performance, which is less sort of age sensitive?

• 40:44Speaker 01

  Yeah. So I guess like the advice to me is how do I optimize? You know, my experience now involving this incredible activity, given my age, given my, you know, that I probably can't achieve the goals I want to get, but what can I optimize in it? And in terms of telling the story.

• 41:03Ryan Holiday?

  And I think also the question is, do you love playing? Do you love being a chess player or do you love chess? And you know, and so like in sports, it's like, do you love the game of basketball? Or do you love being the star point guard? And those are very different things. And if you, what you actually love is like the sound of sneakers on the floor and the smell of the locker room and the cheer of the crowd and the strategy and the grind. If you love that, there's lots of ways you can participate. You can participate until the day you die. If you love something else about it, if you love it for more narcissistic reasons, then you only have your very brief playing window.

• 41:43Speaker 01

  The problem, like, let's put it in a musician sense. Some people, some musicians might like, oh, I like making a platinum album. Sure. And other musicians might like the whole music thing. Like, like, writing is a really good thing because you could always enjoy writing, reading, putting it, putting together new stories. I feel like writers never wear out. And that's, you know, I'm oversimplifying, but, but like, yeah, with something that's competitive, like, take basketball sport, I don't play, but like, Michael Jordan, he clearly loved winning. It's painful to lose. Any competitive sport or game is, it's really painful to lose, no matter how much you love it. So, Michael Jordan, although he managed to convert that into owning a team, and he

• 42:25Speaker 01

  did play probably a few more years, more than he would have liked, but it's painful to lose. Here, we need to go in the bookstore because I want to show you a book related to this exact thing. Oh, did we do the podcast? Yeah, this is the podcast. Yeah, yeah.

• 42:42Speaker 01

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