Episode 4: Ryan Holiday

This episode features Ryan Holiday, who became Director of Marketing at American Apparel at age 21 (!). Since dropping out of college at 19 to apprentice under the strategist Robert Greene, Ryan has advised many bestselling authors (including yours truly) and multi-platinum musicians. He is master of the media, and he knows how to both build massive buzz and respond to unexpected crises. I hired him to help with the launches of The 4-Hour Body and The 4-Hour Chef, and his unorthodox approaches always impress. He takes the paths less traveled. In this episode, we discuss dozens of topics, including the real-world strategies he uses to thrive (not just survive) when the world is exploding around him. Enjoy!

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

• 0:00Tim Ferriss?

  Good morning, afternoon, and evening, you sexy little people, and even you large people out there. This is the Tim Ferriss Show. In this episode, I will be having a long discussion, and I hope it is an interesting discussion with Ryan Holiday. I've known Ryan Holiday for quite a time now, since 2007, South by Southwest. That is when we first met. And he has helped me with a number of my book launches, including The Four Hour Body, and quite a lot of The Four Hour Chef. He is very, very clever, very unorthodox, and he got an early start. He is known as a media strategist for controversial clients like Tucker Maxx, bestselling author, and founder of American Apparel, Dove Charney. He dropped out of college at 19 to apprentice under Robert Greene, known for The Forty

• 0:44Tim Ferriss?

  Eight Laws of Power and other bestselling books, went on to advise many other authors, multi-platinum musicians. He is director of marketing at American Apparel, where his work has been profiled all over the place, and he's had to deal with everything from lawsuits, scandals, huge opportunities, and everything in between. His strategies and approaches in handling good and bad situations have been used as case studies by Twitter, YouTube, Google, on and on and on and on. He is a good friend, very smart, very in control. We'll delve into tactics, philosophy, his new book, and much, much more. I hope you enjoy it, and thank you for listening.

• 1:46Tim Ferriss?

  So Ryan, to start off, I suppose, we could talk about our mutual love of Stoicism, and how we both fell into the throes of philosophy. But for many people, I think they, number one, don't know perhaps the origins of how you encountered Stoicism. And I remember one of your friends, one of our mutual friends, telling me about how you were one of the odd ducks out who was fascinated by Stoicism in high school. I think that is part of the story, but maybe you could give us a little bit of background on how you ended up encountering all of these various characters historically, and getting into it.

• 2:24Ryan Holiday?

  Yeah, it was weird. It actually wasn't high school. I was in college. I was writing for a newspaper and I got sent to this conference that Dr. Drew Pinsky, like he has a show on HLN, he's the host of Love Line. He was like leading this private session with college journalists about. And I was, so I sit through the whole thing and then after I walk up to him and I don't know what possessed me to do this, but I asked him if he had any books that he would recommend. Cause he seemed like a very smart person who read a lot. And he was like, you know, I'm reading this, this book about this philosopher named Epictetus. Uh, it's a philosophy known as Stoicism. I think it's really good and you should check it out. Um, and so I, I went and I, you know, I bought it on Amazon. I still have like the Amazon receipts.

• 3:06Ryan Holiday?

  So this would have been like 2006. Um, so I bought it and then I bought this other book, um, called The Meditations of Marcus Aurelius, which Amazon like suggested, you know, and they, they link purchases. And the Marcus Aurelius, this was before Amazon Prime. So Marcus Aurelius comes first. Um, and I sit down and I read it and it just, you know, totally blows my mind in the way that like a, a book can blow the mind of a 19 year old, uh, boy, I guess. Um, Ty, Ty, Tyler Cowen calls them like quake books, like books that sort of shake everything. And it, it was that for me. It was like this book that totally turned my whole life upside down. And at the time I'd been, I would, I just got dumped by this girl that I dated for a super long time.

• 3:48Ryan Holiday?

  And I was, you know, like deciding whether I wanted to do this college thing or not. And it was just this book that was like, was the perfect book at the perfect moment. Um, and it, it's, it's philosophy, yes, but as, as you know, it's, it's philosophy that you can actually read that helps you with actual problems that you're dealing with. And so it was, it was the perfect thing. Um, and I got introduced to it by the guy who does calls about STDs on, on the radio at like from midnight to 2am, um, which is not what I would have expected, but you know, the rest is history.

• 4:19Tim Ferriss?

  Yeah. It's funny. I, I actually had, had no idea, which is hilarious, given how much we've talked about this type of thing before, that that was how you were introduced to all of this. So Dr. Drew also deals with, uh, is very involved with a number of nonprofits that deal with say, uh, heroin addiction and, and, uh, I can imagine why he would pick that book up.

• 4:45Tim Ferriss?

  As a side note, what year of college was this, if you remember? And secondly, not the the year itself, but were you a freshman, sophomore, etcetera? Secondly, how was Marcus when he was penning this notebook, I suppose, that became Meditations? And then lastly, what type of decisions did you make as a result of reading the book?

• 5:06Ryan Holiday?

  Yeah, sure. So I was just starting my sophomore year of college and I ended up dropping out at the end of that year. And I think we met, if I remember correctly, like a few months later. And you you quote Seneca in The Four Hour Work Week, and I think that was one of the things that we connected by.

• 5:23Tim Ferriss?

  Yeah.

• 5:24Ryan Holiday?

  Uh, so it's sort of all was happening at the same time. But Marcus Aurelius, he wrote Meditations, as far as I understand, while he was emperor. Um, so he would have been in his 30s and 40s. He died fairly young. Um, we don't know what, like, we don't know how long he was writing the book. Um, like, there's a few places that allow historians to to to date it somewhat. But we don't know, like, what each specific meditation was referring to or why. We just know that he was writing them usually at night. Um, during during what would only be a very stressful job that you would have to, uh,

• 6:06Ryan Holiday?

  you know, um, decompress about every day. Um, and so so for me, I like, you know, when you go through a breakup, you are usually, you're angry, but then you're also sort of not self-loathing, but you feel crappy and worthless. And you don't know what to do. And so for me, it was this idea of like, like, look, get off your ass. Uh, this is like, you can make the best of this situation. Like, what are you gonna do about it? Um, so I I one of the things that I that I did when I read this book was it. It sort of sent me down this path of other things to read. Like, he says in the book, he says, like, sort of go directly to the seat of knowledge. Um, in in terms of like how to learn.

• 6:50Ryan Holiday?

  And so, uh, he actually says, like, throw away your books, go directly to the seat of knowledge. So I sort of did both. I I I went and I read every book that I could about philosophy, about life, uh, biographies. And and that set me, you know, I've read hundreds and hundreds of books since then. But I also, you know, um, snagged these mentors that showed me.

• 7:12Ryan Holiday?

  Like real life, um, and, and, and they, they taught me things in person. And I think, I think that's when I learned that this idea of philosophy and like a life of doing things and being successful and working were not at all mutually opposed. I think a lot of people find philosophy and it just sends them down this rabbit hole of books and they get further and further removed from reality as a result. And so that this did not have that effect for me.

• 7:42Tim Ferriss?

  And how would you, I feel like philosophy, we talked about this when I originally proofed early, early, I guess drafts of The Obstacle is the Way, your latest book, that you know, philosophy, selling philosophy is problematic, right?

• 8:04Ryan Holiday?

  Sure.

• 8:04Tim Ferriss?

  Because the, I think the term for most people brings, it conjures an image of the schmuck in Good Will Hunting in the bar.

• 8:15Ryan Holiday?

  Sure.

• 8:16Tim Ferriss?

  Who's paraphrasing literature without giving any credit or some like tortured graduate student at NYU who loves to sort of quibble over semantics of

• 8:27Ryan Holiday?

  Right.

• 8:28Tim Ferriss?

  words that, that really, at the end of the day, the, the argumentation is just a lot of fancy tail chasing and that, that's I think a very mainstream interpretation of this word philosophy. How do you view philosophy? How do you, how do you present it to people so that it's palatable or attractive?

• 8:47Ryan Holiday?

  Yeah, so when I sat down to write the book, I, I totally empathize with that. No one wakes up and says like, hey, like I need philosophy. They say, you know, I have this problem and I need a solution to this problem. Well, it turns out that historically that's what philosophy actually was for, specifically Stoicism. Like there, there's a great quote from, from Henry David Thoreau where he says like, you know, to be a philosopher is not about like having subtle thoughts or founding a school. It's, it's about solving the problems of life, not theoretically, but practically. And I think the Stoics understood that much earlier, you know, like 2,000 years ago. Cato, who you've written about. Was considered to be a philosopher, but not because he wrote anything down, but because of how he lived his life.

• 9:32Ryan Holiday?

  You know, Socrates didn't write anything down. Epictetus, we only have his lessons because a student of his wrote them down as notes. And Marcus Aurelius is like, you know, he wanted to be a philosopher, but he was in line for the throne. And so he had to mix his philosophy with being the most powerful man in the world. And so what I think is really interesting about Stoicism, and I talk about this in the book, is when you you look at it and you see that it has this. It tends to have a resurgence when times are really, really bad. So like, Stoicism was very popular during the American Revolution.

• 10:13Ryan Holiday?

  Like, George Washington read the Stoics as a teenager. At Valley Forge, he actually put on a play about Cato, which is one of the most popular plays in the world at that time. Thomas Jefferson died with a copy of Seneca on his nightstand. And then during the Civil War and the Victorian era, you saw another resurgence of Stoicism. Stoicism was big during the industrial, or the, yeah, the American Revolution, the Industrial Revolution, the Enlightenment, the Renaissance. And then, you know, it was also like Marcus Aurelius was living in the decline and the fall of the Roman Empire. Like, it doesn't get much worse than that.

• 10:52Ryan Holiday?

  And so it's basically at its core, it's this philosophy that says like, you don't control the world around you. You only control your response to that world. And so that's a very practical and beneficial philosophy when a lot of things are happening around you that you wish weren't happening.

• 11:13Tim Ferriss?

  No, that makes, that makes perfect sense. I can't recall how I was first introduced.

• 11:19Tim Ferriss?

  To Seneca specifically, I had read at some point or been forced to read, I'm sure, some excerpt of, say, Epictetus or Meditations, probably in college, and as with most things, you're forced to do, most likely did not find a lot of joy in it. But Seneca really grabbed me, and I don't want to go into a long story of why that's the case, but so you have this, let's just call it the trifecta of Stoicism, or the big three, right? You have Epictetus, Marcus really, and Seneca. It seems like Marcus is primarily your guy.

• 11:59Tim Ferriss?

  I don't know, but I've been very curious to see how different people resonate with different Stoic thinkers. And I'm curious, number one, who your primary influence is, and secondly, why you think that is, and why, how you think different people are attracted to different Stoic thinkers?

• 12:21Ryan Holiday?

  Sure. Well, it's interesting, too, about philosophy, like, most people are never forced to read the Stoics, because professors don't like them as much, because there's not as much room for interpretation, like, it's pretty straightforward. And I think that's why you like Seneca, I like him as well. It's like, he's just saying, he says these sort of very timeless, imminently practical truths in a straightforward, clear way, and they talk about, they talk about it in the context of, like, our actual problems. Like, they talk about, hey, like, you know, Seneca will be writing a letter, it's like, hey, like, you know, I heard, like, your wife died, like, here's some advice.

• 13:00Tim Ferriss?

  Yeah. I hear you're getting slandered in the Senate, or there's a lawsuit pending.

• 13:05Ryan Holiday?

  Yeah.

• 13:06Tim Ferriss?

  Here are my thoughts, yeah.

• 13:07Ryan Holiday?

  Totally, totally. So, I, like you, I lean towards Seneca, but also Marcus really, because they were two, like, Seneca was, was one of the most financially successful men in Rome. He was an advisor to Nero, he was a sort of famous tutor and playwright, but he was also skilled at investment, so he was, he was very financially successful. So, when you read his stuff, he's dealing with the sort of the same timeless problems that anyone who has success or works in business deals with, you know, bad, bad markets, you know. Luxury, you know, he's just sort of dealing with all the temptations of business he's talking about. So I like him a lot as well. Personally, I like Marcus Aurelius.

• 13:49Ryan Holiday?

  I like the notion, like, what's so fascinating to me about him is he was literally the most powerful man on on earth, like, he was worshipped as a god in his own lifetime. He could do whatever he wanted. And you read this book that he wrote primarily for himself, and it's just like notes about self-discipline, about being a good person, about like forgiveness, about, you know, honor, about being, treating people well. So that's where I like it. I get the most practical benefit in terms of like leadership and, you know, self-awareness and stuff like that. So that's why I like Marcus Aurelius.

• 14:31Ryan Holiday?

  Although I will say, I think it's funny, like, you read this book, and at the beginning, Marcus Aurelius is like sort of thanking all the people who like gave him lessons. And like, one of the lessons he learned was like not raping his slaves. So it's like, it's sort of, it's very, it's, in the one hand, it's very relatable. Like, he congratulates himself for never having laid a hand on his slaves. So you can sort of take a, you know, it gives you a pretty clear idea of what he's alluding to there. But you realize, like, it's very relatable, but then also very foreign at the same time. Right. But, you know, I mean, how, what other foreign, like, what other person in that position do we have a document about their thoughts?

• 15:16Ryan Holiday?

  Like, when you could, you could literally do anything you wanted without repercussion. Here's a guy, like, writing notes to himself about, you know, being a good person, not taking advantage of everything that he could take advantage of, you know, not, like, forgiving people and all this stuff, which I, which I take a lot of personal value out of. And I think his writing is so clear and straightforward, and it's, it's written in this sort of Uh, it's written in these epigrams that are easy to remember.

• 15:44Tim Ferriss?

  Mm hmm.

• 15:44Ryan Holiday?

  Um, then there Epictetus is great, too. He's a little more lectury.

• 15:49Tim Ferriss?

  Yeah.

• 15:49Ryan Holiday?

  Um, and because he was a teacher, so like you're getting the lectures.

• 15:53Tim Ferriss?

  Gets into the cosmos a bit, too, and in some pretty esoteric ways that aren't immediate. They're they're more abstracted, I think, more.

• 16:02Ryan Holiday?

  Yeah.

• 16:02Tim Ferriss?

  Professor friendly for interpretation.

• 16:04Ryan Holiday?

  He he's the most religious of the philosophers, of the Stoics as well. Um, which personally, not being a religious person, doesn't have the same amount of of relevance for me. Like, when you read Marcus Aurelius, he's not talking about like Zeus and stuff.

• 16:23Tim Ferriss?

  Right.

• 16:23Ryan Holiday?

  Um, which, you know, I think makes it feel a little bit more relatable. And it's definitely the same is true with with Seneca. Like, you if if someone if someone if you'd never heard of Seneca and someone took his works and translated them and took out all the anachronisms, you could very easily fool someone into thinking this was written like in the last decade.

• 16:44Tim Ferriss?

  Oh, for sure. Yeah, no, that's that that for me was critical. And I mean, my the way that I try to define philosophy for people who have never read philosophy or who have been put off by philosophy as they perceive it is, you know, this is an operating system for making better decisions in your life. That's it.

• 17:07Ryan Holiday?

  Mm hmm.

• 17:08Tim Ferriss?

  And I found it so incredibly powerful. You brought you mentioned something just just a moment ago about Seneca being one of the wealthiest people in Rome.

• 17:21Ryan Holiday?

  Right.

• 17:22Tim Ferriss?

  If not the wealthiest at one point. I mean, extremely shrewd investor, investment banker, financier. And let's talk about Stoicism for a second because the word stoic or Stoicism has developed modern connotations that I think perhaps turn people off of the concept of studying something or reading something called Stoicism and.

• 17:49Tim Ferriss?

  I remember a quote, I don't remember the attribution, which was, you know, most people face life with the same stoicism of, as a cow standing in the rain. And I think that people, a very common perception of stoicism, and perhaps this is true for some people, I mean, Cato seems the most kind of Spock-like in a lot of ways, is that you feel neither pain nor joy, you are just basically a cyborg, and the goal is to not experience emotions whatsoever.

• 18:23Ryan Holiday?

  Right.

• 18:24Tim Ferriss?

  And also, I think people perceive it as asceticism, or foregoing all of your worldly possessions, and of course Seneca was very highly criticized and continues to be highly criticized as, you know, the opulent stoic. Like, how can he talk about foregoing riches, or, and I'm kind of laying this one up because I've obviously read a lot about this, but I'd love for you to talk about how you would reconcile some of those things. Like, does stoicism, is it compatible with material or financial success, or being famous, or are they completely at odds with one another?

• 19:05Ryan Holiday?

  Sure. Well, look, I think, weirdly, I think, since both of us are authors, we can very relate, we can very much relate to the problem that's happened with the Stoics over the last 2,000 years, which is, it's a bunch of people psychoanalyzing people they've never met based on their work. And, and over the generations, it builds on itself. And the problem is, they're forgetting is that the Stoics were, it's a philosophy that's designed to solve certain problems, and specifically only those problems. So, you know, Marcus Aurelius isn't writing notes to himself at night that says like, "Hey, like, women are really pretty, don't forget," or like, "Hey, you should laugh and have a good time," or like, you know, "Money is nice."

• 19:50Ryan Holiday?

  Like, he's not, no one needs like a reminder of certain things, right?

• 19:53Tim Ferriss?

  Right.

• 19:54Ryan Holiday?

  And specifically, since he was not writing a book for other people, he was writing A book um for himself, you could, I think you can safely, you can safely assume that he's writing reminders to himself about the things that he's particularly bad at. Right, right. And so it's, it's a selected, deliberately selected view of a person who's struggling with tough things in their life. He's not, again, trying to explain a systemic worldview that you should keep in mind. He's working through problems in his own personal way. And, and maybe if Seneca had had different friends that were really somber and sad all the time, he would have written them different letters.

• 20:39Ryan Holiday?

  Like Cicero was a Stoic or studied Stoicism and there's more joy in his writings. Maybe just because it was a totally different situation. So what I want people to keep in mind is that Stoicism is not about being sad or not having emotions. It's about keeping an even keel and not getting upset or delusionally happy either. And so I, I actually think there's a core tenet of optimism in Stoicism. Like I called the book, The Obstacle is the Way, and it's based on this exercise from Marcus Aurelius where he's saying like, look, um, it doesn't matter if you're trying to do something and you get blocked. This is actually an opportunity to practice virtue.

• 21:20Ryan Holiday?

  So that like, basically what he's saying is like, hey, I know this thing that you, that happened that you think is bad. It's actually good and it's actually a chance for you to do good things. To me, that's like, that's cheerful and that's happy. And that's, that's the kind of attitude of someone who never gets depressed. Because they always feel like they have a way out. And I think what the Stoics were saying is like, if you go around thinking that the world is great and that it's always going to work out exactly how you plan and that people are always going to treat you well. Like in, in one of the things Marcus reminds himself that tomorrow, when he wakes up, people are going to be rude, they're going to cheat, they're going to steal, they're going to argue with you, they're going to do all these things.

• 22:05Ryan Holiday?

  He's doing that so he can go out and interact.

• 22:08Ryan Holiday?

  Act with them in a positive way rather than feeling let down and pissed off all the time.

• 22:14Tim Ferriss?

  Right, right.

• 22:15Ryan Holiday?

  So yeah, so I think that's super important and I think that's something that's totally been missed from Stoicism and I think that's why you and I are attracted to it. And find value from it in our lives. It's not like confirmation of our pessimism or cynicism and on the contrary, I actually. Feel like it's intimately connected with being happy and fulfilled as a person.

• 22:35Tim Ferriss?

  Yeah.

• 22:35Ryan Holiday?

  Um, and that's why I don't think it was a contradiction at all that that Seneca was successful and. Seem to genuinely enjoy his life and and was, you know, had had financial riches. I think. Um, Nassim Nicholas Taleb is another person. It it's the point is making money is usually a result of. Being successful or good at something. It's can also be a result of luck or fortune. Um. And having it doesn't say anything good about you and it doesn't say anything bad about you either. And the only problem that really comes from wealth. Well, there's a couple of problems, but being financially successful and. And I, you know, I I'm I'm not a millionaire, but I'm I'm doing well. There there's temptation.

• 23:20Ryan Holiday?

  Uh, to, you know, spend money on, you know, negative things, let's say. But the real problem is thinking that you need this money to survive. And so it's funny like. Seneca has this reputation for being opulent, but in Letters to a Stoic, he talks about actually practicing poverty like one day a month. Pretending that all his money was stolen or lost and that he's walking the streets as a homeless person. Um, he's doing that so he can enjoy his wealth while he has it. But never feel like it's integral to his survival or, you know, existence as a person either.

• 23:58Tim Ferriss?

  Right, right. No, it's it's been, uh. I I think, you know, to not to bring Fight Club into this, but you know, the things we own end up. Owning us and I think there's a big difference and this might actually be a thorough quote, uh. Who had his own contradictions like we all do.

• 24:16Ryan Holiday?

  Yeah.

• 24:17Tim Ferriss?

  Uh, I heard he used to sneak off and have big meals at Emerson's house while he was at the, uh, at Walden, but. And that is that, you know, the problem is not having riches. It's when riches have you.

• 24:29Ryan Holiday?

  Totally.

• 24:29Tim Ferriss?

  And I think Seneca comments on that quite extensively. And, you know, the problem is not having wealth. It's when it it becomes a source of sort of fear and greed, and it dictates how you behave as opposed to being a tool. Therein lies the problem. So besides, besides, obviously, these these fantastic works of literature, or I suppose that might not even be a fantastic label. I mean, in some cases, they're war journals of sorts.

• 25:03Ryan Holiday?

  Right.

• 25:04Tim Ferriss?

  Coming back to seeking out mentorship in real life, teachers in real life. Was Robert Greene really the first person to take you under his wing in that in that way? Or are there, was there someone else who was a pivotal teacher to you?

• 25:24Ryan Holiday?

  Sure.

• 25:25Tim Ferriss?

  And how did that come to be?

• 25:28Ryan Holiday?

  Yeah, so, um, so actually, before I met Robert, I was working with with Tucker Max, who we both know.

• 25:34Tim Ferriss?

  Right. And Robert, of course, just to give some context, maybe you could explain, give some context on both of them.

• 25:39Ryan Holiday?

  Yeah, so Robert Greene wrote The Forty Eight Laws of Power, The Art of Seduction, and The Thirty Three Strategies of War. And then I I met him in, you know, two thousand six, two thousand seven. I was in college. I met him through Tucker Max, who's another number one New York Times bestselling author, sort of known as a as a really good sort of internet marketer and and thinker, and then also, you know, does crazy things. But I I met, Tucker showed me about marketing. He introduced me to Robert. Robert really showed me about writing and researching and learning. And I worked with Robert on his his last two books. He wrote one called The Fiftieth Law, which is about fearlessness with with the rapper Fifty Cent. And then he wrote one called Mastery, which is about, you know, becoming a master at whatever it is that you do.

• 26:24Tim Ferriss?

  Yeah, great work.

• 26:26Ryan Holiday?

  Yeah, I I love it. It was like an honor to be a part of it. Um, so those were my my two my my two mentors in in like sort of direct mentorships. But I also think like, you know.

• 26:37Tim Ferriss?

  How did you, just to not to interject, but how did you, just in the sort of the details, the nuts and bolts, how did you initially connect with Tucker Max? How did you initially?

• 26:48Ryan Holiday?

  It it all goes back to this college newspaper. I was writing, I had a column there and I decided I would use it to as an excuse to write articles about people I wanted to meet. Um, and so I I wrote a review about Tucker's website and I emailed it to him. And we just started this relationship and then I would just email him and ask questions. Um. So it's funny, I think you probably see this, like, people think mentorships are these like very official relationships, like the way that an apprenticeship was like your parents basically sold you to someone in exchange for like room and board for a certain number of years, then you officially learn a trade. Like, a mentor is anyone who um you learn from, who gives you advice and and teaches you things.

• 27:33Ryan Holiday?

  And you don't actually have to meet them for them to be your mentor. Seneca talks about this. I forget who he's talking about, but he says like, you know, find yourself someone that you can use as like a benchmark or a a ruler to compare yourself to, so you can decide when you have, you know, difficult choices, like what would this person do in this situation? How would they act? What should I do here? Um, and so like, I I would even say you were you were definitely one of those people, like I would. We don't have some official mentor mentee relationship, but like you've taught me so much and I've I've I've asked you questions and and hopefully like, you know, it's it's gone both ways, but like you're older than me, you're more successful than me, you've taught me things, and that's what I think a mentorship is.

• 28:16Ryan Holiday?

  And you can have that with basically anyone. I think a lot of people, they hold out for this like sanctioned official relationship rather than just like learning from anyone who has wisdom or advice or value that they could pass your way. Um, and that you and if you put it into practice and you do something with it. They see value in that as well.

• 28:38Tim Ferriss?

  Yeah, no, I I agree and I appreciate the kind words, obviously.

• 28:44Ryan Holiday?

  Like you were the one, you were the one who, like, I I was studying Stoicism was interesting to me and I think I mentioned it to you. And then you encouraged me to write an article about it for your site, which sort of set me down this whole path to begin with. Um, and so I I think, you know, it's it's weird how these little conversations can have such a big impact on your life. Um, but it it just depends on, I think, you know, how people respond to and treat the opportunities that they get. That often don't look like opportunities when they, you know, sort of first make their appearance.

• 29:17Tim Ferriss?

  Oh, definitely. I mean, Jack Canfield, who co-created Chicken Soup for the Soul, was uh, is largely responsible for the Four Hour Work Week becoming a book. And it was just one or two offhand comments that he made to me that were encouraging in the early days that that produced the proposal because it coincided with a bit of downtime. And he effectively helped force my hand by making introductions that led to conversations with agents and uh, it's it's it's incredible how in the case of uh, of Jack, you know, he became a mentor to me. Uh, because very similar to the newspaper, I used volunteering for

• 30:03Tim Ferriss?

  tech nonprofits as a way to meet the people I wanted to meet. Uh, because these events would put on, these organizations, like the Silicon Valley Association of Startup Entrepreneurs, it's a mouthful, but Sbase uh, or TIE, the Indus Entrepreneur, put on large events. Uh, every few weeks or every quarter, they'll have an event where they bring in thought leaders and their panels and so on. And so I I volunteered for the, for Sbase when I first moved to Silicon Valley in two thousand and uh, really just kicked ass as a volunteer for a few months and continually took on more and more and more responsibility until I was invited to sit in on the Board meetings, just as an observer, basically.

• 30:48Tim Ferriss?

  And they were talking about their next main event, I think is what they called it. And I just kind of raised my, they're like, well, who are we going to get to do this and manage the event? And wrangled the speakers and I just kind of shyly put up my hand and I was like, I'll do it. I'll take care of it. And so they handed it over and I put together a panel. God, what was it called? It was called something like, you know, Titans of Consumer Products or something. And I invited, you know, the creator of the, the clapper and the pet rock. I invited the guy, Ed Bird, who was sort of the jointly responsible for popularizing creatine in the United States as an athletic supplement, which was a huge, huge deal.

• 31:29Tim Ferriss?

  The founder of Cliff Bar, Jack Canfield, and so on and so forth. And got to know Jack by inviting him to this event and having a bunch of emails back and forth. And then over the years, you know, asked him every once in a while, pretty, pretty rarely, would ask him very specific, short kind of life questions. And that's how the whole thing came to be. In the case of Tucker, for instance, how, how long after you initially introduced him to the article you wrote, did you start asking questions? Over what period of time? You know, how frequently did you email him? I think this is something people need to understand because asking someone to be a formal mentor

• 32:13Tim Ferriss?

  is like the absolute best way to never have a good mentor. Totally. Because it's like, hey, you want to sign up for like a unpaid, part-time job? Because you're so, you have so much free time. It doesn't work. So I'd just be curious to hear sort of what you did and what you would recommend people do if they're trying to find or looking for that type of, of teacher. I think mentor is problematic because they think of it in such formal terms, but. Well, maybe you could talk on that point.

• 32:40Ryan Holiday?

  Yeah, totally. Um, I think it was like, it was once, it was once every couple of weeks, uh, or now a couple of months, probably. Um, and I would just ask like questions that I thought, um, would be easy, would be helpful to me, but very easy for him to answer.

• 32:58Tim Ferriss?

  Right.

• 32:59Ryan Holiday?

  Um, and that's what, you know, it's like, hey, if you want me to read your manuscript, that's like a lot of work for me to do.

• 33:05Tim Ferriss?

  Yeah.

• 33:05Ryan Holiday?

  Or this, this would be more for you. If someone, if someone wants you to read their manuscript, you're like, okay, that's like a week of my time. If someone wants you to, to give a five second instant opinion on a title, you're like, sure, that's, that's one email.

• 33:17Tim Ferriss?

  Right.

• 33:17Ryan Holiday?

  Um, and so I think people don't think, one, they don't think about, you know, what they're actually asking. And then two, um, they, they ask a lot over and over again, when, when really, it, it's actually interesting. There's this thing called the Ben Franklin effect. I don't know if you know this story, but.

• 33:33Tim Ferriss?

  About the lending library or the, uh?

• 33:35Ryan Holiday?

  Yeah.

• 33:36Tim Ferriss?

  Yeah. Why don't you tell the story? This is such a great story.

• 33:38Ryan Holiday?

  So, so Benjamin Franklin, there was this, this member in, in Congress or one of the things about the American Revolution or, I, I don't really remember where it is actually, but Benjamin Franklin faced this sort of enemy in a legislative body, who he desperately needed his support and they seemed to be intracta- in-intractably opposed to each other. And what Benjamin Franklin did was he heard that this guy loved rare books and had a prized library of rare books. One book that he valued above all the others. So Ben Franklin, being a somewhat bold man, walks right up to this guy and just asks him if he can borrow his most prized possession. And the guy sort of like stunned is like, um, I, I guess Benjamin Franklin borrows it,

• 34:22Ryan Holiday?

  just puts it on his shelf for like two weeks, doesn't touch it, doesn't use it, and then returns the book to the guy. Um, and what he finds is that having borrowed this guy's most prized possession, they now have not only the shared connection, but the guy has to justify in his head, why he would loan this thing that's so valuable to someone else. And so, he starts to tell himself this story that Benjamin Franklin must be good. He must be someone worth loaning this thing to. Sort of using cognitive dissonance to your advantage. Um. And basically, it's been it's been verified, um, you know, by psychological studies since then.

• 35:01Ryan Holiday?

  It turns out that when you do someone a favor, you actually feel indebted to them. And so like, and you you would think that doing someone else a favor would make them indebted to you. In fact, asking something small of them in some ways can build a better connection. Because now they're like invested in you. And um, I would try to ask questions or think about things that they would they would like. And that they would, you know, feel like they got value out of too. Um, and and that's something that, you know, I I it's like a subtle psychological shift. The people miss for some reason.

• 35:41Tim Ferriss?

  Yeah, it's Ben Franklin, such a fascinating character. I really enjoyed reading Walter Isaacson's biography of Ben Franklin. Uh, which leads me to ask you, I mean, uh, which which historical figures do you find most instructional, helpful? I mean, who are the who are the figures outside of the big three Stoics that you sort of repeatedly look to as your own benchmarks or to learn from?

• 36:10Ryan Holiday?

  Um, yeah, there's there's obviously a bunch. Um, you know, in the book, I really like I I talked a lot about Ulysses S. Grant, who I thought was really interesting and a sort of a totally underrated, underappreciated historical figure. Um, I talk about John D Rockefeller, who I thought, you know, and and again, all these people have problems. And so I don't want it to to send into like hero worship of any kind. It's you you look at the people and you look at the good that they bring to the table. And you focus on that, not on, you know, the negative stuff. Um, but I talk about Ulysses S. Grant, William Tecumseh Sherman, who is another Civil War general I'm really interested in. I think Richard Feynman is a fascinating character.

• 36:52Tim Ferriss?

  Definitely.

• 36:53Ryan Holiday?

  Who asked all sorts of interesting questions and he he had this what seemed to be the sort of joy and curiosity to him that I that I appreciate a lot. Um, Cyrus the Great is another really fascinating character who was

• 37:07Tim Ferriss?

  Definitely.

• 37:07Ryan Holiday?

  Who was, again, one of the most powerful people in the world, but seemed to be universally regarded as a good person and not in like a propagandist way. Um. So those are, you know, those are some of my favorites. I don't, I don't think it's a stretch to use fiction either. Like I, I find it weird that people don't look at fictional characters as either good examples or bad examples.

• 37:29Tim Ferriss?

  So who are, who are some of your fictional favorites?

• 37:32Ryan Holiday?

  Um, well, that, one of my favorite books is this book, uh, What Makes Sammy Run by Bud, by Bud Schulberg. It's about this Hollywood, uh, screenwriter. It's like a young Jewish kid, um, who's like a total hustler who's like endlessly ambitious. And it's sort of, um, it's, it's very Gatsby-esque, um, the, the book, but the, the point is this guy's like hustling and running all the time. But he never stops to question why. And it actually, he read, like the, you know, the, the moral conclusion of the book is that he gets everything he wanted and it's like the worst thing that you could ever wish on someone.

• 38:06Tim Ferriss?

  Right.

• 38:07Ryan Holiday?

  And so that's something like I try to think about a lot too. It, it's really, I think it, it's, it's about finding the people that you relate to in fiction or nonfiction and then seeing what you like about them, like you like about yourself in them and using that to bring out more of it. And also seeing what you don't like about yourself in them and using it as a cautionary detail.

• 38:30Tim Ferriss?

  Right. Uh, that's a, that's a really good point. Yeah. I, I have a few books on my bookshelf facing out. Uh, and I just moved into a new place. I had the chance to organize my books however I wanted, which was a, a delightful and extremely time-consuming monkish process for me being as OCD as I am, but the, the, uh, one of them is Zorba the Greek. So

• 38:53Ryan Holiday?

  Right.

• 38:53Tim Ferriss?

  Zorba is just such a great cautionary tale for me. Cause you have like the, the, the uh, intellectual slash want to be intellectual who's very introverted and spends too much time tail chasing in his own head versus Zorba who's so engaged in the moment, et cetera. Uh, you know, very maybe epicurean in some ways. And, uh, yeah, that's really interesting. Also Dune. I thought, uh, you know, a number of the characters in Dune were very, very interesting. Uh, stranger in a strange land as well. Um. So let's, let's look at where you are now because I, I'm, I've been continually impressed

• 39:35Tim Ferriss?

  by how, at, at what a young age you have accomplished certain things, whether that's responding to huge responsibilities at American Apparel with marketing, responding to those criticisms, publicly dealing with all, all sorts of difficulties, not difficulties, challenges that we all have, but professionally on a, on a pretty public scale. You're 26 now, is that right?

• 40:04Ryan Holiday?

  Yep.

• 40:05Tim Ferriss?

  Yeah. All right. So this is your third book, which, just to put it in a chronology, I mean, The Four Hour Work Week, I guess it was published or written when I was 29. So you're, you're still three years ahead of me with three books. What, to what do you attribute the, your ability to get shit done? I'm just very curious as to if it's like, well, you blend my two parents and here you are. Like that's how my parents are. This is how I am. How much is nature versus nurture? I mean, what has contributed to your ability to, to multitask and also to get this, this much stuff done at this age? I'm curious to hear your, your opinion.

• 40:49Ryan Holiday?

  Sure. Well, I mean, look, so obviously I had two smart parents. They inculcated in me, you know, a love of reading and questions and sort of told me I could, you know, do whatever I wanted with my life, like, which was, which was all very helpful. And I wasn't like someone who came from, you know, and I talk about those type of people in the book, the people who came from sort of nothing or worse than nothing. And that's why they were successful. That's not me. And then I, I had these amazing mentors, which were very helpful. And I, I also have a big head start on people. I mean, I dropped out of college when I was 19 years old. So I've been doing this for a long, like, most people my age started at 21 or 22.

• 41:26Tim Ferriss?

  Right.

• 41:26Ryan Holiday?

  So they're sort of just getting started. But, you know, that being said, I think, I actually, and the reason I wrote this book is because Stoicism was Like I can trace all so much of the good stuff in my life to specific passages in Stoicism. That helped me or made me think about, you know, certain things like this idea of the obstacle being the way that there's no such thing as bad things happening to you. That everything is an opportunity to like prove yourself or to do something good is is something that's been, you know, enormously beneficial to me. There's also, there's a quote in book five of meditations that I used to have printed up on my wall. Um, and it's this conversation where um, Marcus is sort of actually having it with himself like it's dialogue, but he's like.

• 42:09Ryan Holiday?

  Um, so you're waking up in the morning and you're, you know, you're covered in the blankets and you know, you should get up. But you say to yourself like, but it's so warm here. Like I want to stay here and and he's, he says like, but look, you're a human being. Your job is to get up and work and it's like, what do you mean? You've, you've worked enough like would, would an animal say that? Like, would an animal ever say that they were, they'd done enough work? Um, and then he says like. You know, people who love what they do, wear themselves down doing it. They forget to eat and sleep. They just work because it's not work. It's, it's who they are. And I think.

• 42:46Ryan Holiday?

  For me, getting stuff done has been a function of, of being able to start having that conversation with myself when I was, you know, nineteen years old rather than like. You know, partying late at night and then waking up hungover every day. Like I didn't do that and but i- it's. I, I really think it's the cumulative process of waking up every day. And going to work and like really working and not caring about the rewards or. The success, but working because I love what I'm working on that, you know. Compounded interest is one of the most powerful forces on earth, right? And you can apply that to your own work and every day if you wake up and you work on something, you get a little bit closer. And it, it, it grows. And I think that's.

• 43:30Ryan Holiday?

  You know, that's, that's been, you write one book, it's easier to write another book, you know? Um, and then you write two books, it makes it easier to write a third book and um. I've, I've never been a fan of doing just, I think you're like this too. I don't get how people do just one thing like I, you're really good at investing, but could you just do that? I don't think that would fulfill you as a person.

• 43:52Tim Ferriss?

  Yeah, I couldn't do that alone.

• 43:54Ryan Holiday?

  And I I think it's weird, but I found that the more things that you're doing, the better. It's like, okay, if you do one thing, you can be really good at it. If you do two things, you feel really busy. But if you do like three to five things, you're not that busy and they all help each other and make you better at them. So for me, like writing and marketing and like, you know, research and all the things that I would doing at the same time made me better at all of them. And it sped the whole process of learning up really fast.

• 44:26Tim Ferriss?

  When you are most productive, how often are you running? Because I know that that is another part of your life, or at least historically has been.

• 44:35Ryan Holiday?

  Yeah, so um, I run almost every day. I started, um, I I run every day, but then I I also, you know, from some of your stuff and other people, I I know is not the best thing physically for you. So I usually do CrossFit like two days a week. Um, and then I try to swim one day a week, and so I run the other, the other days.

• 44:56Tim Ferriss?

  Right, yeah, I found, uh, I think long walks are also very underrated.

• 45:02Ryan Holiday?

  Totally.

• 45:04Tim Ferriss?

  Which, uh, yeah, I mean, we could, we could go through the long list of people who have said that historically.

• 45:09Ryan Holiday?

  Yeah, well, I actually, I try not to think about, I I definitely don't think of walking that way. And I actually try to not think of running that way, almost not as exercise. Like, I think it's better for your, it's has a better impact on your brain than it does on your body.

• 45:24Tim Ferriss?

  I agree.

• 45:25Ryan Holiday?

  Definitely walking, it's like, I I've written huge chunks of my books because I went for a walk and then I had a breakthrough that I wasn't expecting.

• 45:32Tim Ferriss?

  Yeah, I think, I think it all, it might be, uh, Enen Taleb who also doesn't, doesn't trust people who won't go for a walk when they speak with him. Uh, I could be, I could be just making that up, but I'm, I'm pretty sure I'm not.

• 45:47Ryan Holiday?

  That's about right.

• 45:48Tim Ferriss?

  Yeah, it sounds about right. Or, and then he'll sprint to imagine, what did he say? When he, when he has to, uh, motivate himself to sprint, he will think of like running after the head of the Federal Reserve and smashing them with a baton on the back of their head or something. He's a hilarious guy. Who do you turn to? Actually, let me, let me back up to, to a separate question. You're a prolific reader. You have a sort of recommended reading list that's quite popular, an email list that people subscribe to.

• 46:20Ryan Holiday?

  Yeah.

• 46:21Tim Ferriss?

  And I've really been impressed by your synopses of the books that you read. But for someone who is not an avid semi-full-time researcher like yourself.

• 46:32Ryan Holiday?

  Right.

• 46:34Tim Ferriss?

  What are the top, say, you know, two or three books that you either discovered or delved into while researching the obstacles away? I mean, if you had to pick your top two to three, you're like, all right, if you want to maximally gain in whatever way, I'll leave it open to you.

• 46:51Ryan Holiday?

  Sure.

• 46:52Tim Ferriss?

  Read these two or three books. Like, if these are the only two or three books you read this year, you'll be better off for having that.

• 46:59Ryan Holiday?

  Okay, well, I'm looking at the bibliography right now. And some that jumped out at me that were total favorites. Ron Chirrow's biography of John D. Rockefeller, which is Titan, The Life of John D. Rockefeller, was like a total game changer to me. It was an amazing biography. I like Sarah Bakewell's book, How to Live. It's like a series of essays about Montaigne, who invented the essay.

• 47:25Tim Ferriss?

  Yeah.

• 47:25Ryan Holiday?

  He's really fascinating. Sarah Bakewell.

• 47:30Tim Ferriss?

  Cool.

• 47:30Ryan Holiday?

  Um, I like, uh, let's see, oh, I read this book, um, The Fish That Ate the Whale, The Life and Times of America's Banana King. Um, he was this, uh, a totally fascinating but relatively unknown historical figure who started, he started a fruit company buying spoilt, like, the day-old, not day-old, but the about-to-expire bananas that would be imported in, like, late 1800s America. And he would sell them, um, like, he would sell them by train car. He ends up, he ends up buying United Fruit. He starts a small fruit company that it grows to be so big that it buys United Fruit Company,

• 48:14Ryan Holiday?

  which is the biggest fruit company in the world. Um, so that's why he's known as the fish that ate the whale. He's this sort of fascinating Jewish businessman. Um, I read a really good biography of Edison by Matthew Josephson called Edison, A Biography.

• 48:32Tim Ferriss?

  Got it.

• 48:33Ryan Holiday?

  And if there was any others, I'm trying to think. Yeah, those were so, oh, and I read a really good biography of Ulysses S. Grant called Ulysses S. Grant Triumph Over Adversity.

• 48:44Tim Ferriss?

  Got it.

• 48:44Ryan Holiday?

  That I loved a lot.

• 48:46Tim Ferriss?

  Cool. Just writing these down myself. Because, uh, because I need another 20 extra books on my Kindle that I haven't read. I'm just kidding.

• 48:56Ryan Holiday?

  Right. I want to give you some more 700-page biographies because I know you need more of those.

• 49:03Tim Ferriss?

  Uh, very cool. The Fish That Ate The Whale. That is a fantastic moniker.

• 49:07Ryan Holiday?

  Yeah, that one's really short and you'll really like that guy. He was crazy. Um, and he, he was like the, I don't, I can't even describe. You should just read the book. It's amazing. The writer that wrote it, um, uh, Rich Cohen wrote another, uh, amazing book called Tough Jews, which was about like J E W S.

• 49:28Tim Ferriss?

  Right.

• 49:28Ryan Holiday?

  Um, about Jewish gangsters, like basically like the people that you see on, um, on Boardwalk Empire.

• 49:34Tim Ferriss?

  Yep.

• 49:34Ryan Holiday?

  Um, he's an amazing writer who you'd really like.

• 49:37Tim Ferriss?

  Cool. Uh, so I view books oftentimes as, as tools, right?

• 49:43Ryan Holiday?

  Yep.

• 49:43Tim Ferriss?

  Uh, uh, part of the toolkit for making these better decisions, uh, obviously, and enjoying life at the same time. I do love reading.

• 49:53Tim Ferriss?

  What other, are there any other tools that you use or rituals that you have had consistently and found useful? Uh, so I'm curious, maybe we can start with the, the second part of that. What is your, what is the first six, like 60 to 120 minutes of your day look like? When do you wake up? What is, what is your morning routine look like? And then maybe we can talk about your, your daily routine.

• 50:16Ryan Holiday?

  Yeah.

• 50:16Tim Ferriss?

  If there is one.

• 50:17Ryan Holiday?

  So I try to wake up somewhat early, like 7:30 to 8. I'm not always successful at it. Um, so I try to wake up early and I try not to check my email in the morning if I can, but I'm not usually successful at that either. But, um, I try to sit down and I write for like the first hour to two hours in the morning. I find that there's less going on, there's less people bothering you. Um, there's a great writer, uh, he has a site called Farnham Street. His name's Shane Parrish.

• 50:45Tim Ferriss?

  What is the name of the site?

• 50:47Ryan Holiday?

  Farnham Street, F A R N A M.

• 50:50Tim Ferriss?

  Okay.

• 50:51Ryan Holiday?

  Um, and he wrote an article recently where he's like, well, the number one productivity secret is just wake up early. Um, because there's less going on, you're more productive at the beginning of the day. So I try to get my writing done in the morning, like whatever I'm working on. I try to like bust out an article from working on a book. I try to tackle a chapter. Um, I just try to, I try to write in the morning, um, for an hour or two. And then I sort of get to work from then when everyone else is kind of waking up and getting going.

• 51:20Tim Ferriss?

  Right. Okay. And then, uh, what is, what does your day look like from that point forward?

• 51:25Ryan Holiday?

  Yeah, I usually go out to breakfast. Uh, I try to eat at the same, same restaurant every day. Rather than like, you know, deciding what I want to have for breakfast.

• 51:33Tim Ferriss?

  What do you eat?

• 51:35Ryan Holiday?

  Uh, usually three eggs and two sides of bacon. So I get a ton of protein. Uh, and then I'll have like guacamole or something with it, uh, if I wanna.

• 51:46Ryan Holiday?

  Um, liven it up a little.

• 51:49Tim Ferriss?

  And get some non-animal matter.

• 51:51Ryan Holiday?

  Yeah, exactly. Um, uh, although I got chickens at my house, I don't always go out anymore. I sometimes I have fresh eggs at the house.

• 51:58Tim Ferriss?

  And you're in, you're in Austin.

• 52:00Ryan Holiday?

  Yeah, I live in Austin. Um, and then I, then I go to work like I, I have a, a one index card that I write. Usually the night before my list of things to do that day. And I try to keep that list like pretty small, like five to seven things usually. Um, and I, I cross all those things off. They could be small things like email so and so. Or it could be like, you know, write chapter three, you know, it could be big thing or a little thing. I cross those lists off, those things off. And then the rest of the day is like just responding to stuff that's happening, whether that's emails or phone calls that I've scheduled. There are meetings that I have to do. I try to avoid as many meetings or phone calls as humanly possible. Um.

• 52:41Tim Ferriss?

  How do you, how do you go about doing that? Are you diplomatic or what's your approach to deflecting meeting requests or coffee dates and so on and so forth?

• 52:49Ryan Holiday?

  Yeah. Paul Graham actually has a great essay about this called maker versus manager.

• 52:53Tim Ferriss?

  Oh, it's such a good essay. Yeah, that's a, that's a great piece.

• 52:56Ryan Holiday?

  But it's really hard, like, uh, you're someone who fits in this category when you're both a maker and a manager. Um, like most, most makers are deliver, are just not good at doing the other thing, so they don't do it. It's hard when you actually have stuff you have to manage. Um, but I try to. I just, I just say like, hey, like, sometimes I'll just lie. I'll say like, hey, I'm traveling. I can't do the phone. Or um, like, hey, I really prefer email. Like, if we can hammer this out over email, it'd be much better. And I know that sometimes email takes longer than doing a phone call because you have to go back and forth. But the point is, it doesn't interrupt what you're doing and it does it like on my schedule.

• 53:37Ryan Holiday?

  Um, so that's, I, I, I just try to be upfront about it. I just say like, hey, like, look, I really hate email. Um, or I really hate, you know, jumping on the phone. Can we just do this over email? And most people are understanding and the people that aren't, I either don't care. Or I understand that they're more important than me and they get to pick, they get to dictate the terms, you know?

• 53:58Tim Ferriss?

  Yeah, it's, yeah, I'm glad you brought up the point about, number one, uh, I have the exact same habit with index card. That, that is, uh, the finite surface area, I find. Much like Parkinson's law helps to refine how you prioritize. But the, the, the point you made that I think is really important to underscore among others is that just because email might take slightly longer does not mean phone is better. Uh, and similarly, you might choose a slightly longer driving route because it's easier to remember and it's more scenic.

• 54:36Ryan Holiday?

  Oh, that's a great analogy.

• 54:37Tim Ferriss?

  As opposed to being like, yeah, I'm gonna sit through like horrible traffic with people honking where I have to really pay attention the whole time and can't daydream. Uh, but it's 15 minutes, uh, shorter route. And there's, you know, a, a really important quest, or an important question that I've learned to ask myself. And I don't, I'm sure I didn't create this, but I don't remember the attribution if I didn't. And that is, um, it's not whether you can afford the time or not, it's whether you can afford the distraction. And you know, that's why it's like, yeah, it might only take you five minutes to call someone. But you and I both know if you're writing something or if you're a coder,

• 55:20Tim Ferriss?

  that could mean you start over, you start the clock from zero and it's going to take you 45 minutes to get back into the flow of what you were doing.

• 55:28Ryan Holiday?

  Yeah.

• 55:29Tim Ferriss?

  What, what, speaking of flow and writing, I mean, what, what do you, I think that, you know, I admire your writing because it's a reflection of clear thinking and I'm wondering what you see as the most common mistakes that writers make? What are some of the most common mistakes where you, you, you write for quite a few outlets online? And you're really prolific, you, you write a lot more than I do. And you know, I'm envious in a way of your, of your output. What, what are the, what are the biggest mistakes that you see writers making? Not professionally necessarily, but just like stylistically,

• 56:10Tim Ferriss?

  editorially, what are, what are some of the bigger mistakes, do you think?

• 56:13Ryan Holiday?

  Yeah, well, I think it's weird. I write a lot, but I think I write a lot out of humility. Like I'm trying to get better and I think that the only way you do it is by making commitments to write a lot, publishing and sort of getting feedback. And like, so I, I, you know, three books in, in three or four years is, is a lot, but plenty of people do more. The articles are designed to make the books better. That's the way that I think about it.

• 56:36Tim Ferriss?

  Right.

• 56:37Ryan Holiday?

  But I think a couple of mistakes that writers make. One, they don't have anything to say. They, they think that writing is good, like they're, they think that writing is the skill that is scarce and good. Like putting sentences and words together is, is good. It's like, look, I would read a biography written by someone with like a seventh grade education. If what they were talking about was fascinating, you know, like I'm, I'm like, have you ever seen that thing where it's like, they, they take a bunch of sentences and they take all the vowels out or they move the words around?

• 57:12Tim Ferriss?

  Right, and you can still read it.

• 57:13Ryan Holiday?

  And you can still read it?

• 57:13Tim Ferriss?

  Yep.

• 57:14Ryan Holiday?

  Yeah, it's not the technical skill that's rare, it's having something interesting and compelling to say. So I think that's the big thing is people don't have that much to say. And they focus all their time on technical writing rather than like saying something that's never been said before. Um, but at the, this maybe ties into that, but I see a lot of writers who, who start writing before they've figured out exactly what they plan to say and who they're saying it for. Like they're trying to find the point while they're going. Um, and so I like, I use note cards to organize my research and like, I very rarely write anything that isn't fully outlined and sketched out, especially books.

• 57:57Ryan Holiday?

  So I like, the writing is the easy part, figuring out what you have to say and doing the research and bringing something new to the table. That's what's special and rare. Um, so I try to, that's, I, I focus my energy on the finding the stories or the thing that I'm bringing to the table that no one else but me could bring. And I think far too many writers, um, skip that. And that's why we get these crappy bulleted lists or, you know, on the other hand, like an eight thousand word article that like could have been 20% of the length. Um, and, and so I think those are, those are mistakes that writers make a lot. Um,

• 58:37Ryan Holiday?

  I think also just not being honest. I think a lot of people are either pretending and like puffing themselves up with their writing. Or they're hiding something like James Altucher.

• 58:47Tim Ferriss?

  I was just, I was just gonna mention James. He's so good at doing the opposite.

• 58:51Ryan Holiday?

  Yeah, he has this rule where he like, he writes the thing that he doesn't want anyone to know about himself. Um, like he, like whatever he's afraid to say, that's what he wants to write an article about. And look, sometimes that ends disastrously and he gets in trouble. But most of the time it creates this vulnerable, authentic voice that people who, people relate to because no one else is saying these things. And, and that's what your jo- your job as a writer is to touch something inside of the audience. And you can't do that if you're, if you're lying to yourself.

• 59:27Tim Ferriss?

  Yeah, no, definitely.

• 59:30Tim Ferriss?

  Huh, I I find I find writing process just endlessly fascinating.

• 59:36Ryan Holiday?

  Totally, because no one does it the same way.

• 59:39Tim Ferriss?

  Yeah, everyone's different. That's that's one thing I realized really early on. Like, there are there are best practices for marketing bestselling books. There are

• 59:52Tim Ferriss?

  very, very few consensies about the best way to write a best reading book, if that makes sense. And that's part of the reason why I fell in love with daily rituals, which profiles, you know, one hundred and seventy or so world famous creatives, whether it's writers, composers, scientists, etc., and how their daily schedules are laid out because they're so different. It's it's really fascinating to me.

• 1:00:18Tim Ferriss?

  Do you watch documentaries? If so, what what are what are your favorite documentaries that come to mind?

• 1:00:25Ryan Holiday?

  I love documentaries, but I don't watch that much like TV, so I don't get to watch as many as I like because, um, yeah, but some favorites. I like Fog of War, I think is amazing. That Phil Spector documentary from a couple of years ago is pretty crazy. I think it's called The Wall of Sound, but I forget what it's called exactly. There's the guy who did Fog of War has a new one out about Donald Rumsfeld that I want to see called The Unknown Known.

• 1:00:58Ryan Holiday?

  But my I love Ken Burns. I've watched like pretty much every Ken Burns documentary you could ever see, including all ten hours about the Civil War and all ten hours about the National Park system. So I think like what I love, I love when you like all I love any art where the person doing it is clearly like the master of their craft. And to me, Ken Burns is like the best person who ever lived at documentaries, and I don't know how anyone could beat him. And so it's like, I'll watch, you know, and ten hours about national parks, like because it's that good, even if you don't care. So I think I I love his stuff.

• 1:01:38Tim Ferriss?

  Yeah, that's a hat. It's funny you mention that. That's how I feel about John McPhee as a nonfiction writer.

• 1:01:43Ryan Holiday?

  Totally.

• 1:01:43Tim Ferriss?

  I mean, he's he's, for those people who don't know who he is, he's at least a one time, maybe a two time Pulitzer Prize winner. And I was fortunate enough to have him in seminar for nonfiction writing called the class was called the Literature of Fact when I was an undergrad for one year, which was amazing. It was really hilarious, too, to get back a three-page writing assignment and to have more red ink from him on the page than black ink. You really feel like a dumbass when you realize how sloppy your thinking is when you get something like that back. But, you know, he's written books on everything for an entire book on oranges, an entire book on one tennis match, an entire book on hand-carved wooden canoes,

• 1:02:26Tim Ferriss?

  a book on Plymouth Rock. I mean, it's just the breadth is so amazing, but if it's written by him, I just don't care. If it was a book on chopsticks, I'd be like, absolutely, I'll read a 200-page, 300-page book on chopsticks written by John McPhee.

• 1:02:38Ryan Holiday?

  Right. I love, he has that one, uh, Control of Nature that's really fascinating. It's just about like, it's like about the Mississippi River, some volcano in Iceland, and like the hills of Los Angeles. And you're like, this should not be fascinating, but like, I'm hanging on every word because you're so good.

• 1:02:58Tim Ferriss?

  Oh, it's so, it's so good. I mean, chances are, he's been writing for so long. He's been a staff writer at The New Yorker for decades and decades and decades. I think he's gotta be in his 70s or 80s even now. But I remember researching The Four Hour Chef, and I was like, I bet there's something that McPhee has written on cooking and food, and I bet it's gonna, and I bet it's gonna be one of the best pieces in the English language. And lo and behold, there is this piece from sometime in the maybe 80s called Brigade de Cuisine, written about this tiny restaurant in New York and just this maniac executive chef. And it was, it's like, all right, there we go. Like, yep, the best I've ever read about cooking or food. And of course, it's John McPhee. Yeah.

• 1:03:41Ryan Holiday?

  Totally.

• 1:03:42Tim Ferriss?

  What's, uh, what are some of your goals for this year? I'm just, I'm very curious to know if, if, do you believe in resolutions that are long-term resolutions? Is it tiny habits, day by day? I mean, what are some of your goals, whether for this year or, or shorter term? I mean, how do you, or longer term for that matter?

• 1:04:06Ryan Holiday?

  Uh, sure. Yeah. Um.

• 1:04:10Ryan Holiday?

  I don't know. Uh, I, it's not that I don't believe in goals. It's actually been a weird, this sounds, I'm sure like a humble brag, but it's a genuine problem. So, uh, or a first world problem. Like, like I, I wanted to write books. Like, that's what I wanted to do. And, um, I like, I wanted to be a writer. That was my, my.

• 1:04:27Tim Ferriss?

  That's what you wanted to be even growing up? Is that what you thought you were doing?

• 1:04:31Ryan Holiday?

  Yeah. And so to, I accomplished it very early and, and now it's, it's, it's like, okay, now what? And, but there's, I don't have like, well, now I want to be the biggest author in the world. Like part of, one of the benefits and then also consequences, I guess of Stoicism is that it's very humbling. And it, it sort of helps filter out like very selfish or materialistic goals, I would say. So like, I'm not like, oh, I wanna, I wanna have millions of dollars. I wanna have hundreds of millions of dollars. Like, it, it's like, but I'm quite comfortable. I would like to continue to be comfortable, but like that, that ambition is somewhat sated.

• 1:05:10Ryan Holiday?

  Um, I'd, I'd like, I have more book ideas, so I'm, I'm in the process of thinking about and potentially selling another book. Um, but I'd like it to take longer and I'd like to challenge myself in ways that way. Um, I think, um, you know, I've, I've, uh, I may get married. Well, I'm engaged. I'll probably get married this year. So that's like something, I, I think, like in a lot of ways.

• 1:05:34Tim Ferriss?

  I would hope you would have some plans for getting married. Or if there was just like, no, I figured out the engaged part, but I'm not sure on the marriage part.

• 1:05:41Ryan Holiday?

  Right. Well, no, it's, it's like.

• 1:05:42Tim Ferriss?

  It's like a hold option.

• 1:05:44Ryan Holiday?

  Yeah, right. Right. Now I, now I've got some time. Uh, I bought myself some time. Um.

• 1:05:51Tim Ferriss?

  The option agreement with your girlfriend.

• 1:05:54Ryan Holiday?

  I locked it down and now, now I'm just gonna wait. Um, no, it's, I think I would like to focus on like less sort of external goals and maybe more internal goals. Just like, you know, I, I think we're, I don't think there's anyone out there that's like, I'm exactly as like low stress as I want. I'm exactly as sort of like kind or forgiving as I want. I'm exactly as, you know, like, um, happy, like I, I'd like to focus on sort of internal, personal, um. Stuff i- in in terms of adjust like integrating and adjusting all the things that have come into my life over the last few years.

• 1:06:36Tim Ferriss?

  Yeah.

• 1:06:36Ryan Holiday?

  Into the kind of like everyday norm that I would like. So it's it's not a specific thing. And that might hold me back in some ways, but I I think it's it's less about like sort of external publicly validated success and more about just like. All right. Is this the person that I want to be? Well, kind of, but here are three or four things I would fix. Well, like, let's focus on those.

• 1:06:59Tim Ferriss?

  Right. So two two related questions that are follow ups. The first is. If you if you want to be a writer and you write a lot, you mentioned one of the problems with a lot of writers is they just don't have anything to say. How does one? Go about having something interesting or meaningful to say and have you do that? Uh, let's let's begin with that and then.

• 1:07:22Ryan Holiday?

  Oh, sure.

• 1:07:22Tim Ferriss?

  And then I have a question about working on internal goals.

• 1:07:25Ryan Holiday?

  Sure. So the the best writing advice I ever got, and I think it came from Tucker, but I don't remember. But it's someone asked him like, how do you become a writer? And he said, writers live interesting lives. And that's how you find something to say, like you go and do interesting and yes, this is true for fiction or nonfiction. Go do interesting things, experience the world and develop some sort of perspective or knowledge or um. Wisdom that you can pass along through your writing. So the four hour work we came from your experiences running a company and then. Deciding to travel.

• 1:08:05Tim Ferriss?

  Love.

• 1:08:06Ryan Holiday?

  And, you know, my first book, Trust Me, I'm Lion, came out of my experiences in. Marketing and doing a specific kind of marketing and having a sort of existential crisis that came along with that. Um, and this book came out of my studies and experiences, you know, like researching and reading and just living my life in a. In a high pressure, high stakes environment. And I know that seems weird.

• 1:08:31Ryan Holiday?

  But just like the best marketing decision you can make for a product is to like have a really good product that people want, the best way to have writing that people want is to live a life and have experienced the world in a way that allows you to communicate something to people that they've never heard before. And, and I think it's actually especially true in fiction because you're like, at least in nonfiction, you can like, someone could go out and study and objectively find, like academics can write good nonfiction books, um, based on their research. But nonfiction, you have to be able to communicate all these intangibles to the reader.

• 1:09:12Tim Ferriss?

  You mean fiction?

• 1:09:14Ryan Holiday?

  Yeah, sorry, in fiction, yeah. You have to communicate all these intangibles about life and about relationships and about how the world works. And if you haven't gone out and lived it and experienced it, you're at a distinct disadvantage when it comes to communicating those things because it's like, you're like the forty year old virgin who's trying to like, talk about sex.

• 1:09:34Tim Ferriss?

  Right, like a bag of sand.

• 1:09:35Ryan Holiday?

  Yeah, exactly. You can fake it, you can fake it until you say something that's so obviously wrong that just everyone in that instance knows that you have no idea what you're talking about.

• 1:09:51Tim Ferriss?

  Yeah, good point. And I mean, that's been really my, uh, maybe way of compensating for what I perceive as a very imperfect writing style. And I don't think that I am the best writer out there. I view myself as a teacher first and foremost. So my cheat has been to follow in the footsteps of someone like George Plimpton, uh, who was a really fascinating character, who was the editor of the, the Parish Review and really popularized what he called participatory journalism, where he would go become a professional football player for a season. He would go try to join the circus for a season. He would go try to box three rounds with Archie Moore, for instance.

• 1:10:30Ryan Holiday?

  Right.

• 1:10:30Tim Ferriss?

  And then write about the experience. And you do not need, just to underscore what you said, you do not need to be a college educated, uh, wordsmith to have compelling writing if you have a good story to tell. It's just that simple. And, uh, you know, I remember talking with Tucker about this, uh, and a lot of it really just comes down to. I think writing in a natural voice, basically writing as you are, which takes practice, but having a good story to tell. Um, working on, actually, before I get to the internal goals, what does financial security mean to you? How do you define that for you, for yourself personally?

• 1:11:16Ryan Holiday?

  Uh, are we talking like specific numbers? Or are we just talking about like, what is, what is financial security sort of generally?

• 1:11:22Tim Ferriss?

  You know, I, but you know, both, to the extent that you're comfortable. I mean, it's, uh,

• 1:11:27Ryan Holiday?

  Sure.

• 1:11:27Tim Ferriss?

  You know, it's whatever you're comfortable talking about. It's just that I think this is such a huge, uh,

• 1:11:36Tim Ferriss?

  piece of so many decisions that people make, um, bad and good.

• 1:11:42Ryan Holiday?

  Right.

• 1:11:42Tim Ferriss?

  I'd be curious to know how you have resolved this for yourself to the extent that you have.

• 1:11:47Ryan Holiday?

  Sure. Well, I guess there's a couple of ways to be rich, right? One is have a lot of money so you can buy a lot of stuff. Or the second, or like, if, if you sort of express being rich as being able to buy whatever it is that you want, right, whenever you want it, there's two ways to do that. One is to have tons of money, or two is to not want as much stuff, right? And so I think if you meet somewhere in the middle where you, you sort of, you keep your tastes under control.

• 1:12:14Ryan Holiday?

  Like, for instance, like, I don't fly first class. I could afford it, but I don't fly first class because, and I have before, but the, the point is like, I just don't want to get in a habit of flying first class because now it means like, if I want to travel somewhere, it's going to cost me X amount.

• 1:12:29Tim Ferriss?

  Right.

• 1:12:29Ryan Holiday?

  And I'm going to have to do things that I maybe don't want to do to be able to get that money.

• 1:12:35Tim Ferriss?

  Right.

• 1:12:35Ryan Holiday?

  And I'm going to make decisions for the rest of my life around that assumption. And I don't want to have to do that. So it's like, how do you, how do you limit what you, like, there's that quote from Paul Graham about keeping your identity small. If you can keep your tastes at a level at which, um, a reasonable salary or financial situation covers it, then you don't need to go out and.

• 1:13:03Ryan Holiday?

  Do certain things for money that other people do like. I've like to me, financial success is like I I have a house that I live in that's nice. That I can keep my stuff in that I have my books in. But I don't have like six spare bedrooms that I needed to fill up with furniture. Because I wanted to send a message to people that I have a really nice house, you know?

• 1:13:25Tim Ferriss?

  Right.

• 1:13:25Ryan Holiday?

  Um, and I don't live in New York City because I don't need to live in New York City. And which means that I spend a lot less just to have the same thing, you know? Um, and like I it's like, can I can I go to a nice steakhouse and buy whatever I want? And not care what the check is to me, that's being financially secure and about sort of what I need. To not care about money.

• 1:13:50Tim Ferriss?

  Mm hmm. Got it.

• 1:13:52Ryan Holiday?

  Um, and so like, and then I think the other it's not just being financially smart on your spending, but like. You know, do you actually understand like investing and managing your money in a smart way? So it's not, you know? Like there's all these people, I I'm sure you deal with investors uh or. Startup founders or whatever who have like credit card debt. And it's like, why are you trying to like invest in startups when you could just make? Thirteen percent more a year by not paying off your by not like having carrying a credit card balance? You know what I mean?

• 1:14:26Tim Ferriss?

  Right.

• 1:14:27Ryan Holiday?

  Um, so I think just sort of basic financial responsibility and management helps you. Helps you make what you're doing go further. Um, so like that's been beneficial to me. Um, but there you know, there's the study about, um, you know? If you make more than any amount over seventy thousand dollars a year does not correlate with any increased amount of happiness. Um, I think that's definitely true, having made a lot more than seventy thousand dollars a year and a lot less. Um, so for me, it's like, you know, somewhere somewhere above that is happy and comfortable. Um, and the rest should just be.

• 1:15:07Ryan Holiday?

  Should be saved and managed like the Stoics say for a for a much worse time because you never know what's gonna happen. Don't don't spend the money you make because you might not have it and you might want it some other time.

• 1:15:21Tim Ferriss?

  Sage advice, yeah, it's hard to, hard to predict, nay, impossible to predict when the next black swan will hit.

• 1:15:29Ryan Holiday?

  Totally.

• 1:15:30Tim Ferriss?

  And you know, I've been thinking a lot about this, not to turn, not to misdirect the conversation, but the fact that much like human action and climate change, uh, technology in a sense, has led to, uh, super storms, um, let's say storms of the century, perhaps happening as often as every three to 20 years now, uh, which was, uh, a recent, um, recent piece that came out of MIT, the, uh, the instant, instantaneous, uh, sort of, uh, dissemination of hysteria through social media, I think greatly increases the probability of

• 1:16:12Tim Ferriss?

  higher frequency black swans, because everything is so interconnected and humans are, uh, for better or for worse, certainly in large numbers, pretty irrational masses, uh, and I just feel like, if anything, you know, these, these sort of once a century, twice a century, stock market crashes and so on, are probably going to happen more often, um, but that's pure speculation on my part.

• 1:16:37Ryan Holiday?

  No, no, I, I think it makes sense and it's like, look, do you wanna, like what, I, I quote this in the book, there's the line from, um, uh, Warren Buffett about being greedy when others are fearful and being fearful when others are greedy, and we definitely live in a time where people are very greedy. Um, and I think it's, I think it's really important too, that you, you don't at all correlate being financially successful with worth as a person, um, so the fact that, you know, I know someone who's worth X million, and I know someone who's worth, you know, less than nothing, doesn't say anything about their value to me as people and

• 1:17:18Ryan Holiday?

  how I should respect or treat them, and if you can keep that in mind, you won't feel like the fact that so and so is making, you know, eighty thousand dollars a month on info products, it doesn't, like, I know this, but it doesn't make me care about making info products, like, I wanna write my books because they pay me enough to be happy, and that's what matters.

• 1:17:41Tim Ferriss?

  So, speaking of, uh, sort of valuing people and different people.

• 1:17:48Tim Ferriss?

  Uh, this and the, the, uh, feel free to answer this however you like. For, for your circle of friends. Number, number one, you know, these days, how do you curate them, right? If it's not on net worth, which I agree it shouldn't be.

• 1:18:05Ryan Holiday?

  Right.

• 1:18:07Tim Ferriss?

  How do you curate your friends that you end up being the average of, right? As a group? And over, over time, let's just say over the last five years, 10 years, what has become more important, less important? More important or less important?

• 1:18:23Ryan Holiday?

  It's weird. I think a big part of it is keeping like toxic, unhealthy people out of your life. Like people who have drama and problems and pathological issues. I think those are important people, not only not to be friends with, but to, you know, extricate yourself from as much as possible. So that's something I've thought a lot about. I like people who make me laugh. I think that's important. I think people who, uh, I don't have to try to impress. Like it was weird. One of my friends from high school was in town like over the weekend. And it was like, I don't think we talked about like work at all. Because, uh, he was doing his thing and I'm doing my thing. And what matters is that we have like a shared history or a thing that we relate over.

• 1:19:08Ryan Holiday?

  And so to me, like, I don't know about you, where, when your work is also tied up in your personal relationships, I really value people who I can exist in the present moment with. So it's like, I can do something with them. I can have a conversation with them. And it doesn't, like, the fact that, you know, they do this and I do this is irrelevant. And the fact that they live here and I live here is irrelevant. I, I look for people that like, and I may have gotten this for you is, is like, the idea of someone you can sit and have a nice, long dinner with. To me, that's, that's a friend, not someone I have to meet at a bar or, you know, any other context.

• 1:19:54Tim Ferriss?

  Makes perfect sense. If you had to pick, let's do just a couple of rapid fire questions.

• 1:20:01Ryan Holiday?

  Okay.

• 1:20:02Tim Ferriss?

  And one to think on, just as we're doing this, is I'd like to hear a story of what Ayesha Tyler calls self-inflicted wounds. So just like a ridiculous story, a debacle, a fiasco of some type that was self-created. Sometimes that's involving alcohol for people. That doesn't have to be true for you, since I don't think I'm not sure if I've ever seen you drink alcohol. But, okay, first one, what is your, what would be your theme song or your like ring entrance music if you had to choose one?

• 1:20:38Ryan Holiday?

  Ah, um, I, let me pull up iTunes, let me see if I have anything. I don't know, I like Iron Maiden. If I had to pick like an awesome entrance song, probably something from Iron Maiden.

• 1:20:50Tim Ferriss?

  Okay.

• 1:20:53Tim Ferriss?

  If you could change one thing about yourself, what would it be?

• 1:20:56Ryan Holiday?

  Um, this is ironic, I don't love my voice that much.

• 1:21:00Tim Ferriss?

  Hmm, I feel the same way, not about your voice, but about mine.

• 1:21:05Ryan Holiday?

  Do you think there's any, like, anyone who's not like a narcissist that enjoys the sound of their own recorded voice?

• 1:21:13Tim Ferriss?

  I haven't yet met them, but I'm sure they exist.

• 1:21:16Ryan Holiday?

  I heard it's actually because you hear your voice differently. Like, apparently it's like when you're just talking, the voice that you hear is different than like how it's recorded and that that's, it's just the difference that makes you feel bad about yourself.

• 1:21:31Tim Ferriss?

  Uh, you know, that's an enabling belief, so I'll take it.

• 1:21:35Ryan Holiday?

  Sure.

• 1:21:36Tim Ferriss?

  Thanks for that. When you think of the word successful, who is the first person who comes to mind and why?

• 1:21:43Ryan Holiday?

  Uh, no one comes to mind. Well, I talk about John D Rockefeller in the book, so there's an example, one of the world's richest men.

• 1:21:51Tim Ferriss?

  Got it, alright.

• 1:21:56Tim Ferriss?

  If you could study a new subject with any expert in the world, who would it be and what would you study?

• 1:22:02Ryan Holiday?

  Like a new subject or just a subject different than the one that I study?

• 1:22:06Tim Ferriss?

  By new, I mean new to you. So yeah, different from what you've already immersed yourself in.

• 1:22:14Ryan Holiday?

  Yeah, I think I'd love to do like archaeology or something like that. I don't know a specific person, but some sort of ancient site or dig would be fascinating to me.

• 1:22:25Tim Ferriss?

  And you spent time in Rome looking at like the burial site of Seneca and so on, is that right?

• 1:22:33Ryan Holiday?

  Yeah, yeah, I spent some time in Rome when I was finishing up the book and I just went to like the sites and stuff that are that are in the book for sure. And I was in Dublin, I was in Dublin like two weeks ago. You'll love this, they took us into this crypt, like a like a burial site that preserves the bodies. And they had these mummies there from like the 12th century and they let us touch them.

• 1:22:55Tim Ferriss?

  Wow.

• 1:22:56Ryan Holiday?

  I was like, we are a long ways from America.

• 1:23:01Ryan Holiday?

  We touched the hand of this guy who died in the Crusades.

• 1:23:04Tim Ferriss?

  Wow, yeah, that's, that would definitely be cordoned off in the US.

• 1:23:11Ryan Holiday?

  I think so, yeah.

• 1:23:12Tim Ferriss?

  Do not chew on the mummy.

• 1:23:15Tim Ferriss?

  If you could offer your younger self one piece of advice, what would be? Let's, let's, let's place that. Younger self, freshman in college.

• 1:23:24Ryan Holiday?

  Relax.

• 1:23:25Tim Ferriss?

  Relax. Why?

• 1:23:28Ryan Holiday?

  Every young person that I, I think you probably get this too, every young person that I talk to, I feel, especially like an ambitious one that seems to want to talk to me, I feel like they're on the verge of like a nervous breakdown or an explosion of some kind.

• 1:23:42Ryan Holiday?

  Because everything is so serious to you when you're that age. And I think it maybe it's our parents that did it to us or whatever, but I, I feel they're like, you know, if I, I gotta do this or like I'm gonna die. Like, it's like, everything feels like, like an issue of life or death, you know? And it's so the opposite of that. It's like, you are, you could, in, in all of history, you are in the safest, most like,

• 1:24:08Ryan Holiday?

  nerf, like, bumpered area that has ever existed. Like, you, you could do anything short of murder and you're probably gonna be fine. You know what I mean? Like, you have unlimited time, like, just relax, take it easy. You're not gonna care about this in a little bit of time. And that's probably what I would tell myself.

• 1:24:29Tim Ferriss?

  So just, just to take a quick sidebar from the rapid fire. You dropped out of college. I feel like there is a, there is a survivorship bias in media that leads to a romanticizing of dropping out of college. And I'd love to hear your thoughts on who should, who you would advise to drop out of college, who you would advise to stay in college. Because you ended up very uniquely, in my experience, extremely well-read and extremely well-rounded. And when people drop out of college, oftentimes they say, well, it's because it's not going to prepare me for job X or Y or Z.

• 1:25:10Tim Ferriss?

  In my opinion, at least in a liberal arts college, still is that the goal is not to prepare you for a single career. The goal is to make you a well-rounded, developed human being. So I'd just be curious to know

• 1:25:22Ryan Holiday?

  Sure.

• 1:25:23Tim Ferriss?

  what your caveats are, who you would recommend, consider dropping out versus not.

• 1:25:28Ryan Holiday?

  Yeah. So it's funny. I was looking at that. There's a Wikipedia page that's like a list of college dropout billionaires.

• 1:25:35Tim Ferriss?

  Right.

• 1:25:36Ryan Holiday?

  And it's funny. It's like, yeah, it's the definition of the survivor bias because there's like, let's say there's 500 billionaires in the world. And like 20 of them were college dropouts. That means even among billionaires, most of them went to college, right? So, um, but you only, you only care about the ones who dropped out of college. So, um, I think like for me, dropping out of college was, it was a pretty simple calculation. It was, am I drop it like, would I stay in college and graduate and hope to have this same opportunity? That I'm being offered right now.

• 1:26:09Tim Ferriss?

  And the answer was Which, yeah. And that was the Tucker opportunity.

• 1:26:12Ryan Holiday?

  It was Tucker, Robert Greene, and then working for Aaron Ray, who we both know at the collective in Hollywood. So it's three things that in, either one of them individually, I would have killed for as a post-grad job. And so I said, you know, I'm going to do this now and see how it goes. What I think people, the problem with dropping out of college that everyone misses in the discussion is that dropping out of college is not a thing. You take a leave of absence from college, meaning you can go back at essentially any time. Um, so the it's it's again, when I'm saying like relax to the nineteen year old version of me or whatever.

• 1:26:53Ryan Holiday?

  It's like, dude, it's not as it's not as black and white as you're making it out to be like. Take risks, you're you're in a cohort where you can absorb risk. And that and then understand that you're not going to starve to death if this goes poorly like. For me, it was like, I'm going to take advantage of this. And a year from now, if it's not working out, I'm going to go back to college because college is the best default option. If you don't know what you want to do. Because it keeps you on the level with everyone else. And it gives you some sort of certification that sets you apart from like people who didn't go to college. Um, so so that's how I think about college and usually, um.

• 1:27:37Ryan Holiday?

  The and I'll say this, the people who should not drop out of college are the people who are doing poorly in college. Because college is exactly like life, it's a system that you have to figure out how to get the most out of. And do your best at, and if you're failing out of college, you're probably going to fail at life. Because you are it if you don't address the root reasons why you're doing bad at college, you know?

• 1:28:02Tim Ferriss?

  Yeah, so yeah, learn, learn to learn to game the system while you still have headgear on before.

• 1:28:09Ryan Holiday?

  Exactly.

• 1:28:12Tim Ferriss?

  Cool. All right. I appreciate that because it's it's something that I get asked about a lot. Uh, so it's it's nice to have your input. All right, let's so back to.

• 1:28:21Ryan Holiday?

  And one one other note on that, it's like very, I I always hear from people, it's like, I want to leave college so I can travel. Or I want to go to college so I can like start a company or get a mentorship. And it's like, these are not things that you have to leave the womb to do, like you can do them in college.

• 1:28:37Tim Ferriss?

  Right.

• 1:28:37Ryan Holiday?

  And so if it it should be, you should leave college if you have an opportunity to do something. That can only be done outside of college and if you will kill your you will kick yourself. If you let that opportunity pass and it doesn't come back your way again when you're graduating.

• 1:28:56Tim Ferriss?

  Yeah, and that's a great point, actually, I think that it would be very fascinating to look at billionaire dropouts. And see how many of them. Had started the company that was going to later make them a billionaire and proven to themselves that it had very real legs and a time-sensitive window before they dropped out. Because I think the percentage is probably very high.

• 1:29:20Ryan Holiday?

  Right, that's what Zuckerberg did.

• 1:29:21Tim Ferriss?

  Yeah, yeah, and many others.

• 1:29:25Tim Ferriss?

  Awesome, so we'll take just a little bit more time. I'm gonna do a couple of rapid fires so people get to know you and not just your thoughts on Stoicism. Alright, so you walk into a bar, what do you order from the bartender?

• 1:29:38Ryan Holiday?

  If it's in Austin, I order Topo Chico, which is like a Mexican sparkling water. If it's not Austin, I'll probably just get soda water with lemon and lime or cider.

• 1:29:48Tim Ferriss?

  Do you ever drink?

• 1:29:50Ryan Holiday?

  Just cider, it's the only thing that I like.

• 1:29:52Tim Ferriss?

  Got it, so it's not a moral decision, it's a taste decision?

• 1:29:56Ryan Holiday?

  It's a little of both, but yeah.

• 1:29:58Tim Ferriss?

  Okay.

• 1:30:03Tim Ferriss?

  What makes Mexican sparkling water different from normal sparkling water, I have to ask?

• 1:30:07Ryan Holiday?

  I just like it better than Pellegrino, but I will say that I fully embrace the ridiculousness of eating or of drinking imported water from Mexico.

• 1:30:18Tim Ferriss?

  Especially Mexico, alright.

• 1:30:20Ryan Holiday?

  Right.

• 1:30:21Tim Ferriss?

  Who is your favorite person to follow on Twitter? Or, and you can give two or three if you'd like.

• 1:30:28Ryan Holiday?

  I like Fake Jeff Jarvis, who I think is hilarious.

• 1:30:34Ryan Holiday?

  I like Felix Salman a lot.

• 1:30:36Tim Ferriss?

  Who is Felix?

• 1:30:37Ryan Holiday?

  Felix Salman, he's a blogger for Reuters.

• 1:30:40Tim Ferriss?

  Got it.

• 1:30:41Ryan Holiday?

  And then, I don't know who else. Oh, Media Redefined by Jason Hirshhorn is a pretty good Twitter feed to follow.

• 1:30:52Ryan Holiday?

  Oh, and Maria Popova of Brain Pickings.

• 1:30:55Tim Ferriss?

  Yeah, yeah, that's a great site. Speaking of sites, uh, what sites do you visit on a regular basis?

• 1:31:02Ryan Holiday?

  Um, I don't visit a ton of sites. Uh, I use my RSS reader. Um, so I use Feedly. Um, where I subscribe to a bunch of, uh, feeds. Felix is one of my favorite. I like Ta-Nehisi Coates who blogs for The Atlantic. Um, I, I like Mark Cuban's blog a lot. Um, I, I think Reddit, if you, if you, um, subscribe to the right subreddits is a really good way to get like sort of highly curated news.

• 1:31:31Tim Ferriss?

  What subreddits do you subscribe to?

• 1:31:33Ryan Holiday?

  Uh, Stoicism is a good one.

• 1:31:35Tim Ferriss?

  Besides not suitable for work.

• 1:31:37Ryan Holiday?

  Yeah, sure. Uh, Sto- Stoicism is a good one. Um, uh, philosophy is a decent one. Uh, history porn is a pretty good one, uh, which is just like old photos from history.

• 1:31:49Tim Ferriss?

  Yeah.

• 1:31:49Ryan Holiday?

  Um, Ask Historians is my favorite. So smart people, uh, like people ask unusual questions about history that only like academics or historians answer. Um, Today I Learned is a great one where it's just like a fact, uh, that, you know, people was unexpected. Um, I like First World Problems. I think that's a funny one. Um, and then is there, is there any, uh, there's, there's one about civil war. There's one about writing. And then I like Reddit Books as well.

• 1:32:19Tim Ferriss?

  Yeah. Reddit Books is big.

• 1:32:21Ryan Holiday?

  Yeah.

• 1:32:22Tim Ferriss?

  Uh, the, what is the first face that comes to mind when you think punchable?

• 1:32:28Ryan Holiday?

  Punchable? Uh, I don't know. That's a good question though. Um.

• 1:32:35Tim Ferriss?

  We can, we can come back to that. It could be, it could be fictional character too, if you'd like.

• 1:32:39Ryan Holiday?

  Sure.

• 1:32:40Tim Ferriss?

  Uh, dogs or cats?

• 1:32:42Ryan Holiday?

  Uh, dogs, of course.

• 1:32:44Tim Ferriss?

  Why?

• 1:32:45Ryan Holiday?

  Uh, cats are just an animal that lives in your house.

• 1:32:50Tim Ferriss?

  Got it. And okay, so elaborate on dogs because you you said something to me that I I was hoping to have you elaborate on.

• 1:32:58Ryan Holiday?

  Yeah.

• 1:32:58Tim Ferriss?

  Was that dogs, you think dogs make you a better person. I was curious how you think they make you a better person.

• 1:33:03Ryan Holiday?

  Dogs exist totally in the moment. Um, dogs are the definition, I think, of sort of unconditional affection. I think it's really interesting to have an animal that evolves to live and depend on humans, the way that dogs did, like dogs. They think were domesticated because they like wolves would come and eat scraps from the um, like the campfire. And basically, we slowly selected the the most sort of docile, friendly. You know, mischievous of the of the animals and and that's where dogs come from. Um, so I I think dogs are dogs are great because they're this thing that's dependable.

• 1:33:43Ryan Holiday?

  They're this thing that depends on you and and needs you, but at the same time, you can never, you can never truly disappoint. Um, so it's this great sort of metaphor for life. I think it's just great practice. Um. And plus they're super cute and they do like hilarious things. I have two pet goats also. I don't know if I told you this, but I.

• 1:34:03Tim Ferriss?

  No.

• 1:34:04Ryan Holiday?

  I I have two goats, which are pretty funny. They're like really dumb dogs.

• 1:34:09Tim Ferriss?

  Do you do you milk the goats or do you just have them for for comedic effect?

• 1:34:13Ryan Holiday?

  Just mostly for comedic effect. I like, I don't, like, people have asked that, but I just don't have that much need for goat's milk. So, um, it's not, you have to breed them to get, uh, because they're Nigerian dwarf goats. So you have to breed breed them to get milk, which I'm not really interested in doing.

• 1:34:31Tim Ferriss?

  Sounds really low yield. It's kind of like milking cats.

• 1:34:34Ryan Holiday?

  Right. Like, what do I need? Just, I then I'm just this guy who's always trying to pawn goat milk on people like. Let me give you some.

• 1:34:42Tim Ferriss?

  Right, right.

• 1:34:43Ryan Holiday?

  Like the friend that has an orange tree.

• 1:34:45Tim Ferriss?

  Nigerian dwarf goat milk sounds.

• 1:34:50Tim Ferriss?

  That could become a thing in San Francisco. You could export.

• 1:34:52Ryan Holiday?

  Probably.

• 1:34:53Tim Ferriss?

  Yeah. What book are you most likely to give out as a gift?

• 1:34:57Ryan Holiday?

  Um, probably Meditations. God knows how many copies I have gone through. And then the second one would be The War of Art by Steven Pressfield.

• 1:35:06Tim Ferriss?

  Yeah, it's a great book.

• 1:35:08Tim Ferriss?

  Uh.

• 1:35:10Tim Ferriss?

  Let's see. What movie can you not resisting if it's on, assuming that you had a TV in an imaginary world?

• 1:35:17Ryan Holiday?

  Well, of course, I have a TV. I'm not a weirdo. Um. I love TV. Um, I prob- probably, uh, Gladiator, um.

• 1:35:27Tim Ferriss?

  It's appropriate.

• 1:35:29Ryan Holiday?

  I like, uh, Spinal Taps, one of my favorite movies.

• 1:35:32Tim Ferriss?

  Have you seen Shaun of the Dead?

• 1:35:34Ryan Holiday?

  No, I haven't.

• 1:35:35Tim Ferriss?

  Oh, my god. You have to see Shaun of the Dead. S H A U N.

• 1:35:40Ryan Holiday?

  Okay.

• 1:35:41Tim Ferriss?

  It it might become one of your favorite movies. It is.

• 1:35:44Ryan Holiday?

  Alright.

• 1:35:45Tim Ferriss?

  It is splendid. I wrote about half of the four hour work week with that on repeat on a TV.

• 1:35:51Ryan Holiday?

  Yeah, I don't know how you do that. I had to have total, total silence.

• 1:35:54Tim Ferriss?

  Well, here's the, here's where I am Emmy weirdo, uh, among many other ways, is I, I would play the movie because I tend to write late at night and I, it's easy to feel isolated and crazy and like

• 1:36:06Ryan Holiday?

  Oh.

• 1:36:06Tim Ferriss?

  Nicholson in The Shining.

• 1:36:09Ryan Holiday?

  Right.

• 1:36:09Tim Ferriss?

  If, if you're always by yourself, at least for me, so particularly without any dogs or anything around or people. Uh, so I would put the movies on with characters that I liked and I would mute the TV and then listen.

• 1:36:21Ryan Holiday?

  Okay.

• 1:36:21Tim Ferriss?

  Listen to music while that is just

• 1:36:24Ryan Holiday?

  Interesting.

• 1:36:25Tim Ferriss?

  Motion, human forms in motion in the background. Uh. Oddly enough, yeah, just, just a habit that I have. Uh. Let's see. Uh, who was your first celebrity crush, if you've had one?

• 1:36:40Ryan Holiday?

  Celebrity crush?

• 1:36:41Tim Ferriss?

  Or, or current celebrity crush? Any celebrity crush?

• 1:36:46Ryan Holiday?

  I don't know. Um, I really don't know.

• 1:36:49Tim Ferriss?

  Nicolas Cage?

• 1:36:50Ryan Holiday?

  Yeah. I'm a big Nicolas Cage fan.

• 1:36:54Tim Ferriss?

  Uh, do you cook?

• 1:36:56Ryan Holiday?

  Uh, like, I cook bacon.

• 1:37:01Tim Ferriss?

  Okay, I can't end on that question and answer. Uh, if you could choose, uh, three people, let's just say, living people.

• 1:37:12Ryan Holiday?

  Okay.

• 1:37:13Tim Ferriss?

  To be your sort of, uh, circle of advisors or elders to help you with major decisions, who would they be?

• 1:37:22Ryan Holiday?

  It's weird, like, so I've gotten an iteration of that question where it's like, oh, you've worked with all these people. Who else would you want to work with that you haven't?

• 1:37:30Tim Ferriss?

  Yeah.

• 1:37:30Ryan Holiday?

  And I, it's weird, I feel like very fortunate that I have in, like, Robert Greene is one of those sort of most respected, you know, uh, strategists about power and life and, and history. And like, he's someone that I call when I have questions about stuff. Um, you know, I, I, I think you're one of those people that I, that I call and you're, you know, a world renowned writer and marketing expert and an investor. Um, and then the, the third person is my, is my girlfriend now fiancee, who I think is really good at sort of reading people and, and more importantly, she, she knows me and like what my weaknesses or issues are. Um, which I think is really important. It's not just about like, you know, objectively what the best thing to do in a situation is.

• 1:38:14Tim Ferriss?

  Absolutely.

• 1:38:15Ryan Holiday?

  It's, it's like, what, what, what can you do given your constraints or tendencies? Like, oh, you should totally take this job. Well, you know, if you're someone who's pretty flaky, that's not a great, you know, that's not great advice. Like, it's, it's oftentimes, it's, you know, what you can do with your, taking you as, as a person for granted, who's gonna behave how you've always behaved, you can have someone who understands you well enough to give really good advice. I think that's super important.

• 1:38:46Tim Ferriss?

  So I think that is a great note to wrap up on. How can people better or best get to know Ryan Holiday? Where should they find you online? What should they read of yours?

• 1:38:57Ryan Holiday?

  Sure.

• 1:38:57Tim Ferriss?

  Give us some suggestions so that people can dig a little deeper, which I hope they do.

• 1:39:03Ryan Holiday?

  Yeah, so my website is ryanholiday.net. I'm Ryan Holiday on Twitter. I suggest people start with the books too, because I put myself into the books. So, The Obstacle is the Way, Trust Me, I'm Lying is my first book. I have a book called Growth Hacker Marketing, which started as a Kindle book, and now it's going to be a paperback. And then I write almost weekly for Thought Catalog. And then I'm the editor-at-large of The New York Observer, where I have a series of columns about media and life and other things there.

• 1:39:35Tim Ferriss?

  Fantastic. Well, Ryan, thanks for the time. Always nice to chat. And this gives me an excuse to sort of ask you 20 questions in a way that isn't totally socially weird over a meal.

• 1:39:49Ryan Holiday?

  This was amazing.

• 1:39:51Tim Ferriss?

  Yeah, this was super fun. I'm sure I'll talk to you soon. So, thanks for taking the time.

• 1:39:56Ryan Holiday?

  Yeah, thanks for having me.

• 1:39:57Tim Ferriss?

  All right, I'll talk to you soon. Bye.

• 1:40:04Speaker 02

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• 1:40:13Speaker 02

  Where you'll find an award-winning blog, tons of audio and video interview stories with people like Warren Buffett and Mike Shinoda from Linkin Park, the books, plus much, much more. Follow Tim on Twitter at twitter.com/TFerriss. That's T-F-E-R-R-I-S-S. Or on Facebook at facebook.com/TimFerriss. Until next time, thanks for listening.