When ‘genius’ becomes a trap, with author Ryan Holiday

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0:40Get up to$100 ,000 in AWS credits and a free SOC2 consult at startups.aws. Great leaders, you know, a Lincoln or something assembles a team of rivals versus a team of yes men. And these are things that we have a lot of precedent over historically. You think you want freedom of movement and supporters and advocates, But actually what you need is to be challenged. And you need boundaries and you need limitations. Ryan Holiday has made it his mission to bring the wisdom of ancient Stoic philosophers, such as Roman Emperor Marcus Aurelius, into modern life. Ryan believed the Stoics unlocked the source code for leading a meaningful life, the four virtues.

1:33We know what courage is, right? Courage is when you brave danger. But then what danger? Why? To whose benefit? Well, now you're dealing with justice. And then where's the line between courage and recklessness? Well, now you're talking about discipline and temperance. And then how do you know what the right amount is? Well, now we're talking about wisdom.

1:58You got to have incredible talent at every position. It's like this huge push. There are fires burning when you're going home. Can you believe it? Such an idiot. And then you go back to, this is totally going to be amazing. There are so many easy ways. I have no idea what to do. Sorry, we made a mistake. But you have to time it right. Oops. Working out of a three-bedroom apartment. Stuff that just seems absolutely nut balls. Ten years later, we're like, well, that's just how you do it. We haven't made it just how you do it.

2:28This is Masters of Scale.

2:34I'm Jeff Berman, your host, and this week on the show, author Ryan Holiday. He has introduced millions to Stoic philosophy with his daily Stoic newsletter, podcast, and best-selling books. Ryan quite brilliantly makes the ancient Stoic ideas feel accessible and essential to our 21st century lives. Here's how he explains Stoicism in his own videos. Stoicism, if I had to summarize it in one sentence, I would say it's this idea that we don't control what happens to us in life, but we control how we respond to what happens in life. And the Stoics say that basically every situation, big ones, small ones, ones you wanted, ones you didn't want, it's all an opportunity to respond with these four virtues.

3:18Courage, discipline, justice, and wisdom. The four virtues are the focus of Ryan's latest book series. The final installment is out now. It's called Wisdom Takes Work.

3:34Ryan, welcome to Masters of Scale. Yeah, thanks for having me. Great to have you. I first encountered your work through my friend Michael Bostic, who turned me on to The Obstacles, The Way. Yeah. And I have to confess, I finished the book. I annotated the living daylights out of it. Oh, thank you. I went to our local bookstore and I went to Marcus Aurelius because I was like, well, this is like a distillation with these modern examples and it's super accessible. Like what's missing in the translation? I read a lot and I have to say I couldn't get through it. Really? Yeah. I really struggled with it.

4:09And so I'm just curious, how did you first encounter Stoicism and how did you make sense of it? Well, it's funny. I had the exact opposite experience. So someone recommended Meditations and I read it and I picked it up and I was like, this is the greatest thing I've ever read. I just didn't know that that's what philosophy could be. Sort of practical ideas and observations about, like there's this passage in Meditations where Marx Reuss talks about fighting to be the person that philosophy tried to make him. And I just, I don't know if I ever thought philosophy was trying to make you anything except confused.

4:44And that's what it is for most people. It's just these esoteric questions or riddles or probing so deep that you end up going nowhere. Like you're like, wait, so everything's meaningless and nothing matters. I just didn't know that philosophy could be practical and accessible and help you live like a good life. And what I've tried to do is sort of make that a little bit more of a bigger target for people. Ryan discovered the book Meditations by Marcus Aurelius when he was an undergraduate and became obsessed with living by stoic principles. Soon, another writer also had a profound influence on him.

5:26Ryan honed his writing and research skills by working for Robert Greene, the best-selling author of books such as The 48 Laws of Power. It distills thousands of years of power dynamics into basic tenets. I met him when I was also in college. And I started working for him, doing kind of like online stuff. And he basically showed me how to do the job. I didn't necessarily know that it was a job, that I could do the job. Like, I think for me, the idea that writers were people. There's something about when you meet someone who's actually done a thing that you've consumed that is very humanizing, I think, and very powerful.

6:14This doesn't just come fully formed out of someone's brain. There's a framework or a system or a process. And I spent almost seven years working for him, actually well into writing my first, maybe my first two books. But he was just a huge mentor to me. So that wasn't full-time, it was a part-time role? No, no. And then I worked in Beverly Hills at a talent agency, which was another kind of unique, weird experience. I was like, I'll just work for anyone doing anything cool, and I want to figure out how stuff works. What did you learn about how stuff works from working with Robert Greene? Well, Robert is kind of like a scholar monk.

6:53Basically, all he does is wake up every day and work on these books, and he works on them for incredible amounts of time. I think he's six or seven years into the book that he's working on now, which is not my process. But it was something just amazing about watching someone work on a thing where progress is going to be measured in months or years. And the sort of discipline that it takes. And then I think if anyone's read any of his and my works, the influence is very clear. What he mostly showed me is that people learn through stories. and that the job of the writer is not just to have the insight or the thing that you want to teach, but to find the best way to illustrate that in a way that's memorable and explanatory to people.

7:39So what I ended up doing in my books is I would take these Stoic teachings, which I think are pretty straightforward, pretty well said, but instead of going, you know, the Stoic said this or the Stoic said that, I would go, okay, well, what does that look like? What does it look like when someone takes this idea and tries it in the world? Like, what does it look like as a leadership principle or a productivity principle or as a principle in principle? How does that actually work? And so I learned how to do that with Robert, how to track those things down, how to find all the interesting parts of it, and then how to write it.

8:16But before Ryan could make the leap to writing about Stoic philosophy, and let's be honest, that's a bit of a tough sell to most publishers, especially from a college dropout. He decided to follow the old adage, write what you know. In his first book, Ryan revealed the secrets of marketing he'd learned in his career. It's called, trust me, I'm lying, confessions of a media manipulator. I was the director of marketing in American Apparel for a number of years and... In an era where American Apparel was quite a marketing machine. It's sad these days. I guess there's a documentary about it, But it's sad these days because it used to matter.

8:53You do these things and it's on your resume and you're like, this will matter forever. Right. And I worked at MySpace. Yeah. People don't even know that it exists. That's right. And maybe you come out the other side and eventually it comes back again. But yeah. So I had this marketing career and my first book was sort of an expose of marketing and public relations, which was a fun, interesting, dark matter of the soul for me book that I knew was always going to be a transitionary project. Like I wanted to do that book and then I wanted to write about this. Why did you want to do that book? It's not that I wanted to do this book.

9:27I felt like that was a book that only I could do. Usually you want to write about what you can't not write about. And there was definitely that. I felt like I had seen and experienced and understood how the sort of sausage was getting made in a way that was not good. And so that's what the intention of that book was. And, you know, I was writing about fake news and misinformation and all the things that have come to sort of define public discourse now, probably a tad early. Right. Before it was cool. And before there was necessarily this sort of zeitgeist around it. But I didn't want to write marketing books.

10:02I just had a book that I wanted to do. And then this is what I wanted to write about. So you could have gone on to write 10 more books about marketing and communications. You could have gone and written for Vanity Fair, writing features and essays and analysis of what's happening in the world of media and marketing. You said to your publisher, I want to write a philosophy book. So that's going to sell like gangbusters. How did you get them there? Your publisher always has an option for your second book. You have to at least run it by them. So they have the right of first refusal. So I knew I wanted to write about stoicism.

10:35And they told me later that they were just hoping, they said, we were hoping that you would just get this thing out of your system and then go back to doing marketing books. I took like a huge pickup, like 50 plus percent between Trust Me Unlying and what became the Obstacle-less Way. Because, I mean, it wasn't so much they were like, it's going to fail. It just seemed like there was a pretty low ceiling on it. And I mean, obviously, I thought there was a pretty low ceiling or I wouldn't have accepted the offer. It's always important that you're clear about the story you're telling yourself, because you can end up telling yourself a story that endows your past self with a prescience that you didn't have.

11:17I just wanted to write this book and the advance they offered was more than$1. You know, I was like, are you kidding? This is amazing. This is what I want to do. And I didn't have all these other books in mind. This was just what I was interested in and what I thought would work. And I was directionally right, but pretty open-ended with my expectations for how it would do. At this point in your journey, how had you personally implemented Stoic philosophy into your day, into your process in the lead up to the obstacles the way? Well, I certainly thought I was applying it. My wife would probably have disagreed.

11:54You look back on your younger self and you're like, what was I thinking? I was an ambitious, driven, intense person in my mid-20s. So my understanding of the stoicism that I was applying was barely in the ballpark. But I think most people, when they come to Stoic philosophy, especially if they're in a position remotely similar to mine, which is a young guy trying to make their way in the world, you're probably going to be interested in the sort of emotional regulation and the productivity, the toughness, the resilience, that kind of thing. And that was what I was mostly taking out of Stoicism.

12:30It as a sort of an ethical-based philosophy designed around virtue and public service was obviously not the most salient parts of the package. That's something I think that developed over time, not just in the philosophy itself, but I think it sort of slowly, steadily dawns on you. Do you think that that is age maturation experience? Do you think that is going through the process of studying and collecting these stories and writing it? Like what? I think it's all of that. And I also think there's kind of a hierarchy of needs. It's like, hey, when you get some of the basic stuff right, and then you're even in a position where your decisions matter or have impact, then you're like, oh, wait, let me think about these other components too.

13:16But I think, you know, at 19, when I'm reading Mark's Realist in my college apartment, I'm not lit up by the passages about the common good. You know, I'm like, oh yeah, you gotta wake up early. You gotta shrug this criticism off. And I don't look back on that with embarrassment or cringe. I just think that's probably the most accessible entry point. And that's the most straightforward of it. And so I understand this even now. It's like, look, am I going to make a YouTube video about stoicism and its strong social justice components? I mean, And I am because that's interesting to me. But I understand that when I make one that's like 10 stoic strategies for owning the day, that's going to reach more people and that you can't talk to them about the social justice side of things until they've heard of it first.

14:12And so in my works, I've always kind of understood, and this is, I think, coming from the marketing background, it's like, what is the most compelling, understandable, articulatable part of it? let's start there. And then once you're kind of in that funnel, we can talk about the more complicated ideas. Yeah. So what happens when The Obstacle's the Way comes out? Now, you know, it's sold millions of copies and is in all these different languages and has made its way through professional sports and special forces and tech and politics. But like the first week it came out, it sold, I don't know, 3 ,000 copies.

14:48Like it didn't hit a bestseller list. It didn't fail, but it was definitely a slow build. I remember about a year in was like some of the first serious media coverage, maybe a year and a half in the New England Patriots had won the Super Bowl and some members of the team had read it. So there was some media coverage and like it sold out and it sold out not so much because it was like media coverage everywhere, but because they weren't printing that many copies because it was like a year-old book that had done okay. It sold more copies every year for like 10 years in a row. Do you know what happened with the Patriots?

15:28Did like Tom Brady or Bill Belichick read it and pass it around? Did the crafts like give copies to all the players? Like what happened? I know Mike Lombardi who was in the front office there. He read it. And then he sent me an email and I sent him a bunch more copies and then he passed it around. and then their season kind of turned around and they won the Super Bowl. I think those are unrelated variables. I mean, causation, correlation, who's to say? It definitely was when Sports Illustrated wrote about it. I'm not going to disagree. But he was one of the first people in professional sports.

16:02There's a guy named Andy McKay, who's a performance coach. I think he was then with the Mariners. That was one. There was just a smattering of different people in different fields that kind of picked it up. and then each one caused like a kind of a little contagion in their own space. I mean, the funny thing about Mike Lombardi, so Mike Lombardi passed it around the Patriots. And then I found out about this from a Google alert. He's the one that gave it to the Seahawks after they beat them in the Super Bowl. And now it's a West Coast book. And it's just kind of going around. That just happened.

16:38And that happened for slowly and steadily over many years. And it would be like, ESPN would be profiling someone and be like, on the shelf in their office is this. And it was this kind of like little secret weapon kind of a thing. And then I started giving talks and there was never any moment where it was, I mean, it didn't hit a bestseller list until 2019. So let's talk about scaling the impact of your work. Because again, there are a lot of, use the word broadly, creators who could keep putting out a book every couple of years and build and build and build. And that's sufficient, get paid very well to go do talks.

17:18You've scaled across platforms here. So at what point did you see that there was an opportunity to scale the reach and impact of your work beyond the books? So this is right around the time that I wrote daily stoic so i'd always written online and always had an online audience but i found it to be very hard to build an audience around just me as a person and so when and it's actually my agent who had the idea for the daily stoic the idea of being like a page a day sort of entry point into stoicism i was familiar with the sort of page a day books and i know a couple of them had done Wellick, he had published The Daily Drucker when he was an editor at HarperCollins.

18:00But what I immediately recognized about the idea of a page-a-day book was what happens when you get to the end of the book. And could you just keep that going as an email every day? Kind of been the solution to my problem of like, how do you kind of keep this conversation going? And so The Daily Stoic, which we launched in 2016, was the idea that like Stoicism is this thing that you should be reading and engaging with. So it started as an email list and I'd already had an email list, so we were able to, you know, sort of drive some people. But I think it started at, you know, with maybe 10 ,000 people in 2016.

18:39And now we'll go into 2026 with easily a million people getting it every day. And from the email, you know, it was like, okay, we started hearing from people and they were like, well, I just don't like reading this every day. Can I listen to it? And then so then I started doing the audio and that became the podcast. And then social media, the idea being that like my preferred medium to learn about things is books. That's what I like to do. But that I'm probably in the minority. Just ahead, more with Ryan Holiday on why being smart doesn't always mean being wise.

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21:34Welcome back to Masters of Scale. You can find this conversation and more on our YouTube channel. Tell us about the new book. So 2019, I had this idea for the series on the Stoic virtues. Courage and discipline and justice. And then the fourth and final one is wisdom. I've never done any books that were related to the other books. And it's been interesting because because Zeno, who's the founder of Stoicism, would talk about how the virtues are distinct yet inseparable from each other. And nothing quite illustrates that to you like having to write four distinct books that are hopelessly and exasperatingly interrelated with each other.

22:16So it's been this kind of interesting challenge. It's like you're writing Courage and all you're thinking about is this first book. And then you realize, shit, I locked in a story that I would like to be in the third book in the series, which I hadn't even conceptualized yet. Interesting. So you hadn't mapped out, here are the four books. Here's how I'm going to structure this. Here we're going to pull them apart and tie them together. I did as much as I was able to. Obviously, I knew what the four books would be, and I knew what order they would go in, and I knew vaguely what each of them was.

22:46But it's not until you're writing, at some point you're on the third one and you go, you know what would go perfectly right here, that thing on page 26 of the first book, which is now permanently stuck there. But that's the point is that we know what courage is, right? Courage is when you brave danger. But then what danger? Why? To whose benefit? Well, now you're dealing with justice. And then how much courage? Like, where's the line between courage and recklessness? Well, now you're talking about discipline and temperance. Well, how do you know what the right amount is? Well, now we're talking about wisdom, right?

23:22Or how do you know what is good and bad, right, and wrong? Now we're talking about wisdom. So all the virtues are fascinatingly interwoven with each other. So the wisdom book is the final one. And what I've been saying is, you know, no one's born with wisdom, but all the virtues are born from it. Like it's the one that defines the other virtues. When you launch a book like this into the world, what is success for you? I remember on my first book, it's funny how quickly, like goes from a dream, like, I just want to, I want to work for myself or I want to like write a book. And then you're like, I want it to sell for a billion dollars, right?

24:00Like all you wanted was to not have a job. And now you're comparing yourself to the most successful people of all time. All I wanted to do was write a book. And then it immediately became, but if it doesn't hit a bestseller list, like what was the point? And so I think I was mostly concerned on my first book was how does it sell? Does it hit the list? What are people saying about it? The irony being that those three things are like the opposite of Stoic philosophy, because not a single one of them is in your control. You talk about Elon here. Why Elon in a book about wisdom? Well, Elon is one of the smartest people on the planet, right?