But I'm cleverly going to use this as it's a sort of metaphor for our longer discussion today. Pursuing the New York Times bestseller list is going to be sort of a metaphor for how we think about cultivating a deep life. And so I'm going to want to get into your story more so than I've done before.

But before we do, let me just hit real quick on the new book because I really like the new book. This is the third book in your four book series that's going to be on the cardinal virtues of stoicism. This book is on the virtue of justice, which I think is critical in thinking about the deep life, which is the theme of this show.

But let me just ask you about that before we move into your life. Justice is a hard word to define. You took it out of your title because it's a word with so many definitions. How do we how do we think about justice in the way you're talking about it?

Yeah, I did take it out of the title. Courage is a word that when people hear they like it and they want more of it. When they hear discipline, they think, OK, yeah, I'm on board with that wisdom. Same thing. But when people hear justice, I don't know. There's something there's something that feels judgmental about it.

There's something that feels moralistic about it. There's something that feels, I don't know, political about it. Right. Which it is all these things. So part of the reason I thought it would sort of be off to the slowest start is I felt like it had a sort of a strong tailwind against it, which is why I was interested in writing about it and why I think it's important.

But I wanted to I wanted to I wanted to take justice sort of down a few pegs and make it something much more practical and accessible. The sort of standards by which one lives and holds themselves to as as as much more a way of life than like. These, as you know, in academia, like justice as as a field of study is often about these really esoteric or abstract questions.

And and and the more you study justice, almost like the less actual understanding you get of it, like you start to doubt whether it exists at all and whether it matters at all or whether whether it's possible at all. And that's just strikes me as so opposed to the idea of like, like, are you a person who keeps your word?

Are you a person who's honest? Are you a person who treats other people? Well, are you a principled person? Are you a person who makes the world better for you being in it that that to me being just a much more practical and yet also aspirational idea of justice?

I think people often leave this out of their conception of what they're trying to do with their life. I often use the terminology code in the sense of what's your code, right? And somewhere that should be written down and it's going to change. It's going to evolve, of course, but that without that foundation, it's like not having to keel in the boat.

And so then the winds are going to be blowing you all over the place. Why do you think why do you think this is something that. In today's moment, because I think 100 years ago, like this is the starting point is like, what is your code? You could you could specify those principles like in your sleep.

Why is this something that is a surprise to people or something we have to push people to consider in our current moment? Well, looking at much more homogenous, even top down society, we all agree or are forced to agree with certain definitions. Right. So if we all share the same religion, Christianity at one point has the same cardinal virtues as stoicism.

So if we all believe in the same God or if we all accept or are forced to accept even the same definition of, say, like masculinity or femininity. Right. Then then then the virtues of what a man or a woman is, is very clear. How one should behave is very clear.

The sort of religious tenets are very clear. So so it's easier to go like, hey, this is what is right and wrong without feeling. With that with like what happens when you live in a much more pluralistic society, which I think is a wonderful thing, is that suddenly your definition of right and wrong is not shared by everyone.

So then we have to have this sensitivity and not wanting to say, hey, don't do that. Hey, that's bad. Leave those people alone again, all positive things. But it has partly the effect, I think, of making it harder and harder to give people strong advice or a strong sort of culture that enforces or celebrates a kind of a code.

You know, like the the the relative relativism of society is a generally, I would say, a positive thing because it's more tolerant, which is a virtue of justice. But it makes it hard to just go, hey, that's a bad thing to do. That's the wrong thing to do. So I think what you end up with is a system, a culture that doesn't teach these values early on or or even more confusingly, it holds up some of the old stories of the past that we used to use to sort of reinforce and inspire and it just pokes the holes in them.

Right. So if you if you only look at the founding fathers or you only look at the ancients and you look at all the thing, all the ways that they were hypocrites, all the terrible things they did. And again, it has this effect of sort of just confusing one's definition of justice without giving anyone really a code to replace it with.

Right. So let's say I'm twenty five. Right. All right. I'm coming out hot out of college. I sort of have some professional ambitions. I've been listening to some Huberman. So I've got some physical protocols nailed down, but I don't come from a religious background. I have a generic yearning that I need some sort of code.

I need some sort of stability to live by. Where do they start? Yeah. You know, I think that space is a really interesting one because you're right. There's a whole bunch of sort of thought leaders and information and books and stuff out there that's like, here's how to get stronger.

Here's how to get faster. Here's how to get smarter. And by the way, those are kind of the the the other virtues. Right. This is courage and discipline and wisdom. Yeah. And then if you don't have this other component, this code, this sense of right and wrong, what you do and don't do, how you treat people, what you allow.

Really what you see and you see with some of those people is like the algorithm kind of takes over. Right. What your ambition becomes the thing that guides you. So what's ever best for your career is what you do as opposed to, you know, what you feel like is OK or not.

And I think you and I have probably both experienced this where there's. There are all sorts of decisions that you get faced with that, hey, what's going to grow my YouTube following the most? What's going to sell the most books? What's I'm being offered to speak at some event?

If all I care about is whether the fee is large or not, you know, I'm going to find myself in some places that I'm not going to feel so good about that are probably not going to age well, that I'm going to have some explaining to do later. You know, and I certainly struggled with this in my 20s.

I was just like, hey, what's best for me? What's most interesting? What's most fun? What's most challenging? What I was thinking less about was like, hey, is this something I want to be a part of? Like, is this something that's good for the world? What would the what would it look like if everyone acted this way?

Right. My first book was sort of this expose of of a media system that I kind of woke up one day and realized, hey, if if this is if this is what I am doing to what we would call the information commons, you know, and everyone is behaving this way.

How is anyone going to know what's true and not true? You know, the the system depends on, you know, some sort of self enforcement mechanism. And so I think that's really what we're talking about and what we don't hear enough about. You know, there's lots of people can give you advice again how to get bigger, stronger and faster.

But then it kind of stops very suddenly when it says, you know, hey, doing that sucks. Doing that is bad doing behaving that like there there there are certain things that should be off limits, certain lines that we don't cross, you know, having Alex Jones on your podcast would probably get a lot of listens and views.

Is it something that you should be a part of? Absolutely not for a whole bunch of reasons we could go into. Right. But but that sort of drawing on the line and say, hey, this is I don't do things like that is kind of what we're talking about when we talk about justice.

Well, and one of the aspects of that, which I think is captured well in your book because of the format you use, the format which is based on stories, I think, is effective because it gets at some of the psychological realities of the advice as opposed to just the systemic, systematic structure of the advice.

And one of the psychological like 10 commandments, it's not you. You get a richer. I mean, speaking of 10 commandments, you see the same thing in, you know, the Old Testament of the Bible is through stories. There's a more psychologically complex analysis of an issue. And one of the principles at play that I don't think is emphasized enough that people when it comes to things like justice, especially young people, is that actually the value derived from applying a principle in a way that in the short term is negative in the sense of that you miss out on reward or opportunity.

That value is incredibly feels really good and is incredibly important. Like, in other words, you're you're trading. I mean, I'm thinking about Clayton Christensen, how you measure your life. He kind of gives this famous example. I can't play basketball on Saturday. I guess it was a Mormon thing. And if we're in the playoffs, I can't do it.

Right. Really kind of stunk in the moment. Right. He was good on the team is good for the team. But there is like a larger value that came out of it. Right. Mining that value is important. I don't want to give specifics, but, you know, I turned down a speaking gig not long ago overseas.

A payout that would have been like my annual salary as a professor. Where it was, the country it was, the who was sponsoring it. I just can't do that. Right. I wonder if we were invited to the same thing because I went back and forth, not just myself with a very similar thing, but I heard from several other people that maybe were also invited to the same thing.

I bet we're talking about the same thing. I bet we are. And and and yeah, it's it's I love that expression. You know, it's not a principle unless it costs you money. You know, it's very easy to watch. I don't know, like the live golf league and go, hey, it kind of sucks to blow up your sport to get paid a bunch of money from a foreign government.

That's obviously just trying to sort of win a public relations battle. That's ultimately creating an inferior product for the sport and, you know, isn't sustainable. And then, by the way, a bunch of the people involved are just also gross. Right. Like it's it's very it's very easy to watch that on the outside and go, you know, so and so should have done X or, you know, I can't believe so and so did Y.

And then I think it's much more interesting to think about what decisions you have made in your life that have cost you money or we see this all the time ago. Oh, these politicians in Washington, you know, they're just they'll just do anything to be reelected. They'd never take a vote that would would threaten their job.

And I try to catch myself and sometimes I bring it up to other people, but I always try to catch myself when I feel that rising up in me and I go, OK, but but what decisions do I have in my life that have threatened my career or my livelihood?

And if you don't have any, it either means you're sort of morally perfect and you've never found yourself in a tempting situation or it means you're actually playing it much safer than you should and are, you know, haven't been on the right side of things as often as you think you have.

And so, yeah, those things are there. I would love I would love to believe that at some point they become easy. And I it makes it more impressive to think that it makes it more impressive to think that it was easy for the person. But what you actually find is that they were pretty vexing, difficult decisions and they thought about it up and down, up and down.

And at the last minute, you know, they they made that call and it was tough. But there's a there's an expression about like we keep rituals, but then the rituals keep us, you know, and I think there is something about those principles and those standards. Yeah. Sometimes they keep us from doing things, but they also kind of protect and serve us and provide us a lot of meaning, too.

Yeah. I mean, I love this idea. Seek sacrifice in some sense as eagerly as you're seeking professional success, because it's going to be just as nourishing, not just nourishing, I think resilience creating. It's going to give you a better sense of yourself. You're going to have more ability to apply character in the future.

It's going to define yourself against the sort of near infinite space of possibilities of who you are. But it's not on the list. We have get your body in shape is on the list. Get your bank account in shape is on the list. Get your love life in shape.

Like, these are obvious things on the list. That one's not there. So that's why I'm glad this book is out there. I think this is a deep life guidebook. Well, thank you. Yeah. You know, I was talking to someone the other day and I was kind of joking around.

I said something and I was like, you know, it's not that hard to not be a piece of shit, right? Like that, but, but it, it, it actually apparently is hard, you know, that these decisions that we make, you know, to not screw people over, to pay the people that work for you fairly, to choose to, you know, um, if, if faced between a, uh, uh, an environmentally destructive choice and a non environmentally destructive choice, that the, the, the decision to, I don't know, be faithful to your spouse, to uphold your contractual obligations, to S to speak honestly, to tell people what's true as opposed to what people want to hear.

I, that's probably the most vexing and tempting of the sort of content creation space, which is like, you're always in the short run, you're going to do better telling people what they want to hear. In the long run, you cannot build a career doing so, right? Like you, you, you have to develop a reputation, not just of telling the truth, but like, if, if you're just reflecting back to people, what they want, they're not seeing any of you, they're only seeing themselves.

So you're not actually building much in the way of a connection. So there's this sort of constant struggle and tension between these kind of seemingly obvious short-term decisions, and then this long-term sustainability and reputation and integrity. And yeah, it's, it's, it's like, we just, we just don't even talk about it.

Well, let's shift here to a related gear. Uh, you know, on the show, there's usually two topics we talk about either, um, people who have written something that's relevant for cultivating a deep life or people who have lived the deep life and we can learn from it. Um, you're both in one person, right?

So we were just talking about something you wrote that's relevant to people living the deep life. Your life, I think is also an interesting template, or there's interesting lessons to extract about how one cultivates a deep life over time. So, so with your indulgence, I kind of want to jump back, uh, early to your story and then we're going to move it forward.

I want to jump all the way back. Uh, you dropping out of college, um, bring us inside the, what I want to keep coming back to is the, the vision at that moment about what you were thinking, what you were going for, what you had in mind for what you were trying to do with your life.

So what was the psychology of a young Ryan Holiday, uh, leaving college and those sort of, was that mid two thousands? Yeah. I, I, I, I think I had a vague sense that I wanted to be a writer and I had a much stronger sense that I did not want to work in an office.

Like I just didn't want a regular life. And, um, I was studying writing and political science and I had this chance I, uh, to, to work in Hollywood and I had a chance to be a research assistant for, for a writer named Robert Green. And it just struck me that, Hey, to, to be a writer, what was a better way to learn how to do that?

Was it to go to college, to finish college where some of my professors were published writers, um, not particularly successful ones, but, but published writers, or would it be better to go directly learn from someone who had, had done the thing at a very high level and was doing the thing at a high level?

So I ended up sort of making that leap and, you know, it was, it was sort of scary and terrifying in a lot of ways. Um, but, but I, I just, I just had this sense that someone had given me this piece of advice. They said, writers live interesting lives, which, uh, I I've thought about a lot since.

And I was just thinking like, yeah, like, okay, let's say I just get my, get my normal degree and graduate. Who's going to, who's going to publish my writing? Do you know what I mean? I'll just be like literally every other student who is graduating. I had about a year, a year and a half left in college.

I would just be like everyone else. I would be at the exact same point I was then, except for, I would have foregone this experience to actually study under someone who was doing the thing. And so I just went and did that. And it was, you know, it was, it was a, it was a surreal experience in a bunch of ways.

I learned a bunch of stuff, but, but mostly I was just trying to like, go toward like, go, go as directly as I could towards like real world experience. And then also do some, do the unusual or unexpected thing. Did you see the position with green specifically aiming towards your interest in writing and the Hollywood position as a mix of, I want to do something interesting.

And also what's the thing that is going to be an income source that, how did you see those are two, because Hollywood in that position kind of is the epitome of office politics and being in an office and like arbitrariness or whatever. So I, I mean, I love the complexities when we dig into like the reality of these stories.

So like what role did the Hollywood piece play in that? You're working for an agency, right? Yeah. I worked at a talent management agency. I mean, like when I was growing up as a kid and just had this sense that I didn't want to work in an office, I don't think I was thinking office space, not like a talent agency in Beverly Hills, you know, like it was, it, an office is still an office ultimately.

And you realize that pretty quickly. But, and a job is always a job, but, but it felt different and exciting and unusual and certainly far outside my, my ordinary experiences. But I think it's funny. I remember, I remember two things about it. So, so I'd wanted to work for Robert.

I don't think I would have dropped out of college just to work for Robert. I don't know if I would have had the courage to do that. So then when I got offered to, to be the assistant to this, you know, sort of big movie producer, um, who again, who was also someone who was doing the thing, he wasn't, you know, coming up with the scripts or whatever himself, but he was making stuff.

So, so I, again, it was another doer, but I remember he offered me $30,000. And I remember thinking, wow, what am I going to do with all of that money? You know, like, it just seemed like an insane amount of money to me at the time, uh, because my, you know, my expenses were nothing.

I wasn't married. I didn't have kids. Like my apartment was probably $800 a month. Um, and, and so I just kind of went towards doing this crazy, unusual thing that would kind of introduce me to a world I knew nothing about, but there was this safety net of like, yeah, I had a paycheck.

I think when, when people tell me, Oh, I'm thinking about dropping out of college. I, I always go like to do what, not like, what are you aspiring to do, but what are you dropping out for? Like, I think it's very failing out of college is, or, or quitting your job is very different than, uh, leaving college to go do a different thing.

Like if you have lined something else up and you are, you are jumping from one ship to another, to me, that's very different than what often happens, which is your heart's not in a thing and you're not very good at a thing. And so you fail at it or you, you bounce out of it.

That's, that's a riskier proposition in my view. So then I see you now. Okay. During this stage, you, you're working with Roberts. You're learning about writing. You have the Hollywood job. It's paying the bills. It's interesting in its own right. I imagine a young Ryan holiday basically surveying the horizon.

Okay. I'm looking for, where can I make my move? Uh, marketing became that first move. Um, so not just how did that happen, but how were you thinking about those initial opportunities to fall into marketing when it did occur? You know, it's funny. So when I was at this talent agency, I, I signed this kid, he was like 16 and he was like uploading these YouTube videos.

And it was like the first sort of YouTube person that, that really any of the agencies had signed. It was like pretty new. And it's funny. Um, he, he didn't end up going anywhere. And then just like, he's blown up, like in the last, like six months, like this person, he's like middle-aged now.

He's like 30 years. I think he's like, I mean, he must be like, uh, early thirties. Yeah. It must be like 30. Um, Mr. Beast, Ryan. It was just a young, I wish I wish. Uh, uh, but, but anyways, it was, it was funny to watch like the actual development cycle of something.

Like I thought this guy was like the next big thing. And actually, you know, it was more like 15 years later, he would be a big thing. And I, I think I probably realized pretty early on that. I just didn't have the patience, uh, to operate in that world.

And I didn't like, I didn't like, uh, not actually doing anything, which is ultimately what most sort of reps do is they kind of just sit back and help you with things you're already doing yourself. So, uh, what, what ended up happening is Robert green, who I was working for happened to be on the board of directors at American apparel.

And so I was sort of learning all this stuff and he got me, you know, in the door there. And I, I went and I, I did marketing there and then I worked for a bunch of different authors. And I sort of built this marketing business. What, what I think I was going towards is, is I understood that creating stuff and selling stuff was two very different skills, but the best artists and athletes and entrepreneurs and creatives are able to do both of those things.

And so like, did you know that when you took that marketing job, were you thinking I've seen enough in my agency position to know that this is really important and, uh, me mastering this as I'm going to apply this to myself. Like this is. Yeah. I think, I think I was always going towards applying this to my own stuff, uh, how, how, how, how explicit that was developed over time.

But I think I understood that like, look, anyone can have ideas, but it's only the people who know how to sell the ideas that they have that are able to, to sort of break through. And so I, I spent, yeah, a good chunk of my twenties. Um, really just learning the ins and outs of that.

And, and what happened is that helping people do that gave me a lot of, first off, I built a lot of relationships, but second, I built a lot of experience and got a lot of reps. So like when my first book came out, it was not the first book that I had put out.

I think you, you had a similar version of this and that you put out those, uh, those sort of guide books first. So by the time you were doing your first book, you actually like your first, let's call it real book. It wasn't your first real book. And that is a, a really invaluable thing because you know, if, if you're a director of them, like how many movies is even a great director do in their life?

And it might be three movies. And so if you don't have any experience working on other people's projects, you're going to be learning all your painful lessons on your own projects. Right. And what if, what if what you learn is, oh, if you title the thing wrong, or if you time the thing wrong, it fails.

Like, do you want to learn that on your project or would you rather learn it on somebody else's project? And so I got a lot of experience and, and that experience continued up until relatively recently, like on other projects, I was just learn. I got, I have so many more reps.

I've done a lot of books myself under my own name, but I have more reps on putting out books than like basically any author you could think of. Cause I've just been through it with other people. So many times the, the analogy that comes to mind from the movie world is James Cameron, uh, working in, uh, Roger Corman's sort of shop, uh, special effects, second unit directing took over the special effects shot.

They began to put them on more and more of the directing, uh, by the time he did terminator, he really had a lot of experience with, for example, how to do really good on-screen effects. He had a lot of experience with work with the cameras. So in your own story, getting to your first book, um, I know you went on to work with Tim Ferriss.

I know you went on to work for Tucker Max on the marketing side. These are along with Robert really three of the bigger nonfiction, non memoir, nonfiction sellers of the two thousands was all, all three of that was before your 2012 first book. So there's, or these are all overlapped, but overlapping same time.

Uh, and, and a lot of it before. And then, but yeah, by the time obstacle came out, you know, I'd done a lot of books. What made you, how'd you pull the trigger? So you knew you wanted to write, you're looking for the opportunity, right? Yeah. And by the way, I'm an answer to the question of how could, who would, who would want to publish someone just coming out of college?

What I found out was the only answer to that question. And I actually talked to agents and was like, how could I possibly thread this needle as a 21 year old and get a book deal? And they basically said, the only way you could possibly do this is if you're writing about students for students, right?

So basically you were right in the sense that the only way at that age, like right out of college to get published, the only way to do that in nonfiction was to basically do what I did, which was I can write, uh, how to become a straight A student or how to win at college.

Like that was the way in. So you were probably right there. Um, but these years go by, what was it that made you pull the trigger on trust me, I'm lying. Your first book, what confluence of factors came together that made you say, okay, good, let me roll. I think part of it was disgust.

Part of it was frustration. Part of it was, I felt like I understood this thing. And I, a great, a great thing for a book. It's something that you know a lot about that nobody else knows anything about. Like anytime there's a delta between your sort of personal experience and how the rest of the world perceives something that can be very powerful, like here, let me show you how this really works.

Let me show you what's going on behind, behind the curtain. And I had a chance to do that with that book. I knew that that's not what I wanted to do for all my books. I just knew I had a chance to do it with that book. And so, um, I, I took a risk and, and it was less risky than dropping out of college.

Like I basically took, I went from, you know, being full-time to being part-time at American Apparel. I was like sort of an early remote employee, uh, before that was a thing or location independent or whatever you want to call it. I was ready to leave. And they were like, actually, what if you just like kept working in a, you know, a reduced capacity, we'll pay you a little bit less, but you know, we just want to keep you on.

And I thought, okay, uh, I was ready to go and, and didn't end up having to, but, but it put me in a position where I could go and write the book and just see if there was anything there. Um, which is not how the vast majority of nonfiction is done.

The vast, the vast majority of fiction is sold as a project first. And then, you know, it goes through a bidding process and then, you know, you have a while that I just went and I wrote this book. I wrote the first draft of this book and, and because I'd worked on a bunch of other books, I knew agents, I knew, uh, I knew publicists.

I knew other authors who had vouched for me. So I, I, I had someone I could show it to I'd earned, Hey, this is my first book. Will you check it out? Uh, and so I just went in and did it. And, and also I, I didn't, I had a job still, right?

Like I had a job in flexibility so I could go work on this project. So I just went and I did it. And, and what I'd put together was, I guess, provocative enough and different enough that, uh, a publisher was willing, willing to take a shot on it. It was, it was going to go into, uh, uh, out to auction and, and penguin random house portfolio, which is our publisher just bought, bought it outright before it went to an auction.

And that's where I've been ever since. So it was kind of this surreal, very lucky thing where, uh, I, I, I made a bet early on and it, that's just where I am still. Well, this is a time to resolve something I've always wondered. Uh, so I remember as part of your marketing campaign, or at least my vague memory, correct me, correct me if I'm wrong.

Um, you planted a story maybe with galley cat that there, you know, that you had gotten a $400,000 advance. That's the number I remember. And the idea was this would catch attention. And it did, I guess for the blogging world, they're like, that's so much money. What's going on.

What is this kid? Uh, and it was reported as like, that was you had wildly inflated it or something. Did you, is that right? Did you plant that story and was that inflated or was that not? It's funny. Now we look back, it's like, that's not a crazy advance, but in the world of blogging in like 2012, it was like, no one has ever made that much money in books before.

What is the story of the galley cat leak? So what, so what actually happened was, um, one of the things I talked about in the book, uh, that you sort of realize in marketing is that nobody fact checks press releases. You can basically claim anything you want in a press release and people will pick it up.

And then once it's picked up, then other people will pick up that somebody else has picked it up and it becomes real, right? You don't realize that what you're seeing on social media is, uh, traced back to a press release, which costs $49 to go out over the wire, which isn't even a thing anymore.

The wires usually, you know, previously having been actual telegraph wire. So I was making this point that, that so much of our news comes from these very flimsy or if outright false stories, uh, sources or susceptible sources. So what, what, what had actually happened is I, I gotten like 200 or 250 for the book.

And so, uh, which is a lot of money then, and this is even a lot of money now. Um, but what I decided I would do is I would just, I would, I would announce that it was like 500. I think I announced it was 500 or I may have even just like hinted that it was 500.

There's like these weird for people who don't know, there's these weird terms when you announce a deal in the, in the trades in, in, in very good, good. It's a very good deal. It's a super deal. And, and these, these mean like a band of advances. So I forget exactly what happened, but the point was, uh, I, I put out a press release implying that it was a $500,000 advance, which then got picked up by, uh, what was then sort of an industry blog called the galley cat.

I don't think it exists anymore. So, so they reported that, you know, Hey, this kid you've never heard of who's 24 years old and has never written anything before, just got a $500,000 advance. That was sort of the whoa. And then, so what I, what I did was, uh, then I, I emailed that to a bunch of gossip websites.

Um, and, and I said, uh, did you see that this kid got 500,000, a $500,000 advance if the old, I said something like the only way someone would pay this much money is if it's some kind of celebrity tell all. So this kid must, must be spilling, you know, a bunch of, of, of, of gossip about all these famous people that he's worked for.

And then, so that got picked up in other places that it was this celebrity guy. So just to be clear, uh, so people, the, the purpose of this was to make the meta point that there, is there some self-promotional benefit to doing so? Yes. But I wasn't just doing it because I wanted to be famous.

There wasn't even like social media to benefit from at this point. Uh, I, I was making this point to show that, uh, one, I, I, I actually, I was writing a book about media manipulation. So I wanted to show how media manipulation actually works like with the book itself.

And I was trying to make the point that, um, this is, this is how information that you consume on a daily basis. This is how it happens. Like this is how these rumors get started. And so it, it, it worked in the sense that people picked it up. And then in the book, I described how I had done this with the book that the people were then reading.

So I, I was trying to, I was trying to take it. I was trying to expose certain loopholes in, uh, how the media system worked. So I'm interested in the, the upcoming transition in your career story. I see this as phase one before the stoic phase, right? Um, so you, you have this book come out at this point, you've sort of incorporated your own company.

At this point, brass check was a, an entity or your, uh, marketing company. Um, around this time too, you did, uh, I think it was just a digital original growth hack, growth hacker marketing. So I'm assuming at this point, if we interviewed you, you had a vision, uh, what was that vision for like your next five to 10 years?

Was it at this point, a successful marketing company writing books to help the company? Is it, I'm going to be writing about marketing and I'm going to be a known writer. What is the vision like right in that pre obstacle era? I think I was a little conflicted because I, I, I was very good at marketing and yet I was writing a book that was essentially making me radioactive in certain marketing circles.

So there, I had some elements that wanted to, to get out of it entirely. And yet it had this effect of also, uh, building this sort of company and consultancy that I ended up setting up. And yeah, I was just, I'm just looking at this because I'm, uh, I'm doing the 10 year anniversary of the obstacle is the way right now.

Um, I, I sold the proposal for what was the obstacle is the way like in the early fall of 2012. So just a few months after, um, trust me, I'm lying came out. And, and I think my publisher told me later, uh, Nikki Papadopoulos, who I know has worked with both of us.

Uh, she told me that, you know, later they were sort of just humoring me. Like they were hoping that, you know, I would do this one book and then I would go back to the marketing book. So they were kind of happening around the same time, but, but clearly the, the aim had been to get towards, uh, writing about philosophy.

That's what I really wanted to write about. That's who I wanted to be as an author. So that early, even that early, you knew, uh, it was like, trust me, I'm lying. Gets me in the publishing door. Yes. Right. But even that early as that book was coming out.

So you're working on this proposal before that book came out. Yeah. The vision you were beginning to form is, and maybe this was more influenced by Robert, more influenced by Tim. You were thinking, I want to be not hardcore marketer. I want to be writing about, I want to be in the philosophy space.

Um, yeah. What, what were the contours of that vision at this point? I mean, I know you had experienced with Tim, he had a community, he had, there's these other ancillary things around it. I mean, what he had early, not really social, but you know, he was, uh, he was doing the Ning thing and his blog was really big.

Uh, how, so, so what is the, the shape of that vision then? Um, in 2012, fall of 2012. I really don't know how well shaped it was. I think I looked mostly at Robert Greene, who was anomalous as a guy who wrote about big ideas in essentially at like at the level of an academic, but not supported by the Academy.

Like he was, he's outside the system, but he is as deeply researched and, um, you know, sort of as established and, and, and, um, you know, influential as, as any academic, but without that, that sort of structure around him. So I knew that was like a viable path. So I think I was mostly just thinking about that.

I knew I just, I had this idea for a book about stoicism and I thought it could work. I mean, clearly I didn't think it would work at the level that it ended up doing, or I would have demanded a lot more money than I accepted for that first book.

Like, I think the expectations of both myself and portfolio were, were maybe mine were a little bit higher than theirs, but they were both pretty muted. Um, I mean, the obstacles away sold 3000 copies in its first week and, um, didn't hit a bestseller list for several years. Uh, I, I just thought it was interesting.

I was excited about it. It was a thing I wanted to write about and I kind of just took it, you know, day by day from there. I, I didn't, I didn't plan really any of this out. So the, I think the first time I talked to you, you were conceiving ego, the second book, the second stoic book at that point, you had just moved to Austin.

I think you were, you were in East Austin Austin or something like this at the time. And, um, okay. So at that point, so you had moved to Austin. I mean, at this point you were working on the second book, were you now committed yet to the vision of, I am going to keep writing books in this general space and I'm going to build out a brand about it.

So you knew that's what I'm doing by then. I, I don't know if I thought I was building a brand, but I just knew that I was writing books and, and they were commercially viable enough that I, you know, my wife and I had bought a small house and I also still had my job.

You know, I didn't leave American apparel until the fall of 2015. I think it lasted much longer than I had thought. I, I, I was writing ego is the enemy when American apparel fell apart and I came back and did some consulting during the turnaround and then left. Uh, it was a long story.

I talk about it a little bit in the book, but I, um, I, I just was a writer and a marketer and that was kind of my life. I, I didn't, I, I was just kind of going from project to project and, and, you know, basically what happened is I wrote, you know, I wrote the obstacles away and it came out and it didn't do like amazing, but I'd sold ego is the enemy.

And so I was working on that. And by the time ego is the, or by the time obstacle really started to sell, I was working on ego is the enemy. You know, like I was just going from project to project kind of heads down. It didn't, it, it, it wasn't until it wasn't until 2016 really that there was anything close to what you might call kind of escape velocity as an author.

Um, most of the art, like all the authors that I was advising and, and working for were all selling much better than I was, you know? Um, and it was kind of this, you, it was always this strange thing to be like, oh, you know, so-and-so just sold a book for double what you sold your last book for.

And now they want marketing advice. So I, I was much more just kind of in the trenches doing the thing. And it took a while for the audience to kind of coalesce in the books to find, you know, their, their space in the world. Or to get a little nuts and bolts.

I mean, during this period, um, was the way like you and Samantha were thinking about this is like from a financial perspective, um, this is sort of what we need, right? Like this is our number. Uh, and we want to, we have a, you know, I'm, I'm, I'm doing my marketing company.

We have books. And as long as this adds up to this, this allows us to move on and we're safe. What was that? A lot of people think that way. Is that where you were, or were you thinking more? We got it. We're going to blow this up. No, no, I wasn't thinking that at all.

And I was very lucky. I remember it being like, I remember when I bought, when I bought my first house in Austin, like that I was able to use my W two income and not have to apply for a loan as an author or as an entrepreneur, just how lucky that was because, you know, it's, it's a, it's not a life that banks or, or sort of traditional financing favors.

And so I kind of snuck in under the wire and then like my transition to being self-employed and eat what you kill sort of living on royalties, um, was a slow, steady transition as opposed to some scary leap. And so I think that was, that was, that was lucky in one respect, I'll tell you, this is a first world problem, but where I've had trouble adjusting and it's taken a while is that like you and I both know authors or entrepreneurs, people who in one swoop, you know, they sell a company or a book comes out and it just rockets to the top of the top of the sell sales things, or, you know, they sign a big deal for a pot.

Like when you get, uh, a chunk in one chunk, you're, you are forced to update your self perception and your tax bracket and your, you know, you just go, this is who I am. This is what I have. I would say it was much more of a slow boil for my wife and I.

And so being able to adjust and being able to count on things that was, that was a, a period that, that took, it's like our self-perception lagged behind the objective reality, but because it's so, it can be so fickle and it's hard to, to, to anticipate what's going to happen.

It just took a while. Like there was never both my deals for, uh, it, it wasn't until. So if I got 200 for, uh, trust me, I'm lying. I got less than half that for obstacle. I got roughly half that for ego and I got less than that for, uh, the daily stoic, which I split with, with Steve Hanselman, my agent and coauthor.

So it was not until 2018, I think that I surpassed what I had gotten with my first book deal. So, so I was, uh, and again, look for, uh, I understand for people who are just trying to break through all these numbers sound very, very large. Um, and they, and they were, but, but they were, they were not like financial independence, large.

They were just like getting two years salary in, you know, spread out over two years. You know what I mean? Uh, so, so it was this, it was this, it wasn't, I used the word escape velocity, uh, but, but like it w it wasn't until yet 2017, 2018, maybe that I, that I felt any kind of serious financial security as an author.

So it was like a slow adjustment period because look at the end of the day, I'm writing about an obscure school of ancient philosophy. Like I'm not writing about productivity necessarily, or writing about habits or writing about sales. There are, there are a number of other topics you could tackle that would be more financially lucrative and, um, establish oneself quicker.

So it was, it was an adjustment period is a slow, steady adjustment when you move to the, the 40 acres out in boss drop. Yeah. And I'm, I'm being careful not to use the word ranch because I have a, I have a relative who lives out in West Texas who, who has like a real ranch.

No, he has like 500 acres or a thousand acres. And he gets very upset if I call it a ranch. So I guess in West Texas, if you call it a ranch and you're not running 20,000 head of cattle or more, you're going to get shot. Yeah. If you don't have sections, if you don't have sections.

Yeah. Uh, which is a, you know, a whole chunk of acres. Uh, yeah. But, uh, it's a hobby farm. Hobby farm. Okay. So when you moved there, was this from a deep life perspective, was this like one of the first points where you really began to think, but wait a second, we do have all this autonomy, right?

Even if we're not at the massive escape velocity yet on, uh, book income, we might as well shape other parts of our life as well. Like I, we're not going to enough, like what was the, because to me that always seemed like a romantic move when you made that was like, you, you have a, at least one cow, right?

I mean, am I using the right word? It has big horns. Yes. You have a pond, right? I mean, to me, this is all like kind of romantic, right? So talk about that, the role of that when you're trying to conceive of your life. Yeah. I do think coming out of ego is the enemy and the collapse of American apparel, I, I was like, I don't want any of this.

I want to live a very different life. And what is the point of being a writer or having some kind of career success? If you can't set up the life that you want. I lived in New York when I was right after the publication of, of, uh, trust me, I'm lying.

And, um, while I was writing obstacle and then I moved, uh, maybe right as I was finishing obstacle, I think I moved to Austin, but like, uh, I remember, I remember looking at the, the first mortgage statement when we bought our ranch, we bought about, we ended up with about 50 acres now, but, um, the, the first sort of mortgage statement on our place was what I was renting a studio apartment in New York city for, and just going, Oh, okay.

This is like a transformatively different life choice. Yeah. And it, it, it, I think as a creative runway is really important. So, um, you know, people think, Oh, you got to move to New York. You got to move to Los Angeles. That's where you make it. It, that might be where all the contacts are.

That might be where the in energy of your industry is, but you're going to have a lot less time to develop and a lot less freedom to develop. So when I, when I went to my publisher and said, Hey, I want to write a book about ancient philosophy, you know, because I had a day job, you know, and because I, uh, I, at that point, I think I lived in new Orleans because I didn't live in a major city.

You know, when they said, okay, we'll offer, we'll pay you half what we paid you for your last book. I had the freedom to accept that. You know, I didn't, I didn't have, I, sometimes I read about these, like, you know, aspiring novelists or whatever. And I just, I just wonder how they could possibly, how, if it takes eight years to write the novel and, you know, another year to put it out or, you know, whatever, you know, insert creative thing you're doing, how you could do that in a city where a two bedroom apartment is $4,000 a month.

That's just insane. So you have roommates, you live in a bad part of town, you're just creating an environment that I don't think is going to be conducive to being and doing your best. And then also making the best long-term decisions. Yeah. So then, okay, this is fascinating. So then your final phase I see is the phase where you're spending less time outside of writing, less time on marketing clients and instead build out this platform, right?

So like you're, you're very associated now with a multimedia platform surrounding stoicism. Was there a vision to that or did it unfold and you just found yourself one day because it's a pretty big operation. I mean, I've not seen it, right? I mean, it's a pretty big operation. You've got a good amount of staff.

It's, it's multiple newsletters, video, like podcast, et cetera. Walk us through like how that fit into what you are trying to accomplish. Yeah. So my agent suggested that we do this book called the daily stoic. He, he had published a number of daily books when he was at Harper Collins.

Uh, this is my agent, Steve Hanselman. And, um, I wasn't even for, honestly, it was like not even familiar with that as a type of book. I think I'd maybe seen one in my whole life. And when I started going through, I got really excited. It was just such a cool way to read this idea of doing one page a day.

But I thought like, so what are the, what are people supposed to do? They read the one page and then they just close the book and start, start over. Like when they get all the way through. And it just struck me that you could build by the time someone got to the end, you had just spent a year together and that, that, that was right for a continuation.

And so I agreed to write the book, but, but decided I would, I would build this thing on the back of it, this sort of page that this email a day. And I remember I paid $6,000 for daily stoic.com and we started this newsletter and yeah, I've been doing that literally every day for the last eight years.

Um, and it's spun off this whole thing. There's a bookstore and a podcast and in multiple newsletters and social media and YouTube and all that stuff. Um, I, I would say I planned it in the, in two ways. One in the sense that I thought, Hey, this is the first book you're doing for which there is a continuation.

Like what's a community that comes on the back of it. And then I, I, I, I, I, at that point my, my marketing company had, had done quite well and I'd advised a bunch of different companies and individuals and public figures and authors. And, and one of the things that I really hated about it was that you would spend all this time coming up with these ideas and then people just wouldn't do them.

Like one of the exhausting things about consulting is that you realize at the end of the day, people are paying you to give them advice that they have no intention of actually using. It's like this cathartic experience for them. Yeah. But the, if they use 1% of what you come up with, that's like a success.

And that just drove me nuts. It just felt like a bad use of one's creative energies. And so I just, I just, I was like, what if I just spent my energy making my own stuff and I just put the marketing energy towards that. So eventually, yeah, basically what happened is those two paths we were talking about that, you know, sort of finally and fully converged, you know, sometime in the last four or five years.

So when you, you know, it's really grown, right? So it grew from the email newsletter to a big YouTube investment, Instagram, um, multiple newsletters, the podcast, uh, et cetera. Right. What was the thinking behind growing it that way? It's just realizing that most people don't read books. Yeah. And, um, if you have ideas and things that you care about book to, to leave your ideas siloed in books is, um, is, is sort of stopping short.

So, so just the decision to say, Hey, I've, I've already done the hard work of coming up with the ideas, translating this stuff into working in other mediums, uh, is not that hard. And, and weirdly, the economics of the other things might be much better. So, you know, you, you can make, uh, you know, a podcast might have a fraction of the audience, uh, but, but be more lucrative than a book.

And, and so what I, what I, I guess what I was thinking is I love writing books. That's what I care about. Um, that's what I want to focus the majority of my energy on, but how can I get good at explore and build out these other things as a way of supporting that thing?

Right. And as it happens, a lot of the mechanisms by which people discover stuff these days, especially books is in mediums, very different than books. So like people who listen to podcasts are the kind of people who download audio books, you know? And so the decision to have a podcast might seem like it's different than books, but it's actually how you are building your book audience.

Right. And the decision to say, oh, I only write books is actually a decision to say, I want to have a very small audience for my books. What number do you care more about? Uh, total eyeballs, let's say per day, senior stuff or, uh, first six month book sale number on your books.

You know, what's weird. I don't know either of those numbers. Like I, I, uh, I know what right thing right now did in its first week because my publisher sent me those numbers and now we're three months out. I couldn't tell you even within 30 or 40% what that number is.

And I don't know if I know what our, I definitely don't know what our daily or total audience is for daily stoic. I just know that I make this stuff and that the reach is pretty big. I, I, I try, I try not to think too much about those.

Like you're talking about sort of a deep life to me, it's a really shallow life. If you're waking up every day and stressing whether the number is here or here or here, you know what I mean? Like the, the, the, I'm not saying I live in a bubble, uh, cause that's a, that's not good either.

Um, but, but I try to insulate myself from statistics and metrics to a degree that it allows me to just focus on making what I think is good. Do you privilege books in your thinking at all? Or do you really have a unified thinking of ideas to people? There's different.

I mean, to me, ultimately books are the most important and powerful medium to interact with someone. So like, you know, you could have, uh, uh, an Instagram reel that does 10 million views and that would probably have a fraction of the impact that selling a thousand, that a thousand people reading a book would have.

So, so ultimately I, yeah, ultimately all I care about is, is writing books that I'm proud of and that, that those books are finding, you know, their audience. Um, and yeah, what I'm not, I'm not saying, I'm not chasing social media engagement at the expense of, you know, book sales.

That's for sure. I mean, what, what I think is innovative about your model and I've seen this up close. Um, and I don't think people, most people are there yet. Uh, is this, uh, tell me if I have this wrong, but the way you think about things is, um, you are a producer of ideas that are valuable, right?

You've, you've developed the skill and this is what you've done. There's so many hours in the day that you can productively do that. And sort of the, the insight you had is, okay, um, how do we take those ideas and get them to as many people as possible? Well, there's lots of different channels.

And I think the channel overlap piece is one of the more, um, innovative that, you know, if I'm there doing your podcast, you'll tell your team, Hey, clip minute, this minute, that minute, that, uh, turn those into, get that into a content for this daily email newsletter. Your podcast is using what's going out in the email newsletter, except for when you do the interviews, which goes back and feeds into the newsletter, your books get sort of it's ideas.

You've talked about those ideas go back. Um, and it reminds me almost of like the innovations and licensing deals that, you know, people figured out in the seventies or eighties, like we have this IP that's valuable. Uh, well, it could be on lunch boxes and, uh, on stickers and in toys.

I don't think most creatives are there yet. I think they think about channels as independent endeavors, you know, yes, I write licensing stuff to yourself. So, so it's like, I write a book that has a bunch of ideas in it. And then, uh, instead of waiting for somebody on YouTube to read that book and rip it off into a bunch of different videos, I make videos about all those ideas in the books instead of waiting for someone to take one idea from, you know, uh, something I said and turn that into a, an Instagram reel.

I want to make that. And then, yeah, I think a lot about how do I get efficiency. So like I had a talk in Brazil on Friday now as a big, you know, it's like a disruptive thing, right? Like I had to get on a plane. I had to take two red eyes.

I flew to another country. I gave a large talk, but you know, that talk was filmed and then I had to do a Q and a after and that Q and a was recorded. And so, you know, that talk will become 15 clips that, um, that Q and a will become a Q and a podcast episode.

So I, I try to think about, I try to think about how do I use this stuff in all the different mediums. And I, I, um, I think Gary Vaynerchuk is kind of the guy that's pioneered a lot of this, the idea of like, Hey, each one of these platforms has its own kind of unique audience and its own kind of unique language.

And your job is to figure out how to participate. You don't have to, but do you want to see that audience to someone else? Do you want to, you know, miss out on that chance? Now I, I also happen to subscribe to a lot of the things you talk about, which is like, how do you personally set up your life?

So like, I don't spend a lot of time on social media. I see social media primarily as a push medium. And I, the reason I have a team, could I do a lot of it myself? Probably would it be more profitable? You know, if I was more involved, probably, but it would also quality of life, there'd be a quality of life reduction.

Cause I think a lot of these mediums are not super healthy for the individual, but it would also just take me away from the things that only really I can do, which is write the books that I write. Yeah. Um, I love this way of thinking. Yeah. I mean, I've been thinking about it.

There's also this theory out there that you need a certain level of ubiquity before you can get big growth. Right. Um, it's when people kind of know who you are, that then when you have the right idea, that's right timed, you get explosions. If they don't know where you are, it's hard for, it's that like, well, yeah, I know Ryan Hall and I have seen some of his stuff that then allows, would you do something that time's right for that growth to happen?

This is what I think about like your pandemic years. Right. I mean, I see 2016 through 2019, this, you kind of start launching a strategy daily stoic, you build up these audiences into the hundreds of thousands, kind of somewhat painstakingly. Right. Yeah. And then there's like a three year period and everything jumps to millions.

Right. Um, you can't go from 50,000 to millions, but like you can go from 600. And in other words, like you were out there, right? Like once there's a bit of a ubiquity for your ideas, you've defined yourself in the mind of a lot of people. Now it's much more easy when they see a Ryan holiday book.

Like I know exactly who that is. And now the fact that the topic is what I'm interested in, I'm super excited to buy. Right. Like if Steven Spielberg does a movie on a topic I'm interested in, like I'm a hundred percent going to go see that where that same topic, if I don't know.

So, I mean, there's an interesting curve. And I think there's a lesson there as well is that, you know, your, your, your audience grew and then it exploded. Um, but you can't skip the, the growth, unless you're pure algorithmic, like sure on YouTube, you could do this. Like if you're in a purely algorithmic medium, it's possible, but that's a really, um, low touch audience anyways, but like your email newsletters, et cetera.

There are definitely things that just take off like a rocket ship. I think you see this in music, right. There's the kind of musician that, that writes a handful of huge singles that just sort of break out. This is like lightning in a bottle. This is a magical thing.

And maybe you're that artist and maybe you're not. I happen to be more a fan. Like I'm a, I'm a heavy metal fan. I'm wearing an Iron Maiden shirt. Iron Maiden is a band that's basically never been on the radio, but 50 years in 40 plus years in they're like bigger than they've ever been.

It was this sort of very slow and steady multi-generational thing. And they kind of just do like Iron Maiden makes Iron Maiden music. Like I heard their manager once said, um, uh, someone said, you know, you're one of my heroes in the music business. And he said, I'm not in the music business.

He said, I'm in the iron fucking Maiden business. And this idea of like Iron Maiden makes Iron Maiden music and they make it for Iron Maiden fans. And you kind of know what you're going to get, but they've done it so long that you start to get into that idea of like compounding returns.

So it's not exactly exponential, but it is like linear in a, in a very powerful way. Right. And, and, um, you just kind of do what you do and you do it for your people. And there are going to be moments that sort of punctuate it. Like, yeah, the pandemic was a big growth thing, but it's not like, it's not like we quadrupled in size overnight.

It was like, oh, you know, the list grew by 25% this year instead of 10%. Right. But we've kind of just daily Stoic has just been this very steady, consistent thing that gets bigger and bigger. I like, look, you and I both know people who have put up videos that have done tens, hundreds of millions of views.

Probably the most that any of my things have ever done is a couple million views, which is a lot. If your stuff is currently doing nothing, but if you're Mr. Beast, that's disaster comparatively, nothing. So I, I kind of just make a lot of stuff. I make it in a lot of different mediums and I, I, I do what I am excited and interested in about.

And it's built this kind of, you know, this, this, uh, this idea of a flywheel and it, yeah, it can become quite large, but where, again, where your stuff has been helpful for me is like, could it be bigger? I probably, um, will it be bigger in the future?

I would say yes, but I, I would like it to be bigger sustainably and not at the expense of my deep kind of thinking and the, the pleasure of doing, doing the thing. Like if, if, if you told me daily Stoic could, could quadruple in size, but I wouldn't be able to write any more books or write them at the level.

And, and with the time that I currently do it, I would not take that trade. Well, I love that model. I know we're out of time here. We both have, uh, we have school pickup. We have school pickups. Speaking of the deep life, we're, we're, we're honestly, we're mainly chauffeurs.

Let's be honest about this. Yeah. But I, to me, I was saying that like a rich life is being able to pick your kids up from school. There's a version of that. That's that's not rich, I guess, but there's a version of like having the ability to do it and wanting to do it is a wonderful thing.

Yeah. Well, Ryan, thank you. I, I mean, I'm going to, I'm going to do a big summary of this for the listeners. I think there's some, some great thoughts in here. I think there's lessons from your story. I think there's lessons from your new book, which everyone should check out the full series.

I think it really helps build that code. Um, and I love your specific, just because it matters to me because we're in the same world. I love your specific story about how you think about growing audience, doing something Iron Maiden style as opposed, I don't know what the alternative would be Carly Jepsen style.

I'm trying to think of like recent wonders. Anyways, Ryan, always a pleasure, uh, and we'll talk soon. All right. Have a good drive.