Ryan Holiday on The Economics of Book Writing, Why You’re Monetizing Your Media Business All Wrong, His Split with Tucker Max, and More

What, uh, what do you do with your money? Uh, I know you got a ranch.

Yeah.

Uh, I think you live there.

He, he, he's had that forever.

That, I mean, that was like my house. That, that, so it's, it's not like, it wasn't like a hot, uh, like a luxury property or whatever.

It's not like Kanye having a ranch in Wyoming. You actually live there cuz you wanted to live there. Sam, Sam I think has some, some similar aspirations. Um, but what do you do? Are you like, I'm an investor. You just do something boring with your money. What do, what do you do with your money?

Yeah. Uh, well, I, I spent a lot of it on this bookstore. Uh, I, I, I bought two buildings in this small town of Bastrop. Originally, it was going to be a bookstore and a coffee shop. Now it's a bookstore, and I rent out half of it to a record store. But I needed a space to do all my stuff. So up top is my office. My wife also wanted me to take all my books out of our house. So that was part of it. It was like getting all the shit out. But no, I don't really do anything. I don't really do anything with it. I invest it. I like investing in things that are very different than internet things. So most of it's like in income-producing real estate.

How do you describe yourself?

You know, I don't do it very well. You nailed— I would sort of, if I had to say, what do I identify as? I would say I identify as a writer. And then I, I sort of have these other things that I do in that are somewhat related and somewhat unrelated. But like if I had to sort of only pick one thing or like what, what do I feel like I was like meant to do? It's, it's writing. So I identify first as that.

Sean, do you remember this? Did I ever show you this coin I used to carry around? I, I would have it with me a lot, particularly in the old San Francisco office. I had a coin.

Very, remember Two-Face of you? No, I've never, never seen your coin. What are you doing?

There's Two-Face of me. No, it was, it said, what did it say?

Momentus.

Momento Mori. What did it say, Ryan? Yeah, which means like you're going to die. You only live once, right?

By the way, don't you love that? Sam carried it around for years. Doesn't know what it says on it. Momentus.

I knew that it meant like you have to live today. Like you're going to die. Yes. Right. And I was thinking about it. I bought one for $26.. And I was thinking about, I was like, this is the greatest business of all time. I just bought a, like a fake coin from Ryan for $26. It cost him, it was just probably a post, like a stamp just to mail it to me. So only 50 cents. There's not gonna be any returns. There's no, it's one size fits all. And it made me happy and I carried it around and I, I was like, this is the, is that the greatest business of all time selling coins?

And regardless of how good the book is or not, it's exactly something of this shape. I pay either $9, $13, or $26. Yeah, right.

That was cool. I'm gonna, I'm gonna ask you about the mint in a second because I have another mint that I think you're gonna get a kick out of. But do, uh, can you reveal how many of those coins you sell a year, or do you not talk about it?

Well, how much does a coin cost you?

A dollar? More than that. Because more than that. And then there's also packaging and shipping, all that, all that kind of stuff. But, but yeah, it's all to say it's a good, it's a good margin. But, but yeah, it's a good mark. Not as good as a digital product, but good enough.

That business, I feel like, um, you know, I have this phrase, you, you know, you, you are what you admire, which is like, if you admire things enough, you, you end up moving in that direction. And that's a type of business that I really like. The thing, the, the little thing you just said gets like the highest amount of respect for me. Like, okay, Elon can send a rocket to Mars, you know, Steve Jobs can fucking, you know, wear his turtleneck and do his thing.. But an entrepreneur who says, well, I wanted to create, I really was interested in stoicism, so I created this free thing to give it away. And I didn't know what the business would be. The traditional model doesn't really work. Ads, um, it would like, you know, how kind of shitty would a stoicism newsletter be if it was just plastered with ads? Uh, but I did it anyways, betting on myself that I'll figure it out. And then I figured it out first by having my little framework of like, what's a thing that represents this belief? That has high margins, that has low headache, that like, I have a DTC business with over like 3,000 SKUs. So when you're saying that, my body's just like, you know, inside just shriveling up and dying. Um, and I'm like, oh wow, how amazing would it be if I had one SKU that was just high margin and like I could just make that SKU amazing. Um, so hearing you pull that off and, uh, you know, the way it kind of like Sam has it and people at the conference buy it, to me that's like, you know, top level respect because The creativity that that requires and the thoughtfulness that that requires is, is kind of amazing. I think most people would just kind of declare creative bankruptcy and say, I don't know, I don't know how to figure it out, and just never, never.

Sean, have you heard of— this story is going to come full circle, but not till the end. Have you heard of Stuart Resnick. Stuart Resnick? No. All right. I bet you've heard.

Oh, I think I know this guy. They own the Pistachio Company, right?

Yes. So when you go to the store and juice or whatever.

Yeah.

So they own this. It's a privately owned company. It's probably one of the— Linda and Stuart Resnick is probably one of the largest privately owned companies in America. They do multibillions in revenue. His— he started like a security business that he sold and he got some money. And then now he owns Palm, like the drink, Palm drink. He owns Pistachios and a bunch of stuff. Anyway, he— one of his first businesses after he sold his security company, made a little bit of money, he bought this thing called the Franklin Mint. And the Franklin Mint— I knew, I knew, Ryan, I knew you're gonna know what this was. And the Franklin Mint basically started out by selling coins. Eventually they expanded to a bunch of other collectibles, but they started selling coins. And up until somewhat recently, they are one of the largest, I think, advertisers of digital and, uh, not digital, um, print media. And so like if you would open up a magazine like a USA, like a, like a TV and news guide, like the things, they were always selling coins and it was Franklin Mint. And he, uh, sold it for like $200 or $300 million when he was done with it. And you know who bought it recently was Tai Lopez.

Oh wow. Didn't he buy RadioShack also?

And a bunch of shit. He's bought so much stuff.

Hold on.

I'm kind of stupid.

What?

These mint. Okay. Is the mint literally a coin factory? So they take metal and they shape it into a coin of your choosing and then they, they sell it, uh, or they, they, you know, they provide it to, to you who sells it. Is that the idea? Is a coin factory? Is that what a mint is?

Yeah. Although the Franklin Mint is like commemorative quarters and dollars and stuff.

Right.

But they don't, but they do like, they do like a print. No, but yes they do, but they got actually sued because they use like a Princess Diana coin. Or they've done like a, like a, I don't know, like some like famous-ish person that like middle American moms like care about. You can buy like a coin with their face on.

Oh, interesting.

I've met this guy who has a very interesting path that like intertwines with the Silk Road and other things. And, uh, he had said something like, he's like, yeah, what I'm doing now is I'm buying these email lists of like hundreds of millions of people, like the, you know, like the leaked Madison Reed or whatever, what it was, not Madison Reed, what's the, Ashley Madison?

Yeah, yeah, yeah.

Like leaked email lists for like, oh, LinkedIn got hacked. Cool, I'll take all those emails. And like, you can't, like, you can't really even send to that big of a list. It's like too dirty and you'll get like banned or whatever. But he like had some like expertise at how to send mass emails. And he, I was like, what are you gonna do with this? Like, you start a new thing? And he's like, oh no, I'm just gonna find people who like Trump and I'm gonna sell 'em coins.

Maybe hats.

I'm gonna sell coins and hats to Trump fans. And I was like, I was like, wow. And he's like, yeah, like if 0.2% of my list, 0.02% of my list or whatever ever converts, like, you know, I'll just make millions of dollars passively sending these emails. I was like, wow, this is one of the craziest business plans I've ever heard.

There's an argument that Fox News basically exists for the sake of like reverse mortgages, gold coins, and other forms of grift. Like, if you watch Fox News, just the commercials, you get a sense of like just how dumb the audience is, to be perfectly honest. And then you realize why the content— it's almost as if like I heard this great thing about spam. They were saying like, like, you know, you get an email from like a Nigerian scammer and you're like, oh, this is obviously spam. That's because it's not for you, right? It's for someone who's dumb enough to not be bothered by how all the red flags that are there.

And so even further, it's they want people who, after they get scammed, won't really know how to, like, have any recourse. Yes. So they won't be able to get back at you. And so they filter out all the people who have, like, lawyers.

Yeah. And so when you watch Fox News and you get the sense, oh, this exists to create the kind of customer that would fall for these, like, obscenely high-margin, almost criminal enterprises— I know this is an exaggeration, but, but like, right on this side of what's legal or not businesses. That tend to exploit not very smart or savvy people. That's why the content is what it is, is to set up the commercial break where people won't buy real things. When you turn on pretty much any other form of entertainment, you're not seeing those advertisers because you're— that's not who it's appealing.

It reminds me of in India, uh, I don't want to do a deep dive on this at some point, but there's like— India has this culture of gurus, right? So like First, in terms of gods, we have like whatever, 50 gods. So, and then the gods all have like their gurus and the kind of like the saints type of people who give, you know, genuinely good advice. But then they also kind of like do magic tricks and you're like to show that they're like, you know, you know, the man of God, it's like he can produce something in his hand, but it's like literally an illusion, like a magic trick. But the way they work is they have this like virtue, virtuous brand. Of being this person who only wears their white robe and they like don't have any material possessions, whatever. But when you go to visit them and people— I mean, there's like miles-long lines, like going, like crawling up mountains. Literally, they crawl to show their devotion to get to this person's like thing. And then you donate your gold chains, you donate like gold. And so these guys inevitably get raided by the government because they pay no taxes and they like, you know, are involved in crimes. And they go, they find like tons of gold, literally like the physical, the measurement tons of gold in their house. And they have like, and then they'll like license these like chip brands and like popcorn brands and stuff like that. And it's like the face of this guru, but he's selling like, you know, potato chips.

Dude, Bikram yoga, Bikram yoga had ketchup, I think.

Yeah.

It's crazy. Wow. Yeah, no, it's, uh, it's, it's, uh, it's very strange. Uh, once you get into sort of the backend of how some of this stuff works.

Do you know anyone, Ryan, who's outselling you in terms of coins?

It's selling more coins? No. I mean, I do sometimes wonder, like, when, when, when we order, like, we'll order, like, you know, a bunch of the coins from the, from the Mint, which is in Minneapolis, and they'll be like, oh no, we're really backed up. Like, sorry, your order will be like in a couple of weeks or whatever. And I'm always like, who is in it? Who is ahead of me? But, but there, there is. I mean, so, so I was thinking about it. Like I was thinking like, okay, I wanted a reminder of memento mori. And then I thought coin and it didn't occur to me because I had a bunch of them already. So I was probably— but there is a genre of— there's a thing called a challenge coin that like the military gives out or police officers give out or firefighters give out. Sometimes it's like a commemoration, like you visited this place, but like if you did like, you know, this tour of duty in Operation Enduring Freedom or whatever, like they'll, they'll often give you challenge coins. So I think a lot of them are like government clients or, um, uh, like, you know, nonprofits or organizations. There's like that, but like I could get them done. Like we were talking about margins, they would be much cheaper for me to make them in, in large bulks, like from China. Um, but, but we haven't done that. We've always used this, this original place. Um, I wanted to do made in USA,. But then, and then as it happened during the pandemic, it was great because it was like we never ran out of stock of any of our products cuz everything we sell is, is made in the US.

That's awesome. Now, Brian, I wanted to ask you, because you've done a bunch of different things. Okay. So you're a, uh, you're a college dropout. Yeah.

Correct.

You, um, you worked for Tucker Max or you consulted with Tucker Max, uh, Robert Greene, who's the kind of 48 Laws of Power or whatever. Um, you've written a bunch of books, you've, you own an independent bookshop, you got your coin business, you sell courses on that, you've done a bunch of different things. Okay. So I wanted to play a little game just to get to know you game. And, um, and it's called first, worst, best, best, last, weirdest. Okay. And basically it's around jobs. Okay. So what was the first job? And it doesn't have to be like a job, it could be like a side hustle you had. So what's the first kind of dollar you earned?

I worked at a, doing something. I worked at a deli, uh, at a grocery store called Obexers in, uh, in Homewood, California, right on Lake Tahoe.

Tahoe. And what were you doing at the deli?

Like making sandwiches. And I worked in the stock, like, just like a, like a, just a kid. I was 15, 15, 16. Yeah. 15. Yeah. You know, just like $6 an hour, whatever minimum wage was, uh, in California then. Just a, you know, kid who worked at a little, little small town grocery.

And what, what was it like? 'Cause you, okay, you make $6 an hour. I don't know how many hours you're working, but you end up with like, you know, couple hundred bucks after, you know, a couple weeks. That's a lot of money to a kid. Do you remember like what you did with the money or how you felt about that, that amount of money at that time?

You know what, I don't remember what I— I was super into snowboarding, so I probably bought a snowboard or something. Um, but, uh, yeah, it occurred to me the other day, I was just thinking about this, that I basically worked non-stop since I was 15 years old. Like, uh, then I worked at— I worked at Wendy's after that, if I remember correctly. That was a lifeguard. So I've had like a bazillion jobs, but that was That was the first one.

And then like, I feel like at age like 18 or 19 or something stupid, you were like the boss of American Apparel or something like, just like something ridiculous. Or like at 18 you like worked for Robert Greene writing 48 Laws of Power.

Well, 48 Laws of Power came out when I was, uh, like 11 years old. But, um, so not, not exactly. But, uh, I did, I started working for Robert when I was 20 and then I was, uh, the director of marketing at American Apparel, like in my, in my early 20s.

So, so you, when you dropped out, you dropped out because what, you just hated school or you had something you wanted?

No, I liked school, but I wanted to be a writer. And so I had this, I was going to UC Riverside. So, uh, I was, I was working for Tucker who was at that point one of the first bloggers to, to have a book deal. Um, so I was like, I was working for him doing like marketing and online stuff. And then he got me a job at a talent agency, um, where I did like Yeesh, I could not see you fitting in there. Yeah, I was like answering phones and stuff, but I worked on like new media. Uh, like, so this is right, like YouTube had just sold. Um, so everyone's sort of interested in internet talent. So that's what I was working on. And then, um, the summer I was at the end of that summer that I was working there, I was supposed to go back to college. And within one week, uh, I got an offer to, to stay on at the talent agency to, to, I was working for this movie producer there to be his assistant. Uh, and then, uh, I'd met Robert Greene and Robert Greene needed a research assistant on a book he was writing called The 50th Law. And so, uh, and why did all these people like you?

Why did Tucker hire you when you're 18? What did you, what did you do to get hired by him? Because at that time he's writing basically like funny dating stories and sex stories, right? Like that was like his blog at the time, if I remember correctly.

I think I was very young, very ambitious, very hardworking, and I was just obsessed with the internet, like what, what this sort of internet culture would become. Um, and I loved books. Like, I just, I've always loved books. And so I think they sensed that I wanted to be a writer and they sort of, I sort of went under their wing as like an apprentice in, uh, you know, how to do, how to do what they did.

Did you just cold email them?

So when I met Tucker, because I was writing for the college newspaper and I wrote an article about him. Which is what I was doing. I would write articles about people in the way that now you'd be like, oh, I want to meet this person. Will you come on my podcast? Right. But, but this is before podcasts. So I would just interview people and write articles about them. So that's how I met Tucker. I was a huge Robert Greene fan. So I met Robert through, through Tucker. And then the talent agency, the guy who I worked for was producing a movie about Tucker's book. Book. So they were all sort of connected. And then it was through Robert Greene that I met Dov Charney, who was the director of, or was the founder of American Apparel. So it all kind of was all swirling about each other.

And what was the first kind of like personal hustle you did, right? You're helping Tucker achieve his goals. You're helping Robert Greene achieve his goals. You're helping the talent agency find talent. When did Ryan go into business for Ryan?

That's a good question. Um, I don't know what like the first thing thing I would have— I mean, I started my marketing company in 2011 when I was writing my first book, but I think the first big bet I made on myself was, um, I mean, I'd done other like little stuff, uh, before, but the first bit I— in 2011, I basically quit at American Apparel to go write what was my first book, Trust Me, I'm Lying.

So that was like The first big bet on myself, and that was a hit. I mean, that was, that was pretty— it seemed like it took off, right?

What was your advance?

That's funny. Did you, um So you got a big advance. You didn't have that big of a following at that time. How did you finagle any advance, let alone like a quarter million dollar advance for your first book?

Oh yeah.

That was like unlike all the other books at that time that I don't think really there's been that many books like it or that I would, maybe Chaos Monkeys would be another like similar book that I'd sort of, which I thought was good. But so I sold it that way. So I wrote it so that I had it, but it was mostly just all the authors that I knew I sort of got in 'cause I'd worked for Tucker, I'd worked for Robert, I'd worked for Tim Ferriss at that point, so I had a pretty good sort of Rolodex of people who got me in the door when I, when I sold that book.

Are you still doing the deals now, those type of deals now with all your latest books, or are you self-publishing?

I'm still at the same publisher, actually. I've done all my books with the same publisher. Um, uh, I've self-published, uh, a children's book, and then I've self-published 2 high-end editions of traditionally published books that I have. Like, I have a leather edition of, uh, The Daily Stoic and The Obstacle Is the Way. Um, but other than that, everything's been traditionally published. I guess I own the audio rights to one.

Why is that? Because like, from the outside, you know, I think a lot of entrepreneurs feel this way. It's like, oh, publishing, you know, record labels and book publishers, it's all just middlemen and they're— they take advantage and the authors see so little, you know, blah, blah, blah.. And someone like you, you have a, a lot of business sense. B, you now have a track record. C, you have an independent audience you could sell to. Um, so there must be some reason that you say, no, actually people don't get it, that you do wanna publish it for these reasons.

I look at it on a, a case-by-case basis. You're just, you're really doing the math. Um, will, uh, will the, what they're paying for it plus the royalty What, what are you thinking you will earn, you know, in a short amount of time or, you know, in a certain amount of time? So I just do the math on each project. So every time I think about a book, just because I have a publisher, if obviously no one was interested in publishing it, it would be a different story. But I, you know, I conceive of what the book is and then I take it out. My publisher has a first look deal at my books. I, and I see what, you know, what they, what they think, what they're willing to pay. And then, you know, I have an agent and so we obviously try to get that number up as high as possible. Um, and then once I have that number, then I think, okay, what would this look like if I did it myself? So what would it cost me to do it myself? What am I likely to sell myself? Um, how much work is that gonna be? How much of a distraction is that gonna be? Um, and 90% of the time, you know, the math, the math tends to go towards traditional publishing in my experience. Um, the, the kids' book that I did, the publisher just wasn't, uh, wasn't it like, wasn't in their wheelhouse. They didn't totally get the project. Um, but, uh, so I did it myself and it's been great and really fun and artistically fulfilling. But also just an incredible amount of work. I mean, like, the coins I sell directly from my store, right? The manufacturer makes them, they drop it off at the warehouse, they get shipped. Um, fulfilling books through Amazon is like— in like— and then also the 1,000 independent retailers in the United States, plus every international edition, you know, um, is extraordinarily, uh, logistically difficult.

Um, and I remember you, you gave this talk one time that was awesome where you showed a chart of the sales of your book versus the normal book. So a normal book, you get a peak and then it pretty much just kind of goes away. But then for some of the classics, you get a peak and then it goes down a little bit, but then it kind of quickly comes up to the point that we're even, like it's pretty steady throughout. Like A Catcher in the Rye or something like that, or even sometimes it'll suck early on and just slowly get better. Your books, if I remember correctly, they popped just like everyone else. They went down a little bit just like everyone else, but then they like raised and were pretty steady with daily sales. And you're like, that's because I make shit that can last a long time. And this was actually for when you were writing Perennial Seller. I think you were like proving this point. Is that still the case? And considering all of your other businesses, Is book— is making books still where you make the majority of your income, or are you just using that because you love it and it happens to make money, and you— but you make the bulk of your money from other shit?

Dude, that's crazy that you're like the man and yet still it's like the other—

It's like, it's like Michael Bublé or Mariah Carey writing a Christmas song. You know, you want that Christmas hit, you want that new—

Yeah, yeah. I mean, so, so like my book, The Daily Stoic, when my agent was like, we should do a page, you should do a page a day about stoicism. And I was like, I don't know. And he was like, it will be your bestselling book. And I was like, there's no way. That doesn't make any sense. He's like, yes, it will.

Every New Year's.

He's like, it will. And he's right. It, the book sold, uh, more copies this already this January than last January.

Amazing. What, uh, what do you do with your money? Uh, I know you got a ranch.

Yeah.

Uh, I think you live there.

He, he, he's had that forever.

That, I mean, that was like my house. That, that, so it's, it's not like, it wasn't like a hot, uh, like a luxury property or whatever.

It's not like Kanye having a ranch in Wyoming. You actually live there because you wanted to live there. Sam, Sam, I think has some similar aspirations. But what do you do? Are you like, I'm an investor, you just do something boring with your money? What do you do with it?

Yeah. Well, I spent a lot of it on this bookstore. I bought two buildings in this, in this small town of Bastrop. Originally, it was gonna be a bookstore and a coffee shop. Now it's a bookstore, and I rent out half of it to a record store. But I wanted— I needed like a space to do all my stuff. So up top is like my office, My wife also wanted me to take all my books out of our house, so that was part of it. It was like getting all the shit out. But no, I don't really do anything. I don't really do anything with it. I invest it. I like investing in things that are very different than internet things. So most of it's like in income-producing real estate.

In which state?

Texas and Florida.

And you're just buying like what, like multifamily?

I have some multifamily, I have some mostly single, uh, single family, uh, and then some like vacation rentals.

And you have a manager who— what, like, do you— are you hands-on with that? Is it a headache for you?

So, but it's just like a salary, right, for 2 years?

But even worse than that, right? So I had to— I, let's say I left my job and then 18 months later the book came out, um, from, from like when I left. So $200,000 over 18 months, that's, that's pretty good. But like I said, it hasn't earned another dollar for 10 years. So, so over 11 and a half years $200,000 is not, is not great. But I really, I wanted, that's the book I wanted to write. And obviously it opened up other business opportunities, but I like to be able to do my creative work and not have to think about does it make sense in the dollar and cents. And this is, this is how the entertainment business works as well. Like almost all the money is in the catalog, in owning the intellectual property over the long term. But you can't do that if you are dependent— like, you get paid as an author every 6 months, uh, so, and you're getting paid for the previous 6 months of earnings. Not like, okay, it ended yesterday, here's your thing. You're, you're getting essentially paid from a year ago. Um, and so that's like, you know, that's a— you can be living hand to mouth that way, even if you're a very well-known person who's in, you know, the media all the time. And so I I want to be in a position where that's not the case.

Sean, do you remember like, uh, 7, maybe 2014, I think, basically when, when you and I were just getting to know each other, uh, there was this article that went viral and it said you can buy a ghost town in California for like $1.2 million. Do you remember that? It was like you could buy like an old mining ghost town.

Yeah. And people did, a group did it, right? And I think I saw your note today. Ryan was involved in that.

I think Ryan and his— Ryan, so Ryan, correct me if I'm wrong, I've never met Brent, but my best buddy— Yeah. Oh, really? Okay, so listen to this, Sean. Okay, so Neville is good friends with Brent, so I've heard all about him. So if you go on YouTube, Sean, and you type in like "Ghost Town Brent," you'll see this channel where this guy named Brent, he's this really cool dude who's got like 1.5 million subscribers on YouTube. Uh, he started living in this ghost town that he bought a while ago, but just when the COVID— when pandemic hit, he just moved there and it went to the moon. And it's the best YouTube channel I've watched. Well, anyway, Ryan, weren't you like the— you and Brent were like the mind, the brains behind it. You were just kind of the quiet—

I was one of the investors. There's a bunch of investors. I think we know— you probably know like half of them at this point or more than half. But to be perfectly honest, I thought it was a terrible idea. I was like, you're going to lose all your money. This is not going to work. But I mean, I've known Brent for so long, I just sort of was like one of the small token investors. But I— and I didn't see it becoming what it was becoming. I should have. Like, I was thinking about it in terms of real estate because Brent and I have invested in real estate in Austin before. And so I was thinking about it in real estate. And, you know, being from California, I was like, that area is like like a pit, you know. Anyways, I didn't think about it as a content play. And that's obviously what, what it ultimately probably will become.

I mean, you could make more money off the YouTube channel than the actual— any money you can make off just turning it into a hotel.

That's amazing. So you basically are like, you bought a set. The set actually just kind of functions.

It's like, it's like, dude, it's like 3 coffee. It's like 300 acres in the middle of the mountains. Yeah. Have you seen it, Sean?

No, no, no, I'm talking about the bookshop.

But they say it's the same thing though. I mean, the, the ghost town is an enormous set. Uh, it's a set piece to film and create content and have a, a life and a brand that people care about. You know, and, uh, so, so hold on.

So it's been many years now. So what's actually, what is it today? Is there, I don't watch the YouTube channel. Is there like a functioning town? Do people come visit?

What, what's that? Well, the pandemic obviously made a hospitality business, you know, not very viable. So right now it's, it's mostly just in the sort of rebuilding phase. They're like rehabbing all these different cabins. And then he films, you know, he films videos there and they do like merchandise and stuff like that. It's really, but like my son, like, My son is 5. He watches one of those videos every night before bed. He's like obsessed with it.

It's beautiful. It's like a beautiful YouTube channel. And Brent is very endearing.

And he went— it went from like zero to like 1.5 or 1 point— I forget exactly— over a million subscribers in like 18 months.

Yeah. I mean, he got tons of media attention. It's done like hundreds of millions of views. I'm very bullish on YouTube as a social network. I'm like late to YouTube, ironically, considering that's like what I left school to focus on. Like, I I saw at this talent agency, I signed their first YouTube client. And I remember this agent coming up to me and he is like, what are you gonna do? You're gonna commission their advertising revenue? And I was like, I guess. Yeah. And like, that's like, of course that, that's way better than commissioning checks from, you know, a television series. Because you, this way you actually own, own the stuff. But I've seen it even with, with Daily Stoic, like, Like, as an author, you get recognized like every once in a while. It's actually been weird for me in the pandemic because like I haven't done that much stuff. And so every time I, if I go out or I do something, like I was, I saw someone in Austin a couple weeks ago and then I was, I was just in New Orleans and like, because of YouTube, uh, and, and like Instagram Reels, like the amount of like fans I see in person, it's like exponentially different than what I was getting from like who I was before.

I see you on TikTok like every day. You're in my TikTok feed every day.

Uh, oh, well, I'm sorry to hear that.

Telling me to like, you know, uh, Marcus Aurelius said, yeah, yeah, telling me something some ancient dude is, you know, said about, you know, remembering I'm gonna die or like, you know, not, not being anxious about the future. And I'm like, yeah, actually this guy's talking some sense. Uh, I like it. And, and this, and the, the video quality is actually really good. Um, like, I don't know if you're, I don't know what you're doing for that.

But like, that's like a GoPro. That's a GoPro 9 Hero. It costs $600 and you can shoot in 4K video with a— it doesn't even have an external mic. It's like, it's crazy what you can do.

But you could do a 4K video on your iPhone. But when I upload on 4K, my shit never looks that good.

I think the GoPro corrects, but I don't know. The GoPro does incredible. The, the lighting in the building, I have to say, not something I control, is, is quite good.

Um, well, it looks like you're on like a farm and you're leaning on the post. I do. Like you're in the middle of the, you're like in the middle of a walk.

Yeah.

Uh, I mean, the GoPros are better for outside stuff, but yeah, you just, I mean, you just put it there and it shoots like, you know, super high quality stuff and then somebody cuts it up.

Do you edit or you just hand that off to somebody?

So basically, well, so Ryan, I, I had, I made a living with the Daily Email. Sean, Sean just released this new business that he's working on, which is amazing. Sean, I got to reply to your email. It's called the Milk Road. It's pretty hilarious. And it's like a bit— a crypto daily email that he's working on with his partner Ben. But you have the Daily Stoic, which is awesome. But you have this new-ish thing that seems to be like working out really well. And honestly, I think could be like one of your bigger businesses. I also think it could be bigger because you could sell it because it's not exactly like the Ryan Show, but it's called the Daily Dad.

Yeah, I do two daily emails/podcasts, Daily Dad and Daily Stoic.

Who's, who's writing all the Daily Dads?

I write them all. I write Daily Dad and Daily Stoic. What?

How big is that business or how big is the email list?

Daily Dad is like 60,000 people, I think. It's weirdly not as big as I want it, not just want it to be, But I actually thought it would grow faster than Daily Stoic did, and it's actually been a little bit slower.

But, uh, how big's the Daily Stoic?

400.

Oh my God, really? Holy shit.

And do you advertise to grow these, or what, are you just through content? Then you capture, you know, you make videos and I make content.

Social drives a lot of the signups. And then the book, I mean, the book sold, you know, well over a million copies. Um, but, uh, yeah, so I write both of them and then it's, it's mostly organic, but I'm trying to— I'm having to get more serious about sort of— I think some of the low-hanging fruit's probably been picked, so I'm having to start to think more seriously about it as a business, not just a content that I make.

Man, you, you, you— oh my God, you're killing me. Why weren't you advertising like 3 or 4 years ago? It was so much cheaper. You could acquire email for $1.50. Now it's like $5, $6.

Yes. Uh, I, I should have asked you.

So you, you are hanging out with people all the time that are, you know, super successful. I know a bunch of people who know you and I think you're respected in the kind of like the business world and entrepreneurial world, but I feel like the Matthew McConaughey world. I feel like you, you are, uh, pretty grounded and you're, I don't get the vibe from you that I get from a lot of people I hang out with, which is just like more. More, not enough, uh, I'm not there yet, I gotta go bigger, bigger. And, uh, and really it's just kind of like, I haven't succeeded enough yet, I haven't earned enough yet, I want more money, more success. And I don't get that vibe from you. Are you just hiding it, or is that the case?

Um, I mean, I definitely have— there's definitely a part of me that's in that. I mean, I've written 12 books in 10 years. If I was just like, oh, I'm good, you know, like, clearly there's the drive there, uh, or even some might say a compulsion. Um, I think, uh, so, so there's a part of it, but I, I have— so I've been with my wife since we— since I was 20. Uh, so we met like right as all this stuff was happening. And so, and then I have kids 5 years ago. Um, so I've always been a little bit more of like a normal person. I don't mean that in like a fucked up way, but I haven't been like Oh, I'm a digital nomad, or like, uh, you know, I'm, I'm gonna go live in Puerto Rico for 2 years. Like, you know, like I've been more of just like a regular, like, I don't wanna say a 9 to 5 person, but like I've just been like more rooted in like regular people life than I think a lot of like creative entrepreneurial people I know who I tend to find are a bit more like chaotic. It sounds judgmental, but just it's a different lifestyle. And so I think that's, I think that's a part of it.

No, I know what you mean. Like, for example, right now a whole bunch of my friends are either, you know, like you say, they're crypto rich, moving to Puerto Rico so they don't pay taxes. They're going to Miami because I heard the action's there right now, doing this, doing that. And I'm just like, but, you know, like, I just got— I have two little babies, and I'm like, the idea of moving, like, I mean, the idea of like getting the kids into the car to go to the park is like overwhelming, let alone like uprooting my life in some way, in any way, taking like massive risks now just is not like appealing to me in the same way. Like when I was 24, I remember, uh, I moved, I picked up, I moved to Silicon Valley. I didn't know what I was gonna do, but I was like, this is where the action is. So I'm just gonna move to Silicon Valley. And then I ended up getting, um, this job working with this like billionaire dude in the office. He had this dope office. And I remember I slept in the office like 232 days out of the 365 days. And I was just loving it. I wasn't like, I was being forced.

Nobody's forcing me to work. Yeah. The, the office had an apartment, right? Oh, don't feel bad for it. It was like, it was like a, it had like $2 million with the furniture. It was a love, it was a billionaire. Imagine Peter Thiel's office.

Yeah. I wasn't sleeping in a garage. Like the, the bathroom floor was heated in the morning, so your feet weren't, your toesies weren't cold. So, you know, it wasn't super rough, but nonetheless, I basically was, Choosing to obsess and like go all in, in a way, I was like excited about that and able to do it in a way that I couldn't as real life stuff layered on, like relationship and kids and things like that.

Like I remember when Clubhouse blew up like a couple months ago or 6, I was like, what? Like I, I was like, I don't even wanna go to a real conference, let alone be in like an internet room conference. Like I, it, it was just totally inconceivable to me. That anyone would want to do it, have the time to do it. That's so— that's sort of not been like— I actually like writing, you know what I mean? So the other part of it is, is not just like the sort of wanting to have more of a normal sort of rooted life, although I feel like I do weird, unusual— I take risks in other ways, like living on this farm and stuff. But it was also like, for me, like, I— writing to me is a calling that's a little bit different than, I don't know, um, making money in crypto or something. Like, it's, it's a blessing and a curse, right? It's a blessing in that it's fulfilling, it gives you purpose, it's artistic, it's like a thing you master. There's also, I think, a ceiling on it, you know? And like, you can, you can be good at it. There's obviously the J.K. Rowlings of the world, but like, you know, um, but there's not a ceiling to being famous.

I mean You know, we're both friends with Tim Ferriss and like his fame allowed him— I don't know what he's worth, but he's probably worth hundreds of millions of dollars because of his investment.

Yeah.

I mean, there's not a ceiling on being well known and getting access to—

No, but I mean, you sort of— you end up in different niches, right? If you— if you're called to be a poet, you obviously would be more lucrative to write business books. But like, you are where you are. You know, there's a certain amount of like you don't choose what muses visit you. I know that sounds a little mystical, but like I like— sometimes people have been like, oh, he's writing about stoicism to get rich, which I always laugh at because like, again, I— if I— if being rich was what was motivating to me, I would do literally anything but this, right? Like, this is the worst possible of the things to affect. Um, but I guess my thing is like, I, I really like the routine and the ritual of sitting down to write, which is also, I think, inherently a bit grounding in a way that like some of these other pursuits maybe aren't.

What does your, uh, normal workday look like? I mean, are you doing like a 9 to 5?

Uh, not 9 to 5. Like, I wake up early, uh, I go for a run or a walk with the kids, whether we're at my farm or my place in, in town. Um, I don't check my phone in the morning. Uh, I don't eat in the morning. I usually journal in the morning, and then I go— I write usually for 2 or 3 hours, um, and then the rest of the day after that is business, other work stuff. And I'm, I'm done by 4 almost every day, so I probably work 8:30 to 4.

Seems like a good ask.

I like it. I try to, but I, I like— it's important. There are also— I, I don't know, to me, being really great at what you do and somehow managing to be like a somewhat normal person, um, to me is actually like a rarer thing to do than to, to just be great at what you do. Like, I think if anyone decided to be like— Tom Brady's Tom Brady, but there's a cost to being Tom Brady. But like, if you choose to be that singularly dedicated to what you do, it's easier to be better at what you do than to say like I'm going to work 9 to 5 and be like great at what I do, if that makes sense.

So you used to work for Tucker Max. You then became buddies with him and you had a business together. But I've never asked either of you about this. You've probably— it's based off of some of the stances I know that you've seen. You've written some great stuff about like a letter to your dad about voting for Trump. I know that you're against like some— a lot of these statues. And you've donated money to that. And Tucker, I think, has gone the other way where— I wouldn't— I don't want to call it the opposite because of course he's probably against a lot of the things or for a lot of things you are, but maybe different. And he actually recently came out this article that Sean and I talked about. It's called Doomsday Optimism, and it's about how very bluntly— but he's such a good writer that like everything he writes, it seems like convincing. But basically he talks about how he thinks like the American government is basically going to collapse in 2 to 4 years. And how he's preparing for doomsday. And it was like crazy fascinating. But I— what is your opinion on that? I've been eager to ask you what you think about that and what—

if you have an opinion on it. Tucker was very good to me early in my career and set me up for the success that I've had. So I feel very grateful for that in a lot of ways. He and I live in very different realities now. I think, I don't know exactly what caused that or what, what the driving force of that is. I mean, I have some theories, but a lot of that stuff that I see and read, I think it probably has nothing to do with whatever he's talking about. It strikes me as, as driven by driven by something else, um, which I've seen a lot of. Like, I think the pandemic brought it out in a lot of people that probably— so we both know, but I've noticed a kind of a radicalization or, uh, uh, an untethering from people, um, that otherwise I would have assumed were in, in alignment on. I've just noticed, uh an untethering that I don't— I don't know where it's going, but it certainly worries me. Is that a diplomatic answer?

Yeah. And I don't really like that answer because I understand what you're trying to do. I think you could— you could not agree with his opinion and still be respectful towards him. But I understand that you're trying to, like, keep it, you know, be cool. But like, in one regards, I could be like, well, I understand. I actually could see Ryan thinking almost something similar because he lives in the country and he likes privacy. And like, he, you know, you're like so, so high IQ that high IQ people typically are like quirky and have like weird opinions. But then on the other side, I know like some of the things that you stand for and I could see you just laughing at that being like, what are you ridiculous? Uh, but it's, it's, it's, it's weird.

I, I've noticed this sort of trend in like sort of tech entrepreneurial people where— I don't want to say fads, but it's almost like these idea viruses sort of enter the community and some people end up taking them to like very strange extremes. So like polyamory was one a few years ago, and then crypto is one. I, I, I have— like, I'm not anti-crypto. I, I, I think there's a lot in crypto. I'm invested in it too. But then, then, then in the pandemic there was Like, then there was this sort of anti-vax, anti-lockdown, anti-COVID denialism. That was one. And then I'm very alarmed by some of the people that I know in that space that are now going in sort of like a— it's worse than a Trumpian direction. It's more of like a January 6th, like end of the government, like a, like a toxic Uh, like, we gotta buy guns, and I have guns, but there's this like almost like, uh, like doomsday, like disaster cultish direction that it's going in. And I don't— it strikes me as coming from somewhere other than like what they actually say it's coming about. Does that make sense?

And by that do you mean, uh, the belief is coming from some other like kind of reasons or the motives, meaning like, uh, like they're trying to make money. Yeah, like if we perpetuate this, we'll get more notoriety, we'll get more money, we'll get more attention. Like, you know, there's some people like clickbait is in general is that, right? Like, I may not believe this. Like if you watch a sports talk show on ESPN, they don't necessarily think that LeBron James is better than Michael Jordan, but they know if they say it, it gets clipped and it gets shared. And so there's like this, yeah, I do, I perform. Versus like, do you think that the belief has come from somewhere or the motive might be driving them to extreme, you know, radicalizing?

Right. There's a— there's this chart I saw that was amazing. It was in a crypto annual report. And it said, you know, what are some of the underlying things that drive this? Like, crypto is like a religion. It's like a cult. It's like, you know, this very, very strong— it's not just the same as like, I like this business, I'm going to invest in this asset. You know, people don't feel the same way about Bitcoin as they do, you know, a piece of property in Dallas. And so it said it was this chart and the chart basically was on the, on the, on the Y axis. It was like, do you believe it was about institutions? It goes, do you believe that institutions are like credible or not credible? Meaning like, are they honest or are dishonest is I think the way they put it. And then on the other side was, are they competent or incompetent? And it's like, rank these institutions. It was like the US government. It's like dishonest, not, not competent, incompetent. And then it was, um, the CDC, and it showed how they've been moving over time. And basically every institution that you could think of, whether it's universities, whether it's health organizations, the NIH and the WHO and CDC, whether it's the US government, they are all sort of traveling towards dishonest and incompetent as the general public viewpoint of them. And this has a bunch of implications. It's like, well, so the things that reject institutional beliefs, so you see Joe Rogan just explode in popularity. You know, his show is bigger than quote unquote mainstream media. He is more mainstream than mainstream media, but his brand is not an institution and he doesn't look like them. He doesn't read off a teleprompter. And so he's got this like appearance of higher honesty, higher competency. And so the same thing is true with crypto, which is non-government money and blah, blah, blah. And so all these things are like on trend right now. And that doesn't necessarily make them more honest and competent, but it is the perception that's going on.

Yeah, and when I was listing the different things, the other one I'd put in there is I think like psychedelics is another one where it just becomes becomes like this idea virus. And I'm not saying that I have a disagreement about it. I'm just— it's very interesting how these things just sort of infect these different subgroups and become almost a new— it's their identity is primarily in that the— it's like it's very tempting to fall into a thing where you're smarter or better than other people, that sort of outsider mentality. And so I think I'm just— I'm very wary of how that's affected people that I know, and I'm worried it's taking some of the more fragile people into a dark, potentially dangerous direction where they're just— they're fucking with things that once you fuck with, they're very difficult to unfuck.

And speaking of psychedelics, and we'll wrap up in a second here, um, I saw— I follow, uh, so we've talked about Aubrey Marcus on the podcast because Aubrey has a crazy story because his dad, like, in invented like the Fleshlight and then he like kind of parlayed that into building this awesome supplement empire. But I got this Instagram ad or maybe I just saw on his page. So Sean, I don't know if you saw this. Aubrey Marcus, the guy we talked about. Yeah. He has this documentary where somewhat recently he spent, I think, 7 days in complete darkness. Like, and I heard maybe it was in Cerro Gordo. Am I getting the details?

No, it's definitely not at Cerro Gordo. Oh, I know he has a ranch in Sedona. Maybe it was there.

Okay, well, for some reason I thought it was at yours. Okay, I'm wrong then. But did— am I right though in that it was like 5 or 3 or 7, like multiple days? It complete pitch dark.

I don't know. I have not heard about that, but I am, uh— oh man, I like Aubrey a lot. I've known Aubrey a long time, but he's— I, I'm a little worried about him.

He, he's a wild man, Sean. You didn't see this.

So what was that idea?

Why did he do that? Okay, so I, I, I— so basically he had a, a night vision camera looking at him, and he was in a small room with a bed and basically pitch dark. And after 24 hours or something like that, he kind of starts hallucinating and kind of goes crazy, and he's talking to himself. And the whole documentary is, uh, is basically showing the night vision camera of him talking to himself, and then like a voiceover and flashbacks of him talking, like, what he was experiencing to that point. And he was trying to go through, like, almost a psychedelic experience, because I guess there's something where— I, I don't know the science behind it— where you're in the dark for a long time, you start going nutty and have some realizations. I don't know if it's true or not, but it was fucking insane. It was crazy. I mean, it— the way that I see it is, like, to me, it's like, I don't care if I'm an outdoorsman. If I see a huge epic mountain, I'm going to be in awe. And that's how I was with Aubrey Marcus. In this documentary. I'm like, I don't care about drugs. I don't care about this guy that much.

You just saw the ad?

I just saw— I, I watched parts of it. I started watching parts of it because he released like 5 minutes at a time on his Instagram, and I started watching parts of it. He is— it's the fucking craziest thing I've ever seen. The guy's insane. Uh, you have to watch this shit. It is wild.

Does he come out okay at the other side, or you haven't gotten to the end?

Well, this was filmed like a year ago, like Instagram, so, so we assume it all worked out okay.

Well, I— the reason I didn't buy it is it I'm afraid. I'm kind of afraid to watch it. But like, he's wild, man, because I watch his Instagram and I see some of the shit he does.

And I'm like, this is—

I'm just— I'm very— I'm very concerned that these people are messing with their brain chemistry in a way that it's hard to come back from. And, you know, I am— I am not a fan of this sort of like prescribed medicine for yourself to heal unnamed traumas. Like, I think it's going to end very badly. Maybe I'm a little conservative and I'm missing out on something, but I don't think you should fuck with your brain the way some of these people are fucking with their brains. And I think it's going to— I think we're starting to see some of the ramifications of it with some of the stuff we're talking about here. But I think this is hard to put back in the bottle.

Yeah, this is wild. This is—

are you looking it up?

Yeah, I'm reading about it right now.

What does it say? Is it 7 days? It was like days.

So like, okay, there's a part of this I can get behind, which is like, you know, people, whether they go try to climb Mount Everest or Wim Hof getting in a cold, cold bath every day to like, you know, challenge themselves to like, uh, like it's a, you know, there's a form of meditation, for example. So he says, my thinking was this, if the prospect of sitting in the dark with just your own thoughts frightens you, maybe that's exactly where you need to be.

Oh my God. No. Rattlesnakes scare me too. I don't need to get bit by rattlesnake.

And so, oh, on it, for me, there's a part of this that I actually like. I get part of that, which is like, um, I think the more comfortable you could be with yourself and by yourself and not need stimulation, not need others, not need constant entertainment— I do think that that is like a direction personally that I would like to go in, where I can, I can be at peace and happiness without something going on. Now, in this, and this one I think is less It— to me, it's less scary than like being like, yeah, I'm gonna start microdosing LSD, or like, I'm gonna go on this ayahuasca trip in the fucking forest because I heard Joe Rogan say that it was transformational. To me, that's like way higher risk and, um, maybe not necessary compared to, you know, I guess this darkness thing is a little bit less permanent feeling for me.

But that's what they do, but then I also just think to like break them. I, I don't think it's something you want to be messing with.

But again, yeah, maybe it is like deeply traumatic.

I'm not sure. Hey, you know what the phrase is? Whatever doesn't kill you makes you weaker.

Seriously, man. I don't, I don't know.

I'm, whatever doesn't kill you fucks you up really bad.

I always read these as, to me, these are like, um, these are content stunts, right? This is no different than Jackass and, and a bunch of other things. Like maybe some people come from a good place and I'm just kind of skeptical about all this stuff. Like for ex— I'll give you, Ryan, I'll make it personal for you, which is like when I saw the Daily Stoic, I was like, oh, that's smart. Stoicism is this growing trend. He probably likes stoicism, but like you can like it without having to do all the work of creating a daily email and content around it. Like that is the opportunistic side of this like kind of cool niche thing that's clearly growing. And I've said, I, I'm, I don't know you, right? So I'm just thinking from afar, I'm thinking, oh, that's smart. Um, and you know, he probably recognized this growth and said, okay, I could build a cool brand around this thing that I like and I see is growing. And so when I see, uh, and you know, so for example, if I see you making a TikTok every day about stoicism, I think to myself, well, you know, uh, I don't know how much of that is like, well, this content is gonna work, so I'm gonna do it. Sure. Versus I really just needed to get this off my heart and share this with the world.. So similarly, when I see, you know, these stunts, I think to myself, well, they know this is content that's gonna hit and they can get a bunch of attention from it. And like, did he really need to do this and want to do this? I'm not sure. Right. Those motivations get mixed. I know for myself they get mixed because, um, you know, if I, I've had a bunch of tweets go viral, I, you know, I added 200,000 Twitter followers last year. It's very addictive. And in, uh, I don't know if you saw his, uh, the, the, um, the standup special that, that Hasan is doing right now. Oh, it's so good.

Did you see him when he was in Austin?

He has this part in it.

Did you see when he was in Austin?

But like, his wife was like, dude, you have to figure out how to keep that on a leash.

Maybe you shouldn't be poking the bear. It's really important. And that's kind of what you're talking about, right?

There's a price. You gotta figure out how to keep that on a leash. And I think about that a lot. And I think about it, you know, even with what I do. I remember I was, uh, I was on some big morning show. And I remember thinking like, there's a— I know what I could do to make this like national news. Like, I, I know I could, I'm, I've got a, you know, an audience of several million people right now. What I, what— and then just going like, life is too fucking short. And I also, I want to continue to live in reality. And so I think what happens is certain people get desperate or maybe their judgment is not good or they don't have someone in their life that's like, eh, you know, that could work, but What about this, this, this, and this as a consequence? And, uh, you can, you can become unhinged very quickly, um, especially if there is any also, you know, uh, comorbidities with like a mental illness or, you know, like, and so I, it's most of the people who want to be in the public eye, you're already a little, you know, like that, uh, and so you got to be really, really careful. And I'm, I'm worried about where some people I know are going.

Yeah. Sam, as a fitness influencer, I've been wanting to talk to you also about your, uh, excessive exercise and what this might be leading to.

Hey man, I got—

you might spend 3 days in darkness only doing squats, uh, just to, you know, hit the, hit those views.

I'm in a good place, my friend. I'm, I'm doing everything right at the moment. We'll see how long that could last. Ryan, this has been awesome, man. I, I appreciate you coming on. This is fun. Thanks for coming in. We didn't even say the name of the book. Courage is Calling, right? It's awesome. I've not read that one yet, but I'm going to buy it. I've read everything else. Perennial Seller, Obstacle is the Way, Conspiracy. I guess I've read 4. Conspiracy and Trust Me, I'm Lying. And then the middle 2 are—

There's the Stillness one. I haven't read that one.

Stillness is the key. And then Ego is the Enemy is the one I think you're missing.

Ego is very good, and Obstacles Away is very good. Those are both, both great.

Well, and you're awesome. I appreciate you.

Thanks for coming.