Ryan Holiday Reveals How Much Best Selling Authors Make, Crazy Peter Thiel Stories & More (#370)

And then I Googled like Mark Manson house because that's always like the tell on like, is someone like crushing it? Because you can't really like— it's hard to get a mortgage for a $15 million house unless you're actually raking it in. And it said like, you know, Mark Manson sells Tribeca condo for $14 million. And I'm like, damn, like, I thought book— the book business was a bad business. He must have crushed it. He must be making millions. My man, Ryan Holiday. How are you? Nice to talk to you.

It's good to talk to you too.

Um, so you, you, you asked to come here and I'll just, cause I just want to get it out of the way. I want to give you the love. You asked to come on here because A, we're homies and I love you. And also because B, you have a book coming out. What's it called?

Discipline is Destiny. This is the new one for the series. Uh, and yeah, it came out yesterday.

Oh, and how's it going so far?

Really good. Really good. It should be significantly higher. It's already significantly higher than the last one. And then you're— so I, I know where the numbers are, but I'm waiting. Well, the one thing you don't know until the end of the second week is audiobook numbers and, uh, where it may or may not land on the bestseller list.

What do you think is the outcome of this one's going to be?

Um, we'll probably come in a bit above 40,000 copies the first week, I would, I would venture to guess. Uh, could be higher if they keep trending this way. So because I have my own bookstore and I did the sales through my own bookstore, I probably won't hit the Wall Street Journal list. Uh, they've, they, uh, they skunked me last time. And then the New York Times list is let's say 50/50, all of which my publisher is very concerned about. And I have decided that I don't care about at all anymore.

Because if you own your own bookstore, that means that— and you sell 20,000 copies, do they not count all 20,000 in the rankings?

Yeah. So I mean, just generally, if you sold 20,000 copies of a book through one bookstore, they would find that to be suspicious, uh, or, or unrepresentative, and there's a chance it could get tossed. If you ever look at the, at the bestseller list and you see like a little— they call it a dagger, it's like a little cross next to certain books— that means that there was a lot of bulk purchases, um, or like suspicious activity. So there could be that, um, but, uh, the, the, the Wall Street Journal or BookScan, which is owned by Nielsen, just flat out told me they just don't include, uh, sales from, uh, stores owned by the author anymore, uh, which doesn't strike me as that being a big enough category to have a rule about. But, um, I guess it, there's the potential for fraud. Like, I guess theoretically I could have just, you know, inflated the numbers or something. So, so there's a chance it could get tossed. But as I have gone on as an author, I've cared. Once you get it once, I feel like you have it. And then you also realize like kind of how meaningless things are. Uh, so I care a lot less about sort of the status, uh, or the recognition of sales. And I care a lot more about, you know, did I sell as many copies as possible? Uh, to as many people as possible. Right. Um, cause the whole point of writing a book is for people to read it.

Does being on that list, and when you say the bestseller list, are you meaning just the New York Times? Is that considered like the list? And does being on that help sales?

There's, there's sort of 3 lists. There's New York Times, which you probably rank as number 1, Wall Street Journal, which you'd probably rank as number 2, and then USA Today. Those are the 3, uh, what you have to hit one of those 3 lists to be called a national bestseller. Those are the 3 national lists. Um, there is, I think people tell themselves a story about how being on the list helps them sell more copies. But as someone who buys a lot of books and talks to a lot of people who buy a lot of books, I have never once heard of someone buying a book because they saw it on a list. Most people don't even know where they would find such a list.

Dude, I was reading, um, uh, is it News Corp or I forget the company, the, the, it's Rupert Murdoch's company, but he has two of them. I forget which one is, uh, that owns, I think Penguin. And they did this whole, I was reading their annual report and they were doing this entire section on Mark Manson. And basically saying like, this has been like a breakthrough hit. And like, this is a, you know, the company is like a $20 or $40 billion company and they're referencing Mark Manson. And I'm like, oh, wow, that's— that must be a huge book in order for them to like discuss this in 6 pages of a 100-page document. And then I Googled like Mark Manson house because that's always like the tell on like, is someone like crushing it? Because you can't really like it's hard to get a mortgage for a $15 million house unless you're actually raking it in. And it said like, you know, Mark Manson sells Tribeca condo for $14 million. And I'm like, damn, like, I thought book— the book business was a bad business. He must have crushed it. He must be making millions.

It's actually a great business. So the, the publishing industry, I think, is about a $40 billion industry. News Corp owns HarperCollins. HarperCollins publishes Mark Penguin Random House, which is my publisher, is the biggest publisher in the world and they are themselves— let's look, Penguin Random House.

I think they're owned by a parent company. I forget what the parent company is.

They're owned by Bertelsmann or something like that.

Yeah, yeah, yeah, that's right.

But, you know, let's— revenues, their revenues, I bet, €4 billion for Penguin Random House. So it's a it's a very big business, um, uh, and, and always has been. And there are multi, multiple, multi-billion dollar, you know, businesses inside that business. Even, even Ingram, which is the distributor that sells books to most independent retail, is like a $7 or $8 billion business. But Mark's probably sold, I think, um, I think, uh, Subtle Art of Not Giving a Fuck sold like 10 or 15 million copies.

And what do they cost, $20?

Yeah. So, so if you think about like my books, I've sold 5 million copies. If you said $20, that's, that's $100 million in gross revenues right there. Right now. Now, obviously there's a lot of middlemen even before it gets to the publisher, right? The publisher is selling the book at wholesale. So right there, that's, you know, cuts it in half and then, you know, blah, blah, blah, blah, blah, it goes down. But, but there are— if you think about how much a book sells for and the quantities of which successful authors sell a lot of books, that, that number gets very, very high. This is why J.K. Rowling is, is a billionaire, right? She's probably sold 100, 200 million Harry Potter books, not including licensing and all the other things, you know, uh, different— the, the different formats, whether it's audio or ebook or physical or hardcover. Even hardcover and paperback is a big thing, like One of the— I bet Mark, for instance, that I know Mark and he's amazing. The distinction that the decision to put your book in paperback is actually a multimillion-dollar decision for authors. And most authors have never even thought about this. So for instance, on a hardcover book, um, the, the standard publishing contract and pretty much everyone, including the authors that are, uh, household names are on the same contract. It's just, this is what it is, is, uh, 15% on hardcover price. So, uh, an author makes, you know, 15% of $27, whether you as the customer get that book for $17 on Amazon or for $27 at an independent bookstore, you're making the same amount, right? Your, your royalty is on MSRP, but 15% of hardcover, right? A paperback. Sells for about $10 to $15 less than a hardcover, right? But, and your royalty is 12.5%. So my agent very early who was in publishing, he was like, he was like, I will never let your books go into paperback. He's like, you have to sell about as third, you have to sell a third more books to make the same amount of money. That you've sold in hardcover. And this is why Tim Ferriss's books are not widely available in paperback. Good to Great by Jim Collins, which has sold tens of mil— you know, probably 10 million copies still in hardcover even though it's a 20-year-old book. So there's lots of little decisions that—

what about Audible and ebook?

So Audible, you make, uh, I think it's the same as, uh, I think Audible and ebook are 25% of list price. So you make it, it's a higher royalty, but on a lower price point, audiobooks are like $15 or $9, uh, for, for eBooks a lot of times. Uh, so, so somewhere between $2 and $3 a book you make across formats.

So if you're in hardcover or ebook, and so you think Mark's book has sold 200 is, I think, did you say 200 million in sales?

So no, no, 20, he's probably sold 20 million books.

Sorry, in gross revenue.

Oh, uh, was it 20 million books times hardcover price? Or, you know, it, it, there's going to be a, a blend there of the price. The only, the only thing that's worth pointing out, and this isn't a criticism, uh, it's a, it's just a quirk of the business. Mark has sold a— Mark's books are very big internationally, right? His books are big in Brazil. His books are big in India. Uh, I, I've experienced the same thing. But as soon as you start, like, so as soon as you start selling lots of copies internationally, let's just say you start seeing a lot less money for those titles, right? Like, for instance, somebody sent me a copy of one of my books in, from Iran recently. And I emailed my agent and I said, oh, I didn't know we did like a Persian translation. And he said, we didn't. He said, Iran doesn't recognize copyright. They just do whatever they want. He's like, you'll never see a penny from these books. So the point is, like, if, if you sell a million books in Russia, right, you're not getting your standard royalty rate. You may never see a penny of that. You might get an initial advance, but you, you know, you start to get into, let's say, less transparency in the accounting as you sell. So you can't, you can't simply go, well, what's the total number of copies sold by a person? And then times that by a number, you're probably going to be overstating the cash they have on hand.

So you've sold $100 million in books. So then like the estimate based off of the numbers you said, it would be like around 13, 14, 15% take-home. I mean, how many authors are doing that?

Selling 5 million books? Uh, very, very few. I mean, definitely there are a lot, there are lots of people who have done it and there are people who have done much, much higher than that. But like, as far as people who write about philosophy, I mean, I'm not sure it's been done ever. Certainly not in, in, in like the modern world. So, you know, when I went to my publisher and I, you know, offered them an obscure book about ancient philosophy in 2011, 2012 for, for the Stoic book, for my first Stoic book, you know, they offered me my, my advance on The Obstacle Is the Way was $75,000. They were not, they were not thinking, you know, that series would sell 3 or 4 million copies.

Do you think that your life has or will become— so we were talking about Tim Ferriss and we're like, you know, however much he's made on books, it probably pales in comparison. He's arguably like just guessing, maybe he's worth $150 to $250 million based off of his Shopify and Uber and Seed investments. And who he probably has done so many more things that I don't even know about. Do you think that your business is going to be a similar thing where it's almost like the books are awesome, but they're going to be tiny compared to the other revenue streams?

I don't know. I don't, I don't do that many investments, but it is weird. Like, I, I was an advisor early on to like ButcherBox and they've done a few sort of private transactions that I took part in. And it is both humbling and surreal to be like, to get a check and be like, shit, I would have had to sell a lot of books to get the same amount of money. And this amount of money was, you know, a lot less work. So I think for someone like Tim, you know, when, when you can, when you can invest in something that scales at that level, it— I do think it makes you a little disinterested in the economics of publishing, even though they are quite, they are quite good.

I, yeah, I mean, I was like, and everyone talks about in writing a book and they say, I think he's the one who told me this. He's like, it sucks. He's like, it just, it stinks. He, he says, he goes, I love it kind of, but I also really hate it. It's very uncomfortable and it's a lot of hard work. And I was like, yeah, I don't know why you'd write a book then when you, if you don't have, if you don't, if you don't truly, truly love it. I have no idea if he does or does not, but it's very hard. It seems, it seems almost impossible.

It is super weird though, because, like, a lot of wealthy people read books, right? The, the interesting thing about books is that they sort of punch above their weight culturally. It's like the opera or something, right? And so, like, you could be very famous on YouTube and your average billionaire might not know who you are. But if you write like a business book or a political book that sells reasonably well, you're going to, you're going to have some name recognition in an elite group. And so I've gotten to meet like a number of very successful business people over the years. And like, as a rule, they all want to write books or all want to talk about whether they should write a book or not. And it was actually very helpful for me to learn that early on because like every author I knew was trying to start a business or follow in Tim Ferriss's footsteps and invest in these companies to get really, really rich. And then I would meet really, really rich people and they wanted to write books. And it was a reminder to me that like, uh, doing stuff that's cool that you like, that, uh, means something to you is what people do with their money when they have it. And so they're like, like I met this guy, uh, you actually probably know him, but I won't put him on the spot. But anyways, he, he'd written a couple books and then he started a VC, uh, company. Uh, uh, he raised a fund, he raised like $100 million and Uh, he had to put writing on the side to raise this fund. And I asked him, you know, um, like, why, why are you doing this? Like, what are you gonna— I was like, let's say you really succeed. Like, let's say your fund crushes and you walk away with like $20 million. Um, what would you do with it? Right? And he was like, he's like, do you know who Alain de Botton is? He's an author who started this company called School of Life. Uh, he was like, I think I would do something like that. And I was just, I just burst into laughter because like, he was, yeah, he was, it's like that, that story about the, you know, the fishermen, uh, who meets that Western businessman who tells him like, you know, if you really scale up your company, blah, blah, blah, blah, blah, you know, one day you can sit on a beach somewhere. And it's like, that's what I do now. And so there is kind of this weirdness where people think financial freedom is this kind of abstract good. And then you meet people who have it and they still have to wake up and figure out what they're going to do all day.

Dude, I listen to your— I want to talk about the YouTube thing in a second, but I listen to your YouTube videos every single morning when I take a walk. Oh, and like, it makes me feel so good about myself. Not maybe not good about myself, but I feel like I'm getting so much from it, whether it's education, whether it's just like you're helping me think differently. I don't know what it is, but I get so much from it. When you, you're the one creating all this stuff, or at least you're paraphrasing like interesting people. Do you think that you are absorbing these lessons better than most others? Like, you know, like, are you, you, you just told this very simple story of like, well, why would you go and do this, this, and this when you're already doing that now? Are you motivated by, like, are you motivated by money? Are you motivated by all these things that you talk about? Like, look, this and this and this may not make you happy.

I think, uh, I, I certainly struggle with it like every, you know, single person does because it's not like just knowing it doesn't magically make it easy. But I would say like, like a big lesson like that, like why are you trying to make all this money to get somewhere you're already, you already could be. I feel like I do a better job learning those, those big philosophical lessons, like sort of where do you rein ambition in, you know, sort of how do you define meaning or happiness or contentment in your life? I probably am better at that than I am at some of the more basic stuff. Like, you don't have to be anxious about this, or like, why are you letting this person get under your skin? Or why are you losing your temper about X, Y, or Z? So like, I feel like the bigger stuff, the stoicism or the philosophy sort of connects with me. And by the way, that story that about the fisherman actually traces back to like the 14th century about It's this story about a prince advising a king or an advisor advising a prince. So the story goes way back. I feel like I get that better than I do stuff that might seem really easy for most people, which is just like, you know, sort of day-to-day emotional management.

How you said something really cool on the, I was listening to this the other day. There's two things that stuck out, but the first one is with Matthew McConaughey, you're talking about content. And you're asking him about how, what he chooses, like which projects he chooses. And apparently he, there was, oh, the whole part of the episode was talking about how he had like $10 or $20 million offer and he was like, nah, I don't wanna do this. This doesn't, this doesn't speak to me. This is not how I wanna spend my time. Yeah. And he was like, he felt guilt over that. And you guys were talking about Bob Dylan and I think it was you who said, I wanna make content like Bob Dylan, which is quality and quantity don't necessarily have to be at odds with each other. Like I can output lots of really cool, great stuff. And you do do that. And the Daily Stoic is an email. Then you have the Daily Dad, another email, and then you have the books, which is, you have dozens of 'em or a dozen of 'em plus. And then you have, uh, the podcast and then you have the YouTube channel. And I'm like, how on earth are you, uh, how are you outputting all of this stuff? It's always awesome. I love all your shit.

Well, thank you. I mean, I, I, I think I actually, like, I actually like doing it, right? So there's, there's some people who they don't like doing it and And so to do it because you think it'll make money or it's what you have to do, um, that would be not a reason to do it. But like, I, like this morning I, I got up and I wrote and yesterday when the book came out, I was excited not to come into the office to see how, you know, the, the discipline did, but like I had saved like a really good chapter, uh, for what is the sequel, cause I'm doing this 4-book series. Like, I was just fucking pumped to do that. Like, that, that's really what gets me excited is doing the stuff. So I've always— I think I tend to have more energy to make stuff than there actually is, like, pipes to put stuff out. That's just like how it shook out. And I agree, like, I agree with the sentiment re Bob Dylan in that, that like quantity and quality don't have to be opposed to each other. And in fact, uh, the more you do, chances are you'll, you'll sort of get something magical or important. I mean, like, I, I really admire people who are wired differently and they sort of painstakingly, uh, put, uh, you know, put lots of years into something. Although, like, if you, um, you know, I bet if you asked Mark Uh, he would, and I actually, I have asked him, but like following up a massive, massive hit is really hard. And I've been lucky in that my books have done well, but they haven't done so well that like my whole world changed. Like when The Obstacle Is the Way came out. So Obstacle Is the Way came out. They didn't offer me very much money. It sold well at first, but it, it took.

When it's like a slow burn.

Yeah, and, and not even slow, but just steady. Like, it probably didn't cross the 1 million copies sold mark. I know it crossed the 100,000 copies mark within the first year because there was a bonus attached to it. So it took, you know, 12 months to sell 100,000 copies, but it probably took an additional 4 to 5 years before it crossed the 1 million copy mark. So like for someone like Mark or James Clear or other, other people, like it would— they, they hit the 1 million mark in like a number of months. And when you start to do that, everything changes. Expectations change, uh, you know, inbound inquiries change. Um, and I think, I think it becomes hard to just like do the thing. So I, I feel like kind of lucky to be like to have a niche, but to have a big niche, but for it still to very much be a niche, right? Like, there's just more people haven't heard of me than have heard of me, and that is a nice place to operate in.

Dude, so many people, so The Hustle, we are a daily email, and then me and Sean do this thing 3 days a week, and people are like, hey, how are you doing quantity? I wanna get started, but like, you know, I'm like, banking 21 episodes before I start, or I'm like perfecting like this blog post and, you know, I, I'm going more for quality versus quantity. And in my head, or sometimes I'll tell them, I'm like, no, that's a false dichotomy. That, that's not true. Like the quality is the quantity. Uh, like, you know, like the, the output here, or like the, if this were, uh, like quality plus quantity equals, it would be like, uh, you know, like the total reach and how impactful they are and the types of people you're impacting. And to do that, you have to have like something in there for quantity. And it's really just kind of an excuse to procrastinate further that you're making up for yourself. But A, it gets easier as you get into it. So you need quantity, you need the swings to get better. And B, if you treat it like a job, you could have way more output than you think.

Yeah, I, I have a couple thoughts there. So one, it's like try to apply that logic to like any other thing. Like imagine if you met a comedian and they were like, I'm really focused on quality instead of quantity, so I don't do a lot of stage time. Like, I just don't go up very often. You'd be like, you're a shitty stand-up comic. Like, the way you get good at it is by doing it a lot, right? And it's very hard to get to quality without years of, uh, back and forth with an audience, right? Like, it's just really hard. And so especially online where you're giving the thing away for free, like you should be focused on quantity because quantity is how you get to a place where what you do is worth paying for at a premium level, like with a book or something. So I like— I've done a free email every day for 6 years, right? That, that's built a business.

But you writing that?

I write it every day. I mean, every once in a while, like Like, let's say 10% of them are, you know, hey, I'll work with someone on my team, be like, hey, I already wrote about this. Can you work this into a draft for me to approve or rewrite? But like the vast majority of those daily emails were like 100% original ideas that I put out 100% of. I have systems that make it easier. Both, both.

You're, you're, oh, I didn't know you're writing both of those every day.

Yeah. Well, I don't write it. I mean, I write every day, but I don't write the email every day. Right. So like I'm currently, let's say like I could pull this up. Let me, I have a document, um, where I have someone track them. Like I am, I'm scheduled out on Daily Stoic through and Daily Dad through October 14th. And then I have 10 written that are ready to record. 16 that are recorded but not unscheduled. And then 9 on Daily Dad that are ready to record and 8 that are recorded but not scheduled.

So like, that's your system.

Yeah. So I'm just do it. Like I might sit down today, like I have, I don't know where my to-do list is, but on my to-do list, I have 3 sort of one sentence ideas for Daily Dad emails. And I might bust that out in 30 minutes and then that's you know, almost a week worth of content right there.

Are you writing the scripts to your YouTube videos? I think you're only doing 1 or 2 a week, right? Yes.

So YouTube, I have a— I have a— I have a— actually, wait, let me— I'll come back to that in a sec. The other thing I would say about the people who are like, oh, I really want to get to quality, that's why it takes so long. When I look at what those people make, I very rarely see the quality, right? Like they're like, oh, you know, this book, it took me 5 years and I'm like, where? Show me 5 years of work in this thing, right? I'm not arguing with you that it, it transpired over 5 years, but I don't think you showed up and worked on this, as you said, like a job every day for 5 years. I think it either— because if that were true, I think it would either be a lot better or I think it would have come out a lot faster. Right. So I think a lot of people are baking in a lot of inefficiencies and a lot of, uh, procrastination inside that. And then patting themselves on the back and saying that they're doing a thing that they're really focused on quality. So that's just like a dispute I have. I think a lot of people take way too long to do things. Um, when, when I see like a Robert Greene or Robert Caro or, you know, one of these greats, I'm like, I see the, I see the 5 years. Like, it's obvious. Like, You were like, Robert Greene was telling me the other day, he's like 7 months into a chapter on this book that he's writing right now. And when I read that chapter, I'll see every fucking day, right? Because like that, he's not lying.

Dude, when I read Robert Greene and the, what's his, what's Carol's book? Moses.

Yeah, the Robert Moses book.

Robert Moses. And then I just got done reading The Rise of the Third Reich. Which is like, which is like a 1,500 or 1,300 word like epic. And then pretty much like Titan is like this too. Anything Ron Chernow does.

Yes.

Every sentence has like, to me it's like a life's work. And if they're lucky, they can maybe get 3 of them. Yes. And I read those things and they make me depressed because I just think like, I, I can never do anything this detail-oriented, this beautiful. Like it, those his— it's, I think it's mostly history books. Every single sentence. Is amazing. And I don't understand how you could do that for so long.

Yeah, this is the William Manchester series on Churchill, which I would highly recommend. This is the Taylor Branch series on Martin Luther King, also incredible. In the acknowledgments of the last book in the King series, Taylor Branch talks about how his youngest son was born like the day he started the series. And then took a break from college to help him finish the last book.

That's crazy, man. It is so nuts. Those are really like life's work.

They are. And it's not just that every sentence is perfect, but like, we don't see that. If you think about the iceberg, we don't see the research, the interviews, right? The on, like, location observing that went into forming one of those, those sentences. So yeah, like, there's definitely people who they're there's a reason they only do 2 or 3 things in their lifetime. Um, and then there's everybody else and chances are like you're everybody else. Uh, and so, uh, there's that. And then as far as the YouTube videos go, I do a couple different ones. Like, uh, one, the, I think the easiest YouTube videos we do are like compilations of like reels or Instagram clips that I do. So there's not a lot of script there. It's just the intro. It's like piecing together sort of meditations on a larger idea. But if it is a, like, you know, how to read Marcus Aurelius, how to read Seneca, or, you know, let me tell you the biography of this Stoic, or I have one coming out next week that's about the relationship between Marcus Aurelius and Antoninus Pius, his stepfather. That's a combination between like having somebody give me an outline And then me usually drawing on something that I wrote somewhere else. So for me, the writing, particularly of the books, is what generates the vast majority of the content. And then I have people who help me just, just in the way that I don't do the Spanish edition of my books. I have people who help translate what I've done into different mediums.

Are you using Google Docs?

Yeah, for them, for the most part. Yeah.

And how big is the team?

Uh, like 10 people now, probably. That includes, that includes the bookstore.

And also, does it include Daily Stoic and, uh, uh, Daily Dad?

Yeah. Yeah. I'm saying that I probably have 10 employees, maybe, maybe 11 or 12, but, but less than 15.

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I was messaging you the other day because someone was like, hey, you should start a book club to me. And I'm like, well, I read a lot, but like, you Ryan should really start it, like someone like that. And I looked a while ago, I looked in the book of the month business, the book of— it's called Book of the Month and it's like a company that's been around for like 50, 60, maybe even 100 years. It's been around for a long time and it's traded hands a ton. I think right now, last I heard, they're in the $70 million range of revenue, which is a big business, but I don't know if it's growing and I don't know if that makes a profit. I don't know what the situation is. But have you looked into these book of the month businesses? I think Reese Witherspoon had one too that I think was profitable.

Yeah, there's a, there's a couple different ones. There's another company called Literati, uh, Book of the Month. The Book of the Month concept definitely goes back, uh, quite a bit. And that used to be like a way that you would guarantee a book's success would be if you were selected to one of those clubs, cuz they might buy 100,000 copies or something. Um, there's, and then there's, uh, what is it called? The Next Big Idea Book Club, uh, which I think Malcolm Gladwell is an investor in. There's, there's a, there's a handful of them. Um, the problem with the business is, first off, not that many people read, right? Uh, unfortunately. Um, second, uh, the logistics of it are what is tough, right? So like, at the very best, you're going to be able to get those books from— like, let's say you're doing physical, right? At the very, very best, you're going to be able to get those books at 50% off from the publisher. So if you start to get into, uh, you know, like it, it drives the subscription. Like already your subscription is more than Netflix, which gets you unlimited of the best, most entertaining content in the world. Right. So the, the really tough part is getting to a place where you can move a lot of books and the revenue is high. So I started this newsletter like 15 years ago where I just recommend books.

Uh, when you have like 250,000 people now on it, something like that.

Yeah. And, and I just prefer to like, look, if you want to buy the book from my bookstore, I make a little bit of money doing that. If you buy it from Amazon, I get the commission, but I'd much rather just have that list and that audience than try to monetize a book club itself because the bundle of including the book, plus fulfilling the book, plus customer service and all that other stuff, it— I think, I think it's just hard to make the business itself work.

How much revenue can you make on one cent from, from the Reading List newsletter?

I don't know. I don't know.

I actually— $10,000 or $20,000 maybe.

Yeah, that would be, that would be a lot. Uh, because the, the other thing that I found is that the people who read the most, uh, who like real, like, like the kind, or at least the kind of readers that I attract are like, I don't wanna say they're lone wolves, but they're more like, uh, like, I don't know about you, but like the way I read is I just have at all times a long list of like books I'm going to get around to reading. I'm not like, oh, you're reading this book right now. I have space for you in my life. So like, like if I think about the impact that the list has had as far as moving copies for books, it's not like, oh, we sold this many copies of this book this month. It's more over a time. Although I did invest in this company. Do you know the company Vinyl Me?

I think I introduced you to them. Matt Fiedler, the founder, is my, was my high school.

Yeah.

Who's my, or my, my very, very, very close college friend and for for those listening, Vinyl Me Please is awesome. I don't know how many— I don't remember how many people they have, 20,000, 30,000 subscribers, and they send out a record, a vinyl, a piece of vinyl. And I remember he was, uh, like complaining to me. He was like, man, the, the, like, we— whenever someone gets selected for our vinyl, uh, like when we pick an album, it becomes the best-selling vinyl in the country because we're the biggest. But, but now they're not counting it anymore.

And, uh, right, it's the same thing we were talking about with the bestseller list. They, they would be the number one vinyl album in the country each month But, but they just get skunked from the Billboard charts.

Yeah. And I haven't asked Matt about the business lately, but it's been around for 10 years now and it seems to be doing good.

I, and I, but I think that's, that's a different experience. Right. And so I, I'm one of, I was, I guess I'm an advisor. So I got some early shares in Vinyl Me when it came out. So, and that's been a surprisingly big business. Like I, I, when I see the numbers, I'm always like, whoa, that's bigger than I would have guessed. Right. You wouldn't. You'd think like, oh, maybe 1,000 people a month, not 20,000 people a month.

Yeah, it's a lot of people.

But, but I think in music is people consume more music than they do books.

Right. And you can do it over and over again with a bunch of people.

It's a passive experience. And the, the art of discovery is different, right? Like you want to be suggested random things on a regular basis. And I think with a book, like, people have so little room to read in their lives that I don't know. I just, I, I, I like the idea of the business and it would be amazing to make it work. I have struggled to actually see it work. And I think, uh, there's probably just ultimately better ways to monetize that attention than, uh, than, than a list of subscribers you have to service each month for a specific kind of book.

You said something earlier about like you get access to all these amazing people and I follow you on Instagram and I've talked to you a bit and I follow your content and you are hanging out with like all these athletes, you're hanging out with billionaires and business people and celebrities and all these interesting people. Who are some of the people who you've met where you said, I want to emulate this particular attribute or the way that they've done this, this and this I admire so much, or this person is just wildly impressive. Who do you admire or, uh, of all the people you've met?

Ooh, that's a good question. Um, you know, I actually talk about this in the, in the end of, uh, of Discipline, uh, as I was sort of struggling with the book kind of early in the process. Like one, I was just fucking tired because I've done a lot of books in a very short amount of time. And like the idea, it just, I don't know, it just wasn't gelling. And, um, I had lunch with, uh, with Manu Ginobili, uh, who just got inducted in the Hall of Fame, uh, this month. and we were having lunch at the bookstore. He'd come out and we were hanging out and it just sort of struck me like this dude has 4 rings, like he has 4 championship rings and he has 2 gold medals, and is a Hall of Famer. And he was like, I don't want to say he's a regular person because that sounds like, that almost minimizes it. But the point is, when you think about someone who has 4 rings, I think you think more of like a Jordan character who is fundamentally out of balance, right? Like, so there's no disputing Jordan is— Jordan is like one of the greats, if not the greatest, like, basketball player, maybe athlete as a, as a whole, right? Um, but, but we tend to think that, that to be that good requires fundamentally some fundamental trade-offs about what kind of person you are and what your day-to-day life looks like. Tom Brady comes back to football. He can't walk away, and it may well cost him his marriage. And people see that and they go, "That's what it takes." I'm not sure that that is what it takes. That might be what it took in that specific scenario, but I the more I meet really successful people, I become less impressed by like how much money they made or like, you know, whether they have the most rings or the second most rings or whatever it is. And I go like, is this person like a good parent? Do they seem like they live in reality? You know, are— or are they like, are they actually able to wake up and enjoy like what they have today? Or is it like They're traveling here and there and they're just always doing stuff, right? I think like to me, what the, the journey that I've tried to go on inspired by people like that is I want to be world class at what I do and, and like be somewhat of a normal person. Like who else? It's almost easier to be great than it is to be good. If that makes sense.

Yeah, that's awesome. Who, who, who else have you, uh, who have you met? So, uh, you know, him and Chris Bosh are interesting. I've read, I listened to a bunch of content that you made with those guys. I felt the same way about Chris Bosh when I was listening to him. I'm like, oh man, this dude's like kinda, yeah, maybe normal's insulting, but like, that's what I was like. You're, uh, I'm never gonna be 7 feet tall, but like, you know, like your mentality is achievable. You know what I mean?

It's kind of funny as I do feel the same way about Chris and his wife and my wife are friends. But like every once in a while I'll mention one, one of them to the other and then I forget that they— Chris said something to me actually when I had him on the Daily Stoic podcast. He's like, you know, he's elbowed me in the face like a lot. Like, like it was like realizing like, like their best and worst moments came like the, the moment in both of their careers came at each other's expense, right? Like, like, uh, Manu goes up for a rebound that, that Chris gets, that Chris tips back to Ray Allen, who makes a 3-pointer to win, to basically win the series, right? Like, it is also weird to think like, yeah, here are these like kind of two people that I admire, and then they're on like a— their careers were like on a collision course with each other.

Are they buddies now?

I don't think so. No, I don't think so. Even though they, like, they live not far from each other, right? One's in San Antonio, one's in Austin. And I, I do not think that they, uh, see each other socially. That it might take some time, like maybe, maybe in 20 years, uh, the, that rivalry fades away.

Is there anyone else who you've met and you're like, man, the way that you're pulling this off or the way that you're playing life, I just admire so much?

Well, you know, it was, I had a weird one, uh, a couple weeks ago. I, I, um, I don't wanna say who it is. Uh, I, it not cuz I, it, I feel weird, uh, dropping the name. But anyways, let's just say, uh, I met this musician and, uh, he'd read the books and he reached out to me through someone we know and he was like, hey, you know, next time you're in New York, uh, you should come see me or let me know. I'd love to have dinner with you. So I was like, hey, I'm actually gonna be in New York like next week. And he is like, oh, all right. My assistant will like send you the details. And, um, the details were, uh, like go to this helipad. And then the helicopter took me and his son and our mutual friend to their house in the Hamptons where we had dinner, and then it flew us back to Manhattan after dinner. What? Yeah, it was fucking nuts. It was super nuts. But like talking to this person, he was like— I was like, so what's going on with you? He's like, well, you know, my youngest just went away to college, so we're empty nesters. Like, we're going to spend an extra couple of weeks here in the Hamptons. And it was like, um, again, I think at the end of your life and when you reflect on whether you were successful or not, you're going to think like, what is— do my kids want to spend time with me or not? Like, am I— what am I on my fourth marriage or am I on my first marriage? And he's, he's been— he's still with his high school sweetheart, right? Despite selling 100 million albums in between meeting and like the day that I was there. He's— he has a business that he founded with his son. Like, I, I like— to me, when I see stuff like that, I'm like, okay, this is fundamentally not normal in that like we just flew on a helicopter to have dinner and that was like, you know, like a wave of the hand for you. But that fundamentally you still worked very hard to remain rooted in some semblance of normalcy where your kids are not monsters and, uh, you're, you like spending time together.

You, uh, one of my favorite books is Conspiracy, which is, uh, Nick Denton, I believe. Is that his name? Nick Denton?

Yeah.

Yeah. Nick Denton, the founder of Gawker and Peter Thiel. And there's just so many moments in that book where I've been like, oh my God, I cannot believe that that's true. And basically like the fact that, like, Peter Thiel plotted and had people on staff for, like, some amount of years, 5 or 10 years, like a long time, in order to, like, hey, when you see Gawker screw up, you tell me and we're going to pounce and we're going to sue them because they outed me out as being gay. Or you also told another story about how Peter Thiel had a Mercedes, a black Mercedes everywhere he went that was just ready to roll in case anything bad happened. And I don't know if this was in the book or if I'm making this up, but I'm almost positive there was, like, a plane to New Zealand that like you, he knew about or something like that. Is that true or am I making that up?

The Mercedes thing is in the book. The New Zealand plane thing, that sounds true, but I think his New Zealand citizenship came after I finished the book.

Yeah, just like all this crazy stuff.

What— sure.

What was it like getting to know that guy? I mean, he's one of those guys where, like, I actually don't think there is— I don't know him, but where there actually is no balance and he is just really quirky.

Well, I think, uh, it's, it's both, it's both very understandable and then very inexplicable, right? Like, if you had made billions of dollars and you were very powerful, I don't think you would like to be picked on, right? Like, I think people were like, why would he do this? And it's like, would you? This, this bully came along and humiliated him in his eyes. Like, I, I don't like, not being a gay man, I can't really fully understand what the reaction would be to being outed. And a number of people that I, that I interviewed for the book who were gay, like, they didn't even understand. So, like, let's just, let's just stipulate that his explanation of his experience was that this was humiliating and he found it to be very frustrating. Uh, I think when you're at that level, one of the feelings that you don't sit— that doesn't sit well with you is impotence, right? Like, so when people were like, Peter, there's just nothing you can do about it, he was like, then what the fuck is the point of everything I've done, right? And so, so in that sense, I think it's very understandable. I think that the problem is if you're the kind of person who is like, I'm gonna spend 10 years, uh, chasing down this media outlet when everyone is telling me not to do that, you're also the kind of person who can get sucked into other things that I think are going to pay off less well, whether it's backing JD Vance or Blake Masters or some of the other political bets that he's made. Um, you know, I do, I find the sort of anger and the resentment of what it seems to be driving that I've, I've, I have trouble, I have trouble understanding it, dude.

I don't have trouble understanding that. I get so, I don't, it just, it comes from, at least for me, like I would have done the same thing if I, if like, if you're, if you have all that money and power and someone wrongs you, I want to, I have that same mentality where I'm like, I want to crush them. Typically I've got my wife saying like, dude, chill, you're— this isn't worth it. And so like, I listened to her, but if I didn't have her, I'd be like, no, no, no, we're going to— let's destroy them. And it comes from—

I get that, that I understand. That's the Count of Monte Cristo. That's the oldest revenge story of, uh, of, of history. I'm saying more the other thing, like the problem is, uh, when you sort of start to feel like you can bend the world to your will. That you can do anything and everything, I think you get sucked down other avenues. And I think some of the political bets he's made, uh, you know, even, even Trump himself, like, the fact that it worked, uh, doesn't mean that it made rational sense.

But how do you not feel like that? I mean, with my very, very small amount of internet fame and my mediocre to small financial success, I'm like, oh, like I just, I bent the, you know, in, in a, I'm a big fish sometimes in a small pond and I'm a small fish in a big pond, but I'll be like, oh, sick. I just, I bent the, that's, I say it all the time. I bent the world to my reality. Like I just made my, my true, the thing I wanted to be true. I made it true. And that is incredibly intoxicating. I think that there's lots of ways to do that. There's a lot. If you wrote a book and millions of people read it, there's a way to do that. If you become powerful in politics. There's a way to do that. If you— the easiest and most practical way for most people is if you learn how to make money on your own, then you're like, oh, like, whatever I want, I turn into reality. I have a joke, I call myself a manifest cowboy. Like, I just make— I make the things that I want to— the things I think of. I am not a business person. I am an expert at making things that I think of be real. And even at a small scale, I get intoxicated like that. And by— I get intoxicated by it. Do you not?

I, I have seen up close— I, I feel like very lucky that up close and personal, multiple times, particularly early on in my career, I saw people who, who had the ability to do that, um, also destroy themselves, right? So like, I, I direct— Dov Charney was my direct boss, right? Like, he would call me 5 times a day, and I watched a guy who built a multi-billion dollar company that made 50 million t-shirts a year, uh, you know, Start something. I mean, I didn't see him start it, but I, let, let, let's put it this way. The, the, the arc of the entrepreneurial journey, the, the beauty and the danger of it is that you have an idea for something that is insane, right? Like people are like, that will never work. Here's all the reasons you will fail. Do not do that. You will regret it. Right. And then you do it and it works. Right. That's, that's the definition of what entrepreneurship does. If everyone knew how to do it, or if it was easy, it would have already been done. You were able to create something from nothing, you know, that violates everyone else's conception of what's possible. The dangerous thing you take from that is you now, as you said, see yourself as a person who does that, and you see people who tell you that you can't do it or shouldn't do it or criticize you for doing it you see them as the enemy, right? So when Doug Charny is like, I'm going to start a made-in-USA, sweatshop-free fashion company that doesn't print its brand on things, doesn't use professional models, and owns all of its own stores, and I'm gonna sell all those products for an enormous premium. Like, that's, that's fucking nuts, right? Like, no part of that should work. So then he does it, and then people are like, Okay, you did it, but you should really have seasoned operators around you. You know, you really shouldn't overexpand too quickly. You know, by the way, it's not proper to have sexual relations with your employees, right? All these things that they told him, he was like, fuck you, who are you to tell me? Look at what I've done, right? And so he crashes and burns as a result of this. Exactly what you said, like, I'm a manifest cowboy. The rules don't apply to me. I can bend reality to my will. Like, do you ever, you ever heard that expression, the political expression about the reality-based community? Do you know that? No. What's that? So, so as, as George, as George Bush was contemplating the invasion of Iraq, I think it was Karl Rove, but I, one of, one of the officials in the Bush administration, you know, is responding to all the people who are like, it's going to be an enormous quagmire. You're not going to get the— like, right now you have no international support, blah, blah, blah. It's going to cost this, you know. And they go, look, he's like, there's two kinds of people. He's like, there's the people who live in the reality-based community and then the people who believe in America. It basically says who believe in American exceptionalism, who believes that America creates its own reality, bends the rules, the order of the world to its will. And so they believed as they went into Iraq that, yeah, it was a bad idea for all these reasons, but that could be changed through force of will and confidence and firepower, etc.

But they're not always wrong. But it's not true. Maybe in that case, but like that, that feeling is cousins to— yeah, cousins to the other— to it working. Do you know what I mean? Where's Chernobyl from?

Argentina.

Like, this Argentinian dude is going to come and, like, be the boss and, like, kill it. And, like, you know what I mean? Like, that— they're, they're cousins.

Yes, but, but here's the thing. Like, when you look at Manu's story, he did not wake up one day in Argentina and go, I will be a Hall of Fame NBA player, right? He makes his way— like, almost all those journeys are much smaller and humbler than that, right? He makes the Argentinian team. He's pretty good. He gets, you know, he gets an opportunity to play in Europe where he plays. He gets drafted like very late, a total surprise. He had not actually even entered the draft. He was just drafted by the Spurs who let him play in Europe for like 3 years before he comes over. Almost nobody believed in him. I mean, he knew what he, he knew he was good and he was confident in his abilities, but there was not these delusions of grandeur. He was not Kanye West going around saying, I'm Steve Jobs, right? Like, This was— he was like, uh, in the Churchill book they talk about this. Churchill did not— at the— at when, when Britain is standing alone, uh, he does not— in— he does not know for certain that he will be able to bring America into the war. And that year, like, what, what, what Churchill does is he buys some time, right? Like, all of these things start small and they build there when, when the person has this vision that they can clearly articulate, that they know to be like that. To me, that leads to disaster more often than the prophecy comes true.

Dude, that's crazy fascinating to me. I got to keep thinking about that. But another thing that you're associated with that I find, like, equally impressive even though it's much smaller now to all the other things that you've done, is the ghost town Cerro Gordo, which I'm a very, very, very small investor in. But the reason why it's awesome is— no, you're not a small investor. You're the guy.

The reason why is the guy.

Well, you're, you're, you're— I view you, Brent, and Nathan, Nathan Berry, as like, you know, the guys. But so basically, like in 2015 or '14, you guys like you know, got some money together and you bought this town that went viral because it was like, you can buy a whole town for $1.3 million, a ghost town. And you guys bought it and it was like doing okay, whatever. And then the pandemic hit and Brent spin-ups this YouTube channel and it felt like in a matter of 6 months it got a million subscribers. And I remember being in my apartment in San Francisco, miserable that I'm trapped in this place. And I see these videos of him and it's like the— it felt like it got me through the first like 12 months of the pandemic watching those videos. Like, I felt so much better watching these like 20 or 30-minute videos of this charming, cute dude named Brent, like saying like, hey, so here's this old mine that I just found in my town. Let's just like, you know, walk 100 feet into this mine and let's just see what we find. And it's— when you think of a mine, you think of like a cave. And this was like a, like a crawl space. And he just like is going deep in these places. And that was amazing. What a What's your feeling on how everything's going with that? And like, what's the plan?

Well, I mean, 100 feet in a mine. One of the mines is 900 feet straight down that he regularly goes in. It's fucking insane. It's crazy.

His videos are so good. Did you advise him or you guys were partners on something? Does he— did he get the content bug from you? Are you advising him? How is this shit so good?

It's an amazing story. It actually goes to what we were just talking about, like the idea in it. As an outsider or in retrospect, it feels like guy makes brilliant investment, buys town, turns it into a YouTube channel, makes these amazing videos in the—

and it seems obvious now—

blows up. Yeah, but that's not how it went at all, right? Like, first off, by the way, what's the name of the channel? Ghost Town Living. Okay. When he first told me about it, I was like, dude, that's a horrible idea. I'm not interested at all. Right. Like, I came in at a very small level at first because I didn't think it was a good idea. But Brent's idea was buy this place, build a hotel on the site, and make it some sort of like luxury resort thing that, that they failed to do for like 2 years, maybe even 3 years. He had no intention of living up there. It was losing money hand over fist. Right. Like he—

how many acres is it?

It's 300 acres, but it backs up to like thousands of acres of government land. So it's—

and it's like in the mountains, unlimited land, like 4 hours outside of LA.

It's— yeah, it's about 3.5 hours from LA. It looks down on Death Valley at about 8,500 feet. It was once the largest silver mine in the United States.

But there's like no water and electricity, right?

There is. I was just up there. He— like, I took a nice warm shower. There's water now.

Oh, but there wasn't. I guess there was not.

I mean, historically there were some springs and then those dried up and I mean, it has always been a battle of the elements, but it's funny that you, you, you bring up how you liked the videos during the pandemic. My 4-year-old fell in love with the videos during the pandemic, and that's part of the reason I ended up investing more money in it was that my son is obsessed. Uh, like he knows he had trouble. So Brent started as my intern like 12 or 13 years ago, I think. Um, and my son has met, I mean, has known Brent his whole life. And he's got so enthralled with the videos that he had trouble because it was the pandemic. We couldn't see him. He had trouble like conceiving of the fact that this was a real person that he knew that this was different than the YouTube channels of other people that he watches that he doesn't know.

And so it's been like, he's so charming in these videos and he's so endearing and like, I don't know, I've not really hung out with him. I've only chatted with him a couple of times. It seems like he just kind of turned on this charm and charisma and it was like intoxicating.

He's always been like a behind the scenes person. And I think that's what's so interesting is like, yeah, he didn't just randomly start a YouTube channel one day. Like he started the Daily Stoic YouTube channel and he started the Daily Stoic podcast. Like he, he was the one who, who built out the systems or created the universes for me. Um, and that, that I am obviously the face of, but he was the one who was like, here, I think we should do this. And he's the one that figured, like, you know, we probably had 100,000 YouTube subscribers when he went to Cerro Gordo. So he had experience that he'd learned on the job, so to speak, uh, working with me. Um, and then the, the funny thing is, uh, we had shot some videos for Daily Stoic, like the first week of March, 2020, or maybe the last week of February. Um, and he had taken a camera home to like upload some stuff. And so when he went to Cerro Gordo, he just took my camera or our camera like that. Cerro Gordo was started with equipment that he had got for Daily Stoic and then used skills that he had developed, uh, with Daily Stoic that ultimately blew up into this thing that I don't think he— definitely not I would've predicted, but like people often underestimate how long you have to spend developing like a baseline of skills before, you know, sort of the man meets the moment, so to speak.

Dude, I read that in Mastery. Mastery changed my life. I remember like exactly where I was when I read it and I was like, oh, this, this is called apprenticeship. Like, and it totally changed Mastery. You know, I got turned on to you because I was, or maybe I don't remember if you got me onto Greene or him to you, but I remember reading Mastery and that was like a life-changing book. Because it talked, talked, talked about that.

But Sarah Gordon, I think about that, like, do you ever think about the fact that The Hustle and this podcast could actually be the apprenticeship for like a company you start in your 50s? That's—

oh, it's going to be. It's going to be. And people like, you know, all right, so The Hustle, we sold for, let's say, tens of millions of dollars, which is like, I think by most people, if you do— I think I was 31, 30 when we sold it, which is so like, that's That's 6— that I would say it's objectively successful, but compared to others, like, it's nothing, right? Like, sure, compared to the company that bought us, it's nothing. Yeah, you know, they bought us. But, uh, and so a lot of people were like, well, you know, like, you guys only did that in 4 years. I'm like, yeah, we did it in 4 years. I also spent 4 years before that though, uh, studying writing and like blogging and reading and like being a student. And I learned a skill, which my skill was copywriting. And that skill led me to this other thing, which led me to this other thing, which led me to this other thing. And I often tell people, I'm like, everyone says overnight successes aren't true. And I'm like, well, in a sense, actually they can be like, you could be a Mark Manson or something and like write a book and like it get really big, really fast. But more likely than not, that could happen. Like hitting the lottery is real. Like look at Instagram. But learning the skill for 5 or 10 years in advance is often necessary.

Yeah. To give Mark credit though, Mark doesn't hit the lottery. I mean, Mark was an online copywriter and marketer and had a platform for a decade before he writes a book, right? Like, right.

But what I mean is like the step functions in growth are real.

Yeah.

You know, like it could be like it's going okay, it's going okay, it's going okay. And then a matter of like a month or 3 months, it's like, boom, something just changed. Like that is real. And I think people actually don't like acknowledging that because the story of like slow and steady is preferred cuz that like there's more character to that. But like step functions exist, but you have to work a certain amount of time typically in order to get that step function. That's what I mean.

No, I think about Michael Lewis in that regard. Like Michael Lewis is, is a fantastic writer. He's been a great writer for 40 years. He wrote Liar's Poker, which is about finance. He wrote The Blind Side. You know, he wrote a number of these books that were, that were big. And he was, he was a leading nonfiction author. And then 2008 happens and it's the most inexplicable but widespread financial event of, you know, since the Great Depression. And he is uniquely suited to write The Big Short, which was his big transformative You know, uh, huge book like Moneyball, The Blind Side, the other movies that come out, I believe they come out after The Big Short. Like Michael Lewis today looks like he's always been huge, but you don't realize his career was sort of like this and then like this, right? Like what? Like I, I, I think about that. I, I, I'm very proud of all of the books that I've written and I, I continue to write them and work on it every day. But I all, I don't wanna say I hold out hope, but I, I feel like there's some part of me that thinks all of this is training for like the book at the moment. Maybe it happens, maybe it doesn't. Maybe it's the moment, but the book only sells 10 copies. But like, I do feel like it's building towards whatever I'm meant to do.

Are you not satisfied with your career?

No, I'm very, I'm very satisfied. Like more, I was just writing about this in my journal this morning. Like when I look at the sales number of this book, This isn't just like what I dreamed of. This is like 10x what I even conceived of as being possible. I'm just saying, like, I, I, I want what I'm working on to set me up for like something truly challenging, so challenging that I— or perfect for my skills and what I— my worldview that I can't even think of it yet.

Dude, consistently I've said, once I hit this wealth number, I likely won't want any more. And then I always do. Once I lift this much weight or do this type of athletic feat that I've been really working hard towards, like, I'll be happy. And then I get there, I'm like, but we could go a little, we could do a little more. So like, uh, I, it's all, I think that's just unilaterally true with at least people who are driven enough to achieve anything interesting. Like, it's just like it, I've just settled with it's just never enough. I mean, that's okay.

I've never heard of someone getting to the number, like, like, like actually getting the number because the goalposts always move. So when I hear people say it, there's a number, like when I, when I talked to an author and they're like, my goal is to sell a million copies or whatever. I go like, I don't have goals. Like, why would he, why would you even put a ceiling on it? Right? Like what you should just try to sell as many copies as it's capable of selling.

Do you have, um, other than like be a good dad and be a good person and all this stuff, do you have any professional goals for the next 5, 10, or 20 years where you say like, this is what I want? Or any people who you say, I want to be, I want my career to be similar to this type of person.

Yeah. I mean, so like I sold this 4-book series, so to do 4, like 4 interlocking interrelated books in ostensibly 4 years, that, that's the, that's what it It could change, but that is the mountain that I'm climbing right now because it was unlike the mountains that I'd done before. I don't have a certain number of books that I'm trying to write or a certain number of copies that I'm trying to write, but I do— I've never written one of those biographies that we were talking about, and there's some part of me that thinks about maybe doing that at some point, um, and doing it for one place.

Anyone in particular?

I do have a person, but I don't want to say because, uh, someone might steal it. But, but I, but I, but I, but I have thought about doing a big, a big book like that. And I, there's a part of me that thinks being able to do it and not, not care, like financially, like if it takes 5 years or takes 10 years, like there's a part of me that thinks about that. And I, so I have a couple ideas like that where I'm like, that would be a cool thing to do. But like, I have the weird sensation, I'm sure you have this too, of like, of like very much feeling like I'm playing with house money. And that's both really fun. And then it's also a little, it's like a little unmooring because you're like, shit, I thought I was running with everyone else. And then now I'm just like by myself. Am I going fast enough? Am I going too fast? You know, did I take too much risk somewhere?

Dude, and you don't want to lose it. It's like, that's a weird feeling where you're like, well, I have what I wanted. I thought that I'd be willing to like spend this much to invest on my idea. And then it's like, but I don't want to lose this. And that also exists.

Well, you think that being successful will make you more courageous because you are more secure, but it actually, the rational response to to having a lot is to become more risk-averse because you know how hard it was to get it. And so there's a tension there. You know, how do you, how do you continue to push yourself without being reckless? And how do you, uh, protect what you've built without being complacent?

Wait, but you, you just said something that reminded me of the, the fisherman story you started off with, which was you said like, I wanna write this biography and I hope I'll be at a place where like financially it doesn't matter. Do you, you don't feel that you're there already?

No, no, no. I mean, I feel like I'm there. I just have to get through these two books. I've already— like, I'm already creatively committed to an idea. It's like, like a director. It's like, hey, I've already attached to these two movies or three movies. Then like, once, once my plate is cleared and I'm not trying to, I'm not trying to put it off into the future. I don't feel rushed to do it. I'm just saying like when, when I have a clear plate or open road in front of me, I think that's probably something I might fuck around with.

Any topics that we didn't cover that you think need to be covered?

Um, you know what, actually, yeah. Uh, I mentioned to you in text, you were like, well, can we talk about like how much money your books have made?

I, I, I, that's not what I said was I go, uh, how much money have you made? How big is your dick? What's your social security? Yeah.

No, it's, it's funny, like on my first books, uh, like obviously books as a market are less interesting to people than like the movie business, but like, um, uh, whenever I would sell a book, like the, your agent or publisher, they're like, should we announce this deal? Like there's trades, right? And sometimes like my first book got a ton of publicity because I was like a kid who came out of nowhere and sold a book for a bunch of money. I was always, I was like, I want a press release. Like I want to put this out. And then probably starting, I think it was with Stillness. It might've been after it, definitely with this series that I realized that there was no advantage to doing that. That, um, when you start talking about what something is sold for or how, like I've two things I thought, okay, so I sold this 4-book deal and it was a, it was a very large deal, at least for me. And I had two thoughts. I said, one, telling people how much money I made from it, it makes you a target, makes you weird. You know, it, it, it could, it could somehow be seen as selling out or something. But then the other part, I, I thought, I don't want people to— this is an idea that's gonna take me 4+ years to get to the end of. Why would I want to give people who might be writing in the same niche like a heads up about what I'm doing. And so I don't think I've announced, you know, when I did a podcast deal, when I've sold other projects, like I see no benefit to putting out specific figures. I only see, uh, downsides to that. I don't know.

Would you do a podcast deal with— no, I, I do agree with that at first. You know, it's like that song, um, uh, if Dammit Feels Good to Be a Gangster, they said real gang, real gangsters don't flex nuts because they know they got them.

And yeah, and that's how you, you make the police come after you, right? Like, yeah.

But I used to feel that way where I'm like, yeah, like when I, I mean, I'm still insecure, but when I was even more insecure, I would be like, yeah, I need to, I'm going to rub this into my high school friend's face.

Yeah.

And then now I'm like, I don't want to get sued. I don't want to be a target. I don't want people to pretend because I get all these fake people on Twitter or Instagram pretending to be me or like people like threaten to sue you when you're not wrong at all. Like now I'm like, oh, I don't want any of that nonsense.

Yeah, I did a, I did a podcast deal with, uh, with Amazon Wondery, uh, like maybe 3 months ago.

Um, how big's the pod now? Or do you measure it in podcast downloads or YouTube views?

Uh, YouTube is, it isn't, wasn't included in the deal. So that's separate. Um, but, uh, podcast is, is fantastic. Like I think we, we crossed 100 million downloads.

That's crazy. Yeah.

Do, should do what we're getting. Close to being able to do that annually. Like not quite, but like that to me, that's, that's where the numbers are at.

We're at, um, our monthly downloads on the podcast range between 1.5 and 2 or 1.3 and 2 million. And then the pod, the, and then the YouTube episode views are another 1 or 2 million. So we're in the range of 2 to 5 on any given month. And, uh, our next target, I'm like, how do we get to that 5 to 10? Sounds like you're there, dude.

I think YouTube is the— it's weird to say like YouTube's the big thing because it's been around for 15 years and it's already huge. But like, uh, the growth I'm seeing on YouTube stuff, especially now, even with Shorts, it's crazy, dude.

People our age and older, they're like, what, YouTube? I'm like, no, dog, YouTube's TV. Like, it's like, you know, YouTube is where it's at and it still has so much room.

You—

because I only watch YouTube as my TV. Yeah, it's the best. Well, dude, you're awesome, man. I, I asked you like who you admire and who you want to steal from. And I have like a short list of maybe 3 or 5 people. And you are on that list where I just think like we're like, you know, I'm a family guy like you. I don't have kids yet, but like I see you raise your family. I see you with your wife. I see like, you know, I also bought a kind of like a farm inspired by you. I live in Austin most of the year, like there's so many things that you've done where I think this guy's nailing it and I want to steal little bits and pieces of how he's doing and how he's living life. And I admire your confidence, your drive. I mean, I'm on, I'm on the Ryan Holiday train. I've been on it since, since the first book. So media, media confessions.

Well, we got to hang— we got to hang out when you're back, man.

You and I are almost a little bit similar where we have our toes in like the New York world and in the L.A. world. But, you know, I lived in Tennessee for a long time. I live in Texas just like you. I like doing, I like the bougie shit and I like the redneck shit, man. I like it all. Oh, so, uh, I'll, I'll holler at you when I get back and, uh, I appreciate you coming on, man. This is awesome.

I wanna see the farm.

Uh, and, uh, say the book name again.

Oh, Discipline is Destiny: The Power of Self-Control. As part of the Stoic Virtue Series. The first one is, uh, Courage is Calling.

Where do you make the most money? Where people buy it?

Ooh, if you buy it from, from dailystoic.com or my bookstore, The Painted Porch.

Awesome. Well, I appreciate you, man. This is awesome. Thank you.

Dude, thanks.