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

1. 0:00 – 3:28

   Intro

   1. SPSam Parr0:00

      And then I googled, like, Mark Manson house, 'cause that's always, like, the tell on, like, is someone, like, crushing it. Because it's, it's, you can't really, like... It's hard to get a mortgage for a $15 million house-

   2. RHRyan Holiday0:08

      Yeah

   3. SPSam Parr0:08

      ... 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, he..." Like, I thought book, the book business was a bad business. He must have crushed it. He must be making millions. [upbeat music] My man, Ryan Holiday.

   4. RHRyan Holiday0:30

      How are you?

   5. SPSam Parr0:30

      What's going on? Nice to, nice to talk to you.

   6. RHRyan Holiday0:33

      It's good to talk to you, too.

   7. SPSam Parr0:34

      Um, so you, you, you asked to come here, and I'll just... 'Cause I just wanna get it out of the way. I wanna give you the love. You asked to come on here because, A, we're homies and I love you.

   8. RHRyan Holiday0:42

      Yeah.

   9. SPSam Parr0:42

      And, and also because, B, you have a book coming out.

   10. RHRyan Holiday0:45

       Yes.

   11. SPSam Parr0:45

       What's it called?

   12. RHRyan Holiday0:47

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

   13. SPSam Parr0:53

       Oh, and how's it going so far?

   14. RHRyan Holiday0:55

       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, 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.

   15. SPSam Parr1:19

       What do you think this, the outcome of this one's gonna be?

   16. RHRyan Holiday1:23

       Um, will 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. Uh, all of which my publisher is very concerned about and I have decided that I don't care about at all anymore.

   17. SPSam Parr1:54

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

   18. RHRyan Holiday2:03

       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, 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-

   19. SPSam Parr3:26

       Does being bo-

   20. RHRyan Holiday3:27

       ... of writing a book is for people

2. 3:28 – 5:15

   Does the bestseller list still matter?

   1. RHRyan Holiday3:28

      to read it.

   2. SPSam Parr3:28

      Does being on that list... And when you say the bestseller list, are you meaning just the New York Time? Is that considered, like, the list? And does being on that-

   3. RHRyan Holiday3:35

      There's-

   4. SPSam Parr3:35

      ... help sales?

   5. RHRyan Holiday3:37

      There's, there's sort of three lists. There's New York Times, which you, you'd probably rank as number one, Wall Street Journal, which you'd probably rank as number two, and then USA Today. Those are the three, uh, what... You have to hit one of those three lists to be called a national bestseller. Those are the three national lists. Um, there i- 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.

   6. SPSam Parr4:16

      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's, like, a 20 or a $40 billion company, and they're referencing Mark Manson. And I'm like, "Oh, wow, that's, that must be a huge book, uh, in order for them to, like, discuss this in a-

   7. RHRyan Holiday4:50

      Sure

   8. SPSam Parr4:50

      ... six pages of 100-page document." And then I googled, like, Mark Manson house, 'cause that's always, like, the tell on, like, is someone, like, crushing it. Because it's, you can't really, like... It's hard to get a mortgage for a $15 million house-

   9. RHRyan Holiday5:01

      Yeah

   10. SPSam Parr5:01

       ... 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, he..." Like, I thought book, the book business was a bad business. He must have crushed it. He must be making millions.

3. 5:15 – 29:42

   Breaking down the #s of the publishing industry

   1. RHRyan Holiday5:15

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

   2. SPSam Parr5:36

      I think they're owned by, uh, a parent company. I forget what the parent company, though.

   3. RHRyan Holiday5:39

      They, they're owned by Bertelsmann or something like that. Uh-

   4. SPSam Parr5:41

      Yeah, yeah, yeah. That's right

   5. RHRyan Holiday5:42

      ... but, um, you know, what's, uh... Revenues. Their revenues are, I bet, uh, uh, four billion euro for, 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 seven or eight billion dollar 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. Now, a lot of those-

   6. SPSam Parr6:23

      And what do they cost, 20 bucks?

   7. RHRyan Holiday6:25

      Yeah, so, so if you think about, like, my books, I- I've sold five million copies. If you said 20, that's, that's $100 million in gross revenues right there, right?

   8. SPSam Parr6:34

      It's crazy.

   9. RHRyan Holiday6:34

      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, uh, that's, you know, cuts it in half. Uh, and then, you know, blah, blah, blah, blah, blah. It goes down. But, but there are ve- if you think about, uh, 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 JK 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, the different formats, whether it's audio or e-book or physical or hardcover, even hardcover and paperback is a big thing. Like, one of the... I bet Mark, for instance, and I, I know Mark and he's amazing, the distinction... The, the decision to put your book in paperback is actually a multimillion dollar decision for authors and, 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 this same contract, it's just this is what it is, is, uh, 15% on hardcover price. So, uh, a- 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 and a half percent. So my, my agent, very early, who was in publishing, he was like, he was like, uh, "I will never let your books go into paperback." Um, he's like, "You have to sell about as thir- you have to sell a third more books to make the same amount of money that you 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 you don't often think of.

   10. SPSam Parr8:52

       What about Audible and e-book?

   11. RHRyan Holiday8:54

       So Audible you make, uh... I, I think it's the same as i- I think Audible and e-book are 25% of list price. So you make... It, it's a higher royalty, but on a lower price point. Audiobooks are like 15 bucks or nine bucks, uh, for, for e-books a lot of times. Uh, so, so somewhere between two and three bucks a book you make across formats-

   12. SPSam Parr9:19

       So how much-

   13. RHRyan Holiday9:19

       ... if you're in hardcover or e-book

   14. SPSam Parr9:21

       How... And so you think Mark's book has sold 200... Is, I think, did you say 200 million in sales? So-

   15. RHRyan Holiday9:28

       No, no, 20. He's probably sold 20 million books.

   16. SPSam Parr9:30

       Uh, sorry, in gross revenue.

   17. RHRyan Holiday9:32

       Oh, uh, well, 20 million books times hardcover pri- or, you know, it, it, it... There's gonna 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, 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, uh, somebody sent me a copy of one of my books in, uh, 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, uh, copyright. They just do whatever they want." He's like, "You'll never see a penny from these books."

   18. SPSam Parr10:26

       [laughs]

   19. RHRyan Holiday10:26

       So the point is, like, if, uh, 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, uh, but you'll... You, you know, it's, you start to get into, uh, 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 gonna be overstating the cash they have on hand. [laughs]

   20. SPSam Parr10:57

       So, uh, 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. Uh, I mean, how many authors are doing that?

   21. RHRyan Holiday11:09

       Selling five million books? Uh, ver- very few. I mean, definitely there are 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. Uh, certainly not in, in, in, like, the modern world. So, you know, when I went to my publisher and I s- you know, uh, offered them a, an obscure book about ancient philosophy in 2011, 2012 for, for The Stoic b- uh, 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 three or four million copies.

   22. SPSam Parr11:50

       Do you think that your life has or will become... So we were talking about Tim Ferriss, and we're like w- you know, however much he's made on books, it probably pales in comparison. He's, uh, arguably, like, just guessing, maybe he's worth 150 to $250 million based off of his Shopify and Uber and seed investments, and who-

   23. RHRyan Holiday12:08

       Sure

   24. SPSam Parr12:08

       ... he probably has done so many more things that I don't even know about. Do you think that your business is gonna be a similar thing, where it's almost like the books are awesome, but they're gonna be tiny compared to the other, uh, revenue streams?

   25. RHRyan Holiday12:20

       I don't know. I don't, I don't do that many investments, but it is weird. Like, I, I, um, 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've had to sell a lot of books to get this same amount of money," and this amount of money was, you know, a lot less work. So I, 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, I do think it makes you a little disinterested in the economics of publishing, even though they are quite, they are [laughs] quite good.

   26. SPSam Parr13:09

       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, a lot of hard work." And I was like, "Yeah, I don't know why you'd write a book then when y- 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 in-

   27. RHRyan Holiday13:33

       It is-

   28. SPSam Parr13:33

       It seems almost impossible. [laughs]

   29. RHRyan Holiday13:35

       It is super weird though because, uh, like, a lot... Wealthy people read books, right? The, the, 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, uh, 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, uh, or a political book that sells reasonably well, you're gonna, you're gonna have some name recognition in an elite group. And so I've gotten to meet, like, a number of very successful businesspeople over the years, and, like, as a rule, they all wanna write books or all wanna 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' 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 s- started this company called School of Life. Uh, he was like, "I think I would do something like that." And I was just, uh, I just burst into laughter because, like-

   30. SPSam Parr15:25

       Just do it now
4. 29:42 – 36:20

   How big is your team?

   1. SPSam Parr29:42

      And how big's the team?

   2. RHRyan Holiday29:44

      Uh, like, 10 people now probably.

   3. SPSam Parr29:50

      And that includes-

   4. RHRyan Holiday29:51

      That includes, that includes the bookstore.

   5. SPSam Parr29:53

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

   6. RHRyan Holiday29:58

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

   7. SPSam Parr30:05

      Dude, that is crazy, man. The output is just awesome. I, I, I think that's amazing.

   8. SPSpeaker30:09

      [upbeat music] Our software's the worst. Have you heard of HubSpot? See, most CRMs are a cobbled-together mess, but HubSpot is easy to adopt and actually looks gorgeous. I think I love our new CRM. Our software is the best. HubSpot. Grow better.

   9. SPSam Parr30:27

      I was messaging you the other day because, um, 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... Uh, a while ago, I looked into book of the month bus- the book of the...

   10. RHRyan Holiday30:41

       Yeah.

   11. SPSam Parr30:41

       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-

   12. RHRyan Holiday30:46

       Yes

   13. SPSam Parr30:46

       ... 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.

   14. RHRyan Holiday30:52

       Mm-hmm.

   15. SPSam Parr30:53

       Um, which is a, 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 w- have you looked into these book of the month businesses? I think Re- Reese Witherspoon had one, too, that I think was profitable.

   16. RHRyan Holiday31:04

       Yeah, there's a, there's a couple different ones. There's another company called Literati. Uh, Book of the Month, th- 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, 'cause 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 gonna be able to get those books from ... Like let's say you're doing physical, right? At the very, very best, you're gonna 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, 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, I started this newsletter like 15 years ago where I just recommend books. Uh-

   17. SPSam Parr32:32

       What do you have, like 250,000 people now on it?

   18. RHRyan Holiday32:34

       Something like that, yeah. And, and I just prefer to like ... Look, if you wanna 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 at scale.

   19. SPSam Parr33:06

       How much revenue can you make on one send?

   20. RHRyan Holiday33:09

       Uh, from, from the reading list newsletter? I don't know. Um, I don't know. Uh, I actually-

   21. SPSam Parr33:15

       Probably 10 or 20 grand maybe or-

   22. RHRyan Holiday33:18

       Yeah, that, that would be, that would be a, a lot. Uh, because the, the other thing that I've found is that the people who read the most, uh, who like real, like, like the ki- 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?

   23. SPSam Parr34:05

       I think I introduced you to them. Matt Fiedler, the founder is my-

   24. RHRyan Holiday34:08

       Oh, you know him. Great

   25. SPSam Parr34:08

       ... he was my high school-

   26. RHRyan Holiday34:09

       Yeah

   27. SPSam Parr34:09

       ... he was my hi- or my c- my very, very, very close college friend. And for those listening, Vinyl Me Please is awesome. I don't know how many, I don't remember how many people they have, 20, 30,000 subscribers and they send out a record, a vinyl, of, a piece of vinyl. And I remember he was h- 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-"

   28. RHRyan Holiday34:34

       Yeah

   29. SPSam Parr34:34

       ... "But, but now they're not counting it anymore." And, uh-

   30. RHRyan Holiday34:36

       Same, it's ... Right. It's the same thing-
5. 36:20 – 47:34

   Who do you admire?

   1. SPSam Parr36:20

      people. Who are some of the people who you've met where you said, "I wanna emulate this particular attribute," or, "The way that they've done this, this, and this I admire so much," or, "This person's just wildly impressive." Who do you admire m- or, uh, of all the people you've met?

   2. RHRyan Holiday36:35

      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 'cause 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 Ginóbili, uh, who just got inducted in the Hall of Fame, uh, this month. Um, and we were, we were having lunch at the, at the bookstore. He, he'd come out and we were hanging out, and it just sort of struck me, like this dude has four rings. Like he has four championship rings, and he has two gold medals, uh, and is a Hall of Famer. And he was like, I, I don't wanna say he's a regular person, 'cause that sounds like, uh, uh, that almost minimizes it, but the point is, when you think about someone who has four 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, uh, Jordan is like one of the greats, if not the greatest, like basketball player, uh, maybe athlete as a, as a whole, right? Um, but, but we tend to think that, that to be that good requires, like, fundamentally, uh, some fundamental trade-offs about what kind of person you are and what your day-to-day life looks like. Like, um, Tom Brady, right? Uh, comes back to football. He can't walk away, and it may well cost him his marriage, right? And, and people see that and they go, "That's what it takes," right? Um, I'm not sure that that is what it takes. That might be, you know, what it took in that specific scenario. But like 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, um, "Is this person like a good parent? Do they seem like they live in reality?" You know? Um, are, 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? Um, I, I think, like to me, what the, the, the journey that I've tried to go on inspired by people like that is I wanna be world-class at what I do and s- and like be a somewhat of a normal person. Like-

   3. SPSam Parr39:14

      Who else?

   4. RHRyan Holiday39:14

      ... it, it's almost easier to be great than it is to be good, if that makes sense.

   5. SPSam Parr39:19

      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 n- yeah, maybe normal's insulting," but-

   6. RHRyan Holiday39:36

      Yeah

   7. SPSam Parr39:36

      ... like that's what... I was like, "You're a... I'm never gonna be seven feet tall, but like-

   8. RHRyan Holiday39:40

      Yeah

   9. SPSam Parr39:40

      ... you know, like your mentality is achievable." You know what I mean? But-

   10. RHRyan Holiday39:43

       Well, it's, it's kind of funny. As cr- I, I do feel the same way about Chris, uh, and, and his wife and, and my wife are friends. Um, but like, uh, every once in a while I'll mention one, one of them to the other, and then I forget that they... Uh, uh, Chris said something to me, actually, when I had him on The Daily Stoke podcast. He's like, "You know, he's elbowed me in the face like a lot."

   11. SPSam Parr40:05

       [laughs]

   12. RHRyan Holiday40:06

       Like, like it was like realizing like, like their best and worst moments came l- like the, the moment in both of their careers came at each other's expense, right? [laughs] Like, like, uh, Manu goes up for a rebound that, that Chris gets, that Chris tips back to Ray Allen, who makes a three-pointer to win th- to basically win the series, right? Like, it, it is also weird to think like, yeah, here are these like kind of two people that I admire, and then [laughs] they're on like a, their careers were like on a collision course with each other.

   13. SPSam Parr40:39

       Are they buddies now?

   14. RHRyan Holiday40:40

       I don't think so. No, [laughs] 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 [laughs] socially. That, it might take some time. Like maybe, maybe in 20 years, uh, the, that rivalry fades away.

   15. SPSam Parr40:57

       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"?

   16. RHRyan Holiday41:04

       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. I d- it, not 'cause I... Uh, 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 th- 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's 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, uh, and his son, and, uh, uh, our mutual friend to their house in the Hamptons where we had dinner, and then it flew us back to Manhattan after dinner. Um-

   17. SPSam Parr41:46

       What?

   18. RHRyan Holiday41:47

       Yeah, it was fucking nuts. Uh, it was super nuts. But, like talking to this person, um, he was like, I was like, "So what's going on with you?" And he's like, "Well, you know, my youngest just went away to college, so we're empty nesters. Like, we're gonna spend an extra couple weeks here in the Hamptons." And, uh, it, it was like, um, again, I think at the end of your life and y- uh, when you reflect on whether you were successful or not, you're gonna think like, "What is, do my kids want to spend time with me or not? Like, am I, what is, 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 a, he has a business that he founded with his son. Like, I, I, I like, to me, v- when I see stuff like that, I'm like, okay, this is fundamentally not normal in that like y- we just flew on a helicopter to have dinner and that was like, you know, like a wave of the hand for you.

   19. SPSam Parr42:53

       [laughs]

   20. RHRyan Holiday42:54

       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.

   21. SPSam Parr43:09

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

   22. RHRyan Holiday43:14

       Yeah. Uh-huh.

   23. SPSam Parr43:15

       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, five or 10 years, like a long time, in order to like, "Hey, when you see Gawker screw up, you tell me, and we're gonna pounce, and we're gonna sue them-

   24. RHRyan Holiday43:36

       Yeah

   25. SPSam Parr43:36

       ... because they outed me out as being gay." Or you also told another story about how Peter Thiel had a Mercedes, a, a black Mercedes everywhere he went that was just ready to roll in case anything bad happened.

   26. RHRyan Holiday43:48

       Yeah.

   27. SPSam Parr43:48

       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. It w- is that true, or am I making that up?

   28. RHRyan Holiday43:57

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

   29. SPSam Parr44:07

       Yeah, just like all this crazy stuff. What, um-

   30. RHRyan Holiday44:10

       Sure
6. 47:34 – 53:41

   The pros and cons of reality distortion fields

   1. SPSam Parr47:34

      "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-

   2. RHRyan Holiday47:40

      Yeah

   3. SPSam Parr47:40

      ... my, my tr- the thing I want it 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 lot, the, 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.

   4. RHRyan Holiday47:58

      Yeah.

   5. SPSam Parr47:58

      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, I, 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?

   6. RHRyan Holiday48:16

      I, I've seen up close, I, 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 d- Dov Charney was my direct boss, right? Like, he would call me five 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, 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've already been done. You were able to create something from nothing, I g- 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 Charney's like, "I'm gonna 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."

   7. SPSam Parr50:25

      [laughs]

   8. RHRyan Holiday50:25

      Right? And so he crashes and burns as a result of this e- 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, do you ever, you, you ever heard that expression, the political expression about the reality-based community? Do you know that?

   9. SPSam Parr50:44

      No. No, what's that?

   10. RHRyan Holiday50:45

       So, so as, as Georg- a- as George Bush was contemplating the invasion of Iraq, I think it was Karl Rove, but I, I've, one of, one of the officials in the Bush administration, you know, is responding to all the people who are like, "It's gonna be an enormous quagmire. You're not gonna get the, the... Like, right now you have no international support," blah, blah, "It's gonna cost this," o- 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 his own, 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, et cetera.

   11. SPSam Parr51:38

       But they're not always wrong.

   12. RHRyan Holiday51:39

       That's just f- not true.

   13. SPSam Parr51:40

       Be- but, but it's, it's not true maybe in that case, but, like, the, that, that feeling is-

   14. RHRyan Holiday51:45

       Yeah

   15. SPSam Parr51:45

       ... cousins to-

   16. RHRyan Holiday51:47

       Yeah

   17. SPSam Parr51:47

       ... uh, cousins to the other w- to it working. Do you know what I mean? To-

   18. RHRyan Holiday51:51

       Totally. Totally

   19. SPSam Parr51:52

       ... where, where, where's Chernobyl from?

   20. RHRyan Holiday51:54

       Uh, Argentina.

   21. SPSam Parr51:55

       Like, this Argentinian dude is gonna come and, like, be the boss and, like, kill it in t- like, you know what I mean? Like, they, they, they're, they're cousins.

   22. RHRyan Holiday52:04

       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. Uh, 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, three 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 gra- he was not Kanye West going around, saying, "I'm Steve Jobs," right? Like, th- this was-

   23. SPSam Parr52:52

       Yeah

   24. RHRyan Holiday52:52

       ... he, he was, like, uh, i- in the Churchill book, they talk about this. Churchill did not at the, a- a- 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 Ye- like, what Ch- what, what, what Churchill does is he buys some time, right? Like, all of these things start small, and they build. They're, th- 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.

   25. SPSam Parr53:35

       Dude, that's crazy fascinating to me. I, I gotta keep thinking about that. An- but, um, another thing that you're associated

7. 53:41 – 1:13:30

   Ryan's ghost town

   1. SPSam Parr53:41

      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-

   2. RHRyan Holiday53:50

      Yeah

   3. SPSam Parr53:50

      ... I'm a very, very, very small investor in. But the reason why it's awesome-

   4. RHRyan Holiday53:54

      Me too

   5. SPSam Parr53:54

      ... i- is... No, you're not a small investor. You're the guy. Uh, th- the reason why it's awesome to-

   6. RHRyan Holiday53:59

      Brent is the guy

   7. SPSam Parr54:00

      ... well, you're, you're, you're, I, I view you, Brent, and Nathan, uh, Nathan Barry as like, uh, you know, the, the guys. But, uh, 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 six 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-

   8. RHRyan Holiday54:42

      Yeah

   9. SPSam Parr54:42

      ... 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, what, uh, what, what's your feeling on how everything's going with that, and, like, what's the plan?

   10. RHRyan Holiday55:10

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

   11. SPSam Parr55:18

       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 his shit so good?

   12. RHRyan Holiday55:27

       It's an amazing story, and it actually goes to what we were just talking about. Like, the, the idea in, i- as an outsider or, or in retrospect, it feels like guy makes brilliant investment, buys town, turns it into a YouTube channel, makes these amazing videos in the span of a couple months-

   13. SPSam Parr55:44

       And it seems obvious now

   14. RHRyan Holiday55:44

       ... blows up. Yeah. Um, but that's not how it went at all, right? Like, first off, when, when he first-

   15. SPSam Parr55:50

       And, and by the way, what's the name of the channel?

   16. RHRyan Holiday55:52

       Uh, Ghost Town Living.

   17. SPSam Parr55:54

       Okay.

   18. RHRyan Holiday55:55

       Uh, when, when he first told me about it, I was like, "Dude, that's a horrible idea. 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, find, build a hotel on the site, and make it some sort of, like, luxury resort thing. That, that, that they failed to do for, like, two years. Maybe even three years. He had no intention of living up there. It was losing money hand over fist, right? Like, he, I would say-

   19. SPSam Parr56:23

       How many acres is it?

   20. RHRyan Holiday56:24

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

   21. SPSam Parr56:30

       And it's, like, in the mountains of-

   22. RHRyan Holiday56:31

       ... it's basically unlimited land

   23. SPSam Parr56:32

       ... like, four hours outside of LA?

   24. RHRyan Holiday56:34

       It's, yeah, it's about three and a half hours from LA. It, it looks down, uh, on Death Valley at, at about 8,500, uh, feet. It was once the largest silver mine in the United States. So it's funny-

   25. SPSam Parr56:46

       But there's like no water and electricity, right? Like, there's not-

   26. RHRyan Holiday56:48

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

   27. SPSam Parr56:53

       Oh, but there wasn't, I guess, is what I mean.

   28. RHRyan Holiday56:55

       There, 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 four-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, 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 it, it, 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 this-

   29. SPSam Parr57:44

       Well, Brent's 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 times. It seems like he just kinda turned on this charm and charisma, and it was, like, intoxicating.

   30. RHRyan Holiday57:56

       He's always been like a behind-the-scenes person and, 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'm 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 have 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.

Episode duration: 1:13:30