Ryan Holiday, author of “Discipline is Destiny,” joins the podcast to discuss the realities of the book publishing industry, the mechanics of bestseller lists, and his experiences with high-profile figures like Peter Thiel. He shares insights into the financial side of being an author, the impact of different book formats, and his personal approach to building a sustainable career.
Topics: Book publishing, bestseller lists, Peter Thiel, entrepreneurship, marketing, personal development, writing, media strategy.
The Reality of Book Sales and Bestseller Lists [00:00]
Sam Parr: And then I Googled like Mark Manson house, because 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 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.
Ryan Holiday: My man, Ryan Holiday. What’s going on? Nice to nice to talk to you.
Shaan Puri: It’s good to talk to you, too.
Ryan Holiday: Um, so you you you asked to come here and I’ll just because 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?
Ryan Holiday: Yes. Discipline is Destiny. This is the new one for the series. Uh, and yeah, it came out yesterday.
Sam Parr: Oh, and how’s it going so far?
Ryan Holiday: 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. 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.
Sam Parr: What do you think is the outcome of this one’s going to be?
Ryan Holiday: 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.
Sam Parr: 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?
Ryan Holiday: 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, because the whole point of writing a book is for people to read it.
Sam Parr: 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?
Ryan Holiday: There’s there’s sort of three lists. There’s New York Times, which you 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 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.
Sam Parr: 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 dollar 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 six pages of 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 it’s it’s 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.
Ryan Holiday: It’s actually 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. I think they’re owned by uh a parent company. I forget the parent company. They’re owned by Bertelsmann or something like that. Yeah, yeah, yeah, that’s right. But um, here let’s uh revenues. Their revenues, I bet I uh 4 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. And what do they cost? 20 bucks? Yeah, so so if you 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, because the whole point of writing a book is for people to read it.
The Economics of Book Formats and Royalties [01:54]
Sam Parr: 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?
Ryan Holiday: 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, because the whole point of writing a book is for people to read it.
Sam Parr: What do they cost? 20 bucks?
Ryan Holiday: Yeah, so so if you think about, like my books, I’ve sold 5 million copies. If you sell it 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. At 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 very 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 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 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, and I I know Mark and he’s amazing. The distinction the the decision to put your book in paperback is actually a multi-million 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 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 dollars 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 third 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 is sold tens of, 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.
Sam Parr: What about Audible and Ebook?
Ryan Holiday: So, Audible, you make uh I think it’s the same as 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 bucks or nine bucks uh for for Ebooks a lot of times. Uh so so somewhere between two and three bucks a book you make across formats.
Sam Parr: So, how much 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 20 million books times hardcover price or you know, it 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, 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. 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 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 going to be overstating the cash they have on hand.
The Reality of Bestseller Lists and Author Success [01:54]
Sam Parr: So, you’ve sold 100 million in books, so then like the estimate based off of the numbers you said, it’d be like around 13, 14, 15% take home. I mean, how many authors are doing that? Selling 5 million books? Very, 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, you know, offered them an an obscure book about ancient philosophy in 2011, 2012 for for the Stoic book for a 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.
Sam Parr: 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 I arguably, like just guessing, maybe he’s worth 150 to 250 million dollars 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 uh revenue streams?
Ryan Holiday: I don’t know. I don’t I don’t do that many investments, but it is weird. Like I 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 have 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 quite good.
Sam Parr: 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 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 just not, but it’s very hard. It seems it seems almost impossible.
Ryan Holiday: It is super weird though because uh like a lot wealthy people read books, right? They 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 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 going to 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 Alan 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 it Yeah, he was it’s like that that story about the, you know, the fisherman 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.
Sam Parr: 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. 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 you I 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.
Ryan Holiday: 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 a better job learning those those big philosophical lessons like sort of where do you rain 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 the stoicism or the philosophy sort of uh connects with me and and by the way that story that about the fisherman that actually traces back to like the 14th century about uh it’s a story about a prince uh advising a king or an advisor advising a prince. Uh so the story goes way back. I feel like I get that better than I do stuff that might be seem really easy for most people, which is just like, you know, sort of day-to-day emotional management.
Sam Parr: How you said something really cool on the uh I was listening to this the other day. There’s two things that suck 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 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 want to do this. This doesn’t this doesn’t speak to me. This is not how I want to spend my time. 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 want to 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 them or a dozen of them plus, and then you have uh the podcast and then you have the YouTube channel. And I’m like, how on earth are you how are you outputting all this stuff? It’s always awesome. I love all your shit.
Ryan Holiday: 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 so to do it because you think it’ll make money or it’s what like 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 because I’m doing this four 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 I think I tend to have uh more energy to make stuff than there actually is like pipes to put stuff out. That’s just like how it shook out. Um and I I agree like I I I 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 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 did it It’s like a slow burn. It probably Yeah, it it 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 four to five 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 to have a big niche, but for it still to very much be a niche, right? Like uh there’s just more people haven’t heard of me than have heard of me and that is a nice place to operate in.
Sam Parr: Dude, so many people so the hustle we were a daily email and then me and Sean do this thing three days a week and people are like, hey, how are you doing quantity? I want to 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 you know, you like the the output here or like the if this were a 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.
Ryan Holiday: Yeah, I think 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 a book or something. So I like I I’ve done a free email every day for six years, right? Um, that that’s built a business, but But you’re 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 system I have systems that make it easier. Is that the dad or Both, both. You you 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 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 nine on Daily Dad that are ready to record and eight that are recorded but not scheduled. So like And that’s your system? Yeah, so I I’m just doing 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 three 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.
Sam Parr: Are you uh writing the scripts to your YouTube videos? I think you’re only doing one or two a week, right?
Ryan Holiday: Yes. Uh so YouTube uh I have a I have a I have a actually wait, let me I’ll come back to that in a second. The other thing I would say about the people who are like, oh, I really want to get to quality, that’s why I take 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 five years and I’m like, where? Show show me five years of work in this thing, right? I’m I’m not arguing with you that it it transpired over five years, but I don’t think you showed up and worked on this as you said, like a job every day for five years. I think it either it 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 Green or Robert Caro or you know, one of these greats, I’m like, I see the I see the five years. Like it’s obvious. Like you were like Robert Green was telling me the other day, he’s like seven 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 Green and um the uh what’s his uh what’s Caro’s book, Moses? Um 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 1500 or 1300 word like epic. And then and pretty much like Titan is like this too. Anything Ron Chernow does. Yes. Every sentence have like to me, it’s like a life’s work and if they’re lucky, they can maybe get three 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 it 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.
Ryan Holiday: 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 uh the 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 stage those those sentences. So yeah, like there’s definitely people who there’s a reason they only do two or three 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 uh meditations on a larger idea. But if it is a like, you know, how to read Marcus Aurelius, how to read Seneca, um 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.
Sam Parr: Are you using Google Docs?
Ryan Holiday: Yeah, for the for the most part, yeah.
Sam Parr: And how big’s the team?
Ryan Holiday: Uh like 10 people now, probably. And that includes that includes the bookstore.
Sam Parr: And also does it include Daily Stoic and uh uh Daily Dad?
Ryan Holiday: Yeah, yeah. I’m saying I probably have 10 employees, maybe maybe 11 or 12, but but less than 15.
Sam Parr: Dude, that is crazy, man. The output is just awesome. I I I think that’s amazing.
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Sam Parr: 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 I 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. 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 have you looked into these Book of the Month businesses? I think Reese Witherspoon had one too that I think was profitable.
Ryan Holiday: 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 because 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 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. Um 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.
Sam Parr: How much revenue can you make on one send?
Ryan Holiday: Uh from from the reading list newsletter? I don’t know. Um I don’t know. Uh I actually 10 or 20 grand maybe. Yeah, that that would be that would be a 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 want to 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 who’s my high or my 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 uh like complaining to me. He’s 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 it’s right, it’s the same thing we’re 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 I 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 I got some early shares in Vinyl Me when it came out. So and that’s been a surprisingly big business. Like I 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 a thousand 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? Like 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 I think with a book, like people have so little room to read in their lives that I 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.
Sam Parr: 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?
Ryan Holiday: 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. 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 want to say he’s a regular person because that sounds like 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 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 like fundamentally 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, 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 want to be world class at what I do and and like be a somewhat of a normal person. Like it’s almost easier to be great than it is to be good, if that makes sense.
Sam Parr: Yeah, that’s awesome. Who who who else have you uh who have you met? So I 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 kind of yeah, maybe normal’s insulting, but like that’s what it I was like, you’re a I’m never going to be 7 ft tall, but like, you know, like your mentality is achievable. You know what I mean? Well, it’s It’s kind of funny as 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 it I 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 three-pointer to win 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 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 want to say who it is. I not because I it not because I it I feel weird uh dropping the name. But anyways, let’s just say I met this musician and he’d read the books and he reached out to me to 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 going to 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 a 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 What? 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? 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 weeks here in the Hamptons. And it it it was like um again, I think at the end of your life and you 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 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 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 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 you like spending time together. Dude, so many people so the hustle we were a daily email and then me and Sean do this thing three days a week and people are like, hey, how are you doing quantity? I want to 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 you know, you like the the output here or like the if this were a 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 think 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 a book or something. So I like I I’ve done a free email every day for six years, right? Um, that that’s built a business, but But you’re 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 system I have systems that make it easier. Is that the dad or Both, both. You you 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 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 nine on Daily Dad that are ready to record and eight that are recorded but not scheduled. So like And that’s your system? Yeah, so I I’m just doing 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 three 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.
Sam Parr: Are you uh writing the scripts to your YouTube videos? I think you’re only doing one or two a week, right?
Ryan Holiday: Yes. Uh so YouTube uh I have a I have a I have a actually wait, let me I’ll come back to that in a second. The other thing I would say about the people who are like, oh, I really want to get to quality, that’s why I take 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 five years and I’m like, where? Show show me five years of work in this thing, right? I’m I’m not arguing with you that it it transpired over five years, but I don’t think you showed up and worked on this as you said, like a job every day for five years. I think it either it 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 Green or Robert Caro or you know, one of these greats, I’m like, I see the I see the five years. Like it’s obvious. Like you were like Robert Green was telling me the other day, he’s like seven 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 Green and um the uh what’s his uh what’s Caro’s book, Moses? Um 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 1500 or 1300 word like epic. And then and pretty much like Titan is like this too. Anything Ron Chernow does. Yes. Every sentence have like to me, it’s like a life’s work and if they’re lucky, they can maybe get three 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 it 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.
Ryan Holiday: 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 uh the 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 stage those those sentences. So yeah, like there’s definitely people who there’s a reason they only do two or three 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 uh meditations on a larger idea. But if it is a like, you know, how to read Marcus Aurelius, how to read Seneca, um 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.
Sam Parr: Are you using Google Docs?
Ryan Holiday: Yeah, for the for the most part, yeah.
Sam Parr: And how big’s the team?
Ryan Holiday: Uh like 10 people now, probably. And that includes that includes the bookstore.
Sam Parr: And also does it include Daily Stoic and uh uh Daily Dad?
Ryan Holiday: Yeah, yeah. I’m saying I probably have 10 employees, maybe maybe 11 or 12, but but less than 15.
Sam Parr: Dude, that is crazy, man. The output is just awesome. I I I think that’s amazing.
Sam Parr: 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 I 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. 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 have you looked into these Book of the Month businesses? I think Reese Witherspoon had one too that I think was profitable.
Ryan Holiday: 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 because 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 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. Um 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.
Sam Parr: How much revenue can you make on one send?
Ryan Holiday: Uh from from the reading list newsletter? I don’t know. Um I don’t know. Uh I actually 10 or 20 grand maybe. Yeah, that that would be that would be a 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 want to 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 who’s my high or my 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 uh like complaining to me. He’s 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 it’s right, it’s the same thing we’re 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 I 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 I got some early shares in Vinyl Me when it came out. So and that’s been a surprisingly big business. Like I 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 a thousand 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? Like 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 I think with a book, like people have so little room to read in their lives that I 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.
Sam Parr: 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?
Ryan Holiday: 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. 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 want to say he’s a regular person because that sounds like 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 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 like fundamentally 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, 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 want to be world class at what I do and and like be a somewhat of a normal person. Like it’s almost easier to be great than it is to be good, if that makes sense.
Sam Parr: Yeah, that’s awesome. Who who who else have you uh who have you met? So I 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 kind of yeah, maybe normal’s insulting, but like that’s what it I was like, you’re a I’m never going to be 7 ft tall, but like, you know, like your mentality is achievable. You know what I mean? Well, it’s It’s kind of funny as 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 it I 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 three-pointer to win 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 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 want to say who it is. I not because I it not because I it I feel weird uh dropping the name. But anyways, let’s just say I met this musician and he’d read the books and he reached out to me to 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 going to 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 a 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 What? 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? 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 weeks here in the Hamptons. And it it it was like um again, I think at the end of your life and you 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 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 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 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 you like spending time together. Dude, so many people so the hustle we were a daily email and then me and Sean do this thing three days a week and people are like, hey, how are you doing quantity? I want to 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 you know, you like the the output here or like the if this were a 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 think 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 a book or something. So I like I I’ve done a free email every day for six years, right? Um, that that’s built a business, but But you’re 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 system I have systems that make it easier. Is that the dad or Both, both. You you 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 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 nine on Daily Dad that are ready to record and eight that are recorded but not scheduled. So like And that’s your system? Yeah, so I I’m just doing 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 three 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.
Sam Parr: Are you uh writing the scripts to your YouTube videos? I think you’re only doing one or two a week, right?
Ryan Holiday: Yes. Uh so YouTube uh I have a I have a I have a actually wait, let me I’ll come back to that in a second. The other thing I would say about the people who are like, oh, I really want to get to quality, that’s why I take 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 five years and I’m like, where? Show show me five years of work in this thing, right? I’m I’m not arguing with you that it it transpired over five years, but I don’t think you showed up and worked on this as you said, like a job every day for five years. I think it either it 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 Green or Robert Caro or you know, one of these greats, I’m like, I see the I see the five years. Like it’s obvious. Like you were like Robert Green was telling me the other day, he’s like seven 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 Green and um the uh what’s his uh what’s Caro’s book, Moses? Um 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 1500 or 1300 word like epic. And then and pretty much like Titan is like this too. Anything Ron Chernow does. Yes. Every sentence have like to me, it’s like a life’s work and if they’re lucky, they can maybe get three 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 it 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.
Ryan Holiday: 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 uh the 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 stage those those sentences. So yeah, like there’s definitely people who there’s a reason they only do two or three 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 uh meditations on a larger idea. But if it is a like, you know, how to read Marcus Aurelius, how to read Seneca, um 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.
Sam Parr: Are you using Google Docs?
Ryan Holiday: Yeah, for the for the most part, yeah.
Sam Parr: And how big’s the team?
Ryan Holiday: Uh like 10 people now, probably. And that includes that includes the bookstore.
Sam Parr: And also does it include Daily Stoic and uh uh Daily Dad?
Ryan Holiday: Yeah, yeah. I’m saying I probably have 10 employees, maybe maybe 11 or 12, but but less than 15.
Sam Parr: Dude, that is crazy, man. The output is just awesome. I I I think that’s amazing.
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Sam Parr: 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 I 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. 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 have you looked into these Book of the Month businesses? I think Reese Witherspoon had one too that I think was profitable.
Ryan Holiday: 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 because 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 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. Um 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.
Sam Parr: How much revenue can you make on one send?
Ryan Holiday: Uh from from the reading list newsletter? I don’t know. Um I don’t know. Uh I actually 10 or 20 grand maybe. Yeah, that that would be that would be a 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 want to 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 who’s my high or my 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 uh like complaining to me. He’s 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 it’s right, it’s the same thing we’re 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 I 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 I got some early shares in Vinyl Me when it came out. So and that’s been a surprisingly big business. Like I 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 a thousand 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? Like 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 I think with a book, like people have so little room to read in their lives that I 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.
Sam Parr: 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?
Ryan Holiday: 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. 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 want to say he’s a regular person because that sounds like 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 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 like fundamentally 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, 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 want to be world class at what I do and and like be a somewhat of a normal person. Like it’s almost easier to be great than it is to be good, if that makes sense.
Sam Parr: Yeah, that’s awesome. Who who who else have you uh who have you met? So I 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 kind of yeah, maybe normal’s insulting, but like that’s what it I was like, you’re a I’m never going to be 7 ft tall, but like, you know, like your mentality is achievable. You know what I mean? Well, it’s It’s kind of funny as 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 it I 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 three-pointer to win 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 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 want to say who it is. I not because I it not because I it I feel weird uh dropping the name. But anyways, let’s just say I met this musician and he’d read the books and he reached out to me to 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 going to 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 a 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 What? 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? 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 weeks here in the Hamptons. And it it it was like um again, I think at the end of your life and you 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 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 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 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 you like spending time together. Dude, so many people so the hustle we were a daily email and then me and Sean do this thing three days a week and people are like, hey, how are you doing quantity? I want to 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 you know, you like the the output here or like the if this were a 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 think 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 a book or something. So I like I I’ve done a free email every day for six years, right? Um, that that’s built a business, but But you’re 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 system I have systems that make it easier. Is that the dad or Both, both. You you 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 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 nine on Daily Dad that are ready to record and eight that are recorded but not scheduled. So like And that’s your system? Yeah, so I I’m just doing 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 three 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.
Sam Parr: Are you uh writing the scripts to your YouTube videos? I think you’re only doing one or two a week, right?
Ryan Holiday: Yes. Uh so YouTube uh I have a I have a I have a actually wait, let me I’ll come back to that in a second. The other thing I would say about the people who are like, oh, I really want to get to quality, that’s why I take 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 five years and I’m like, where? Show show me five years of work in this thing, right? I’m I’m not arguing with you that it it transpired over five years, but I don’t think you showed up and worked on this as you said, like a job every day for five years. I think it either it 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 Green or Robert Caro or you know, one of these greats, I’m like, I see the I see the five years. Like it’s obvious. Like you were like Robert Green was telling me the other day, he’s like seven 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 Green and um the uh what’s his uh what’s Caro’s book, Moses? Um 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 1500 or 1300 word like epic. And then and pretty much like Titan is like this too. Anything Ron Chernow does. Yes. Every sentence have like to me, it’s like a life’s work and if they’re lucky, they can maybe get three 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 it 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.
Ryan Holiday: 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 uh the 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 stage those those sentences. So yeah, like there’s definitely people who there’s a reason they only do two or three 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 uh meditations on a larger idea. But if it is a like, you know, how to read Marcus Aurelius, how to read Seneca, um 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.
Sam Parr: Are you using Google Docs?
Ryan Holiday: Yeah, for the for the most part, yeah.
Sam Parr: And how big’s the team?
Ryan Holiday: Uh like 10 people now, probably. And that includes that includes the bookstore.
Sam Parr: And also does it include Daily Stoic and uh uh Daily Dad?
Ryan Holiday: Yeah, yeah. I’m saying I probably have 10 employees, maybe maybe 11 or 12, but but less than 15.
Sam Parr: Dude, that is crazy, man. The output is just awesome. I I I think that’s amazing.
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Sam Parr: 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 I 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. 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 have you looked into these Book of the Month businesses? I think Reese Witherspoon had one too that I think was profitable.
Ryan Holiday: 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 because 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 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. Um 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.
Sam Parr: How much revenue can you make on one send?
Ryan Holiday: Uh from from the reading list newsletter? I don’t know. Um I don’t know. Uh I actually 10 or 20 grand maybe. Yeah, that that would be that would be a 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 want to 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 who’s my high or my 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 uh like complaining to me. He’s 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 it’s right, it’s the same thing we’re 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 I 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 I got some early shares in Vinyl Me when it came out. So and that’s been a surprisingly big business. Like I 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 a thousand 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? Like 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 I think with a book, like people have so little room to read in their lives that I 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.
Sam Parr: 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?
Ryan Holiday: 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. 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 want to say he’s a regular person because that sounds like 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 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 like fundamentally 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, 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 want to be world class at what I do and and like be a somewhat of a normal person. Like it’s almost easier to be great than it is to be good, if that makes sense.
Sam Parr: Yeah, that’s awesome. Who who who else have you uh who have you met? So I 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 kind of yeah, maybe normal’s insulting, but like that’s what it I was like, you’re a I’m never going to be 7 ft tall, but like, you know, like your mentality is achievable. You know what I mean? Well, it’s It’s kind of funny as 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 it I 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 three-pointer to win 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 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 want to say who it is. I not because I it not because I it I feel weird uh dropping the name. But anyways, let’s just say I met this musician and he’d read the books and he reached out to me to 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 going to 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 a 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 What? 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? 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 weeks here in the Hamptons. And it it it was like um again, I think at the end of your life and you 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 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 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 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 you like spending time together. Dude, so many people so the hustle we were a daily email and then me and Sean do this thing three days a week and people are like, hey, how are you doing quantity? I want to 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 you know, you like the the output here or like the if this were a 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 think 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 a book or something. So I like I I’ve done a free email every day for six years, right? Um, that that’s built a business, but But you’re 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 system I have systems that make it easier. Is that the dad or Both, both. You you 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 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 nine on Daily Dad that are ready to record and eight that are recorded but not scheduled. So like And that’s your system? Yeah, so I I’m just doing 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 three 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.
Sam Parr: Are you uh writing the scripts to your YouTube videos? I think you’re only doing one or two a week, right?
Ryan Holiday: Yes. Uh so YouTube uh I have a I have a I have a actually wait, let me I’ll come back to that in a second. The other thing I would say about the people who are like, oh, I really want to get to quality, that’s why I take 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 five years and I’m like, where? Show show me five years of work in this thing, right? I’m I’m not arguing with you that it it transpired over five years, but I don’t think you showed up and worked on this as you said, like a job every day for five years. I think it either it 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 Green or Robert Caro or you know, one of these greats, I’m like, I see the I see the five years. Like it’s obvious. Like you were like Robert Green was telling me the other day, he’s like seven 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 Green and um the uh what’s his uh what’s Caro’s book, Moses? Um 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 1500 or 1300 word like epic. And then and pretty much like Titan is like this too. Anything Ron Chernow does. Yes. Every sentence have like to me, it’s like a life’s work and if they’re lucky, they can maybe get three 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 it 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.
Ryan Holiday: 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 uh the 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 stage those those sentences. So yeah, like there’s definitely people who there’s a reason they only do two or three 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 uh meditations on a larger idea. But if it is a like, you know, how to read Marcus Aurelius, how to read Seneca, um 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.
Sam Parr: Are you using Google Docs?
Ryan Holiday: Yeah, for the for the most part, yeah.
Sam Parr: And how big’s the team?
Ryan Holiday: Uh like 10 people now, probably. And that includes that includes the bookstore.
Sam Parr: And also does it include Daily Stoic and uh uh Daily Dad?
Ryan Holiday: Yeah, yeah. I’m saying I probably have 10 employees, maybe maybe 11 or 12, but but less than 15.
Sam Parr: Dude, that is crazy, man. The output is just awesome. I I I think that’s amazing.
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Sam Parr: 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 I 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. 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 have you looked into these Book of the Month businesses? I think Reese Witherspoon had one too that I think was profitable.
Ryan Holiday: 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 because 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 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. Um 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.
Sam Parr: How much revenue can you make on one send?
Ryan Holiday: Uh from from the reading list newsletter? I don’t know. Um I don’t know. Uh I actually 10 or 20 grand maybe. Yeah, that that would be that would be a 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 want to 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 who’s my high or my 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 uh like complaining to me. He’s 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 it’s right, it’s the same thing we’re 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 I 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 I got some early shares in Vinyl Me when it came out. So and that’s been a surprisingly big business. Like I 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 a thousand 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? Like 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 I think with a book, like people have so little room to read in their lives that I 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.
Sam Parr: 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?
Ryan Holiday: 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. 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 want to say he’s a regular person because that sounds like 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 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 like fundamentally 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, 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 want to be world class at what I do and and like be a somewhat of a normal person. Like it’s almost easier to be great than it is to be good, if that makes sense.
Sam Parr: Yeah, that’s awesome. Who who who else have you uh who have you met? So I 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 kind of yeah, maybe normal’s insulting, but like that’s what it I was like, you’re a I’m never going to be 7 ft tall, but like, you know, like your mentality is achievable. You know what I mean? Well, it’s It’s kind of funny as 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 it I 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 three-pointer to win 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 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 want to say who it is. I not because I it not because I it I feel weird uh dropping the name. But anyways, let’s just say I met this musician and he’d read the books and he reached out to me to 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 going to 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 a 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 What? 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? 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 weeks here in the Hamptons. And it it it was like um again, I think at the end of your life and you 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 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 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 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 you like spending time together. Dude, so many people so the hustle we were a daily email and then me and Sean do this thing three days a week and people are like, hey, how are you doing quantity? I want to 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 you know, you like the the output here or like the if this were a 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 think 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 a book or something. So I like I I’ve done a free email every day for six years, right? Um, that that’s built a business, but But you’re 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 system I have systems that make it easier. Is that the dad or Both, both. You you 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 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 nine on Daily Dad that are ready to record and eight that are recorded but not scheduled. So like And that’s your system? Yeah, so I I’m just doing 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 three 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.
Sam Parr: Are you uh writing the scripts to your YouTube videos? I think you’re only doing one or two a week, right?
Ryan Holiday: Yes. Uh so YouTube uh I have a I have a I have a actually wait, let me I’ll come back to that in a second. The other thing I would say about the people who are like, oh, I really want to get to quality, that’s why I take 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 five years and I’m like, where? Show show me five years of work in this thing, right? I’m I’m not arguing with you that it it transpired over five years, but I don’t think you showed up and worked on this as you said, like a job every day for five years. I think it either it 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 Green or Robert Caro or you know, one of these greats, I’m like, I see the I see the five years. Like it’s obvious. Like you were like Robert Green was telling me the other day, he’s like seven 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 Green and um the uh what’s his uh what’s Caro’s book, Moses? Um 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 1500 or 1300 word like epic. And then and pretty much like Titan is like this too. Anything Ron Chernow does. Yes. Every sentence have like to me, it’s like a life’s work and if they’re lucky, they can maybe get three 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 it 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.
Ryan Holiday: 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 uh the 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 stage those those sentences. So yeah, like there’s definitely people who there’s a reason they only do two or three 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 uh meditations on a larger idea. But if it is a like, you know, how to read Marcus Aurelius, how to read Seneca, um 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.
Sam Parr: Are you using Google Docs?
Ryan Holiday: Yeah, for the for the most part, yeah.
Sam Parr: And how big’s the team?
Ryan Holiday: Uh like 10 people now, probably. And that includes that includes the bookstore.
Sam Parr: And also does it include Daily Stoic and uh uh Daily Dad?
Ryan Holiday: Yeah, yeah. I’m saying I probably have 10 employees, maybe maybe 11 or 12, but but less than 15.
Sam Parr: Dude, that is crazy, man. The output is just awesome. I I I think that’s amazing.
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Sam Parr: 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 I 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. 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 have you looked into these Book of the Month businesses? I think Reese Witherspoon had one too that I think was profitable.
Ryan Holiday: 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 because 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 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. Um 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.
Sam Parr: How much revenue can you make on one send?
Ryan Holiday: Uh from from the reading list newsletter? I don’t know. Um I don’t know. Uh I actually 10 or 20 grand maybe. Yeah, that that would be that would be a 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 want to 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 who’s my high or my 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 uh like complaining to me. He’s 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 it’s right, it’s the same thing we’re 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 I 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 I got some early shares in Vinyl Me when it came out. So and that’s been a surprisingly big business. Like I 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 a thousand 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? Like 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 I think with a book, like people have so little room to read in their lives that I 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.
Sam Parr: 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?
Ryan Holiday: 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. 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 want to say he’s a regular person because that sounds like 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 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 like fundamentally 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, 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 want to be world class at what I do and and like be a somewhat of a normal person. Like it’s almost easier to be great than it is to be good, if that makes sense.
Sam Parr: Yeah, that’s awesome. Who who who else have you uh who have you met? So I 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 kind of yeah, maybe normal’s insulting, but like that’s what it I was like, you’re a I’m never going to be 7 ft tall, but like, you know, like your mentality is achievable. You know what I mean? Well, it’s It’s kind of funny as 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 it I 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 three-pointer to win 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 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 want to say who it is. I not because I it not because I it I feel weird uh dropping the name. But anyways, let’s just say I met this musician and he’d read the books and he reached out to me to 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 going to 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 a 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 What? 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? 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 weeks here in the Hamptons. And it it it was like um again, I think at the end of your life and you 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 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 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 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 you like spending time together. Dude, so many people so the hustle we were a daily email and then me and Sean do this thing three days a week and people are like, hey, how are you doing quantity? I want to 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 you know, you like the the output here or like the if this were a 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 think 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 a book or something. So I like I I’ve done a free email every day for six years, right? Um, that that’s built a business, but But you’re 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 system I have systems that make it easier. Is that the dad or Both, both. You you 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 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 nine on Daily Dad that are ready to record and eight that are recorded but not scheduled. So like And that’s your system? Yeah, so I I’m just doing 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 three 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.
Sam Parr: Are you uh writing the scripts to your YouTube videos? I think you’re only doing one or two a week, right?
Ryan Holiday: Yes. Uh so YouTube uh I have a I have a I have a actually wait, let me I’ll come back to that in a second. The other thing I would say about the people who are like, oh, I really want to get to quality, that’s why I take 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 five years and I’m like, where? Show show me five years of work in this thing, right? I’m I’m not arguing with you that it it transpired over five years, but I don’t think you showed up and worked on this as you said, like a job every day for five years. I think it either it 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 Green or Robert Caro or you know, one of these greats, I’m like, I see the I see the five years. Like it’s obvious. Like you were like Robert Green was telling me the other day, he’s like seven 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 Green and um the uh what’s his uh what’s Caro’s book, Moses? Um 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 1500 or 1300 word like epic. And then and pretty much like Titan is like this too. Anything Ron Chernow does. Yes. Every sentence have like to me, it’s like a life’s work and if they’re lucky, they can maybe get three 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 it 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.
Ryan Holiday: 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 uh the 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 stage those those sentences. So yeah, like there’s definitely people who there’s a reason they only do two or three 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 uh meditations on a larger idea. But if it is a like, you know, how to read Marcus Aurelius, how to read Seneca, um 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.
Sam Parr: Are you using Google Docs?
Ryan Holiday: Yeah, for the for the most part, yeah.
Sam Parr: And how big’s the team?
Ryan Holiday: Uh like 10 people now, probably. And that includes that includes the bookstore.
Sam Parr: And also does it include Daily Stoic and uh uh Daily Dad?
Ryan Holiday: Yeah, yeah. I’m saying I probably have 10 employees, maybe maybe 11 or 12, but but less than 15.
Sam Parr: Dude, that is crazy, man. The output is just awesome. I I I think that’s amazing.
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Sam Parr: 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 I 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. 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 have you looked into these Book of the Month businesses? I think Reese Witherspoon had one too that I think was profitable.
Ryan Holiday: 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 because 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 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. Um 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.
Sam Parr: How much revenue can you make on one send?
Ryan Holiday: Uh from from the reading list newsletter? I don’t know. Um I don’t know. Uh I actually 10 or 20 grand maybe. Yeah, that that would be that would be a 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 want to 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 who’s my high or my 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 uh like complaining to me. He’s 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 it’s right, it’s the same thing we’re 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 I 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 I got some early shares in Vinyl Me when it came out. So and that’s been a surprisingly big business. Like I 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 a thousand 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? Like 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 I think with a book, like people have so little room to read in their lives that I 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.
Sam Parr: 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?
Ryan Holiday: 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. 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 want to say he’s a regular person because that sounds like 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 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 like fundamentally 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, 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 want to be world class at what I do and and like be a somewhat of a normal person. Like it’s almost easier to be great than it is to be good, if that makes sense.
Sam Parr: Yeah, that’s awesome. Who who who else have you uh who have you met? So I 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 kind of yeah, maybe normal’s insulting, but like that’s what it I was like, you’re a I’m never going to be 7 ft tall, but like, you know, like your mentality is achievable. You know what I mean? Well, it’s It’s kind of funny as 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 it I 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 three-pointer to win 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 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 want to say who it is. I not because I it not because I it I feel weird uh dropping the name. But anyways, let’s just say I met this musician and he’d read the books and he reached out to me to 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 going to 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 a 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 What? 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? 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 weeks here in the Hamptons. And it it it was like um again, I think at the end of your life and you 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 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 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 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 you like spending time together. Dude, so many people so the hustle we were a daily email and then me and Sean do this thing three days a week and people are like, hey, how are you doing quantity? I want to 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 you know, you like the the output here or like the if this were a 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 think 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 a book or something. So I like I I’ve done a free email every day for six years, right? Um, that that’s built a business, but But you’re 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 system I have systems that make it easier. Is that the dad or Both, both. You you 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 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 nine on Daily Dad that are ready to record and eight that are recorded but not scheduled. So like And that’s your system? Yeah, so I I’m just doing 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 three 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.
Sam Parr: Are you uh writing the scripts to your YouTube videos? I think you’re only doing one or two a week, right?
Ryan Holiday: Yes. Uh so YouTube uh I have a I have a I have a actually wait, let me I’ll come back to that in a second. The other thing I would say about the people who are like, oh, I really want to get to quality, that’s why I take 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 five years and I’m like, where? Show show me five years of work in this thing, right? I’m I’m not arguing with you that it it transpired over five years, but I don’t think you showed up and worked on this as you said, like a job every day for five years. I think it either it 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 Green or Robert Caro or you know, one of these greats, I’m like, I see the I see the five years. Like it’s obvious. Like you were like Robert Green was telling me the other day, he’s like seven 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 Green and um the uh what’s his uh what’s Caro’s book, Moses? Um 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 1500 or 1300 word like epic. And then and pretty much like Titan is like this too. Anything Ron Chernow does. Yes. Every sentence have like to me, it’s like a life’s work and if they’re lucky, they can maybe get three 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 it 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.
Ryan Holiday: 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 uh the 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 stage those those sentences. So yeah, like there’s definitely people who there’s a reason they only do two or three 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 uh meditations on a larger idea. But if it is a like, you know, how to read Marcus Aurelius, how to read Seneca, um 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.
Sam Parr: Are you using Google Docs?
Ryan Holiday: Yeah, for the for the most part, yeah.
Sam Parr: And how big’s the team?
Ryan Holiday: Uh like 10 people now, probably. And that includes that includes the bookstore.
Sam Parr: And also does it include Daily Stoic and uh uh Daily Dad?
Ryan Holiday: Yeah, yeah. I’m saying I probably have 10 employees, maybe maybe 11 or 12, but but less than 15.
Sam Parr: Dude, that is crazy, man. The output is just awesome. I I I think that’s amazing.
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Sam Parr: 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 I 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. 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 have you looked into these Book of the Month businesses? I think Reese Witherspoon had one too that I think was profitable.
Ryan Holiday: 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 because 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 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. Um 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.
Sam Parr: How much revenue can you make on one send?
Ryan Holiday: Uh from from the reading list newsletter? I don’t know. Um I don’t know. Uh I actually 10 or 20 grand maybe. Yeah, that that would be that would be a 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 want to 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 who’s my high or my 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 uh like complaining to me. He’s 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 it’s right, it’s the same thing we’re 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 I 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 I got some early shares in Vinyl Me when it came out. So and that’s been a surprisingly big business. Like I 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 a thousand 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? Like 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 I think with a book, like people have so little room to read in their lives that I 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.
Sam Parr: 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?
Ryan Holiday: 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. 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 want to say he’s a regular person because that sounds like 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 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 like fundamentally 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, 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 want to be world class at what I do and and like be a somewhat of a normal person. Like it’s almost easier to be great than it is to be good, if that makes sense.
Sam Parr: Yeah, that’s awesome. Who who who else have you uh who have you met? So I 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 kind of yeah, maybe normal’s insulting, but like that’s what it I was like, you’re a I’m never going to be 7 ft tall, but like, you know, like your mentality is achievable. You know what I mean? Well, it’s It’s kind of funny as 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 it I 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 three-pointer to win 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 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 want to say who it is. I not because I it not because I it I feel weird uh dropping the name. But anyways, let’s just say I met this musician and he’d read the books and he reached out to me to 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 going to 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 a 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 What? 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? 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 weeks here in the Hamptons. And it it it was like um again, I think at the end of your life and you 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 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 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 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 you like spending time together. Dude, so many people so the hustle we were a daily email and then me and Sean do this thing three days a week and people are like, hey, how are you doing quantity? I want to 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 you know, you like the the output here or like the if this were a 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 think 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 a book or something. So I like I I’ve done a free email every day for six years, right? Um, that that’s built a business, but But you’re 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 system I have systems that make it easier. Is that the dad or Both, both. You you 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 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 nine on Daily Dad that are ready to record and eight that are recorded but not scheduled. So like And that’s your system? Yeah, so I I’m just doing 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 three 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.
Sam Parr: Are you uh writing the scripts to your YouTube videos? I think you’re only doing one or two a week, right?
Ryan Holiday: Yes. Uh so YouTube uh I have a I have a I have a actually wait, let me I’ll come back to that in a second. The other thing I would say about the people who are like, oh, I really want to get to quality, that’s why I take 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 five years and I’m like, where? Show show me five years of work in this thing, right? I’m I’m not arguing with you that it it transpired over five years, but I don’t think you showed up and worked on this as you said, like a job every day for five years. I think it either it 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 Green or Robert Caro or you know, one of these greats, I’m like, I see the I see the five years. Like it’s obvious. Like you were like Robert Green was telling me the other day, he’s like seven 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 Green and um the uh what’s his uh what’s Caro’s book, Moses? Um 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 1500 or 1300 word like epic. And then and pretty much like Titan is like this too. Anything Ron Chernow does. Yes. Every sentence have like to me, it’s like a life’s work and if they’re lucky, they can maybe get three 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 it 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.
Ryan Holiday: 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 uh the 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 stage those those sentences. So yeah, like there’s definitely people who there’s a reason they only do two or three 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 uh meditations on a larger idea. But if it is a like, you know, how to read Marcus Aurelius, how to read Seneca, um 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.
Sam Parr: Are you using Google Docs?
Ryan Holiday: Yeah, for the for the most part, yeah.
Sam Parr: And how big’s the team?
Ryan Holiday: Uh like 10 people now, probably. And that includes that includes the bookstore.
Sam Parr: And also does it include Daily Stoic and uh uh Daily Dad?
Ryan Holiday: Yeah, yeah. I’m saying I probably have 10 employees, maybe maybe 11 or 12, but but less than 15.
Sam Parr: Dude, that is crazy, man. The output is just awesome. I I I think that’s amazing.
Sam Parr: Our software is 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.
Sam Parr: 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 I 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. 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 have you looked into these Book of the Month businesses? I think Reese Witherspoon had one too that I think was profitable.
Ryan Holiday: 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 because 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 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. Um 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.
Sam Parr: How much revenue can you make on one send?
Ryan Holiday: Uh from from the reading list newsletter? I don’t know. Um I don’t know. Uh I actually 10 or 20 grand maybe. Yeah, that that would be that would be a 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 want to 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 who’s my high or my 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 uh like complaining to me. He’s 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 it’s right, it’s the same thing we’re 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 I 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 I got some early shares in Vinyl Me when it came out. So and that’s been a surprisingly big business. Like I 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 a thousand 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? Like 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 I think with a book, like people have so little room to read in their lives that I 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.
Sam Parr: 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?
Ryan Holiday: 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. 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 want to say he’s a regular person because that sounds like 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 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 like fundamentally 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, 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 want to be world class at what I do and and like be a somewhat of a normal person. Like it’s almost easier to be great than it is to be good, if that makes sense.
Sam Parr: Yeah, that’s awesome. Who who who else have you uh who have you met? So I 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 kind of yeah, maybe normal’s insulting, but like that’s what it I was like, you’re a I’m never going to be 7 ft tall, but like, you know, like your mentality is achievable. You know what I mean? Well, it’s It’s kind of funny as 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 it I 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 three-pointer to win 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 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 want to say who it is. I not because I it not because I it I feel weird uh dropping the name. But anyways, let’s just say I met this musician and he’d read the books and he reached out to me to 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 going to 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 a 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 What? 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? 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 weeks here in the Hamptons. And it it it was like um again, I think at the end of your life and you 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 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 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 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 you like spending time together. Dude, so many people so the hustle we were a daily email and then me and Sean do this thing three days a week and people are like, hey, how are you doing quantity? I want to 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 you know, you like the the output here or like the if this were a 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 think 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 a book or something. So I like I I’ve done a free email every day for six years, right? Um, that that’s built a business, but But you’re 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 system I have systems that make it easier. Is that the dad or Both, both. You you 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 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 nine on Daily Dad that are ready to record and eight that are recorded but not scheduled. So like And that’s your system? Yeah, so I I’m just doing 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 three 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.
Sam Parr: Are you uh writing the scripts to your YouTube videos? I think you’re only doing one or two a week, right?
Ryan Holiday: Yes. Uh so YouTube uh I have a I have a I have a actually wait, let me I’ll come back to that in a second. The other thing I would say about the people who are like, oh, I really want to get to quality, that’s why I take 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 five years and I’m like, where? Show show me five years of work in this thing, right? I’m I’m not arguing with you that it it transpired over five years, but I don’t think you showed up and worked on this as you said, like a job every day for five years. I think it either it 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 Green or Robert Caro or you know, one of these greats, I’m like, I see the I see the five years. Like it’s obvious. Like you were like Robert Green was telling me the other day, he’s like seven 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 Green and um the uh what’s his uh what’s Caro’s book, Moses? Um 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 1500 or 1300 word like epic. And then and pretty much like Titan is like this too. Anything Ron Chernow does. Yes. Every sentence have like to me, it’s like a life’s work and if they’re lucky, they can maybe get three 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 it 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.
Ryan Holiday: 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 uh the 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 stage those those sentences. So yeah, like there’s definitely people who there’s a reason they only do two or three 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 uh meditations on a larger idea. But if it is a like, you know, how to read Marcus Aurelius, how to read Seneca, um 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.
Sam Parr: Are you using Google Docs?
Ryan Holiday: Yeah, for the for the most part, yeah.
Sam Parr: And how big’s the team?
Ryan Holiday: Uh like 10 people now, probably. And that includes that includes the bookstore.
Sam Parr: And also does it include Daily Stoic and uh uh Daily Dad?
Ryan Holiday: Yeah, yeah. I’m saying I probably have 10 employees, maybe maybe 11 or 12, but but less than 15.
Sam Parr: Dude, that is crazy, man. The output is just awesome. I I I think that’s amazing.
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Sam Parr: 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 I 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. 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 have you looked into these Book of the Month businesses? I think Reese Witherspoon had one too that I think was profitable.
Ryan Holiday: 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 because 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 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. Um 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.
Sam Parr: How much revenue can you make on one send?
Ryan Holiday: Uh from from the reading list newsletter? I don’t know. Um I don’t know. Uh I actually 10 or 20 grand maybe. Yeah, that that would be that would be a 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 want to 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 who’s my high or my 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 uh like complaining to me. He’s 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 it’s right, it’s the same thing we’re 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 I 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 I got some early shares in Vinyl Me when it came out. So and that’s been a surprisingly big business. Like I 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 a thousand 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? Like 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 I think with a book, like people have so little room to read in their lives that I 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.
Sam Parr: 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?
Ryan Holiday: 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. 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 want to say he’s a regular person because that sounds like 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 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 like fundamentally 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, 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 want to be world class at what I do and and like be a somewhat of a normal person. Like it’s almost easier to be great than it is to be good, if that makes sense.
Sam Parr: Yeah, that’s awesome. Who who who else have you uh who have you met? So I 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 kind of yeah, maybe normal’s insulting, but like that’s what it I was like, you’re a I’m never going to be 7 ft tall, but like, you know, like your mentality is achievable. You know what I mean? Well, it’s It’s kind of funny as 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 it I 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 three-pointer to win 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 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 want to say who it is. I not because I it not because I it I feel weird uh dropping the name. But anyways, let’s just say I met this musician and he’d read the books and he reached out to me to 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 going to 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 a 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 What? 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? 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 weeks here in the Hamptons. And it it it was like um again, I think at the end of your life and you 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 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 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 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 you like spending time together. Dude, so many people so the hustle we were a daily email and then me and Sean do this thing three days a week and people are like, hey, how are you doing quantity? I want to 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 you know, you like the the output here or like the if this were a 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 think 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 a book or something. So I like I I’ve done a free email every day for six years, right? Um, that that’s built a business, but But you’re 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 system I have systems that make it easier. Is that the dad or Both, both. You you 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 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 nine on Daily Dad that are ready to record and eight that are recorded but not scheduled. So like And that’s your system? Yeah, so I I’m just doing 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 three 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.
Sam Parr: Are you uh writing the scripts to your YouTube videos? I think you’re only doing one or two a week, right?
Ryan Holiday: Yes. Uh so YouTube uh I have a I have a I have a actually wait, let me I’ll come back to that in a second. The other thing I would say about the people who are like, oh, I really want to get to quality, that’s why I take 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 five years and I’m like, where? Show show me five years of work in this thing, right? I’m I’m not arguing with you that it it transpired over five years, but I don’t think you showed up and worked on this as you said, like a job every day for five years. I think it either it 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 Green or Robert Caro or you know, one of these greats, I’m like, I see the I see the five years. Like it’s obvious. Like you were like Robert Green was telling me the other day, he’s like seven 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 Green and um the uh what’s his uh what’s Caro’s book, Moses? Um 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 1500 or 1300 word like epic. And then and pretty much like Titan is like this too. Anything Ron Chernow does. Yes. Every sentence have like to me, it’s like a life’s work and if they’re lucky, they can maybe get three 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 it 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.
Ryan Holiday: 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 uh the 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 stage those those sentences. So yeah, like there’s definitely people who there’s a reason they only do two or three 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 uh meditations on a larger idea. But if it is a like, you know, how to read Marcus Aurelius, how to read Seneca, um 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.
Sam Parr: Are you using Google Docs?
Ryan Holiday: Yeah, for the for the most part, yeah.
Sam Parr: And how big’s the team?
Ryan Holiday: Uh like 10 people now, probably. And that includes that includes the bookstore.
Sam Parr: And also does it include Daily Stoic and uh uh Daily Dad?
Ryan Holiday: Yeah, yeah. I’m saying I probably have 10 employees, maybe maybe 11 or 12, but but less than 15.
Sam Parr: Dude, that is crazy, man. The output is just awesome. I I I think that’s amazing.
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Sam Parr: 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 I 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. 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 have you looked into these Book of the Month businesses? I think Reese Witherspoon had one too that I think was profitable.
Ryan Holiday: 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 because 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 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. Um 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.
Sam Parr: How much revenue can you make on one send?
Ryan Holiday: Uh from from the reading list newsletter? I don’t know. Um I don’t know. Uh I actually 10 or 20 grand maybe. Yeah, that that would be that would be a 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 want to 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 who’s my high or my 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 uh like complaining to me. He’s 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 it’s right, it’s the same thing we’re 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 I 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 I got some early shares in Vinyl Me when it came out. So and that’s been a surprisingly big business. Like I 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 a thousand 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? Like 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 I think with a book, like people have so little room to read in their lives that I 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.
Sam Parr: 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?
Ryan Holiday: 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. 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 want to say he’s a regular person because that sounds like 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 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 like fundamentally 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, 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 want to be world class at what I do and and like be a somewhat of a normal person. Like it’s almost easier to be great than it is to be good, if that makes sense.
Sam Parr: Yeah, that’s awesome. Who who who else have you uh who have you met? So I 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 kind of yeah, maybe normal’s insulting, but like that’s what it I was like, you’re a I’m never going to be 7 ft tall, but like, you know, like your mentality is achievable. You know what I mean? Well, it’s It’s kind of funny as 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 it I 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 three-pointer to win 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 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 want to say who it is. I not because I it not because I it I feel weird uh dropping the name. But anyways, let’s just say I met this musician and he’d read the books and he reached out to me to 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 going to 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 a 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 What? 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? 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 weeks here in the Hamptons. And it it it was like um again, I think at the end of your life and you 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 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 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 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 you like spending time together. Dude, so many people so the hustle we were a daily email and then me and Sean do this thing three days a week and people are like, hey, how are you doing quantity? I want to 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 you know, you like the the output here or like the if this were a 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 think 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 a book or something. So I like I I’ve done a free email every day for six years, right? Um, that that’s built a business, but But you’re 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 system I have systems that make it easier. Is that the dad or Both, both. You you 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 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 nine on Daily Dad that are ready to record and eight that are recorded but not scheduled. So like And that’s your system? Yeah, so I I’m just doing 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 three 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.
Sam Parr: Are you uh writing the scripts to your YouTube videos? I think you’re only doing one or two a week, right?
Ryan Holiday: Yes. Uh so YouTube uh I have a I have a I have a actually wait, let me I’ll come back to that in a second. The other thing I would say about the people who are like, oh, I really want to get to quality, that’s why I take 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 five years and I’m like, where? Show show me five years of work in this thing, right? I’m I’m not arguing with you that it it transpired over five years, but I don’t think you showed up and worked on this as you said, like a job every day for five years. I think it either it 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 Green or Robert Caro or you know, one of these greats, I’m like, I see the I see the five years. Like it’s obvious. Like you were like Robert Green was telling me the other day, he’s like seven 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 Green and um the uh what’s his uh what’s Caro’s book, Moses? Um 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 1500 or 1300 word like epic. And then and pretty much like Titan is like this too. Anything Ron Chernow does. Yes. Every sentence have like to me, it’s like a life’s work and if they’re lucky, they can maybe get three 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