#1108 Ryan Holiday On How To Get Rich Writing Books

Ryan Holiday is a NYT best selling author, podcaster & content creator who just released a new book "Discipline Is Destiny". In this conversation, we discuss the business behind the best selling books, choosing which content to post, taking risks, building a team, Ryan's writing process, the discipline he applies to his own life, and personal ambitions. ======================= Compass Mining is the world's first online marketplace for bitcoin mining hardware and hosting. Compass was founded with the goal of making it easy for everyone to mine bitcoin. Visit https://compassmining.io/ to start mining bitcoin today! ======================= Exodus is leading the world out of the traditional financial system by building beautiful and user-friendly blockchain products. With its focus on design and user experience, Exodus has become one of the most popular and loved cryptocurrency apps. It’s supported on both desktop and mobile, allowing you to sync your wallet across multiple devices so you can have access to your funds anywhere. You can instantly exchange around 100 different cryptocurrencies straight from your wallet. Interactive charts let you view an asset’s price history and your portfolio’s performance over time. And maybe the best part, Exodus is integrated with the Trezor hardware wallet - making advanced security easy for everyone. Visit exodus.com/pomp for your free download or search Exodus on the App Store or Playstore. ======================= LMAX Digital - the market-leading solution for institutional crypto trading & custodial services - offers clients a regulated, transparent and secure trading environment, together with the deepest pool of crypto liquidity. LMAX Digital is also a primary price discovery venue, streaming real-time market data to the industry’s leading analytics platforms. LMAX Digital - secure, liquid, trusted. Learn more at LMAXdigital.com/pomp ======================= Amberdata provides the critical data infrastructure enabling financial institutions to participate in the digital asset class. We deliver comprehensive data and insights into blockchain networks, crypto markets, and decentralized finance. Download our Digital Asset Data Guide at https://www.amberdata.io/pomp ======================= Bullish is a powerful new exchange for digital assets that offers deep liquidity, automated market making, and industry-leading security. Combining the innovations of DeFi with the regulated environment of traditional finance, Bullish empowers users to trade with certainty and earn passively at scale across variable market conditions, in an environment backed by multibillion-dollar liquidity contributions from the Bullish Treasury. Visit bullish.com/pomp today to learn more. Note: Bullish is licensed by the Gibraltar Financial Services Commission. Virtual assets and related products are high risk. Consult your investment advisor and trade responsibly. Bullish is available in select locations only and not to U. S persons. Visit bullish.com/legal for important information and risk warnings. ======================= The number one name in NFT domains and the world’s most powerful wallet are teaming up to bring something new to the crypto and Web3 world: That’s right, Unstoppable Domains and Blockchain.com partnered to create NFT domain names ending in . Blockchain. It’s the perfect ending to show that you’re a believer in a decentralized future. Either sign up for a free blockchain.wallet or visit Unstoppabledomains.com to buy your domain today.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:02Anthony Pompliano?

  What's up everyone? This is Anthony Pompliano. Most of you know me as Pomp. You're listening to the Pomp Podcast, simply the best podcast out there. Now let's kick this thing off. Ryan Holiday is a New York Times bestseller, including his brand new book, Discipline is Destiny, which is part of a four book series on the Stoics and the Stoicism philosophy. I really enjoyed this conversation with Ryan. We covered a whole bunch, including his book launch, how he thinks about the Stoics, why he has reinvented himself so many different times, what the importance of the apprenticeships that he's went through his life are, what he thinks about being a parent in the intersection with Stoics, and also how he thinks about death driving focus, and much, much more. I really enjoyed this conversation with Ryan. I hope

• 0:46Anthony Pompliano?

  you guys enjoy it as well. Once you get done listening, let us know on Twitter or your favorite social platform, what you agreed with and what you didn't agree with. We'd love to hear your feedback. All right, let's get into this episode with Ryan. I hope you guys enjoy it.

• 0:57Speaker 01

  Anthony Pompliano runs Pomp Investments. All views of him and the guests on his podcast are solely their opinions and do not reflect the opinions of Pomp Investments. You should not treat any opinion expressed by Pomp or his guests as a specific inducement to make a particular investment or follow a particular strategy, but only as an expression of his personal opinion. This podcast is for informational purposes only.

• 1:21Anthony Pompliano?

  All right, guys. Bang, bang. I've got Ryan here with me. Ryan, I thought a great place to start our conversation is this idea of reinvention. You've had what seems like many different milestones or paths in your career. And I wanted to know how you think about those paths or those different stops in your career. You've worked under different people. You've kind of had these different aspects. Why did you continue to reinvent yourself and how did you do it so successfully?

• 1:44Speaker 02

  Yeah, there's a, there's a quote I like that I'm forgetting the exact version of it, but it's basically that like, to become who you are, you have to kill off all these different selves, right? And I feel like that maybe when someone looks at my career, they think about it as being this sort of, well, he was this, and then he was this, and then he was this. I think about it more as I sort of started as this collection of things. I had all these different interests and I explored each one and I took them as far as they could go. But then either I hit a dead end or I stopped being interested in it and then that part of myself had to be killed off. And so I had a marketing career. I had an entrepreneurial career.

• 2:23Speaker 02

  I had a, you know, I've written about different topics, but I think it was all towards, I don't want to say a specialization, but it was, it was towards sort of picking that one sort of singular lane, which is what I write about now. So like, I guess I would just say that in retrospect, these things always look much clearer than they are. So like people, people go like, well, you were writing about marketing. How did you switch to writing about ancient philosophy? But the truth was I was writing about ancient philosophy first, then I sold a marketing book, which was successful and sort of outshined the other stuff. Then I went back to it.

• 3:03Speaker 02

  So my, my point is that you want to be careful, I think, looking at someone's career and going like, well, they obviously went from this to this to this. It, that, that clarity, I think, tends to reveal itself only in the biography, if you know what I mean.

• 3:19Anthony Pompliano?

  Makes complete sense. One of my favorite questions to ask people who are on the internet in, you know, many different facets is, do you consider yourself an author, a creator, an entrepreneur, or something else? Like, if you have to pick one identity or one way that you think about your life, what are you?

• 3:34Speaker 02

  Well, I like the term creator and it seems it's new ish, right? Like, I think when I was starting even 10, 15 years ago, there, you, there was writers, authors, filmmakers, et cetera, the idea that you would, you would have to be multidisciplinary, that you would have to have skills in all these different mediums that didn't exist. So I do like the idea of, of a creator and, and that's what I think I would tell someone to aspire to be, as opposed to just picking one thing. But I, I love books and so I see myself as a writer. And, and even the distinction between author, writer, to me, author tends to only be books. So I, I identify as a writer, like, and I, and when you look at the other stuff that I do, whether it's on

• 4:20Speaker 02

  On the podcast or YouTube or social media, it to me, it's all fruit of the writing. If I don't do the writing, if I'm not doing like sort of focused creative work in the written word, none of the other stuff happens. You have to have like a core competency, you know what I mean? I think the problem with being a creator is people think is this kind of like loose thing like, oh, I'm an artist, I just make stuff. And that that is part of it, but you you have to have like a core competency. It's like to be in the MMA or to be a professional MMA fighter, you have to have one facet of your game that you're like the best at. You have to be proficient in all the other domains.

• 5:04Speaker 02

  But if you're not like, you don't have a ground game or you're not a stand up guy or kickboxing guy, like you're probably going to get your ass kicked.

• 5:11Anthony Pompliano?

  Yeah, it's fascinating to hear you say this. Jerry Seinfeld on a episode with Tim Ferriss talked about how comedy is really a writing exercise. And I feel like so much of the content that gets created, maybe outside of just live interviews and podcast form, pretty much everything else seems to be a writing exercise. And so do you feel like if you had to pick one of the skills to be great at, writing is probably the thing that allows everything else to kind of really spruce up from?

• 5:35Speaker 02

  I I I do, I think great writing translates in all the different mediums. So like if I write an article or a chapter in a book or a concept in a book and it resonates, what I then do is go, okay, well, what's the video version of this? What's the tweet version of this? You know, what's the Instagram carousel version of this? I look to translate it in those different mediums. But it has to first come from like my preferred creative methodology or medium. I don't know if I would necessarily choose writing. I would say writing chose me like that. That's where I'm most comfortable. That's that's what that that's how I express myself as a human being.

• 6:18Speaker 02

  You know, maybe somebody else for them first it starts with something else. I don't know. I just know that if you can really nail something in one medium or one format and the core idea. Or concept is good, it can be pretty easily translated. Like in traditional publishing, for instance, like I write a book and then it gets translated into different languages. It the the rights get sold to a Ukrainian publisher or a a Mandarin publisher or all these different markets. I don't even see those books, but they know if it works in English, chances are it's going to work in India, it's going to work in all these different markets.

• 6:59Speaker 02

  So that's kind of now how I've come to think about social media stuff is is like TikTok is not a medium that I get particularly excited about consuming content, but I try, I have people on my team who help me take what's worked, say, in one of my books. And then how do we, how do we break that down so it has the ability to take advantage of the algorithm on TikTok?

• 7:25Anthony Pompliano?

  So what's interesting about this is if you were creating just YouTube videos or other types of digital content, you could go into the analytics, you could see where are people listening the most, what does it seem like people are dropping off and be very data driven about it. With a book, sure, there's digital versions, but for the most part, the physical book, you have no data. So how do you actually go and figure out what are the things that we should take out of a book or out of a blog post and turn it into a video or TikTok or any other format?

• 7:51Speaker 02

  There is some data, I remember Tim Ferriss turned me on to this, you can pull up like in on Kindle, what the most highlighted passages of a book are, or what's the quotes that get shared the most. I I often look at like, what are the pages that people share? So like, for for instance, The Daily Stoic, it's one page a day. So people often post like the pages of the books that they like. So the book is seven years old now. We have a sense of what the pages that people like the most, what entries get shared the most. And so that's that that is valuable data. But, um, yeah, I think maybe one of the things that I love about writing books is that

• 8:35Speaker 02

  you're, you're on a longer time span and a less sort of.

• 8:45Speaker 02

  I don't even know what the word is, but it's not so data-driven. And that allows you to think bigger picture. And I think when I'm writing a book, I'm trying to write a book that will still be relevant in 10 years or in 15 years. I think when people are tweeting, they're thinking about what's trending right now. And that's why so much of what's on social media is ephemeral and doesn't age very well. You know, there's that expression aged like milk. I think a lot of social media ages prematurely because people are trying to ride whatever the wave of the moment is, as opposed to trying to get to something that truly connects with, you know, people on a fundamentally human level.

• 9:28Anthony Pompliano?

  You've got a team, I've heard you say somewhere around 10 people or so. What do those people do, right? Like when somebody sees a book come out, how much of the team was helping on research or other things? And then how much of the team is focused on maybe after the book is published, what you're doing on social media or other parts of your business?

• 9:42Speaker 02

  Yeah, so I have, and obviously an editor at my publisher. I have my own editor that I work with. So that would be, you know, that's on the creative content side. I have a research assistant who helps me gather the stuff. But the writing, I would say, is the most solitary of what I do. That's what's coming from inside me, what I'm interested in. It's the things that can't, it's the one part of it that really can't be outsourced or scaled in any way. That's the unique creative expression. In the same way that, you know, for a musician, like you gotta go to the studio and write what you want to talk about. And then everything else, to me, is about scaling and translating and stretching that

• 10:26Speaker 02

  material to meet as big a market as possible. So obviously I have people on the social team, I have people on the video team, I've got people, like I do this daily email. So how does that email actually get set up and formatted and then, you know, sent out? I've got editors that do the audio side of the stuff on the podcast and the daily email as well. So most of the team that I set up is about sort of taking that singular creative act and allowing me to scale it into as many different avenues as possible.

• 11:03Anthony Pompliano?

  So I used to always think that the creative work was going to be the last thing that machines could replace, right? This idea that it would go after all of the rope memorization, it would go after all the tedious stuff. And if you were creative, you had this like moat that a machine could never come after. And I was talking to Billy recently, who I know works with you. And he said, you know, I've never heard Ryan talk about artificial intelligence. And obviously, with the rise of all the image generation and kind of all this stuff that now seems like, wait, maybe the machines are pretty good at the creative work. How do you think about the intersection between artificial intelligence, machines and writing? Like, if it's so solitary, it's so creative for you, could it one day replace humans? Or how do you think about that?

• 11:41Speaker 02

  You know, I have this weird experience with artificial intelligence, which is one of the things that I do. It's sort of a creative sort of practice is whenever I read a book, so like, I go through them and I take notes based on the stuff that I like. And then I usually go and I'm either writing those down by hand on note cards, which is, you know, what I use for my research. But sometimes I'll type it out because I want to print up the quotes like too long for me to do by hand. So I'll type it up. And sometimes I just type it in Gmail. And you know, when you're using Gmail, it tries to suggest to you where it thinks you're going with that sentence with, with, with artificial intelligence. Now, when, when you're writing an email to you and your friends and you're like, hey, do you want to get together tomorrow?

• 12:26Speaker 02

  It's like evening, right? It's, it's pretty good at guessing where you're going to go. You know, it says like, thanks for your time. You know, it gets the sort of cliches or the, the basic ins and outs of language, which is, it's kind of remarkable and a little bit creepy. And, and it does save you a little bit of time. But I've found as I type these quotes, and I've typed out, you know, quotes from Hemingway and Fitzgerald and all the great writers in history, it is never guessed the end of a truly great sentence. Right? And so maybe I'm deluding myself, but my view would be it can, it can get sort of humdrum basics, just in the way that it can guess, okay, you sent me an email about getting together. Google can tell me

• 13:11Speaker 02

  whether it can ask. Whether I want to add that to my calendar or not, but can it actually create a truly unique, profound insight about the human experience? I have yet to see that. And, and I, you know, maybe it can at some point. And, and obviously as, as creators, that, that's going to be an alarming, you know, sort of moment. But, but I do think what, what that would do is just force us as human beings. I think a lot of what we do tend to talk about is pretty basic and not that interesting. I think it's going to force us to actually have to get more vulnerable, get, you know,

• 13:54Speaker 02

  better in touch with ourselves, you know, be more fearless with what we write. Like it's, it's just going to force us to go to the things that the machine can't nail, which is like sort of who we truly are and what we truly think about.

• 14:10Anthony Pompliano?

  It, it's interesting that you're saying it this way because I saw someone on Twitter talking about the fact that people who aren't actually artistic now can simply become artists using some of these image generators and things like that. And it puts a higher value on ideas, like the, the old saying of, you know, ideas are worthless, it's all about execution. For an artist, it used to be like, you can have all the ideas, but like, can you paint? Can you actually create this? Now, if you can just simply type in an idea, it may be able to do the execution for you, which kind of changes the relationship between ideas, execution, you know, creative work, and how people have thought about where the value lies.

• 14:43Speaker 02

  No, I think that's right, although I've always argued that while execution is certainly important, brilliant execution without a good idea is essentially worthless. You know, like the, the, the core thing to, to make it as a writer is not, you know, how good you are at marketing, although if you're bad at marketing, you're probably not going to make it as a writer. The core thing is not how beautifully you can string words or sentences together. The core thing is, do you fucking have something to say? Right? And do you have something to say that people haven't heard before? Or that, that, that does something for people? This is ultimately.

• 15:22Speaker 02

  The competitive advantage. And so I'm not sure it's necessarily new, but I think I would agree with the idea that it makes it harder. Like Tyler Cowen wrote a book several years ago called Average is Over. I think what these tools do is perpetuate that idea, which is that it becomes increasingly difficult to make it being mediocre, being pretty good, being okay, right? Having something not particularly unique to say, I think all these platforms get more and more competitive. Or conversely, there's fewer and fewer spots because artificial intelligence is doing the basic stuff, just like,

• 16:03Speaker 02

  like, look, you used to be able to make a living carrying boxes, but now a forklift can do that. And now a robotic forklift can do that. You have to be able to solve complex problems in a way that a computer can't to to to sort of get one of those jobs. And I wouldn't be surprised if you see that shift even in the creative fields.

• 16:22Anthony Pompliano?

  Yeah, it makes complete sense. In Robert Greene's book Mastery, he talks a lot about apprenticeship. And I feel like part of your success has been spending the time to actually do the apprenticeship. And you may have thought about it that way, or maybe you didn't think of it. When I spoke with Robert, one of the things he said about you was that you and him had talked multiple times that you wanted to go write books. And was it the right time? Should you wait? You know, what was the pros and cons of now versus later? How do you think in hindsight about the apprenticeships that you got with Robert and others? And how important was that for you to kind of have the skill set and experience to be able to be so successful as an author today?

• 16:58Speaker 02

  Yeah, I mean, I don't think I'd be talking to you without my time working for Robert. In fact, I almost certainly wouldn't. And I think you said hindsight there. This is another thing where hindsight creates the clarity, right? Like, in retrospect, I was Robert Greene's apprentice because we don't live in the 1700s. And my father didn't sell me to Robert Greene as an apprentice, you know, in exchange for room and board. These apprenticeships or these mentorships, you know, I think people hear about them and they go, okay, I need to go find a mentor. They go, hey, will you be my mentor? That's not. Not how it works, right? Just like you, you, you start spending time with someone and then eventually go, hey, what is this?

• 17:40Speaker 02

  Are we like boyfriend and girlfriend or you know, what is this? That becomes clear after. And so, you know, I started for Robert transcribing interviews that he was doing. A thing that you wouldn't to go to what we were just talking about. That's a thing you would not hire a person to do these days, right? Either the writer does it themselves because they need to engage with the material, which I hear a lot from a lot of creators about. Or now you can do have software do it for you. That's it's almost indistinguishable. But at that time I did it. So I started just transcribing these interviews. And, and then that blossomed into more of, you know, occasionally I would ask Robert questions and then he assigned me to go research things. And, and over, you know, five or six years, I basically learned not just

• 18:25Speaker 02

  what a, a writer does and, and, and what a writer, you know, what the writing life looks like. But I actually learned like the craft of writing a book from start to finish. And, you know, I remember Robert would often go like, hey, you know, you have to submit your hours to me. Like, so I can pay you. And I was, I'd be like, yeah, I've, I've not been recording them at all. I don't, I don't. Obviously I need money, but like to me that the payment here is that I want to learn how to do what you do. And the fact that you are occasionally answering my questions is the payment that, you know, I, I was, I was ultimately after. And, and I think like one way to think about this is like,

• 19:10Speaker 02

  there are people whose time you could not purchase, right? Like their time is simply not for sale. And so working for them, yeah, you might be making $20 an hour or whatever the sort of starting wage is for them. But what you're really getting is access into their world, into how they think, into the kind of advice that, you know, a billionaire couldn't purchase. And I, I think ultimately that's what I got from Robert is a sense of like how an idea becomes a thing. And, and how, you know, Has to approach the craft, think about the craft, commit to the craft. And I feel like I'm still, I'm, I'm, I'm still in some version of that apprenticeship with him today.

• 19:55Speaker 02

  Although like at some point, he basically had to say like, I'm not going to give you research tasks anymore. Uh, I'm going to give them to other people. I, I would still, I would still do it on the side like if I could, because I, I just learned so much. And I mean, often like, I'm still using things in my books today that I, that he had me tracked down. Like, uh, you could say some of my books are like B sides to Robert's books, because there are things that I found and I was like, Robert, I think this is cool. And he's like, no, that's not, that's not for me. And I was like, well, I'm going to keep it and use it. And so I, I, I think it's really important, like whatever it is that you're trying to do. You find someone who is world class at that thing.

• 20:35Speaker 02

  And it doesn't matter if you're getting them coffee or sweeping the floors or, you know, driving them around. You need to be in that orbit and, and learn by osmosis, most of all, how, how they do what they do.

• 20:49Anthony Pompliano?

  It reminds me of the Warren Buffett quote, I think he says something paraphrased around, uh, somebody asked for a job and they said they would work for free, but that was too expensive for me. And it's all about like the time investment, right? Ends up actually being way more expensive than any money he could have spent. But one of the things that Robert said to me, uh, is the only negative thing that he said about you. Uh, in the, in the full conversation, he said, uh, Ryan violated one of the 48 laws of power. He now outshines the master, which it is interesting, right? Like the hope, I think of every mentor or coach is that eventually they do teach people, whether implicitly or explicitly. Uh, and they go on and they're successful. And so how do you think about, uh, taking the things that you learned from Robert and, and other, uh, maybe apprenticeships that you had?

• 21:32Anthony Pompliano?

  And like almost helping the people who work with you now and really cheering them on and hoping that they end up being even more successful than you.

• 21:40Speaker 02

  Yeah, I mean, that is the first law of power, never outshine the master. And and it's true. You you have to be cognizant of the fact that every single human being has pride and ego, that we have this sense of a hierarchy of how the world works. I think it's it's to Robert's credit for for for a guy who who wrote a book that starts with never outshine the master. And then there's another law of power, an equally great one about letting others do the work and and taking all the credit. He has been an incredible cheerleader of my work and supporter. I remember Robert referred me to his agent, who promptly turned me down. But but but Robert has always opened doors for me and been and been awesome.

• 22:22Speaker 02

  I think he's being falsely modest when he's saying that I I've I've outshined him because I I know how many books Robert has sold and and I will have to be alive for a very long time to even come remotely close to that. But I think he and I have had a great relationship in that, like, Robert has showed me how sort of traditional publishing works, how the craft of things works. And then on my end, as I've as I've figured out different marketing things, every once in a while, like, you know, a couple of times a year, he and I get get together and I go, Robert, here's what you need to be doing on your end because your material is going to crush. So like with Daily Stoic, for instance, like, we had a lot of success with Instagram reels

• 23:06Speaker 02

  and TikTok, like we were talking earlier. And so I set Robert Green up with like a a social media manager and a video person that every day cuts up clips like from the 25 years of of interviews that Robert's done over the years and they post one a day. And every time I pull up Instagram, I'm like, Jesus Christ, did did this video of Robert do a million and a half views today? You know, his stuff is so good that for for Robert, it's really about just the same thing that I'm doing, but but he has this immense, you know, decades of of backlog. And I think you're seeing, you know, Robert's books have never sold better than they're selling this year. And I think

• 23:49Speaker 02

  That's a testament to what happens when you make truly great shit. All you really need to do is occasionally, you know, update and tweak and turn the dial as far as like the distribution mechanism for that work. And it's always going to be relevant. And, uh, you know, I think, I think it's, it's pretty amazing just to see like how big, uh, Robert is like even in 2022.

• 24:13Anthony Pompliano?

  You've dissected the manipulation of the media previously, uh, and more so from, uh, could you feed stories to the media and they kind of run wild with it and use their incentives against them. But in some way, what you're talking about here is using social media to manipulate the audience in terms of interest, right? It is a form of media manipulation. You're not trying to trick someone at the New York Times or some kind of mainstream publication. But in some way, I almost feel like maybe the algorithm is the publisher or the, uh, kind of content gate. And if you're able to put the right content in front, you see authors becoming very popular. My wife, uh, has been telling me about a woman, Colleen Hoover, who's got like six of the top 10 books in the world.

• 24:49Speaker 02

  She's the biggest author in the world.

• 24:50Anthony Pompliano?

  Yeah. And supposedly it was all because of TikTok. She like became viral on TikTok and now she, uh, has all these books. And so how do you think about the overlay of maybe like old school media manipulation and the things you've written about there with like this social media game and the algorithm almost being a gatekeeper in some way?

• 25:05Speaker 02

  So like in, in publishing even 10 years ago, right? It was bookstores were the gatekeepers or the mechanism by which, you know, most books were discovered, right? There's, there's some traditional PR still at that point, but like, you know, you would walk into an airport and there'd be the section of books that are, you know, sort of new and noteworthy. And that was a paid game. Like anytime you walk into a bookstore and you see books that are face out, this is like at a Barnes and Noble or an airport or whatever. Those books, that, that, that space, that, uh, that, that promotional platform is purchased. It's called co-op. And so to break through as an author, you needed a publisher and you needed a pretty large marketing budget

• 25:46Speaker 02

  to get you in front of people. And then you think about actually how small an audience you're competing for there, right? Like how many people walk into bookstores in America on any given day? I don't know. 500,000? People a million, that's probably high, but you're competing for those eyeballs and a certain percentage of them already know what they want, or they're not interested in what you're doing. So it's, it is a very small pie that a lot of people are competing for. Now, you, you can, you contrast that with social media, you know, however, many millions of people are on TikTok or Instagram or Facebook or Twitter at any given moment. And the vast majority of them are not in, don't even know that they're interested in books,

• 26:28Speaker 02

  but, but they potentially could be. And so what I think about with my stuff or other authors I work with or Roberts, is I, I try to think, okay, I wrote this book. I think this book would be interesting to people who want to read books. But how do I take the core ideas in there and break it, it down into a piece of content, whether it's 10 seconds or 30 seconds or 30 minutes in a way that, that uses these algorithms, which are the most, you know, sort of powerful media or cultural forces on the planet. And how do I, how do I get them to work for me? Right? Um, I think about this, this is a very simple one, right? It's like the reason we're doing a video version of this podcast is that podcasts have huge audiences, right?

• 27:12Speaker 02

  But there's really no algorithm working on the podcast medium, right? You have your subscribers, you put it out, and if people subscribe, they hear about it. If they don't, you know, they don't, right? The only thing that can drive new followers to a podcast is word of mouth. People go, hey, I love this show. You should listen to it. But on YouTube, you have an incredibly powerful algorithm coupled with the second largest search engine in the world. And so the, you know, by, by doing a video version of it, or breaking that video, you know, the, the hour and a half or two hours we're doing into clips, you now put yourself into a position where YouTube is driving significant discovery of your content.

• 27:56Speaker 02

  And so I just think a lot about how do I, how do I make the algorithm do the hardest thing in the world for a creator, which is surface your stuff to people who have not heard of you.

• 28:11Anthony Pompliano?

  I think everyone who's created content on the internet for long periods of time, you understand when you've kind of achieved an unlock, right? You either learn something or you realize there's a part of the algorithm that you're able to exploit in some way. And when you do that, it almost feels like you've leveled up to some degree. But what I always find interesting is that there's always new platforms and part of actually understanding where to create content is selecting the platforms to double down on and then the platforms to avoid on. And I'm sure you and I, we've got a bunch of mutual friends who will text you or call you and be like, there's this new platform. It's amazing. It's going to disrupt Twitter. And I'm always like, maybe. How do you think about which platforms you guys actually focus on versus maybe the ones

• 28:53Anthony Pompliano?

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• 30:12Speaker 02

  Yeah, there's definitely a first mover advantage on a lot of these platforms, but I would imagine that the people who are sort of serial first movers, I imagine a lot of those gains are washed out on the handful of networks that they invested big in that didn't pan out, right? So like, I didn't do anything on Clubhouse and you know, Clubhouse sort of went like that, right? And so I think about not being, I got this from Tim Ferriss, I don't want to be first, I wanna, I'm happy to be later, I just want to be great on that medium. And so I think a lot of people are rushing to be first and part of the reason they're rushing to be first is that they've had trouble getting traction anywhere else.

• 30:57Speaker 02

  One of the benefits too of like having traction on, you know, Instagram is that when a new platform comes, you tell people to follow you on that platform and you're not starting from zero on the other networks either. So I tend not to try to rush to be first at anything. I try to sort of step back, see how they operate, see what's working, what's not working, and then I go, okay, well, what is a medium that, or what's a form of content that I could do on that medium? So like, for instance, on podcasts, I was a little late to podcasts in the sense that, you know, I obviously I have been on podcasts since, you know, the very beginning, but,

• 31:37Speaker 02

  but I didn't launch mine until probably 2017 or 18, maybe even, maybe even a little bit later. But, but I had a big daily email, like the Daily Stoic is one email a day. And so as I thought about a podcast, I was like, you know what, I'm not going to do another interview podcast out of the gate. Why don't I just read the daily email and I'll have, you know, a one or two minute daily email podcast? And so that's how I started and, and I didn't start doing interviews until we were, you know, hundreds of thousands of downloads a month because we had this piece of content that we knew was already working. We already had a segment of our audience that was asking us to do a podcast and then

• 32:20Speaker 02

  we, we, we expanded into a new market from a position of strength as opposed to what I think a lot of people do, which is, you know, they start with nothing, really doing nothing, and then they just hope to get very lucky.

• 32:33Anthony Pompliano?

  What I find interesting about social media in opposition of books is books, as you mentioned, are supposed to be timeless, or at least the best ones end up being timeless. And so that takes a lot of thought. It takes a lot of editing. It takes a lot of concentration, focus, all the things we know that create this like really high quality work. But I also have this theory that like your dumbest tweets go viral. And it's the one that like you're taking a poop and you just fire it off and you don't even think about it. Next thing you know, you come back and you're like, holy shit. Like that was absolutely insane that that's the thing that goes viral. Where I see an intersection is that a lot of the content you upload to YouTube appears to be very high quality ideas, but it's almost like you're kind of like, I'm in my backyard or I'm like walking down the street. Like, like there's an element where I get the sense that you're almost trying to make it

• 33:18Anthony Pompliano?

  not super, super high quality, but the ideas themselves are high quality. Talk a little bit maybe about, you know, the intentionality of a book versus the, you know, serendipity of a viral tweet and then how you think about like the YouTube content and what you're actually trying to accomplish there.

• 33:32Speaker 02

  Yeah, I think, you know, a book might take a year or two years to write and you want it to last for five or 10 or 20 years or a hundred years, right? Like, I think people will be reading the 48 Laws of Power a hundred years from now. And so when you're writing a book, you're trying to write something perennial or classic. Well, and the expectation of the audience is significantly higher because they're paying for it. Right? And, and there's like literally thousands of years of history, setting the bar for what is good or not. So that's why I like starting with books because I know I'm making good stuff. And the medium is, is a very unforgiving medium. So I want to start there.

• 34:16Speaker 02

  And then, yeah, what I sit down and do, I use like, this is actually my, my GoPro rig, which is just, you know, a GoPro nine, I think, with an external mic and a tripod. I use other stuff, but like that, that can shoot in 4K video. So like, let's say I just spent two months, you know, writing a chunk of the book that I'm working on. Well, I've been thinking about that every day, workshopping it, kicking it. Around going over it with my editor, et cetera. Well, it's really not hard for me to sit down, you know, to set up the camera on a ledge somewhere, uh, stand a few feet back from it and then just talk about that thing for a minute or two minutes or five minutes.

• 34:57Speaker 02

  And then I can send that to my editor to break that down into, you know, the tightest version of it, you know, they can add some graphics or whatever. They could, they can then take this thing, make it seem even more spontaneous than it was and tighter than it actually was. And now I have, you know, a piece of video that the algorithm can take and, and put in front of hundreds of thousands of people, or in some cases, millions of people. So it's not that I'm trying to do necessarily lower quality stuff, but what I'm, I'm trying to take this thing that I have marinated on and meditated with for a significant amount of time. And then I'm trying to, to, to put it in a different format, really sort of quickly and authentically.

• 35:39Anthony Pompliano?

  Yeah, the, the other piece of this that, uh, resonates is you're actually offloading to some degree. You're coming up with the idea, you're the one talking about it. But there is an external or an outsourcing of, okay, how do I take that idea and make it like social media ready? And there's this editing component of it. And what's interesting, I think, is the different platforms started out almost in opposition to each other. So you had YouTube was super long form, you had Tik Tok, which was super short form. Instagram was photos. And because they're competing with each other, it almost feels like they're all converging on like 60 second or less vertical video. And so it changes the way somebody like you or me or others that we know create content because it's like, well, if all of you are going to incentivize and reward

• 36:24Anthony Pompliano?

  60 second or less vertical video, we can make it one time, put on all the platforms and like, we win to some degree. And so do you guys think about that at all?

• 36:32Speaker 02

  All the time. So, so like a great example is like, I can shoot a 60 second video. Uh, I can send it, I can have that edited for $10 or whatever, right? Or if I have a, you know, it's cost next to nothing. Costs nothing to shoot, costs nothing to edit. I can put it up, I, let's say I put it up on Tik Tok and it does a hundred thousand views. Okay. Now I know there's something here. Run that same video on Instagram as an Instagram reel. I have multiple accounts. I can run it on multiple accounts. I can also put that on Twitter as a short form video. I can put it on Facebook as a short term video. And then if, you know, let's say I've done that 10 times, I have 10 60 second videos.

• 37:13Speaker 02

  Or I actually, I just put up a video on Friday that was 60 Stoic lessons each in one minute or less. So that's like a 45 minute video. That is a compilation of all those, the, the short term ones that, that the algorithm was already pushing. And that'll probably do 100,000 views in and of itself. Now, and each one of these mediums monetizes itself differently. Each one of these mediums tends to have a different constituency. So you're putting your work in front of other people. I, I, I'm anywhere I'm getting double, triple, quadruple efficiencies for the same 60 seconds of time that I'm putting in. Man, like I'm, I'm all about that.

• 37:54Anthony Pompliano?

  Which platform are you the biggest on? Is it Facebook, Instagram? Where do you see the biggest audience?

• 37:59Speaker 02

  Yeah, I mean, I guess it depends. Like I value things differently, right? So, you know, a million views on Instagram is worth more to me probably than a million views on TikTok. But, you know, 50,000 people signing up for an email list is going to be way more than, you know, to me than all of those. Because I'm, I'm actually owning that relationship. There's not an intermediary platform there. I, I would say our daily email, which is about 500,000 people a day is probably the biggest slash most valuable of the audience. The podcast is like maybe five, six million people a month. So that's very big. Instagram's probably after that. YouTube's, you know, some, somewhere after that.

• 38:42Anthony Pompliano?

  As you think about those different audiences, different size. One of the aspects that when I asked you, are you an author, a creator, an entrepreneur? Is a lot of the work that I've seen from afar, you think about it like an entrepreneur. Yes, you're a writer. Yes, you're an author. But it almost feels like social media, you're putting content out, you're grabbing people's attention. They say, hey, who is this guy? What are these? Ideas, you're then almost pulling them to the email. And then there you can recommend things, you can push your own book. You can kind of play this game as to you have the attention, you have the relationship. How intentional is all of this versus is it just something natural where you're like, hey, I want to get people as close to me as possible and own that relationship. Like, talk a little bit, just kind of that journey over the last few years of building out kind of more of a business around the writing.

• 39:27Speaker 02

  It's a, I think it's a little bit of both. I mean, sometimes people go, oh, you're just doing this for the money. And I go like, if I'm doing this for the money, like, talking about an obscure school of ancient philosophies, like, the worst business decision I could have possibly made. And, and specifically, you know, publishing physical books in 2022 is, you know, not exactly the cutting edge of, you know, sort of scalable monetizable intellectual property. So I think first and foremost, I just, I genuinely love this stuff. And this is what I would be doing if there was a big audience or a small audience. But I remember I had a conversation with Casey Neistat like many years ago. And he said something, he said two things, which I think about all the time.

• 40:07Speaker 02

  He said, look, if the two of us were doing this for money, we should just start an advertising agency. He's like, that's where the money actually is. So like, we've already decided that maximizing financial gain is not our primary priority. And then he said, the second thing is, with the money that you do make, the reason you are making it or should be making it is so you can do more cool work, right? And, and that hit me in a, in a really big way. And one of the changes I made in my business several years ago, which was, you know, after I got into a certain amount of scale, it was like, hey, we have a budget here, we can advertise.

• 40:49Speaker 02

  Like, we could, you know, we know this is our audience, I can advertise books, I can advertise the talks, whatever, I can advertise. And then it occurred to me one day that I was spending money on advertisements, which have zero positive social impact whatsoever. And I, I made this shift right around the beginning of the pandemic. I said, you know what, I'm not going to spend any more money on advertising. I'm only going to spend money on content. I'm going to make more content, not only because the content is better, is better at advertising than advertising is, and it has a longer shelf life, but there is at least a positive impact.

• 41:30Speaker 02

  To the content, right? Like, at the end of the day, I'm not going to care exactly how many copies of my books I've sold. I'm going to care how much impact has my work had. So there are like, I see this every single day, right? We'll post a page from the Daily Stoic on Instagram on an account called Daily Stoic. And people will go, what book is that from? Right? And it's like, from, from the, the book of the thing that this is named after. That's the book. And I realized, and I actually take this as a compliment. These people are consuming content about Stoicism, an obscure school of ancient philosophy, every single day for free. And they don't know who I am, or that there's even a book about it. Right?

• 42:14Speaker 02

  And so obviously, on the one hand, that's a marketing opportunity. But, but what that really means is I'm spreading the ideas out in the world in a, in a, in a way that's reaching people who I otherwise ordinarily wouldn't reach. And so, so a big part of what I think about is, is like, I just want to have as wide a funnel as possible. I want to be reaching as many human beings as possible with the work, knowing that eventually they'll trickle down. And some of them will be book buyers or whatever. But as far as like the actual way I, I do the business, the, the other thing I think about is, and I'm sure you see this with your stuff, which is when you have a really wide funnel, and this is what gets me excited about the, the, you know, sort of creator economy.

• 42:58Speaker 02

  When you have a big podcast or a big social media following, or, you know, whatever it is, people want to buy that space from you for advertisements, right? The, and advertiser says, oh, that space is worth $10,000 to me because they think they can make $100,000 in revenue from that spot, which means that actually the spot is worth $100,000. Right? And so the way I think about it is, instead of selling that to a third party who's going to take that 10x gain, why don't I just make stuff that I like, that I think is cool, that is actually in line with the ideas that, you know, my work is based on? And then I'll just use the majority of that

• 43:39Speaker 02

  Inventory myself. And so what I'm doing there, you know, with these sort of philosophically inspired products, which have been really cool, as well as, you know, sort of financially rewarding. That's actually the same playbook that, you know, Rihanna is using or the Kardashians are using. People with huge audiences are realizing, instead of doing a celebrity endorsement, I'm just gonna be an entrepreneur and build my own brands. And I think, to me, that's the future of the creator economy.

• 44:12Anthony Pompliano?

  Couldn't agree more. And I love that you're pointing out, this is happening all across, you know, kind of society, culture, whatever. When you think five years from now, where does most of the revenue come from? Is it the books? Or is it some of these businesses? Is it advertising dollars against the emails and the podcasts? Like, how do you think about maybe where your business is going, not so much where it is today?

• 44:33Speaker 02

  Yeah, I think it's probably a mix of all of those things. I could very easily go 100% in either, in any one of the directions. And advertising would probably be the easiest. Because, you know, all you have to do is record the ad spot for LinkedIn jobs, or, you know, whatever the sponsor of that moment is. And I did a podcast deal with Amazon Wondery recently, which is, which has been nice. But I think what gets me excited about like the physical products is that, like, I'm making something that, yes, is for sale, but ultimately, you know, has some value in the world.

• 45:14Speaker 02

  It is codifying or, you know, helping people apply the philosophical idea, you know, in a, in a practice. And you think about this in music, like, obviously, a musician gets the most excited about writing music and recording music and releasing music. But they might make more money from touring, and they might make the majority of their revenue from touring by selling T-shirts on the road. All of it is funding the creative act, which, you know, got them inspired to be a musician when they were, you know, 14 years old in the first place.

• 45:53Anthony Pompliano?

  As you see kind of the business aspect of this, you're still publishing through a publisher. I don't know if you own the publisher or it's an outsourced one. And then you've got the bookstore. Talk a little bit about the actual book publishing components and like the business there. Where do you see the opportunity like in the bookstore to actually go set up your own versus still use kind of what I would consider legacy infrastructure? Or just well established kind of outside infrastructure?

• 46:19Speaker 02

  Yeah, so I I'm with Penguin Random House, which is I guess now the biggest publisher in the world. And I think they're trying to merge with Simon and Schuster, which would make them even bigger. So I I work with the traditional publisher for a couple of reasons. One, I have self published books before and it is an insane amount of work. Like much more than people think it is at scale. So, look, if you're if you're if you're going to sell a book, if you're going to write a book that's going to sell 15,000 physical units, you should probably self publish it. You'll make more money. It's not that difficult. But if you're gonna if you're gonna sell a book that's gonna do a million physical units, you know, over 15 years,

• 47:04Speaker 02

  that that becomes quite difficult. That becomes not just quite difficult, but but financially expensive to actually be able to pull off, right? Like, who pays for that inventory? Who stores that inventory? You know, who negotiates with the printer, etc. So, so I've worked with the traditional publisher on most of my books. But I'm also in a space where I I get large enough advances that

• 47:35Speaker 02

  it more or less makes what I would make if I was self publishing, right? Or guarantees that I will make what I would make if I self published a hit, right? So I, you know, There's a certain degree where I'm taking some money off the table by traditionally publishing, which allows me to take more creative and entrepreneurial risks in other domains of my life.

• 48:01Speaker 02

  And then, as far as the bookstore, again, not the world's greatest financial decision, but part of the reason, like, I'll give you an example. I sold a four-book series in 2000, the fall of 2019, which is the one that I'm in the middle of doing now. So I did Courage is Calling, Discipline is Destiny came out last, late last month. I'm in the middle of writing the third and the fourth one. I took the advance that I got for that series, and I bought two buildings here in Bastrop, Texas, which are now the headquarters for all the stuff that I do. And I have a bookstore downstairs. I wouldn't have been able to do that if I was also paying for, you know, the physical copies and all this stuff.

• 48:43Speaker 02

  So, so part of what I use my relationship with the publisher for is to fund the other creative projects where I have more, more creative control and more upside to them. So I see it as kind of a hybrid strategy. And the bookstore has been this, you know, weird, cool experience where I thought I was, I didn't exactly think of it as a nonprofit, but I certainly didn't see it as a huge money-making experience. But it's actually been a great, you know, a great, you know, let's say, small to medium-sized small business. It's had a lot of rewards in different ways, but, but it's been great.

• 49:25Speaker 02

  Down to the fact that I, I launched my last book out of the bookstore. And instead of, instead of saying, hey, I have a new book out, go preorder it on Amazon. I said, I have a new book out, preorder it from me and from my bookstore. And I, because I can buy the, the books as cheap or cheaper from my publisher than Amazon can, I could beat Amazon's price.

• 49:51Anthony Pompliano?

  So this is fascinating to me because I've heard different tidbits and various conversations you've had. The bookstore, when I first heard that you got it, I was like, oh, he's probably going to put his office there, which sounds like you have done. But then as I started to talk to more people, it became more obvious that like, maybe there was an opportunity. It was unclear whether you were going to be able to do it, if you even wanted to do it. But this opportunity that you're outlining is, I've seen in the emails and in various communications, it's now not Amazon, it is your bookstore. Talk a little bit about how that changes the economics of a book. And I think people will be really interested in this idea of like, you as the author get paid on every book that is sold. But the bookstore also makes a pretty healthy profit when they do sell books. And so if you then combine

• 50:34Anthony Pompliano?

  the author plus the bookstore, like, what does that look like on maybe like a single unit of a book that you've written?

• 50:40Speaker 02

  Well, so I think the core thing here is distribution. Distribution is always the most important thing to own. So let's say I'm, I don't have my own bookstore, but I just have an email list with my own fans. And I say, hey, I have a new book coming out, you should buy it on Amazon. Or I say, you should buy it on Barnes and Noble, or you should buy it on bookstore, bookshop.org, I think bookstore. Anyways, there's a indie bound, there's a couple independent versions. But the point is, if you have access to your audience, and you say, here, go buy it at this link, there's affiliate revenue. So Amazon pays like 4% to 5% in affiliate revenue. So, so even back for the last 15 years, when I've been selling my stuff, I've been getting my 15% royalty from the publisher on MSRP,

• 51:24Speaker 02

  which is the standard thing that applies against the advance. But I've also been getting a 4% to 5% kicker from Amazon that doesn't apply against the advance, because I have distribution, I have access to the audience. Right? And that's how all my launches went up until, I guess, Courage is Calling. And then, but by then, I'd opened the bookstore, and I realized, oh, wow, I can actually order my books from the publisher at roughly 50% off. And then I can resell them to my audience. And so I'm effectively, the math there starts

• 52:05Speaker 02

  to become similar to self publishing income, but without any of the risk. And so it's been interesting. I mean, it's logistically quite onerous. I mean, I just, I- I signed 10,000 copies of the book through the store. And then I I distributed and sold another 10,000 unsigned in, you know, three weeks of in the like, the final three weeks of September. So like that, that, that's, that's not all profit. In fact, there's almost no profit in there because I have to pay people to do it. And, you know, I almost lost my hand. It was, it was, it was a lot.

• 52:46Speaker 02

  But to me, the reason I was doing it, and when I told my publisher I was doing it on the series, they said, well, you know, you know, Amazon's gonna be a little upset. Barnes and Noble is gonna be a little upset. You're, you're stealing sales that these retailers are, you know, want. And I said, yeah, but I want to control the, the data, the relationship with the audience. So, you know, I think I did about 15,000, uh, maybe a little less than 15,000 on Courage. But that was 15,000 people that when I launched the next book in the series, I said, hey, don't you want the next book in this series? And I emailed them directly.

• 53:28Speaker 02

  And now going into the third book, you know, that list is 20 plus thousand customers, not like names on an email list that maybe are interested, but people who have purchased from me before. So I, I think at the core of, of what, how I think about, uh, you know, everything other than the creative process itself, uh, which I, I try to keep as pure and sort of driven by the idea as possible. Everything else for me is how do I own the relationship with the person? Because, you know, I've, I've probably sold, let's say, I, I sold a little over 5 million books. Let's say 3 plus million, at least of those sales have come through Amazon, right? Over the last 10 or so years.

• 54:14Speaker 02

  Ah, Amazon has three million email addresses. I have none, right? And, and, and that's how it works, right? You look at Colleen Hoover, huge. She's, let's say she sold 50 million books and she has four million TikTok followers. That means she has access to less than 10% of the people that she, that are her fans. And I think every creator is trying to get that ratio as high as possible. And then when you put in things like cancel culture and you put in things like, you know, the way these social media platforms monetize themselves by, by turning the algorithm down

• 54:56Speaker 02

  and forcing me to charge, you know, you want to be as independent and direct as, as humanly possible. That's, that's your insurance policy.

• 55:05Anthony Pompliano?

  So I guess on the front end of this, how much pressure or conversations have you had where the bookstore or other things that you've done, which I would put under the kind of characterization of just being entrepreneurial? Have you had people say, hey, you know, think about this before you go and you do it? And then also the second thing is like, does that lead to in any form or fashion, you worrying about cancel culture? Or maybe I do something and my book gets pulled from a certain outlet or something like that?

• 55:32Speaker 02

  Yeah, I mean, I remember I sat down, I was with James Clear, Mark Manson, Shane Parrish, Tim Urban, a bunch of other great writers. This is like maybe 2000, fall of 2019, right as I was thinking about doing the bookstore. And they were all like, definitely don't do it. It is a terrible idea. And they were, they were probably right in a lot of ways, but like to me, it was something I just, it was just something I felt like I, I had to do and I felt like it would be really cool to do. And what is the point of being successful? If, you know, all you're doing is reinvesting that money in, in shit that you don't like or don't care about. And so to me, like having a, I mean, I love books.

• 56:17Speaker 02

  Like I've loved books and I've loved bookstores since I was a little kid. Having a bookstore to me is like, you know, living in a 20,000 square foot mansion. Like, it's the dream, man. And so I definitely heard from people who said it would be a bad idea for a bunch of reasons. And I took all that criticism to heart. I mean, I think they were not saying that I would fail. I think what they were saying is it's going to be expensive and it's going to take a lot of time. So as I thought about how I would do it, I tried to mitigate that in as many ways as possible. I tried to think about how can it be as lean as possible? How can it be as, you know, resource light as possible? And I took that feedback into account and I think it's what's made it viable.

• 57:01Speaker 02

  But as far as like cancel culture stuff, I mean, generally I try not to be an asshole and I try not to stick my nose in stuff that's not my business. I try to be deliberate about what I do and say and think. I try not to be a, you know, a monster, as unfortunately many creative people are. But of course, there's a risk, you know, sort of, maybe I did something and I don't even remember, you know, early in my life, or maybe I, the rules of what society says are okay or not okay shift. Maybe you just get really unlucky. I mean, I think it would be naive to think that just because you think you're a good person means you can't, you can't ever find yourself in the crosshairs of an internet mob. I mean, of course you can't.

• 57:45Speaker 02

  So to me, my, the way I think about it is I want to be as independent from the sort of mainstream, you know, media ecosystem as possible, right? Like, look, when you, when you are part of the club, like when you have a boss, then you can get fired, right? And so I've just often thought about being as independent as possible. And even when I, when I work with someone, like I do a podcast deal or I work with a publisher, I just, I just try to consciously go, this is Stoic practice, go like, yeah, but would I, would I be okay losing this? And as long as the answer is yes, then I feel okay doing it.

• 58:30Speaker 02

  But I, but I don't, I try not to take anything for granted or assume anything is stable because that is an illusion.

• 58:38Anthony Pompliano?

  What's your ultimate goal? You talked earlier about killing off previous aspects of your career or ideas, but also you've grown in certain ways as well, it seems like. And so when you think about the ultimate situation or the ultimate goal, is it just to write books and just keep doing that for the next 50 years? Is there some other goal that you have? How do you think about what you're actually driving towards?

• 58:58Speaker 02

  Yeah, I would like to get better at doing this thing, which is writing books, and I feel like I am. And that's what I focus on. I want to be a great writer. But I also think about, there's obviously lots of very great writers who are shitty people, like we were just talking about. And then maybe they're being canceled for a good reason. And so I try to think about being successful in the space that I'm in in a way that is still conducive or compatible with being a regular person in the world that takes their kids to school in the morning,

• 59:40Speaker 02

  lives in a normal house, has free time to do what they want to do that isn't a bundle of nerves and pile of stress every waking moment. I want, if you think about, hey, I want to do this for the next 50 years. To me, the immediate takeaway from an arc or trajectory that long is you better figure out how to do this sustainably, or it's not going to work, right? Like, you're going to burn out. Either you're going to explode, or you're going to burn, grind yourself down into dust. So I think a lot about building systems

• 1:00:20Speaker 02

  and even setting goals that are incremental as opposed to exponential, which I think make it harder to sustain.

• 1:00:33Anthony Pompliano?

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• 1:01:17Anthony Pompliano?

  Amber Data delivers comprehensive data and insights into blockchain networks, crypto markets, and decentralized finance, empowering financial institutions to apply traditional finance methods to digital assets. Amber Data eliminates the infrastructure setup, integrated challenges, and maintenance headaches to access digital assets' data, reducing cost and time to market to enter the digital asset class. Learn more and download their digital asset data guide at www.amberdata.io/pomp. Again, that's amberdata.io/pomp. Go check them out today. Are there things that you've done previously, even the last couple of years, that you recognized, hey, if I continue doing this, it'll lead to burnout? And so you've pulled back or stopped doing them?

• 1:01:58Speaker 02

  Yeah, I mean, look, when the pandemic happened, I didn't go on the road. I mean, like, my family and I went different places, but like, I did not spend a night away from my family for 500 consecutive nights, which I'll probably never do again. But like, those were probably 500 of the best, not just best nights in that, like, we spent all this time together, but like creatively, I was best, right? And so coming out of it, you know, as people go, things are going to go back to normal. I was like, no way, man. I don't want things to go back to that kind of normal at all. And so I've had to, I've had to raise prices on a lot of things. I've had to say no to things. I've had to be more disciplined about, you know,

• 1:02:43Speaker 02

  now, now that there's not a compelling sort of health reason not to do stuff, I've had to make up other reasons not to do stuff, if you know what I mean.

• 1:02:54Anthony Pompliano?

  When people see you as the successful author and you compare it to other types of creators. So I don't take Mr. Beast. I heard him on an interview recently and someone asked me, you know, what's the craziest thing someone's ever asked you to do? And it was like a billionaire offered $250,000 to do like a five minute call with their kid. Have you ever gotten some of these kind of crazy requests? And I'm assuming it's not, hey, do a FaceTime with my kid for five minutes. But like, given the audience that you're writing for, yes, it probably spans a lot of different demographics and wealth status and things like that. But I do think that it probably leans towards a lot of business people, investment people, things like that. What's the craziest request you've ever gotten?

• 1:03:30Speaker 02

  I haven't gotten offered anything like that, but I, but I do, and you probably get this too.

• 1:03:37Speaker 02

  One of the weird things about being like a writer or a creative or having some sort of like sort of point of view that you're known for is that like really rich, successful people, like, I don't want to say they try to collect you, but they, they, they just like want you around. So you just get invited. You're like a, you're like a, you know, it's like anyone can afford, like any rich person can afford to pay for an expensive dinner. So the, the, the, the rare thing is like, who can they get to attend said dinner? Right? So you get invited to stuff or, or experiences. So like, I have an email in my inbox. Someone's like, hey, we're doing this like private, all expenses, like hella skiing trip. Like you have to get to this airport.

• 1:04:22Speaker 02

  We'll put you on a private jet. We'll fly to some, you know, place and then like the helicopter will take us up and down the mountain. Or, you know, I've been invited to the Super Bowl a couple of times, you know, like all this stuff like that. I get, you know, hey, Richard Branson's doing this thing at his island. Would you like to come? And like, it all sounds very cool, but the pandemic was helpful for me in a reminder of like what the opportunity cost of that stuff is.

• 1:04:52Speaker 02

  First off, it, you do this stuff and you go, this is just slightly fancier version of a different thing. Still cold skiing, you know?

• 1:05:02Speaker 02

  But but you you sort of realize that the cost is, okay, this is time away from family. This is time away from the routine. These are hours not put into the work. And I think when you work for yourself, and a lot of people experienced this during the pandemic, suddenly you're your own boss. And, you know, nobody goes, hey, Ryan, you agreed to fifty more things over the last year. And we've quantified that and your book is now sixteen percent not as good as it could be. Right? There's no math that allows you to calculate exactly what the opportunity cost of saying yes to all this stuff was.

• 1:05:46Speaker 02

  But eventually there is that opportunity cost. And there's a lot of people who would like to have my spot. Right? And there there is a lot of pressure from the audience about, you know, what something needs to be to be worth their time or energy. And I just I just try to remind myself that, you know, everything I say yes to means that I'm saying no to something else. And usually it means I'm saying no to the most important things to me.

• 1:06:19Anthony Pompliano?

  Yeah, what what's really interesting is, one, the more successful you become, whether financially or kind of just career wise, there's the old adage like everything becomes free. Right? All of a sudden now you get invited to like the super expensive dinner and no one expects you to pay and you're like, this is weird, but like, okay, thank you, I think. So like definitely that that resonates, but also this idea of the routine. And this is coming from, you know, somebody from my side of in 2019, took 120 flights. I was flying all over the country, doing all this kind of crazy stuff. And like that was just like normal, I guess. And then similar experience during the pandemic, I was like, oh, my God, like if I go to sleep at the same time, wake up at the same time, in the same bed and do the same things every single day, like there's this compounding effect. And it's only been three months of doing that.

• 1:07:02Anthony Pompliano?

  Now it's been six months. Now I'm not like, wow.

• 1:07:05Speaker 02

  Well, yeah, I I found that I I used to be able to work on planes. I wrote big chunks of my books on planes. I could read on planes. And then, you know, and it was just like it was a second home to me. It was no different than being in the office. It was no different than being in a hotel room. It was just a place. And then when I took this huge break not being on planes, now planes are total dead time for me. It's obviously something I'm working on because I don't. Uh, you know, it it I don't want it to be a dead time. Like I'm, I do have to occasionally be on planes and uh, as a result, I need to figure out how to to use that time productively. But it it's also like, I don't know if you've ever radically changed your diet, you know, you're like, hey, I cut out carbs or hey, I I went plant based.

• 1:07:48Speaker 02

  You make some change, um, and suddenly you feel really good. You feel so much better. And then you have something from the old diet and you feel like you're going to be sick. You're like, I'm be, do I have food poisoning? This is horrible. And you realize that that thing was a kind of poison. Your body was just acclimated to it. It was used to it. Um, like, I don't eat, I I tend not to eat a lot of bread. My wife uh is allergic to gluten, so like we don't have a lot of bread in our house. But I can't eat bread. I just don't. Like, then I'll be somewhere and there'll be pizza. I'll eat a bunch of pizza and I'll literally like just want to die. I'll feel disgusting and terrible, awful. Um, that's how I feel about planes now. And so, um,

• 1:08:29Speaker 02

  you realize that a lot of the things that we accept as natural are actually fundamentally unnatural, but not conducive to being in your best, uh, you know, your best headspace, your best workspace. And it's only by removing them that you realize what the costs were. And so, uh, the other thing for me was, it's like, I used to think, oh, you know, you take a week off and you recharge. You know, the pandemic, it took me months to get to like where I ultimately got, but that was the best spot. And now it's like, oh, wow. Okay. Like when I take breaks, I need to take longer breaks. They need to be more complete breaks. And this idea that just like, you know, going to the beach for the weekend is a way to recharge. You just realize you're probably fooling yourself.

• 1:09:12Speaker 02

  And it just, it just takes more and less than you think.

• 1:09:16Anthony Pompliano?

  I do think the pandemic was almost a routine cleanse for people. And what you're basically doing is you're almost like slowly adding things back to the routine. And it almost feels like maybe you add something like, oh, nope, that my body is rejecting that. Or like, my life is rejecting that thing, like, get rid of that again. And just focus on this, which ultimately leads to this question around as you want to get better and better at writing. Are you now at a point where you're like the Babe Ruth calling his shot? Or you know, when you publish, like, this is a winner? Or are you still kind of like, okay, I think it's good, but like, let's see what the audience says? Like, how confident, I guess, can you get now, given that you've written, I don't know, 10, 12 books, whatever it is? Like, do you know that it is going to be successful before it ever is published?

• 1:09:59Speaker 02

  Well, there's always the humility and the humbling nature of what you talked about earlier, which is the thing you jot off on the toilet, it just blows up. And you're just like, whoa, okay. Like, there is the thing that in a fit of inspiration or a moment of just, you know, dashing something off, you really hit something that's magical, that is always there. And I'm glad that it's there because it reminds you that like, you're not really in charge. And that like, the screenwriter William Goldman famously said, nobody knows anything. It's good to, it's good to remember that nobody knows anything. And that often what you think is going to work doesn't work. And what you're skeptical about working, works at a level that you just could not have possibly conceived.

• 1:10:42Speaker 02

  I think about it less as the Babe Ruth thing, like, I'm calling it. But I think more about like, I judge what I do more about, did I connect with the ball? Right? Sometimes that goes all the way over the fence. Sometimes it goes deep into left field, but, but somebody catches it, sometimes it fouls out. But like, to me, the important thing is, did I connect with the ball? And I very viscerally and very immediately feel whether I connected. And sometimes you connect and you're like, oh, I really got underneath that one. And it's going all the fucking way. That is a wonderful feeling. I mean, that's the feeling you're chasing. I think any creator is chasing. But, but I

• 1:11:26Speaker 02

  Try to think about it more as did I connect because this is the important thing. So many external factors determine whether that's a home run or, you know, a ground rule double or, you know, a single or, or, you know, worse, right?

• 1:11:47Speaker 02

  Like with a book, you know,

• 1:11:51Speaker 02

  I probably, I almost certainly sold enough copies on Discipline is Destiny to debut at number one on the New York Times list. But because I sold a lot of those through my own store, they didn't count all of them and I was number two. So if success for me was hitting number one, and if because I felt the numbers, I said, ah, you got a number one bestseller right here. That would have been a rude and unpleasant disappointment. Instead, all I was thinking from the writing process through the release was, I'm very confident that I've connected with the ball here and that I've done all that I can do here and that everything else is extra. So number two was great, number one would have been great.

• 1:12:36Speaker 02

  But number 10 or 11, that is not on the list, also would have been great because, because that, that feeling of connection is ultimately like why I do it.

• 1:12:45Anthony Pompliano?

  So I saw the video where I think it's your publisher is saying that you sold 60,000 copies in the first week. You debut as number two on the list. Any part of you is like, fuck, I, I wanted to be number one, right? Like, and what's interesting about it is like, I almost think you could be like, shit, I wanted to be number one, but I'm cool with number two at the same time. Like, how do you think about having ambition, but also being satisfied with connecting with the ball?

• 1:13:10Speaker 02

  So I, I've hit number one before, which was obviously wonderful. And I had a very similar conversation with my agent, you know, hey, blah, blah, blah, it's in. And so hitting number one was, was, was great, right? So one of the benefits of hitting number one is that like, I'm now a number one New York Times bestseller. No one can take that away. It's like, you won an Olympic gold medal. You're an Olympic gold medalist, right?

• 1:13:33Speaker 02

  Six or sixty is the same as one, right? Like, you, you, you got the thing. You, you did it once. There, there's a part of you, of course, that I think would like to do it again. But I think one of the things that I've taken away from hitting number one, and I've, I've hit different lists and I've, I've had other, like, sort of cool shit, is you realize how little it actually means, not just to other people. Like, it didn't substantially change my life in any way. I don't think I sold any other books, blah, blah. Nobody threw me a parade. But also, like, it didn't do whatever I thought it would do for me, right? Like, whatever part of me thought, like, my dad's finally gonna be proud of me, you

• 1:14:18Speaker 02

  know, uh, I'm finally gonna feel good about myself, or, you know, whatever, whatever the thing we think we'll feel when we hit that financial number, or we win a certain amount, or we take a company public, or we get vindicated, or we win an election, you know, whatever that thing you've told yourself is, happens, um, you are humbled by, not the emptiness of it, because that me, that, I think that makes it feel like it's nothing, but there is a part of you that feels nothing, because it is, the Stoics would say it is nothing. It is an external, right? It, it, it wasn't something you controlled.

• 1:15:00Speaker 02

  It, it, it doesn't actually say anything about you as a person. And it, it doesn't address, you know, what you feel inside. So, um, I, I think I've done a lot of work where I've gotten to a place where I truly, in, in New Orleans, they have this word "land yap," which means like the thirteenth donut that sometimes the baker throws in, sometimes they don't, but it's just nice to have. I've gotten to a place where, uh, I've, I can, I can actually see that stuff as extra and nice, but in no way like the determining factor of whether I think it's good or not.

• 1:15:41Anthony Pompliano?

  One of the best ways to get at someone's focus and kind of what they care about, I think, is how they keep score. And so when you think about your life today, it doesn't strike me that you keep score based on how much money you make. But what do you keep score? Is it how many books you sell? Is it the number of people on an email list? Like, when you think of, okay, this is the score I'm keeping and kind of what you measure ends up being the thing you move, what is the scoreboard or scorecard right now?

• 1:16:07Speaker 02

  Yeah, Epictetus, one of the Stoic philosophers, says, "If you only enter competitions where winning is up to you, you will always win," right? And so, obviously, I'm a competitive person. I've always been competitive. And it's easy to be like, okay, I keep score by copies sold, I keep, you know, how many weeks on the bestseller list, how much money, etc. Those are easy. That's the external scorecard. But the problem is, the external scorecard is not up to you. What I think is, one of my best pieces of writing has sold the fewest copies of any of my books. And I don't want to say that my bestselling

• 1:16:45Speaker 02

  book is my worst book, but what, it's very clear to me, when I look at sales, that quality and sales are not as correlated as we would like. And certainly, awards, critical reception, fan favorites, these are also decoupled from that. So I try to push that away as much as possible. And I try to go to a place where I determine, I'm the scorekeeper, right? Which is like, as an example, am I getting better as a writer? Like, is the writing better according to me in each subsequent project? If the answer is yes, then I win.

• 1:17:28Speaker 02

  And I get to decide that. Now, you might say, oh, that's a little circular, that's a way of cheating, maybe that holds you back. That's not as ruthless as, say, like, you know, copies sold. But when you realize that copies sold, you know, a lot of shitty books sell a lot of copies, you realize that's not really such a good metric either. So I try to measure myself on that. Am I getting better at the thing itself? And is it more integrated into my life as a person? That's the other thing. So like, I would say that each book that I have done has been, I don't want to say easier, because they've been harder in a lot of ways. But they have been less disruptive in my life. Right?

• 1:18:12Speaker 02

  They, I have been more of a normal, reasonable,

• 1:18:20Speaker 02

  livable person to be with as I've gone. And that means actually a lot to me.

• 1:18:28Anthony Pompliano?

  You've mentioned family a couple of times and also being a livable person just now. What have you learned about parenting over the years? And like, maybe what is like the study of the Stoics help you or hurt you in terms of being a parent?

• 1:18:40Speaker 02

  Well, that, that video you mentioned, so my agent calls me and goes, hey, you're number two. And my son, I, I was in the other room where I do a lot of my research. My son was sitting like on a chair in my office. And so no one was around, so just my son. And I said, hey, Jonesy, I, I just, I just hit number two. And he runs into the room and he goes, can I watch YouTube now? And, uh, you know, I think one of the things that kids do is they just, they don't give a shit at all. Right? Like, they don't care whether you made a million dollars today, or whether you lost a million dollars. They don't care if people like you. They don't care if they, if you like yourself. They just care whether you provide for them, whether you're what they need, whether you're present and fun and, uh, you know, connected with them.

• 1:19:21Speaker 02

  And so I think one of the things family does is it's, I think people are often, that people often think that family will hold them back or hold them down. And I would actually agree with that. It does. It holds you down on planet earth. When your ego wants to take you up, you know, when things want to go to your head, when you're, when you're.

• 1:19:44Speaker 02

  Able to spin off the planet because everyone enables you, tells you you're awesome because you, you know, there, there's a, a line from Bertrand Russell I like. He says, "The first sign of an impending nervous collapse is the belief that your work is terribly, terribly important." And, and family kind of reminds you that it's not terribly important, right? Like, like, they're like, "Why aren't you home? We're having dinner," you know? And so I, I, I think being rooted and connected to reality is the most important thing. And when I, when I look at like, you know, famous people that are spinning off the planet, I'm like, "That's a person who," I mentioned this earlier, "that's a person who did not do school pickup today," right? Like, that, that, that's a person who did not have to get up in the middle of the night

• 1:20:29Speaker 02

  with a crying baby. That, I, I, I read a thing about, um, uh, Lin-Manuel Miranda. He was talking about when Hamilton blew up, uh, like his first child was born like as they were doing the dress rehearsals for Hamilton. And he was saying that, and I think about this a lot, it jives with my experience, as Hamilton became the biggest thing in culture and it was making millions of dollars and famous people were coming every single night, he had to leave immediately after the show to go home because he had an infant, uh, because he actually took his duties as a, you know, father seriously. But he also knew, "Hey, if I go out to this after-party and I get home at two, well, a

• 1:21:14Speaker 02

  baby's gonna wake up, wake me up multiple times in the middle of the night and then I'm not gonna sleep well and I'm not gonna be able to perform tonight." And so that I, he was basically saying that having kids kept him honest. And I, I think that is a really, really important, uh, part of this. Like, it is so easy, suddenly your work's reaching millions of people, suddenly, you know, you move this thing around on your computer and you're moving huge amounts of money around, so the president is calling you or, you know, whatever, whatever the thing that you're in, the position of success or influence that you wanted, you worked so hard for, you get it. But to maintain it, you have to be rooted and you have to be connected to reality.

• 1:21:58Speaker 02

  And I think kids are an incredibly important counterbalance to the selfishness and ego and, and, you know, busyness that, that, that successful people can be sort of like a moth to a flame to.

• 1:22:17Anthony Pompliano?

  So the first thing is, I now think your son's a genius because he knew you were in a good mood and asked to go watch YouTube. So, so capitalizing on the opportunity. But, but the other piece of this is, a lot of people do focus on like, how do I reach, you know, the pinnacle of my career? How do I reach that accomplishment? But really what you're talking about is like, once you get there, actually the greats at whatever they do, it's the ability to compound and stay there for decades. Or you talked earlier about, you know, Robert being able to sell books, more books this year than he ever has before. And that is just the ability to continue to stay focused and the ability to keep that discipline, which is part of what you write about in the book. And I thought the section on Lou Gehrig was, just really spoke to this whole idea of the hard work, day in, day out. It doesn't matter what's going on. If you continue

• 1:23:01Anthony Pompliano?

  to do that, people may not notice on the day to day basis, but over this long period of time, it becomes very obvious to people like this person is different, this person is great, this person is able to do something the rest of us aren't.

• 1:23:13Speaker 02

  Yeah. I mean, first off, to go to the idea of like the true greats, like when you look back at your life, you're not going to, you're not going to think about, you know, how much money you made, how successful you were, et cetera. If, you know, you're alone, if all you want is for your kids to answer your phone, or, you know, answer the phone when you call, like success at the end of your life, I've said this before, is a crowded table, right? It's like family and friends that want to be around you. And I think, I know you, you've probably met them. You meet really successful people and you're like, this is the loneliest fucking person in the world. Like this is, I would not trade places with this person. Right? And so, so, you know, first off, it's, it's defining what success actually is. And I think there needs to be a sort of a more

• 1:23:58Speaker 02

  holistic definition. But yeah, like what's fascinating about Lou Gehrig, and I read a ton about him as I was, he's the first, he's, he's who I have embodied the idea of physical discipline in the book.

• 1:24:12Speaker 02

  He's so well-known for his streak of 2100 consecutive games that his stats are almost totally forgotten, but because he consistently played and played consistently well, he's like the all-time leader or on the all-time leaderboard still for some of the most impressive statistics in baseball. I mean, he batted 500 in multiple World Series, right? He had an insane career batting average, an insane number of home runs. He won multiple batting crowns, multiple RBI crowns. You know, he was just an incredibly, he wasn't like

• 1:24:56Speaker 02

  the greatest, but because he was consistently good for so long, for such long uninterrupted periods, his numbers are up there with most of the all-time greats. It'd be like, obviously, Aaron Judge has had this incredible season, but if Aaron Judge consistently hit 40 to 50 home runs like every year for like 20 consecutive years, I mean, just imagine where he would be. And that's effectively what Lou Gehrig was. We talked about Babe Ruth calling that homerun. Lou Gehrig hit two homeruns in that game too, right? He was just one of the all-time greats because he was consistently so good.

• 1:25:39Anthony Pompliano?

  My wife and I always talk about our life changed when we got to a point where we would go meet these hyper-successful people and you feel so fortunate and like, oh my God, I'm gonna learn so much from these people or whatever. And then we would leave, whether it was dinner or an event, you know, it's time at their house or whatever. And we'd always ask ourselves, would you trade lives with them? And as you just mentioned, it's kind of crazy when all of a sudden you're like, no, I wouldn't. Like this big multi-billionaire with, you know, all the crazy stuff and this crazy life and they're flying around the world and all of a sudden, like, I wouldn't trade lives with them. Like, you almost feel, again, you've like unlocked a different part of life that, for some people, it's not for everyone, but for some people, they really feel like it's more rewarding to live, you know, maybe the life I live or the life you live, which is kind of a crazy thing because

• 1:26:24Anthony Pompliano?

  as a kid, that's not what you think is, you know, the pinnacle of success.

• 1:26:28Speaker 02

  Well, it's funny, I am probably one of the most viewed like Instagram reels or TikToks that I ever did. I told this story about Kurt Vonnegut and Joseph Heller. Kurt Vonnegut wrote Slaughterhouse Five, Joseph Heller wrote Catch Twenty Two, two of the most successful fiction authors of the, you know, mid 20th century, two of the great writers of all time. And like we were talking about, you get invited to these parties and they're in, they're at some party outside New York City, probably in the Hamptons of some, you know, billionaire. And Vonnegut is teasing Heller and he, and he says, you know, how does it feel to know that this guy probably made more money this week than, than Catch

• 1:27:09Speaker 02

  Twenty Two will make in your lifetime? And Heller goes, yeah, but I have something that he doesn't have. And Kurt Vonnegut says, what could that possibly be? And Heller says, I have enough, right? Like I, he says, I know what enough is. And enough is the wealthiest place you could possibly be, right? Like, if you feel good and, and happy making a hundred thousand dollars a year, you are far wealthier than someone who made a hundred million dollars last year, but is comparing themselves ceaselessly and relentlessly to someone who made a hundred and twenty million dollars last year, right? One of the Stoics

• 1:27:50Speaker 02

  said that poverty is not having too little, it's wanting more. Now, obviously poverty is real. And if you can't pay for, you know, your kid's diapers, or your car is broken down, you're gonna have a hard time just going through life. So I'm not trying to be glib. But what I am saying is that after a certain point, it is jealousy, it is comparison, it is insatiableness that is, you know, the poorest place to live or be. Because it doesn't matter what you do, it doesn't matter how, what people think about you, you're always gonna be focused on, but does this person have more? Why didn't I get this? Well, what

• 1:28:33Speaker 02

  if I reinvest this? Can I get this? You know, there's no like law that says You have to make more and more and more and more, but but we sort of just because we don't really know what we want. We don't really know what we want our lives to be. I think we just intuitively and instinctively try to acquire more and more. And sometimes this is good, but a lot of times it makes us profoundly unhappy.

• 1:28:58Anthony Pompliano?

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• 1:30:25Anthony Pompliano?

  And I thought we could spend a few minutes talking about some of the Stoic philosophy and some of the events. And a great place to start would just be like, how do you balance maybe the aspirational element of controlling emotions and happiness? And like all these great things that we read about. And then when you actually learn about history, you're like, you know, Marcus Aurelius and Commodus and like their wives are being killed. And like, just like the crazy ruthlessness of the times with also like the writings that seem to be what we all aspire to one day, you know, live that life. Like, how do you kind of balance those two things?

• 1:31:00Speaker 02

  No, I think it balances the right word because if you just read the Stoics writings, you get this sense you're like, oh, you know, no amount of external success matters, or like, don't care what other people think, or focus only on what you control, et cetera, et cetera. And you can get this sense that like, oh, the result is they became these like monks who lived in the hills somewhere and didn't participate in life because maybe all that's meaningless or outside of their control. But, you know, you think about Seneca. Seneca is one of the most powerful politicians in Rome. He is one of its most successful businessmen. And on the side, he writes these beautiful haunting plays that are so popular that actually

• 1:31:44Speaker 02

  at Pompeii, you can see a line of graffiti that is a line from one of Seneca's plays. It's preserved there for all time. So Seneca was a person who did stuff. And the Stoics got married and they had kids and they worked jobs. So I think what it is, and the way I think about it is, look, if you're an ambitious, talented, you know, sought-after person, you need to be reminding yourself, hey, these external things don't matter. Hey, focus only on what's in your control. Hey, you can't take this money with you when you die. You need those reminders. You already take for granted that, you know, doing great work is important, that you should strive to maximize your potential,

• 1:32:27Speaker 02

  right? That you should try to shape the world for the better. You already have taken all this for granted, but it's so easy to take that to excess, right? To think that you're the center of the universe, to like we're saying that your work is terribly, terribly important. You need to balance it out. And so when you read a book like Meditations, I think what's so incredible about is you have the most powerful man in the world writing notes to himself, little reminders like, hey, look, this is important, but losing your temper doesn't make things better for people. You know, he goes, hey, like, yeah, your job is to manage all this stuff, but your real job is to be a good person, right? That that is what ultimate success is. And so I think the Stoics were like, exactly like you and I, exactly like a lot of the people

• 1:33:12Speaker 02

  that were, that are listening to this right now. They're ambitious, they're driven, they're talented, uh, they're, they're busy, et cetera. These are the people that need these reminders. The person who's never gonna get up off their couch, who doesn't care, who isn't trying, they got it under control. Uh, you know, th- this is not a concern for them, right? It's like ego. Ego is a huge problem, but not for losers, right? You know, like ego is a, ego is a disease of success, right? Uh, it, it is a problem. It is a thing that will destroy what you have built. Uh, and so, so I think it's, we're the people that need these things more than anyone else.

• 1:33:48Anthony Pompliano?

  I, I think a lot about like ambition is an ingredient for both success and ruin. But if you're not on the outliers of the, of those two things, and you're just kinda like, you go through life, you're not too successful, you don't ever meet ruin, ambition may not really be a key ingredient to, uh, to surviving, right?

• 1:34:06Speaker 02

  Yeah, I, I heard someone talking about like all these social, uh, these social entrepreneurs, right? They're like, and we're gonna donate a percentage of our profits to charity. And he was joking, he's like, you should probably have profits first, right? And so sometimes we get carried away with this stuff, like thinking about it when, when it's, it's not even an issue for us. It's like tax, tax planning, when you're making, you know, $20,000 a year. This isn't something that you need to think about. But suddenly, when, you know, the business takes off, yeah, if you're not thinking about it, you're gonna be leaving opportunities or gains or, or, or, or, or profits on the table. And so, uh, yeah, you can get carried away, uh, obviously, but, but, uh, it, it's really at the highest level

• 1:34:50Speaker 02

  when the stakes are, when the stakes really matter, that, you know, ego and, uh, excess and ambition, all these things start to be really worth paying attention to.

• 1:35:01Anthony Pompliano?

  So it's obvious the Stoics, obviously, uh, in their lives, they made mistakes, they did crazy stuff, whatever. But in their writings, is there anything that you vehemently disagree with, or you think that they like got wrong?

• 1:35:12Speaker 02

  That's a good question. I mean, look, the the Rome of, you know, that period was a hierarchical, stratified society in which individuals had like no agency, right? So like, I'll give you an example. Almost none of the Stoics questioned slavery, including Epictetus, who was a slave, right? Like, he gets free, he frees himself from slavery, and he talks about why it's not good to be a slave, like as a metaphor. But at no point does he go, hey, it's pretty fucked up for one human to own another human, and we should, you know, disregard this institution,

• 1:35:52Speaker 02

  or do something about this institution. And that was because I think the Stoics, the Stoics were so focused on what was in our control versus not in our control, and so focused primarily on individual choice, that I think they missed a lot of opportunities for collective action. And the 2000 years since, you know, Epictetus or Marcus Aurelius, we have been the recipients of the learned experiences of people who did things that, or changed things, that we didn't think were possible. Like, I'll give you an example. Let's say you were a student of the

• 1:36:35Speaker 02

  Stoics, and you lived in the American South in the 1930s. You might personally not be a racist. You might personally think that segregation and Jim Crow was a moral abomination. But maybe you would say to yourself, this is an injustice that's outside of my control. And so I'm going to focus on being the best person that I can. And I'm going to have to accept that this is when I was born, and this is when I live, right? It's not until civil rights leaders, Diane Nash, Martin Luther King, Malcolm X, come along and go, actually, hey, if we all come together and we exert certain pressures, and we stop focusing only on what we individually

• 1:37:19Speaker 02

  do, but on what we can collectively accomplish. We can change these things. And so I think one of the areas that Stoicism struggles, at least in the historical record, is their ability to come together and bring about collective change, which is perhaps outside of the individual's control. But if all individuals think that, no change is possible. Do you know what I mean?

• 1:37:44Anthony Pompliano?

  Yeah, completely. And one of the ideas that when people read about Stoics, or they study it and they learn about it, they start thinking modern Stoics, like who are the people who are going to be the the modern, you know, version of the Stoics? So I want to be interested to hear your ideas as to like who those people may or may not be. But also, whenever I hear people talking about it, they constantly jump to like, well, who's trying to create change, right? Who are the people? Which almost is in opposition to the way that the Stoics actually were. And so when you think of the modern day, are there certain people who are either public or maybe even private that you think really embody maybe the Stoic lifestyle or philosophy? And then also, like, is there an overlap where maybe the Stoic version of the

• 1:38:26Anthony Pompliano?

  modern day is like the people on social media who are calling for change and are successful? Or how do you kind of think through that?

• 1:38:32Speaker 02

  Yeah, I mean, it's interesting. I think George Washington, right, is this sort of example of the tension there. So George Washington bases his entire life on Cato, one of the great Roman Stoics. That's his hero. That's who he models all his decisions on. And obviously, Washington was wrongly resigned to certain sort of parts of culture and America at that time. But by another definition, he creates a new country from nothing with a small ragtag group of individuals. So I think there is a tension in the Stoics where sometimes they're to resign,

• 1:39:11Speaker 02

  but at their best, they're absolutely on the forefront, the cutting edge of change, action, you know, inventing new things, making new things. So I don't want to paint the Stoics with too broad a brush that like the Stoics never engage in social change. Of course they do, and they always have. Although I had Stacey Abrams, the politician on the podcast a while ago, and she actually, when she lost that election in Georgia, she said, I'm not going to be Stoic about this. I'm going to do something about it. And you know, she ends up obviously creating this voting rights organization that swings.

• 1:39:51Speaker 02

  The 2020 runoff probably wins Biden, Georgia, and thus the election. And then certainly is the catalyst for the Democrats taking the Senate in that runoff. Now, you can say that this is good or bad, or you agree with it or disagree with it. But my argument to her was that's actually the definition of Stoicism. On the one hand, you took something that you felt was unfair and unjust. And you didn't complain about it. You didn't whine about it. You didn't quit, take your ball and go home. But you disagreed with what happened and then you set to work affecting change in response to what had happened. And so to me, that's what Stoicism is.

• 1:40:34Speaker 02

  I don't feel the need to say she is a Stoic, but I would say that approach is itself Stoic. When we say, look, I don't like how things are. I object to how things are. I understand that there might be large swaths of this that I simply have to accept. But there are parts of it that I do not accept. And because I believe I have the ability to change them, I am going to get to work at doing so. Right? If nobody believed they could change the world, the world would never change.

• 1:41:05Anthony Pompliano?

  Yeah. When I ask people for questions, there was a bunch of folks who basically were like, look, I get it. Stoicism is this amazing thing. He's done a bunch of work there. I never hear him talk about X. And some of them I had heard about, some of them I hadn't. One of them was like Tao Te Ching and many other types of philosophical views of the world and things like that. Because you've been so focused on Stoicism, do you look at other areas of focus? Do you compare? Do you feel like you can learn? Or are you just like, hey, look, Stoicism is the thing I'm most focused on. Everything else is cool, but like, that's not really my focus.

• 1:41:39Speaker 02

  No, I definitely try to read very widely. Seneca says we should, we should read like a spy in the enemy's camp, right? That we should, we should always be reading people we disagree with. And what's fascinating about Seneca is the philosopher that Seneca quotes the most is not a Stoic. It's Epicurus, right? The founder of Epicureanism, like his rival. So I try to read accordingly. And actually, my book Stillness is the Key is rooted in the Stoic concept of ataraxia or stillness. But I quote quite liberally from the Tao Te Ching, from Confucism and Buddhism and Christianity as well. Like, I'm not, I'm an agnostic. I'm not an atheist, but I'm not religious.

• 1:42:26Speaker 02

  And I quote from the Bible all the time, and I've read it many times. And so I try to read quite widely and study these other schools. Stoicism happens to be what I come home to and what I have found because of this reading to stand up the best. But I try not to close my mind to this other stuff, for sure.

• 1:42:46Anthony Pompliano?

  When you think of all the work that you've done, all the people you've studied, is there one quote that you come back to and you're like, this is the quote that describes my life, or this is the thing to like, put on my tombstone the day I die, that really just kind of stands head and shoulders above everything else?

• 1:43:01Speaker 02

  I mean, I go back and forth. I think what's so lovely about the Stoics is like, you crack them open, and then whatever you need at that moment is there. I think the Tao Te Ching is the same way. The Bible can be the same way. It's like when the student is ready, the teacher appears, right? You find what you needed to hear in that moment, because you bring to it something that maybe is not even actually there. But there's a, there's a line at the beginning of Meditations that I've thought a lot about in the last couple of years. Marcus Aurelius is talking about what he learns from this philosophy teacher he has named Sextus. And he says that he learned to be free of passion, but full of love.

• 1:43:42Speaker 02

  And I love that because it doesn't, it doesn't sound like Stoicism. The, the free of passion part does, but the full of love part maybe doesn't. And I like that as a, as a kind of counterbalance to this idea of Stoicism being harsh and unfeeling and, you know, driven and robotic. I, I like the idea that the, the point is to take away these destructive emotions. So what there's room for is empathy and connection and, and love. And I don't think he just means love for other people. I think he also means like a love for, you know, the moment of time that you're in,

• 1:44:23Speaker 02

  for the situations that you're in, for the hand that life has dealt you, even if those are not what you wanted, even if other people might think that that's a really shitty hand. The idea of being full of love, that's not something I'm consistently able to do, but it's what I aspire to do.

• 1:44:40Anthony Pompliano?

  The last thing I wanted to talk to you about is this idea of death drives focus. And you've written a lot about kind of mortality and, and the mental focus. There's many other people who, who have referenced this. But what's interesting about it is it really gets at this idea of time and the finite amount of time. There's a concept that Graham Duncan popularized, Time Billionaire, that, that just I think really hammers this home. How do you think today, given all of the things you've done in your life, you know, you're around the age of the midpoint, right? If, if you're fortunate enough to kind of live till, till life expectancy or whatever. Have things changed? Do you think about it differently than maybe you used to? Death drives focus?

• 1:45:24Anthony Pompliano?

  Like what kind of just comes to mind when you hear those phrases and kind of that, those ideas?

• 1:45:28Speaker 02

  No, I love that concept. I mean, we were talking about wealth earlier. If you don't have time, how rich are you? You know, like, if you don't command or control your schedule, how powerful are you really? Now, I get like, obviously, you're the president or whatever. You know, there's this period where you're accepting that for some time you don't control your schedule. But I think so often, we conflate busyness with success. And when I don't have time to do the things I want to do, whether that's weed, write, spend time with my kids, work out, like, if I have a jam-packed day, like, when I pull up my calendar and it's fucking full, I'm like, this sucks, right? This is not success. This is like, like, I'm one step

• 1:46:12Speaker 02

  away from having to put on a suit and, you know, be at an office, right? Like, that's not what I want. I want, I want autonomy. So, so my definition of success has always been autonomy, that I can say what I want, I can think what I want, and I can do with my time what I want. And the reason we have to value time over these other things is that time is the most precious resource. It's the only non-renewable resource. Seneca makes this fascinating point. He said exactly what you were pointing out, that I'm at the midpoint. You know, we tend to think of death as this thing in the future, he says, that we're moving towards. But he says, this is the wrong way to think about it. He says,

• 1:46:52Speaker 02

  because the time that passes belongs to death. Like, every minute that's passed is dead forever. And so he says, we're not dying once at the end, we're dying every minute, every day. And so if you think about it that way, to me, it, it puts in stark relief, like, how one chooses to spend their time. And one of the most powerful questions in, in meditations, Marcus goes, are you afraid, or he says, he says, are you afraid of death because you won't be able to do this anymore? And he means this as a blank, like, like, you're like, you know, in some boring ass conference call. And he's like, you're afraid of dying because you won't be able to be on any more conference calls, right? And, and,

• 1:47:38Speaker 02

  And I think that's a really powerful way to think about. Obviously, there's some stuff you have to do in life that that that you don't want to do. And if you lived as if you were for sure going to die tomorrow, you would probably not actually live a very good life. But if you can live as if death is always a possibility, I think it gives you perspective and clarity and focus.

• 1:48:02Anthony Pompliano?

  That's a great place for us to end. I could not agree more. Your new book, Discipline is Destiny, is a New York Times bestseller. Where where should we send people to to buy it? Not Amazon?

• 1:48:14Speaker 02

  Just go to dailystoic.com/discipline, or you can come to my bookstore, The Painted Porch, in Bastrop, Texas, the next time any of you are in Austin.

• 1:48:23Anthony Pompliano?

  Awesome. Ryan, listen, thank you so much. I really appreciate it. I know that a ton of people enjoy your writing, the various books that you put out, all the social content, and we'll definitely do this again in the future.

• 1:48:33Speaker 02

  Thanks for having me. Let's do it in person next time.

• 1:48:36Anthony Pompliano?

  Thanks so much for listening to today's episode. I really hope you enjoyed this one. Make sure you're subscribed on Apple, Spotify, or your favorite podcast player. And if you're looking to transition into a brand new job in the Bitcoin or crypto industry, we've got you covered. Head over to thecryptoacademy.io. My team and I have been working with the top HR teams in the industry to develop an intensive three-week training program with over 50 live events. We teach you exactly what you need to know to break into the industry, including live interview prep and resume review. Our students have been hired at over 75 of the world's best Bitcoin and crypto companies. Go to thecryptoacademy.io to learn more. Again, that's thecryptoacademy.io. If you enjoyed today's episode, make sure you share it with your friends, and I'll see you all for the next episode.