How to develop discipline: A conversation with Ryan Holiday (2022)

26:28And then once I've proven I can do it, And yeah, marketing book from a, you know, sort of a controversial figure in marketing is more accessible from a business publishing standpoint than young person without philosophy degree writing philosophy books. So you gotta have some - It's a more universal story. Like who do I wanna learn from when it comes to the cutting edge of marketing? Probably a 23 or 24 year old who's working at a cutting edge company. Right. Yeah, and like obviously social media is different because there's no gatekeepers and that's great. But when you are operating in a world of gatekeepers, you have to have some empathy for the gatekeepers, which is like their main thing is like they don't want to get fired for betting on you.

27:13So you have to make that bet seem not crazy. And people don't do a good job of that. They don't think they just, like these people see good ideas all day. Why is your idea not stupid for them to bet their reputation? Like they have to go into a Monday morning staff meeting and go, I think we should give this person a show. And like, you don't want, like, how is that a good, how have you made it possible for them to make that argument? You kind of have to like think of, we've talked about this a lot where we do this exercise where we write headlines about ourselves. To explore like how will the market receive these next projects that we're doing?

27:54Is it easy to communicate to someone in a sales room, right? Is it easy if a marketing meeting is happening? Can they explain what we do in a single headline? And if they can't, then something's wrong and we're not communicating our message strong enough. And no one's gonna give us a chance. So I think that - It's better to fix that early. Early, yeah. You have to. And we actually took like weeks or potentially months off before we started this show to kind of recalibrate and be like, when this show launches, how do people talk about it? Like we essentially write the conversation that you want people to have and then back into the product or make sure the product is showcasing that.

28:35And it's easy to pull that from the product. Yeah, and it's like, why would a guest come on the show? Like is there a proposition for them to, you know like just actually thinking it's not just what it means to you. But how does it look and how is it perceived? From the outside. And what is the entry point for all the different stakeholders? So you mentioned like American apparel is, you know, notoriously controversial when it comes to marketing. Yeah. What was that like? It was insane. It was insane is what it was like. It was a lot of lessons about how stuff works. A lot of lessons about how stuff should not work.

29:10Yeah. It's been a weird, it was a weird formative period. And then the period after has been a lot of sort of unlearning and debriefing and processing. because I was so, I mean, I was so young. I started there like on my 21st birthday, I think. Wow. And so like, I had no sense of like, what was normal? What was appropriate? Yeah. Like how, what were best practices? Which is great in a lot of ways. I learned how to do things in a way that worked, not as like how they were always done. Yeah. And I had opportunities to do stuff that under ordinary circumstances I wouldn't have been able to do. but you know it was also a toxic dysfunctional you know ultimately in some cases like you know like criminal environment that like has there's been a lot of like sort of uh repercussions since but it it it's yeah it was just this weird period in my life it's basically yeah yeah i mean for better or worse is that like you know part of that almost aggregation of experience the fact that it was so intense and kind of, I guess, non-traditional.

30:22Did that add to the ability to write? Yeah, yeah, and you're like, you're, I like characters. It's good to meet and know characters, right? It's not always good to be a character, but it's good to like meet people who are just like extreme, unusual, different, because it helps you understand and see, as you know them, you can see those traits and those ideas in other people, in historical events, in literature. So like when we say you live an interesting life, it's like, okay, you go and you fight forest fires for a year. You're gonna meet all sorts of different people and find yourself in all sorts of different experiences that then if you go decide to be a screenwriter, you're not gonna necessarily write about that, but things that you experienced or saw are gonna inform that.

31:09And so observing certain traits and watching certain things happen and see how people interact with powerful people or important people or how they change based on money or authority, you know, all of that shapes the stuff that, that I write about now. I wrote this book, Ego is the Enemy, as I watched the founder and owner of the company destroy said company in this sort of bit of ego and delusion and self-destruction. Right. And so like the, the things that you experience and see shape what you're able to do. Yes. I feel like, um, like imagine if you guys were interviewing creators, but you'd never been creators ourselves.

31:45You wouldn't be able to do it. We wouldn't be able to do it. And I think I oftentimes think about our career as like we're professional observers. Like our job is to observe and then articulate. And I think that kind of showcases also for all creators that the best advice we can give to a creator is to actually write. Because I think writing is the foundation of everything we're doing. If you look at how people are treating YouTube today, I mean, they are writing and rewriting the first line of their YouTube video to hook an audience, right? And that's writing. We're displaying it and turning the writing into something different, but we are writing.

32:24And I think all writing comes from observation and inputs. Yeah, I was going to say, I think even before writing, some of the advice that we give is make sure you know what you care about before you start writing. Make sure you know the communities that you're a part of that you want to serve. So many people now, like they see the job title of being a YouTuber, but don't have that pre-established life that, you know, have that reason. Like the wall of purpose is a lot of the reason that a lot of creators stop. Yeah. Yes. If you don't have something to say, like what is it that you're trying to say that only you can say, I think you're in trouble.

33:02especially when it gets hard like when the audience isn't there or you know the trend is this way or that way like if you don't know what you're what you have to say it's really hard first off to know if you're saying it but second to like to to have a reason to do what you're doing like if you're just chasing what's popular if you're chasing what you think other people like this is this is not it and it's not gonna work you like the the best creators have something to say they have a point of view. And, and yeah, you also have to sit down and get really good at expressing it. And you can't just wing it all the time, but like, what is, what is your thing?

33:41Yeah. How do you navigate though, finding the thing that works and building a business around that? Yeah. And still being able to experiment or, or do something like, how do you know when to try something different? because a lot of creativity and the business of creativity is like you're experimenting for a very long time. Most things are not working and something clicks. Something works. And then you're like, this is now my, this is the business. And the other people are like, that's the business. Exactly. Because the outside, like stories have to be simple. Yeah. Ryan Holiday, he's the guy who talks about stoicism, right?

34:18It's like, go along on that. Do you know what audience capture is kind of audience capture is like i can assume similar where like so you're doing something and then the algorithm or the audience suddenly relates to that thing and then you just give the audience more and more of what they want and then it's sort of like who owns who you do you control the platform does the platform control you and i think you see this a lot politically like someone will have one controversial opinion or one sort of unorthodox opinion and it'll suddenly like explode either it'll get them canceled or it'll suddenly be like taken up by people who ordinarily aren't interested in them.

34:55And then the next thing you know, that's who you are because that's, what's getting you invitations on Fox news. That's what's sending the algorithm crazy. That's, what's getting negative stories about you, which are still actually driving lots of traffic. And then all of a sudden you're like an internet troll and you're like, where did this come from? It's just like, you just spoke up about this thing one day. And like, I've seen it happen so many times and I'm really cognizant of not doing that, that I try, like obviously the data is super important and you ignore it at your peril. At the same time, sometimes like I'll say things and people get upset and I go like, you had to know this would upset your audience.

35:37And I go, I didn't develop an audience to not say what I think, right? And so I try to remember like why I got into this, which is like the things I want to talk about. It happens to be that a lot of times that lines up with what the market wants. But I've taken like enough turns and done enough things that weren't exactly what you would expect. I mean, even like it seems now, again, clear in retrospect that writing about stoicism would be very popular. And there's lots of people that have tried, there's like hundreds of meme accounts that try to take advantage. There's other YouTube accounts It's like, there's other people that talk about the thing that I talk about, which is great.

36:19But like when I went to my publisher in 2012, and I said, I wanna write about an obscure school of ancient philosophy, they were like, but you write successful marketing books. And I was like, but this is what I wanna write about. And they offered me half what I got for my first book. And so that was a step down in a big way. But part of the benefit of having other things going on in my life was that I was like, okay, but I want to do that. Like I'm not, I'm not, my income is not dependent on solely on this. So I can take some creative risks. So I think part of it, I think it is important to not live or die by like how your thing does today, or then you're, you know, you're not in charge, like the algorithm or the market is in charge.

37:11And I don't think that that doesn't make good work over a long period of time. Yeah. One of our first YouTube videos on this channel was about growth hacker marketing. Really? Yeah. It was like a book that when, when you probably haven't seen it, you probably haven't seen it. I would actually ask you to please not watch it. Cause I think we butchered it. We might have butchered your book completely, but it was a book that I read when I was like very lost about what to do. And I was just starting to read books. And one of my friends recommended it. Who I think worked with you on like a Kickstarter campaign or something.

37:47Was it? Zach Park. Yeah, yeah, yeah, yeah. Yeah, yeah. So him and I had coffee and he was just like, read this and maybe you'll get a better sense of like building an audience. And what's interesting is a lot of the principles in that book, like we still talk about and apply today, whether it's product market fit or finding the right audience. Go above and beyond, like surprise and delight your audience. Yeah. Price disparity to experience. Like there was so much curriculum in that, that I think is applied to the world today. Which at the time that we made the video, we took none of your advice.

38:19We gave it to other people, but we were not taking it. We weren't good at taking that advice. Which is why the next book was Obstacles the Way. That's right. That we read. Yeah. All right. So I wanted to go, you know, back and to just understand your story of how you, how you came to that point of, of talking about, you know, even the things you talk about or writing about the things you write about. That book was interesting. So my first book was called Trust Me, I'm Lying, which is sort of expose of media. And I think I was writing for Fast Company or some online outlet at the time. And I just wrote a short piece about growth hacking.

38:53And my editor at Portfolio, which is my publisher, said, hey, have you ever thought about doing a Kindle single? And I was like, I don't even know what that is. but she was like, well, we're doing this thing where like, you know, your average book is, let's say 50 to a hundred thousand words. She's like, these Kindle singles are digital only. And there may be like 10 or 15 ,000 words. And she's like, just try it. And I think, I think they paid me like$2 ,000 or something like nothing. And it was just really to take this article that was a thousand words and make it 10 times longer. And yeah, the ebook came out, it did well then they turned it into a paperback and they turned it into extended paperback it i don't want to say ironically but sort of ended up following the exact path that i'm talking about in the book which is like we tend to think that creators create from this sort of you know genius comes down from above they know exactly what it's going to be uh and then it immediately resonates with the audience and then that's how stuff happens and because that's how we think it happens First off, people are very intimidated by it.

39:59And second, people waste their time on a lot of things that aren't working or aren't good enough. And in fact, I think a lot of projects are sort of iterative. They develop like that. And what I was accidentally doing there is getting to a kind of product market fit. The article was some validation. The e-book was more validation. The extended version was more validation. And it was getting better as it went. And so the book that, I mean, the book is still in print and still sells now. When someone buys it now, they have no idea. It's sort of like humble, ordinary origins, but it works for them because of the data and the feedback that it got along the way.

40:39And the other big decision that I made, I think like every book project I do, I'm trying to think that's like, here's what I want to write about, but what is the way into that thing? Right. So like, um, as I was thinking about growth hacking, which was at the time, this sort of trendy, not trendy, but a hot style of startup marketing that was very popular in Silicon Valley and a lot of people knew about, but outside of that world, nobody knew about. And so I decided to, am I going to write a very technical book about growth hacking for growth hackers, or am I going to write a book that takes this thing that's popular with this small group and make it accessible to a bigger group, which is PR, marketing, and advertising professionals.

41:22And so that decision, trying to get from here to there to bridge these two things, that ended up being, I think, why that thing exploded. If I'd written about these really technical strategies that people were using on internet startups, I think it only would have been relevant to a small group of people and it would have gotten out of date very quickly. And so by making it broader and more sort of principle-based. That's why I think, you know, 10 years later, it's still selling, even though it was about a very specific moment in time. Yeah. I love the concept of the MVP. Yeah. Like I think you talk about it in the beginning of the book, right?

42:01That it was available for your email list or there was something that it was available at a very low price at first. Yeah. I mean, the article was, the article was free. The ebook was like a dollar. and then yeah the paperback was like 10 bucks or something like so it like if you what's interesting about youtube is it's free to watch youtube videos and so the the reason that most things on the internet are viral is that the cost of discovery is very low right and so you watch a video you like it you can send it to someone else uh youtube sees that a lot of people are liking something they put it in front of other people um so i think when a lot of people transition away from like internet stuff.

42:39Like it's easy to, not easy, but it's easier to get fans on Instagram, fans on TikTok, on these networks where the cost of acquiring the people is essentially zero. And then when you transition towards making stuff that people buy, a lot of people falter because they're so used to this zero discovery cost. So like a book, a book is antiviral in the sense that it takes a long time to read and it costs a lot of money and it takes, people don't like reading, right? Like you have three strikes against you, right? And so with Growth Hacker, but I've tried to do this with all my books. If you think about it, it's like, okay, first off, part of it was free.

43:18Second, it was really cheap. And third, it was really short. And then you could say it's really practical. So I'm always trying to reduce the discovery costs so it can spread. Because at the end of the day, like when you think about why you've read the books that you've read or bought the things that you've bought, but it's almost always because someone you know or follow told you that that was a good thing. So that word of mouth is driving everything. But the problem is you can't get to a large enough audience for that word of mouth to be significant. Like you need, it's like a chicken and egg.

43:50You need 10 ,000, 20 ,000 people to try your thing, to be like, this is good, everyone should eat here. But like, how do you get 20 ,000 customers? That's the hard part. Yeah, yeah. How did you even get to a point where you had developed enough of a passion about growth hacker marketing to want to introduce it to the masses? Well, that's the only book I've ever done that I didn't have the idea, really. I mean, there may be some different exceptions, but most of the time I'm doing the book because I'm really excited about that thing. I had to find out what excited me about that idea. I mean, I was already interested in it clearly because I wrote about it, not knowing it would lead to this, but I wasn't like, this is the book that I should write.

44:30Right. But I don't know. I mean, when when you're working on a creative project, you have to figure out, like, what's the version of this that only you can do? And as at that time, I was the director of marketing at like a big fashion company. And so as I was thinking about growth hacking, it was like, oh, well, what are these people who work in this world have to teach me about the world that I'm in? And so I got really interested and passionate about that. Like I remember, and I think I opened the book with this, but I was, so I was working at American Apparel, which is like, you know, it was a 20 year old company.

45:10It was doing a very old thing, which is sell clothes to people. They're in a building that's a hundred years old. I remember that morning that I sort of heard the word growth hacking. I'd worked out at the Los Angeles Athletic Club. And I was like, this is like Don Draper's life. Like this is like as old as marketing has ever been. And then here these people are using these like key, these like terms and acronyms I never heard. They're doing it a totally different way. And so I was like, that's what's exciting. Like how do I take this thing and tell people about it? And even my philosophy books, it's like I'm really interested in the nerdy philosophy of it, but I realized most people are not.

45:48And so I think I get excited about like taking this thing that's over here, it's not well understood and bringing it over here where it is well understood and accessible and usable and all those things. Is there an early example of growth hacker marketing from your career, whether it was a decision you made or even someone else where you thought, oh, that's interesting? Yeah, I remember at American Apparel one time we had like all these garments that weren't selling that we needed to get rid of. And usually you dump them into retail, into like outlet malls or you just give them away. and I remember I was I pulled up like the hard costs of the garments like what we paid to manufacture them and then what it would pay to ship them and that number was less than what a newsletter subscriber was worth over just one year and so we did this like marketing campaign where you could get free underwear from American Apparel if you just filled out and signed up for this newsletter.

46:50Now, like ordinarily, you know, a small business couldn't do that. Ordinarily, a big business wouldn't spend that much, but it was already a sunk cost. And it ended up not just like getting a lot of followers, but got like a lot of media attention too. And I think, I think I was one of the first advertisers on YouTube. I remember like the big thing about YouTube now, people are sure people watched an ad to watch this video, but at the time the knock against you two this is like 2007 2008 it's like who would ever want to advertise against videos of skateboarding dogs right and i was like we sell dog clothes right and so like we ran we ran specifically targeted ads against the skateboarding dog thing oh amazing and it got like a ton of meat not just like did it actually work i don't even remember but the it wasn't it wasn't like oh this advertising is cheap and it's effective it's oh this advertising is cheap and pretty effective but because it's new and interesting, you get earned media on top of it.

47:49Because people are talking about it. Yeah, so it was like, I already understood what they were doing at these companies. I was doing it a different way. But then the fact that I was doing it and they were doing it, but we were worlds apart, I think was ultimately what I was trying to do in that book. I think what's empowering for me when I hear those stories is that it's the idea that holds weight and is valuable. Not the old structures, not the money. And I feel like even when I was first introduced to the idea of YouTube, that's what was exciting. Was that like, I could sit at my desk and if the idea is good enough, it will travel.

48:21Yes, yes. Although it's like, I talk to people now and they're like interested in YouTube, but they don't wanna do, they don't wanna figure out the logic or like the incentive structures of the thing. Like I think it is the idea and then some people think it's only the idea. True. And it's more than that, right? And what I'm trying to say in Growth Hacker for sure is like, just because it's a good idea. Like there's this Emerson quote actually says, like, if you build a better mousetrap, the world will beat a path to your door. That was what he, he writes this like 100, almost 200 years ago. But it's not true at all, right?

48:58It's not like if you build it, they will come. There's tons of great undiscovered stuff out there. That's the reality of the world. And there's tons of terrible stuff that everyone knows about. And so you have to make great stuff, but you also have to figure out how to get great stuff in front of people or that word of mouth won't happen. So that it comes back to that same problem, which is like, if people don't see it, how can they tell other people about it? And so you have to you have to figure out how to make great stuff and be savvy and creative enough to like jumpstart that process. what was it about stoicism at the time that pulled you away from what was working in the career that you had always wanted well so i had been introduced to stoicism like before my marketing career so that was what i was interested in that's what i loved and when i read mark's realist's meditations for the first time i was like this is what i want to write like i didn't know you could write this way i didn't know these books existed i didn't know that this advice like that's what i it hit me so much personally i was like this is my thing this is what i want to do and I started blogging about it, but no one cared.

49:58Um, when I, and then I had this marketing career and I knew that that wasn't what I wanted to do forever. And so writing that first book, I was not intending to create a career of writing marketing books. Like that was my attempt to leave that behind. And the fact that it was successful for basically two, uh, one big book and one smaller book in a row, that's where that capture comes in because you're like, well, I'm going to not do that anymore. Right. Like I'm going to take this turn that, that there's an opportunity cost for that for sure. My publisher told me, uh, later, like many years later, they were like, they were like, we just hoped you would write this one stoicism book and then get it out of your system and go back to the other ones.

50:44Right. So it's you, I think you have to have a strong sense of like who you are and what you want to do. And ideally like that North star for you should not be what other people like or what does the best. It might be, those things might line up. Like if you're a musician and the kind of music you like happens to be the most popular music, great. But like, if you're calling as opera, like do opera, even though you know that if you applied your same talents and skills over here, it would be a hundred X more popular. That's a hard thing to do. It's very hard. That's super hard. Yeah. I wonder if, you know, kind of back to you at the talent agency and, you know, kind of in that world of working with Robert Green, like, was it very intentional at the time, and I'm assuming so, that your income wasn't, you weren't betting your income on writing?

51:38Yes. I mean, I do think early on in your creative life, it's good to not need a lot of money. Yeah. I remember when I took the job at the talent agency, they offered me$30 ,000 a year. And I remember thinking to myself, what am I gonna do with all this money? You know, like that was a lot to me. And when I sold my first book, I was like, this is obscene. You know, like, so I didn't, there wasn't some lifestyle that I was trying to live that to deviate from that would be, like feel like suicidal or something. Do you know what I mean? So like, if you live below your means, you have more creative freedom.

52:18If you spend everything you make as it comes in, then you're not gonna do something that you are creatively interested in, but you are uncertain of how it will do. It's something that we talk about and that we talk to a lot of creators about, which is as you start growing as a creator, you take on a lot of overhead. Yes. Right? And even we told you we're moving into a new office. It's the most expensive office we've ever had. Yeah. And as you build team and fill that office, you're like, wait a second, I have a fixed monthly cost now that I don't have a choice, but to make sure those bills are paid.

52:52Yes. Now your creative is attached to your overhead. Yes. And I, I, I think like it happens faster than, you know, as a creative, because it's, you go through so many years of scarcity. Yes. And then when you reach abundance, you're like, it almost is, it's so new to you that all of this is happening. I do. This is one reason I do advise people to like find, it's not necessarily the best idea to New York, Los Angeles. And that's where you do your thing. That's not, it might be creative, it might be interesting, but like it makes it a lot harder to be you because you, it's expensive, right? Like when I decided, so I left American Apparel sort of full-time, they kept me on partly when I was gonna write my first book, I moved to New Orleans and my rent was$900 a month or$700 a month.

53:43and I was like, I've got a year. I can, you know, I can get a year to write this book. And if it works, great. But if it doesn't, like, I didn't like blow up my life to that degree. You know, it gave me more runway basically. And I think that's really important. You know, it's hard if you are trying to make it as an artist and you're living this sort of mythical idea of what an artist's life is like. In one of the most expensive markets in the world. Yeah. And you're emulating, you know, how they lived in the fifties or sixties or set, like it's, it's, that's not real. Right. And you've got to find a way.

54:24I, I just think runway is really important. It always takes longer than you expect. My first, my first book, that's why I kept a day job for the first three books that I wrote. Um, and actually I didn't leave, uh, American girl fully until like it goes the enemy was almost done. So that would have been my fourth book. Oh, wow. but I, like the books have sold really well now, but like it was a steady client. It was not, I think everyone thinks I'm gonna put this out and then it will explode. And trust me, I'm lying, which is my first book. It came out in 2012. So I sold it in 2011, the way publishing works, you get an advance, and then it's an advance on royalties.

55:06That book earned out its advance and that book sold, I don't know, almost 200 ,000 copies. That book earned out its advance like this month. Oh my God. So like it was - How many years is that? It's 11 years. 11 years? So like it - So now you make money from that book. Yes, but like if, let's say that's the only book I had written, that means I made like$20 ,000 a year for 10 years. That's not, so like it takes like - Yeah. To develop a body of work in an audience, you can't look at the people who just put up one thing and then have 20 million followers. That is not what's going to happen for you.

55:42Like I bet if I looked at your subscribers, it's a slow, steady climb. There might be big spikes, but you did not get where you are now like a year in or a day in. That's not how it works. It takes time. It took us, I mean, honestly, it's taken us 10 years to understand this platform and we've done nothing else but YouTube for 10 years. Yeah. I think now, like you mentioned before, or like now we do understand the incentives of the platform. At first, we just thought we were expressing ourselves creatively and that was not what was happening. It was what was happening. You were expressing yourself creatively, just not that many people were receiving.

56:16Exactly. We didn't know how to get people to receive it. Not to a scale that deemed it a business. Yeah. It takes long. So the more space you can give yourself, the better you're going to do and then the less you're subjected to that pressure, right? Like I did, trust my mind, okay. I wrote my first philosophy book, did okay. But I was already writing the next philosophy book. I didn't really care how it did, right? Like I just knew I was writing and making things that I thought would work, but I thought would take time to work. And I also wasn't like starving. You know what I mean? How old were you at the time?

56:53When trust me, I'm lying. Trust me, I'm lying. I wrote it when I was 24 and it came out when I was 25. So I think. And how did you, I've always wondered this, how were you trusted enough to become like a marketing executive at American Apparel? Well, like I also advise, yes, like I didn't go to a hundred year old fashion brand. Yeah. Like, you know what I mean? I, one of the things that is beneficial about working at a startup or a scrappy company or a dysfunctional company, which is what American Apparel was, is that you can move up faster than you ordinarily would. So again, living interesting lives, taking risks, you can rack up experiences that under ordinary circumstances would take a lot longer.

57:39You know, like you wanna go somewhere where like you're in the room where it's happening and they're not usually gonna let a 22 year old into the room where things are happening. But if you take risks and you're willing to do this, then you're front loading some of that experience, I think. I completely feel that way with our career in lacrosse. We were given opportunities at the age of 22, 23, 24 that generally were held for people who were in their 40s. Like we got the live rights to the professional league to put them on our YouTube channel. And Samir's also doing the switching, the live switching in the back.

58:15If you were doing an NBA channel, that wouldn't have happened. Yeah, we picked a world where we could enter in and have those experiences. Where there was opportunity. There was opportunity. Have you guys read Blue Ocean Strategy, that book? It's a great book. But the concept is like, you go where there's like blue ocean, not red ocean. I wrote this book about Peter Thiel a few years ago and he had this great line. He said, competition is for losers. So like you go where you're the only one doing that thing. You have to, you don't just go to the only one, you're the only one doing that thing. If you don't like that thing, you have to find the overlap of like what you're interested in and what you're excited in and where there's not a lot of people doing that thing, which is the funny part about stoicism now.

59:02Like now that my books have sold and they've gotten media attention and there's this big platform, it's safe. And so people are like, well, I want to write a book about that. I want to do a stoic parenting book. I want to do a stoic insert book. And then they assume that it's going to sell just like the other books. And they don't realize that they're competing with the other books. And that's actually a much harder thing than if they'd found some other niche that was fresh. Yeah. I think that's really just a very good topic when it comes to YouTube, because I think right now, I mean, the most desired career is to be a YouTube creator.

59:39Yes. You look at YouTube and it's like, where do you find your wedge, right? Where do you come in now? And a lot of it is stealing like an artist, not to quote, you know, Austin Kleon, but it's, you know, looking at what's working. And essentially what we've learned and even in reading that book, I mean, quite frankly, we were essentially making Casey Neistat vlogs for our first, you know, two years of existence. It was like trying to reverse engineer how he was doing that and being like, how is he telling stories about himself? Because when we went from telling stories about lacrosse to trying to make a channel called Colin and Samir, we couldn't understand how you told the story about yourself when the subject wasn't something that you understood why it was interesting.

1:00:21like we understood why lacrosse was interesting and who the audience was when it came to telling stories about ourselves we didn't even understand ourselves that's the hardest thing i uh people come to me they're working on books and i go your pitch is literally the hardest pitch that you could possibly imagine which is here's a memoir of a person you don't know about right like yeah who wants to hear about the life of a person that they don't know about right and then how are they going to hear about this life of a person they don't know about that's extremely hard yeah but If you have found a way to do something really interesting or really unusual or you're exploring, you have, what is, what's the way into this, you know?

1:01:00And I think people struggle with that. It's, there's a self-indulgence to like thinking. It is kind of main character energy to a lot of people who are attracted to any of the creative professions. And you have to have that, but you also have to have an empathy. Like you have to be able to imagine what it's like to be an audience member, which is to have an unlimited amount of content at your fingertips and not that much time. And like, how the fuck are they supposed to hear about it or care? And I think that's what was so interesting about coming across your books because recognizing, like Colin said, we thought it was just expressing ourselves.

1:01:35But actually a lot of the principles of marketing is what you need to find success on the internet, right? You have to have a very deep understanding of how people interact with stories. And did you practice writing and do you still practice writing? Like writing a book to me is one of the most daunting things I can think of. Making a video, not as daunting. Making a podcast, not as daunting, right? But writing a book, which is something that's a goal of ours, but it's the most daunting thing. I have emails that I haven't responded to from our agent asking like, how are we doing on our proposal?

1:02:09And I'm like, I can't even look at this right now because it's so daunting to write. Yeah. Is it that you don't know what you want your proposal to say? I think I know what I want it to say, but I'm not in the practice of writing at all. You know, the practice of crafting sentences and actually being able to communicate through words on a screen is something I'm not in practice. I feel like I have fear of my ability when I start right now. But I know that there have been times in my life when I have been in the practice of it, but I am extremely out of practice. That's interesting. And I think a lot of creators like...

1:02:48You know, it's scary because you think that everything you film, you have to put out. Yeah. Because of the pace of output right now. And I think there's so many videos we haven't uploaded and you recognize like that is us essentially practicing. And earlier this year, I took improv class for the first time. And I was like, oh, this is a space I get to practice performing, practice reacting to someone. And I didn't really recognize that practice is not that big of a part of my life it's more of actually the the performance of it or like the stakes are always there when i'm doing the thing yeah i think with writing what's interesting about i have a a quote on my wall from hemingway says the first draft of anything is shit yeah and if you get comfortable with first drafts writing is much easier if you think it's supposed to be perfect when it comes out, you're going to get blocked up, right?

1:03:48So I try to always be writing. I think quantity is a way to get to quality. So like I do this email every day, the Daily Stoic email, and I've done that every day since October, 2016. So that's roughly a book, a book and a half a year by word count for free every day. um i've also done roughly a book a published book a year but those books are better because of the daily practice of the other thing about it and so the it's like a comedian it's like how often are you getting up like how often are you going on stage and doing the thing um if you're always doing it i think you get better so i don't like sit down and practice per se like i'm not sitting down at the piano and just playing.

1:04:37But I've set up my output or my system in such a way that I'm doing it often enough that I'm just getting a lot of hours in doing the thing. And I get better at it, tighter at it. I get to noodle with stuff, I get to try things out. You know, like there's chapters in the new book like that started as Daily Stoke emails or started as articles and they worked. And it was like, okay, I'm gonna explore that or expand that or things that I remember I did. Like I have like a place that I'm doing stuff that I don't have to be, I mean, it goes out to a lot of people so I can't just like half-ass it, but I don't have to be so precious about it because it is an everyday thing.

1:05:19Like if you're a Hollywood director, like how many of those do you get to make in your life? Like maybe three, maybe four. And that would be like extremely lucky. So like, how do you have other creative outlets where you're building the muscle and practicing the thing? I think that is really important. It's interesting now because the world of video also has both short form and long form video. And short form video is a much lower barrier to entry. You can make it with more consistency. And as we started to make short form video, we started to recognize we had to tell more condensed stories and learn actually omission, right?

1:05:52What do you omit from a story to fit it into 60 or 30 seconds? And then as you make long form videos, you look and you're like, well, I could actually omit that. That doesn't need to be in there. I can get to the story quicker. Sure. And in the practice of making short form video actually informs you were mentioning before we started recording our intros. Those intros kind of come from the practice of making 60 second videos, then applying them to, OK, actually, the first 60 seconds could be a condensed origin story of this person. That actually would allow us to skip over a lot and get to the meat of the conversation quicker.

1:06:24Right. If we tell their origin story in 60 seconds. Now we're into the learnings from this person. instead of doing 12 minutes of origin story in the beginning, right? So it's - It's like my favorite medium is books. Like that's what I love. That's what I love to consume in. And then realizing that everyone else has different mediums, like some people like social media, some people like Twitter, some people like email, some people like audio. That's been helpful for me on deciding, I made the decision with Daily Stoke a couple of years ago to be like, I want to be in all the formats that are possible or a lot of the formats.

1:06:58and then having to go figure out those mediums and figure out how to like get good in those mediums it creates i think as you said the different constraints of each section challenges you right you have to figure out that you can't just be like i am who i am i'm going to do it over here you have to go like well how do how can i make what i do work over here yeah right it's like learning another language but in learning that other language you find different concepts or words or ways of expressing what you do that makes you better. And you get the added benefit of reaching all the people that are only in that medium or whatever the power of that medium is.

1:07:36Like I don't watch very many YouTube videos. My kids watch YouTube videos. I don't watch that many YouTube videos. That's not like I don't sit down and watch a 40 minute video about something. I would like to go, if I have 40 minutes to think about something, I want to read a book. but understanding that a lot of people do do that I have to figure out how to take what I would maybe ordinarily put in a book and make something that they can like my favorite thing is when you hear from people and they're like I haven't read a book since high school and I read one of your things like you realized you crossed over and you reached into the medium or a kind of person or a a lifestyle that ordinarily wouldn't consume your stuff.

1:08:19Or I heard about you on YouTube and then I read your books. You're like, that's what you want. Totally. I think what's interesting about your career is so much of it has been about taking things that are not new, but just introducing them to new people. And obviously you make them accessible and you make them interesting and you add the story for the modern landscape. But I think that's such a transferable lesson for creators is that a lot of what's happening on social media right now is not new. It's good stories in a slightly different way. Are there even new stories? Right. You know, like, like, uh, Star Wars is not a sci-fi movie.

1:08:55It's the hero's journey. Yeah. Right. And like, when you realize that most great art is rooted in some timeless thing, it's a coming of age story. It's, you know, whatever it is, then you go, oh, okay. Like, Like, yes, what I'm saying is new, but if I can tap into an old form or style, then it's going to be less intimidating to people. They're going to get into it faster. Like you said, like you do the intro so you can get to the meat of the conversation faster. You don't just go like, oh, I'll let the story go where it goes. You go, oh, no, let me put it on this proven arc so then people can actually get the message that I'm trying to get across.

1:09:36yeah it reminds me of when my brother uh gifted me meditations by marcus aurelius i looked at it and i was like there's no shot i'm reading this and put it down it's like an the statue of an old guy and i was like i'm not this is has nothing to do with me and i shelved it you know man and i came back to it yeah because of daily stoic because daily stoic the thing about daily stoic and even growth hacker marketing is the dopamine release of finishing yes is immense for me So finishing growth hacker marketing was my experience of being like, I just read a book. Holy shit. You know, that's crazy.

1:10:13And then daily stoic, you sit down and you're like, if I don't have 90 seconds to read this, then something's wrong in my life. But you can read a page and you finish the page. And then that's like the on-ramp. And I think sometimes we overlook that the on-ramp, right? I kind of discovered that on accident. I obstacles the way, I don't remember why I settled exactly in that format I think it's because I started as a blogger and you know you write like a thousand two thousand words like that right and so I was like I'll do lots of smaller stories I really like this book The War of Art if you've ever read that by Stephen Pressfield his are even shorter somewhere like this but um after I wrote The Obstacles Away I would hear from people they're like I finished your book on the flight from you know like New York to LA or something and and that idea of like finishing something on a plane is something i think about often because you would only do that for something you really loved right like you would only like you you don't get distracted by the screen or sleeping or you just bang through it um and so by artificial not artificially but by deliberately making it short and tight impossible for that it feels like the reader is thinking, oh, I just read a book that was so good.

1:11:27I blitzed through it on a plane. They're not going, but how long is it compared to most books that I would read on a plane? Do you know what I'm saying? So the feeling of finishing is really, really important. You're setting up a headline that allows someone to share it. It's like baked in marketing, right? Like Samir handed me obstacle is the way right after he finished it, right? Yeah, right. That's great. Yeah. And I think, um, which is like thinking like a distributor again, which is like, you're not just creatively expressing yourself. You are making some deliberate decisions. And maybe that one was more after the fact, but there are parts of this process where it's like, yeah, it's not just about what you make.

1:12:03It's about how it's going to be shared, how it's going to be delivered. Well, like a five minute indulgent sloppy intro versus a one minute tight compelling intro. You now I finished the video faster. Yes. And I can share it faster. And I also it went by faster and I got sucked in faster. You're setting people up for success by doing the work for them. Like so many people will be like, so what are you working on? And then they'll tell me like some like, you know, seven minute story about their project. And I'm like, you can't tell it to me quickly. And like, that's going to be reflected in the final product.

1:12:40And then the consumer, if there is one, is going to be like, so what are you reading lately? And they're like, oh, I don't know what's this book. And it's like, I love this. And yeah, like, it's not like, you have start with why there. That is so perfectly done. Yes. Start with why. And some of my books do it better than others. but even if like the title itself, the concept teaches the lesson, and then the thing is just a deep dive into that lesson, that's better than like, like when you see people will have a book and it'd be like the blank paradox or like, or whatever. And you're like, so you haven't figured it out.

1:13:21That's not, that's probably not going to be a clear takeaway on this project. I find it so interesting. There's so much that relates to books and YouTube videos. Like what we're talking about right now is retention, which is such a big part of YouTube is like, how do I retain you for the whole time? Right. And, and you know, you're talking about that when it comes to a book, right? Like you're getting a hundred percent retention on a plane and like quick, you know, finishing. It means that you hooked them and each chapter hooks them to the next one, to the next one, to the next one. And even like titles.

1:13:52Yeah. I was going to say titles and thumbnails in terms of like putting the obstacles the way on the front. Like you are judging the book by the cover. And can you, how can you make it like what I think with obstacle being, having short chapters or the daily stoke is one page a day. Like how many books does a person read twice in their life? It has to be really good for it to read twice. But if you, but that's also because most books are only designed to be read once, right? Like it's just beginning end. It's not supposed to dip in and dip out. And when you read meditations, like it's just like a collect it's meant to be that so that's why you return to it over and over again and so to to really think about how do i make something that's not only accessible and you can finish but lends itself to repeat a repeat or an ongoing relationship that's really important too yeah and yeah if you're just sort of oh this is what i was thinking about doing and you're not coming back and tweaking and changing all you're not setting yourself up for that order yeah and you're asking a lot of the consumer.

1:14:57I want to actually double click into pace. Okay. Because I think pace is a, um, is one of the biggest challenges for creators today where the expectation of pace right now, even for us, right? Like we, we were on a call with a couple of creators and we were talking about how we felt we were, um, lacking in frequency right now. And one of the creators said back, he said, hold on one second, you put out two podcasts a week, one YouTube video and three newsletters. Yeah. And you feel like you're infrequent. And I do feel like we're infrequent. Sure, sure, sure. Right? I feel like we aren't that as frequent as we could be.

1:15:33And on top of that, we also put out stuff on Instagram and TikTok and Twitter. And we are, you know, essentially omnipresent. But I feel like - We're doing something almost every day. We are incredibly available. We're incredibly available. But I feel like based on the expectation of pace right now and output, we don't exist some days. Right. Um, and that, that I think for a young, you know, creator, we're living in a world where you control, there's a permissionless creative environment. You can put, no one's ordering, you know, X amount of episodes of the Colin and Samir show. We're just, we're deciding how much to put out.

1:16:06We could put one out every day. Sure. So how do you, in that like, you know, world of just permissionless creativity, how do you dictate pace and, you know, figure out output? Yeah, it's hard. It is hard. Um, yeah. And it's like, it's who's deciding. Is it you or is it, are you picking up? It's like, are you thinking that, hey, we should pick up the pace because we're capable of more and it would be good to do more? Or is it some sort of comparison to somebody else? Like we should do more because other people are doing more. And I think the former is justified. Well, you should be trying to, like, it's like if you run faster and you're holding yourself back, maybe you should run faster.

1:16:53Obviously not to the point of injury, but like it's good to try to get better at a thing. But if it's just this sort of nebulous, like, well, why not? Or because other people are doing it. To me, that's not a good reason. But that takes discipline to be like, this is the pace that I'm on and I'm sticking to. I'm not going faster or slower. I interviewed this mountain bike racer. Her name's Kate Courtney. she was in the Olympics this year and she was saying that like her coach will give her like a workout like hey you have to you know ride like 30 miles at this pace today or whatever and because you're competitive you're driven you're like I can do more than that and she would find herself like pushing past the work and to be today is a rest day you're not supposed to ride and she would want to ride and he would say do you want to be fast now or fast later like do you want to be do you want to win practice or do you want to be in the peak physical conditioning that you need to be at the race that we are training for and so sometimes i find myself taking like the wrong things serious like so i'm really concerned about the output but maybe that's coming at the expense of like did i sit down and do the writing that i should do today you know yeah and the output is driven the i want to do the output why because it's i can see how many views it did or because other people are doing more, those are not good reasons.

1:18:16So I, it's, it's a balance. It's a balance. You shouldn't be doing nothing, but you shouldn't be doing an unlimited amount. I love the notion of discipline about rest. Yeah. I think that's something that is incredibly hard in today's creative environment because again, you are in a race where it feels like everyone else is producing more than you, or if you're resting someone else's, you know, and it's a very confusing thing to navigate. Like, how do I stay disciplined about both rest? And then what we were talking about was, you know, again, we also need to be disciplined about living an interesting life.

1:18:50Yeah. If we don't, we don't have any, like, we're not going to have anything to talk about. Oh, it's hard. And that's in the military, they talk about sleep discipline. Like you even, like, you have to have this amount of sleep, like, and like, that's not something you sacrifice. Yeah. Right. And so like, I think like all nighters are bullshit. You know, I think like two week sprints are usually a result of like not having planned, you know? So like I'm, I'm, I, I have tried to develop like a quick, but sustainable, like day to day pace. So if I show up and do what I'm supposed to do, it creates this certain amount of output.

1:19:26I think the problem is people are like not disciplined about the way they create. And then they have these like absurd or unrealistic output goals and that's not going to work. It's like you had a year to do this project and then you wasted the first eight months and then you're trying to do a big, a year project in four months. That's not the way to do it. It's to show up every day and work on the thing. Like I do an email every day, but I don't write an email every day. I, I write lots of emails on some days, you know what I mean? And it's batched and it's a process. So I've tried to create it it as sustainable and and i and you have to get good like you you start usually as an individual creator like i write articles or i make videos i film it then i edit it blah blah blah but as you get more successful it becomes a system it becomes a team and then really developing a system and a team that allows you to do what you do and the other people to do the other parts of what they the things that you don't want to do or shouldn't be doing.

1:20:34And that creates something that scales also. Was building a team a seamless thing for you? No, it's always by trial and error, right? And then, yeah, it's definitely been by trial and error for sure. I have tried to, like, I try to think about, like, what are the things that only I can do? And then I want to do those things. And then I want to have people do the other things. I love how much some of the, like stoicism and your books have translated also into athletics. Like I know that in NFL locker rooms, they read Obstacles the Way, right? Like that is, I think it's Bill Belichick or the Patriots who famously, you know, talked about that book.

1:21:14Definitely not what I thought or the publisher thought when I was like, let's do this obscure school of ancient philosophy. But I think it's anyone who's trying to do something hard can learn from this. And I think I would prescribe your writing to any entrepreneur or any, you know, creative who's trying to do something hard. And as we get into this topic of discipline, I would say the thing that I didn't anticipate as we went from a place of scarcity for five years of making with basically making no money, but making a lot of content and really struggling to a place of abundance where we have opportunities every single day in our inbox, the discipline that I'm struggling with right now is how to say no.

1:21:53Oh yeah. How the hell do you say no when like you you couldn't have ever dreamt, like you couldn't dream of these opportunities that come in your inbox, but the work you have to do, like the work we need to do is make really good videos. And that requires us to sit here and really dig into the process of making videos. But the amount of times we've been invited to Dubai to speak is out of this world. And we, we haven't said yes yet. And we keep laughing that one day we'll say yes. But I mean, absent of that, we say yes to a lot of opportunities right now because they're really exciting. And that has taken a hit on our video making process.

1:22:29How do people stay disciplined or how would you suggest you stay disciplined as you grow as an entrepreneur, grow as a creator and get a lot more opportunities, but it pulls you away from the practice. It's the hardest thing because part of what was motivating you in the first place was to get those opportunities. Yes. I try to remember that I actually love doing the thing. Like I love doing the thing. Some people, it was always a means to an end, right? And so if you love doing the thing, the reward for it or success in it cannot be not doing the thing. You know what I mean? Like I like writing.

1:23:07So if because of the speaking opportunities and consulting opportunities and building a platform and blah, blah, blah, the result of that is I don't have time to write. Like how successful is that? Like if I don't have control over my day, am I really successful? No, I'm not. somebody else's is benefiting from that success right and so for me having having the space to do the thing that got me excited in the first place is really really important so i i i end up saying no to like most things but i found during the pandemic when suddenly there were not as many things being offered that oh i'm better at this now like i'm better at writing because I'm less busy.

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1:24:40How do you say no? I find that even sometimes I just say yes because it's too hard to say no. So I just ignore a lot of stuff to be perfectly honest. Like, like just because like, if somebody, like I didn't give you my email, not you guys. I mean, like somebody found my email and invited me to be on some thing, right? Like I, I have no obligation to respond to that, right? Like I didn't ask for it in the first place. So I think it's, you, you have to be comfortable just like ignoring stuff. Like, cause if you didn't know it was there, you wouldn't miss it. Right. Um, so ignoring stuff is a huge part of it.

1:25:21Uh, realizing that like, no, is a complete sentence, you know, like, so it's not just like, Hey, I am, I'm going to try to tell you this story about why I can't. You're setting yourself up for them to try to convince you why you can. Right. So to just be like, I'm, I'm, I can't like, or sorry, no, or even not. Sorry. There's a line I have in the book, Sandra Day O 'Connor, the Supreme Court Justice, one of her clerks said, what I always admired about her is that she never said sorry before she said no. She just said no. It's amazing how uncommon it is in person to just accept a no. I've tried that a few times with getting invited to parties or dinners where I just go, oh, no thanks, I'm not interested.

1:26:06And the look on people's face is like, you hate me. And I'm like, oh man, I really did not mean that to come off harsh. I just don't want to spend my night doing that tonight. Yeah. But still, even that, like a softer version without a reason. Colin said to me, sounds different. I think a year ago, he looked at me and he said, don't invite me to things. Yeah. That's what I said. It sounds good. I don't remember. I remember I was with someone once and someone asked me, and he was like, hard pass. And I was like, I love that. Yeah. Hard pass is good. Not just like I'm not interested, but don't even talk to me about something similar to that.

1:26:42Like, let me vehemently say no to that. But then also like creating barriers, boundaries, and systems that filter stuff for you. Like, this is why people have agents. This is why people have publicists. This is why people have assistants. Like, let somebody else be the bad guy for you. And yeah, that sounds like a little bit privileged, but it's also inherently a privileged position to be able to say no, right? Like early on in my career, I didn't have someone to do that because I was default saying yes to everything. you worked really hard to get yourself into a position where it was, your time was worth something.

1:27:18You then have to protect that value. You can't just give it away. One of my favorite things from Seneca, he goes like, look, if someone like stole your money, you'd be upset. Someone built on your property, you'd be upset. But then you're much less defensive about the one non-renewable resource that there is, which is your time. and so like i don't i don't fucking get on the phone for no reason i don't like let people pick my brain you know i don't really agree to meetings and then like i have like people like in the systems like if i'm doing a talk i'm not was like oh and then i'm doing oh we need you over here we need you like no this is what i'm willing to do and i'm i'll be a hundred percent for that but i'm not going to be like drawn into this other stuff because that's coming at the expense not just of my work, but like having kids was really helpful because then it was like, oh, okay.

1:28:13My default promise for my time when I'm not like making a living is to my children. And I'm not going to steal that time from a three-year-old who's going to cry. So I can give it to you to have some phone call that really should have been an email that by the way, I wrote an entire book about that you could have just read, right? And so sometimes by our reluctance to be rude, we end up actually being very rude to people that we shouldn't be rude to. That's really good. Yeah. Like you'll steal time from yourself. Yeah. That's fine. But like you got married. You like you gave that time. You committed to a certain amount of time.

1:29:02You committed to making someone else a priority. And then here you are. Actually, your priority is your email inbox. Oh man, that's like hitting too, too close for me. That's, that's really good. So I want to shift gears to the kind of the business of creativity and talk about you've, you've seen this all the way from signing your first, you know, YouTube creator to, um, today being a career creative. What, what do people need to know about the business of creativity, especially a young aspiring creator who wants to base their career around the output of their own creativity? I, the more you own your audience, the better you are.

1:29:38And so I'm always nervous when I see like social media people and how many layers there are between them and those people, right? The algorithm giveth and taketh away. Yeah. Right. Like, so like what I love about newsletters and that's why I started the daily stokes and email a day is that there's no one in between me and those people. I like all the other platforms, but ultimately it's about driving them back to the thing where I have a direct audience. And then one of the tweaks I made actually starting with the first book in the series is like, I opened a bookstore in 2020, I guess 2021. But part of that process for me, part of why I was doing it was I was tired of walking into bookstores, even though my books had sold millions of copies and being like, this bookstore doesn't have my book like they don't care like they're they're in there they just don't care and so like i wanted to sell as many of my books directly to the audience as possible i still work with a publisher for a lot of reasons which you don't have to go into but um i like okay so with courage is calling so typically the way it works in books is you put out the book, you announce that it's coming out, and that all your pre-orders count for your first week of sales.

1:30:58So everyone tries to get lots of pre-orders, then you can qualify to hit the bestseller list. That's the whole model. Why people often sell to companies, right? Yes, they do book orders, they offer bonuses, whatever. They're all trying to do pre-orders. But it's to get this arbitrary thing that you don't control, which is the New York Times list to the Wall Street Journalist. I made the decision to sell the books directly for the first one. So like, you can still order it from everywhere else, but if you want to buy it from me, you can buy it from me and I'll sign it. And the reason I did that is I'm doing this four book series.

1:31:36I was tired of directing people to other retailers who then had the relationship with my reader, right? Like there's people who sold millions of books. They have no idea who those people, They've never actually interacted with their customer in any way. And so the first book, you know, pre-sales were great, did them directly. The second book, the pre-sales are better because I told all the first people, like, I know you bought the first book. Do you want to buy the second book? And by the way, I can sell it almost as cheaply as any other retailer because there's no middleman. So I think the long strategy, and obviously to start, you have to be willing to take any opportunity to get in front of people as possible, but you have to be moving towards owning as much of your material as possible, but next to that, owning as much of your audience as possible.

1:32:29Owning the distribution. Yes. How much of a risk is it to open a physical bookstore in the age of Amazon? It was not cheap, I will say. And it certainly in March of 2020 felt like a very terrible idea. But getting out to the other side of it, it's been awesome. And now there's a place people come from all over the world to like see it. And I needed space anyway to like record and do stuff. So it's, the math is worked out. It was definitely a big bet on myself, but to me, it was consistent with the idea of like, I want to control the distribution channels as much as possible. And a lot of the value there is that that's almost a community hub or it can be physical manifestation.

1:33:10Yeah. Yeah. Um, back to, back to kind of like the early days of the business of creativity. A lot of creators ask us about how to price themselves. I'm curious if you have a perspective on that, you know, even when it came to speaking, when you did your first, I think I heard you and Seth maybe talk about speaking. I don't know if you've, have you done a podcast with Seth? I don't think so. I mean, I know. So then maybe it was Seth and Tim Ferriss, we're talking about just kind of what you're offered is your rate. And then you build from there. Is that your perspective? Like if a young creator is making videos and advertisers like, Hey, I'll pay$800 to be in this video.

1:33:42Is that your rate or, or do you develop a price? I would say, okay. So two part question then the work itself, you want it to be as cheap as possible to build as big an audience as possible. And then you, I think you want to have premium stuff from there, but generally the, the, you're not trying to make as much money from each person as possible. That's not a strategy to get to scale. And then when there's the other stuff that comes on top of it, whether it's like a consulting or speaking or appearance, you're almost certainly, whatever your instinct is to charge, it's probably less than it. I mean, there's exceptions, but like you're almost certainly undercharging.

1:34:22And this is, this to me is where representation is so important because they're not only are they going to ask for more than you are likely to ask, they have access to what other people are getting. And that's really the key. Like every once in a while it'll happen. Like someone will email me directly and they'll be like, which isn't how you're supposed to do it. They'll be like, hey, will you come talk? I can pay X or we don't pay for this event, but we'd love to have you talk and I'll forward it to my speaking agent. And it'd be like, they just booked one of my other clients yesterday for this amount.

1:34:57That's a lie they told you because everyone's trying to get the best deal possible. But like, there's no universe in which, when I hear people are like, I do it myself, I am always mystified at it. I think it was your quote, only a fool represents themselves. That's a very famous quote. It's also for like people who represent themselves in court. Got it, got it, got it. I have a question about focus. I feel like a lot of what we've been talking about is around the idea of focus. Even when it comes down to being disciplined about like when you have time to focus, How much of you moving to Texas has been about focus?

1:35:34Because you talked about earlier in your career, you were in New Orleans. Don't be in New York or LA. It's important. Have that runway. But now you're well into your career. And you're also still not in New York or LA. I would say it's a big part of focus. It's a big part of saying no. Like we're talking about saying no. It's easier to say no to things that you would have to get on a plane to go do. like if it's 15 blocks away it feels more self-indulgent or selfish to be like no i don't want to come to your dinner party like right it's like people don't ask me to do stuff because they know i live a thousand miles away right which is on purpose where i live i live about 45 minutes from austin but it's just far enough right that i can do anything i want in austin but i'm not expected to do everything in Austin.

1:36:19And that's really important. Um, I would say, sorry, this is just a talking too much cough, not a COVID cough. Um,

1:36:35what was I going to say? Um, oh, uh, it's, it's, it's about focus, setting up a life you want, you know, things you want. I couldn't have opened a bookstore in LA or New York. I just wouldn't be able to afford it but uh it's also i like not being around people who do what i do that creates a buffer and ability to focus like when you're around this is also like i remember i was in like a facebook group with a bunch of speakers once and i was like i gotta get the out of this group uh because it's just people talking about how much they're working how much money they're making and so instead of being more than content and happy with what i have which I was, I'm comparing myself to all these other people.

1:37:19Like I live in the middle of the country. Like I live in the country. Also it happens to be in the middle of the country. But the point is none of my neighbors are writers, you know, they don't care, right? Like we're talking about like fences and stuff, not like I just saw you on X, right? Or how many copies did, like there's no concept of that. Yes. Of why that matters. Yes. Yeah. So that also helps me focus on doing what I want to be doing, not what I think everyone else is doing. I really love that because that's a completely contrarian point to what people believe right now in the creator economy, which is in order to excel, surround yourself with creators.

1:38:02So you can learn at 2, 3, 5x the speed because you have five people in a room. You still do that? I talk to people all the time. I see whatever, but Austin Kleon told me once he said, I remember when I moved to Austin, he drove me around and he was showing me stuff. And he had kids then and I didn't. We both, I think our first books both came out like on the same day or something. And he said, work, family, scene, pick two. The work, family, scene, pick two. Are you going to be like around a lot of creators? Are you going to be like, see your spouse? Are you going to do a lot of good work? and you pick two of those.

1:38:41You can't have all of them. Scene meaning like being a part of the industry and being very like parties, perks, you know, all that stuff. And so I got no scene, you know, and I like it that way. That's really good. I like it a lot. It's definitely my future. Right, don't invite me to stuff. It's like, yeah, stay out of the scene. Colin is, I can feel right now through this conversation, he's booking a ticket to the country. Yeah, I'm like, that's good. Yeah, yeah. I want to talk about fences. Yeah. I've, I've fantasized about that quite a bit, but I'm, I am, I try and do all three of those things and I, I'm not doing them well.

1:39:17Uh, and I, I think because I, the scene for me feels like such a big part of how these opportunities come. Sure. And again, I, I think I would say like my discipline right now that I need to get to is to allow myself to live in the world where this isn't all gonna fall away. Sure. I live in a world of fear that like, this is it. People are gonna find out and it's all gonna be over tomorrow. Sure. And we worked for 10 years to get here. Yeah. And so I live in this like constant anxiety state that it's all about to end. And I recognize, you know, I'm self-aware of that, but I have to work myself out of that.

1:39:58I think the problem is like, we tell ourselves that that fuels good work. And I'm not sure that it does. Do you know what I mean? Like, I think the best work comes from a place of fullness, not of emptiness, right? Not like I have something to prove, but like, this is important to me. I really care about this. I really did it right. And I totally, I think a lot of creators fear irrelevancy. Yes. Right. That like, if I'm not, like the reason I'm putting this out is because if I don't, then I'm irrelevant. Yeah. And I don't know if that makes Timelessly relevant work Right? Like it definitely means You're catching whatever wave is right there But you know Great work takes time Great work is not usually rooted In what this moment is Right?

1:40:49Like that's what Again like to go to Mark's real As we're talking about this book That was published 2 ,000 years ago It wasn't even intended to be a book that had not one iota of consideration of an audience whatsoever but it was so painstakingly done and so painstakingly rooted in the human experience and personal vulnerability that it actually did that thing that he didn't care about yeah but um i just i obviously hunger is important like that drive is good but i'm not sure that it makes and it makes good work i'm not sure if it makes the best work it's harder to do it from a deeper place uh things more disciplined but i think it ultimately is better yeah i completely agree with that i think um i think it's definitely like a common topic with, you know, young creators and even successful people.

1:41:49And I think on the other side of that is like, how did you decide what was enough for you? Was there a moment where you were like, this is, this is enough money. This is enough success. This is enough. Or is that, cause I feel like right now we live in this world of infinite opportunity. When do you get to the point where you're like, okay, well, this is enough. I was lucky. My first book came out and was a bestseller, like at 25, like the thing that I thought would take a really long time. It happened like right at the beginning. And you can sort of go two ways when you get everything. Oscar Wilde said the best thing and the worst thing that can happen to a person is you get everything you thought you wanted.

1:42:29So you get it. And what is your reaction to that? Do you tell yourself, I need more of it. Or do you tell yourself, oh, that was kind of anticlimactic. It, maybe it wasn't what I actually wanted, what's actually important. And so, I mean, that was, that was helpful to me to, to, to realize that this thing, this external thing was not ever really what it's about. And, and so then I've, what I've like, I've said before, like when my first book came out, let's say I was 10%, like, I can't believe I wrote a book. This is the book I wanted. I'm happy. This is a win. And 90%, like, let's see how this does.

1:43:08Right. And I, I think that with each subsequent book, I've gotten closer to flipping that. Of course, you still have to care if you're totally indifferent to what anyone says or thinks about it. Why would you do it at all? Right. Like you would still do it. Why would you put it out? Right. Like, why would you go the trouble of putting it out. But I've tried to get to a place where the success is the thing and then the other stuff is bonus. Wow. That is, yeah, that's, that's incredibly challenging. I think the hardest thing, the hardest thing, especially when you are like us as a, as a YouTube channel, we are the network.

1:43:42So we're both the production company, the talent, or all three, right? The production company, the talent, the executive producers and the network. So when we look at a video of ours and it underperforms as network executives were like, why did you make that? Sure. Right. And as creators, we're like, well, I liked it, but you're having this conversation in your head around like, don't ever make something like that again. Yeah. But you're also on the other side, you're like, but I loved making that. Yeah. And I think that was a good piece of content and you have to negotiate those two things as both the artist and the distributor.

1:44:14You also have to have a longer view, right? It's like, what timeline are you evaluating the success of this thing, right? The Obstacles Away came out in 2014 and it hit the best sellers for the first time in May of 2019. Wow. That doesn't mean it didn't sell before and I wasn't happy with it and pleased with it, but like what kind of timeline are you judging the success of something? Was that kind of a shock for you? Was that surprising at the time? It was surprising in the sense that I stopped caring about it. And so, you know, I was mowing my lawn when my agent called and then it was like, great.

1:44:48I still have to finish mowing the lawn. Yeah. Right. Like it's still, you realize it's like, Oh, it wasn't, I'm glad I'd stopped caring about it because it didn't do whatever I thought it would do, or I hoped it would do for me in May of 2014 when it came out. Yeah. Right. Um, and that is the really interesting thing about writing books is that you truly do have a library that at any time can be picked up by a certain person. Right. And we always call like, we try and spread that to YouTube creators as well, that you actually are building a library, a body of work, a body of work that, that, you know, we're continuing to take different shots on a, you know, pretty much once a week basis.

1:45:26But what we're finding now is that all of our work in the past is starting to like, the effect is starting to compound because new people are coming across us. And now we have a whole body of work for them to go spend time in. By the way, that's how the networks or the publisher or the studio or the label is able to give advances to new artists. It's because the catalog is where all the money is, right? Like every successful content business is actually a library of intellectual property and things that have recurring revenue streams. It's like the movie Elf makes money every Christmas, right?

1:46:03Things that connect to a timeless part of the experience. Like think about how many copies, what to expect when you're expecting cells, right? Because that is a thing that happens all the time. No one cares that it's 40, 50 years old. I don't even know how old it is, right? Classics stay classic. The library continues to do views. And the more you do, like even if only every video only does a thousand views a month, if you have a lot of videos, suddenly that becomes itself what you would be happy with if a new video did. And so you just have to, one of the reminders I try to tell myself is if someone hasn't heard of it, it's new to them.

1:46:43And so like, I'll do podcasts before. Are you okay talking about one of your old books? And then they're like, I have no preference to what order someone consumes or looks at the work. I just, I want them to consume the work that is interesting or valuable to them. I'm not writing old stuff off just because it's old and it's not old. I mean, like my bookstore, like every day will sell a copy of the Odyssey, the oldest book that there is. The Odyssey is new to a lot of people every year. Yeah. Or they're reading it again. Right. And it's new to them in their thirties or forties or fifties. I mean, again, our entrance point was growth hacker marketing.

1:47:26And then it was old, you know, when it was somewhat. 11, 10 years old, something like that. Yeah. So it was five years old when we read it. And it was new, brand new. And if someone finds out about it through this conversation, it's brand new. Yeah. And ideally, when you sit down to make stuff, you should try to think about, can it, does it have legs to be good five years from now? Or is it entirely rooted in what's happening? Yeah. in this moment. You know what I mean? That perspective helps us emotionally reckon with the volatility of the viewership because we are in the business of like really intently looking at our viewership the moment a video comes out, two hours after it comes out.

1:48:08I mean, 30 minutes after it comes out, YouTube gives you a ranking. Yeah. A one. Is it the worst of your last 10? Yeah, is it the best one out of your last 10 or the worst one? Within 30 minutes, you know. Interesting. So it tests you to like believe in the value, right? Like you have to believe in the value because they've deemed it the worst of your last 10 immediately. Yeah. But at the same time, it's like, do you want to make a video that's like how to hack the YouTube algorithm? Or do you want to make a video that says like how to tell a great story? What of those is still going to be viewable 20 years from now?

1:48:36Yeah. That's what I think you want to think about. I think that's where we like to lean to. Like we will never make a video that's how to go viral. Ever. Right. That's like an ever-changing landscape. We made a course two years ago. And the course is about storytelling. It's not about YouTube. And again, it's based on those principles of like, whether YouTube is gone next month or it's not, these principles have existed forever. Yes. You know, and that's where we want to lie with all of this is like, what are the foundations of this? Yeah. And look, like the bestseller list tracks how many books sold or how many books you sold that week, right?

1:49:13So if you sold 10 ,000 copies in one week, you'll hit the bestseller list. But if you sold 1 ,000 copies every week for a year, you would never hit the list, but you sold five times more copies. Which of those makes better business sense? And which one of those puts it like putting aside business, which one puts your message in front of more people that, which is why you did this in the first place. So, you know, do you want to be fast now or fast later? Like, do you want to, do you want to do this once? Or do you want to do this over the course of a career? Like those questions really matter.

1:49:45I think that's something that we're learning too, is like there's the success of your creativity in a project. And then there's looking at how do you have a 10, 20, 30, 40 year career as a creative. And that is something that I think allows you to slow down a little bit and evaluate the whole thing. Because we're also in a world when it comes to, specifically on social media, we haven't seen long, lengthy YouTube careers. We're starting to now. It hasn't existed. It hasn't existed. We don't know what it's like when you own your own network and distribution channel. Well, I guess, oh, and you're renting it from YouTube.

1:50:22But when you are doing this for an extremely long period of time, and I think to your previous point, like people are now shifting to exploring what is it like to own that audience so that, you know, it can exist in longer windows. I don't know if you're familiar with what's happening in comedy or like, I don't know if you saw Andrew Schultz. Yeah, yeah, yeah, he did his own special. Andrew Schultz. I mean, that was incredibly successful, shifting that to his own hands and like essentially ripping the networks, you know, and ripping it out of the network's hands and saying, actually, wait a second, to have this exist for a very long period of time, I will be the distributor and I will own it and I will.

1:51:00And what's so interesting about that is it's actually more of a tiered approach. Right. It's like it will go first to the people that want it directly. Sure. And then maybe it'll go to a network streaming platform. I saw Iron Maiden play in Austin on Wednesday night, and they sold out the Moody Center, which like the next big act is Harry Styles. So this is a band that's 45, 50, almost 50 years old. Yeah. Never been popular, like never been like a radio band, never had any like huge mainstream hits, selling out an arena, 20, 25 ,000 people. It's multi-generational. They've sold a hundred million albums.

1:51:42The joke was that they'd sold more t-shirts than albums, but the margins are probably most well-known now for their vintage t-shirts. The margins on t-shirts are better than the margins on albums, first off. But like, there's this quote from Bruce Dickinson who's the lead singer in the band who has always been sort of a creative hero of mine. And he said, like, you can only plow one field at a time. So he's like, we have our field and that's what we care about. And we don't care what other people are doing. And I once heard this story about their manager. I think his name is Rod Smallwood. And someone said, like, oh, like, I really like I you're one of my like heroes in the music business.

1:52:20And he said, like, I'm not in the music business. He said, I'm in the iron fucking maiden business. And he realized, like, oh, yeah, you're not in this general industry. You're in your thing for your people. And that's really all that matters. Are you speaking to them? Are you making something for them? You don't care what trend, like, you know, Iron Maiden or a wave of heavy metal, but then grunge and then indie rock and then EDM and then rap. Like none of that has been important to them because they're not in the general music business. They're in this specific band for this specific people.

1:52:53And so like Daily Stoic is like, I write an email every day to these people. If you get it, it's for you. If you don't, go do whatever you want. But like, this is my field. And if you think about it that way, I think it really narrows your vision and allows you to just do and invest in the things that can hopefully make it so 40 years later, you're still doing it. It does require a lot of discipline around comparison. Yes. Which I think is a human, you know, a natural human instinct that is challenging to fight against, right? Because comparison is like, I mean, as I don't know who said it, but the thief of joy, right?

1:53:29Theodore Roosevelt. Theodore Roosevelt. Great. And now I know who said that. Yeah. Yeah. But that is, I think the thing that you have to really work on is like entrepreneurship and creativity, I think is a journey of self-discovery. And I love that about Iron Maiden to be like, I'm in the business of Iron fucking Maiden. That's cool. That's a great quote. That's such a great quote. Because it's like, if you live in a world where you're working on your thing and your thing is great because it's your thing and your achievements are great because you wanted them. Yes. That's a, that's a different world than existing in the, in the scene of like, yes, you know, and it's still, you still learn from other people.

1:54:04You still see, like you're still taking stuff back, but you're not like one of the most helpful things I learned as a author. Someone told me like, you're not competing with other authors. Like you're competing with people not reading like so you're not like i don't care that someone else is successful like good for them that's probably helping encourage people to read generally like we're not fighting for market share right yeah um at all like we're we're fighting against people not caring and realizing that somebody else it's not a zero-sum game somebody else's success is not at the expense of yours and in fact, you know, let's say they were really successful.

1:54:47They got some huge deal. Maybe that means that all the prices of all deals are going up or you didn't even know you could get a deal for that. And now you can call someone on your team and be like, Hey, can you check this out? Or like when I see, I try to remind myself, like if I see someone on get on someone's show or whatever, I'm not like, how did they get that? I go, Oh, that's a good idea. I'll write that down. And the next time I'm marketing something, I'll ask someone to pitch that. Like, so instead of feeling jealous just learn yeah what's a show you'd want to be on that's a good question i don't know if i have any right now um rogan was obviously one i'd wanted to do for a long time and like that just like i i was going to sleep and my wife was like uh joe rogan just posted copy your book and he sent you a message on instagram and i was like uh-huh sure and then like i woke up the next morning and i was like what was that you were saying and it was like That's what happened.

1:55:37And he had read Obstacle, which was nine years old at that point or something. So if I had been insecure and jealous that other people I knew had new books coming on, all I really had to do was just sit and wait my turn. This episode is brought to you by LifeLock. When you visit the doctor, you probably hand over your insurance, your ID, and contact details. It's just one of the many places that has your personal info. And if any of them accidentally expose it, you could be at risk for identity theft. LifeLock monitors millions of data points a second. If you become a victim, they'll fix it. Guaranteed.

1:56:15Or your money back. Save up to 40 % your first year at lifelock.com slash podcast. Terms apply. big impact on for sure I mean it's the biggest show in the world. Yeah. Yeah. Uh, you wore an Iron Maiden shirt on the show, which I loved. Are you nervous going into that type of interview or? Yeah, of course. Yeah. And it's also just, it's long. Yeah. So you're like, where, like, it's hard to just envision a three hour conversation. Like, where is that? You have no idea where that's going to be. You're living in it right now, Ryan. Yes. How long have you done? Almost. Two hours. All right. Yeah. I was thinking though, Samir and I both, uh, re-listened to that episode.

1:56:54And it's interesting that he's not super agreeable, which makes for an interesting episode. Like not that he was against the things you were saying, but if he found any little moment that he didn't agree with, he would make sure to bring it up. And then you had the opportunity to come back and forth. And I think like that tension for me as a student of interviews now, I realized that that's such a valuable part of it, that you guys got along, you got to some really interesting information, information but it wasn't just through two and a half hours of agreeing well so so when i do a show like that like uh i'll ask people who have been on it or people that know the person be like what you know what should i know not know whatever and obviously i listen to the show when it's like yes that i'm interested in but uh they were like he does do that and they were like don't get in pointless disagreements about things that you don't care about so they're like they're like It's not that he doesn't want you to disagree with him, but my advice is only push back on things that you really want to get in a huge argument about, that you actually really care about.

1:57:59Otherwise, you'll derail the whole thing by getting into some conflict about something that neither of you - About jujitsu, yeah. Yeah, and so I was like, oh, that's really good advice. And I think the interview did go well, but I was thinking about that in that time. because like you just never, you want to know like the, again, with every medium, you're not just like, oh, they said I should be on TikTok. So I just started posting these videos, but like what actually works there? What is the medium need or want and what works? I did love how much you guys dug into like the actual stories of like Marcus Aurelius and Roman emperors and like we're able to touch on like those stories more in that, Not only how they applied to the world today, but actually just got to dig in.

1:58:45I do love what I love about podcasts is like the long form. Like when you do a TV show and they're like, this will be a seven minute spot or four minutes. But like that's by definition, like very superficial and to just have like three hours or two hours or like this to talk about. I think that's the best. Yeah. So when it comes to like audience building, you have a new piece of work, right? But how do you think about building audiences for your content, I guess, or your books? Like as a creator, you know, we kind of rely on the algorithm and play games with the algorithm to make sure that it gets fed to the right people.

1:59:24But that's not necessarily, you know, maybe Amazon, you can know a thing or two about how that works. But when you have a tangible - Yeah, Amazon algorithm work. There's an algorithm there to that, for sure. It's like, what are the distribution, I guess, strategies you have when it comes to, you know, you put all this time into this book. How does this get out to people? At the end of the day, all books, all things that are a success are because people who consumed it told other people about it. So everything that you do from the creative process to the marketing process has to be about facilitating that happening.

2:00:00So most of the work happens before it even comes out, right? the choice of the topic, the way it's done, the length of it, the style, the cover, all the stuff has to be made towards being conducive to a process where someone says, you have to read this. You have to watch this. This is amazing. Like, let me refer you to this thing. So that's like 80 % of it. And then the next part is like, how do you get as many people into that as soon as possible to front load that process. If word of mouth is the driver, then yeah, if one person reads it, that'll become two, which will become four. But how long is that gonna take, right?

2:00:42So the process is getting to some numbers at 10 ,000, at 20 ,000, is 100 ,000 of those people who've read it, consumed it, loved it, changed it. And then they're the evangelists for your thing. So the whole process is about that for me. It's so interesting because we think about that too in terms of like the share button, right? Like if people aren't clicking the share button, then we haven't made something. But if they're not watching it, they can't click the share button. They can't even do it. Yeah. So you actually have to have enough people in the funnel to even potentially create word of mouth.

2:01:14Yes. But I love that the tangibility of even a digital creator thinking about word of mouth. Yeah. You know, being able to think about like is someone having coffee with someone and saying, did you watch that video? If they aren't saying that, then you're - texting it or, and then you can even think of like search as a kind of word of mouth, right? You're like, I need a solution to this problem. And then instead of your best friend's dad telling you the solution to the problem, Google is telling you the solution to the problem. Or YouTube. Or YouTube creator. You're searching that thing. And because enough people have consumed it and sort of voted for it, that's what gets served up.

2:01:55Yeah. So is this available now? September 27th. Oh yeah. So it is available now. It's available now. It's available now. Amazing. Well, Ryan, thanks so much for this. By the way, I'm very excited to have this, a physical copy of this. I think we need to visit the bookstore. I think I'm going to be in Austin at least twice before the end of the year. All right. Absolutely come to the bookstore. I would love that. And yeah, when we write our book, I will hand you a copy. I can't wait. Could be in five years. could be in the decade. We will take our time. Probably too much time, but yeah, we will physically hand you a copy when we have it.

2:02:33But thank you so much for this and thanks for coming on the show. Thanks for coming. Of course.