How Ryan Holiday Built a Million Dollar Content Empire | 107

I've done thousands of episodes of the podcast. I've done hundreds of videos. You have to accept the first draft of everything is shit, and then you get comfortable with it. That's the only way you're gonna make things that don't suck.

10 years ago, stoicism was an obscure philosophy that was only talked about in academia. Now it's everywhere, and Ryan Holiday is the reason why. We recorded this conversation in front of a live audience in Austin, Texas, which was so much fun. I mean, at launch, if you— That is a wild success for—

That will put you on the bestseller list for sure. The biggest book in the world is going to reach a fraction of the amount of people that a video or a tweet or an article or a podcast gets. The way I think about content is like, how do you make one thing that can get caught up in lots of different things? If I'm going to take time away from writing, it has to generate multiple uses. It can't just be a singular thing.

From Daily Stoic and Daily Dad to his New York Times bestselling books, he's built a content machine that reaches millions, all without having to spend money on ads.

You make an ad, it gets seen by 100 people, 99 of them don't like it. If you make a piece of content that 99 people read and get something out of and move on, but one person reads and gets something out of it, you've still got the same conversion, but you've also just given something of value to 99 people. That's the benefit of content versus ads.

If you've ever wondered how to build a career that makes an impact and stands the test of time, this episode is a masterclass.

You got to find something that's both timely and timeless. Timely is your way into it, but the timelessness is I like that.

Please welcome Nathan and Ryan Holiday to the stage.

Hello everyone. They don't know how to respond. Yeah.

All right, Ryan, you don't talk a lot about the content side of the business, like the behind the scenes.

Yeah, there's a lot of creators here.

That's what I want to dive into. Okay. And specifically, A few, a number of years ago, you went from spending hundreds of thousands of dollars a year on advertising to cutting all of that and building a content team in-house. I wanna know two things. One, why? And two, how'd it turn out?

Yeah, so, uh, we launched Daily Stoic in 2016. Uh, the book was coming out and we thought, you know, uh, Daily Stoic is a page a day and I just, I had fun writing it and I thought, let's just keep this going, right? I was thinking like, what do you do after you get to the last page of the book? Some people start again or some people just keep going. So we bought dailystoic.com and we launched it as an email list. And then we had our first product and another product. And then as it was growing, you know, you go, okay, it's doing well. How do you grow a business that's doing well? Usually the first impulse is advertising. And we, fool around with these different platforms and it was successful in terms of acquisition of customers and driving traffic and it was great. And then I just, I remember thinking like, if we stopped doing these ads, they would stop driving traffic. People would stop caring. It would be like they had never happened. And so that seemed like a weird thing given the amount of money we were spending, but also the amount of time. Like we're, microtesting copy and pictures and you're fine. You're, you're, you're treating it as content, but the customer definitely doesn't think it's content. They don't want to see it. If it went away, they would be happy. And, and so that just seemed like a weird use of resources. And I thought, but on the other hand, we've written these articles, we've made videos, we've done stuff that, uh, we don't touch anymore, but drive people every single day. So we just, we pivoted from spending anything on advertising or public relations and just putting it all into content. One being that it was more effective, and two, that it had a positive impact in the sense that people were looking for it, and when they looked for it, they liked it and it did something for them. And so I just thought that's like, again, you make an ad, it gets seen by 100 people, 99% of, 99 of them don't like it, don't care about it, right? Um, but if you make a piece of content that 99 people read and get something out of and move on, but one person reads and then gets something out of it, you've still got the same conversion, but you've also just given something of value to 99 people. And so that was kind of the, the pivot that we made and, and, um, you know, I'm proud of all that stuff and it's still there and, and we could stop tomorrow and coast under our own power for a considerable amount of time because that's the benefit of content versus ads.

Yeah. So when, when was it that you made that decision?

I don't know exactly. I, I wrote about it a couple of times.

You wrote about it in 2023.

Yeah, it was definitely before that. Uh, maybe a couple years before that. Um, So it's been a while. I mean, we just, we just spend all our time and energy making stuff. I remember I was hanging out with Casey Neistat once and he said, um, he was like, people like you and me. And I was like, okay. All right.

Yeah.

He's like, he's like, people like you and me, we don't make, uh, we don't make stuff to make money. We make stuff to make money, to make more stuff, you know? And, and that the, the point of the success, this is, I think the other part of it is the, the point of the success should be to make stuff that you like, that you care about. That's cool. And, and like, I think for a while I also thought, you know, how do you, you know, sort of the Tim Ferriss stuff, like how do you keep it as lean as possible, have as little overhead as possible? And then I was like, you know, I enjoy making this. I enjoy collaborating with people. I enjoy having a team. I enjoy teaching people how to do stuff and then they go off and do their own thing. And so yeah, that the, the infrastructure, the business that came out of it, all of that stems from the decision to just make more stuff.

So the YouTube channel now for Daily Stoic is like just a hair away from 2 million.

Yes. Yeah.

2 million subscribers. Like, you know, if everyone in this room plus all of your friends subscribed, we'd be there. I don't think we're that close to 2 million, but it's 1.98 something.

It's very, it's, it's tantalizingly close to 2 million. And I, and my kids are back there. The only thing that I've ever done that they're impressed by is the YouTube plaque that I have on my wall for a million subscribers, because that's the only thing that intersects with their world of things that they like. So, uh, you know, if I could get the 10, that, that would really, that would really matter.

Yeah, I love that we're going there for our validation. Um, so it's obviously paid off and worked in a big way.

Sure.

If you were to look back with the benefit of hindsight, like, what are the, the 2 or 3 things that you think really made a difference in in building the team or how you approached it?

What's interesting too, right? No one in my life had ever come up to me and said, hey, I heard about you from an ad on Facebook. Right. You know, uh, I became a fan because I saw a Reddit ad or whatever it is. That's not how it works. But I hear all the time, like, people found me from the algorithm. This is a, another conversation I was having with Rich Roll, whose stuff is great. And he was like, these algorithms, like, for better or for worse, are the most powerful forces culturally in the, in the world. And. How are you making things that, that algorithm can, can surface your work to other people? That's what you want to be thinking about again. And, and by the way, it's free. Like it do, you make the stuff that's not free, but the, the tapping into the, the stream is, is, is free. And, and so I, uh, what I think about is like, I read a lot of books. Books are my world. I talk to people about books, but that's not most people. Most people are not reading book reviews. Most people are not. Reading books when they come out. Most people read books every so often, uh, at best. So I, I think a lot about how do I make stuff on these different mediums that brings the ideas from the books to people that otherwise wouldn't be in that circle. And then ultimately everything is about bringing them back to that. Does that make sense? Yep, that does. So, um, I think that's what the content does is it allows you to reach people where they are and then show them what you want to show them.

Yeah, I've seen you like start to make content that it feels like you really want to make. And so one of the things, like talk about the marathon video. That's a fairly recent one that you just did, right?

Yeah, I mean, that's my other thing is I don't make anything that I don't want to make. Right.

Um, and I mean, there's certain, which is not true for a lot of YouTubers. Like you would say, that seems like an obvious thing. Like, oh, I don't make stuff that I don't want to make. And like, well, duh. But if you look at the industry that we're in, I would say at least 50% of the time, that's not true. Yeah. There's more money.

I certainly know things that I could do that would reach more people or would, uh, get more attention. And, and I don't, I don't do that. I make stuff that I, I want to make because I feel like I'm, signing my name to them. And I also think, like, one of the quirks about what I do is that, like, I didn't invent any of it. It's a philosophy that's 2,000 years old that has a tradition of what it stands for and what it means, and that I feel indebted to because it's changed my life in many, many ways. And one of the things I have written on my wall next to my desk, it says, like, are you being a good steward of Stoicism? So I didn't invent this. I don't own it. I just happen to be the person that by luck and circumstance, and then also some decisions that I made, I'm one of the people that get associated with it. And so I feel like there's a responsibility.

One of the current stewards of stoicism.

Yes.

And so in 1,000 years, it'll be someone else.

Yeah. And it's not that I think so much like, what are people going to think in 1,000 years? I just go, hey, there's typically one person who is the face of this thing at any given time. And what obligations and responsibilities does that confer? It, it, it, it, I think it confers not, you know, chasing silly trends or I don't do like TikTok dances. I also don't, I also try not to, you know, like troll or I, I, I just try to take it seriously, I guess is what I'm saying. So I, I typically only make stuff that I, I want to make, but I, I try to, I try to think about what I'm excited about or interested in and how do I connect it to different niches. So yeah, the, I ran the original marathon from Marathon to Athens, uh, this summer. Uh, that was really cool. Um, well, it was, it was cool act to have done it. It wasn't so cool doing it. I think you have the line that you just threw up in. Yeah, I did. So you finish in the Olympic Stadium, which is thousands of years old. That is this beautiful shining marble stadium. And, um, but you get there and then I had to wait in line to buy a ticket to finish, to like run the last one. 100 yards. That was weird. And then I promptly threw up all over the stadium. And, and it's like, not a thing. No one else is doing the marathon. So, uh, it wasn't like it made any sense. It was like, it just seemed like a drunk American who was throwing up in front of everyone. And then, and then I just sort of like, you know, what do I do? So I just walked away. Uh, I wasn't— then I watched a video afterwards and I was like, obviously reeling from sunstroke and dehydration. And I was not in my right mind at all. Cause like they sat me down and had me too, like it's sort of an interview after and like none of my answers make any sense. And, and I was, I was, I was pretty close to the, to the edge, but, um, it was something I'd always wanted to do. And, um, so I, I thought it would be cool content and then Um, we worked with a, you know, a, a great company that's actually based here in Austin called Backyard Ventures who sells all the sponsorships and stuff. And so they, Hoka sponsored it, which was really cool. Yeah. It's, it's like one of my, the, the, not, not just, it was like a cool experience. And then I think the video turned out well, but it was just like a process of learning how to tell a story in that medium, which is not mine. I don't. I don't think in terms of like a, you know, a 30-minute narrative documentary. That's not the medium that most of the time I think about. And so, yeah, it was really cool.

Well, see, now you and Casey Neistat are more similar.

Yeah. Well, he did give me some advice, but yeah, it was a really cool thing to do. And then we're doing, like, the way I think about content is like, how do you make one thing that can get cut up in lots of different things? So you make a 30-minute video and it's all also, you know, a certain number of reels. And it's then also once you have the thing, how do you turn that back into an article, which is what I think about. And then of course it's social media posts and pictures and carousels. And then like, I just saw the draft of the video that's like lessons learned while doing the thing. So I spend, if I'm gonna spend time, if I'm gonna take time away from writing, which is what I love to do and what my main thing is, it has to generate multiple uses. It can't just be a singular thing. So every, everything is, how do it fit? How do it fits into different parts of the content machine?

I think a lot of people, a lot of creators aspire to, to have that content flywheel and, and to have it parted out in all of those ways, but struggle to actually pull that off.

Yeah.

What, what makes the difference, whether it's the pre-planning or the team behind it, to actually be able to make that happen?

Well, I think the whole point of a flywheel is that it's a struggle to pull it off. Like, no one says, I want a flywheel, here's a flywheel.

Yeah, it's not the easy path.

No, it, but it takes a long time. So, you know, it started with an email list and then the email list became, uh, we, we would, we send out the Daily Stoke email, which is, you know, a, you know, 200-300 word little thing every day. And then people would email and say like, I don't want to read it. Every day I'd like to listen. And so we did a podcast version and then now, oh, the podcast is doing a certain number of downloads. And so, okay, well, what's long form we can plug into there? So every episode is not 2 minutes long. So then the podcast built out and now it's the podcast is every day and actually now it's over the weekend too. And then we expanded into YouTube and social media happened at some point. So each one of the things was independently built. But took some of its audience at the beginning from another part of the system. And so I think sometimes people sit down and they go, okay, I want to flywheel. So I need to do audio, I need to do video, I need to do email. And like the main thing they're missing is anyone giving a shit, right? Like you're making all the stuff and it's this idea like if you build it, they will come. And that's not really how it works. It's, it's, you have to start with an audience of some kind, or you have to slowly accumulate an audience. And from that, you can go from strength to strength, but you really can't just like, it's not that you map out that it would be great to be a multi-platform entity with, you know, you have to, you have to build the audience each time in a new way. Um, and you usually go. At least what we've tried to go is, is to go with the demand as opposed to supply. Like most people are just supplying and supplying. There's not actually like a demand that they're responding to.

So yeah, you're really taking the approach of one platform at a time and expanding to there. Now, now that you're at the stage that you are, so let's take like the marathon video instead of just making that video and it being 20 to 30 minutes long and, and all of that. You're talking about all the other places that it shows up.

Sure.

And you're, it sounds like you're intentional from the beginning of creating the video of knowing some aspect of where that's going to go.

How are you telling, like, okay, so when you write a book, right, you write a book and then typically it goes to the publisher if you're working with a traditional publisher, and then they have a subrights team who sells it to France and China and, and all these different things, right? And those people translate it into those mediums. And a lot of times, it's a, it's a new cover. Sometimes it's a new title. It's sometimes they have a foreword from a person there. It's their, they, and the reason they're doing it, the reason Penguin Random House, even though it's this global company in my case, doesn't just give it to a subsidiary, their subsidiary in each market is like, there's something to be said about expertise and a fluency in that language and that culture and that market and distribution. So like I try to, I've tried, I've built out a team each One of the people is good at those things. So I have the thing that I want to do or the thing that I want to say, and most of it is driven for Daily Stoked by the, the email, which is like the main engine of content, because that has to be done every single day. And then how do, how is each person helping me translate that thing into another? So like, maybe yesterday we were shooting, sitting down to shoot, um, some Daily Stoked videos. And like instead of me having to write a new script from scratch, or conversely, like someone on my team having to write a 20 or 30 minute video about stoicism, they're taking some stuff that I riffed on in Reels. And you know, you take the video, you put it in ChatGPT and it kicks you out a transcript and then you're editing and adjusting words that I said, like the AI's not making anything. It's just helping you speed up. You already made something here and then they're taking, oh, you know, you address this in this article and you address this in these 3 Daily Stoic emails and now those things combined become a video and then that's going into a teleprompter or I have a script and then I'm riffing on that script and, and in taking the stuff I've already done and re-recording it in a new setting and it's, it's being made into a new thing and then that goes to the editor and that goes into their schedule. And then maybe conversely, that 20-minute video is going to the social person who's cutting it up into 5 2-minute clips. And the same might be said, it's like I sat down, I interviewed someone on the podcast today, right? That podcast goes to the social media person who's cutting it into clips. So you're making something in one medium and then you're seeing how it translates to the others.

Yeah, all of that makes sense. So then how do you think about content formats or maybe something that you could repeat over and over again. So like a video that you often do with the bookstore is you taking, uh, either someone, I guess on the podcast, or you're showing through the bookstore or something else and you're giving them your favorite books, right? And so you found a format there that you can do many, many times and yet it's still unique.

That's true. Yeah. So the, the last question on the podcast, and so I, I do think of like, what are things that you can do over and over again? And then those things can be easily set into compilations because the setup is the same. But so the last question on the podcast is usually, so do you want to go check out some books? And then we walk next door because the studio is next to the bookstore and we just kind of shoot the shit talking about books. I partly got, we were already doing this, but Simon Schuster, the publisher, has a great video, a great program. I just did it when I was in New York. They go to McNally Jackson in Rockefeller Center. And you have like 3 minutes to pick out.

I saw that video.

It's really fun. Um, and I'm just doing it in mine. I go way longer than 3 minutes. Uh, but we just shoot the shit and talk about books. And then those, uh, those can be cut up in infinite number of ways. And they can also be, you know, an independent, uh, you know, 5 or 10 minute video. Um, but yeah, I'm just thinking about how are you shooting stuff, cutting it up into pieces, and then assembling it and reassembling it in all these different ways. And you never, you never know. It was actually funny. So, uh, Matthew McConaughey, when, um, Greenlights is coming out in paperback, did an event at the bookstore. And so we're sitting near like this and I, I, it was obviously very cool and I was very excited to have him. Uh, but I, I kept thinking like, why are you doing this? You know, like, like you, you could have sold out the Paramount Theater down the street. You could have gone on Good Morning America. You could have done anything. Why are you talking? And our bookstore is pretty small. Like the fire code only allows like 70 people or something. So it's like one of the biggest movie stars in the world talking to 70 people on, you know, a porch of a bookstore. And then it was funny. Someone got up and asked, um, they said, hey, I heard you on a podcast. I heard you have like a great, um, tuna salad recipe. And, and he was like, I do. And, and, and he, he proceeded to give a very specific step-by-step recipe for this tuna thing, which is actually delicious. We went home and made it. But, um, it, that video alone did, I think, like 9 million views on TikTok. And then you realize, oh, like it's, it's stuff like this, right? It's, it, there's actually a great book we carry in the bookstore by, by Daniel Borsten called, uh, The Image. And he talks about pseudo events. Do you know what a pseudo-event is? So a pseudo-event— this is— he's writing this in the '50s, so he's way ahead of the curve. But a pseudo-event is like, what is the purpose of a press conference? A press conference is literally to gather the media for the express purposes of telling them something that you could have just called them on the phone, but you're making it photogenic or telegenic or radio-broadcastable, right? A movie premiere is a pseudo-event. It does not need to happen. The people have all seen the movie. Why are you inviting all the celebrities to wear fancy clothes and walk a red carpet to watch their own movie? Like the public is not even able to see. The, the purpose of this is so there will be cameras outside filming and talking about it and maybe something will happen. So this is what a pseudo event is, right? But the, the point is, um, you do things in the world that create opport— that are opportunities for content to happen. Effectively. And so like him doing it, the purpose of the event, not that it was this Machiavellian thing, but he's talking to 70 people, but he's actually talking potentially to an infinite number of people because each one of the things that happens can get cut up into any number of pieces and go anywhere. Does that make sense?

Yeah. So it's ultimately just a set.

Everything is a set. Yes. Everything is a set. And like, The bookstore is a, like, I think it was funny when we opened this bookstore in this little town, uh, if you guys have been to Bastrop, um, people were like, what are you doing? Even, even people in, in Bastrop were like, are you guys sure? Like, they were like, everything in this spot has gone out of business. Like, we don't, they were really nice, but they were like, I don't think this is a good idea. Yeah. They were like, please don't.

And it felt like right at the start of the pandemic as well.

Uh, well, it was, yes, yes. That we started construction the first week of March. March 2020. Yeah. So it was perfect time.

Great idea. Ryan Holiday enters retail.

But as soon as they could come in, they were like, are you sure this is a good idea? And they were, it was coming from a good place. But like what I understood is that first off, the purpose of the place was a, was as an office and a bunch of other things, but is also a giant set.

Right.

And so as long as it doesn't lose tons of money every day as a bookstore, which it doesn't because it's a small town in Texas and bookstores are not super capital-intensive businesses. It is an engine for content. Um, uh, Brent, who owns Cerro Gordo, we both know, it's like he, a friend bought this ghost town in, in, in Southern California. And again, it seems like a crazy, reckless, uh, idea. And, and people are like, are you going to mine for gold? Or silver, and it's like, no, he's mining for content. It's, he goes into the mines and finds nothing, but content comes out of the other side of the exploration. And that's the ideas. And I think the more interesting things you're doing and interesting places you're going, the more interesting the content. It's not so much like you're sitting in your office and talking straight to camera, but like, what are you doing? And how is this, you know, something compelling to watch? That's That's what it all is.

Well, Cerro Gordo is such an interesting example. It's the name of the ghost town. Um, and you and I are the, uh, I guess the, the second and third, the, the first and second suckers. We, Brian and I both own 10% of the ghost town. Um, and so we just, so it was just Blair, uh, two weeks ago. Did you run the hill?

Did I see you? I didn't do the whole, the whole, but speaking of content, like, uh, when Discipline came out, I was like, what could I do that's like a chance to talk? I could sit in my office and go, discipline is really important. You should do hard things. And that would be somewhat compelling. Or I was like, I'll just do a hard thing and I'll talk about it while I'm doing it. And I ran the town. You enter the town at, you enter the road to the town at 4,000 feet of elevation and you enter the town itself at 8,500 feet of elevation. And it's a, well, he told me it was a 7-mile road. It's more like an 8-mile road, uh, but basically straight up and you do almost, so you do almost a mile of elevation. Uh, and so like, I just did a video about it and that video did well too. So the idea is like something cool talking about something interesting that comes together. You can find infinite ways to make that. Work in all the different mediums.

Yeah. And the, the idea of something being a set. Yeah. I think it's so important. So with Cerro Gordo, it's, people are always asking me like, how is this going to make money? Yeah. You're gonna get the hotel operational and then it's gonna be 6 rooms and you, they're like running through the math. They're like, that, that doesn't work.

You know, they keep going down these angles and they're like, it doesn't make, but as every building he builds, like he, he built, he's built this shack and which I, was there. I shot some videos in front of this, this cool cabin that he built and the mountain. And it's like, you know, the, the, the cabin was a video, right? And, and so it's not just the library in the dynamite book. It's not just everything is a set, but like, we're thinking about this now. So like, uh, the building next to the bookstore, uh, which is the podcast studio. So it is, it faces the, the street, it's retail, but like, obviously you can't have the podcast. The part of the reason we had to buy the, the building next door is that we would close the bookstore for 20 minutes to film something and people get mad. Or we'd be filming and have closed the bookstore and people would be like knocking on the glass and looking like it was causing disruption, not just to the bookstore, but it was impossible to use it as a set also. So we expanded into this building next door that is the studio and my wife's office in the back. But the front has like 50 feet of retail, square feet of retail storefront. And I've been trying to think about what I want to do with it. And I was going to do something like the Prada store in Marfa, you know, where it's just like a fake store. Or I was going to do something, I don't know, like political, or I was going to do something funny. I think we finally cracked what it is. And we were talking about this at a meeting on Tuesday. I don't want to say what it is because I want it to be cool. But we were like, okay, so this is what we're going to do. So now who's like a cool YouTuber or influencer who does this kind of thing and will collaborate, like I'll pay for it, but like we'll collaborate on the making of the thing. So it's not just the finished product will be cooler to walk in and out of when we do the bookstore parts, or like, it'll look cooler on the street, but the, the doing the thing itself is content that should be interesting and cool. Like, um, a couple of years ago, uh, I wanted to do something, a friend of mine, um, named Jeff Waldman, who designs like these cabins, uh, he's, he's a really great designer and he designs cabins and he sells the plans for the cabins. And, um, he was like, hey, I want to do a cool project. And so I was like, I think it would be cool if there was like a tree inside the bookstore. And so we found a big tree that had fallen over on my, uh, at my ranch during a storm. It's like a 25-foot-tall tree. And, uh, you know, we cut it into a couple pieces and we moved it and then we reassembled it. It runs. Up the middle of the bookstore through the balcony, and then it looks like it goes out the ceiling. And so like, that was a cool thing. And now people walk in and it looks cool and it has books hanging from it. And it improved the overall like decor of the store. But it also was just, we could have immediately removed it and it would have had the same effect because it was the video we made about the experience that was also cool and it has sponsor and blah, blah, blah.

Yeah, I mean, there's so much that you can do with that. I'm realizing when we've launched Kit Studios, so we have them in Boise and in Chicago. So I record a lot in Boise. And so there's, you know, there's 5 studios in the Boise location, but I don't think of the whole thing quite enough as a set. And so that's the thing. That was one of my takeaways. Like I bring in, you know, 4 or 5 creators at a time and we, over a 2-day period, will record a month's worth of podcast episodes. Because I do weekly and not daily.

Yeah.

Um, it's way easier.

Definitely. If you cannot do daily, I would recommend it. Yeah. Um, cause we're not, it's like, I realized we're doing daily in like 8 different mediums. Oh yeah. So you're actually doing 8 daily shows.

It's like the calendar is extreme. Your team puts up with a lot.

Yes.

Um, but in that I don't have any content that I'm creating around the event yet. So watching you do the bookstore and, And tie in the different areas and have like kind of these 2 to 3 parts of the set made me realize that there's way more that I should be doing around the recording of the podcast that's just as interesting as the podcast itself.

Okay. So, uh, another sort of weird obscure term from the, uh, mid-1900s. Uh, my favorite novel is this book called The Moviegoer by Walker Percy. We sell in the bookstore. I've loved it forever. There's this guy, he's obsessed with movies and, and at the beginning of the movie, he's like, at the beginning of the book, he's giving his theories and he says, he's at this movie, and in the movie, they pan by the movie theater that he's in, and he loses his mind. And he's like, his word for this is certification. And his point is anything that you've experienced in real life that you then see on film suddenly seems so cool, even though it's not significant at all. We just find that really exciting or cool. And so his point is that, like, What I've taken from this is that, and I've seen this happen over and over again, like, so people will come in the bookstore and be like, that's the tree from the video, you know? And because they saw a thing about it, right? And, and I think about this myself, like you, you're in New York City and you're like, oh, that's the diner that Seinfeld is from. Right. And like when there's like a nostalgia or an affinity for stuff that you've seen before. And what social media does is it allows us to follow things as they're happening or being made or an insight into people's lives. And so when you kind of, when you make the thing, when you bring people into the making of and the developing of and you show them how it works, it becomes just more of an experience. And like the premise of the bookstore is like, look, if you want a book cheaply, you should buy it on Amazon. If you want a book right now, you should get it on Audible or Kindle. There are easier, faster ways to do this. So if you're deciding to go to a book— an independent bookstore, you're looking for an experience. Like, um, we used to have a record shop as part of it. We still sell some vinyl records, but we rented it out to this, uh, lovely guy who was like just obsessed with vinyl. And he used to say all the time, he's like, I don't sell vinyl records. He says, I sell the experience of buying vinyl records. Like, yeah, I sell the experience of going through the bins. And then you buy a record that it would— you're probably not even going to listen to. Honestly, you're going to put it on your mantle. And then when you want— when you think of a song, you're going to turn on Spotify. That's what you're going to do. You're going to buy like the Taylor Swift vinyl when it comes out and it's going to stay in the packaging. But that's not— but you wanted to support the thing or be a part of the thing. And so the point is, like, even as we design the bookstore, the reason there's a tree in it and the reason there's a 20-foot 20-foot tower made out of books that, you know, built out of the fireplace. And the reason there's all the stuff in it is to make it a cool place to go and experience and to photograph and to talk about. That's what it is. And so it's not just that it's content, it's that once it's content, it has a greater resonance in real life.

There's this guy who— his name's Al Doan. He's a Amazing content creator. I say that he doesn't actually create content. Uh, his mom creates a lot of content.

Okay.

Um, he says that every creator should own a town. And so Brent took that literally and went and bought Cerro Gordo, but he owns Hamilton, Missouri, which is, um, the Disneyland of quilting.

Okay.

And so they, his, him and his family own the Missouri Star Quilt Company and they have taken over this entire small town. They have restaurants, they have, uh, everything you'd want for quilting, fabric shops, all of this stuff. And it is like, uh, hundreds of thousands of people visit from around the world to see what they saw on YouTube videos, then show up in person for this. And it is so popular, they have purchased the neighboring town and they continue to expand this. But his point is that if you're creating content, you need a set.

Yeah.

And then even better is if it's a set that other people can visit.

Sure.

And so you see this with Cerro Gordo where people freak out.

I mean, it's very hard to get to and you're there and just one person after another, they're like, hi. And then that's it. And they did, that was the whole thing. They wanted to go up and see the place. Right. It had been certified to them.

So one more thing on content and then I want to go to like much more of the content creation process and writing and all of that. Um, I'm curious as you've watched, so you and Brent have been business partners for a very long time.

He started as my intern.

Yeah. And look how far he's come.

Yes.

Work for Ryan. That's the takeaway. Good things can happen. Um, what things, like, Brent was always a behind the scenes person. And then with Ghost Town Living, as the channel has passed, I think it's like 1.7, 1.8 million subscribers at this point.

Which is, belies how huge the actual videos are. Like, way more views than subscribers for some reason. Uh, it's, it's annoying, but like he will routinely hit the homepage of— Yeah, yeah, it's amazing.

What are the things that you've learned from watching his experience, like growing the Cerro Gordo channel and the town and all of that?

Well, so it's funny, we were filming some content at my house that first week of March 2020, and then he went home with the camera to upload it into his computer, and then everything went into lockdown. And then he spent like 2 weeks. He was living here in Austin and he said, well, if I'm going to be isolated, I might as well be really isolated. And he got in his truck and he drove to this ghost town, which he had but wasn't living in. And he took the camera and you're like, I don't know what he took. Okay. He took my camera. He took the Daily Stoic camera. And then he started, uh, just messing with it. Like everyone did during the pandemic. It was boring. And he, he was like, can I shoot a sunset? Can I shoot a time-lapse of this? The, the stars coming out, you know, and he just started messing around with it. And it was fascinating to watch this blow up. And then I, it was like, oh, we were, we were, I think we'd been shooting like a promo video, but the idea of, of just making stuff about what I'm doing and what's, that was kind of where I got that idea. And so, yeah, you, you, you don't have to see yourself as a front of camera person. Maybe you've never been that way. Fuck, I'm forgetting his name, which is shitty because he's awesome. Who's the lawyer who sits in his car between—

Oh, Jefferson Fisher.

Yes, Jefferson Fisher. He's amazing. I mean, he's a lawyer and he's filming in his car while he's waiting for court dates. It doesn't take that much, but his stuff is so good that it started to blow up. And now that's his set. His car is his set, right? Right. Um, and probably the, the set stays the same, but the, you know, the quality of the, the filming gets better and bigger, and I'm sure he's moving into other stuff. But whatever it is that you do, how do you find a way to explain it and be compelling about it? And, and like, I will say, like, your first stuff is gonna suck. Like, my, the first, uh, article I ever wrote was horrible. The first public talk I ever gave was horrible. I'm sure the first Even just the first narration, like if you went back and you looked at the first times I was reading the Daily Stoic email to audio, I'm sure they're really bad. But you know, now I've— I can't do the math, but literally thousands of them. I'm decent at it. And you know, I had the excruciating experience last year of doing the 10-year anniversary edition of The Obstacle Sway. And so first I had to reread a book I wrote in my 20s, and that was horrible. And then I had to listen. I was like, but I was like, guys, I'm not gonna do this audiobook again. I was like, I'm not adding that much stuff. Can't AI just like do pickups? And they were like, no, no, you need to listen to this. And like, my voice is different, my intonation is different, my ability to do voiceover work is different. And then that's because, oh yeah, in the intervening 10 years, I did 7 or 8 other audiobooks. I've done thousands of episodes of the podcast. I've done hundreds of videos. You have to accept, like Hemingway said, the first draft of everything is shit. And he means everything, not writing. Everything. The first draft of everything is shit. And when you realize that and then you get comfortable with it, that's the only way you're going to make things that don't suck.

I like that. So reading the book Wisdom Takes Work, something that stood out to me is these different characters through history and how the act of writing and publishing changes their entire world.

Yeah.

So I think of like Montaigne, right? Live one life in public service and all of that, and his life completely changed when he went and started writing and publishing.

Well, and there are actually kind of three worlds. Like, he's this, uh, public, uh, lawyer and politician, and then he retires to write and think. But he never intends to publish. And, and, and so it's just this fertile period of creativity and thinking and riffing and reflecting. And then he publishes and then there's this sort of sensation. And then there's this second period of, of, of that, uh, I guess a fourth period of what you do after now you have an audience and you've gotten feedback from the audience. But yeah, I think, uh, that making stuff cha— changes you because you're, I have a chapter in the book on, on how writing helps you think. Uh, because you're, it's not just that you're thinking about it, it's that you're thinking about the best way to say it, and then you're putting it down and then you're editing it, and then you're having an editor look at it. And it's the process of going over it over and over and over again that helps you refine and crystallize what you're saying. And so for me, that's why the writing part of it is always the same. Once it's, once it's written and published as good as it can be, whether it's in long form or, or short form. Then it can be made into other stuff. But it tends not to go the other way. Like I tend not to come up with a video and then back out from the video like a book idea.

Yeah, that makes sense. What would you say of people who are thinking about getting into creating content of like the impact that it can have on their life, or especially if you're trying to create content that has real meaning?

Well, I would just say, You know, what is your medium? Like, what is the thing that lights you up that you love? So for me, that's writing. And then I have these other ones that I'm interested in, but writing's the main one. So I always think about, like, the reward or the success at all this stuff shouldn't be that I don't get to do the thing that I love. It should be helping the thing that I love. So that's like a big one, right? Like, I like writing. That's what my, what I wanted to do. So I have to, I have to kind of protect that. Um, but also what I understand is that like, uh, the biggest book in the world is going to reach a fraction of the amount of people that a video or a tweet or an article or a podcast gets. Like they just different, different mediums have different potential audiences.

I mean, at launch, if you sell 10,000 copies of a book, that is a wild success for—

That will put you on the bestseller list for sure. And if a video does 10,000 views, it's like, yeah, exactly. And so, you know, like the emails, like when I pull up KID and I look at how many email opens we've had in the 10 years or whatever, it's in the hundreds of millions. And I mean, I probably wouldn't be sitting here if I'd sold hundreds of millions of books. It's a different, I mean, it's different. One is free and one is not, and one can be easily forwarded in a way that, you know, another can't. But the point is like, how does, how are these, how are you harnessing the potential power of these different mediums to reach all the people that you're capable of reaching? And not being snooty and going, well, like, like me personally, I don't, I've listened to like 5 audiobooks in my life. I just don't, I don't like audiobooks. I love that people like audiobooks because I've sold a lot of audiobooks, but like, I, that just doesn't do it for me. I don't like listening. To books. I like to sit and read them. Um, but like, I try not to yuck other people's yums, you know? Like, I, if that's what gets you reading, that's amazing. And what, what is exciting to an author is that the idea is going into someone's brain. And so, you know, you hear people go like, TikTok, they don't like TikTok, or they don't like this one, or they don't like that one. And it's like, I just try to think, hey, what, What is this medium good at communicating and what do I have that could go in there? And that's kind of how I think about it.

Yeah, I like that idea of bringing it to all these different mediums. Writing is the core thing that you do. Uh, I believe there's one year out of the last 15 years that you haven't published a book.

That might be true.

I looked at it and I was like, I don't remember the year, but it was sort of like, okay, what happened in 2016 or something like that? I think you published two books the next year.

So no, no, I did two books in 2016.

Okay, so maybe it was 2015 that you—

Maybe. No, yeah, I don't know exactly. There's a lot of books. There's a lot of books. I have, I, they don't always, when you work on them and when they come out can be very different things. But I try to always be working. Like Wisdom Takes Work came out 3 weeks ago. And like, the hardest part for me of putting out a book is that it's very disruptive through the book I am writing.

You're almost, you're annoyed almost that all the work to promote this book because you're like, hey, I've got a book that I'm working on right now.

Yeah. Well, look, and when I started, like when my first book came out in 2012, they were like, do you want to do this radio interview? And you're like, sure. And they're like, okay, it's going to be from 7 AM to 7:07 AM, you know, in this market. And you're like, okay, I'll call in and do that. And now everything is like a 3.5-hour podcast. And so it just, it just takes so much more time. Uh, and so it, you know, I, there's a difference between writing and publishing. You have to do both, but, but mostly what I love is writing and that's what I love to be working on always.

What does your habit look like in, in, I guess to build that consistency of writing, I assume every single day, how do, how do you block out the time for it? What does it look like in, in your schedule?

Most days, like today, I dropped my kids off at school. I went for a run around Town Lake in Austin. I got to my office and I started writing and I did 2, 2 and a half hours. And then later in the day, I had a podcast and then I did some sort of thinking and prep. So I talked to my research assistant. I'm ready for what I need to start on tomorrow. And it's like that pretty much every day.

The prep is really important. That was the thing when I struggled with a writing habit is I realized that I was like draining a well every day. And then I didn't have something that was refilling it of like the time with the conversations with the research assistant or the time that I was consuming other content specific to what I was doing. So the time that I made a lot of progress in my book is when I would write for a couple of hours or even just an hour and then later in the day have an interview with someone for the book, you know, or something else. And then it's like, oh, now I have what I need to write about the next day and the cycle continues.

Yeah, I don't think writer's block exists. I think you just don't have the material. And, and most of the time when I'm having trouble figuring out what I want to say, it's because I haven't studied the thing deep enough or I haven't gotten the, the thing arranged the right way. The right, the writing should come pretty easily. It's, do you have what it is that you're going to say? And if you're trying to do, trying to make that up as you go, that can be very tough. So, um, yeah, I, I, whenever I feel it slowing down or I feel like I'm struggling, I go. What are the inputs that I need? Because every bit of writing you do is a lagging indicator of something you've learned or read or researched or thought about or talked about. Could have been yesterday or could have been 10 years ago. I mean, there's a chapter in this book that, like, I opened up a book that I read in 2006, and it was like, marked out on the page everything I needed for the thing that I obviously never even conceived that almost 20-plus years later I would need exactly. So it's all a lagging indicator of the pre-work that you're doing, for sure. And then Hemingway has a great line about just stopping in the middle of a sentence for the day. So you have something to get your momentum started with. When you sit down the next day.

Yeah, I like that.

Okay.

Something I've seen you do, I think it was maybe when I came out to your ranch to visit and you had a home office then, and I don't remember which book you were working on at the time, but you got out a clear plastic box of hundreds and hundreds or maybe thousands of note cards. And you're like, this is that book.

And then there are other tubs and you're like, that's every one of my, every one of my books is built out of The note cards, which are, you know, I read and then I transfer the stuff onto note cards. Those are the building blocks for the books. And part of the reason, talking about sets, part of the reason we, we bought this building and setup is that my wife was just tired of the note cards of them just overflowing our house. And, you know, she's like, you can't just have tens of thousands of legal documents spread all over because you happen to be researching something in a moment. And, and so it was, it was, it was good to have a. A permanent place. And then, you know, I, I just took over the, you know, the upstairs of the building. That's where I lay out all the stuff. Um, so yeah, I think I need to kind of, uh, I'm doing the building blocks of the research, but then it's also the physical laying out and seeing it all before me is really important for me to wrap my head around.

So I see a lot of authors right now moving a lot of their, like, the organization of their reach, their agenda, all of that to AI. Where they can ask those questions, but you lose that whole physical aspect of it.

How do you— We don't just lose the physical aspect. You lose the purpose of doing it, which is you doing it. Like you're, you're supposed to know the stuff that you're writing about. Yeah. You're supposed to know what you're writing about. Um, and it's in the engaging deeply with the stuff over and over and over again that you develop the sense of, of what you're trying to say and the best way to say it. I actually opened the wisdom book with this story that's 2,000 years old. Seneca talks about this wealthy Roman who wants to impress people at a party. And so instead of being smart and having anything to say, he buys these slaves who are very well read, and their job is to whisper things in his ear that he can repeat at parties. And he thinks he's figured it out. And, uh, and he's at a party and, you know, he thinks he's impressing people with these stories. And a friend comes up to him and he says, you know, uh, this is such a lovely party. I didn't know you're so smart. Uh, he says, have you ever thought of wrestling? And he says, wrestling? I'm an old man. And he says, yeah, but your slaves are young. Maybe they could do it. And, and the, the point is you really can't have anyone do it for you. A research assistant can help with things, but ultimately, if The material is not over here and then coming through you and being processed and put on the page. And then there's this kind of feedback loop. You're just not, you're not doing the, you're not doing the work.

And, um, and some might say that wisdom takes work. It does. That's it.

Seneca's line was, no, no man was ever wise by chance. It takes work and there are no shortcuts. There are no hacks. There's no way to get out of it. Um, you have to do it and you have to do it a lot. And I think people who are thinking, oh, I'm not gonna, I'm just gonna type in what I want from ChatGPT or whatever. I, I, I think you're gonna be sorely disappointed. First off, 'cause it hallucinates like 20 or 30% of the time. And then, um, I'll, I'll give you, I'll give you a funny example. So, okay. So every, I, I, I take a lot of what I've read and I write it down onto note cards or I type it out. I, I, One of the practices I have is when I find really great sentences or paragraphs, I will type them out. I want to feel it running through my hands. And then who knows, maybe I'll use it. So I'm copying and pasting. Sometimes I'm typing it, printing it, cutting it out, pasting it on a note card. Or my research assistant was finally like, you know, you can just print this on the note card. And I was like, yeah, probably. But the point is that it's an arduous process. But the point is I have typed Many of the greatest sentences ever written into Gmail. Sometimes I'll just do it in Gmail and, you know, Gmail, uh, uh, just like your phone, it predicts what you're going to say next. Right. And so if there was anything that it should be able to predict, it's this, because this sentence isn't a new sentence. This is a sentence that's already done and in the culture, in the world, and it never gets it right. It always. Suggests a totally unhelpful, worse way to write this sentence. You know, you could be typing the conclusion of The Great Gatsby, one of the great paragraphs of the English language, and it's going to be like, do you want me to refine that for you? And it's like, how dare you? Don't you fucking touch this. The point is, like, it doesn't know. It's good at pretending to know. And there are things that can be helpful with, and I Um, I use it sometimes, uh, but, but most of the things worth doing, you still have to do yourself.

I like that. I want to leave some time for questions. So if you have a question, start thinking about it. I know a few people have already mentioned to me questions that they want to ask. Um, I've read a bunch of your books. My favorite one is Conspiracy.

Okay.

And it's like a left turn from, you know, pretty much everything else that you've written, but I just want to hear you talk more about the process of creating that book. Uh, it's a totally different style of writing. And, uh, I know you found yourself in this like weird situation where you're like, wait, I'm talking to all the players.

Yeah.

So talk about that more.

How I like to take on projects that however they might do commercially, I will get better for having done them. And so those are the, like, conspiracies is the genre, I guess, would be narrative nonfiction. So my favorite books are in that category. Like when people come in the bookstore, I'm like, have you read these books? These are the, they're the ones I tend to rave about. The Tiger, Night of the Ghosts, Shadow Divers, Tunnel 29, River of Doubt, Destiny of the Republic, The Art Thief. Those are the books I love. So I wanted to do a book like that, and this story kind of fell in my lap. And so I signed on knowing I was biting off way more than I could chew. And I was, like I said, I had to read, I think I read 20,000 pages of legal documents for that book. And I not only didn't go to law school, I dropped out of regular school. So it was tough, but I learned a lot. I think if I was doing the book now, would I do it a little bit differently? Probably. Do I hope I could do it better? Sure. But I really loved the challenge of writing it, and I'm proudest of it. I wouldn't say it's my worst-selling book, but it didn't sell anything close to some of my other books. Um, it's the only one that's been optioned to be a movie, um, which may or may not happen. It's been optioned every year for 7 years. So that's a whole other world that I don't understand. But my, for me, that process, that project was, can I do something different than I've done before? And that, I, that's how I judge it as a success or failure. And I'm in the middle of doing a very different book. Kind of in that style now, but the idea of just like, don't do the same thing over and over again, try different stuff. Sometimes it really works, sometimes it doesn't, but the trying is the important part.

Is there something that you learned from like creating in that medium, that style? Like I imagine it being like a musical artist being like, oh, I'm going, like, you know, it's like Beyoncé doing Cowboy Carter, right? Like switching that you then brought back to the rest of your books.

That's a good question. Uh, I mean, it was different writing about people who are alive. We had to do a lot of different research. I had to learn how to interview people. That was challenging. I had to describe like places and people in ways that I hadn't. So just like, just the writing itself was a challenge. And then what else would I say? Anytime you're doing something outside your comfort zone, it's a good thing. It's going to make you, it's going to make you better and more confident. And that's why you should do it.

I love that. All right. I believe we have a microphone. Haley has it. Look at that.

We got a few questions.

I am the keeper.

So, so Ryan, um, I know, you know, Angela Duckworth's work. I love that book, but maybe my favorite part was basically the appendix where she wrote about parenting for grit. And when I think about wisdom, if there was a chapter in the appendix of this book called parenting for wisdom, what would you put in it? Ooh, that's a good question. So we just spent the summer in Greece. My son got hooked on this podcast that everyone with kids my age knows about called Greeking Out, which tells Greek myths for kids. And it was funny, as we're traveling around, we'd see people with kids the same age and we'd be like, why are you here? And they'd be like, well, our son likes Greeking Out. And And, but to me, the lesson wasn't just like, we went to all these cool places and we learned about things. But to me, what I think my, the thing I'm proudest of or think is most responsible for my success is like, what do you do when you have a kernel of interest in something? Right? So you have curiosity or interest. Do you have the skills and the competence and the creativity to like figure that thing out, to like go down the rabbit hole? That's what, makes you want to write a book about something. That's what makes you, you know, something's not working and then you explore it and then all of a sudden you have an idea for a company or you have an idea for, uh, you know, a nonprofit or whatever it is. Like, what do you do when you're interested in something? Do you have that skill? One of my favorite chapters in the Wisdom book is, is the Lincoln chapter. But I think people think of Lincoln as this sort of person who was just born with this profound, you know, hatred for slavery, which he didn't. He always knew it was wrong, but he, like everyone else, just assumed there was not only nothing you could do about it, but that, like, he was in the minority. And it's actually this remarkable thing after the sort of a number of laws get passed and he just goes like, I want to figure this out. And he goes to the Illinois State House. He also uses the Library of Congress, which Congresspeople used to use to read books about things. But he goes in, he's like, well, what did the founders actually think about slavery? What are the records of the meetings and the votes and the conversation? And he just does this, like, deep dive into the institution. He finds out, oh, like, actually, all these things that the South had been using as a statement in support of slavery, the evidence didn't support it, and that actually the founders were ashamed of it. And that's why the word doesn't appear in the Constitution. And that's why there were all these compromises. And that's why he's like, the penalty for trading in slaves after the, the 1820 or whatever was death. He was like, you don't punish a thing that is just kind of illegal with death. And so anyways, he does this deep dive. And I guess to go to your point, what I try to encourage in my kids And what we work on, what I think wisdom is, is like when you have an interest in something, something doesn't add up. Do you, how do you go crazy about that thing? And even as a parent, like how many amazing parenting books out there and memoirs and biographies are out there? And then parents are just like, well, I'll figure it out. Or like, you know, it's natural. You should know how to do it. It's no, there's infinite amounts of wisdom and experience and knowledge out there. And like. Go after it. And that, that skill to be like, hey, this thing was interesting to me, so I'm going to read every book about it and watch every video about it and ask every question about it and travel. And that's, that's what life's all about to me. If you both were, had a blank slate or in your 20s starting in today's landscape, what would y'all both start? Like, how would you navigate today? Ooh.

Nothing immediately comes to mind. I like what I'm doing now. So I want to, I want to do the same thing.

That's not fair.

Um, yeah, that's off the table. You can't, I can't cop out.

I don't know if I don't know if it's allowed to be off the table because I like, there's the thing you love to do. And like, I love writing. That's what I would still want to be doing. Would I have found maybe a different way in? Would I have built my audience a little bit differently? Maybe. But like, what I love to do is something people have been doing for thousands of years. So I think sometimes we're too, we'd be like, oh, AI is hot. Go into AI. Like chances are whatever the thing that is hot or working right now, like you're already too late on. You should find the, like Robert Greene's advice to me on books. He was like, you gotta find, um, something that's both timely and timeless. And so like the timely is your way into it, but the timelessness is what makes it worth actually investing. Investing in and going into because you don't want to, you know, the people that were all in on crypto a few years ago are all in on AI now and a few years before that they were the another thing like going to whatever the, where the energy is, is not what it's about.

I think that the thing, so maybe a way to distill down the question is like, what is the thing that you deeply love that you would do even if you didn't get paid for it? Right. And you're going to be writing. No matter what, I'm going to be creating tools that other people use. Like, it brings me a lot of joy to meet Ryan's team and talk to them about how they use Kit to send Daily Stoic and the Daily Dad to hundreds of thousands of people. And they're like, hey, can I have a feature request?

Is that okay?

I'm like, yes, tell me, right? Because this is the thing that I love. And so to me, it's not just making something. It's making something that is used by others. And so that might not be software, that could be something else, but I can guarantee, you know, whatever form it takes, it would be something in that way. So starting over, it would be figure out like what is the core production function of what you love to do and then apply it in some way that is like commercially viable enough that you can keep doing it.

All right.

We can go over there.

All right. So one of the hardest things that I've come across in business is finding where demand and what you love to do intersect.

Sure.

So when it comes to content, going to the beginning of the conversation, did you have a time in your life, Ryan, where that demand hadn't showed up yet? And if so, and you're shaking your head yes, did you keep going to see if there would ever be that demand? So my first book was a book about marketing and it did okay when it came out. It got a lot of attention. It hit the bestseller list. There was sort of a track there that I was on. And so when I went to my publisher for my next book, in traditional publishing, they usually have the option or the right of first refusal on your next idea. So you have to pitch them your idea. So when I went to them in June of 2012 and had said, you know, I'd like to write about an obscure school of ancient philosophy. They were not super pumped. Um, I, I, I had a sense it could be big and interesting and I had some reasons for thinking that, but I didn't know and they didn't know and there wasn't the demand. There wasn't the audience there. There was my interest and there was enough to make it, I think, not a complete waste of my time. And they obviously saw enough in it. To make a small bet, but I think I got paid half for The Obstacle Is the Way. I got the advance was less than half what I'd gotten for Trust Me, I'm Lying. But it was what I wanted to write. And I had a day job and a marketing business, so I could make that bet. But I didn't know and they didn't know. And it's, I think, In retrospect, it obviously worked out and seems obvious, but it wasn't obvious at the time. And so if I'd done the book and it had sold zero copies and, uh, I hadn't had fun doing it or whatever, maybe I wouldn't have kept going, but it was an iterative thing that happens over time. So you have this sort of sense and then you, you, maybe you get that product market fit or you don't. Sometimes you get it on the first try and sometimes it takes 20 tries, but, um, none of my stuff has been huge overnight or the day it came out. Uh, almost all, like, The Obstacle Is the Way sold more copies every year, sold more copies than the past year every year for like 10 years. Um, and so that's, that's, some people have monster success. They do all that in the first year. None of my books have done that. They've all been, sort of growers. Um, and so you got, that's why you have to really like it. You can't just be like, I'm doing it and I want the audience to tell me if I should keep doing it or not. But, um, that's been my experience.

One of, I think the most entertaining criticisms that I've heard of you is that, uh, you talk about stoicism for the money.

Yeah.

Because I remember probably around like 2013 time period, you being on like Tim Ferriss's blog around that time talking about it. And no one had any clue what it was. It was not a popular thing. And it was like, okay, this is something that Tim and Ryan are kind of into.

All right. Yeah. It seemed like a nerdy thing that, that I was interesting to a small group of people. Um, and then, yeah, in, in retrospect, uh, it's a, it's a, it's a sign of success that people were like, oh, of course you, you did it only because you knew it would work, but you don't know it would work. And if they did, um, then my publisher was sandbagging me. And if I did, then I'm, if I knew it was going to be this big, then I'm a horrible negotiator because I accepted the advance, you know? Um, so you're, you're taking a flyer on it. Um, and, but you should do the thing that you're, you're interested in. They told me, my publisher told me later that they, they were basically just humoring me. They, they hoped I would do this book. It would, come out, do whatever, and then I would do more marketing books. But that wasn't what I wanted to do. That, that just seemed like not what I wanted out of my life. And so that wasn't the direction I was going to go.

That makes sense. All right, who else? I'll let Haley choose.

Uh, so I have a question around balancing like the art versus the commerce. And I mean, both of you both create, and so I think you could both speak to that, but I'd love to hear your perspective on how you think about that and has that ever muddied the waters in your decision-making?

The advice that I got that like you, you make money to make more art to me is one of the ways you address that tension. If, if you're bad at running your business, if, if it's, if it's not reaching an audience, if no one's liking it, you're not selling, makes it hard to keep doing the thing, you know. So one of the, one of the things I think about is like, how does this help me do what I want to do, which is make and talk and think about Stoicism and make it accessible and practical and usable by people. But there's tons of stuff that I don't do that I think would do well. Um, from, you know, like basic things, like, as I said, we work with Backyard Ventures. They previously were with Amazon. They did the podcast. Like, in our contract is a whole bunch of things I won't accept as sponsorships. Like CBD or gambling or crypto or things that, like, I don't care if you do. It's just I don't want to tell you to do because it doesn't align with my values. And I just don't think it pairs well next to what I'm talking about. Right? Like, so, so like I decide what sponsors I work with or not. I decide what people I'm going to have on my podcast or not. I'm going to, you you know, what events I'm going to appear at or not. All of the— that's that same tension of commerce and art values and principles. Someone messaged me the other day. They were like, hey, I think there's a 7-figure business here in a stoic line of supplements. And I was like, look, I don't have any problem with supplements. I took some this morning. I just— I just—

and I—

it's not even an ethical thing. I just personally don't want to spend my time being involved in a supplement line. It just doesn't— that's not what gets me out of bed in the morning. I'm sure someone else will do it or might do it. Seems kind of lame and weird, but if it's not to you, go for it. But it just, that's not what I, I'm not writing about this stuff so I can sell supplements. This is not what I'm doing. So it's not what I'm going to do. And so I think it, with success, with an audience, with a platform, I think comes certain obligations. Um, I won't tell people how to make those choices, but I think you, each person has to think about what they're, what they're comfortable doing and not doing for money. And, and I think you're sort of defined by those choices that you make.

Yeah. So I run a conference called Craft and Commerce, and the idea behind the whole event is finding the intersection of these two things. Because there are so many people that are like, I am just here to make art, or people who are like, I am just here to make money. And I really don't like either of those worlds because the person who is just there to make art usually can't keep making art because they don't have a way to fund it. Like, unless you happen to know the Medicis and you're like, you know, in this like patron and you get someone to pay for it, you can't do it. The best thing is to be able to be your own patron. And, uh, fund it in those ways. So there's a quote that I was attributing to Seth Godin, and then someone told me it's not Seth Godin, so I don't know, but it's just, profit is permission to do it again tomorrow. And so I think of that in running a profitable business where we can make decisions, we can set our time horizons of like, all right, we're not here for an exit in a year. We're not like scrambling, you know, having to take on the sponsor we don't believe in cuz we have to make payroll, any of these things to Yeah, like when you have a successful, profitable, sound business, you're able to say, I don't want to do that.

I'm not going to do that. And that's like a really, that's freedom. I was able to take the step back on the Stoicism book because I had my own business and I'd, you know, made certain decisions. Um, I tell a story in, in the book that came before this one, uh, Right Thing Right Now, which is about the virtue of justice, um, which was a formative sort of encounter I had when I was at American Apparel. Dov Charney is this controversial, problematic figure. Put all that aside. Someone was talking to him once, and I was sitting there, and they were like, you know, I think we should just move some of the factories to Guatemala, and we'll pay a lot less in labor, and it'll be more profitable. And I mean, first off, the stupidity of it's called American Apparel. It has to be made in America. That's the whole point. But he was, he was saying like, He was, he said, if all I cared about was making money, I'd just be a drug dealer. And, and I think about his, his point was that there, if, if all you care about is making money, you're probably not doing whatever it is that you're doing. There's way, like you'd work on Wall Street or that you, you'd, uh, be a criminal. There's way, if, if all you care about is extracting money and as much of it as possible, as quickly as possible. Don't do whatever it is you're doing because it's probably not that thing. So you've already said, no, no, I care about art or I care about my audience or I care about this or that. And so you have to remember that that's the thing that's important. And then if you do that well, chances are you'll be fine. You'll be able to make money and you should be able to make money. And are some things going to make more than others? Sure. But like doing it to make the most money possible as quickly as possible is almost certainly not the right set of standards to judge whatever it is that you're doing by. Yep.

That's good.

Who runs Craft and Commerce, Nathan Barry?

Uh, you do, Haley.

Thank you for that.

You attend.

So I attend.

He attends. He goes where I tell him to go.

Okay.

One quick, like the idea, something a lot in your work is longevity, right? And like doing this for a long period of time. And that's been like quite a lesson for us in like what it takes to get compound returns. We, uh, we ran the event for 3 years, sold more tickets every single year. We're ready to sell in our 4th year. And then COVID happened.

Yeah.

And then we didn't pick up where we left off. We like almost started over. And then 3 years in a row, like sold more tickets. And then in our 4th year, finally sold out. So like 7, 7 events over what, 9 years, I think is what it finally took to sell out like our dream life.

Doing it as you're doing it, or it's not. Yeah. Yeah. It makes the payoff need to be bigger and faster if you don't like it as you're doing it.

And you have to set everything up so that you can show up and do it over and over again. Would I do this even if it didn't make money, didn't sell out, any of those things? It's like, yes, absolutely.

I heard now that it sold out, Ryan said he would come and speak at it.

No?

Is that—

oh, that's what I thought I heard.

How far, how far do I have to travel? That's the question. To Boise?

Yeah. There's, there's not a direct flight, but don't worry about that.

Nathan's a pilot now.

Yeah, I'll come, I'll come get you in my small plane.

That does not make it more attractive.

So for a lot of creators, there's this tension between part of your job is being creative and having endless ideas, but also navigating opportunity cost. Because every time you say yes to one thing, not only are you saying no to many others, But saying yes to the new thing pulls you away from being able to continue saying yes to everything else. Both of you have multiple projects you've spun up over the years. You know, Nathan, I think you're a little bit more focused with Kit, right? But Ryan, you have Daily Stoic, Daily Dad, you have Brass Check, like you have all these other things plus writing. How do you decide which of the new ideas is actually worth pursuing because it is worth that opportunity cost?

Yeah, opportunity costs are the tricky thing. Everything you say yes to is saying no to something else. Uh, you gotta know what the main thing is and that's gotta be the main thing. Um, when I take on other things, they have to be in service of that. So yeah, sure. Making videos and, uh, you know, giving talks or, um, maybe it seems like it's a distraction from the writing, but if it's bringing people to the writing, then ultimately it allows me. To keep doing it, or it's, it's developing skills that allow me to be better at the main thing that I do. So you got to know what the main thing is, what the main driver is, what, as Nathan was saying, like, what would you do for free? And are these other things that you're doing supporting that, or are they taking you away from it? And that, that's kind of the test that I have.

Yeah, I add that early in your career, saying yes is the most valuable thing. Say yes to everything. And then the hard thing that comes later is that the skill that got you there of like saying yes, being eager, jumping on things will be absolutely your downfall when you have any kind of success. And so you have to learn an entirely new skill of saying no to almost everything. Jason Fried talks about this where I think he says that no is a scalpel and yes is like a blunt force, like a hatchet. Because if you say yes to something, then it like has all of these other ripple effects. Whereas if you say no, it's like a precise thing. It only affects, uh, that one thing. And so it's just figuring out what stage you're in of like, are we trying to create more opportunity? Are we trying to curate the opportunity that's inbound or what we're seeking out? And exactly what Ryan said of, is this in service of the primary thing? So an example of that is I have a side business. that I started called Paperboy, which is a newsletter marketing agency. And I didn't do it for the money. I did it because I needed a team separate from Kit that could solve, that could take on some of these big clients and could handle this when, uh, we didn't have the resources in-house or the team in-house to do it. And so when Matthew McConaughey came to us and said, hey, I want to launch a newsletter, and then we had the team in Paperboy that was able to spend a huge amount of time like getting the bumper stickers on the back of the Airstream on the landing page for Matthew's newsletter, like just right. And so in creating this other agency, yes, it makes money. Uh, it's, it's quite successful, serves a lot of amazing clients and all of that, but it's in service of the main thing, which is allowing me to bring more incredible creators to Kit.

All right, friends, the last question is gonna go to the highest bidder. What are we giving up?

What is the unit of ecnole?

Like, I don't know, whatever, whatever anyone's willing to offer. Last question of the evening.

Uh, this question is for Ryan. Uh, which principle or practice of Stoicism do you find the hardest to apply to your life still today? Ooh, that's a good question. So, uh, the last 6 years I've been on doing this series on the cardinal virtues, courage, discipline, justice, wisdom. Each one I've found was like the hardest, most sort of urgent one in the moment that I was working on it. And what's interesting about the virtues is that as independent as they are, they're all interrelated and inseparable from each other. So it's hard to say which one is like the one that I struggle with the most, because the truth is I struggle with with all of them. But I think discipline, we tend to think of as this sort of physical thing. Most of the virtues have a kind of a physical component and an emotional, spiritual component. I think physical discipline, pretty good at keeping emotions, temper, frustration, resentment, anxiety, those kind of emotions. I struggle with that the most. And so that That part of Stoicism is the one I'm always like, feel like I'm making the least amount of progress in. But that's the point, is it's supposed to be something you're working at. It's not, you don't just read this stuff and then you're magically good at it. If only that were so easy, I'd have sold a lot more books. Uh, it's, it's the idea and then the application. That's, that's where the rubber meets the road.

That's the hard part. Um, so everyone should check out the book, Wisdom Takes Work. I would say sold. You know, everywhere books are sold, but you should specifically buy it at a very specific bookstore.

There's a place down the road. Yes.

Uh, you can go visit The Painted Porch. Please do buy it in person. Come see the set, see all of that. You'd be one of the people who's like, oh, I've seen this on the videos.

Yeah.

Uh, and then you also do sell it online through The Painted Porch, right?

Yep.

So, uh, where's, what's the URL for that?

Thepaintedporch.com.

Perfect.

But also it is the final series, right? Or it is the final installment in the series and it is officially a New York Times bestseller, right?

Congratulations.

We all know how hard it is to be a creator, and I don't think even after the multiple times that you've been a New York Times bestseller, it's easy. So congratulations.

Thank you very much.

Thank you for coming. And thanks, y'all.

Thank you very much.

Thank you, Ryan. Thank you, everybody. If you enjoyed this episode, go to YouTube and search The Nathan Barry Show, then hit subscribe and make sure to like the video and drop a comment. I'd love to hear what some of your favorite parts of the video were, and also just who else you think we should have on the show. Thank you so much for listening.