The Bossticks - #83: Ryan Holiday - Perseverance, Living In The Moment, Failure, Perception, and Creating Perennial Sellers

Episode Date: October 10, 2017

On this episode we interview 6x Author and Marketer Ryan Holiday (@ryanholiday). We cover a lot of subjects in this interview including what it took to become an author of 6 books at the young age of thirty and become the chief marketing officer of American Apparel and market for personalities like, Tim Ferriss, Tony Robbins, and Tucker Max. We also dive into the ancient philosophy of Stoicism and discuss the stoics response to failure, living in the moment, and perception of the world around us. The interview raps up with a conversation on Ego and how to create work that stands the test of time.  To Connect with Ryan click HERE To Learn more aboutt Stoicism click HERE To connect with Lauryn click HERE To connect with Michael click HERE This episode is brought to you by The Skinny Confidential Bombshell Body Guide and Meal plan.  tired of combating inflammation & bloat? Want to feel lighter and sexier? Check out lauryn's latest 7 day meal plan. In this simple & super effective plan you'll find: + tsc grocery list with every ingredient you need for the 7 days. + what the f*ck to do when you love carbs guide. + quick and delicious recipes: breakfast, snacks, lunch, dinner and dessert. You will also find 28 weeks worth of fat burning, muscle toning, 27 minute long, effective workouts you can do at home with no equipment. USE PROMO CODE: HIMANDHER at Checkout for 20% Off

The following podcast is a Bostick media production. She's a lifestyle blogger extraordinaire. Fantastic. And he's a serial entrepreneur. A very smart cookie. And now Lauren Everts and Michael Bostic are bringing you alone for the ride. Get ready for some major realness. Welcome to the skinny confidential, him and her.

What's up, everyone? Welcome back to the skinny confidential, him and her show. So today we're going to be talking with Ryan Holiday, who's an author and master marketer. But first, I'm Lauren Everett's, the creator of the Skinny Confidential, which is a blog, podcast, and YouTube channel. And I'm Michael Bostic. I'm an entrepreneur, marketer, business builder, and operator, and now a podcaster. Okay, so as Lauren said, today we are interviewing an author that I really admire. His name is Ryan Holiday.

And to give you a little background on Ryan, at the young age of 30, Ryan has written six books, which include The Obstacles the Way, Growth Hacker Marketing, the Daily Stoic, and Ego is the enemy. I think I've shared or talked about a few of these on this podcast and on Lawrence Blog. He recently released a new book called Perennial Cellar, which we will get into in this interview. He is also a marketer, and at the young age of 21, he was the CMO of American Apparel. Since then, his company Brass Check has worked with businesses and personalities that include Google, Tim Ferriss, Tony Robbins, Tucker Max, and Ariana Huffington. No big deal.

So, yeah, this interview is one of our longer interviews. Lauren and I have been a fan of Ryan's work for a while. So when we got the opportunity to interview him in his office in Austin, Texas, we took full advantage. And can I say that he has my dream library? He has the library, kind of like Beauty and the Beast, but without the ladders. it's Michael's dream and we actually like Michael said flew to Austin to interview him we flew in and out it was like a one day trip we were on rainy street we're on rainy we went to the restaurant perla which is so good is it Perla's or Perla it's one of those and we had oysters and they had

oyster shooters that were spicy we had a little rosé really good really fun but quick in and out I bowels loved awesome though Austin's fun okay so the first half of this interview really covers a lot of Ryan's background in his career. We talk about what it was like for him to drop out of college and apprentice under the author Robert Green, who wrote the 48 laws of power. We also talk about what it took to persevere through hardships at a very young age and the importance of reading, which I love. And then the second half of the interview covers a lot on the subject and philosophy of stoicism. For those of you who want to learn more about stoicism, stoicism is an ancient philosophy that core value is basically rooted in the belief that we can't control

the world and events around us, we can only control our response to those events and how we perceive them. It's my favorite set of philosophies, and Ryan is definitely an expert on the subject. So for those of you who like the mindset stuff, the second half of the show will be right up your alley. Didn't you read one chapter a day of his stoicism book? Well, he has a book called The Daily Stoic. You read one a day, right? You read a page a day, not a chapter. And I recommend it. Yeah, it's great. And you wrote in it. And when you weren't looking, I peaked at what you wrote. I journal in it sometimes. I journal. I always peek at your journal. Damn it.

All right, guys. So here we go. Hope you enjoy Ryan Holiday. This is the skinny confidential, him and her. Okay, Ryan, let's get a little background on you. So you have a lot of accomplishments at a very young age. Where did you grow up? Where did you go to school?

Give us the deets. I grew up outside Sacramento, which was a very boring place. Very sort of normal parents. Like my dad was a police officer. My mom was a school principal. So I was sort of on track to be like a normal person. I went to school in Riverside to be with my high school girlfriend, which went horribly. And then I ended up dropping out at 20 because I got a job working for a writer that I really liked.

So it's sort of I thought my life was going to go one direction. And then very quickly it veered in another direction. And it sort of hasn't stopped since then. Okay. So tell me about how. you started working for this author. His name was Robert Green. Yeah, yeah. So I was working for, I'd written an article about another author when I was in college for the college newspaper. And I was sort of using this newspaper as like a way to meet people that I wanted to meet.

In the way that some people would do it with podcasts, right? Like, it's like, oh, I'm going to do this thing. And then it gives me an excuse to like reach out and meet people. Like we're doing right now. Sure, sure. Well, so that's what I was doing. And then, so I was working for this author who happened to be friends with and all, worked with Robert Green and then as as that sort of evolved Robert was in the market for a research assistant and I was like that is what I was like put here on this planet to do like like I loved his books I was a huge fan of his writing I wanted to learn how to be a writer and like I don't even think that I thought that that was a job like that someone could get paid to like help someone else with their books and so I was sort of begged for it and my

first job for him was he was writing a book with 50 cent i think it's it's around here somewhere um he was writing a book with 50 cent and so my first job was just transcribing the interviews um so i just transcribed hours and hours of of interviews with 50 cent then you you like sat down with actual 50 cent no no no no like i would get the audio file of it and then i would have to transcribe transcribe this and so that was like my first glimpse into like how writing worked and how books would work and when you did this, did working for Robert contribute to you your decision to drop out or was that, did that come after? So I had another offer to drop out to work at this talent agency in Hollywood and I was like sort of really thinking about it. And then the Robert thing happened like at the same time. And so it was like I would have dropped out for either one of these probably. And so the chance to do both at the same time. It was like this is this is a sign. This will never happen again. I can't turn this down. And what are your parents thinking? they freaked out.

They thought it was a horrible idea. You know, like they had raised my sister and I to go to college. I think they took a lot of pride in us going to college. And I think a huge part of it was like they didn't want to be the parents of the kid who dropped out of college. Because it was just, I'm the oldest. And so I would have been the only one of any of their friends' kids who didn't finish college. And you're setting the example. Yeah, yeah, and with my sister.

And yeah, that's a good point I never thought about that way. I think one of the things I realized is that, you know, your parent's job is not for you to be happy. Your parents' job is for you to be safe and, like, not die. Like, that's your parents' main job is, like, is not for you to find your dream job and fill it with meaning. Your parent's job is to, like, make sure that you know how to, like, tie your shoes and you eat, you know. And so for them, that all they saw was the downside, right? That, like, I was, I had a scholarship that I was walking away from, that I'd, you know, I'd worked hard in high school to go to this college, that I was, I only had a year left of school.

You know, so all they saw was the downside. And all I saw was the upside. And so, you know, you're going to have these points in your life where you're sort of, you have to go, oh, I realize why you're giving me this advice and it comes from a good place, but it's too conservative. So I ended up doing it and it was, you know, we didn't talk for a long time. It was worked out now, and so it's sort of this thing that we don't talk about. They're okay with it now?

Yeah, well, of course. Everything turned out already. Yeah, yeah, it's like, let's pretend this never happened. But, you know, if I was living under a bridge somewhere right now or if I was still struggling to make it as a writer, that dynamic would change. I would think would probably have changed a little bit, but they were just, I think they were really scared

and they were really focused on how badly it could go. And I think what I realized is, one, how great it could go, but that it wasn't as bad as they thought. Like I think a lot of times when we face risks like that, we're thinking like, it's like, okay, if this doesn't go right, then this could go wrong, and then this and then, and then, yeah, you end up living under a bridge. And the truth was when I went to drop out, you know, I walk in the registrar's office and I'm like, you know, ready to drop out.

They're like, that's not a thing. You know what I mean? Like, they're like, this isn't like a, they're like, you just don't enroll in any classes this semester. And then you don't enroll the next semester. You just don't come back. Yeah, you just, you just don't come back until. You decide to either come back or it's, you know what I mean?

Like, there's no official paperwork that, like, was really involved in this in any way. I just, they stopped charging me for tuition and I stopped going to class. Like, that's what happened. It's strange to think about because, you know, for me, I was not always the best student, but I went through all the years of college, I was high school and finished. And I feel like I, if I was more focused on what I would, like, a career path or something there, not just, like, kind of hanging out and going through the motions, I would have got a lot more out of it. I think actually maybe now going back, I could get a lot more out of schooling.

Me too. Like a lot more. Yeah. But at the time, you're right. It's just like you don't really think like, okay, I could just leave. Yeah. And I wish that I had gone into it thinking that I might leave because like, so I was supposed to graduate in three years.

I was on track to. So I went to two years, but really I got three years if you think about it. But I did all the, I did all like the basic stuff first. So I went to college, but really it was like I just did an extra two years of high school. Do you know what I mean? Like I did. Like I wasn't like in any of these life changing class. Like I wish I'd taken, you could get everything out of college in six months.

If you went in there and you were like, here's what I'm here to learn, I think most people go and they're like, I know, I'll figure it out. But actually you'd be much better off going like, you know what it's like? It's like, you know in that show like supermarket sweep? Yeah. If you're just running around and you don't have a plan, like, it's probably not going to work out for you. But if you're like, oh, I'm going to this aisle. Like you're the guy that grabs all the most.

Yeah, exactly. Like, I wish I'd gone in going, like, here are the 20 professors that I'm going to meet. Here are the eight famous classes that I'm going to take. You know, these are the things that are going to set me up for what I'm, you know, I was just winging it. And then I got lucky, but. Yeah, no, I get, I mean, I don't want to go too deep into schooling,

but I feel like you're kind of doing a disservice to young people because at 18, you know, I get out of high school and I don't know what the hell I'm doing. And then I get there and they're like, okay, what about this elect? I'm like, yeah, that sounds all right. Like, that seems like it'll help me. But there was never a thought like, okay, I need to do this and take these classes and get interested. I mean, and it's funny, a lot of the classes were electives.

I remember it took like Greek mythology, and that was one of the class I was the most fired up on. Sure, sure. And then another one was on like water conservation. I was like, what the hell am I doing here? I get in trouble all the time because I think college was a waste of time and money for me. I really think that. Not for everyone, but for me.

For me. 30 or $40,000 a year is a very expensive price tag to pay to $2, figure something out. If you're if you're if you're if you're like here's what I'm doing and so I'm paying I'm investing 40,000 dollars a year in pursuing it. It might actually be a great deal. And I think it's the same since I dropped out. I hear from lots of people who dropped out and they're like I really don't like school. So or I hate my job. So I'm quitting my job or I'm dropping out of school and now I'm going to like figure out what I'm going to do. And it's like again, cutting off your education or your sources of income is a very expensive way.

to then go figure out what you're going to do. It's like when I decided to be, I had a very good job when I decided to leave that to become a writer, there was about a year learning from the college experience. There was like a year where I knew that's what I was going to do, but I spent a year saving up money, meeting people, like preparing. You got to like look before you leap. You know what I mean?

I think people leap right into college and then other people leap right out of college. Without a plan. Without a plan. Okay. Speaking of plans, talking about writing and marketing, which is both, those are your two professions now, I'd say probably more writing at this point? Yeah, it's about even. Yeah.

Didn't go to school for either. Always wanted to be a writer. Always wanted to go into marketing. Yeah. Yeah. I think it was that I always wanted to be a writer. I came to want to be a writer. And then, like, early on, it's like you might really want to be a musician, but no one wants to pay you to be a musician.

so you should find what is adjacent to being a musician that you can get paid to do. Which was marketing in your case? In my case, yeah, it was like, okay, so I was Robert's research assistant, and then I started working as a marketer for different authors. So I was like in the world, like in that world meeting people, learning things, like figuring it out sort of in the scene before I ever was writing anything myself. Well, and you're being, in my opinion, being super humble, which I'm not surprised. about, but you were not just in and around that world. You were the CMO of American Apparel, which everybody this generation remembers. Can you tell us a little bit about that and what that experience is like? How did you even end up there? And how did you even get involved in that?

It was another random thing because, so I was working for Robert and I was sort of his protege. And he was on the board of directors of American Apparel. So he was like, hey, you should hire this kid. Like he knows some things. And so I started a really low-level, position there. I didn't have a job title. I didn't even have an office. And I just sort of, they were like, figure it out, you know, figure out a role for yourself here. And I sort of worked my way up. And then there was a sort of a marketing disaster. And I ended up sort of building a new marketing department inside the company, which I then took over. So it's the same thing. It's like, I knew that I wanted to be around. Like when I, when I met Dove, who was the owner of American

Apparel at the time, you know, he was like, he wasn't like, hey, I'd like you to be the director of marketing, but it was like, I knew that if I was adjacent to it, there might be an opportunity. So I think a lot of people want, like, people are like, you know, I want to, I want to be like an influencer, I want to be a writer, I want to make videos. And they think, like, someone's going to, like, hand them this thing. And, or they quit and they expect that, they quit whatever they're doing and expect to be magically like anointed that thing. Or inspired. Yeah.

You know what? This isn't interesting. I wasn't even going to ask this question, but we were just talking about at breakfast with young people in general and there's people we have experiences. And this is not to throw anybody on the bus, but just analyzing. Like there's been so many times in both our lives when you either, you're working at something or you're getting a new job or you're starting a new company. And the issues that we're running to is a lot of young people, they get hired for something

or they get involved in a job and they say, this is what I want to do. But inevitably with any of those jobs, other tax, menial tasks that they may not want to do come along and they kind of say well I don't that's not what I want to do so I'm just going to throw that aside I'm going to do a really good job at what I want to do but I'm not going to do this stuff and I always try to explain to you and like listen there's so many things that happen in Lauren and I's life and I'm assuming yours where there's like a million tasks that I don't want to do and don't want to be involved but you just you have to get uncomfortable to get comfortable and I don't think I think a lot of people are understanding like in anything

you're doing there's going to be tasks that suck like that you don't that you don't get fired up on it just comes with the territory Yeah, of course. And in a weird way, that's actually where the biggest opportunity is, in my opinion, because everyone is pretty good at the stuff they like doing. If you can be the person that can do or excel at the things the other people don't like doing, that's a real opportunity. In Egos Anatomy, which is one of my books, I talk about Bill Belichick breaks into professional football as a film analyst. because at that time, I think he got a job working for free for what was then the Baltimore Colts, but nobody in football liked breaking down film.

It was much harder than it is now. It wasn't seen as this competitive edge or advantage. And so he was like, look, all do it. And all break down the film, all come up with the insights that the coaches and players can use at game time. They're not going to be like, oh, Bill found this. They're going to steal credit for the things that I found. but in time they're going to come to be very dependent on me.

You know what I mean? And in a way with Robert, it was like I started doing little things and then a slightly bigger thing would come up and he'd be like, well, I could do this myself or I could see if Ryan could figure it out. I think what you said about dependency,

like that you just kind of nailed it on the head. Someone becomes dependent on you because you're doing things that other people don't want to do. I'm constantly finding angles as well. And they're important. Yeah. Yeah.

Okay, so I'm going to kind of switch gears here. Okay. Can you tell us about a dark or tough period in your life that you experienced and how did you come out of it? What did you learn? Well, so when I dropped out, in retrospect it seems like it went very well. So I dropped out to work for this talent agent also. So I was working for Robert, but also this talent agent. And so he was like, look, take a week to go get your, you know, move out of college, like get an apartment.

Like, you'll start on Monday. that Sunday he checked into rehab. So the person that I quit school to work for that I had convinced my parents was like this huge opportunity that they didn't even believe me on. You know, he checks in, so I show up. The person that I was replacing had not been fired. None of the other people who worked there had been informed that I'd been hired. And he's in rehab. And he's in rehab.

So it was unreachable for 30 days. and then I've moved to a new city. I'm supposed to be doing all this stuff. And then this is a, I don't know if I've talked about this, but so when I'd met Robert and he decided to hire me, he was like, give me your phone number and I'll call you and won't get started. And so that was supposed to happen around the same time. Well, I just got a new phone and like a new phone number and I gave him the wrong

phone number. Like I didn't know my own phone number well enough. Like I made a mistake and I gave him the wrong number. and so he was calling me frantically, you know, and I wasn't answering. So he thought I was like blowing him off. So this like, you know, what could have been this, what I thought was going to be this exciting, awesome thing turns into a complete shit show almost immediately. I almost lose both jobs that I just left college for. Mom and dad are pissed.

Well, they're not even talking. So I can't even like, I can't even like, dad, you'll never believe what happened. It was like, I can't even admit how horribly this. going or they'll just say I told you so um so it was a complete you know it was a complete disaster uh in every possible like uh it was scary enough had it gone well and this was just terrifying and you probably didn't have a lot of people to relate to because i feel like you're young you dropped out of college like how is that yeah i mean i'm 20 years old so i don't have anyone to talk to about it the only person that i had was my then-girlfriend now wife and so it's it is interesting to me and

you guys are an example of this, but like, you know, I meet like lots of entrepreneurs or people who are really ambitious and they're like, I can't be in a relationship. I can't afford to be like tied down or I don't have time for it. Like I see very clearly when I look back on my life that like if I hadn't had this person who's like, it's going to be okay. You're going to be fine. Like, you know, who was there for me? I think I might have just gone back to school. Do you know what I mean? Like it could have. It's a teammate. Yeah. It's someone who's like in it with you. In a different way, though, too, because, like, you know, if you and I partnered on a business, like, we're partners, and hopefully it goes very well, and hopefully we enjoy each other's

company and all that and trust each other. But when you're, at least in this situation, if Lauren and I are married, like, it's a different, you know, it's a different partnership. Like, you're on the same team working towards the same goal and, like, not even talking income, but, like, goes to the same spot and you're, you know, as you're building a family and, like, you wouldn't tell your business partner, like, I'm scared. I think I've made it made a huge mistake, right? He's going to lose faith in you.

Yeah, exactly. there's no need for like pretense or any of that sort of posturing and so yeah it was it i mean it ended up working out obviously but uh it was it and that's why one of the things i tell people is like you can't just like jump off this cliff and and not have a plan or a support system or uh a fallback because it all the things that can go wrong can go wrong and sometimes they will and and how are you going to come out of the other side of that. You say when you write a book you put like you're all into it. How does that affect the relationships around you? Are they able to just kind of wait on the sidelines and be your cheerleader? So when I remember when I sold, it was either my second or

my third book, and they were all in very short relation to each other. My editor sent an email to, she sent an email to me. She was like, congratulations, you know, like the deal is signed or whatever. And then she sent an email to my wife that she said, I'm so sorry. Because it was like, you know, you're always thinking, okay, like at the end of this project, it'll go back to normal or we'll take a break. But it never does. It never does. I mean, the room we're sitting in right now is basically, this is what, Lauren, this is like basically my dream room. So you just, you could put me in here for a month.

I wouldn't bother you. Give me some like a bowl of food. I'm fucked. I'm fucked. I'm fucked. This is like a bowl of food and water. We're in a room with like, I don't know how many books here. I consider myself a reader.

I don't know how pretty like, like, voracious, right? I like to read a lot for my sanity. You know, I at least have to read one to two hours a day every day as much as I can. But you're putting me to shame here right now. This is a lot. Well, this is my job. So, like, I mean, like this whole shelf in the middle. So it was arranged, but whenever I do the bookshelves, I never think about, like, where the new books are going to go.

You know, like, I'm like, I'm filling all the ones I have. But so, like, that middle shelf is basically, I think that was all the books for ego is the enemy. So, like, it's somewhat unfair to compare to, like, a person who's doing it purely out of enjoyment. It's like, if you went to a baseball player's house, you're like, oh, you have a lot of baseball bats or, like, you have a lot of guitars. It's like, this is my job. How much research goes into writing one book? Because to me, this is, like, crazy. I mean, a couple hundred books, probably.

And then papers and articles and all sorts of other things. A lot. That's a lot. So just talking about reading in general, have you always been a big reader? And how is reading affected your life outside of, you know, it helps you write your books and it gives you a well-rounded base of knowledge and all the obvious? What are the maybe not so obvious reasons in how reading is like attributed to your life or helped you or helped you progress in your career? Yeah.

I mean, I think it's all based on it. I don't think I would be sitting here if it wasn't for books. I mean, it's given me a huge competitive edge. I mean, if you think about it, it's like the smartest people in history have been, writing books, describing what they went through, what they've learned, mistakes that they've made. And so I've always felt like, well, instead of learning those things, like, in my own experiences, I'd rather learn and then build experiences on top of that. So, yeah, I've always tried to read as much as I humanly can. And I think, like, the reason that my job with Robert worked out

is that I'd read all his books and they'd sent me down this route. Like, I was trying, I so loved his writing that I was trying to like reverse engineer it before I even met him. And then so when he was like, I need someone who can do that. I was like, well, I've taught myself that already. Like, please give me a shot, you know. But to go to your question, it's a, there's an introversion in writing and a loneliness to it. And it does put a strain on relationships. But I think you've got to, like, I don't think if my wife was a writer, I don't think it would work out. Like, I don't know if there's, some every relationship is different but I would think it would be hard for there to be like two of me in a relationship so we're we're very different and then so we work together in that sense

and like I'm very cerebral and she's very intuitive so I think we're one of those couples where opposites work really well together it also causes conflict obviously but I think you need you need someone like that although I'm really actually impressed by people who do it on their own because I'm like not sure how where that strength comes from totally having a teammate is so important it's been super important Michael's kind of behind the scenes in my business but I definitely think it's propelled me forward to um continue to try to be successful yeah so I kind of want to talk about American apparel I know we talked about this but I want to talk about the PR stunts sure because I really want my audience to hear like the depth

okay I think I read I'll give you I think she's triggered on this because I either read something or heard something that you did when you were working with Tucker Max I don't know if a lot of you know Tucker Max might be a little bit ahead of time but yeah I want to hear about that kind of stuff what was it called they I hope they served bare in hell it was a huge and I read a story or heard a story that you actually you know there was a huge uproar around him and you had posters printed and then you actually vandalized the posters yeah so so the book was a big success just by word of mouth alone. It's a great book. And I have it. I have some up there. And then they turned it into a movie, and it was like an independent movie. The movie's not great, but the marketing was great. And we had a very small marketing budget. And so the book had always been controversial, so we sort of thought, well, could we lean

into the controversy? The thing was like, how do you get young men to go see a movie? I thought one of the ways would be like, what if you told them that they shouldn't be allowed to see the movie? And so we created like a boycott around it. And so it started with protests, and then it was like a big thing online. And then we'd add enough budget to buy ads, I think,

in like three major cities. And one of the cities was in Los Angeles. And so I thought, what if we go and we vandalize the billboards? Because the billboards had been designed to be provocative and people were talking about it online, but I thought, what if I like, what if we like graffiti over the billboards?

Like we start like a thing about people doing that. And you did this prior to putting them up or you guys actually went up? No, no, like, I'm just trying to picture it. We bought them through a company. So they go up. And then I was like, okay, I asked the ad agency like, okay, where are they? And they're like, it's, it was like Olympic and, Olympic in Los Angeles. Yeah.

And then, so we drove there and then we vandalized the billboard. then I took pictures of it, and then I leaked those pictures to Curbed L.A., which is a big L.A. blog. And then they ran it, and then I emailed it to some other websites. And then the next thing I know there was a big piece in New York, in the Village Voice, that a bunch of feminists had started doing it in New York. So, like, they thought that it was this sort of organic uprising against the movie, but I'd started it. And inevitably, it brings more press to the movie. Yeah, it got all sorts of attention.

And you didn't have to hire a piece. agent right no no exactly amazing um yeah it was what book told you to do this no and it was we were just uh you know what's the craziest thing that you could do that you wouldn't you're not supposed to do and like what's the what's the worst that could happen nobody cares basically is what the worst that could happen so um yeah i did all sorts of crazy stuff like that okay so american apparel though i feel like you did stuff like this at american apparel too that i need to hear about yeah i mean I think it was actually part of some of the stuff that we'd done in American Parole had inspired the idea of the billboards because we were finding that we were making these really provocative billboards that people really were vandalizing. They really were getting upset by.

And then we realized, so there was this street artist who was like there was all this press about how he was like putting up these fake or sorry, he was putting up these like spoof ads all over. New York City about American Apparel. Like American Apparel ads were already controversial, and these were like way more controversial. And so they would get tons of attention because it's like, is it real? Did they actually do this? Where is this? And this went on for like a year. And then the crazy, I remember the crazy thing was then we found out that actually none of them were real.

Like he was just photoshopping them onto buildings and then taking pictures of them. And then leaking this Photoshop. thing two different blogs and then no blog was ever like well let's go down to you know like housed in an orchard and see if it actually exists right um so i was like oh there's all this media tension but if it's and if it's interesting enough people will run it without checking so um we started like we would make these controversial ads and then we would just post them on the website and then people would be talking about you know american apparel's newest campaign and it's like it wasn't a campaign Like, we'd spent zero dollars.

Like, other than making the ad, it was not in any magazines or on television or on any billboards. It was just, like, hypothetically, that that was still enough to get attention. So we were just, we were always sort of looking to poke, to do the things that a bigger company would, the gap would never run a fake ad, you know, but American Apparel was small enough and sort of, I guess, crazy enough to do stuff like that. That's nuts. And you didn't pay Kanye to say anything in the song, right? Yes, right, right.

No, and when you start to get, it's like if you get all that attention, it starts to ripple through culturally for other reasons. Right. So yeah, Kanye West talks about it in that one song. And it was, yeah, it was cool. We were just, we were like the company that everyone was always talking about. And that wasn't an accident. Do you know what I mean?

I love it. And our advertising budget was like, in a, a good year like $10 million, not $100 million like it would be for a much bigger company. So how do you go from American Apparel to writing books or are you already writing your book while you're at American Apparel? Well, I guess this is a good time to ask is the way that I discovered you. Okay. So I have a background of marketing mostly for small businesses on the side if I'm not running

one of my companies. And I was just curious of learning more about marketing. So I picked up growth hacker marketing. Yeah. And at the time, I didn't know anything about you. I just saw the book. That was life-changing. I was like, okay, cool, I'll read this.

And from there, then I, you know, when your other work came out, I was like, I like, I like this author. I'm going to keep reading them. But how much, one, let's talk about growth hacking. And two, how much further after American Apparel did you write that book? So my first book was called Trust Me, I'm Lying, which was sort of like an expose of all these different marketing things. Because my thinking was like, this is all really fun and they're cool stories to tell.

But it's not all fun in games. Like, you could do the same. playbook to become president or you could do the same playbook to spread hate or to any other sort of negative more damaging message and plus like it's also like it's fun as a marketer to make a fake advertising campaign that people talk about but if you sort of step back there is something wrong about that it's like people are getting upset and they're outraged about this thing and they're spending like real energy on it but it doesn't exist and And so it's not that I felt bad about it, but I just didn't like, I didn't like that that was the situation.

Like, as much as I was taking advantage of it, I would have rather that none of it existed. So that was my first book. And so I wrote that while I was at American Apparel because the company, as much as it got good publicity, it was also the recipient of all sorts of bad publicity for a lot of, oftentimes by the same outlet. So it's like the same outlet that was running a real story about a fake ad is then also reporting on some lawsuit or, on the stock price. And so it always struck me as sort of weird that it's like, okay, in the one hand,

they obviously have very low standards and they'll write about things that they haven't verified. But then they talk about these serious things and we're supposed to take them seriously. So I wrote that book with sort of the support of the CEO. He was into the idea. And then Growth Hacker came out while I was still there.

I'd sort of left to write books, but I was still like an advisor to the company. So growth hacker started as a really short book. I mean, it started as a 10,000 word ebook, and then it became a paperback. And then I wrote one more book while I was there, which is the obstacles the way. So I was still, I would, I lived in New Orleans and I would come back to Los Angeles, maybe like once a month and just sort of review business and work on stuff for them. But I was, the transition wasn't as abrupt as, say, like, leaving college. It was much more gradual and there was a lot of overlap between the two.

Can you explain to anyone who's listening what growth hacking is? So growth hacking is a style of marketing. I pioneered mostly by startups. It's sort of what do you do when you have zero budget when you're starting from nothing and you're not going to do like the traditional marketing stuff, right? You're not like, oh, let's print up some T-shirts or let's hand out some flyers or let's buy a television commercial because you can't do any of that. So it's like, how does Facebook go from zero users to a billion users?

Or how does Groupon become one of the fastest growing companies of all time? Or like, it is interesting to think it's like, we all remember when Uber didn't exist. Like that was not that long ago. It was like seven years ago. Uber didn't exist. And then what made you take your first Uber ride, right? It wasn't like you saw an ad for them in a magazine. It wasn't like you were watching the super.

when you saw an Uber commercial. It was just, it just sort of happened, you know, and that's, that kind of growth is what growth hacking is about. How did you, how do you, like, the first time you used Airbnb, like, how did that happen? Why did that happen? So if there's an influencer listening, how could you tell them they're just starting out, how can they growth hack between all the different platforms? Very minimal budget, just getting going. Yeah, I mean, I think the first thing that growth hackers look at it's like is this actually new and better and worth investing it like so much of what people the reason that most traditional advertising is boring is because it's two boring companies competing for the same user right and so it's like if you're trying to social media and this sort of online stuff it's all

about standing out so it's like what uh i have a book where is it blue ocean strategy it's right there it's one of my favorite books oh michael's gonna buy it uh they're saying and there's a good sequel that just came out actually. But they're saying it's like a red ocean is where there's lots of competition. You want to go to blue ocean where there's like no competition. You want to create a new market. So like there's not 50 other of you on actually there's a bunch of other people just like you on on social media now. But when you did it, you weren't like battling it out with all these other people. And so there was it's it's not like there were 50 ride sharing apps when Uber came out. They invented the category. And so as a marketer, or if you're trying, you're like, how can I, how can I

break through? It's like, actually, you shouldn't be trying to break through. You should be trying to break new ground entirely. So honing down on the niche and riding the niche. Yeah, what, what is the niche? What, what makes you so good that people are going to do a lot of your marketing for you? Like, the first time you try Airbnb, you're like, oh, this is so cool. We're going to stay in someone's hat. You know, like, you're not like, it's not like you're staying in a holiday inn versus a Marriott, and you're like, it's basically just a hotel. You know what I mean? It's so radically different and new. And so that's like, when I look at all my marketing successes, I would say the product itself was responsible for a huge percentage of whatever I was able to do.

And people always go like, yeah, yeah, I got that. My thing's really special and new. But the truth is it's not. How did you get so good at marketing? Like, is it just something that's come naturally to you? I mean, I think I got to work with really cool clients. I got to work with people who were already pretty good at marketing. And then I think I didn't learn like the old way of doing it.

So it was just like, okay, Ryan, make this ad. Yeah. And then it was like I didn't know how. So I made up a, I was just trying to do it from a totally different perspective. That's the biggest thing. I mean, being in marketing myself, like the thing that I try not to look for is if somebody comes out of school and they says, oh, I studied marketing in school. To me, and I don't want to put anyone down, but that's kind of a red flag because you're learning

things that used to be. Yes. But the problem is that the landscape's shifting so frequently at such a fast pace that you kind of have to be a practitioner. You have to kind of be out on your own. I'd much rather hear from someone go, like, you know, I studied English and I built this blog or, you know, I help my friends start this YouTube channel. or like I did all the marketing for my dad's coffee shop.

Like I would rather you have done something or made something because then you're actually like, then you actually know what the feeling is to like start with nothing and try to get one person to try something. I also think studying history. Sure, sure, sure. I think the theme of my childhood was figuring it out. Yeah. And I always say that's like the best tool in my toolbox now because I've had to just kind of figure everything. out. It sounds like that's the same for you. Yes. Elon Musk talks about this idea of going to

first principles. Do you guys know what this means? So basically it means like, so when he's starting SpaceX, there were lots of companies that like, he wants to have a rocket company. So you would go to these people who make all these different pieces of the rockets and you go like, okay, we're going to buy this from this supplier and this from this supplier and then we assemble it. And the prices were like insane, like totally unaffordable. So he's like, well, what are these things actually cost to make? And they were much, much cheaper. So he's like, oh, instead of doing it the way that everyone's going to do it, I'm just going to figure out how to do it myself. And it turns out he's able to build this company because he doesn't go, okay, the way you start a space company is by doing

X, Y, and Z. He said, let's look at this as if there was no precedent. What do all these individual pieces cost? That's how we're going to do it. And so they end up making all their pieces for the Rockets or for the most part. And so it's this idea of not, like, when you study marketing in school, they're like, here's what marketing is. They're not saying, here, you're taking over this app, make it grow. And then you're having to figure it out and sort of go to the essence of what it means to spread something.

Did you write about that example in Obstacles Away now? Is that? I might have. Or did you write about that somewhere else? I think I, now that I hear you saying it again, I think I've read that. I might have written about it somewhere, but I mean, I just think about it all the time. It's like, make sure that you're not just internalizing, like, the way we've always done things or, like, the way it's supposed to be done. Because really, marketing is anything, as my definition in growth hacker, is like, anything that gets or keeps customers.

So if, like, Zappos, like, has amazing customer service and they've, like, hugely invested in customer service. but the reason I use Zappos is because they have good customer service. So their customer service is actually marketing. Do you know what I mean? Or if I was using Zappos because they had the best prices, and then the shoes that I got, they didn't, they sucked or they were broken or something. And then so I was not going to be a Zappos customer anymore. But I email them and they're like, we're so sorry.

Here, we're going to do all this stuff for you. And then I stay a Zappos customer. That's marketing also because they did something. that kept me accustomed. So it's really, it's just, when you go to first principles, you're just like, okay, here's what this actually means, rather than like, here's the definition of what marketing is supposed to be.

And I think this is true for everything. It's like, you know, an influencer today means that you're on social media or you do this stuff. But really, you could have an influencer who's not on the internet at all. They're just like some guy in your town that everyone listens to or whatever, right? It's like, what does this actually mean?

That's really important. Someone drove by me. the other day this guy in this cool hat and he was driving a jeep and he was listening to johnny cash and i looking at guys what and i was i immediately went and downloaded um johnny cash after that and i said to i said to michael i said that's an influencer yeah yeah yeah he's just driving by right doesn't necessarily just have to be on social media totally okay so i want to talk about the clients that you work with in marketing because you work with some huge names yeah tim ferris i did i did i did it with tim ferris last night that's amazing yeah he's so cool he's the best yeah we love it

his podcast. I mean, it's, yeah, it's like one of the biggest ones in the world now. So how do you work with all of these people? Do they come to you? Do you approach them? Like, what's the process? So I met Tim in Austin in 2007 before his first book came out. So he was, he was doing the influencer thing before anyone else. Let's say his book had like a $10,000 marketing budget. And this is what I love. This is exactly what we're talking about. Let's say his book has a $10,000 marketing budget. Instead of buying $10,000 worth of ads or, you know, sending out $10,000 worth of review copies, he bought $10,000 worth of plane tickets, and he flew around the country to every tech conference, and he just met as many people as he could, and they all became his friends, and then it

just happened that some of those people went on to found Twitter and Uber and made him literally millions and millions of dollars because he invested in their companies. But he said, like, if meeting these bloggers helps sell my book, then it's marketing. And that's what I'm going to do. And so that's what he did. And I was just one of the people that he met and we became friends. And I gave him some advice on that book. And then I did a little bit of marketing on the next book. And then I did all the marketing on the next book. And then the next one. And then hopefully I'll work on this one that's coming out soon. That's really cool. And then most of my clients come because they either heard that I worked with someone like him or someone like him knows other people like him and goes, you have to

work with this guy. The domino effect. Yeah, I would say like 85% of my clients come from referral and then other ones come from, which is still basically a referral, comes from media attention that I've gotten for those campaigns that I've done for those people. I can imagine now the books help as well. My books? Yeah, totally, totally. It's almost like content marketing for the client. It's like a resume and book format almost. Yeah, I mean, like that's another thing. It's like people like how do I get more clients it's like do things that people like and you'll have more clients than you know what to do with in basically any field and um you know it's like you found out about me from one of my marketing books but other people read my more philosophical books and then find out that like

oh he also does marketing so um yeah I was the other way yeah yeah yeah and so it i think it's about building a brand or a reputation that then you can monetize you can monetize you know in many different ways. So let's switch gears a little bit here and talk about the philosophical books. Okay. Like I said, I found, I discovered the obstacles the way through growth hacker marketing.

Yeah. And I have to thank you because I think when I was 14, 15 years old, I read meditations. Really? Yeah. My dad was always a big reader and he gave me a lot of crazy books growing up. And I think that, you know, I've been reading from a young age. Yeah, really lucky. He just, that's one thing.

He's like, you can do this. You can go screw off here. You can go mess around. But you have to read. And when I was a kid, if he would give me, we'd have like an allowance or have to do chores. But the one thing that he spared no expense is like anytime you want to Barnes and Noble and I'll buy you any books that you want. And anything you can read, which was, which was cool.

And I don't think I thought about it until actually just now how lucky I was for that because I could literally go into a bookstore and he would just say any book you want. But it would have been cheaper for him to buy you like a Nintendo 64 and it would have changed your life. It would have been cheaper because you would have been addicted to it. but you wouldn't have opened up all these doors. Like I remember having to do chores and mow the grass and all these things to save up for like one video game. Yeah, but you could have unlimited books. But unlimited books. And so I guess, you know, a lot of the time while I was saving up to play video games, I would read a lot of books, which is good.

But going back, when I read Meditations at the time, it was, it's a difficult book to get through as a 14, 15 year old kid. And I kind of got through it, but I don't think I took everything away from it, right? It just didn't have enough life experience at the time. So when you came out with obstacle, it really kind of refreshed my view on stoicism. And since then, I've gone back. But for people that don't know and talking about stoicism, how would you define it? I kind of define it. And the reason I like it is I think it's philosophy, which a lot of the time kind of turns people off.

But I think it's one of the most logical. It's a practical philosophy, right? So most people think philosophy is like what university professional. like waste time just sort of talking about hypothetically and stoicism is much more a practical system for living. Do you know what I mean? Like in some ways it's almost closer to a religion in the sense that it's like do this, don't do this, this is wrong, this is right. It's not saying like if you don't go these things, you'll go to hell, but it's saying like these things make you miserable and these things make you happy. Here's some bad assumptions that human beings have. Here's

some better assumptions. You know what I mean? It's like a, it's a way, this philosophy was really supposed to be like the guide to what they were called a good life. So it's like, how do you be happy? How do you feel not stressed? How do you, how are you in control of yourself? How do you do good things? And that's what stoicism really is. My sort of definition is let, and by the way, most people are familiar with it. They don't know. It's like the movie gladiators about stoicism, Marcus Aurelius, the emperor of Rome that common is. Maybe we could give a little. context of the history of stoicism. Yeah.

So if you've seen the movie Gladiator, Mark Cyrillius is the emperor. He's the old guy. Joaquin Phoenix's character who kills him, that's his horrible son. And that actually did have, his son didn't kill him, but he did have a shitty son. But it's basically, it started in ancient Greece. It comes to ancient Rome. It's typically for like doers, right? So on the one hand, you have Marcus Aurelius.

It's crazy to think, like, you have the most, you have the king. of the world, essentially, who really just loves philosophy, like he loves reading books and trying to make himself better. And then the person that he's basically exposed to Stoicism through is a man named Epictetus, who was a slave. So you have this philosophy that on the one hand is for, like, extreme adversity and difficulty and slavery. And then the other, it's like this way of coping with extreme success that is, like, being the emperor. Um, So my sort of definition of stoicism is basically that the stoic believes that we don't control what happens around us. We just control how we respond.

And that's really at its very core what the philosophy is. It's just like the only thing that I'm going to focus on is my response to the world around me. So I don't control if someone's an asshole. I don't control if a hurricane knocks over my house. I don't control if I get cancer tomorrow. but I don't control if someone insults me, right? But I do control, do I tell myself that I've been hurt, you know, do I sit there sort of weeping over my house or do I start rebuilding? You know, I've got cancer, like, how am I going to live the rest of my life, right?

Whether it's six months or six years. And so stoicism is really, what I love about is this sort of empowering kind of self-reliant way of living. I think when I revisited it, it just makes so much sense to me because, like you said, the way I read it and the way I understand it is like really the only thing you control in this world ever is your thoughts. Not your wife, not your family, not outside events, not not politics, not who's president, who's not for the. And none of that stuff. Really, the only thing you really control is your perceptions and your thoughts. Yeah. In a weird way, you don't even control like your own body, right?

Like in the sense that like something could happen to it, right? you only control your own thoughts. And so really practically, like as a writer, I control the idea for my books. I control the effort that I put into the books. I control how hard I'm going to work on them. I control the marketing plan. But I don't control how many copies they sell. I don't control if everyone says that they love it or they hate it.

And by the way, if it sells a million copies or if it sells one copy or if everyone says it's a work of genius or that's a piece of shit, none of that should change my thoughts of what it is. It's like I should know that it's the best that I'm capable of and therefore I should be proud of it. Or I should know, you know, I got lazy halfway through and I didn't do my best job. And so the fact that it's selling really well shouldn't make me feel any better. I should, you know what I'm saying? Like that actually they're saying external things don't have power over our thoughts. only we do. And so by controlling those thoughts, we have an advantage over other people who are

sort of like jerked around by their thoughts and by what other people do all the time. So speaking on that, let's kind of talk about the Stoics response to stress or unexpected events. Let's say someone's going through something tough, terrible or something that they perceive to be terrible. What would be your first piece of advice? Well, the Stoics would back up and go, why did you think this wasn't going to happen? right like like why were you not prepared for this to happen and that's really true it's like we spend all our time thinking about how things can go well and how how exactly how we want them to go and then we're like caught off guard when they don't and that's really uh not a great way so the stoics are like always thinking about the worst case in error they're prepared they practice for things to go wrong um but when you're in that stress you're going let's let's try to look at it objectively like why is this stressful. It's probably because you have these assumptions about how you need it to go or what you're what you feel obligated to do, um, that you feel like everyone's counting on you, that if you mess up, everything will be

lost. And the stoic would sort of ask you to step by step, like, go through each one of those assumptions and go like, is this actually true? Like does anyone care? Or you making yourself, are you making this a stressful situation? And then I, I think they would go, you know, um, all that being said, I'm going to proceed anyway. I'm going to do my best. It's not just like, oh, I'm going to think my way out of having to do any work here. But it's just like, let's make sure I get this under control. And then I'm going to do my best. They wouldn't let a stressful situation shut them down. Yeah, of course, because first off, it's not as stressful as you think. And second, it's not an excuse, even if it is. Michael loved that book. He has notes on every single page.

Oh man, that's very cool. I did love it. It was good. And like I said, it reinvigorated my interest in going back and actually reading the stoic work. That's what I wanted to happen. That was my dream. Okay, let's talk about raw nerves. So you have said we are a pile of raw nerves.

It's almost like we're always waiting for something to rattle us. What are some tools that you use when you feel super rattled? I mean, really practically, like when I start to get really rattled, I like I like to exercise so I'll like run or swim I'm just sort of I want to step away from this entirely because it's like almost the more you're focused on it the more you're throwing yourself at it

the more stressful it's going to be and then I mean I'm going through something right now so like we have this place and we have a farm and both got damaged in the storm so it's like I got some things I have to have fixing the garage and the roof at our farm is messed up and then there's this problem and that problem and it's like

when I'm looking at it all at once, it's like, this is going to be so much work. This is so unfair. Why can't someone just handle this for me? And that's like the worst way to look at it. The better way would go, like, okay, I'm going to put all of these in a list. I'm just going to do one right after another.

It's like if I try to solve them all magically at one time, I'm probably going to solve none of them. And if I do it piece by piece, I'll start to make process. make progress. Yes. Yes. Exactly.

Right. Why am I believing this is still stressful? Well, it's just, I think when you, I think the problem is people, like, they have a difficult time, like you said, prioritizing. So all these different things swim around in their head and they get so overwhelmed because you can't take, you can't take a step back and say, okay, holy shit. Like, let me just take one of these one by one. Yes.

And then, you know, is this one solvable? Yes. And if it's not, then like move on and focus on something else. Right, right. Why are you throwing their? yourself at the hardest one over and over again when there's 10 other easier ones that you could get momentum and then breeze through the harder one that kind of goes into building a lasting brand though it's like you you almost like you you wrote about this you have to launch kind of quick

and then kind of learn as you go yes instead of trying to think of the whole thing at once yeah well it's like people like I want a million followers and it's like well you have seven so why don't you just try to get to 10 first you know if I told you how many times it's it conversation. People are like, when did you have an epiphany? I'm like, there's been no epiphany. It's like slow, like you're chipping away slowly. Well, so my, my books are probably at the, by the end of this year, we'll have sold about a million copies across. Incredible. And that's like something I've been, thank you. I mean, that's been something I've been working on for a long time. But it's like the most copies I've ever sold in a single week of all,

of any one of the books is like, I guess 10,000 would be one for ego. And that's like, that's, higher than any of others, but like on a normal week that wasn't a launch, probably 5,000. That's so many. But it's really not. Like not compared to a million, it's not. Come here to a million. And so it's like people look at where people are and they go like, how do I get there? And it's like, no, you should look at where that person was where you aren't.

I have to think about this with my own books in the sense of like, let's say I'm working on a book right now and I'm halfway. through. I can't be comparing it to where my last book ended up. I have to be comparing it to where I was halfway through my last book. And if I do that, I'll actually, if I go, oh, I'm actually ahead of where I was at that. This halfway point is better than the last halfway point. Then I feel confident. If I go, this halfway point is not as good as the completion point as the finish line at the last one. I feel bad. And so this stoicism is all about those sort of mind tricks going, oh, I was just thinking about it wrong and thus creating this stress and anxiety or doubt. And if I think about it a different way, I don't feel that. So I'm going to go with the different way. I mean, in social media, it's hard

to not compare yourself to everyone else. It's hard to just start and stay in your own lane. How do you think that you've been able to stay in your own lane and not focus on what everyone else is doing? Well, so I think social media is really important as a creator. I think as a human being, you should spend as little time on it as humanly possible. It's like, like, when I look at my Instagram post, I have to go like, this is not my life. These are like the best parts of my life. And that, you know, the seven days between those two photos, a lot of boring shit happened and a lot of normal shit happened. You were fixing your roof.

Yeah. Yeah, right. Maybe I should start an Instagram account that just shows me like really shitty and really boring parts of my life. And it would have like zero followers because who would want to watch that, right? me sitting for three hours reading a book yeah yeah and so so it's like you've got it's like you've got to it's like you've got to remember like where you're performing and then go like oh wait everyone else is performing and that you can't buy into that it's like even with your own brand like I think marketing is obviously essential but you it's it's like you got to have this weird relationship with marketing as a

creator where it's like on the one hand as a salesperson you sell the shit out of what you're doing but then as the owner you're like almost miserable all the time about how much better everything could be do you know what I mean it's about I know what you're saying it's kind of a finesse too

between the two yeah like if you're going around going like I'm the best I'm killing it and you're actually thinking that you're going to get worse but if your if your marketing is making it look like you're killing it but you're going around going I have to improve this

I have to improve that then you will improve totally I want to talk about a little bit about living in the moment. There's a, there's a quote that I keep on the back of my computer that I love, because I think probably my favorite Stoic is Seneca, and then you're like Marcus Reilly, but says two elements must therefore be rooted out once and for all, the fear of future suffering and the recollection of past suffering, since the latter no longer concerns me, and the former concerns me not yet. Through, thinking of Stoic philosophy, how would the Stoics consider living in the moment,

and how would they prioritize, you know, past, present, future? Well, they would say the past is unchangeable because it's done, and the future. future is out of your control or it's not up to you. And it's, by the way, it might not even happen, like, because you could die. So they go, like, this present moment is basically all you have. And they don't literally mean, like, this moment. They just mean, like, some interminable number of minutes or hours or, you know, right now. Like, because that's all that you have.

I have a quote from Santa Claus on my desk that I love that's sort of about the present moment where he says, some lack the fickleness to live as they wish and instead live just as they have begun, which is another way of saying, like, people go, well, this is who I am and this is what I'm doing, so I have to continue to be this. Whereas, like, if you're living in the present moment, you can change your mind or change course at any time. It's like, if you're obsessed with where you've been or where you're going, what you're not doing is thinking in the moment about where you actually want to be and what you actually want and like.

And so I think there's incredible power in living in the present moment. And what is the consideration to future? Well, I think you always want to be putting yourself in a position that you're set up for the future. But I don't think you want to be doing things solely for their benefits in the future. Do you know what I mean? Like it's not like, oh, you could die tomorrow. so don't save for retirement. You know, like, saving for retirement is good because you might have to retire,

but also because spending all your money now is not good. You know what I mean? Then you're just, like, addicted to pleasure and you're being reckless and irresponsible. And so, you know what I mean? So there's almost all the good things that you can do in the present, I think also set you up for a good future. I like that. Don't let your past define you.

Yeah, because it's simply, is what it is. Okay, so let's talk about failure. One of my favorite quotes from your book, Obstacle is the way, is the quote that reads, failure shows us the way by showing us what isn't the way. So let's talk about failure. Yeah.

Tell me. Let's just get it all out there. Yeah, let's get it out there. I mean, look, it fucking happens. Let's talk about really fucking up. It happens. And you're going to try things that aren't going to work out. And you could look at them as, okay, it didn't work out.

that was a huge mistake, or you could go, like, now I know that that doesn't work, you know, I eliminated one of the infinite amount of options. And so that's what I'm always, like, for instance, I'm always trying to learn what I don't like. And sometimes you have to learn what you don't like by trying things you think you're going to like, and then finding out, like, oh, wait, this is horrible. This is, you know what I mean? Like, for instance, like, finding out what your limit is as a person, in terms of like workload. If you're just guessing, maybe you're leaving a lot on the table. So maybe you have to over commit and then make a bunch of mistakes

and then go, oh, I need to slow down. I need to be more in control. So I think failure sucks and ideally you want to avoid it. But when it does happen, it does always possess some educational component. Are you hard on yourself when you fail? Yeah. I mean, I think I think I am. I think most people are, but I try to, I'm trying to not, that immediate reaction,

I'm trying not to let, like, dominate. I can't believe you're 29. I'm 30, actually, so. You're 30. That's why you can't believe it. Oh, my gosh. It's crazy. Christ.

So the next, you follow up obstacles away with ego is the enemy, and I don't want to sound like, who's that guy that does, like, the movies, you know, the, the beard? James Lipton? Yeah, James Lipton. I don't want to sound like that, dude. But the reason I think I like you, I identify with your books is you take subjects that may not be the most, like, tittle-ized and the most exciting subjects,

and you make them very accessible to, and entertaining to readers. So like I said, reading Marks, Realist Meditations, that's a difficult book for anyone that's not a big reader to get through. It's just, it's hard. Your books make it very, I don't want to say easy, but you, but applicable is a good word. Yeah, I mean, I think the reason most people don't read is because a lot of books suck, you know. And so I think my job as the writer is to make it entertaining and accessible.

And like, look, most people don't want to read a book that tells them that they're too full of themselves. So I sort of saw that as a challenge and then I thought, okay, I think we all know that ego is a problem, but we don't want to be lectured about it. So I'll lecture other people about their egos and then we can sort of see ourselves reflect in that, right? So I want to talk, I want to look at historical stories of either really successful people or really unsuccessful people whose egos held them back or by conquering their ego, they were able to achieve that success. And then we can, we all have that part of us in us. So we could learn from that. No, I think when I think back on my life, and I don't want to speak for Lauren, but most of the time when I've gotten in trouble or done something stupid, it's because of ego's gotten in the way.

Of course. And it's, one second. One second. One second. And it's, but it's, but. But it's difficult sometimes to differentiate between competence and ego. Maybe that's, is that the right way to say it? No, that's totally right. There's a quote I have in the book from one of the Stoics where he says, it's impossible to learn that, which you think you already know. I think that's a great encapsulation of ego.

So it's like we're getting in trouble when we think we've got to figure it out, when we think it's going to be easy, when we think like everything else I've done has been a huge success. And, you know, that's not confidence. Confidence is like, okay, I'm a hard. I know that I'm a hard worker, so I'm going to work really hard. So I don't have to worry about that. Or like, I know I'm stronger at, like, you think about like two boxers sizing each other up. It's like, okay, here are my weaknesses and that's humility.

Here are my strengths. That's confidence. You know, I'm confident that I'm better than them here and here, but I'm vulnerable here and here. ego is like, I'm the motherfucking champ and no one can touch me. Like that's, that might get you into the ring and might feel like it's beneficial in the short term, but it's also how you get knocked on your ass. I think Connor McGregor, honestly, maybe this is controversial, but I think going out on a limb that I think he's a good example of someone who's highly confident. Yeah. But maybe he has his ego in check.

Like every time he's taken a loss, he's been very humble about it. He said, you know, I could have done this better or I could have done this better. But going into the fight, he's for sure saying, like, listen, I'm going to beat the hell out of you. I'm going to win. But I bet privately he was much more realistic about his chance. And that's the difference between marketing and your own sort of personal assessment, too. But I think he also, I bet he's, I bet he looked at it and he was like, look, if the following things go right, if I do these. I bet he, like, if he had, he sort of, I think he knew, like, if I have to go more than five or six rounds, I'm probably not going to win.

and that's why he was trying to win the fight early, and it didn't happen, so then he lost. But I don't think he looked at that in any way and was like, this is going to be easy. He wasn't shocked by the loss. Don't you guys think, though, that he was looking at it from a marketing standpoint,

completely not if he was going to, you know? I mean, I think it's both, right? He's like, look, this is mostly upside for me. And he said this. He's like, you either win or you learn, you know? And then he's probably like, but either way you make $100 million. dollars.

And there's also no, I mean, what I always tell people too is like, people like, oh, he lost, he's done. But they said, now he has to go back to UFC and he's going to be not get paid as much. I go, no, you're not understanding. Like, he did such a good job marketing himself in that fight that no matter what he does next, there's going to be a huge audience that's interested, like, okay, what's this guy going to do next? He's on a whole other level. Yeah.

And he's going to garnish a payment bigger than anybody else in that sport. Yeah. Okay. So I feel like my ego is a constant work in progress. It's something I feel like I need to check myself on daily. Yeah. That's just the truth. In the world of social media, the ego is so real.

What's a tip that you can give me and the listeners for checking our egos? Well, look, I think checking out from it as much as possible, like, you know, experiencing things in the real world, whether it's working in a soup kitchen or, you know, hiking in a national park. Like, don't live your life for social media. like let social media be a reflection of things that you do and then make sure you're going out and reminding yourself just like how much is out there do you know what I mean like one of the ways I keep mine in check is just like I'm always tackling harder and harder projects so even as things might be looking great on the outside to other people like I'm getting my ass kicked so that's helping as well you said that you like to hang out with people that are smarter than you and surround yourself

with that too that's the way to keep it in check yeah what the hell you're doing with us then Or I like to hang out with people that just like where I live most of the time like on the farm is like none of these people care at all about who I am. You know what I mean? Like I'm like the idiot who doesn't know how to hang barbed wire or something. Right. Like so I like to spend time. They don't just have to be smarter than you like so it gets to be around Nobel Prize winners. Just go around.

Just don't be in your element all the time. Having people tell you you're great, you're great, you're great. Yeah. But just like people who are better than you. at some new or different thing. It's not the most impressive thing, but I don't know how to repair. I don't know how to change the oil on a car.

So if I'm around someone who's like, what do you mean? That takes five seconds. I'm like, that checks you. You're like, oh, this is something I don't know. Didn't you spend a long time? I feel like, I don't know if I'm saying this right, but it was like a year you spent doing something on a fence.

You did something after your book. I heard you say on Gary's show. Oh, no, no. I was saying that, I mean, on the farm, it's like work all the time. And it's very humbling work that's very different than the work that comes naturally to me at this point. So, you know, like today after this, I have to go like seed several fields. And my wife's like picking up the grass seed right now. We have to like plant for the winter grass.

And so like I've never done that before. So it's going to be a comedy of errors. but at the end of it, I'll feel both humbled and confident in the sense that I've just done something I've never done before. I feel like when I'm writing or doing something creative that I have to step out of it to gain perspective, I always tell Michael I'm like, I need to wrap my head around this before I give you like an answer. Do you use the farm as something where you step out of your writing? And when you do do that, do you stop thinking about writing completely? Yeah, yeah.

I mean, like when I swim, my mind is like still, I'm thinking of nothing. And then sometimes that problem that I'm trying to solve, like the solution just like slips into your mind. Totally. Yeah. And the same way. See, now when I say I need to wrap my head around something, I'm going to refer to Ryan. You got to wrap your head around a lot of things. Like with my wife, like me running or swimming is not like a thing I do for me.

It's like it's part of the work day. Makes sense. Right? Because it's so wrapped up with me being good at what I do. So it's not like, oh, why are you? home an hour later than you were going to be home. Like, why did you go to the gym? It's like, no, work just took an hour later than normal.

Got it. So it's kind of like your meditation. Yeah. Do you meditate at all or is that your meditation? I can't sit still. Yeah, I'm the same way. I can't meditate either. I've really tried.

I've tried to read up on it. I've tried to do it. I just like, I think my form of meditation is probably reading or working out. Like, and I think that you can get formed. And I've heard a lot of people that have really big proponents of meditation. I've given it a good effort. Maybe I'll go back to it, but it's just not. Maybe at this point, it's not for me.

I try to do Tony Robbins priming. Okay. It's okay. It's better than just sitting there. You know what I mean? Yeah. Okay. So let's talk about what we're, you know, kind of what we're here to talk about, which

is perennial seller. Okay. Your most recent book, The Prennial Cellar, The Art of Making and Marketing Work that lasts. The way I understand it, perennial sellers, and correct me if I'm wrong, I think New York Times bestseller list is like, is it done by month or by week? Both. Okay. month and week, how books are selling or is there multiple?

Okay. But a perennial seller is maybe not factored in. So that would be like books like maybe Harry Potter or Catch a Mockingbird, Catching the Rye, stuff like that. Like 90% of the income in the publishing industry, also the music industry, also the movie industry is not from like what just came out. It's from the things that are 10 years old or 5 years old or even 18 months old. and I mean even my own books

like the obstacles away will sell more copies this year than it did last year than it did the year before than it did the year before but it won't go but it's never hit any of the list ever and so like when someone says I'm a bestselling author what that means is they sold the best in a seven day period not the best ever right or not the total number of copies sold

so you know I know people who have a million Twitter followers, but their tweets get seven retweets. Meanwhile, I know people have 10,000, and they do a thousand each, right? So it's like, the numbers can be very misleading. You know, I know books that have sold a million copies in 1986, and from 1987 on, they've sold zero copies, right? So it's like, ideally you want to have that lasting relevance, staying power, and that's what I've tried to do with my books. And then what I was writing about in this one is, like, that's how I wish more things were

and I wish more people set out to do stuff like that. Well, I like the book because you apply it not just to books. Yeah. I'm not a writer. Right. And for Lauren, you know,

she's a writer, but just basically creating work in the creative process. Yeah. So the first half of the book covers the creative process and what goes into that and the dedication that you need to have to actually create a quality piece of work. And then the second half is marketing,

which I think is so important, which I think a lot of creatives kind of slack on. Yeah, not just okay I made this awesome thing and now everyone will know my name you still have to hustle and work really really hard and in some ways that marketing is like another creative canvas you know i heard you talk about the difference between signfield and friends can you can you talk about that because that really put it in perspective for me well people have gotten mad to me because i guess i guess friends is popular again with like they got a big community not like signfield though that well that's my point

That's my point. And in some ways, I would wonder if, like, Friends is having a resurgence because, like, everything has gotten so much dumber that, like, Friends seems, like, smart in comparison. Do you know what I mean? Yeah. Yeah. Yeah. It's like, it's, like, compared to, like, Logan Paul, Friends is, like, a smart television show.

But, you know, Seinfeld, as a television show, has made more than $3 billion since it went off. the air because of reruns syndication Netflix is a Netflix or Hulu deal and that's because it's not it's a show it's not about New York in the 1990s it's a show about young people living in a city dealing with the absurdities of life right it's it's got friends is a drama is a dromedy Seinfeld is like Jerry Seinfeld's sort of comedic eye acted out right so they're always dealing with you know low talkers or double dipping or like they in they captured all these ridiculous parts of life that can still be applied now they're still true it's a bunch of memes almost that's exactly that's exactly and I always think back like I don't I didn't I was never a big friend family but a big Seinfeld guy there's so many episodes. episodes and quotes you can remember from Seinfeld. Like I can't I can't I don't really see that happening with friends. So why is that explain like the difference to the audience? Why? Why?

Well, so it's funny. Every episode of Friends is called like the one where like Joey does this. But it's like actually I can't really remember any episodes of friends and I've probably seen several I've seen at least 100 episodes of friends. But if I were going like have you seen the Seinfeld like the one where they're lost in the parking lot? Like I got lost at the Austin airport parking lot like two weeks ago. and I was thinking of that episode as this happened, right? Or, like, have you seen the one where Kramer gets a job, like, gets hired at a place,

but he doesn't actually work there? You know, like, they've captured all these elements of, that are hilarious in the moment, but they also capture some essential, like the one where George decides to do the opposite of everything he normally does and his life is successful. Like, we've felt like, we've failed a bunch of times and we're like, well, what if I'm really trying? Why am I feeling? What if I just did the opposite? You know, like, these are all things that we've thought about and then they actually did it on the show.

And so it's sort of got that timelessness built into it. If, like, I remember, I remember some episode of Friends where they're like, they're all going to like a counting crow's concert or something. Well, that doesn't stand up that well. Like, if you think about what happens in Seinfeld, there's. There's no celebrities. There's nothing that really dates the show. And so it feels very time. It feels both timely and timeless at the same time.

And that's something you have to build in when you're making something. Also, like, Friends is not relatable. I mean, it's absurd. Yeah. It's like it's so expensive to live in Manhattan. So I think you can relate more to Seinfeld. Absolutely. So let's talk about the creative process.

And in your opinion, what does it take to create a perennial seller? Like, what do you have to do to sit down? It takes however much work you think it takes, it's like 10x that. Do you know what I mean? Just way more than you think. And I think people don't want to do the work. People want to have, it's like people don't want to write books. They want to have books.

Like, they want to have a book that they've written. Or people don't want to build a social media following. They want to have one. And they think that they've heard stories about how so-and-so just threw up a video. and now she has 7 million subscribers. And it's like, that wasn't how it went at all. No, no. It's interesting to think about,

we were asking you earlier before we started this podcast. Has anyone asked you to do a podcast? Has anyone asked you to do a podcast? Yeah. I wanted to get your take on this. This is a little bit different. But for writing, for example, you sit down, you have an idea, you write it out,

you go through an editing process, and you write out, then you go through another editing process and on and on until you get your final product where you decide, okay, I'm happy with this, it's going out to the world. Yeah. when we started this podcast definitely wasn't like that.

And I don't think it would have been possible to do that because when we launched, we said, okay, we're just going to launch quickly and get this out there. And it wasn't so much because we wanted to half-ass it. It was more like we needed to do it to get to a place where we were both practiced because both of us don't come from anywhere near this background. Yeah.

I think every kind of content is different. And a huge percentage of my writing is not done in isolation over two years. I write articles every week, right? So different things, if you guys were making a movie, you wouldn't just put it, you wouldn't work on it in over an hour and throw it up. Do you know what I mean? So different content takes different things and you have to respect whatever the medium demands, I think. Yeah, and I think like even for this, as you see, like these questions aren't just off the top of the head. Like you have to, I think people don't put a lot of time in researching and things and they don't think.

But I guess the question I'm asking is, do you think that approach is right or wrong? Like for us, when we, the way we did it. Well, I mean, in growth hacker, I'm talking about that sort of minimum viable product. All my books start with articles that I'm testing and getting feedback on. So it's very risky and very hard to do this stuff in a vacuum and hope people like it. So I'm actually more a proponent of putting it out there in the world and getting feedback. But I'm really not going to pour the gas on the marketing side of things until like I know it's good. Oh, we got some feedback in the beginning.

It was tough. I mean, it's tough to stomach sometimes. Sure. So before we wrap this up, I want to know what book you would recommend the audience starts with because you have like a medley of books. Like what do you what's the book that you would recommend? Let's do three books that you think would enhance anyone's life. But I want to start with one of his. Like what, which book of mine?

Yes, which book of yours would you recommend? I probably start with the obstacles of the way. I was picking one for me. if I'm picking and I go with the 40 Laws of Power from Robert Green I think that's a must read my favorite novel

is what makes Sammy run by Bud Schuylberg I love that book these are like my favorite books these are like my I call them my life books so do that and then I really like

the War of Art and Turning Pro by Stephen Pressfield I love the War of Art yeah of all those books I have not yet read three of those books

I have not yet read 48 Laws of Power, which is crazy because it's been... That looks like you've read it a lot. You can tell. I have one copy, two copies, three, I have four copies. Okay. So you guys, you've got a lot of reading to do. Yeah. Okay. Where can everyone find you? Where can they can find your book? Pimp yourself out. Books. Books.

Yeah. So all the books are on Amazon. Just search my name. My website's Ryan Holiday.net. And then I think I'm at Ryan Holiday pretty much everywhere. What's the address of the farm? No, just kidding. Please don't come. Thank you so much for sitting down and taking the time with us. Yeah, this is awesome. You are a smart dude.

If you like this show, you guys will probably also love episode 48 with Mark Manson. Mark Manson is the author of The Subtle Art of Not Giving a Fuck. We interviewed Mark last year, and it's one of our favorites. Also, you can go to the Skinny Confidential and search Book Club. And there's lots of different posts. I think Michael's wrote some. I've wrote some about our favorite books. So make sure you're also subscribed and you've rated and reviewed the podcast.

If you do write a review, email it to Ask Lauren with a Y at the skinny confidential.com. And we will send you my five beauty tips and tricks straight to your inbox. As always, follow us on Instagram at the skinny confidential and at Michael Bostic. And we will see you next week.