The Skinny Confidential Him & Her Podcast - #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 Bostik 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 Bostik are bringing you along for the ride. Get ready for some major realness. Welcome to the Skinny Confidential, him and her.

Aha! Aha! What's up, everyone? Welcome back to the Skinny Confidential, him and her show. Today, we're going to be talking with Ryan Holiday, who's an author and master marketer. But first, I'm Lauren Everts, the creator of the Skinny Confidential, which is a blog, podcast, and YouTube channel. And I'm Michael Bostic. I'm an entrepreneur 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 Obstacle is 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 Lauren's blog. He recently released a new book called Perennial Seller, 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.

To name a few. So yeah, this interview is one of our longer interviews. Lauren and I have been a fan of Brian'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, like 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 both loved Austin, though. Austin's fun. Okay, so the first half of this interview really covers a lot of Ryan's background and 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 values basically root 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 peeked at what you wrote. I journal in it sometimes. I always peek at your journal. Damn it. All right, I always peek at your journal. Well, 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. 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 okay so tell me about how you started working for this author his name was robert green yeah yeah um 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

uh in the way that some people would do it with podcasts right like uh it's like oh i'm gonna do this thing and then it gives me an excuse to like reach out and meet people like 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 also worked with Robert Green. And then 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. Um, 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 around here somewhere. He was writing a book with 50 Cent. And so my first job was just transcribing the interviews. So I just transcribed hours and hours of interviews with 50 Cent. And then 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, 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 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 um you know like they'd raised my sister and i to go to college um i think they took a lot of pride in us going to college and i think 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 to who who didn't finish college um 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 I think one of the things I realized is that, you know, your parents' 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 parents' 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, it's too conservative. So I ended up doing it and we didn't talk for a long time.

It's 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 all right? Yeah, it's like, let's pretend this never happened.

But 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 probably I would think would probably have changed a little bit but they 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 is like one how great it could go but that it wasn't as bad as they thought. I think a lot of times when we face risks like that, we're thinking, okay, if this doesn't go right, then this could go wrong, and then this, and then, yeah, you end up living under a bridge. The truth was when I went to drop out, I walk in the registrar's office, and I'm like, I'm 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 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, all the years of 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 and 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, 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, 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 two so I went to two years but really I got three years if you think about it um 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 i wasn't like in any of these life-changing class like i wish i'd taken i 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 figure it out but actually you'd be much better off going like you know you know what it's like it's like you know on that show like supermarket sweep yeah if like if you're just like 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 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. Yeah, no, I get, I mean, I don't want to go too deep into schooling, but it's, I feel like there's, 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 elective?

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. mean some and it's funny a lot of the classes were electives i remember i 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 i mean 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 30 or 40 000 a year is a very expensive price tag to pay to figure something out 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 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 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. About even. 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 or 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 and like in that world meeting people learning things like figuring it out sort of in the scene before i ever was writing anything myself when 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 at this generation remembers. Can you tell us a little bit about that and what that experience was like? How did you even end up there and how did you even get involved in that? It was a, it was another random thing because, uh, 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 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 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, this is an interesting, I wasn't even going to ask this question, but we were just talking about it at breakfast with young people in general. And there's people we have experienced. And this is not to throw anybody under 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 into 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 tasks, menial tasks that they may not want to do come along and they kind of say, well, 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, I'm 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. Yeah, you got to get uncomfortable to get comfortable. And I don't think, I think a lot of people aren't 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 and in a weird way that's actually where the biggest opportunity is in my opinion because um everyone is pretty good at the stuff they like doing if you can be the person that can do or excel at the things that other people don't like doing um that's a real opportunity and in um it goes the enemy i i talk 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, I'll do it. And I'll break down the film. I'll 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 and in a way with robert it was like i started doing little things and i was 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 and i think depend that 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.

And constantly finding angles as well. And they're important. Yeah. Okay, so I'm going to kind of switch gears here. 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 start, 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 uh you know he 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 uh that i'd been hired and he's in rehab and he's in rehab so it was unreachable for 30 days uh and then i've moved to a new city um i'm supposed to be doing all this stuff and then this is a this is a i don't know if i've talked about this but um so when i'd met robert and he decided to hire me uh he was like give me your phone number and i'll call you and we'll 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 gonna be this exciting awesome thing turns into a complete shit show almost immediately i almost lose both jobs that i just left college for uh mom and dad are pissed well they 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 it. So I can't even be like, Dad, you'll never believe what happened. It was like, I can't even admit how horribly this is going. Or they'll just say, I told you so. So it was a complete disaster.

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 was like, it's going to be OK, 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 can 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 it's a different partnerships like you're on the same team working towards the same goal and like not you're not even talking income but like goes to the same spot and you're you know you're building a family and like what you wouldn't tell your business partner like i'm scared i think i may have made a huge mistake right um so he's gonna lose faith in you yeah exactly um 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 it was. And that's why one of the things I tell people is like, you can't just like jump off this cliff and not have a plan or a support system or a fallback, because it all the things that can go wrong can go wrong and sometimes they will. And how are you going to come out of the other side of that? You say when you 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 um so when i i remember when i sold it was either my second or my third book uh which and they were all in very short uh relation to each other My editor sent an email to me. She was like, congratulations, you know, like the deal's signed or whatever.

And then she sent an email to my wife that just 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, 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 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 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, because 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 that middle shelf is basically, I think that was all the books for Ego is the Enemy. So it's somewhat unfair to compare to a person who's doing it purely out of enjoyment. It's like if you went to a baseball player's house and you're like, oh, you have a lot of baseball bats or a lot of guitars. It's like, this is my job but um how much research goes into writing one book because to me this is like crazy uh i mean a couple hundred books probably um and then and then papers and articles and all sorts of other things uh a lot that's a lot so just talking about reading in general have

you always been a big reader? And how has 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 has 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 um yeah i've always i've always tried to read as much as i humanly can um 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 trying to 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. Please give me a shot. But to go to your question, 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, relationships but i think um 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 someone like that. Although I'm really actually impressed by people who do it on their own because I'm not sure 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 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 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. What was it called? I hope they start bearing hell. It was a huge, and you did all the marketing behind that and i 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 a big success uh just by word of mouth alone it's a great book and i think i have it. I have some up there. And then they, they turned it into a movie and it was like an independent movie. The movie is not great, but the marketing was great.

And we had a, 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 contract? Like the thing that was like, how do you get like young men to go see

a movie? I thought one of the ways would be, what if you told them that they shouldn't be allowed to see the movie? And so we created a boycott around it. And so it started with protests, and then it was a big thing online. And then we'd had enough budget to buy ads, I think, in three major cities. One of the cities was in Los Angeles. I thought, what if we go and we vandalize the billboards? The billboards had been designed to be provocative. People were talking about it online. I thought, what if we graffiti over the billboards?

We start a thing about people doing that. You did this prior to putting them up or you guys actually went up? No, no. 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 was like Olympic and – Olympic in La Cienega maybe in Los Angeles. It was in Hollywood, yeah. 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, um, to Curbed LA, which is a big LA 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 a sort of organic uprising against the movie um but i'd started it and uh and inevitably it brings more press yeah it got all sorts of attention and you didn't have to hire a pr agent right no no exactly amazing um yeah it was what book told you to do this no it was 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 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 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, I mean, I think it was actually part of some of the stuff that we'd done at American Apparel 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. um and then we realized um so there was this this like a street artist who is who's like uh 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 they're like 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 um where is this and blah blah blah and this went on for like a year um and then the crazy i remember the crazy thing was then we found out that actually none of them were real

like like he was just photoshopping them on to buildings and then taking pictures of them or and then 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 house 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 $0. 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 yes right right no and and when you start to get it's like if you get all that attention you it starts to ripple through culturally for other reasons right so yeah kanye west talks about it in that one song and um it was uh it was yeah it was cool we were just we

were like the company that everyone was always talking about, but that wasn't an accident. Do you know what I mean? I love it. And our advertising budget was like in a good year, like $10 million, not a hundred million dollars. Like it would be for, 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 I have a background in marketing mostly for small businesses um on the side if I'm not running one of my companies and uh I was just curious 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 you, when your other work came out, I was 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. Cause my, my thing was was like this is all really fun and there are cool stories to tell but it's not all fun and games like you could do the same playbook to become president or you could do the same playbook um to spread hate or to any other sort of negative uh more damaging message um and plus like it 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 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. 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. 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, on the one hand, they're 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 Obstacle is the Way. So I was still, 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 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 know, you're not going to you're starting from nothing and you know 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 you know how does groupon become one of the fastest growing companies of all time or or like it's 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 Bowl and you saw an Uber commercial. It just sort of happened. And that kind of growth is what growth hacking is about. The first time you used Airbnb, how did that happen?

Why did that happen? So if there's an influencer listening um 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 the first thing that growth hackers really look at is 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 uh 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 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 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 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 is the niche? 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 house. 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, makeyan make this ad yeah and then it was like i didn't know how so i made up a i made 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 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 like you're 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, uh, you know, I studied English and I built this blog or, you know, i help my friends start this youtube channel or like i 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 yeah it sounds like that's the same for you yes uh elon musk talks about this idea of like going to first principles do you guys know what this means so basically it means like um so when he's starting uh spacex um 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 would go like okay we're gonna buy this from this supplier and this from this supplier and then we assemble it and 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, you wrote about that example in Obstacles Away now, is that? I might have. Or did you write about that somewhere else? I think, 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 like if I was using Zappos because they had the best prices and then the shoes that I got, they sucked or they were broken or something. And then so I was not going to be a Zappos customer anymore. But I emailed 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 a customer. 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 it with Tim Ferris last night that's amazing yeah he's so cool he's the best yeah we love his podcast uh 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 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. 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, 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 those people. I can imagine now the books help as well. My books? Yeah, totally, totally. It's almost like content marketing for the clients. It's like a resume and book format almost.

Yeah, I mean, like, that's another thing. It's like people go 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, 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, yeah, I was the other way. Yeah, yeah, yeah. And so I think it's about building a brand or a reputation that then you can monetize 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.

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. We'd have to do chores. But the one thing that he spared no expense, like anytime you want to go to Barnes & Noble

or anywhere, I'll buy you any books that you want. Anything you can read. 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. 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 like I remember having to do chores and mow the grass and all these things to save up for like one video game yeah and it's

unlimited books but unlimited books and so I guess you know while 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 15-year-old kid. That's insane. And I kind of got through it, but I don't think I took everything away from it, right? Sure. I 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 yeah how would you define it i kind of define it and the reason i like it is i think it's it's a it's philosophy which a lot of the time kind of turns people off yeah but i think it's one of the most logical it's it's a practical philosophy right so most people think philosophy is like what university professors 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 like if you don't do these things you'll go to hell but it's saying like these things make don't go these things, you'll, like, if you don't do 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 would call the 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 feel not stressed? 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 that, 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 comets. Yeah, maybe we could give a little context of the history of stoicism. Yeah. So if you've seen the movie Gladiator, Mark Ceruleus is the emperor.

He's the old guy. Joaquin Phoenix's character who kills him, that's his horrible son. And that actually did happen. 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 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. So my sort of definition of Stoicism is basically that like the stoic believes that we don't control what happens around us we just control how we respond and that's 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, you know, 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, there's, you know, 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, not your family, not outside events, not, not politics, not who's president, who's not, 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, uh, something could happen to it, right? You only control your own body, right? Like in the sense that like, something could happen to it, 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 it'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 there 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 x basically 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 not a great way. So the Stoics are like always thinking about the worst case scenario. They're prepared. They practice for things to go wrong. But when you're in that

stress, you're going, 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, 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 are 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 gonna i'm gonna proceed anyway i'm gonna do my best you know like it's it's not just like oh i'm gonna 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 gonna do my best they wouldn't let a stressful situation shut them down yeah of course because um 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 i did love it it And it, like I said, it reinvigorated my interest in going back and actually reading the stoic work. And that's what I, yeah, that's what I wanted to happen. That was my, 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? Um mean really practically like when i start to get really rattled uh 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 um and then uh 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 fixed in the garage and the roof of 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, um, if I do it piece by piece, I'll start to make process or make progress. Yes, yes, exactly. Right. Why, why am I believing this is still, still stressful? Well, it's just, I think when you, I think the problem is with people, they, they, 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 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 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 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 this 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. Wow, that's 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 those. But like on a normal week that wasn't a launch probably 5 000 that's so many so but it's really not like not compared to a million it's not compared to a million and so it's like uh people 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 where that person was where you aren't i 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, 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 of the last one, I feel bad. And so 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 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 uh 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 like the really shitty and really boring

parts of my life it would have like zero followers because who would want to 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 to 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 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 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 a little bit about living in the moment. 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 maybe Marcus Aurelius, but it 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. 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 is is out of your control or it's not up to you and it's by the way might not even happen like because you could die so they'd go like uh the 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, all that you have. I have a quote from Seneca 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, 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. Like 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 an 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? Um, like it's not like, oh, uh, you could die tomorrow. So don't save for retirement. You know, like it saving for retirement is, 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 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. 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 overcommit 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 um yeah i mean i think i think i am i

think most people are but i 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 the, 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 beard. James Lipton. Yeah, James Lipton. I don't want to sound like that, dude. But the reason I think I identify with your books is you take subjects that may not be the most like titillating the most exciting subjects and you make them very accessible to and entertaining to readers so like

like I said reading marks to realize meditations that's a difficult book for anyone that's not a like 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 you it 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 reflected 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 100 but it's sometimes you know it's difficult sometimes to differentiate between competence and ego yeah maybe that's is that the right way to say

it no that's totally right um there's a quote i have in the book from one of the stoics uh where he says um uh 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. 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 Conor 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, but maybe has his ego in check. Like every time he's taken a loss, he's been very humble about it. And he said, you know, I could have done this better.

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 um but i think he also i bet he's i bet he looked at 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 i don't think he looked at that in

any way he's like this is going to be easy he wasn't shocked don't you guys think though that he was looking at it from a marketing standpoint completely not of course 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 um and then he's probably like but either way you make a hundred million dollars so and there's also no i mean the what i mean what i always tell people too is like people like oh he lost he's done but and they said now he has to go back to ufc and he's gonna maybe not get paid as much but 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 he's going to 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, you know, working in a soup kitchen or, you know, hiking in a national park. Like, don't live your life for social media. Let social media be a reflection of things that you do. And then make sure you're going out and reminding yourself just how much is out there.

Do you know what I mean? One of the ways I keep mine in check is just 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 yeah i tried to keep it in check yeah what the hell are you doing with us though yeah just kidding or i like to hang out with like people that just like like where i live uh most of the time like on the farm is like none of these people care at all about who

i am you know 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 it doesn't they don't just have to be smarter than you like so they get 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 or but just like people who are better than you at some new or different thing like 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 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, work that's very different than the work that comes naturally to me at this point so um you

know like today after this uh i have to go uh like seed several fields uh and my wife's like picking up the the grass seed right now we have to like plant for the the 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 farm as something where you step out of your writing and 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 in the same way see now when i say i need to wrap my head around something i'm gonna refer to Ryan you gotta wrap your head around a lot of like 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 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 gonna be home like why did you go to the gym it's like no work just took 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 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 have i can't meditate either i've really tried and i've tried to read up on it and 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 are 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 tried to do Tony Robbins priming. Okay. It's, it's okay. It's, 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. So let's talk about what we're, you know, kind of what we're here to talk about, which

is perennial seller. Okay. Um, your most recent book, the perennial seller, 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, it's, is it done by month or by week? Uh, both.

Okay. Month and week. How books are selling or is there multiple? Okay. Um, but a perennial seller is maybe not factored in so that'd be like books like maybe harry potter yeah or it's the mocking or not to kill a mockingbird catch on 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 okay it's from the things that are 10 years old or 5 years old or even 18 months old. And even my own books, The Obstacle is the Way 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 back on the list. But it's never hit any of the lists, ever. And so when someone says I'm a best-selling 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 uh you know um i know people who have a million twitter followers but their tweets get seven retweets meanwhile 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 like for me i'm not a writer right and for lauren you know she's a 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. It's 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 the marketing is like another creative canvas you know i heard you talk about the difference between seinfeld and friends can you can you talk about that because that i love seinfeld no that really put it in perspective for me well people have gotten mad at me because i guess i guess friends is like

popular again with like you got a big community not like seinfeld though that well that's my point that's my point um and and in some ways i would wonder if like friends is having a resurgence because like everything has gotten so much dumber that like friend seems like smart in comparison do you know what i mean but uh nostalgia yeah yeah it's like uh it's like compared to like logan paul uh friends is like a smart television show um but uh you know seinfeld seinfeld as a television show has made more than three billion dollars since it went off the air because of reruns syndication netflix uh is it netflix or hulu deal um uh 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 got, Friends is a drama, is a dramedy. 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 what and i always think back like i don't know i didn't i was never a big friends family but a big seinfeld guy there's so many 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 to go 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

where kramer gets a job like gets hired at a place but he doesn't actually work there you know like that 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 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 it's sort of got that timelessness built into it. If, like, I remember some episode of Friends where they're, like, they're all going to, like,

a Counting Crows concert or something. Well, that doesn't stand up that well. Like, if you think about what happens in Seinfeld, there's no, like, 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 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 uh it takes however much work you think it takes it's like 10x that do you know what i mean um just way more than you think um and i 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 you know 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 seven million subscribers and it's like

that wasn't how it went at all yeah 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? You've been asked we don't have the time. I wanted to, this may, 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 it out

and you go through another editing process and on 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.

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're both practiced because both of us don't come from anywhere near this background. So's your take 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 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 there's 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 i 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 uh well i mean in growth hacker i'm talking about that sort of minimum viable product you all my books start with articles that i'm testing and getting feedback on so it's very it's very risky and very hard to like do this stuff in a vacuum and like hope people like it so i i'm i'm 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 I know it's good. It's really, really good. 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 a medley of books.

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 which book of yours would you recommend? I'd probably start with The Obstacles of the Way if I was picking one for me. If I'm picking,

I'd go with The 48 Laws of Power from Robert Greene. I think that's a must read. My favorite novel is What Makes Sammy Run by Bud Schulberg. I love that book. These are 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 Steven Pressfield.

I love The War of Art. Yeah. Of all those, I've 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 copies.

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 find your book? Pimp yourself out.

Books. Yeah. So all the books are on Amazon. Just search my name. can everyone find you where can they can find your book pimp yourself out books but yeah so all the books are on amazon uh just search my name uh my website's ryanholiday.net and then i think i'm at ryan holiday pretty much everywhere what's the address of the farm please don't come thank you so much for sitting down and taking the time with us you are a smart dude if you like this, 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 asklauren, Lauren with a Y, at theskinnyconfidential.com and we will send you my five beauty tips and tricks straight to your inbox. As always, follow us on Instagram at theskinnyconfidential and at michael Bostick, and we will see you next week.