The Learning Leader Show With Ryan Hawk - 088: Ryan Holiday – How To Find The Best Mentor & Viewing Obstacles As Opportunities

Episode Date: January 11, 2016

Episode 088: Ryan Holiday – How To Find The Best Mentor & Viewing Obstacles As Opportunities Ryan Holiday is a fascinating thinker.  I appreciate his stories and the manner in which he views the world.  This conversation was entertaining and educational. Ryan is an incredibly interesting person.  During our time together, Ryan talked about stoicism and why he’s fascinated by it as well as you should be willing to work for free (as long as it’s for the right person). Ryan Holiday is a media strategist and prominent writer on strategy and business. After dropping out of college at nineteen to apprentice under Robert Greene, author of The 48 Laws of Power, he went on to advise many bestselling authors and multiplatinum musicians. He served as director of marketing at American Apparel for many years, where his campaigns have been used as case studies by Twitter, YouTube, and Google and written about in AdAge, the New York Times, and Fast Company.  His most recent book, “The Obstacle Is The Way” is based on the Stoic exercise of framing obstacles as opportunities. The book has sold more than 100,000 copies and was reportedly read by the New England Patriots during their 2014 Super Bowl Victory over the Seattle Seahawks as well as distributed through the locker room of the Seahawks in the following offseason by the team's front office. Episode 088: Ryan Holiday Subscribe on iTunes  or Stitcher Radio “The best leaders are process oriented… Not results oriented.  They are focused on doing great work more than on acquiring lots of money.” The Learning Leader Show Some Questions I Ask: What are the common characteristics of leaders who have sustained excellence? Why should we be willing to work for free? Why was it the right decision for Amelia Earhart to knowingly be paid less than her male counterparts? What did you learn working for Robert Green? Why don’t you like the title for your first book, “Trust Me, I’m Lying?” How do you “trade up the chain?” What is the proper strategy for your first book? What specific changes have you made to grow your following? What is your process for writing? Define a great learning leader… In This Episode, You Will Learn: The importance on being process oriented rather than results oriented Why working for a fantastic mentor will massively accelerate your success Austin Kleon – “Say yes, until you can afford to say no” Why using a job as a journalist as a great excuse to interview people Stoicism is an ancient Greek school of philosophy. The school taught that virtue, the highest good, is based on knowledge, and that the wise live in harmony with the divine Reason (also identified with Fate and Providence) that governs nature, and are indifferent to the vicissitudes of fortune and to pleasure and pain. A very interesting Amelia Earhart story Why continuous learning is the key to success “An hour of Sheryl Sandberg’s time is hard to quantify.  It is so valuable.” Continue Learning: Go To Ryan’s Website: net Read: The Obstacle Is The Way Follow Ryan on Twitter: @RyanHoliday Read Robert Greene’s: The 48 Laws Of Power You may also like these episodes: Episode 001: How To Become A Master Connector With Jayson Gaignard From MasterMind Talks Episode 034: Jimmy Hatch – Shot While Searching For Bowe Bergdahl And Sky Diving With Gabby Giffords Episode 004: How Todd Wagner (and Mark Cuban) Sold Broadcast.com To Yahoo! For $5.7 Billion Episode 010: Shane Snow – How To Accelerate Success Using Smart Cuts Did you enjoy the podcast? This was a jam packed episode full of great content.  Ryan Holiday is a leader who leads an very interesting life. Who do you know that needs to hear this?  Send them to The Learning Leader Show! Episode edited by the great J Scott Donnell Bio From RyanHoliday.net Ryan Holiday is a media strategist and prominent writer on strategy and business. After dropping out of college at nineteen to apprentice under Robert Greene, author of The 48 Laws of Power, he went on to advise many bestselling authors and multiplatinum musicians. He served as director of marketing at American Apparel for many years, where his campaigns have been used as case studies by Twitter, YouTube, and Google and written about in AdAge, the New York Times, and Fast Company.  His most recent book, “The Obstacle Is The Way” is based on the Stoic exercise of framing obstacles as opportunities. The book has sold more than 100,000 copies and was reportedly read by the New England Patriots during their 2014 Super Bowl Victory over the Seattle Seahawks as well as distributed through the locker room of the Seahawks in the following offseason by the team's front office. His first book, Trust Me I’m Lying—which the Financial Times called an “astonishing, disturbing book”—was a debut bestseller and is taught in colleges around the world. He is the author of two other books and is now published in 16 languages.

People were mad that Cheryl Sandberg, who's the CEO of Facebook, was offering an unpaid internship. And people were like, you're a billionaire. You can afford to pay. And like, when I saw that, I was like, do you know how much an hour of Cheryl Sandberg's time is worth? The fact that you would have access to this person on a daily basis and you don't not be getting paid whatever minimum wage is, like, in exchange for that is like the bargain of a century. So you're saying like you're not only, you not only feel entitled to work for, like you not only feel entitled to her advice, but you feel like she has to pay you for the privilege of giving you advice.

Like, are you out of your mind? Are leaders born or are they made? Our host, Ryan Hawk, believes that leaders can be made through determined, focused work on learning the art and science behind the makeup of other successful leaders. Now it's time to inhale knowledge and exhale success. You're listening to The Learning Leader Show. with Ryan Hawk. Hey and welcome to the Learning Leader Show.

I am Ryan Hawk. So excited for tonight's featured leader. It's with the great Ryan Holiday. This one is about 10 months in the making. So I'm so pumped that we got this one done. And I loved it. Ryan is a media strategist and prominent writer on strategy and business. After dropping out of college at the age of 19 to apprentice under Robert Green,

who was the author of the 48 Laws of Power. He went on to advise many best-selling authors and multi-platinum musicians. He served as Director of Marketing at American Apparel for many years, where his campaigns have been used as case studies by Twitter, YouTube, and Google, and written about in the New York Times and Fast Company, among others. He's also the author of two best-selling books. Most recently, his incredible work on stoicism called The Obstacle Is the Way. A couple of the things we got into during our conversation tonight.

Why you should be willing to work for free or very low pay. There are particular times and moments in your life where this is the proper strategy to employ. And Ryan talks specifically how this has been the key to his success, namely when he went to work for Robert Green for extremely low pay. And prior to that, how he worked for other authors for no money at all and how that's led to success. And then an interesting story about Amelia Earhart and the fact that she was offered a position and the same position as two other her male counterparts. And they told her specifically, you're going to make less money than the two other guys that are going to be doing to the exact same thing.

And we talk about why she said yes and why that yes was the key to her long-term success as well. And then his process for writing, how he does it, where he does it, why he does it. I'm really interested always to know the practical side of how things get done. And Ryan employs some tactics that I think are phenomenal and could help us in all areas of our life. Without further ado, it's the great Ryan Holiday. All right, Ryan, so excited to have you here on The Learning Leader Show. And I got a quick question to get us rolling, man. And that's around sustained excellence and people that have done that over long periods of time.

and you are a person who has sustained excellence, and you've spent time and certainly studied people who have done that. And I'm curious, what are some of the common characteristics you've seen and kind of picked apart that those people all seem to share? Look, I would say the biggest thing is probably amongst the successful people that I know. They're very much sort of process-oriented versus, like, results-oriented, not in like their daily lives, but more like on a project level, right? So they are focused on like doing really good work.

Like that's what they focus on. And like I tend, I guess what I'm saying is I tend to find that as you sort of go up the chain in terms of success, it's less about like impressing other people or hitting certain arbitrary goals. And it's more about like producing work that they're really proud of. So this is especially true in the writers that I really. respect. They're always working on a book and that book is, you know, maybe it's, it's an unexpected sort of direction or it's a change in style or whatever. But I'm not like, hey, what are you doing?

And they're like, oh, I'm trying to write a number one New York Times bestseller. They're, like, they're trying to instead focus on making something that like is, like, I guess what they're saying is that the results are somewhat outside of their control, like the, in terms of the public reception of the product, and they're focused more, like, I guess an analogy with it, like, you find that really successful people, like, don't care about money very much. Like, they're not trying to earn money. They're trying to do, like, work that they really like, and the money is sort of a byproduct of that. And I tend to find that that's true in the creative arts as well. They're not trying to write a number one single, or they're not trying to sell a

certain number of albums. They're trying to make something really good, and then it just happens that that correlates with the external metrics that people who are not in that industry tend to be impressed by. Who are the first people that come to mind when you think of that success, sustained excellence? Yeah, so like Robert Green, who's probably the most influential mentor that I have had in my life, has sold millions of books, you know, been on every list that you can imagine, but he doesn't do all the things that other authors are like supposed to do, right? Like he doesn't really do any marketing. He doesn't do any speaking. He does very little consulting. Like he's just working on books, right? And he's just working on them sort of quietly in his house.

And so I admire that a lot. I don't necessarily emulate it as much as I probably should. But like when I look at someone who's made these things that will probably be here for like 100 years, I imagine it has a lot to do with his willingness to sort of trade maybe short-term accolades or short-term recognition or, you know, participation for, you know, like long-term lasting impact and pouring all that energy into the work itself. And you, so let's take a step back. You worked with him for him, so I've read about and the fact. So what were the steps that got you that.

role working for him. So I was his research assistant for a number of years. I sort of saw it as an apprenticeship. And then now I've worked on the marketing on some of his books. And I do some other stuff for him as well. But I was in college and I was working for another author who happened to know Robert. And I was like a huge fan of his work. I sort of knew it backwards and forwards.

I was very heavily influenced by it. And I got, basically what happened as like, I was working for this other author. And what happens when you work for people who are successful, they try to, and you don't, you know, you don't get paid very much, they try to find like ways of rewarding that work. And usually that reward is access or certain opportunities. And so the author that I was working for,

who you've had on the show, Tucker Max, he invited me to a lunch he was having with Robert. And so I got to go to this lunch. It was like sort of my, this was like my payment for the services, right? And when I met Robert, I was obviously like, you know, very starstruck, but he was looking for a research assistant and I sort of applied for it. And he gave me a bit of a tryout. And I did well at that. And it sort of became, it developed into something more official and long term. but it was just, you know, like a chance meeting, jumping on an opportunity, and then it became this thing that that sort of changed my life. It's interesting.

I love those stories. It reminds me of Joe Descena. I don't know if you know Joe, but he started this Spartan race. And it's, you know, it's all over the world now. And Joe, when I asked him what advice he would give to people who were earlier in their careers, maybe college kids are just outside. And he said, find somebody that you admire, somebody that you really look up to and offer to work for them for free. It feels a little bit about kind of like what you just were describing with Robert Green.

No, that's exactly what it was. Although I worked for a bunch of different people for free before Robert. And Robert, so like the hardest thing to do on what Joe is recommending is to transition from the free to paid. And usually the people who you work for for free have a hard time ever paying you, right? because like they sort of know your bottom line. And it's hard for them to change their perception of you as well. Like you're you're always like somebody's kid brother, right?

And that never changes even when you both get old. So with Robert, I'd work for all these people for free. And I offered to work for Robert for free. And he was like, nobody works for me for free. And his what, I mean, this makes sense. I probably should have thought. There's actually one of the laws of power is like disdain the, free lunch. And basically, Robert's point is that, like, you know, you think things are free,

but you pay for them in other ways. And so I think he just thought it was like cleaner and simpler to, you know, to pay someone to be a research assistant rather than to be like on the hook for all these like intangible sort of mentorship obligations. Like right now I get a lot of people that email me that want to work for me for free. And I turn probably, well, 100% of them down because like, It's not free for me, right? It's free for them because their time's not worth anything. It's not free for me. And so anyways, Robert, like, said that he wanted to pay me.

And to me, the money was secondary, but it was like my first, obviously I'd had other jobs before, but it was my first paying job in the field that I, you know, as in writing, which is what I ultimately wanted to do with my life. And so it was a huge step forward for me. And I don't even remember what he paid me. but like it's this idea of you work. Austin Cleon is a great writer. He has a book.

Steel like an artist. Yeah, yeah. He has a great line where it's like your job as a writer, as an aspiring writer, is to say yes until you can afford to say no. And so like for me, it was like I said yes to everyone who wanted to work for me for free. And then finally I got someone who was willing to pay for me. And that's sort of what started me on my path. When was this? I was 19 or 20 years old.

I guess I was 20, so this would have been around like 2007, 2006, 2006, 2007, 2008, somewhere around there. So not really that long ago. So I'd love to dive into your story now, Ryan, because you're still obviously such a young guy to have accomplished so much. And like I mentioned earlier, sustained this level of excellence over a period of time. And I want to dig in and really, that's the whole point in my show is to figure out how and why and the mindset that you've had going into this. So if you could take us back to that, you know, your 17, 18, 19, the thing, the way you thought, what you specifically did, which is which, you know, and you can include obviously the books, the bestsellers that you've written along the way that's led you to where you currently are today, still having this big success at a really young age. Yeah, so the thing about being, having done this stuff at a young age, it's a little bit different for me is like, so I was working for Robert Green and then I'll get into this. But I, and then I also had another job like I was working in Hollywood at a talent agency and then I was working for Tucker at the same time.

So I sort of saw it as doing these things at the same time. Like I felt like there was more than enough time in the day to do more than one thing. And so I felt like, okay, instead of, like, it's like, think about it this way, it's like, you go to high school, then you go to college, and then you go to grad school. And that takes, like, 12 years, right? But college isn't actually that hard. In grad school, there's not that much going on. If you can compress those two things down or do them at the same time, you would learn the same amount, but you wouldn't, you know, give up an extra four years of your life, let's say. And so for me, having these sort of multiple apprenticeships simultaneously allowed me not only to learn a lot more and sort of combine what I was learning in one field and move it over and apply it to the other one, but it massively accelerated like the sort of amount of time that I had to spend like paying my dues.

And that was like really huge for me. So instead of, let's say, like learning a lot about marketing and then deciding I would write my first book. and then having to learn how to write, I was learning how books are made and then also had my career in marketing, and then I was able to sort of combine those into a new thing. So that's like an approach that I took that was a little bit differently. I sort of combined my various educations all simultaneously. And then, of course, I dropped out of college, which accelerated things a little bit. But more or less, the sort of highlights of my story are I was going to college, not a great school, but I'd sort of pick the school that was more in the region I wanted to live in,

like near Los Angeles. And I was writing for the college newspaper, and I reached out to Tucker and a handful of other people that I wanted to know and meet, and I used the college newspaper as like an excuse. Like I would interview these people, and that's how I developed a relationship. And Tucker was living in Los Angeles at the time, and we had struck up a friendship and I, I offered to be an intern for him for like a summer. And I ended up moving to Los Angeles. I lived at his house.

He helped get me a job at a talent management agency. So I would like work there during the day and then I would come home. And he and I would work on his stuff, like his websites and his books. And so I was doing all this simultaneously. And it was like one really busy summer, basically. And at that end of the summer, I'd help the talent management agency sign a number of sort of big, internet-focused clients, and they were like, what if you didn't go back to school? And I'd not thought about it, but sort of pivoted my whole life. I dropped out of college. I moved to L.A.

And I did all this stuff simultaneously. And then I met Robert shortly thereafter. So I had these three things that were sort of total, like, I was like more than above my depth in three different, but related fields at the same time with really strong mental. tours in each one of those categories. And I was just learning everything that I could until eventually this had sort of come together into a skill set where through Robert Green, I got a job at American Apparel, which was like a very fast-growing, you know, fashion company at the time. And I, and then I sort of put the other stuff on pause, dedicated everything to that.

I became the director of marketing at 22 or something like that. and then did that for a number of years until I wrote my first book in 2012. Trust me, I'm lying is an interesting title to a book. Yeah. I've read that you actually don't like the title. Is that accurate? Look, I appreciate the title in the sense that it, I think it did. It helped the book.

I don't love the title in the sense that, you know, I never saw it as being the end-all, be-all of my career. and so now I have to like talk about whether I'm a liar or not to a lot of people when that's really like now what the book is about at all. Right. And it's not like who I'm about as a person. It's supposed to be sort of an expose about it. It's both like a personal memoir and an expose of how the marketing and media system works and how one can take advantage of it and sort of get sucked into it. And the title is just sort of a joke, but it's had some lasting less than place. wasn't effects in my life.

But you got to take the bad with the good. What type of lasting bad effects has it had on your life? I mean, just in the sense that like, people will be like, oh, Ryan's a notorious liar. And it's like, clearly they haven't even read the book because it's not what it's about at all. But so it's just, you know, it's just like, I'll say not only is it a little weird, like in terms of what it implies, but like it doesn't do a great job telling you with the book is about. The subtitle Confessions of a Media Manipulator, I think, was the title that I wanted

and I think would have served the book better over the long term. But who's to say that there would have been a long term without the short-term boost of the title. So I'm willing to accept it and take it for what it is. What's the decision-making process like when it comes to titling a book? Like, who makes that final call? Well, when you work with a traditional publisher, ultimately everything is their call, right? It's unlikely that a publisher would, like, like I agreed to the title, right? I certainly signed off on it,

but it was a long, unpleasant series of discussions and ultimately you compromise, and as a first-time author, you're not necessarily sure where you compromise and where you shouldn't compromise and what you should insist on.

And all this stuff is easier to think about in retrospect, but, like, you pick the title six months before the book comes out, and then you mark, and then the book comes out, and you market it, and you're really guessing as to, like, and we did all sorts of tests on the title. Like, we, it was far, trust me, online, was far in a way, like, the best testing title. In retrospect, I understand that it's, again, it's testing well in the short term just as, like, you know, a title like, this is a book filled with naked women would probably do really well, too, but it's not necessarily the best career or brand-wise. So it's, it's, you compromise and, you know,

you make the best decision that you can with the information that you have. And then, you know, you learn from it and you decide what you want to do next time or if you were doing it again, you know, you speculate as to how you would have done it differently. you know there's a number of interesting stories in that book i think it's extremely useful especially for somebody jason gainart actually told me he he recommended the book uh months and months ago he was guest number one on my podcast here really when i started over 90 episodes ago and and he said you should read ryan holiday's book trust me i'm lying and i said why and he because you know you're trying to generate PR and you get your podcast and website more just notice

I guess is the easiest way to put it. And so that's why I listened to them and read it. And I think I reached out to you right around that time as well. And I know it's been some time and that's why I'm happy we're doing this. But if you had to distill that book down to, you know, a few minutes for people who have not read it to peak their interest, what would you say, trust me, I'm lying is the Genesis or not the Genesis, but the core of the book, what it's about and what it can help people do from if they're trying to, you know, if they're trying to get noticed. Or if you just said, if someone said, hey, what's that book all about, man,

that title's kind of odd. Yeah. So what I would say is it's a complete expose and explanation of the way the modern media system works, like the economics and the incentives that it operates on, both for people who want to take advantage of it and for people who simply want to understand it as a consumer. So it explains, you know, how trends are started, how brands are started, how brands can be created from nothing, how rumors make their way through culture, how reputations are made and ruined. I just tried to, like, the media system that we have now today is fundamentally different than the one we had, say, 10 years ago, certainly fundamentally different than the one we had 25

years ago. And I wanted to sort of show the forces by which that system operates for people who want to use it or people who just want to protect themselves against it. So I don't necessarily see it as like a how to book, but like a sort of how it is book. And obviously a lot of people have sort of used it to to help their careers, which I certainly appreciate and respect. I think other people have watched it, I've read it for the sake of going like, see, I knew something sort of fishy was going on. And, you know, I'm, I'm equally open to that interpret. as well. So let's get practical with the tactics, if that's even the right word, but the basis for

what you write in that book, because I want to get to obviously the obstacle is a way too, but since we're here, I'm going to go with it. And when it comes to the easiest thing for me to discuss right now is obviously what we're doing now, my podcast, my website, starting to get speaking gigs, writing a lot more, which I think will eventually end up in at least a book. And so, there's a number of different arms that come from it, but one of the things that could be helpful, and actually already has been helpful, and this has happened without even really having, trying at all, is getting noticed by whether it's newspapers, blogs, TV, things like that. So if I was coming to you and saying, Ryan, okay, I want to get more great earned PR noticed on the blogs, newspapers, magazines, TV, what have you,

what are some of the first few things you would the advice you would give me so so the first thing i sort of explain to people is that the the way that the okay so if you take like a if you take the media environment let's say like 20 years ago right everything's in print or it's on tv or it's on radio these are finite mediums like there's only so much space in a newspaper there's only so much, even like a 24-7 network, there's only 24-7, right? So they have to, they are, it's a buyer's market. They're choosing what they put on. Well, you fast forward to an internet environment in which there's not only a mass, mass increase in the amount of outlets that there are, but those outlets are now no longer subject to any sort of physical constraints whatsoever.

So like you take a site like Business Insider, Business Insider can essentially post an infinite amount of content. And that content, every additional piece of content that they publish is more ad revenue. So what this means is the media has gone from a buyer's market in which like the media is a gatekeeper to a seller's market in which anyone who's doing something interesting can find some media outlet to talk about them. and you put on top of this that the way the media outlet works is essentially uses traffic as the main barometer as to whether something is good or not, whether something is true or not, whether something is newsworthy or not. And so basically what this means is if you can deliver an audience or you can deliver something that will deliver an audience, you have what the media wants rather than the media having what you want.

And so I find that getting attention for people is significantly easier. And because of the relationship between different outlets, it's like you can get picked up by, I call it trading up the chain, but essentially it means like you get picked up by one tiny outlet and then another outlet picks up what they picked up. And it sort of goes up and up until something that might have started on a tiny website or, you know, I could say something controversial on this podcast right now or, or one of your guests could. And then the next thing you know,

you're being talked about on ESPN or on CNN or CNBC because of the interdependence on these outlets. And instead of there being like fact checking or news cycles that are slowing this process down, it can escalate really, really, really quickly. And so what I talk about in the book is, one, how this system works so people can understand it intellectually. And then I talk about how, you know, what things tend to do well in that system and how you sort of can take advantage of that system, like how you can insert yourself into that cycle.

How, how instead of just saying like, wow, that's crazy, here's how, here's how some celebrity gossip story, you know, started on Twitter. Somebody said like some, you know, crazy thing. And then the next thing you know, they're talking about it on the nightly news, well, how can you make yourself that thing? And it's really a matter of sort of figuring out what sites influence what sites in your space and also like what themes or ideas tend to resonate. There's another great book I like to recommend to people called News Jacking by David Merman Scott. But that's really what my book is about as well.

How do you sort of hijack the news cycle or the sort of the news production cycle and make it talk about you instead of any other old thing? yeah i think there's it's just really interesting and it appeals uh pulls back the curtain so to speak on what that what that's all about because a lot of times you just see it and you're like wow that's interesting story i wonder how that came about and if you dig in and you figure out how the stories actually came about a lot of times they're pitched by the people themselves who are the basis of the stories or and sometimes and i know you've written about this they're even written by the person or their people have written it about them and said hey here's something you could

easily put on business insider and we've already done all the work for you just you know cut and paste pretty much and it's done and then that's how you kind of work your way up the chain yeah or sure like you know let's say 15 years ago you were an entrepreneur or you were launching some product let's say you might want to get written about it in like fast company or Forbes or entrepreneur or entrepreneur you know any number of these sort of or ink any of these like business focused outlets, right? Well, now those outlets just take contributions from anyone. Like, there's a submission section where anyone can be published on those outlets. So instead of having to hire a publicist at $15,000 a month who then pitches a reporter who may or not write or may not

write, and what they may or may not write may or may not be positive, right? So a lot of variables that are outside your control there. Instead of that, it's now a system where you can write whatever you want on one of these outlets about yourself or about your business or about what you've learned in your business or whatever you want it to be.

You can write about yourself for those same outlets. And as far as the public is concerned, ink.com is still ink magazine and Forbes.com is still Forbes Media, the 100-year-old media brand. And so there are a lot of these changes that have happened that I talked about in the book that obviously in 2012, they were a little bit, 2011 when I was writing, they were a little bit more cutting eggs. But these are the shifts that have happened in our media system that fundamentally change what we consume and what we read and how PR is done. Yeah, I could talk about that for such a long time.

And so I'm really interested. And I'd love to talk more with you about it as we both progress. but I also want to transition because the obstacle is the way is a book that has really caught fire in the NFL as of late. And so it's made some noise in probably different areas where you haven't always made noise with, whether it's Sports Illustrated and ESPN and other people are picking it up saying this is the book that the New England Patriots read to lead them to a Super Bowl. And then the Seahawks read it after they lose to the Patriots. Now everybody is reading it. And I was fortunate to read it when it came out and was rereading it.

I was preparing for our time and I love it. What, I mean, you're, if people look online and look at the pictures of, um, your house is like a library with bookshelves and books everywhere. And so you're extremely well read, which I would imagine means you could write about a number of different topics. Why this topic? Why stoicism? What, what brought you here to write about the obstacle is the way?

Yeah, it's funny. So because trust me online came out first, most people think this book about stoicism which actually ended up being my third book is like this sharp, you know, sort of change in direction. But it's funny because I remember, like when my, I remember, because I've had a blog now since like 2006, and I've been talking about all sorts of things. When I announced that my first book was going to be a marketing book, most of my fans were like, oh, what's this about? Like, my people thought my marketing book was a change in direction. And it was only in the sense that sort of philosophy and strategy, these are the things. the things that I was most interested in. And these are the things that I've written about for the

longest amount of time. And, you know, due to working with Robert Green, what I had the most sort of actual knowledge and understanding of. And I wrote when I was, I knew I wanted to be a writer, but I knew that the first book that you publish should not necessarily be the book that you love the most, but the book that has the greatest chance at building an audience and a name for yourself. And So, like, I had held off on doing the Stoicism book for a long time. I actually got an offer to do, it was obviously a very different book deal, but I'd gotten an offer to do a Stoicism book much earlier. And I turned it down because I didn't think that I was ready.

I didn't think it was the right career choice. And so I waited until I felt like I had the best book that I could do first. And that was, trust me, I'm lying. Stoicism is something that I was introduced to around the same, when I was telling my story earlier, sort of philosophy was introduced into my life around that same time. It's what I did the most reading on. It's how I've tried to personally live my life. It's what I'm most endlessly fascinated by.

It's what I do most of my reading on. And it was the second book that I sold right after, Trust Me, I'm Blind. So I was also very conscious of not wanting to be like a marketing guru. Like, I didn't want to just have to do marketing books my whole life. And so it was a very deliberate move, not in a different direction, but back towards the original direction that I'd set out in, if that makes sense. Yeah, but it actually brings up a question, interesting one. So at the very beginning part of our conversation, we talked about the fact that common characteristics of sustained excellence are people who simply set out to do great work. They don't think about impressing others.

They don't think about money. They don't think about anything. And you mentioned that the reason that the marketing book was first because you thought it would help you build an audience, which makes me think there was a thought process behind trying to impress others to build a bigger audience, which seems a little bit backwards. So I'm curious, can we dig in there to figure out your thought process when it comes to it? Or was that because of, was there a specific reason? Or did it just take you time to think about that over time? you know, to say, well, like, tactically you're saying, I want to build an audience. That is most important before I write my book on stoicism.

No, no, that's a great question. And it requires some diving into it. It's, okay, there are certain, certain books have, by nature of what they're about, have built-in audiences, right? Everyone consumes media. Everyone consumes, many people have things that they're trying to. trying to get attention for, right? That's why marketing exists, right? So, like, when you write a book that's about a category versus a book that, like, obstacles away, that that's, like, my sort of personal approach to life. That's, like, a very contained book, but no one, no one wakes up and they're like,

hey, like, I want to, some people do. There's a very small audience wakes up, and they're like, I'm very passionate about philosophy. What are the new philosophy books out there, right? And so what I was, what I always knew that my goal was to write a book about philosophy, but I knew that in order to be able to successfully do that, I had to build an audience and I had to build a platform with which to reach the people who I knew would be interested in philosophy, but maybe themselves did not know that they were interested in it. Does that make sense? So, so, and it's really a matter of like, So it's about thinking which one requires more of a base to be launched from. And also which one is more timely or not.

So stoicism is a 2,000-year-old philosophy. It can keep for a couple years. And I remember I talked to Robert about this at the time. I was like, hey, look, I got this book deal. I got this offer to do this book. What do you think? And it was like, look, you could do it. And I think it would be pretty good.

But he was like every year that you have life experience and you go through things, the book will be better because it will be a reflection of that not. Like I was like 23 or 24 when I got the, now I was probably, I might have been like 22 or 23. So like when I finally wrote it when I was like 25 or 26, I was older and I'd gone through, you know, some shit, right? So it was a better book. And so Robert's point was like, this book will keep. you might have other books in you that will not keep the same way. And so, like, when I had the idea to do this, trust my mind, sort of an exquisite of the modern media system, I knew that it was a much more timely book and it couldn't wait the same way

that the other one could. And I knew that, like, let's say the way I saw it was like, let's say I write this marketing book and it's really good and it sells, you know, however many copies. some of those people are going to be are going to enjoy the book enough that they'll read anything that I write in the future and those are the people that I want to introduce to philosophy so that's how I was thinking about so it was less like hey I want to impress people and more more thinking like strategically right and you even see this in Robert's books right like his mastery is a less sexy book and a harder sell, right? Because it's saying like, hey, if you want to be a master,

you have to work really hard for like 20 years before you can be a master. That's not a particularly attractive sell to the world who I would say is generally into quick fixes and, you know, shortcuts and stuff, right? So he came out with that book after he'd written about power and sex and warfare, which are more marketable concepts. And so I would say generally over the course of your career, you should be taking more risks and your work should be getting more challenging. But that you have to start somewhere. You don't you don't just write, you know, this obscure work of genius that's totally inaccessible to your average reader. Put it, well, people, A lot of people do this, right?

They make no effort to relate to the world around them, and then they see themselves as like some undiscovered genius. So I was thinking about it strategically. How can I, what is the best and most strategic road for getting this work that I believe in to as many people as possible? That's different than, say, judging the success or failure of your writing based on how much money you make or what bestseller list you hit. I gotcha.

It makes a lot of sense. I want to dive into the book itself and particularly the effect it's had on so many people. I mentioned earlier the NFL and there's a great story written recently on Sports Illustrated and about the effect that this book has had on a number of different sports teams, whether it being Nick Sabin and Alabama or the Bill Belichick and the Patriots and how it's really being passed around all over the athletic world now in many different sports. What has your involvement been and what is your reaction to seeing this have such a great effect on so many people that are world-class athletes?

Well, it's certainly not what I expected when I was pitching my business publisher a book about, you know, an obscure school of Roan philosophy. being like they were like my first advance for the for trust me online was like a pretty it's what you would call um is it a major advance in poe anyways there's like some weird uh you know industry jargon about it but it was a big advance i got less than half of that for trust or for for the obstacle is the way um less money for your second book yeah yeah i mean uh trust my blind did pretty well it didn't like uh you know it didn't sell like millions of copies or anything but it's It's a book about Stoicism, if you're an editor at a publishing house, is a much less mainstream book, right?

And so they offered me less money for it. It's not that they didn't believe in it. They were just being as realistic as they knew how to be about the book. But I knew that it would, I knew differently, or at least I believed differently. I guess I can't say that I knew. But so when I was pitching them this book, like I did not, even in my wildest dreams, I wasn't like, this is the kind of book that people, and professional football I'm going to love, right? I was just trying to write a book about this philosophy that I'm deeply passionate about

and it's sort of a method or framework for thinking about the world that I have seen with the successful people that I've worked with and the people that I admire and the history that I have studied. And so I wrote the book and I put it out there. To me, the response like the Sports Illustrated article, to me was a vindication not just of the book, but of how I approached its role out. I'll give you an example. So the idea that Sports Illustrated would be writing an article about my book, like 18 or 20 months after it's come out, is in itself an anomaly in the publishing industry. Most books have very short lifespans,

and the press and media that they get is almost always focused around the release. But I really tried not to focus around that. Like I tried to write a book that would be timeless. and then I tried to develop the sort of marketing and rollout in a way that was timeless. And so for me that it somehow made its way to the NFL and it made its way to these people who I watch on TV every week and I really admire that it made its way to them organically. And then the media story sort of happened more or less on its own was to me a vindication of what we were talking about at the beginning of our conversation, which is that. that if you make something really good and you focus on the long term versus the short term,

you might pay for it a little bit in the short term, but you are vindicated in the long term. And so to me, the idea that this book has become sort of a word of mouth machine that it's sold better than anyone expected. And then I hear from all these people who I think have faced far more obstacles than I personally have ever faced and said, like, hey, you got this right. to me that's like all you can hope for in a creative project. Yeah, I love it. And one of the, I have a lot of highlights in this book. It's one of those types of books that you'll have that.

Thank you. I just want to pick out one or two of them. Starting with Amelia Earhart, and I think a lot of people pick that one out, but that doesn't mean I wasn't going to do it. Your brother picked that one out too. Are you serious? Yes, yes.

Oh, God, I should have picked something different. But it doesn't matter. I still love it. That's amazing. You guys think the same way. Well, it's funny. We talk a lot about, I think a lot of people will come up and ask me questions about, like, what he's thinking for the week and what's going on football-wise and all this stuff. And I think a lot of times we're shocked to know that I usually have no idea what's going on football-wise.

But I have a lot, a huge idea of what's going on as far as what we're reading, what podcast guests we'd like to get on our show, interesting documentaries that we watch. Like that's what we talk about all the time. I mean on a daily basis from a texting and, you know, how you speak with your best friends. And so it's not, it's very rarely, I mean, football comes up every once in a while, but it's usually something that's just funny that happened to locker room or something. Not nothing like people say like, oh, how's the team looking? Like I don't, you know, I can watch SportsCenter if I want to know that. But anyway, getting back to the book, you know, when she says, you know, she paints. words on the sign of her plane that said always think with your stick forward meaning you

can't let up your speed or you're going to crash and really what it would I take it as from metaphorically speaking is we need to be deliberate we need to be staying moving constantly heading in the right direction and when she was initially you know offered the role to that or I don't it's not the role but she was offered to be a part of a really important flight but they told her you'll have two male chaperones. They'll be paid more than you. And so a lot of people might have looked at it and said, this is insulting. And she said, I'm in.

Let's do it because she realized what it could have potentially led towards and she needed to be moving forward. I'd love to dive into that specific story a little more. Yeah. No, it's interesting because I love that story and I relate to it even though I'm a man. I relate especially to the sort of having to eat some shit to, accomplish what you want to accomplish. And to, like, those people probably think they're taking advantage of you, but really you're taking advantage of them, right?

You're sort of, and that certainly mirrors with my own career in the sense. It's like, you know, Robert Green probably thinks he's like getting a bargain, paying me very little, or these people I'm working for for free. But I'm like, I, if you told me I had to give every penny in my bank account to be able to, like, study under someone like Robert or to be able to call, you know, the people that I've, I've been lucky enough to work for and ask them for my advice at various sort of inflection points in my life. I've been like, all right, where do I send the check? Right. And like, I remember a couple years ago there was like a thing where like people were mad that Cheryl Sandberg,

who's the CEO, the CEO of Facebook was offering an unpaid internship. And people were like, you're a billionaire. You know, you can afford to pay. And like when I saw that, I was like, do you know how much an hour of Cheryl Sandberg's time is worth? The fact that you would have access to this person on a daily basis and you know not be getting paid whatever minimum wage is like in exchange for that is like the bargain of a century. So you're saying like you're not only, you not only feel entitled to work for, like you're not only feel entitled to her advice, but you feel like she has to pay you for the privilege of giving you advice. like, are you out of your mind? So I really like that Amelia Earhart story, this idea that, you know, she was willing to take this, like, she was willing to take a step back to take a few big steps forward.

And like, look, you could swap out Amelia Earhart in that chapter in the book and put Jackie Robinson in there, right, the idea that they were looking for a player who would be willing to put aside his own sort of comfort. He would be willing, although he should have been treated. an equal. And Amelia Earhart should not have had to, you know, simply accept what she accepted. She was willing to do so and he was willing to do so because he had something he was trying to personally accomplish. And by doing that, you know, sort of broke a log jam that was holding a lot of people back. And so I try to think about that in my own life. Like how can you put

your ego aside? How can you sort of orient yourself towards action as a priority? And And that's why I love that story and why I put it in the book. I do too. And it reminds me of, I think it's Richard Branson. Did he say if you're offered a seat on the rocket ship? Don't, you know, don't ask which one. Just get on. Right.

And don't ask what they're going to pay you to get on the rocket ship. Like, but that's what people do, right? Yeah. So most of like I graduated, my graduating class of college, although I dropped out, graduated in 2008. So into the financial recession. And most of my friends didn't go get crap. happy jobs at the bottom of the rung and then worked themselves up. Most of them went and lived with their parents while they waited out the recession or they went into more debt and, you know,

stayed in school. And I think that was because the idea of, you know, taking that step back, it's like, I'm a college graduate. I shouldn't have to work at Starbucks. It's like, I'm sorry, but like just because you have a piece of paper it doesn't guarantee you anything in life and i think i think that's what you know really impressive people in history they've always been able to look at these situations objectively enough put their own entitlements aside and and say like no i want to do this enough that i don't i don't i'm not going to waste any time you know negotiating about terms i'm just going to say yes i know we're up against it i got a couple more questions ryan i i actually have like a thousand more but I'm going to get to just a couple of them I'm curious when I I want

you to take us to the place when you are in your element writing and I've read that you you can't imagine a more a worse place to write than like a Starbucks or something like you like you like you like old libraries and things like so what's it what is it like for somebody if we were peering in to see Ryan Holiday write his next book or write a next great article where are you what type of computer do you use what is it what it what it was What environment are you in when you write? Well, so I write in my house now, or I have an office, not at the house that I live in, where it's the picture people have seen where it's like all my books.

That's my office now. I go in, I find that you've got to go somewhere. Like, it's hard just to, like, walk, you know, to another room and then start your job. Like, I feel like I commute to my office, even though I could work from home. I commute. I sit down. I've written in libraries and stuff, too. I find that, like, I need quiet and I need dedicated amounts of time, and I usually need to do it in the morning.

I find that, like, Shane Farnham, or sorry, Shane Parrish, who has a site called Farnham Street has a great post where he says, like, if you want to be more productive, just wake up early. So I tend to be an early riser. I get most of my work done early. I would say the big thing about me as a writer in terms of productivity that I learned from Robert that, you know, a lot of aspiring writers may be. miss. Writing is not the act of sitting down at a computer and just spinning out what, you know, you think is great. Like there's that Hemingway quote, like, writing is easy. It's just sitting down at a typewriter and bleeding. It's not that. I find that the hard work and the critical work in writing is done in the research. And this is true for fiction or nonfiction. And so for me, like, the research process for a book might last eight months or a year. And then the writing might only

last two months or three months. The writing is simply the act of stringing the thoughts together, but it's the accumulating the thoughts and grounding those thoughts in the research that takes the longest amount of time, and that's where I spend most of my time personally. It's interesting to me when people say, you just sit down and write and just get your thoughts out there, and eventually it'll turn into chapters, which the chapters will turn into books. And I've said, the best books I've ever read, they're all so heavily researched. And that's, I think, why the thought of, and I want to put this, you know, a lot of what I've learned from people down in a book, but it's about, and I'm doing the research every day by having these conversations,

but there's more than just that. And that's why it seems like a daunting task to me, because I'm not just going to write what I think based on what people have told me. There's a lot more that goes into it. And that takes time and structure and learning. That's why I usually ask this question to people who are great writers, because I want to feel and know, okay, how does a Ryan a holiday put together these great books and great articles. It's not like you just sit and sit down and write. There's so much research that goes into, which is even more work than the actual act of sitting at your computer and typing.

Yeah, I try not to do any writing until I've cracked the organizational structure of the given thing, whether that's an article. Sometimes in an article you can wait a little bit, but definitely with the book. Like, what is part one, what is part two, what is part three? What are the chapters in that? What is the intro? What stories are you putting? where and why.

You have to crack that first. Part one, part two, part three. Why do you use that format to write? I mean, it doesn't always need to be three parts. This happens to be, I mean, my last two books have had this. I mean, look, you know, act one, act two, act three goes, you know, back to Aristotle. It's pretty tried and true formula. It doesn't always have to be that.

It could be five parts. It could be two parts. I mean, whatever. I mean, my first book is two parts. my second book is four um but the organizational structure it's like i it's like five paragraph essay right what are the three body paragraphs going to be about you got to know that you don't write the intro and then figure it out as you're going because you already wrote the intro you already introduced what the three things are so you have to that organizational structure unlocks or i guess

you could say eliminates a lot of the stress and and aimlessness of writing the other thing you do obviously from your reading is have these, it's really interesting pictures when you go, I urge people to go check them out online when you, if they Google you, when you could see the note cards of your notes from reading other books. Talk to me about why you take notes in that manner of note cards that you then place in, it looks like tabbed folders in boxes. Yeah, so the note cards are how I organize the research. And you do the physical note cards. Again, I learn this from Robert, but the note cards allow you, so you read this book and you, you hear a great story. Let's say I hear the story about Amelia Earhart. And I'm transcribing,

I'm transcribing the great parts of that story onto the note card. Well, maybe originally, I think that that is a great story for part one. And that's how I'm organizing it. But then I change something. And now I realize actually it's the perfect opener for part two story number one, which is actually where I think it is in obstacles way. So now I can just physically move that note card into the different section. And then I'm able to pull that note card out. And then I'm able to pull that note card out when it comes time, you know, two months into the process to write that story. And so it's not just enough to read or to research or to, you know, expose yourself to great, smart people or whatever. You have to organize this knowledge in some sort of system, whether that's an

Evernote file or physical note cards or whatever. If you're not recording this knowledge in some way, chances are it's just going in one year and out the other. And so I found that as a writer. I'm always accumulating this knowledge. And it happened that like, and originally there's a stoic exercise called Turning the Obstacle Upside Down, just to illustrate this.

And I read it in a book called The Inner Citadel by Pierre Hadoe, who's this great French philosopher who had written a lot about the Stoics. And I wrote this thing about, you know, it's like turning the obstacle upside down, like interesting idea or something like that. And that became a note card that just went in a general box I have of note cards I like.

And around the time that Trust Me on Wine came out, I was thinking about what I wanted my next book to be and how I would sell it and blah, blah, blah. And I went through these note cards, and I found that note card, and several other note cards that were more or less around that same idea, the idea of turning a negative situation into a positive. And it was like, boom, that's my next book.

I know this is my next book. This is perfect. And so you and I wouldn't be talking if I hadn't written that down from a book that I read in, you know, 2009 or whatever. That's awesome. I love it. One more question, man. When you hear the phrase learning leader, what's the first thing that pops into your mind? I mean, to me, it almost feels a little bit redundant, right?

Like, is there any way that someone is a leader if they're not learning more than other people? You know, a great one of my mentors, he told me that you have to read to lead. lead, right? And he meant this in both ways. Like, to be a leader, you have to read a lot, but also he meant like what your reading has to sort of be stretching you, right? Like, you have to, you have to be reading above your level, essentially. You can't just read a bunch of books that tell you what you already know. You have to be reading books that are difficult in a sense. And so, I mean, to me, the words have very synonymous definitions to me. And, and, and, and, And I cannot, I would say, and I've heard someone else say this before, too, so I'm not original

in it in any way. I've never met a really smart, successful person who doesn't also read a lot. Like, I don't think I've ever met one. And even when I find out, like, oh, they don't really, they say they don't read a lot, it's like, oh, they listen to audiobooks, or, oh, they used to read a lot. Or, you know, like, I've seriously not found a single exception to that rule. Completely agree. This has been awesome, Ryan.

Thanks so much. Where can everyone go to find you online? Ryan Holiday.net and then I'm just Ryan Holiday at Twitter. Perfect. Well, thanks so much again for being here, man. Like I mentioned earlier, I definitely want to keep his dialogue going as we both progress because I'm fascinated by your work and I'm really appreciative of it, man. Awesome.

Yeah, we'll talk again. We'll talk again soon. I really appreciate you having me on. Sounds good. Thanks, ma'am. All right. Bye. This episode of The Learning Leader Show is over, but we have plenty more to keep you locked in

until next time. Head over to learningleadershow.com for more information and to request your favorite entrepreneur, CEO, world class athlete, or anyone else that inspires you. You can also talk to Ryan directly by reaching out to him on Twitter at Ryan Hawk 12. Thanks again and we'll see you next time on the Learning Leader Show.