GE 156: Best Selling Author Ryan Holiday Reveals How He Sold 200,000+ Copies & Works with Clients Like Tony Robbins & Tim Ferriss (podcast) With Ryan Holiday


Ryan Holiday

Hey everyone, today our guest is Ryan Holiday, the former Director of Marketing at American Apparel and current Founder and Partner at Brass Check Marketing where he focuses on creative consulting, advising, and marketing. Ryan is the author of several books including “Ego Is the Enemy,” “The Obstacle Is the Way,” “Trust Me, I’m Lying,” and “Growth Hacker Marketing.”

In today’s interview, we’ll be talking about the scary risk Ryan took to drop out of school at 19 and work as a media strategist as well as a research assistant for author Robert Greene, how his role as Director of Marketing at American Apparel led to writing his first book, why his books have sold over 200,000 copies in 20 languages, and how Ryan got to work with high-profile clients like Tim Ferriss, Tony Robbins, and Tucker Max.

Ryan’s newest book “Ego Is the Enemy” came out June 14 and you can purchase it right here!

Download podcast transcript [PDF] here: Best Selling Author Ryan Holiday Reveals How He Sold 200,000+ Copies & Works with Clients Like Tony Robbins & Tim Ferriss TRANSCRIPT

Episode highlights:

  • [5:53] – Taking risks can help you level up and grow in a big way
  • [6:09] – Writing a book may be giving away knowledge, but it is also a calling card that creates opportunity for writing, speaking and consulting
  • [7:08] – Writing a book separates you from the herd in a big way
  • [7:36] – Creating a book is an incredibly challenging thing to do, because it takes months or years the progress can be discouraging
  • [8:53] – Selling a proposal, writing, editing, and marketing takes months and months of work. On top of that none of the results are certain. Don’t take this challenge lightly.
  • [9:41] – A 10,000 or 20,000 amount of books sold represents a significant number. Ryan’s book have sold north of 200,000 copies. The key is something that sells in perpetuity once the marketing has stopped
  • [11:29] – It’s not about creating a best seller it is about making something that sells for years and years
  • [11:52] – The Obstacle Is the Way was about turning trials into triumphs and became very popular with sports teams like the Seattle SeaHawks. Ego Is the Enemy is turning the obstacle into being ourselves and the way our own arrogance can hold us back from our creative work and success. Essentially, how we are our own worst enemy.
  • [12:47] – When you are young the best way to get ahead is to make other people look good. It’s not easy to watch other people take credit for what you did.
  • [15:10] – Ego manifests itself differently when you are aspiring or successful. We need to be conscious and look at things with an objective and clear eye.
  • [16:23] – Both books use stoicism to relate to modern life and a modern context
  • [16:53] – Stoicism is a philosophy that believes we don’t control the world around us, we only control how we respond.
  • [17:51] – This is a philosophy for the powerful and the powerless
  • [18:12] – Ryan has worked with high profile clients like Tim Ferriss, Tony Robbins, and Tucker Max. He got these clients by doing a great job for other clients, and now people come to him.
  • [19:41] – The majority of Ryan’s business also comes from people who had read his books.
  • [21:03] – Making a difference in the world is scary, but how else are you going to get the word out
  • [21:24] – A book needs to be marketed from a platform. Building a base before a book launches is a good strategy.
  • [22:43] – Learning to say “No” means you aren’t making your family and obligations suffer

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Disclaimer: As with any digital marketing campaign, your individual results may vary.

Full Transcript of The Episode

Show transcript
Ryan: It's not about creating something that becomes a number one bestseller in a category on Amazon for five minutes, it's about can you make something that sells for years and years. That's ultimately where the money is.

Speaker 2: Do you want to impact the world and still turn a profit? Then you're in the right place. Welcome to Growth Everywhere. This is the show where you'll find real conversations with real entrepreneurs. They'll share everything from their biggest struggle to the exact strategies they use on a daily basis. If you're ready for a value-packed interview, listen on. Here's your host, Eric Siu.

Eric: Before we jump into today's interview, if you guys could leave a review and a rating, and also subscribe as well. That would be a huge help to the podcast. If you actually enjoy the content and you'd like to hear more of it, please support us by leaving us a review and subscribe to the podcast as well. Thanks so much.

All right, everybody. Today we have a Ryan Holiday, who is the author of books such as 'The Obstacle is the Way' which I highly recommend, "Trust Me, I'm Lying', and the new book "Ego is the Enemy'. Ryan was also the former Director of Marketing for American Apparel. Ryan, how's it going?

Ryan: It's going quite well. How are you?

Eric: I am doing well. Thanks for being here. Why don't you tell us a little bit about who you are and what you do.

Ryan: That's probably my least favorite question in the whole world because I feel like I never do a good job answering. I guess I'm a writer. I've now written, this is my fourth book, and I also am a Marketing Strategist. I work for companies like Google, American Apparel. I've worked with authors like Tim Ferriss and Tony Robbins. I help people spread ideas through culture. That's what I've gotten really good at over the years. I happen to be lucky enough to get to spread some of my own ideas the same way.

Eric: You were on this crazy career path. You dropped out of school at age 19?

Ryan: Mm-hmm [affirmative].

Eric: You went to go work at American Apparel and become their director of marketing. Right now you're doing all this crazy stuff, writing all these books. Tell us about the choice that you made and all the things that have led up to where you are now.

Ryan: It was really a terrifying choice. It was the sophomore year of college. I had an internship in Los Angeles over the summer, which I really took to. My last week or two there, the company ended up getting a meeting with a pretty big band, a band that sold 50 to 60 million records. The band wanted a new media strategy. I put this thing together which people often ask interns to do. The band ended up signing precisely because of that strategy. The company was then on the hook to deliver those things and they said, "Hey. You're supposed to go back to school in two weeks. What if you didn't?"

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Right around that time I had met this author. His name was Robert Greene. He wrote a book called 'The 48 Laws of Power'. Robert was looking for a research assistant. I had these two dream opportunities pop up right at the same time. I had to ask myself, "Am I going to go back to school to hopefully graduate and get a similar job offer two years from now or am I going to jump now, a little bit before I'm ready, but could potentially change my life in doing so?" It wasn't something I took lightly. It was terrifying. It ended up working out.

I spent about a year at that agency and then I went to work as a strategist at American Apparel. I worked my way up through the ranks there. Soon enough, I was the director of marketing. It was really about taking this risk that, at the time, felt like an enormous risk, but in retrospect I could have easily gone back to school. It wasn't as if I was joining the army or something. You never know how things are going to go. You take these chances and they can change your life.

Eric: A lot of people, you go off on this trajectory. You're a Director of Marketing for American Apparel. A lot of people would say, "Okay. Let's just keep pushing. I'm going to go be a CMO somewhere else or I'm going to go start my own thing." You went down the author route. Tell us about that.

Ryan: I had been at American Apparel close to four years, and I could have started to look for a job at a bigger company. I certainly had offers and interests. I could have started my own company. What I had realized is that I wasn't going to go much further inside American Apparel. I was the Director of Marketing. It wasn't a company that had a VP or a CMO role. My direct boss was the owner and the CEO of the company, so I wasn't going to take his job. There was really nowhere for me to go. I started to get unhappy with the media environment, how it click [inaudible 00:04:48] and the way things were scandalized and sensationalized. I felt like, working for this controversial company, I had a sense of how the media worked that maybe the public didn't.

I thought maybe an interesting move for me would be to write about it. Again, I wasn't sure if it would work. It felt like a terrifying choice at the time, but I basically told the company that I couldn't work there full-time anymore. We ended up coming to an arrangement where I was an advisor. I kept my title, but I had no day-to-day responsibilities. I packed up my stuff and I moved across the country, and I sat down to write a book, which I've never done before. About a year later it came out and it sold for a pretty decent advance, and then it came out shortly after that. All of a sudden, I had this new career path that I've never really anticipated for myself. Again, it's taking these risks and trying these things that could end up leveling up for you in a big way.

Eric: It's doing those things that really helps you grow. A lot of people talk about writing a book. I'll give an example here. Joe Polish from Quantum Marketing Institute, after the interview I did with him he said, "Eric, the main thing that you have to do is you have to write the book. After you write the book it's a freaking game changer." I guess, just asking you, what has becoming an author done for you so far?

Ryan: It's funny, you think you're writing this book and you're giving away all your knowledge,

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and indeed you are, but a book also functions as a bit of a business garter. Calling card's probably a better word for it. All of a sudden you have these people that want to hire you because they read your book and they like what you had to say. My book launched a marketing company which I have to this day which does quite well. It also created an opportunity for me to write subsequent books, for me to do speaking, for me to do a lot of consulting.

Since a book requires such an up-front investment from the author in terms of time, and to do it right, it's such a difficult task. When you come out the other side and you successfully marketed it and it reaches an audience, you've proven yourself to be as a member of a relatively elite club. Obviously, lots of books are self-published these days, so it's not as elite as it once was. You have separated yourself from the herd in a major way. It's really difficult to over-estimate just what an effect a really great book can have on your career.

Eric: When you're writing a book, what actually goes into it? You talk about getting a New York Times bestseller. A lot of people are writing books and a lot of people struggle with the promotional aspect of it. I think a lot goes into it. I think a lot of people don't realize having a book author, or a co-author, or a book agent, all that type of stuff. How much effort actually goes into it?

Ryan: If it would be difficult to over-estimate the effect that a book can have on your career, I would say it's equally difficult to over-estimate how much work, and effort, and blood, and sweat goes into a book. Obviously, there's services out there. You can hire someone and they can write it for you. Our company does a fair amount of ghost-writing for relatively high profile individuals. There's firms you can hire to market for you, which is something my company does as well. To sit down and create a book, I mean to sit down and several months later have 60 or 70 or 80 thousand coherent words in the best possible order, in the most compelling arrangement is an incredibly difficult thing to do.

You sit down and it's a project with this the progress is measured in a matter of months and sometimes years. The idea that you can sit down and work on something every single day and be making no visible process is incredibly discouraging for a lot of people. If I had to summarize what goes into it, it's having an idea that is actually worthy of being a book. If you sell it traditionally it's finding an agent who wants to represent that book, it's writing a proposal, it's selling that proposal to a publisher. Then it's actually going out and delivering on this business plan that you've created, which can take quite some time. Then it's editing.

'Ego is the Enemy', which comes out now, I imagine by the time people listen to this, that book was a year of editing alone. About a year of research, a year of writing, and a year of editing. There's some overlap there, but quite a bit. Then marketing takes months and months and months of work. On top of all of this, it doesn't matter how good you do it any of those things, none of the results are certain. It's an endeavor that I would not encourage someone to take on lightly because I bled through enough of them that I know what it takes.

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Eric: The audience really loves metrics. What are some numbers you can share around you being an author, whether it's books sold, whatever it is exactly? What can you share?

Ryan: Well, books sell fewer copies than people think. There's the Dan Browns of the world that sell 10's of millions of copies. Anytime a book is selling more than 10 or 20 thousand copies in the traditional format, so that's not, "Hey I sold 10,000 copies of a book for $.99, or I gave away 10,000 copies." Anytime you're breaking the 10 or 20 thousand copy metric, you've registered as an author in the industry. You got to think about, let's say it takes the average person 10 or 12 hours of reading time to finish a book, and each book is $25. That's a significant amount of revenue and attention captured.

I think Tim Ferriss has talked about this. He's saying, "Would you want to have a million readers of your blog, or would you want to have the 1,000 people who attend TED every year read your blog?" With a book I think it's about finding the right audience, but personally my books are now north of 200,000 copies. They're in almost 20 languages. We'll see that the key for a book is can you make something that sells in perpetuity once the marketing had stopped? My book 'The Obstacle is the Way' is now comfortably selling about a thousand copies a week without me doing anything. Once a book gets to that level, it can sell for twenty years at that level. It's not about creating something that becomes a number one bestseller in a category on Amazon for five minutes, it's about can you make something that sells for years and years. That's ultimately where the money is.

Eric: I love it. Let's jump back to the books in a little bit. I do want to talk about 'Ego Is the Enemy'. Tell us a little bit about what that book is all about, and how you came about the idea.

Ryan: I wrote a book called 'The Obstacle is the Way' a little over two years ago that was about how we overcome external obstacles. It was a book that became very popular in professional sports, the Seattle Seahawks, the New England Patriots, the University of Texas Longhorns. A bunch of teams started to use the book. When I was starting to think about a follow-up, I wanted to home in on our biggest internal obstacle which would be ourselves, the way that our own ego or selfishness, our arrogance, our delusions can hold us back from our creative work or the success that we hunger for. I wanted to look at the way in which, essentially, we're our own worst enemy.

Eric: Interesting. 'Ego Is the Enemy'. Today I was listening to one of your talks about the Canvas Strategy. What's that all about?

Ryan: I'm talking about how when you're young, often the best way to get ahead is to make other people look good, or to not care about credit. To help your boss get credit, essentially. If you feel like, this is a strategy that inherently challenges the ego. For me, as I dropped out and I was working for these successful people, it's not easy to watch other people take credit for things that you did. It's not easy. I sat at that meeting when they signed that band, and I watched much older, much more well paid individuals read word for word something that I had written to sign this band. I watched this band nod in

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agreement. "Wow, that's so smart. Let's do that." I was getting paid $300 a week. I was making nothing, right? This is what one usually needs to do to get ahead. You have to subsume your ego into the work and, frankly, be willing to eat shit for a while as you prove yourself to the people who can ultimately open doors for you.

Eric: The whole concept of eating shit for a while ... The people that eat shit for the longest throughout their lives, those are the ones that are able to forego ego, right?

Ryan: It's obviously not about eating it forever and not being a doormat, but it's strategically saying, "Look, this is my plan. I know that I have to do x, y, and z to get there. If that's what it requires, if x requires me to put up with an abusive boss so I can check this off my resume, maybe that's what it is." It's about the idea that, think about someone like Darwin who spent ten years researching just barnacles to polish his theory on evolution. In fact, he only went public with it, he didn't even think he was done. He only went public with it because, ultimately, he was going to get scooped. It was this idea of being willing to essentially toil in obscurity for years and years. That's what made his discovery so profound and important. I think it's hard for young people because they're so impatient. We want to be gratified instantly. It's hard to do that.

Eric: What do you say to the entrepreneurs. Obviously, entrepreneurs, they have their own thing. I'd imagine ego is probably a big problem amongst entrepreneurs, for sure. What are some other ways to reduce that ego?

Ryan: I guess it depends on who you are and what you're doing. Ego, obviously, manifests itself differently when you're aspiring. When you're successful, it manifests itself in a different way. Now, maybe it's arrogance, or it's micro-managing, or being, Pat Riley calls this 'The Disease of Me'. A disease where ego rips apart a team that was once intent on playing together and pursuing a goal larger than themselves. The bonds begin to fray once people start arguing over who gets paid more, and who should get the ball more, and who's hogging the spotlight, or not passing enough. Ego manifests itself differently depending on where you are, but you have to conscious and make sure that you're looking at things with an objective, clear eye, and that it's not clouded by what you think you deserve, or what you want, or what you think you've earned.

Eric: 'The Obstacle is the Way' is more about Stoicism. Is that correct?

Ryan: They're both about Stoicism, but I guess what I would say is they both use Stoicism to make a point about modern life. There's lots of amazing books of Stoicism out there. I urge people to read Marcus Aurelius, and Seneca, and Epictetus. I'm trying to apply stoic philosophy along with other philosophies into a modern context.

Eric: Obviously, Tim Ferriss talks about 'Meditations' and all that. He's the one that made me aware of Stoicism. I've read into it, but if you're to define Stoicism in a simple way, what is it exactly?

Ryan: If I was trying to explain it historically, I would say it's a philosophy popular in ancient Greece, in ancient Rome, and I would go into all that, but that doesn't do a lot for

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people. If I was defining Stoicism, I would say Stoicism is a philosophy that believes we don't control the world around us, we control only how we respond. Stoicism is a philosophy that provides exercises and insights on how to respond. How to respond well to this world in which we are relatively powerless. There's a reason that it's popular with everyone from Marcus Aurelius, who's the Emperor, the most powerful man in the world, to Epictetus, who was a former slave, who was actually banished from Rome by a different Emperor. It's this philosophy that really suits itself to the powerful and the powerless because it tells us, "Hey, I'm just a guy. I didn't make this world, but I got to figure out the rules and I got to make the most of them.

Eric: Love it. By the way, everyone should go check out 'The Obstacle is the Way'. I've gone through that book. Ryan was very gracious to give me a copy of 'Ego Is the Enemy' as well. I was going through that on the plane yesterday. Both are very good, highly recommended. I want to jump back to you working with bestselling authors such as Tim Ferriss, Tony Robbins, Robert Greene, and more. How did you go about getting these opportunities?

Ryan: It's a process. I don't think I have ever sought out a single client. I had certainly done no advertising. My company has gotten almost no publicity. My clients come to me, typically, because another client said, "Hey, Ryan did a good job," or Brass Check's the name of my company so they say, "Brass Check did a good job." I think I get so much interest from young people. "I want to start a company. How do I get clients? Blah, blah, blah." What you do is you find one client and you do a really good fucking job for them.

I worked with Tucker Max who went on to sell millions of books. I've worked with Tim Ferriss who's, obviously, a genius marketer himself and has sold millions of books. I've worked on a number of other really awesome books. I picked my shots. I found projects that I felt I could contribute something to. Then I threw myself and my team into delivering amazing amounts of value. You're typically not charging very much money. Then we built a reputation as being one of the better firms in the industry. Now, people come to us and we choose who we're going to work with based on who we think we can do a good job for.

Eric: I'll speak to this podcast. The podcast brings about interesting opportunities such as speaking opportunities, or other business opportunities. I imagine books are the same way. What's one big opportunity that came your way as a result of writing books?

Ryan: That's a great question. Honestly, more than I can think of, I would say that the majority of my business comes from people who have read one of my books. It's been cool, from writing 'The Obstacle is the Way', getting to meet some of my heroes in sports. I've gotten to go to Patriot's games, I've gotten to talk on the phone to NFL coaches, it's been really crazy.

I would say probably one of the coolest ones for me is I was introduced to Stoicism when I was a student in college. I met Dr. Drew at this college conference. I asked him, "Hey, what books would you recommend?" He recommended the stoics to me. I thought that was going to be the end of our interaction. You bump into someone and

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you ask them a question. A few years later I wrote this book about Stoicism and he found out about it, and he emailed me. That was, for me, a very full-circle moment. These people influence you and then if you can make something that you can contribute a little bit to the world, you never know how that might come back to you.

Eric: The book is a medium, the podcast is a medium. I think going about these things are terrifying to do, but it's not that hard once you get going, right?

Ryan: No, no. Making your difference in the world, making your tiny little contribution, it's scary but how else are you going to make a name for yourself?

Eric: Right. Just a few more questions down here. What's the most effective tactic you used to market your book?

Ryan: It all depends on the book and the author, but I would say the biggest thing that people miss is they think that ... A book needs to be marketed from a platform. If you're a nobody, nobody's going to have you on their podcast. If you don't know who you're going to sell your first thousand copies of your book to, nobody's going to buy any copies. You have to build a base. I think my list was about 5,000 people when I launched my first book, and by the time I wrote my second book it was 10,000. Then it was probably 30,000 by the time 'Obstacle' came out. Now, it's 60 plus thousand. It's about building that audience, capturing it, and selling directly to them. That is the best way to market a project.

Eric: Tell us about one big struggle you faced while building your career as an author.

Ryan: I have a trouble with work addiction, with getting consumed with a given project or an obligation. I stress, I over-think, I over-commit myself. It's hard for me to turn off. I mean, part of writing 'Ego' was me slamming face first into that wall of having never said no to anything, just accepting, accepting, accepting to the point where I was stretched beyond any normal physical capacity. I think a hard thing for me is being able to say no.

Eric: How have you learned? That's a struggle I face. How do you say no now?

Ryan: You got to realize that you're not the only, like, I can say yes to everything if I'm just me. I have a wife, I have employees, I have family members, I have friends, I have work, my writing which I believe in. If I say yes to everything, they suffer. I don't mean that in a self-absorbed way like I'm so great, but by getting married to this woman, I've promised her a piece of my life. By taking money from clients, I've sold them some of my time. If I just say yes to everything else, then I'm being dishonest. I'm selling things that I don't own. It's been important for me to realize that there are consequences and costs to saying yes to everything. It might be harder in the short-term to say no, but it's ultimately the right thing to do.

Eric: From a tactical perspective, sometimes I feel like a dick for ignoring people, but when you get a lot of emails that's what happens. What's a nice way for you to say no?

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Ryan: You don't have to respond to every email. I think it's important that people realize that. The explanation I just gave you. I give to many people. I say, "Look, I would love to say yes, but I'm not able to. I have too many other commitments and it wouldn't be fair to those people that I committed to before you for me to say yes." I'm honest. Say someone wants to have me on a podcast they're thinking about launching. I say, "Look, I can't take a chance on this right now. Come back to me when you have established yourself or you have something going, and I would be happy to consider it then." The reality is, most people never do that. Part of it is pushing the thing back on the person who is trying to impose on you, and letting them filter themselves out.

Eric: What's one piece of advice you'd give to your 20 year old self?

Ryan: Related to what we're just talking about, I'd say, "Fucking relax, man. This is not the most important thing in the world. You've got plenty of time. You're not doing anyone, especially yourself, any favors by being this tightly-wound ball of stress who thinks that if you don't do this the world is going to collapse."

Eric: Which book has made the biggest impact on your life?

Ryan: There isn't one book, but I would say 'Meditations' by Marcus Aurelius was probably the single most influential book in my life and it's the one I talk and write about the most.

Eric: Great book. Is that a book that you come back to and re-read time and time again?

Ryan: I have a copy of it next to me on my desk. This wasn't planned. I looked over and I have it here.

Eric: Well, Ryan, this has been great. What's the best way for people to find you online?

Ryan: is my website. I'm @ryanholiday on Twitter and Instagram. On my site I have a book recommendation newsletter if people want book recommendations.

Eric: Everyone, make sure you check out 'The Obstacle is the Way' and then get 'Ego Is the Enemy'. Ryan, thanks so much for doing this.

Ryan: Thanks for having me.

Speaker 2: Thanks for listening to this episode of Growth Everywhere. If you loved what you heard, be sure to head back to for today's show notes and a ton of additional resources. Before you go, hit the subscribe button to avoid missing out on next week's value-packed interview. Enjoy the rest of your week and remember to take action and continue growing.