This week, Cory speaks to author, marketer and entrepreneur Ryan Holiday, who is well known for being a controversial media strategist, particularly when he was the Director of Marketing at American Apparel and founder of creative consulting firm Brass Check Marketing. Ryan, in addition, is a bestselling author of six books, including “The Obstacle Is the Way”, “Ego Is the Enemy” and “The Daily Stoic” and has written for several of the worlds largest publications while being a media columnist and editor-at-large for the New York Observer. He has a new book out today which you can get now on Amazon and elsewhere titled “Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue”. In this week’s episode, he tells us why he left college at the age of 19, how he was then hired and mentored by prolific writers Robert Greene and Tucker Max, to landing an advisory position to American Apparel’s founder only to in only a year become its Director of Marketing. Ryan goes over his most controversial marketing campaigns, some of the best lessons he’s learned along the way and discusses his new book.
[00:01:20] Cory Levy: Thank you, Ryan, so much for joining today.
[00:01:22] Ryan Holiday: Yes, thanks for having me.
[00:01:24] Cory: I’d like to start by asking about college. I know you left college when you were 19. What events or circumstances led to making that decision, and how did your parents and friends feel about that?
[00:01:35] Ryan: Well, I’ll answer the second part first, which is that they did not take it well. “Disowned me” would probably be a slight overstatement of what happened, but we were not close for some time, and we did not speak as a result of it. My parents, I’ve realized, had come to see me not finishing college as a reflection of their parenting, so they desperately wanted me to stay in it, and I believe also with some good intentions that they were very worried that I would end up under a bridge somewhere. But that that wasn’t the case. I wasn’t just leaving college for the hell of it. I desperately wanted to be a writer. I had a job at a talent agency in Hollywood, this was in 2007. New media is very much on the rise, social media, YouTube had recently sold for over a billion dollars.
This was a unique period to be 19 or 20 years old and be familiar with how the internet works. I had this job with his talent agency that basically had offered me a full-time job if I would not go back to school. I desperately wanted to be a writer, and I had a side job as a research assistant for this author Robert Greene, who is the author of the 48 Laws of Power. I basically looked at it and said, “Look, if this is what a successful life after graduating from college would look like — These are my two dream jobs, why am I going to go back to school and then hope to get these opportunities again after I graduate?”
[00:02:55] Cory: What are some of the things that you learned from Robert Greene?
[00:03:00] Ryan: A really good mentor helps you both in personal and professional ways. I think Robert is just a very calm, intelligent, strategic person. He gave me just a lot of general insights as to life, but I would say most of all he trained me in the craft that I now make a good chunk of my living from.
He showed me how a book is made, he showed me how to research, how to find the things that go into a book. I was like an apprentice. I came in knowing next to nothing, and I left in a space about six or so years later in a position when I sold my first book to a major publisher. It was about everything you could hope for. There are plenty of kids who pay hundreds of thousands of dollars for an MFA and don’t leave with that return on investment.
[00:03:40] Cory: Did you work for him before or after he published Mastery?
[00:03:44] Ryan: I was his research assistant on a book he wrote called The 50th Law, and then also his research assistant on Mastery. I worked through the launch of that book, and I did the marketing for it, because I had since created a marketing company, so that was my period of working for him.
[00:03:58] Cory: Got you. How did you convince a successful writer to hire you? You said you came in with nothing, didn’t have much, but you convinced him to give you a chance.
[00:04:06] Ryan: I was working for another writer, his name is Tucker Max. At the time, he had both a number of really successful books and an online publishing platform like for other authors, so he ran Robert’s website at the time. I was working for Tucker, I had met Robert through Tucker. The three of us were having lunch one day, and Robert was complaining about not having a good research assistant. I was like, “Look, I love your books I know I could do this.” I was like, “I’ll work for free, I’ll do anything you ask.”
I’ve been such a fan of his books that as I read them, I then read the books that he cited in the bibliography to find the original sources of the story. I’d reverse engineered how his stuff worked, just as a fan, just trying to figure it out, so I had some familiarity with the work. I had another peer of his who was vouching for me, and then I presented it as a not much to lose scenario for him. He didn’t hire me as his full-time research assistant out of the gate. He gave me one project, I had to transcribe an interview, and I did an okay job, and then another one, and another one. With time, I had proved myself, and the position evolved and grew as a result.
[00:05:14] Cory: I know it might be hard to sum up six years into a few sentences, but what were the big takeaways from working with Robert and also working with Tucker?
[00:05:23] Ryan: I think one of the things that Robert told me, is he said, “Ryan, a book needs to be either extremely entertaining, or extremely practical.” He said most books are somewhere in the middle, and that’s why they don’t work. The idea of sitting down and going, “What role does this book play in someone’s life, and does it actually justify its expense to the reader?”
You’re asking a lot of your customer, readers are customers. A lot of authors mistakenly see themselves as simply as artists and that readers are lucky for whatever the artist creates. That’s not really the relationship at all. He really helped me understand how to make something that does a job, and then when you do that, you’re not as dependent on media, or hype, or even marketing at all to have a successful run with a book, because the book has that word of mouth at its back.
[00:06:14] Cory: What about from Tucker?
[00:06:16] Ryan: I learned a lot from Tucker. Tucker was one of the first people who I think saw potential in me, who believed in me. He told me that I might have what it takes, so I think at the very basic level, he just gave me the confidence that I needed to go out and do this stuff. I learned a lot working for someone that was controversial like him. I learned that you’ve got to know who your fans are, and who your fans aren’t, and if you have that understanding, it allows you to take creative risks. It allows you to kick the beehive, so to speak, and get things riled up. I learned a ton through both of them.
[00:06:48] Cory: For someone listening, young right now, what do you think are some of the ways one can figure out what he or she is good at?
[00:06:53] Ryan: That’s a good question — something that Ira Glass calls the taste-talent gap. I wrote about this in my book Ego is the Enemy. I thought it was interesting. One of the problems when you’re young is that you have really good taste, but you’re not that talented, so you’re often very, very critical of your own work and get really discouraged really easily, right? You know what’s good, but then what you make doesn’t measure up to that thing. In some respects, I think one of the things you’re going to be good at when you’re younger is discernment, you’re going to have good instincts, but you’ve got to find where you’re actually able to deliver the goods and where you’re able to show market improvement.
For me, I don’t think I started as a great writer, but if you look at my early writing, not only is there flickers of talent, but the pieces develop quickly, right? I think I was getting better the more I was doing it. I think that’s something that you want to see. Is there actually evidence of a learning curve? Are you stuck in some spot? The common career advice is find your passion, and that can somewhat be dangerous, right? Just because you’re passionate about something, doesn’t mean that you’re good at it.
One of the reasons that I sought out mentors whether it was Tucker or Robert is that I was really into writing, I really wanted to do it, and getting my work in front of people who could see it a little bit more objectively than me, seeing that talent, seeing them say, “Hey, there’s something here. You should continue doing this,” helped me answer the question that you’re asking me. I don’t know if there’s a hard and fast test, but one sign would be, are people who are older than you spotting something in what you’re doing? That’s a good sign.
[00:08:32] Cory: You’ve had a lot of exposure to young people. What are some ineffective things that you have seen people do?
[00:08:40] Ryan: Given that and I have written pretty extensively about mentorship, I hear from a lot of kids are like, “Hey, will you be my mentor?” I probably got five emails about it this morning. That’s totally missing how it works. It’s not this official thing. Robert didn’t say like, “I am willing to mentor you.” We had a meeting, he had a problem, I offered to audition, essentially, to do a menial task for him, which was transcribing an interview, that was my first thing for him. When I showed myself not to be an idiot, he gave me something slightly more important, and then when I didn’t mess that up, he gave me something slightly more important.
Then, in between, he would call me and ask about the work, and then maybe I would have one minute at the end of our conversations to be like, “Hey, I have a question about something.” Over time, that blossomed, that evolved into a mentorship relationship. It was not that ever officially, and it certainly started much more constrained than that. Getting these mentorships is something that you don’t demand, you don’t ask for, something that ensues, and that’s a common misperception that I see at a very alarming rate, actually.
[00:09:49] Cory: Got you. Thank you for sharing. I want to talk a little bit about Doug and American Apparel. How did you meet him and get involved being a young director in such a large company?
[00:10:00] Ryan: I was familiar with American Apparel, obviously, but Robert Greene happened to be on the board of directors. He’d been an adviser to Doug before the company went public. When the company did go public, he was asked to be on the board. As I was having worked for Robert at that point for quite some time, they needed — Doug just wanted good people. He wanted an assistant/adviser type, and Robert suggested me, and worked on a couple projects here and there and then Doug said, “Hey, I want you to come work for me.”
He didn’t have a job title, I don’t even think I had and ID badge at the company. I took a bit of a leap of faith. It too evolved. I took not a super high-paying position, again, not one with much status. Within probably a year, year and a half, I was the director of marketing. That’s how that happened for me as well. It was, again, taking a risk and evolving.
[00:10:48] Cory: What is the most controversial campaign that you did at American Apparel?
[00:10:52] Ryan: I would probably say those are slightly different questions, we did a number of super controversial things. Some of them were intentional, whether it’s, “Hey, we’re going to do advertisements with a porn star,” or we’re going to have a woman in her 60s or 70s dressed in American Apparel clothes. We’re going to do some double entendre with a dog wearing clothes. We did lots of deliberately controversial, provocative, strange things, and then some of them were completely unintentional, but once we’ve developed a profile for being controversial, everything was seen through that light.
It’d be like, somebody in the web department would send out an email that didn’t get approval, that was worded poorly, and then the next thing you know it’s national news, and people would ask me — Some people would be like, “How could you do this?” And then other people would say, “It’s so brilliant,” and I would say, “I didn’t even know this was happening.” One of my favorite campaigns was a campaign we did with a model named Jackie. After we’d done all these really sex-driven ads, one of the creative directors spotted this regal, dignified older woman walking the streets of Manhattan, and just said, “Look, I’d like to shoot you in an American Apparel ad,” and the woman just laughed, and she said, “No. I’m serious.”
We ran these ads and did millions and millions of impressions all over the world, it was a huge deal. It was provocative precisely because it was provocatively different than what American Apparel was known for. Cost effective? Sure. I think that Jackie campaign cost $3,000 all in, and then did millions of impressions worldwide. What did it drive in terms of sales, that’s obviously another question, but my thinking was always, “We have this canvas with advertisements and with the company’s platform and profile, let’s just do something interesting and cool with it.”
[00:12:34] Cory: How do you think entrepreneurs today should deal with controversy? You think, shy away from it, seek it, or just not back away when it comes up?
[00:12:43] Ryan: There are different kinds of controversy and there are different moments. Right now, we’re in a very radicalized, very hair trigger culture that it might make sense to steer away from controversy. Other times things are a bit more boring and stale and you’ve got to break through the noise.
I think generally the reason companies have to spend so many millions of dollars on advertisements, whether they’re hiring celebrities, or putting a billboard in Times Square, or running endless loops of television commercials, is because their shit is boring.
When you’re boring, whether your product is boring, whether your advertisements are boring, it costs a lot more. I think one of the reasons you tend to see smaller companies take more creative risks is that they have to, they can’t afford to be boring. If you’re a startup and nobody’s heard of you, taking some risks, doing some things that might piss a few people off, is probably a more reasonable strategy than if you’re a Fortune 500 company in the insurance business that’s been around for 120 years.
[00:13:36] Cory: What’s something controversial today that you think won’t be tomorrow?
[00:13:49] Ryan: I remember in 2008 we did a big campaign for American Apparel that was right after California had passed Proposition 8, which banned gay marriage in the state. We did this campaign, and it was, “Legalize Gay”, and we built this whole website, and we gave out hundreds of thousands of T-shirts, and we ran ads all over the country. This was really controversial at the time, and it upset a lot of people. I’m sure we lost some customers, but we gained many more. In retrospect, the company taking a stand on gay rights, particularly a company that had a lot of millennial customers, doesn’t seem that controversial, but it was at the time.
We also did a really pro-immigration campaign before that. That was controversial, but today it somehow would probably be even more controversial than it was at the time. The things that are getting attention now are sometimes very much of the moment, and then that moment passes, or sometimes they’re early to the moment and then you look back at them and you see like you predicted it when really you didn’t.
[00:14:45] Cory: Now, I want to talk a little bit about your new book that just came out, Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue. What made you decide to write it?
[00:14:54] Ryan: As a writer you’re always looking for projects that are different and exciting, that are not going to be the thing that you’ve done before. In a relatively short period in 2016, a billionaire, that would be Peter Thiel, and one of the kings from gossip media, which would be Nick Denton, independently reached out to me, and it happened that the two of them have been locked in this decade-long war with each other over what it was okay for a gossip publisher to publish, what was over the line. It ended with a 140-million-dollar lawsuit in Florida court in 2016, that Peter Thiel had secretly financed and instigated, because he was hoping to destroy Gawker. It’s just this incredible story that fell in my lap, and I said, “Am I going to regret not writing this?” I felt like I would, and so I did.
[00:15:40] Cory: Do you often use regret minimization as a tactic when making hard decision?
[00:15:44] Ryan: Not necessarily. I think it can sometimes lead you in the wrong direction, but I felt like I didn’t know if I would get an opportunity like that again. More importantly, I didn’t actually know if anyone else would get that same opportunity. I didn’t know if there was anyone with my background who could bridge these two worlds, and so it felt very meant to be.
[00:16:06] Cory: You were working close with both Peter and Nick, is that right?
[00:16:10] Ryan: Yes. I spent a considerable amount of time interviewing both of them about a whole number of things. I’m not suspecting that either of them is going to be particularly happy with the book, which to me means that I did my job well, but they’re both these extraordinarily unique individuals who have led very different, but also very similar lives that somehow got locked in this feud that neither of them could get out of, and the result was this surreal series of events, and it was in some way an honor to put it to paper. Every day I worked on it, I felt very excited.
[00:16:43] Cory: Do you think using money that take down a publication is an abuse of power of falls under the freedom of speech?
[00:16:50] Ryan: I guess I would unpack what you said a little bit. There are many ways that a billionaire could abuse the wealth that they have. They could hire private detectives to follow someone around, and then blackmail them with the information.
They could buy up somebody’s debt and foreclose on it. They could do any number of alarming or dangerous things, they could abuse that power. What’s interesting about what Peter Thiel did is that Peter Thiel found an instance in which Gawker had done something that potentially invaded the privacy of another person.
They ran a sex tape of the professional wrestler, Hulk Hogan, that had been itself potentially illegally recorded, without Hogan’s consent or knowledge, and then when Hogan threatened to sue Gawker, Peter Thiel secretly went to him and said, “If you do so, I will pay your legal bills.” That case wound itself legitimately through the legal system, and eventually got in front of a judge and a jury in Florida, and that judge and jury got to a verdict, which very few cases ever do in the American legal system. Gawker came out on the losing side.
It can’t be said that Gawker did not have a chance to defend themselves. They had many years to defend themselves, they had access to the best lawyers in the country, and ultimately it was a jury of their peers, although we could argue whether they really were their peers or not, and that was Gawker’s problem. Ultimately, a jury legitimately sat and rendered a verdict that said that Peter was right. I don’t see it as much as an abuse of power as some people in journalism have been quick to label it. I think it’s more complicated than that.
[00:18:30] Cory: What do you personally think of Gawker as a publication? Do you think they cross the line by publishing this racy stuff about personal lives?
[00:18:36] Ryan: I don’t think that was the problem. It’s not publishing racy stuff about someone’s personal life that is why they’re no longer in business. If you think about what happened with the Hulk Hogan tape, as far as we understand it, is that his friends were swingers, and he had a sexual relationship with his best friend’s wife, with their permission. But that best friend was also secretly recording that exchange. Then someone stole that tape, and in an attempt to blackmail Hulk Hogan, leaked part of it to the media, specifically to Gawker, to embarrass him into paying to get the tapes back.
Gawker ran this tape, this one that Hulk Hogan had very publicly said it was recorded without his consent, that he said he would sue anyone that published it, that he claimed to be mortified and embarrassed about. Gawker ran it, and they ran it without blurring out his genitals, they ran it without doing any research about it, they run it without asking him for comment first, they just threw this thing up there, because in some ways they thought they were invincible. They thought this was protected by the First Amendment, it really wasn’t. It’s easy to say like, “Oh, this is protected by the First Amendment,” but not everything is protected by the First Amendment.
Should I be able to go into your house and record your private encounters because you have a podcast? Where is that line? If I make a history of doing that, I have a track record of doing that — In some cases Gawker did do things like that to people who are not at all public individuals.
In Peter Thiel’s case, he’s a tech investor, they published his sexual orientation that he had otherwise intended to be private. Why is that okay? I’m not sure that it is. I’m not saying that’s not okay in every case and that Gawker didn’t also do a lot of legitimate journalism, but it recklessly played fast and loose with things that are ultimately codified in the law, and it caught up to them.
[00:20:23] Cory: From working with Peter, how do you think he views himself? Do you think he did this as a service to society?
[00:20:31] Ryan: I didn’t work with Peter, I interviewed him, so our relationship is that of a writer and source, but it was fascinating to get his view point. I don’t think he was particularly motivated by revenge, I think he was motivated by a sense of serving the public good. Of course, we could all agree or disagree with that, just like we can agree or disagree with whether a 400 million dollar donation to Harvard is a good use of billionaire’s fortune or not, but at some level it’s their money and they get to do with it what they want, and we as normal people — There’s a certain element of just you have to deal with it.
I think he thought of it as a public service. He would say in one of the interviews to New York Times that it was one of the most philanthropic things he’d ever actually done. I don’t know if I would go that far, but I believe that he believes that, which in some ways is all that really matters.
[00:21:19] Cory: What do you think drives him the most, from interviewing him?
[00:21:22] Ryan: I think he’s driven by this thought that humanity is besieged by a number of problems, social, technological and political, and that he’s very alarmed at our inability to solve them. I think he believes that powerful people such as himself — Powerful, competent people — A technocrat — is what’s required to solve them. He saw Gawker as an example of that. A lot of people complained about Gawker, but nobody thought you could do anything about it, so he was going to do something about it.
[00:21:55] Cory: What do you think of the current state of journalism in 2018?
[00:22:00] Ryan: Well, it’s not good. I don’t think anyone thinks it’s good, except for maybe some unself-aware journalist. I think journalism is incredibly important, but I think systemically it’s been undermined by its business model for the last decade or so.
The transition from mostly subscription-based journalism to page view journalism, which Gawker helped pioneer, I think it’s largely been bad for society. I think the economics of cable news have created this scandal-driven, got-to-watch-the-news-in-real-time-as-it’s-happening-or-you-might-miss-something mindset that doesn’t lend itself well to a thoughtful discussion or introspection in really any way, and then we wonder why everything is insane, manic and crazy.
[00:22:43] Cory: Are you going to be doing any marketing stunts for this book, or what’s the plan?
[00:22:48] Ryan: No. The book itself is provocative and unusual. I took an issue that’s been widely reported on, I think I attacked it from a unique angle that no one else could have done. That’s the best marketing that one can do. I’m going to obviously write about these issues, I’m going to do interviews like this, but I’m not going to run naked down Wilshire Boulevard or something to get people to look at me. I don’t really need to do that at this point.
[00:23:11] Cory: What do you wish you had started doing or done much earlier in your life? Specifically, actions or activities with compounding effects?
[00:23:20] Ryan: I wish I had started journaling earlier. In some respect, I’ve basically been blogging since the day I graduated from high school, so I have some written record of what I was thinking about what I was doing. I wish I had started journaling and I wish I had made it a more integral habit into my life earlier than I started a few years ago to really buckling down and doing it, and it’s made my life better. It’s helped me work through difficult issues. It’s also created a bit of a record of my thoughts and experiences in a more private way than my public writing, and I wish I’d picked that up sooner.
[00:23:52] Cory: Do you journal every single day? Is it in a Google doc or a physical notebook?
[00:23:56] Ryan: I actually made my own journal and published it based on one of my books called The Daily Stoic Journal. I journal in the morning. I do a preparation for the day ahead, the theme I want to be thinking about, that I need to know about, and then I review in the evening how — not only that theme, but how I’ve actually done with respect to that so I do it twice a day.
[00:24:16] Cory: What’s a life hack that very few people know about that you do?
[00:24:20] Ryan: I don’t think it’s one that very few people know about, but I would say that a stable, committed long-term relationship is about the best productivity life hack you can possibly come up with. I hear entrepreneurs say, “I don’t have time for a relationship.” To me, that signifies a life that is dangerously out of balance. I think it makes them vulnerable to making poor and bad decisions both personally and professionally, and I think it also — Success shouldn’t punish you with loneliness. I would say that I’ve been with my wife since I was in college. We didn’t get married until much later, but it’s certainly the best life hack/life decision that I made.
[00:24:56] Cory: On that front, is there anyone you want to thank?
[00:24:59] Ryan: I wouldn’t be here without Tucker taking a chance on me, Robert Greene taking a chance on me, Doug taking a chance on me. My publisher took a chance publishing this very unusual book that I published when I was 25. My agent did the same thing. I’m the product of people taking these chances. I have good relationships with some of these people still, not so much with others, but that gratitude is something I think about with all of them on a regular basis because even when things change or evolve, we’re still a product of the initial gift that we were given from those people.
[00:25:30] Cory: How did you get chance versus somebody else? Do you think you can distill that down into —
[00:25:38] Ryan: Sure. Why does someone bet on someone, right? I think it’s a couple of things. One is, do you actually have some raw goods. A baseball team isn’t picking you if you cant throw a fastball or run to first base real quickly. You have some actual raw athletic talent, or coding talent, or writing talent, or picking stocks, or whatever it is. You’ve got to have some raw talent. You have to be willing to work hard.
This was the most important thing in the world today. I was willing to put in tons of work. I was also really eager to learn so they would give me one thing and I would come back with 50 questions and I’d want to understand it and I would be learning on my own and bringing things to them That was a big part of it. The biggest one that I think the young people miss is that you’ve got to have your shit together as a human being.
I don’t mean you shower and shave or whatever. I mean the amount of young people that I get emails from where I can just read the crazy. This kid is nuts. I’m sure he is really nice. I’m sure he wants this really bad but he has not got his — He is sending off a lot of red flags. It’s usually dudes. I don’t get a lot of emails from crazy women probably because I think there is fewer of them in this sense. I didn’t ever give them the sense that I was a risk to the things that were valuable to them. That I was going to bring drama or conflict or difficulty into their life.
I was someone that they could talk to and wanted to talk with and wanted to spend time with and wanted to do well. That’s really important. Frankly I think this ties back into the long relationships thing. If your personal life is a mess, it’s going to show when you show up for work and people are going to be wary of you.
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