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Ryan Holiday SM 134 Transcript EPISODE 134 [INTRODUCTION] [00:00:30] FT: Welcome back to So Money everyone. Happy Monday! Hope your weekend was fantastic. I'm your host Farnoosh Torabi. We're gonna kick off the week with a very, very cool guest, Ryan Holiday. He's a thought provoking media strategist and bestselling author of three books, most recently, "The Obstacle is The Way: The timeless art of turning trials into triumphs." He has been responsible for a number of manipulative stunts and media controversies, and he's been accused of actually being a media manipulator which he writes about in his first book, "Trust Me, I'm lying." And he's only in his late 20's. After dropping out from the University of California at 19 to apprentice under Robert Greene, author of "The 48 Laws of Power", he went on to advise many bestselling authors and multiplatinum musicians, including 50 Cent and Tim Ferris. I actually had the honor of interviewing Tim earlier this year, check out episode 60. Ryan also served as director of marketing at American Apparel for many years where his campaigns ended up being used as case studies by Twitter, Youtube, and Google. He was written about in Adage, the New York Times, Fast Company. Ryan now works as the media columnist for the New York Observer, and his work has appeared in Forbes, Fast Company, the Huffington Post, the Columbia Journalism Review, and Medium.com. Several takeaways from our interview. It was such a fascinating conversation. We learn about Ryan's formula for creative success that let's you turn obstacles into opportunities, the value in negative thinking, why he chose to quit college - it wasn't an easy decision - and how stoic principles can vastly improve your professional and financial, and even personal life. Here is Ryan Holiday. [00:02:17] [INTERVIEW] © 2015 Farnoosh, Inc. !1 SM 134 Transcript FT: Ryan Holiday, welcome to So Money. So great to have you on the show. RH: Yeah it's really good to be on. FT: I'd love to start, just giving listeners a little bit of background about how you first started out. I suppose we could go back to when you were 19, dropping out of college. You were at UC Riverside? [00:02:36] RH: Yeah I was. I was in school, I was writing for the college newspaper, and I'd sort of leveraged it into these kind of informal mentorships with a bunch of people that I really respected and wanted to be like - mostly writers. And I Segway-ed from there into an internship with one of them in Los Angeles, then I had another internship at a talent management agency in Beverly Hills, and I also sort of thought that I might drop out of college one day, but I never really considered what that would be like. And one day one of the people I was working for said, "Hey like look, you've been doing this amazing job, we'd like to hire you right now. We don't wanna wait for you to graduate. What would you think about not going back to school?" And I sort of put my money where my mouth was, and I ended up dropping out a few weeks later, and now I'm here. [00:03:34] FT: Were you concerned about, down the road, not having a college degree would hurt your chances of getting further employment? Did you even think that far ahead? RH: Yeah of course. I was terrified. That was the main - so it's interesting. There's all these resources that help people get into college, there's very few people that help people who have decided to leave college, right? Because it's sort of this thing that you don't do unless, yeah you just don't do it. I'm sure it was terrifying for Mark Zuckerberg too. "Am I making the right decision? How is this gonna go? What do my parents think?" I was really worried that it would be some mistake that I was making, and then one of my mentors was like, "Look, when I was in college - he caught some disease, I forgot what it was, but he had a very serious illness and he © 2015 Farnoosh, Inc. !2 SM 134 Transcript spent a year in the hospital. And he was like, "So it took me 5 years to graduate from college and do you know how many people know this about me? None." He was like, "I took a year off school and it's not even visible to the outside world." And that was sort of when I realized that dropping out of college and deciding that you would never return to finish your education are two very different things, and sort of by taking it day by day was much less intimidating. And it just happened that I've not needed to go back, but I suppose I can go tomorrow if I decided I wanted to be a lawyer or something. [00:05:04] FT: Absolutely. And we should mention that when you dropped out at 19 it wasn't to go work at Starbucks, you had an amazing opportunity to apprentice under Robert Greene, author of "The 48 Laws of Power". So this was in some ways a no brainer, because the access and the experience that you were gonna get was unmatched. You're not gonna learn that in college. [00:05:28] RH: Yeah. It's funny, I wrote an article called "Why you should drop out of college" or something a few years ago, and it's like one of the top Google results for that phrase now. So I get a lot of emails at like 2 in the morning from college students who are really miserable and I feel for them. But most of the time I hear from them they say, "I don't like college, I'm thinking about dropping out." It's never, "I don't like college, but I've been doing this thing on my own, and I'm thinking about making a go at it, what do you think?" And so for me it was look, if I was graduating and I had this job opportunity, I would have considered my college experience a total success, right? It's like if you went to college to play NSAA basketball and a team wanted to draft you, you would go, "Okay, I'm gonna think about this seriously because it's exactly what I was training for." It's not, "Hey, I'm gonna quit school and then dig around and figure out what I wanna do with my life." [00:06:25] FT: And yeah, that's a really great point. I think that sometimes college is the right place for you, and for others it's not. And it's really about weighing your - exactly, if you've got a plan you © 2015 Farnoosh, Inc. !3 SM 134 Transcript wanna execute and you wanna take that opportunity, go for it. College will always be there, that's kind of the one nice thing. [00:06:43] RH: Sure, well look, I think chances are most of the people that are listening to this are not considering dropping out of college right now, but I think it holds true for a lot of different options. The thing that everyone is doing is a good default. So going to this college is a good default if you don't know what you wanna do. But you should be exploring all your other options and ideally trying to build revenue streams, or interests, or passion projects that could become potentially viable down the road. It's like, if you hate your job, you don't quite your job and then try to explore what else you could possibly be good at. Ideally you wanna use the position that you have to fund this other potential venture, and everyone knows you're much more attractive as the candidate or anything else while you still have the other job, not when you've burnt the bridges behind you. [00:07:39] FT: Exactly. Your mentor Robert Greene had a saying, and I found this on your website, that it's all material. And he basically means that everything that happens in your life can be used for something useful. What's the greatest example of this in your life? [00:07:54] RH: Yeah, I mean look, my first book which is sort of an expose of the media culture was very much a result of one of my big jobs at American Apparel, sort of dealing with a very controversial and provocative client. The way I've always thought about it is, the things that happen to you are both educational experiences and then if you're a creative person, there are also the experiences that fuel your work. There's a good saying, "Writer's live interesting lives." It's very hard to be an interesting writer if your life is boring and you haven't experienced the world because you can't communicate that reality to a public, and that's something I've always thought about. "How do I take this seemingly negative, or unpleasant, or unenjoyable experience and figure out whatever benefit is inside of it, even if it's just experiencing something © 2015 Farnoosh, Inc. !4 SM 134 Transcript miserable and channeling that miserableness into creativity." There's always something that you can get out of whatever you're going through.
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