Ryan Holiday describes how curiosity and unpaid work led to opportunities: he helped a blogger for free, then worked as Robert Greene's research assistant without pay, eventually becoming director of marketing at American Apparel. He argues that genuine value and following interests matter more than networking strategy.
Hey guys, Ramit Sethi here from I Will Teach youh Be Rich and Ramit's Brain Trust. I just wrapped up an interview with my friend Ryan Holiday. He's one of the most well read people I know. He actually reads more books than anyone that I know. But more Importantly, by age 21, he was the director of marketing at American Apparel. Soon after that, he wrote a very popular book on media manipulation, including how he manipulated his way into appearing in places like the New York Times. He actually pulls back the veil on major media and shows what's really going on, including how you can be a part of it. And in this conversation together, we're going to talk about career decisions, overcoming fear, and how you can integrate information from all different kinds of sources, including how he does it every single day. Check out the clip.
I'm Ryan Holiday, author of Trust Me, I'm Lying, Confessions of a Media Manipulator, Growth Hacker Marketing and the Obstacle Is the Way.
Okay, so you said that successful people know other successful people. So you kind of make your way into Tucker's world, right? And he starts to trust you and you guys are working together. How does it go from knowing one person to knowing all these other people?
Yeah, so Tucker had, he had like a very popular website, so he was helping other authors do the same thing. And so one of those authors was Robert Greene, who he had been a big fan of and I was a big fan of. And I remember there was something with Robert's website like I had an idea or a suggestion and I said, can I do this? And he was like, yeah, I'll connect you with Robert. And then I just started sort of doing the same thing for Robert. And Robert is a multi time bestselling author. He's sort of hugely successful. But his first book came out in 1998, so before blogs, before. So this stuff was very new to him. And, and my, like I had, I was being a huge fan of his material. I felt like more people deserved to know about it. And I was, I had ideas to show them how to do that.
Now Robert Greene, famous for the 48.
Laws of Power, Correct the Art of Seduction, 33 Strategies of War. I think he sold like several million books all over the world. And he writes about like really deep strategic thinking and like power and relationships. And so it was not only that I was a big fan, but I felt like I could learn from this person. And so, you know, I was just helping out on his website, sort of biding my time I guess. And he as a Reward. The two of them agreed to, like, take me out to lunch or something. Like, I never met him before. I'd only talked to him over email and on the phone. And we went to lunch. And Robert was. I remember Robert came late and he was fried and exhausted. He was working on this book. He was writing a book with 50 cents at the time. And this whole position was unpaid for me. And he was exhausted with writing this book. And he was like, all these research assistants that I've been working with have been total garbage. It's not working out. They can't find me what I need. And I was like, well, look, I've read every one of your books. I looked for examples that would be good in your books in my spare time. And I just don't tell anyone about. I've been doing the job that you're describing and, and not telling you about it for the last three or four years. I would do that for you in a second. You don't have to pay me. And I remember he said, nobody works for me for free.
It's a series of small, systematic and strategic steps that you took that connected you to this person, added value, connected you to the next person, added more value, et cetera.
Sure. But what I also think people miss is I wasn't doing that because I really wanted to work for Rock. I wasn't doing it as part of some strategy. I was doing it because I was genuinely curious and it was satisfying some urge that I had. Right. And so when people. I wasn't forcing it because it was the other way around. And I think a lot of people look at this stuff and then they try to force it into something that's not theirs, when really they should be looking at whatever thing in their private life that maybe they're a little bit embarrassed about that actually. They're like squirreling away and doing this sort of hidden work about because they genuinely care. That's where you're gonna get the most bang for your buck. Because like the cliche, it didn't feel like work to me. Like, I felt like I was getting something out of it.
Okay, so let's fast forward a couple of years. You end up working at American Apparel as its director of marketing.
Yeah.
Which is a very senior role for anyone, particularly a 21 year old.
Sure.
How'd this happen?
Well, first off, it's a very untraditional company, but we were talking about successful people, knowing successful people. Robert Greene is on the board of American Apparel. So. And he's been a board member since before it was a publicly traded company. And so, you know, I'd been working for him. I'd been doing all this stuff. I sort of had shown that I had an understanding of how this Internet stuff worked. And there was some problem that came up in a board meeting, and Dov was like, what should we do? You know, like, CEOs go to board members and ask for their help in solving a problem. And he was like, I think you need to talk to this guy Ryan that's been working for me. And so I went to Dov's house, and then I went to the factory, and I was just sort of blown away by this whole thing that I'd never really seen or knew much about. And I remember we were walking through, and he was like, I think you can help me with this problem. And he's like, look around you. This is a billion dollar company. Do you want to keep doing what you're doing, or do you want to come work for me and do something awesome? And I was like, yeah, sure, that works. And so I started, but I didn't have a role. I remember I didn't have an ID badge. I was very like. I was sort of like, CEOs will hire employees just to sort of like, audit and mess around in their own company. So my job was to sort of find a role for myself. And their marketing stuff was all spread out over different departments. It was a total mess. And I ended up building the marketing department, and then the title became mine because there was no one else to fill it. Sa.
