An Interview with Ryan Holiday

Originally published on Silicon Bayou News.

If you took Don Draper's marketing, added Theodore Roosevelt's appetite for reading history, and mixed in some Greek stoic, you'd get something close to online marketing guru Ryan Holiday.

Ryan Holiday

Ryan dropped out of college at 19. Since then he's gone on to work with best selling authors including Robert Greene and Tucker Max and currently heads up the marketing department at one of the most controversial and successful clothing brands of the last 20 years (American Apparel). And he's 24. He has a book coming out this summer.

Ryan has lived in New Orleans for the past year and Joshua Raley caught up with him for the abridged interview below. For more of Ryan's writing, check out his site.

On Marketing

Q: American Apparel stores, while very successful, are anything but proliferate compared to competitors. Did you break any rules in the marketing and ad buying game? Could you summarize the marketing strategy at AA for young entrepreneurs?

Ryan: I don't think we followed any of the rules. If I asked you to guess what American Apparel's advertising budget was, I guarantee the real answer would be a fraction of your guess. We're able to do that because we threw out all the assumptions: that a brand needs to hire an outside firm to do your marketing, retain a publicist, use celebrities or professional models, or spend hundreds of millions of dollars in advertising. American Apparel makes ads that catch your attention, that say something interesting and are worth talking about. By doing that efficiently, the company is able to pay the highest garment worker wages in the world instead of blowing it on forgettable ad campaigns.

Marketing is about knowing what you want to tell and who you want to tell it to, and doing it only in the most captivating and honest way possible. Once you know who you are and who you are reaching, the second half of that equation is all you have to focus on. The problem comes when you don't really know what you're saying or who you're saying it to. Don't advertise or market because you think that's what you're supposed to do. You'd be better off just focusing on making a special product that spreads because it is good.

Q: You've worked for an upstart and innovative clothing company and many best selling authors. Will you go into consumer goods marketing again?

Ryan: Still work for American Apparel.

On Writing, Blogging, and Finding a Creative Outlet

Q: You've recently moved to New Orleans and you're now finishing a book. What attracted you to New Orleans? Was it helpful for writing?

Ryan: I was ready to get out of Los Angeles and I made a conscious decision that I wasn't going to make this big move for only a slight change in lifestyle or scenery. That eliminated San Francisco and New York and Chicago, and left doing something totally different. It doesn't get much different or cooler than New Orleans.

Moving ended up being hugely helpful for writing the book. New Orleans has a great history of writers and I think it is a special place for creativity. I've never heard anyone talk about this, but I found that walking was instrumental in the writing process. New Orleans turned out to be a great city for long walks, even when it is hot because of the shade and big houses. I could not have picked a better neighborhood for that than the Garden District.

Q: Many young people dabble with blogs and other creative formats online. Few find the success and produce the quality that you have. Do you have any advice for finding a creative outlet and developing a distinct style?

Ryan: I think Fitzgerald said that writing isn't about saying something, it's about having something to say. I try to think about that a lot. So many kids email me and say they want to do what I do, but that's not really what they want. They want the lifestyle, but not the actual life. If they did, they would just do it. That's how I got started. It's not hard. It's so easy to sit down and write. Having something to say, or having people you identify with and want to work with? That's hard. And it takes a lot of work and thinking and energy.

In terms of style, I'm really transparent about my influences. I stole my style and my ideas from other people and other books and eventually developed my own hybrid. I read constantly. It's what made me what I am. A lot of kids email me: "Any tips for speed reading? You must be a speed reader!" I'm not, I just read a lot because it's important to me. Same goes for writing or anything that you do. Do it a lot, dedicate a lot of time to it because it's important to you, and you'll get good.

Community

Q: Any advice to the New Orleans and Louisiana business and startup community? Other regions seem to have long standing ecosystems of risk takers and industry changers. New Orleans is new to that party. Any thoughts on what we could use more of?

Ryan: I think sometimes New Orleans puts the cart before the horse. It's easier, sometimes, to talk about big grandiose plans rather than small practical ideas that would make a big difference. The paradox though is that it's the seemingly small things that will make the big things possible. A thriving tech and entrepreneur scene needs more than just seed money, it needs a well functioning city and the proper culture first, before it can thrive and create even more opportunities.

New Orleans has a lot of things it needs to address. People will probably get upset to hear this, but I get more optimistic hearing about the plans for the new Costco than I do about a lot of the other news or announcements on Silicon Bayou. Not that that stuff isn't good news, but Costco is just a basic staple of modern life at this point. Bringing one to the city will do more for people and create more change than almost anything else. If you build it, they will come. Focus on providing these basic infrastructure needs and you make the city the kind of place that is conducive and appealing to the people you want to live here.

If New Orleans can embrace the cosmopolitan, worldliness that actually has deep roots in the city's history, it would be a real energizer. One company that I really like is Naked Pizza. They filled a basic need here in New Orleans and they did it so well that it works in other cities now too. Their vision was big and local at the same time. New Orleans has so many great things that could be exported, but sometimes I feel like the bubble of the city keeps people thinking inwards instead of inwards and outwards. That's something special about New Orleans, and I wish we could see more of it. It's what will create the rising tide that floats all of the other boats.

Food

Q: On other sites you mentioned rarecuts.com (a New Orleans startup). Are you a fan? And you've written about caring about the quality of what we ingest. How do you define food quality and your own food values?

Ryan: Rarecuts is great. I go there at least once a week. I just spent a few weeks in Austin and I feel like Rarecuts is a place that would fit in well there, and New Orleans could use more of. I don't want to get too into my specific standards because I think that gets boring and really subjective, but I think about it like this: do what you can to minimize harm and use your buying choices to create positive incentives for change inside the agriculture industry. At the same time, you have to be healthy and you have to live affordably. Using those two sets of boundaries keeps me reasonable and still proud of my choices.