An Interview with Ryan Holiday


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 dropped out college at 19. Since then he’s went 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. And there’s been a lot of talk on the publishing industry blogs about the details of the book deal here, here, and here.

Ryan has lived in New Orleans for the past year and Joshua Raley caught up with him for the abridged interview below. The full interview can be found on Joshua’s blog and covers everything from food brands to working with Tim Ferriss and other best selling authors. For more of Ryan’s writing, check out his site.

Big thanks to Ryan for being a Silicon Bayou reader and taking the time for our interview.

› On Marketing

Q: American Apparel stores, while very successful, are anything but proliferate compared to competitors, did you break any rules in the marketing / 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 you 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 hire an outside firm to do your marketing (pay someone else to communication your ideas), retain a publicist (pay someone else to speak on your behalf), use celebrities or professional models (pay someone other than you or your customers as the model for product), or spend hundreds of millions of dollars in advertising (pay to blanket the whole world instead of researching and targeting). American Apparel makes ads that catch your attention, that say something interesting and are worth talking about. But doing that–and by doing it 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–how could you possible be interesting if you haven’t even taken an interest in your own message? 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. Most people are probably in that boat and that’s great. We’d be better off if they did that.

Q: You’ve worked for an upstart and innovative clothing company and many best selling authors. Will you go into consumer goods marketing again? And if so what kind of things in that space would interest you?

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 the book?

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/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. I don’t know if it would have been possible for me to write the book in the same city I had lived for so long. New Orleans has a great history of writers too 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 in, 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. They frequently lack an engaged audience and a distinct voice, maybe that’s a chicken or the egg problem. And many just fail to show up and persist. Do you have any advice for finding and choosing a creative outlet and developing a dinstinct style?

I think Fitzgerald said that writing is 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 do what I do, but that’s not really what they want. Every once in a while it will be someone like me and we’ll get along because we share the same outlook and feel the same things. But most of these other people–they want the concept of being a writer (not that I call myself one) or being a marketer or whatever. 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. Most people aren’t willing or interested in doing that.

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 about that too: “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 any thing 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 / startup community? Other regions seem to have these 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? Sometimes it feels like Louisiana is always skating where the puck was.*

I think sometimes New Orleans puts the cart before the horse. It’s easier, sometimes I think, to talk about big grandiose plans rather than small practical ideas that would make a big difference. The paradox though is that its 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. It’s hard to live in a city without one. Bringing one to the city will do more for people and create more change than anything else. Getting a Costco for example–that’s same goes, I think, for a lot of the fast/casual dining chains. Why doesn’t New Orleans have a Chipotle? BIRMINGHAM has one and New Orleans doesn’t. Or a bunch of places where you can get a decent salad for lunch? You end up spending (wasting) so much money on stuff like that in this city that it makes it hard to live here. 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. (What about fixing the speed trap camera problem as a priority? Ha!)

I’m not saying: think small. If New Orleans can embrace the cosmopolitan, worldliness that actually has deep roots in the cities history, it would be a real energizer. You’re starting to see it, but it’s got a long ways to go. One company that I really like is Naked Pizza. They filled a basic need here in New Orleans (healthy, world class pizza) 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. I really don’t mean to be negative about this at all–but how many New Orleans-themed t-shirt stores do we need? That is a lot of people competing for a small audience–it’s only thinking local. Why not think about products that scale? That can grow outside inside jokes and reach the rest of the world? In my opinion, that’s something special about New Orleans and I wish we could see more. It’s what will create the rising tide that floats all of the other boats–instead of everyone jockeying for the same small market share.

› Food

Q: On other sites you mentioned (a New Orleans startup!). Are you a fan, what do you love most about them?

In a previous post on food, you wrote “By caring about the quality of what we ingest, we opt out of brutal factory farming and toxic industrial agriculture—keeping excessive blood off our hands.” Tell me about that, how do you define the quality of a food brand? What is high what is low? How do you define your own food morals and judge or rate food companies? (ie Niman Ranch or Good Shepherd Heritage Poultry vs. others)

Rarecuts is great. I go there at least once a week or so. I just spent a few weeks in Austin and I feel like Rarecuts is a place that would fit in well that and New Orleans could use more of. Where else are you going to get Niman Ranch hot dogs or pulled pork? There’s a few other great places I put in that league: Fat Hen, Cowbell, Bucherie but not too many. 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 (meaning that withdrawing and becoming a vegetarian doesn’t help). At the same time, you have to be healthy and you have to live affordably. I feel like using those two sets of boundaries keeps me reasonable and still proud of my choices.

Editors Side Note:

* For example multiple Louisiana universities are now building and bragging about ‘research parks’ where all their intellectual property will finally get put to good use, be commercialized as businesses, and generate an economic return. I’m reading Steve Jobs biography the other day and they discuss Stanford doing the same thing… the 1950’s.