Ryan Holiday

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story  / Koko Ntuen

photos / courtesy of Ryan Holiday

In the world of the internet celebrity Ryan Holiday is the smart and handsome type, like the Arthur Miller to the girl who uploads YouTube videos of herself naked and eating ice cream. His website Ryanholiday.net are musings and self professed meditations on strategy and life in which he suggests books that you should actually read, makes honest observations and discusses things that peak interest on a level that is not superficial. His honest no frills vernacular have made him a bit of a muse in the marketing and writing world, not to mention the corporate world where his wunderkind status landed him gigs repping multi-million dollar clients like American Apparel and Tucker Max. Ryan has been on everyone’s radar since the announcement of his $500,000 book deal made the rounds of every major news outlet around the world. We took time to talk to Ryan about his new project and ask him the questions everyone was dying to know, well, at least we were!

How did you get your book deal?

I went about it a little differently than most people. In the last 2-3 years I had gotten a handful of book offers based on my site, but I turned them down because I felt like I wasn’t ready (really that I just didn’t know if I had anything to say). With this book, I decided I HAD to say it and I wasn’t going to worry about getting approval from anyone first. So I wrote it, floated the expenses of writing myself and then found an agent to sell it. My agent is Steve Hanselmen who I met through Tim Ferriss. He’s Tim’s agent, Peter Gruber’s agent and has done a bunch of big books. We went out to publishers, the book was going to go to a bidding war–which I had anticipated–but Portfolio/Penguin wanted it badly enough that they put in a pre-empt offer to take it off the table.

Can you give us an insiders tip of what the book will be about? Tell us a secret?

Let’s just say it is a book about my experiences and inner workers of the modern media and unlike most of the books with “Confessions” in the title, I explain exactly what I’ve done, how to do it and to protect against it.

What was your response to the media frenzy you created when it was announced that you got a half million dollar advance?

It’s been a weird experience because I’m usually the one creating media frenzies for other people. I caught myself only skimming the articles as they came out, figuring it was the same old tired blogging trope–like I do with my clients–and then I thought, oh shit this article is actually about me. I don’t know why it surprised me because it shouldn’t by now, but I was caught off guard by how LITTLE work anyone did. I know most of the bloggers who covered the announcement, and I think two bothered to email or call me to get my take on it. Two–out of 30 plus outlets that picked it up.

How did your family react?

Let me put it this way: Everybody is a lot nicer to you when they hear in the news that you signed a half a million dollar book deal.

What is your relationship like with Jezebel.com?

My relationship is the same one they have with everyone: I am not a human being nor is anyone else, we are vehicles to generate pageviews with. (That is, posts that drive clicks, comments, links from other blogs, outside press coverage) Whatever treatment will generate the most pageviews and generate them most cheaply is the one I get–and this is not unique to me, it’s how it works for whoever they write about. Some days that will be humor or snark, some days anger, others it will be self-righteousness or completely fabricated lies. In every case, it will be completely mercenary and insincere. People will be mislead, the blog and the bloggers will be enriched. That’s the system.

How did American Apparel approach you to work for them?

One of the people I work for is Robert Greene, the genius behind The 48 Laws of Power. Robert is on the board of American Apparel and has been an advisor to Dov for a long time. Dov heard of me through Robert and I came in to fix some online problems in the company. I was walking with Dov in the factory one day, and I remember he stopped in the stairwell and looked at me and said, “Ryan, this is a half-billion dollar company. You need to work here.” So I did.

What was it like the first time you met Dov?

Like most people, I was summoned to The House. (his mansion in Silverlake) He asked my advice on some stuff, and we ended up talking for most of the day. I went to the factory downtown the next day and toured it and ended up catching Dov standing on a table giving a speech to about 1,000 sewers about the mission of the company. He was crying and they were crying and the translators translating it into Mandarin, Korean and Spanish were all crying. And I was like, fuck, this is not like any other company on the planet. How could I not be a part of that? Particularly when nobody had any clue that this was going on and how special it was.

What are good tips to market your brand? Do people ask you that all the  time?

Marketing your brand is about knowing what you want to tell and who you want to tell it to. If you know who you are and who you want to reach, how to say it extends fairly naturally. The problem is that most companies are too busy, too fake or too self-absorbed to figure out these parts of the equation so that A) pay a firm way too much money to do it for them B) say nothing that no one cares about. I only work on projects that I have something to say about, believe in the brand or where I feel I understand the product better than the creator.

When did you start writing?

I met Tucker through writing and that’s when I realized the potential it had for me. I wrote an article about him for a newspaper in college and it turned into all this. Sometimes it doesn’t seem like much and it’s not like I’m great at it but people who can use words to communicate ideas have access to a power that most of their peers don’t. It’s been my asset at all the companies I’ve worked for and the people I’ve worked with, so after that interaction with Tucker I sat down and made an effort to cultivate it as a skill. I think reading teaches you to write through osmosis.

What did you think you would be doing for work when you were younger?

I don’t know if I ever really thought about it. If I had there is no way I could have predicted this. It didn’t exist.

When is the last time you spoke with Tucker Max? Do you ever sense competition from him?

Competition from me? Yeah right. First off, I don’t think he has ever seen himself in the same league as anyone else so there’d never be that problem, least of all with me. But he and I are totally different personalities, we live our lives completely differently but that’s why we have always gotten along well. We hung out a few weeks ago in New York. I think he’s the only person I know who owns more books than me.

How do you like LA(California) vs LA(Louisiana)? What the main difference?

I needed to move out of Los Angeles so badly. I was just so tired and sick of it. Everything about L.A is broken and not what it could be–how can a city that very intentionally embraced the car and forsake all other forms of transportation have such horrible roads? How could a city with so many sports teams, professional and college, have basically not be into sports? How could a city known for it’s awesome weather basically be unbearable when its hot and shut down when it rains? Ugh. On the other hand, I love New Orleans. The roads are awful here too, but a least there is a reason. And at least the people are nice and are happy that you’ve moved to their city. When you’re sitting on the porch of a two hundred year old house, underneath two hundred year old oak trees and watching a street car pass by that’s been running since 1850, it’s hard to get too upset about things. You sort of feel put in your proper place. I miss Mexican food and Costco and that’s about it. (that being said, there is a big difference between New Orleans and Louisiana)

What sites do you go to everyday?

I like to read through a combination of RSS and Instapaper because I think it insulates you a bit from the incessant pinging and ruthless competition of most of the web. You want to read sites that care about deserving your trust, not blogs that exaggerate and distort because they need their posts to go viral. Some good writers I like: Felix Salmon, Tim Feriss, John Robb at Global Guerillas, Romenesko, Jason Hirschorn’s Media Decoder, Seth Roberts, Andrew Potter.

What music are you listening to right now?

I have horrible taste in music. So for that reason I am unable to admit any song titles, but I am about 150 consecutive listens on the same song.

Tell us about your first kiss?

I think it was in a movie theater but I don’t remember honestly.

What do you see yourself doing in 10 years?

Writing more books hopefully.

Whats the biggest perk of being you?

I write books off on my taxes.

What do you think of Ladygunn?

Ladygunn is great. The girls in my office at American Apparel are always sending me links.

How many hours do you spend on the internet a day?

A lot less since I moved out of LA. 3-4 hours a day. I try to check my email only a couple times and I have gotten better and doing things that don’t NEED to involve the computer, away from the computer (like taking notes or outlining something) and that cuts down on needless Internet time.

How many books on average do you read a year?

I’ve never counted but somewhere between 200-300.

What is the book that best sums up our generation?

I talked to Tyler Cowen about this once, we were trying to figure out which book they will make students read about for this era. My choice would be Fight Club, maybe something by Bret Easton Ellis. I’m not sure if the right book has been written yet.

What is the craziest response you got from a blog post?

Death threats. Naked pictures. Like 100% from crazy dudes, unfortunately. The guy that was arrested for stalking Ivanka Trump used to email me these two or three thousand word letters multiple times a day about leading a revolution or how he was the messiah. So probably that.

What is your celebrity crush?

No crushes, only revulsions and I think we can all agree that the list is topped by Fergie, followed not far behind by all the Kardashian sisters.


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