Ah. Ryan Holiday.
Douchebag. Imbecile. Pompous asshole.
Those are just the nice insults. I first ran into Ryan about four years ago and — Over the years, the number of nobody’s spewing lackluster insults at him to compensate for their own insecurities…have increased..quite a bit.
What can I say?
It’s fun to watch.
At 24, he’s bagged a half a million dollar book deal and has advised several best-selling authors and multi-platinum artists with their own media logistics. The truth is that, most people do not understand media cycles or how external events (organic and engineered) influence news propagation on the web to save their life. Ryan’s upcoming book will show you the underlying mechanics of how convoluted media politics is on the internet.
If you are interested in getting a firsthand, uncensored account of how the process works, I suggest you grab a copy of Trust Me, I’m Lying: Confessions of a Media Manipulator.
Here’s a quick introduction.
DW: I am sure you could easily recommend us hundreds of books – but, If you could recommend two or three books that you have found to be the most influential/instrumental in your own development, what would they be and why?
RH: Meditations by Marcus Aurelius is the greatest and most honest book ever written. 48 Laws of Power is the best for strategy and an amoral understanding of the world and The Great Gatsby – maybe the most beautiful piece of fiction ever written.
DW: How do you think things would have turned out for you thus far if you had not written that website review for Tucker in 2005? After all – didn’t that single event cause the domino effect of you getting your own book deal?
RH: I mean, I knew I wanted to be a writer and I was really interested in marketing and online strategy. I was going to write my honor’s thesis on that stuff anyway, so I probably would have tried to parlay that into some of the same opportunities I ended up getting through Tucker and all them. It would have been a much harder path and taken longer—that article ended up letting me skip ahead a bunch of places in line. Sometimes you get to take the elevator instead of the stairs. I was very lucky to catch the doors before they closed and get a free ride.
DW: In a world full of distractions and empty promises, what are your thoughts on finding ones purpose?
RH: I don’t think you “find” your passion. You feel it. What are you drawn towards? What do you seem to do with every free second? What are you good at? For me, I just tried to turn those things into a job. In retrospect – that was pretty preposterous..but it actually worked. Fortune favors young fools I guess.
DW: Did you ever finish college and do you think you would have had as much success had you taken the academic route?
RH: I didn’t. I dropped out the end of my sophomore year (though I was technically a year from graduation). The big myth of dropping out is that people who do it couldn’t cut it in school or hated it or whatever. I liked school, I was good at it. It wasn’t my favorite thing obviously but if I’d stayed I would have graduated with honors – left with good connections and been successful at it by any definition. Why did I leave? Because like many people who leave school I had a better option on the table — two or three in fact. I just couldn’t justify ceding them to someone else while I went back and sat in a class room and read about other people doing what I had a chance to do. That would have been hell, hell with busy work.
DW: There are plenty of reports out there about your half a million-dollar book deal – what’s your take on it? What key elements helped you get you from a 19-year-old college drop out to a first time author and were you consciously steering in that direction?
RH: My take on it is: cash the check and get back to work. Other people can speculate and chatter all they want. The book deal wasn’t my end goal, it was one step in a very deliberate path I’ve lined up for myself. I know what I have to do next and to me, I’m going to focus on that next step rather than getting all excited about having accomplished the previous one. Strategy is about flexibility combined with a firm objective. I’ve known where I am trying to get for a while and I look for options and opportunities as they come through that lens.
Dilanka’s Note: This is the official trailer for Ryan’s upcoming book:
DW: Did you deliberately engineer your critics as mere pawns in your grand media strategy?
RH: In the book, I lay it all out and admit to everything. I’ll put it this way: when people say “I hate this new thing” they are still, by default, saying “This new thing is out” and if they were going to hate it anyway, I might as well use their voice to help propagate a message.
DW: Assuming one is interested in maneuvering influential media outlets according to their own agenda, what mindset should one adopt and most importantly, how should one approach the planning and execution stages?
RH: Think about things from their perspective. Don’t just depend on the question “what would a reporter like to hear?” – though that is part of it. Think about how they see the world. What does this reporter/blogger try to accomplish every day? What are their incentives? What are their weaknesses? How do they make money? How does the rest of the world interact with them? When you can answer these questions then the approach becomes simply a matter of tailoring – of translating your story to their terms. I like to study and speak their language and that’s what I do.
DW: How exactly did your first book develop initially – and what was the writing process like?
RH: I kept finding myself turning every conversation I had with people who worked on the internet or blogged for a living into the exact same conversation: how fucked up the incentives and economics of blogging were. I found that there were these open secrets we all knew about and hated. And then when I was reading, randomly, this Upton Sinclair book about journalism in the early 1900s and I realized that none of this shit was new. So I decided to see if I could put my thoughts about it down on paper. I didn’t need the money so I wrote the book without an advance or an agent and then when I finished, I went out and sold it.
DW: Interesting…So, What is the main premise of the book?
RH: That people fundamentally don’t understand our media cycle or the forces they’re dealing with online. As a result they are whipped around and controlled by marketers and bad actors who do. I was tired of it so I decided to blow the whole thing up.
DW: Last but not least, who do you pay attention to in the media and marketing space? any recommendations?
RH: Nobody. They’re all charlatans and idiots. The bigger the following the further they are from the game in my opinion.
The following is an episode of Chase Jarvis Live with Ryan Holiday:
Ryan Holiday is media strategist for notorious clients like Tucker Max and Dov Charney. After dropping out of college at 19 to apprentice under the strategist Robert Greene, he went on to advise many bestselling authors and multi-platinum musicians. His strategies are used as case studies by Twitter, YouTube and Google and have been written about in AdAge, the New York Times, Gawker and Fast Company. You can find him online at his blog.