We first heard about Ryan Holiday through his book Trust Me, I’m Lying: Confessions of a Media Manipulator. In it, Ryan shares a story about the time Tucker Max – who’s written articles for us in the past – asked him to create some controversy around his upcoming movie, I Hope They Serve Beer in Hell.
Long story short, Ryan defaced some billboards advertising the movie in L.A. (billboards he had designed and paid for), took photos as if he were a random passerby named Evan Meyer, and sent them into popular media outlets with the note “Good to know Los Angeles hates Tucker Max too.” In under two weeks, students across the country were seemingly inspired by the (fake) billboard statement and began protesting the film, certain cities banned the film’s advertisements, and the movie gained of basically free publicity.
In addition to being a master media manipulator, Ryan also worked as American Apparel’s Director of Marketing, founded the creative advisory firm Brass Check, and authored multiple books, including the popular Growth Hacker Marketing.
Needless to say, we’re huge fans of the guy and think he’s a total legend. So, I asked him some questions, which he kindly took the time to answer. All are presented unedited. Enjoy.
You’ve been written about by top publications and employed by top authors/companies. What’s one thing that you have that other people don’t?>
I will try not to walk into this trap considering I just wrote a book about not believing in your own specialness. Hopefully I won’t also give one of those lame job interview-esque questions (“My flaw is that I work too hard!”) I think what I bring to the table is that I enjoy my craft. I fucking love writing. I love finding ways to tell stories (that’s my marketing job). On top of that, I think I am good at stealing information from good sources and putting it to use (As Austin Kleon says “steal like an artist.”).
Basically, I’m willing to grind it out because I take pleasure in the grind – but not so much that I’ll work at something that isn’t working. I’ve gotten good at seeing things strategically, coming up with new angles and connections and ways of looking at things. That’s what moves the ball forward. But ultimately, those breakthroughs come from the fact that I’ve been at it and stayed at it for a long time. When I go for a run on a rainy day or when it’s a 100 degrees out in Austin, I never see anyone else around, you know? But I’m there, in the same way I am there are my desk writing even when there might be more fun stuff to do.
Here’s an easy follow to that one– secrets to your success?
I wouldn’t call them secrets but there are few things that have certainly helped. I’m a college drop-out so it certainly wasn’t my schooling. But when one makes the distinction between schooling and education, then books are a great equalizer – maybe even more than that, like a secret advantage. I prefer books to articles, to blogs, to videos, to TED talks to basically anything (except first hand experience, obviously). If I don’t have a book in my hands, I feel like I’m wasting time. If I’m not reading a physical book, I save pretty much every article I think I want to read to Instapaper and read it later on my phone away from the computer, preferably offline.
The other thing is that in my career I have worked as a Hollywood executive, I was also a director of marketing for American Apparel, I was a research assistant to Robert Greene and I am still writing and consulting with a lot of clients. At one point I was doing a lot of these things simultaneously, going from one office to the other. And what I’ve found is that being really good at one thing is incredibly hard. Being really good at two things seems impossible. But pursuing these tasks simultaneously can actually make them easier. Insights from one field transfer across. So that’s been another thing.
To give you a very recent example to illustrate this, Steven Pressfield just released for free this fantastic book that pretty much shows how the experiences he had in different fields (advertising, screenwriting, etc.) all transfer across and you start to see patterns and principles and you can apply an insight from one place to another. In my case, my different experiences were all done in parallel and not sequentially which is not the usual path for most people.
Then there were all the people who have mentored me (they know who they are) who taught me how to think, taught me how to create my books and helped me get book deals, walked me through my jobs, helped me when I messed up, showed me how to be a man and generally gave me tons of their valuable time when I asked for it. I would not be here if people like Robert Greene or Tucker Max hadn’t taken me under their wing and mentored me.
I’ll give you one more secret that I think has been responsible for my success and it might seem like a counterintuitive one: my wife. A lot of entrepreneurs seem to believe that relationships and careers are at odds with each other. I think they believe that relationships tie people down, that they are the death knell for creativity and ambition. But from my experience, I would say it’s actually the opposite. My wife and I have been together since college and if it wasn’t for that relationship – and her advice and help – I would have spun off the planet. Having someone you can rely on, lean on, have private space and time with, it’s essential when you’re chasing a big or public career. It’s 10x harder to do it alone. I wish more people would put the time in. I’m better off for having done so.
You mention surrounding yourself with the right people. Who are some people you choose to spend time with and how have they impacted your life?
Yes, of course. So Robert Greene would be an obvious example. We talk regularly and he has been one of the most influential people in my life. Like I said in the answer above, if it wasn’t for someone like Robert who has taken me under their wing and mentored me, I wouldn’t be here giving this interview.
But mentors don’t always have to be people who are alive or that you actually know. At the time I was training directly under Robert, everyday I was also reading blogs and articles from some of people like Mark Cuban and Tyler Cowen. It’s crazy if you think about it. When else could someone get access to a billionaire like that? Tyler Cowen teaches at a school I never could have gotten in, but his stuff was available to me, a random kid. I remember one day, I was having trouble with some bullshit at work and I emailed a question to Chris Anderson, who was then the editor in chief of Wired. He responded like ten minutes later. So I think early on I was surrounding myself with good people…even if they had no idea.
And today, with podcasts, you can be listening to some of the smartest people having conversations for hours absolutely for free. And you can usually ask questions online before shows. You can ask questions in AMA’s. It won’t be a fully elaborate answer usually but it can give you the right direction.
Goethe says, “Tell me with whom you consort with and I will tell you who you are.” These don’t have to be face to face conversations you know. He also says, “If I know how you spend your time then I know what might become of you.” So it’s also what material you interact with, who you hang out with. All of that adds up to who you are and will be.
Have you ever done something detrimental to your career? What was it and what did you learn?
It was partially a mistake and partially just something that happened to me but I learned a great lesson in a few senses from it. In 2008, when I worked at American Apparel, a former IT employee broke into my company email and leaked a bunch of private correspondences to numerous media outlets. Information from benign, personal emails between the CFO and myself were printed in outlets like Gawker, CNBC, The New York Post and others, and spun by reporters to create what looked like a bankruptcy crisis, damaging the company’s reputation and stock price. It happened the night of Christmas Eve and I was maybe 21 years old. It did more than just ruin some time with family. I was convinced in that moment that my career was going to end.
I cannot express the violation of privacy I felt. But I remember calling Dov Charney, American Apparel’s founder that night to apologize and explain. He said to me something like: “Look, we all say things in email that we wouldn’t want other people to see or hear. Particularly your generation – you use email instead of the phone. I’m not going to fault you for anything that’s in there.” I’m very grateful for that understanding – my entire life might have turned out differently without it.
Obviously my email should have been much more secure and that was my fault. I had told myself up to that point that nobody cared about what I did and so I could be lax and loose with what I did. That was a big wake up call. But more importantly, it was a great lesson in leadership that Dov demonstrated to me. People mess up. Shit happens. Forgiveness and empathy are usually better strategies for developing loyal employees than punishment and yelling. I would have walked through fire for the guy after that.
What’s a typical day look like for you?
In terms of productivity and daily routines, one of the best pieces of advice I’ve gotten comes from Shane Parrish at Farnam Street. It’s simple: If you want to be more productive, get up early. So I get up around 630am and I have one other simple rule: Do one thing in the morning before checking email. It could be showering, it could be going for a long run, it could be jotting some thoughts down in my journal, it’s usually writing. I try to help my wife with farm chores, but she’s a lot better at them than me. Most mornings I try to write for one to two hours before I start the rest of the day (and the to do list I made the day before). So that’s in the morning.
Then there are also three specific things that I try to do every day no matter what. I talked about reading earlier in the interview. I would pick up a book every day. Even for just a few pages. In books we have some 5,000 years of recorded knowledge. As Emerson says, every book is a quotation – of other books, of experience, of the humans and civilizations that came before it. How could you not expose yourself to this? The other thing is exercise: A lot of people like meditation, but done properly, exercise is meditation. And it is healthy. For me that’s running and swimming which I do in the afternoon.
And lastly, I go for a walk which isn’t this the same as exercise. Exercise is designed to stimulate the body, walking to stimulate the mind. And I try to take all my calls while walking.
So then what’s your sleep schedule look like and how does important is it in your work/life balance? Is it a routine 10 pm-6 am every night or is it a play by ear kinda thing?
Yes, you nailed it actually. 10 to 6 is about right. Obviously, this doesn’t happen when I am traveling – all bets are off. What matters to me is that I get my work done and get my exercise in. And I will trade sleep for exercise, but usually not for work. When work impedes on sleep, poor planning is to blame – I don’t see sleep deprivation as a sign of impressive willpower. Disorganization is why I think most people don’t have time for sleep (obviously kids are a game changer, so I am making no judgements there). The human body needs its rest, it needs to replenish and burning it out is, as Schopenhauer pointed out, a ridiculously short-sighted strategy.
And to go back to your earlier question about day-to-day stuff, sleep is one of the most important parts of my work routine, period. If some emergency interrupts, I work around it and I bump less important things until I get caught up. I get my 7-8 hours (unless jet lag intervenes). I hate being tired and I don’t think I do good work when I am. I also hate the rush of adrenaline that comes from running on fumes. I feel like this is ruining the engine with some toxic substance.
Marketing is a broad term and, as someone who’s been known for publicity stunts and media manipulation, I’m curious what “marketing” means to you. What’s the most important thing people should consider when marketing a business, a product, or themselves?
I like the definition I came up with in Growth Hacker Marketing: Anything that gets or keeps customers is marketing. That’s it.
And what people should focus on? I think the framework that I outline in the book applies to just about any business. Step one is achieving product-market fit – knowing your product satisfies a clear need for a well-defined audience. The second step is finding your growth hack(s): You want users, customers, clients. Your job at this point is to get growth, through any means possible. (Some of the cliches are Airbnb piggybacking on Craigslist or Uber giving free rides during SXSW but it can be really anything that puts asses in seats). Then, you need to think how to get your users to help you in your growth – this is the viral component.
You need to create strong – and I emphasize strong – incentives, for your users to become your referral engines. Sharing buttons won’t cut it here. And the last step is making sure you retain those customers. It is easy to do the sexy part of acquiring more and more and more people but keeping them around is the hardest part. If a million people come and nobody sticks around, what’s the point? Think retention and optimization at this point.
The other thing is that there’s no question the single most effective tool in marketing is relationships: who do you know? Who can you reach out to to share your message? If you don’t have any answer to those questions it doesn’t matter how many great apps or tools you have. And if you haven’t built a platform before launch, you’re screwed. So I want to recommend that people spend less time obsessing about technology and more time with people, building connections, friendships and reciprocal relationships. And guess what? You can’t build a relationship a week before launch – it doesn’t work like that.
And if you have to boil it down to one thing, I would use an analogy when I discuss marketing with my clients who are authors and want to release a successful book. Writing is marketing, I tell them. Too many books fail because they were written in a vacuum, without ever considering anything beyond the author’s immediate tastes and needs. You can’t write without ever thinking: How the hell are people going to hear about this and why would they care if they do? You thought about why you wanted to write it, but not why anyone else needed it. Without product market fit, a book will never succeed. Significant research has to go into the potential reader, their needs, your abilities, your message, your desires and how to connect all those things.
In other words, the best marketing decision you can make is to have a product or business that fulfills a real and compelling need for a real and defined group of people.
What does success in life mean to you? What motivates you to get shit done?
Success is freedom to live your life on your own terms. I think a lot of people chase money but they forget that money is really a means to an end. But if you can figure out your needs and earn accordingly, you have real freedom. There’s a line from John D. Rockefeller, “If a man believes himself rich and has everything he desires and feels that he needs, he really is rich, no matter if he is worth only $10.” But people find that their tastes are always expanding and so they have to “succeed” more and more and more just to stay in the same feeling of “wealth.”
I was talking to Casey Neistat a couple years ago about money. I had said something about a large fee from a prospective but boring client and he said, “Ryan, if that was what we wanted, we’d work at an ad agency.”
It was like: Oh yeah, there are a lot of ways to make money. But I chose my way (writing and other such projects) instead of their way for a reason, namely because I tried it already and hated it. I don’t want what those people have and I don’t want to live and act like they do. So why the hell am I using them as a metric for success?
This is a topic that I’ve also tackled in Ego is the Enemy: you need to know what race you are running and why. Otherwise you are going to be constantly feeling like you have to catch up to all these other people. And certain strategies are often mutually exclusive. One cannot be an opera singer and a teen pop idol at the same time. So if you are pursuing one but feeling shitty that you don’t have the rewards of another? That’s so unfair to yourself and to the people you are jealous of. Once you understand that, it’s very easy to opt out of stupid races and ignore ‘successful’ people.
Speaking of ‘Ego is the Enemy,’ how did you pick the theme and can you tell us a little about your writing process?
When I originally started thinking about the book in 2014 the angle that I was going to take then was humility, but what I found is that would make for a boring book. Which is not surprising, we tend to think humility is not very inspiring, we don’t think it is the trait of people who accomplish things. And what’s the opposite of humility that prevents success? After some thinking I realized that the book should be about ego. And by ego I mean it in the colloquial sense, just think of all the times you’ve referred to someone as having a big ego. I don’t mean it in the Freudian or any kind of academic or clinical way. And in the book I wanted to illustrate with historical examples how your ego can be the worst ingredient to add into any situation, whatever you are just starting out, being successful or experiencing failure and adversity.
But also that period in 2014 was pretty hectic – both me wrestling with my own ego as well as seeing mentors and people I’ve looked up who were behaving in dysfunctional ways which was really scary to see. I even ended up tattooing the title on my forearm to serve as a daily reminder.
In terms of the writing process, the writing itself was hard. But what’s harder is to actually spend time figuring out whether or not you should actually pursue such a project that will take so much of your time and energy. As you can tell, I didn’t write the book I originally set out to write – it went through iterations and many conversations with my editors and the publisher. The book proposal was actually rejected a few times and I pivoted from the idea that I ended up selling as well. The other thing in terms of writing, obviously the notecards themselves were helpful with the research being done prior to the writing.
And I think your readers will like this: I actually documented the behind the scenes of making of the book that will give you some more understanding and insight into the entire process.
Editor’s Note: Totally recommend looking through the image gallery of Ryan writing the book. It’s cool to see behind the scenes and one of the comments is money.
What are you working towards, life-wise?
When we moved into our first house with my wife she said to me, “You know, I’ve always wanted to live on a farm.” Two years – almost to the day – we bought a 16 acre farm and now we’re up to 40+ with more animals I can confidently account for (it’s somewhere around 20 but if you include the cattle that a neighbor runs on the land, closer to 50).
And this turned out to be one of the best decisions I have ever made. I also never could have imagined I would have a mini-donkey that would get attacked by a mountain lion but that’s the kind of stuff I now deal with. And this is in the personal plan and it’s fulfilling. I don’t feel I need to “top that” in any way.
As for writing – I think there are some authors who are trying to sell a certain number of copies or write books to get speaking gigs. I so genuinely love writing that my goal is to try to do it for as long as I live. What’s so great about this job is that it’s something you can do literally up until the day that you die. So when I try to make career choices or evaluate decisions related to my writing, one of the things I ask myself is: Will this help me last until I am 80? I am not looking to now ‘pivot’ and become a startup founder or I’m not trying to get distracted with courses or other things. It can be hard when people are asking ‘what’s next?’ But you have to know what’s important to you and what your strengths are.
The same goes for my company Brass Check. We call it a “creative advisory” and we’ve worked with some amazing writers like Neil Strauss, Tim Ferriss, Tony Robbins as well as some cool companies like Casey Neistat’s Beme, Vinyl Me, Please, Google, Complex, Taser and stuff like that. I’m not necessarily trying to build something that scales or gets acquired. I want to make something that I enjoy doing, that pays me well for my time and produces work that I am proud of.
We’re big fans of yours over here at The Hustle. You down to do some collaborations in the future? I want it on record so we can hold you to it.
Of course. Just depends on the project and the price!
Ryan Holiday is the bestselling author of Ego Is The Enemy and three other books. His monthly reading recommendations which go out to 50,000+ subscribers are found here.
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