Habits, Obstacles and Media Manipulation - Ryan Holiday Interview

Hello and welcome to near and Far. Today I have a very special guest with me, Ryan Holiday, who is an author of three books. But let me tell you a little bit about Ryan before I tell you more about his books. Ryan dropped out of College at age 19 and yet has had an unbelievable career. He's worked with best selling authors such as Robert Greene. He was the director of marketing and American Apparel in his early 20s. And then as I mentioned, he published three books and all this by the age of 26. He's also a controversial character who's worked with some figures such as Tucker Max. He's been accused by some, including himself, as being a media manipulator. And his latest book is called the Obstacle is the Way. And he's also written a book called Growth Hacker, a primer on the future of pr, marketing and advertising. And my personal favorite, he wrote the book, trust me, I'm Confessions of a Media Manipulator. Thanks for joining us today, Ryan. It's a pleasure to have, have you.

Yeah, thanks. That was very kind.

So Ryan, you've accomplished a hell of a lot. Let's start with that. Three books by the age of 26, many of them bestsellers. Tell us more about your daily routine, your daily habits, what's your day to day life look like? How do you do so much?

Yeah, so I don't know how you feel about writing, but I find that writing is sort of a full time occupation. Like it's best when complementing other things. So I tend to write in the morning. I get up early, like 7 or 8. I usually work out and then I write in the morning for an hour or two. I have research assistants that I work with, but I'm doing the bulk of the writing there in the morning. And then I write sort of until I hit the point of diminishing returns. And then I start my client work. That's when I answer emails, that's when I do calls. Like this morning I wrote an article, I ran, I got that part of my life done and then I sort of start and work on a normal person's schedule.

Yeah. And do you consciously think about habits and optimizing for your day to day habits?

Yeah, totally. Like, I mean, I think you have to. To me it's about finding a system that works for you, that takes, that makes it harder to what Steven Pressfield calls the resistance. What makes, what makes it harder for the resistance to sort of take hold. If you don't have a schedule, then you can turn on tv, you can get Distracted by things. Small projects can be ballooned out to take longer. You can avoid doing, like sitting down. And writing, while not difficult, is uncomfortable and can be unpleasant, especially when it's not going well. And so in my eyes, you want to keep it in a brief sort of flurry of constructive time, and then you move on and you go to something else. And that's come out of me trying different ways and those ways not producing the same results, and then settling on this system and more or less sticking to it.

Now, your book, the Obstacle is the Way, talks about how you use this philosophy of stoicism to get through these difficult obstacles in our life. How do you apply? Well, first of all, tell us about what stoicism is about. The premise of the book.

Yeah. So Stoicism is a Greek and Roman philosophy. It's many thousands of years old, and we could get into the sort of complicated sort of tenets of the philosophy. I define it very simply. I say the Stoics assert that we don't control the world around us. We control how we respond to that world. And so the book is about how to respond, how to respond well, how to respond efficiently, how to respond what the Stoics would call virtuously. So when I'm thinking about my routine, I'm not trying to. I know that there's going to be distractions. I know that it's not going to go well sometimes. I know that I'm going to have a million other sort of tempting influences or things to work on. And you try to create something that's robust, that can resist that. But also, you're not spending all your time fighting it. So when I think about stoicism, I. The formula of the book is, okay, I'm working on something, and it went terribly wrong. I can be upset about that, which accomplishes nothing, or I can say, this is an opportunity to do X, and then filling in that blank.

Right. And you give a lot of examples, historical examples of how people have done exactly that. What are some of your favorites from the book?

Yeah. So personally, I find that telling stories from history is easier because they're harder to argue against. You know, we all know that. I think we all know that these things are true, that you can decide to look at something as an opportunity or as an obstacle. But if I was to tell you about the time that, you know, my computer crashed and I lost something I was working on and I got over it, you wouldn't be like, oh, wow, that's very inspiring. Like, how did you. How did you overcome this adversity? But when you can hear about, you know, I talk a lot about Ulysses S. Grant, who I think is an underrated, often ignored historical figure. I think his siege of Vicksburg was a textbook example of the powers of persistence and ingenuity. I talk about Thomas Edison a lot. I tell this great story about his factory burning down and him sort of seeing this as a chance to start over. This was like, oh, we just got rid of some old things. He tells his son at the scene, he says, go get your mother and all her friends. They'll never see a fire like this again. You know, I talk about Amelia Earhart. I talk about Samuel Zemuri, who was the founder of United Fruit. It's all sorts of historical figures from basically every historical era you could think of who are all dealing with what entrepreneurs and creative types and even executives deal with, which is a world that doesn't seem to go your way as often as you would like. And you have a choice there. Does that piss you off or do you make it work?

Right. And so how do you apply this philosophy to your own life day to day?

Well, I guess it would depend. As a writer, it's obviously more of an insular process and sort of telling yourself, hey, this thing that happened, it's very upsetting and I'm mad about it. And I can get upset and I complain, or it can be material for something that I'm working on. I can use this example. I learned a painful lesson. Well, does that make for a good article? And then in my business life, you know, working with clients and companies, stuff goes wrong all the time. I tend to work for some relatively controversial or difficult clients. And so stoicism is a way to say it doesn't matter how these people are behaving. It doesn't matter how they are acting. What matters is how you handle yourself in those situations. It matters. Can, regardless of what goes down, can you just move the ball forward a little bit and can you be happy with that? So stoicism, to me, I think some people think stoicism is depressing or fatalistic. But to me, stoicism is a recipe for ingenuity and a unique kind of sort of pragmatic optimism.

Right. And how do you keep that top of mind? I mean, when you're in the throes of a difficult situation, how do you remember to look at things one way versus the other?

Yeah, I mean, what's interesting about stoicism, compared to essentially all other philosophy, except maybe Eastern philosophy, is that it's really just a series of very simple sort of aphoristic observations about the world. And these are observations that have been refined and reduced to their total essence over thousands of years, sort of filtered through successful, important people. So you know, you have Marcus Aurelius, the most powerful man in the world, writing to himself one day, like, choose not to be harmed, choose not to. Choose not to feel harmed, and you won't be harmed. And so it's like, oh, the next time someone pisses you off, they cut you off in traffic, someone says something rude to you, this thing sort of filters through your mind. So stoicism is sort of three things I would say. It's reading, it's writing. A lot of stoicism is sort of journalism, journalism journaling at the end or the beginning of the day. And then it's just applying these things in your life and you build them up like habits, just like you do with anything else.

Right. So that first component of reading, I have to say that part of, I'm guessing what makes you such an intelligent writer is that you read a tremendous amount. I mean, you read more than anybody I know. In fact, you have a great email newsletter about all the books you've written and what you think of them. And so I wanted to kind of share with the audience how you read so much. Kind of. What's your daily practice of getting through so much information? Sure.

But look, I would say that generally successful people tend to read a lot. I read a lot a lot because I love it. But like, I would imagine most of the people that you talk to or the successful entrepreneurs that you work with, they read more than the average person, right?

Well, some of them, yes. And it also depends what they read, Right. A lot of people consume kind of snack. Snack portions of blog posts and they find it difficult to read long books. But you're constantly profiling and reviewing 700 page works.

Well, look, I see writing as part of my job. Right. I see one because it quite literally is. But more, no one else is going to magically hand me this knowledge, but it's available to me and I'm going to try to incorporate it into what I do. And so some of the best investments that I've ever made in my life have come in at $15 increments at Barnes and Noble or Amazon. And so I make reading a priority. I don't speed read. I don't have any secret method for reading books. I make a lot of time for it because it's part of my job and then after I read, I don't just let that knowledge sit in a book. I try to apply it or organize it in some way. So I use, I've written about, I call it the note card system, but I mark a book as I'm reading it and then I use 4x6 note cards. And then I transfer what I've marked down to these note cards, which I then organized by theme in a box in my house.

But there's one trick that you didn't mention, which is that you've written about how you're a binge reading addict.

True. Yeah. So like I didn't read yesterday and I don't think I read the day before that, but I think I read like two books over the weekend. Right. So I tend to read in spurts, usually around topics that I'm just utterly fascinated in. So I think that sort of batching makes you much more efficient than reading like 100 pages a day of stuff you're not that interested in. So I tend to swarm around certain topics I absorb a lot and then I go from there. Like for instance, I don't read a ton of marketing books now because I have a decent base of knowledge. There's. But when I was 20 years old, I read literally everything that I could get my hands on.

Right.

You sort of move from topic to topic and that way you sort of get in a shorthand and you know that you're not learning this stuff from scratch each time.

Right, Right. And clearly that kind of focus on one topic gives you this energy to keep going, to focus on learning more. Do you find distraction a problem? A lot of people I speak with think that our technologies are making it more difficult to focus on these long form type tasks.

Sure. So I read physical books almost exclusively, which is funny because Growth Hacker came out as an ebook first. Like if, if I hadn't written it, I probably wouldn't have read it. So I only read physical books and so I can take notes in them. And then when I read on my. I, I don't really read any articles on my computer. I use Insta paper. And then it. I'm removing the ability to be as distracted by the content.

Love it.

And I think that's really important.

Right, Right. So let's talk a bit more about some of your other books about Growth Hacker marketing. It came out first as an ebook and I'd love to kind of get a quick overview in the time we have left about what you learned from that book, from writing that book, and what you Think kind of the most powerful lessons and takeaways could be for folks.

Yeah, I mean, it's interesting. Both you and I, we have the same publisher, which is Portfolio Penguin, and both like, I've done the traditional way of publishing with them. Like I wrote a proposal, they bought it, I published the book, blah, blah, blah. But both you and I have published books with them that are totally outside the norm of how traditional publishing works. Like you self published book and it was successful, it was validated by the market. And then you partnered with the publisher to ideally take it to another level and a bigger audience. And with growth Hackers, it was even more unusual. I wrote an article for Fast Company about growth hacking, which is something I'd read about. I'd read Andrew Chen's first essay about it and I thought was really interesting. And I said, oh, I'm going to write about this. I'm going to take what I've learned and try to add something to it. And so I got an email from Nikki, who's my editor at Portfolio. She said, I liked your article. Clearly it did really well. What would you think about turning it into an E special, which I'd never heard of. And we ended up, we published a 10,000 word ebook. My main negotiation with them was like, I don't really care what I get paid, but I want this to be cheap. I want people to be able to take a chance on it because I'd like to acquire new readers. So then when I come out with my Stoicism book, I will have a bigger platform for this book that I'm really excited about. And so I sort of see that growth hacker marketing, the first edition as being like an mvp. It was, it was the smallest version of a book that it could be because it validated by the market, it sold well and then we doubled the length, we added a bunch of stuff and updated what we could and it came out last Tuesday in paperback and now it's in bookstores and I think it's been translated in like seven languages now.

What was the biggest takeaways from writing that book? And kind of what's the biggest lesson you'd like to people to know from the book?

So in terms of the actual content of the book, for me it was, there's the line, I forget who I quoted from it. He says that growth hacking is a mindset, not a toolkit. People tend to think growth hacking is like it's doing this or it's doing that or it's the way that Airbnb or Dropbox did X. Really, it's about how they thought about the problem because it's all going to change depending on what you're doing and who you are in terms of actually publishing the book. The big lesson for me is I thought I was just publishing this essay that I hoped would do well, this short book that I hope would do okay, and it really resonated with an audience much better than I thought. And I think part of minimum viable product is having the humility to say, like, we don't really know what's going to do well and what's not going to do well. And we're doing these tests so we can be more objective about it and we should be open. And it's so much better to be. I would much rather have published something, taken less money up front for it, and then be blown away at how it was received than to take a lot of money for something, be certain it was going to be successful, and then be massively disappointed.

Absolutely. Yeah. But on the topic of growth hacking itself, I mean, that term has kind of gotten some flack over the past few months, particularly just the other day from Paul Graham, who said that if you hear anybody saying the word growth hacking, you can basically substitute that for bullshit. What do you think? How do you react?

Well, look, the alternative is talking about marketing the way people have always talked about marketing, which is its own form of bullshit, right? Which is like, oh, we've got to do this. It's got great brand value, we're capturing mindshare, all these things that agencies use to charge massive recurring fees that are impossible to evaluate their effectiveness. So I see growth hacking as an important distinction in a marketer's job, which is to say your job is not to do marketing, it's to grow this company and to be involved in all the different processes that do that. And it's marketers and PR people taking a more active role in doing the things you talk about in Hook. Like, it's not just, hey, get us some press or publicity, but how can we build marketing into the product and make a product that for the most part markets itself or encourages people to market the product? And I think that's really important. Obviously, in Silicon Valley, trends come and go and everyone jumps on the bandwagon because they hear so and so is getting funding for this, or this is how somebody did X and. And there's a lot of that. And I get why people are suspicious, but I don't think you can throw the baby out with the bath monitor Right.

Which is interesting because before you wrote Growth Hacker Marketing, you wrote this book, Trust me, I'm Lying, which this is really from your experience in the PR world. It's a great read. It's a really enjoyable read. And it's kind of a how to guide a little bit. How Hooked is a how to guide that kind of shows both sides of the coin. Right. You kind of, you feel like you buy this book because you want to know how to do it, but you're also kind of seeing the underbelly of this industry and kind of the flaws in the system as well. So do you still think of yourself as a media manipulator?

I mean, I wrote that book because I wanted not to retire, but I wanted to expose something that I think people didn't fully understand. And part of getting them to listen to me was being very sort of amoral and agnostic about what I'm talking about. Like, I had to prove that I knew what I was talking about more than I had to prove that I had good intentions. So obviously that was, that was somewhat, you know, I'm still dealing with some fallout from that. But there's, there's worse things in the world for me. The book was trying to go public with something. I think I accomplished that on a day to day basis. Am I working with clients to do what I talk about in the book? Almost. Almost certainly not.

Did you come out the other end of that experience with more of an ethical guide around what you will and won't do?

Yeah. Also, it just, I think I came out of it thinking like, okay, I put all this stuff in a giant pile and lit it on fire. And now I never have to think or do about it again. And now most of the clients that I talk with are people who are like, thank you for articulating this, please help me fix what's been done to me. Or can you help rehabilitate us in some? Like, I mostly deal with sort of like, I think, trust me, I'm lying is about offense. And now I mostly consult or advise with people who are trying to play a little bit of defense.

Fantastic. Very cool. Well, one last question. I'm going to ask you a paraphrase of Peter Thiel's favorite question around what's one hidden truth about the world that people don't know?

Huh. So there's this great line from William Goldman, and I quote it in Growth Hacker, where he says, like, nobody knows anything, which is a truism he was saying about Hollywood, like, nobody knows what's going to be successful or not. I think another thing that the Internet has done is it's created these sort of figures that we think are very mythical and successful and brilliant because they built these rapidly growing companies or they've written really good essays or whatever they've done. And then you actually meet these people and you sort of figure out that they don't know that much more than the average person does, so they sort of fall. And I talk about this in Trust Me, I'm lying too. But this sort of claiming expertise is so easy and you can fall for that and it can cause a lot of problems. So a hidden truth is nobody really knows what the fuck they're talking about.

Amen to that. That's why I claim ignorance. Right. I think people think authors, you come out of some cave with all the answers, and that's just not the case. I've always found that I write because I'm looking for the answers. Right. I do research, I study because I'm curious and I want to know the answers.

Well, look, I think the best books are the author writing it for themselves.

Right? Right. Absolutely. Well, Ryan, thank you so much. It's been a pleasure to talk to you. Your latest book, the Obstacle is the Way. It's a fantastic book. I hope you'll get it. As well as some of Ryan's other work around growth, hacker marketing, and Trust Me, I'm lying. Ryan, thank you so much for being here today.

Awesome, man, thanks.