Ryan is a business and media strategist who has advised authors, artists, and companies. Among other accomplishments, he was a key part of American Apparel’s meteoric rise in sales.
Ryan made the tough choice to drop out of college at nineteen to apprentice under Robert Greene, author of The 48 Laws of Power. Afterward, he went on to advise a multitude of clients including bestselling authors and multiplatinum musicians. Ryan has worked for American Apparel as the director of marketing. At that firm, his campaigns were so effective they have been used as case studies by Twitter, YouTube, and Google, and have been written about in AdAge, the New York Times, and Fast Company. His first book, Trust Me I’m Lying, was a debut bestseller.
Turn up the volume and listen in, because you won’t want to miss this engaging conversation with an expert who combines amazing street savvy with deep philosophical thinking!
Welcome to the Brainfluence Podcast with Roger Dooley, author, speaker and educator on neuromarketing and the psychology of persuasion. Every week, we talk with thought leaders that will help you improve your influence with factual evidence and concrete research. Introducing your host, Roger Dooley.
Roger Dooley: Welcome to the Brainfluence Podcast. I’m Roger Dooley. My guest this week is among other things a media strategist and an author. He dropped out of college at 19 to apprentice under Robert Greene, author of The 48 Laws of Power. He served as director of marketing at American Apparel for many years where his campaigns generated controversy and media coverage.
His first book which the Financial Times called both astonishing and disturbing, was the bestseller Trust Me, I’m Lying. He’s also the author of Growth Hacker Marketing and The Obstacle is the Way. His newest book is Ego is the Enemy. Welcome to the show, Ryan Holiday—and fellow Austinite, I might add.
Ryan Holiday: Yeah, thanks for having me. It’s funny we’re talking remotely and we live in the same city. We’re probably like five minutes from each other.
Roger Dooley: Yeah, no doubt. Sometimes Skype gives you better—I think the technology is a little bit easier than in-person recording. I’ve done a few in person, they’ve turned out okay.
Ryan Holiday: That’s true, plus traffic in Austin is so bad these days.
Roger Dooley: Yeah, you’re right. Well, someday they’ll fix that, I’m sure. Once we have self-driving cars that will all be solved.
Ryan Holiday: Sure.
Roger Dooley: Ryan, let’s start, you’ve written this book according to your introduction so that readers will think less of themselves by the end. Is that really a good way to sell books?
Ryan Holiday: It’s probably not a great opening line. I mean, it’s not the opening line but it’s deliberate, right? I think the vast majority of business books tell people what they want to hear. So I think that has created a bit of a bubble in which everyone is encouraged to be this sort of hard-charging CEO or the whatever image they have of what an artist is like. You know, to live the life of a TEDx speaker.
I think we’ve created, in the way we might have an economic bubble, we have sort of a self-esteem bubble that tells everyone that they’re as great as they want to believe that they are. So one of the premises of the book is that that attitude is actually very much the antithesis of what is required to do really good, creative work.
I quote Marina Abramović, she’s saying, “Once you believe in your own greatness, that’s the death of your creativity.” I’ve certainly found that to be true in my own life. So I wanted to write a book, I’m not trying to tear anyone down or make them feel bad about themselves, but I’m trying to make them think less of themselves. Not think that they are lesser but to think less about themselves and more about other people and more about the work that they’re trying to do rather than their own ego.
Roger Dooley: It seems like in our culture it gets started at a pretty early age where kids are always told how great they are, they shouldn’t be criticized, everybody gets a trophy, and all that. It does carryover into adult life and business as well.
Ryan Holiday: Yeah, I would say social media is probably the most egregious example of all this. It’s like the illusion that you can present on LinkedIn or the snapshot of your life that you can create on Instagram really has no need to be connected to reality. From a marketing perspective I suppose this is a fine. The problem is we’re not that great at making a distinction between marketing and reality, even in our own lives. In fact, our brains are alarmingly easy to fool.
There’s studies that show that if you bite on a pencil which forces you to make a smile, you feel happier. So if you’re presenting or posing this image to the rest of the world, what is the likelihood that you’re going to be able to continue to make that distinction in your own private life? Like, “Hey, I really haven’t done all these things. Hey, really, it’s not going as great as I’m making it seem.” So there’s that line about how the face can form to fit the mask. It’s sort of that, and that can be very dangerous.
Roger Dooley: Then you’ve got the feedback loop too of all the likes and so on, so you’re getting this affirmation for these images that you’re posting whether they’re real or not, which may make them seem even more real. Do you think that this is sort of the start of a backlash against the idea that a leader has to be visionary, persuasive, powerful, and basically ignore naysayers to charge forward?
I just had a conversation a few weeks ago with Al Pittampalli, he wrote the book Persuadable. The theme is certainly different than your book, Ryan. But what he attempted to do was show that the best leaders are in fact great listeners and can change their mind.
His great example was the admiral who was in charge of the Osama bin Laden raid and various other daring ventures who was not the General Patton kind of guy but in fact took a lot of advice from other people and planned meticulously. Then the operations actually went off very well. The point that Al tries to make is that good leaders are very persuadable.
Ryan Holiday: Yeah, I think that’s right. I won’t pretend to know that this book is going to kick off some backlash. But I do think that that’s correct in the sense that, I mean, I even talk about this in the book. The two greatest generals of World War II were Dwight D. Eisenhower, who as many said had no personality and was more of an organizer than a leader. And George Marshall, who was even more of an organizer than sort of a battlefront leader.
But of course, we love Patton because Patton was bold, inspiring figure who gave fiery speeches. He was certainly good at what he did, we should just remember that he functioned best as one of the tools in the tool chest of these greater, bigger picture thinking leaders. So I think that’s a huge part of it.
I think we have this idea of we like the lifestyle of these larger-than-life figures but that’s probably because we don’t personally have to live it. It’s just very entertaining for us. If you had to ask yourself, who do you want to be? Do you want to be Dwight D. Eisenhower or do you want to be George Patton? Well, you know, Patton died pretty tragically and at a somewhat unflattering end of his career. He’d gotten himself in some trouble. And Dwight D. Eisenhower sort of plugged along and history has been increasingly kind to him.
I think Obama is another great example, not to get too political. The main criticism of Obama is not all the things that he’s accomplished or the incremental gains he’s made as a politician. It tends to be that he’s not making big enough promises or that he’s not throwing his weight around in the international scene enough.
So I think we’re getting to a place where the problems that we face as a society, that we face as people, they don’t need this inspiring leader, they need an immensely practical, pragmatic, incremental sort of tactician. One of the people I profile in the book is Angela Merkel. She has this great line, she was like, “Look, you can’t solve tasks with charisma.”
Certainly charisma is great from a marketing standpoint but when it comes time to the operations—ego might help you get up there and make a two-hour extemporaneous speech that gets a standing ovation. But that’s not what you need behind closed doors, working like hell on a difficult problem.
Roger Dooley: Yeah, you know Ryan, I think that Steve Jobs kind of did the world of leadership a disservice because he was obviously extremely successful, built the world’s most valuable brand, the world’s most valuable company. He did it with a personality that seemed to be sort of the opposite of what you’re talking about.
You do point out in the book that he changed his style somewhat when he returned to Apple, so he wasn’t quite as rejecting of other people’s ideas and thoughts. But still, the perception is that it’s all Steve Jobs. That he has this vision and didn’t want market research, didn’t want to hear from other people. That “do what I’m telling you to do and it’s going to be great.” In his case, it was great most of the time. But that’s not a strategy that works for most of us.
Ryan Holiday: No, certainly not. It’s easy to see the clear lesson of, hey, Steve Jobs as a visionary genius transformed this company and made billions of dollars. But I think when you start to sift through it, it becomes more complicated. First, he had to be fired from his own company. Like if you and I were John Sculley, we would have fired Steve Jobs because you can’t have someone like that walking around the office screaming at people, crying, unaccountable to budgets or reason. You can’t have that. You had to fire him.
So in many ways, you could argue that the Steve Jobs story could have ended right there. What’s so dangerous about Steve Jobs’ approach is that it works but when it doesn’t work, it really doesn’t work. What if Apple’s board had not approved the acquisition of NeXT Computers? We might not be living in an Apple world right now because if they’d been so scarred by that first experience, they might not have been willing to take that risk again. So he really made a huge gamble there. He just happened to work out for them.
I think the other thing you could look at is, I’m a big fan of Apple. I’m pretty bullish on the company but you could argue that Steve Jobs was such a force of personality that he put the company in a position where it was really hard for them to succeed without him, which is pretty common with big, outsized CEOs. It’s hard for them to put a succession plan in place because they cannot conceive of a world where anyone could do what they do.
I think Tim Cook is exactly the kind of executive that Apple needs and he’s done a great job running the company but was he set up to succeed? Probably not as well as he could be. I do think it’s interesting now, he in turn has made the company billions of dollars and all people want is another Steve Jobs to come in there and act like a madman. We forget that, yes, sometimes it works. But more often than not, it’s responsible for catastrophic failure rather than stratospheric success.
Roger Dooley: Right. Well I’ve certainly met any number of executives who manage as if they are Steve Jobs and have his level of insights but sadly, they don’t. They won’t be particularly successful.
Ryan Holiday: Yeah, I was on Twitter this morning and Chad Ochocinco, who’s obviously a bit of a crazy football player, he’s retired now. He was talking on Twitter about how he ate McDonalds throughout his entire career and how obviously it can’t be that bad for you or he wouldn’t have been as successful as he was.
It’s like, that might make sense in your crazy mind. But obviously, you’re just a bit of a genetic freak. Or it was the product of all the other things that you were doing that compensated for your horrible nutrition. The vast majority of people should not emulate your terrible diet.
But that’s sort of what we do with these egotistical personalities. We go, “Oh, it worked for them, it should work for me.” We forget that lots of other CEOs suffer from depression or alcoholism or many rock stars commit suicide. Just because they accomplished something that you want to accomplish does not mean these negative traits were in any way the cause of that momentous achievement. In fact, it was probably that they had to work extra hard to get over that.
Roger Dooley: Yeah. Ryan, somebody else that you talk about that probably our listeners have not heard of is John Boyd, who was a not particularly famous but extremely influential combat pilot who more or less stuck to his knitting if you will, practiced his art and craft of air combat, became an amazing pilot. Became a trainer. Then ultimately, I guess an influencer, designer, and strategist, all because he simply did not try and pursue rank or glory or acceptance. He just did his thing and ended up doing it extremely well. So ultimately, he was able to exert a lot of influence.
One thing though that I got from looking, in his training session for new recruits or new junior officers, he would say that they have two paths to follow. One that led to promotions and good assignments, involved compromises. The other that led to real accomplishments but perhaps a lack of acceptance by superior officers. I’m wondering, is that a real choice?
Like he happened to be really successful ultimately because he was so darn good at what he did. It seems like in most cases, in most real world situations, in order to accomplish what you want to accomplish, you have to live a little bit in both worlds, don’t you? Or is that not true?
Ryan Holiday: No, I would certainly agree with that. A couple things there. One, I think John Boyd is this fascinating figure. Robert Coram has a biography, it’s called Boyd: The Fighter Pilot Who Changed the Art of War. It’s one of my favorite biographies ever written. I guarantee you people will love the book.
John Boyd had this thing, he called it his “to be or to do” speech. That’s what he would give these young, up-and-coming officers. I think a certain part of it—it’s limited in its context to what it must be like to be in the armed forces. Where it’s a very rigid hierarchy, sort of a set criteria for advancement. You’re very dependent on other people’s reviews of you to advance.
Which there’s some analogies. I like to take that speech and apply it to say you’re about to graduate from college. To be or to do. Are you going to get a job on Wall Street or are you going to pursue something that you think can truly make a difference that will truly exercise your capabilities and potentials as a human being? I think about it in that context.
I also try to apply it in my own life. I think this will answer your question a little bit. It’s like when you write a book, I think we both know that there are certain things you can say that can pander—you could write a book, there’s sort of a playbook for what a short-term bestselling book is going to look like. It’s the guru on the cover telling people what they want to hear about this technology and about how everything is rosy and awesome. But is that going to last over time?
I try to think in my own life, okay, I want to make something. Clearly I want to reach people because what’s the point of writing a book if it sells one copy? I’m not going to deliberately make an ugly cover. I’m not going to be like the indie band that doesn’t want to be famous. But, I’m going to try to think long term and I’m going to try to think about having impact over say monetary rewards, up to a certain point.
I think John Boyd is someone who realized, like hey, as a strategist and as a groomer of the next generation of thinkers, I can ultimately have much more impact than I could if I became one of those politician generals. That’s the distinction that he’s making. I think we all have that analogous situation in our own lives.
Are you going to be one of the people who is really moving the needle in your space and making a real difference? Or are you going to be the person that sort of goes with whatever is popular right now and sort of surfs from wave to wave. It might be the most well known in the space but it ultimately has very little real impact or influence.
Roger Dooley: Another balloon you try and pop, Ryan, is passion. We’re all told to be passionate about what we do. Follow our passion. That unless we’re passionate we can’t be successful. You sort of take the opposite viewpoint on that, don’t you?
Ryan Holiday: Yeah, I know it’s a bit of a sacred cow. I mean, obviously I’m passionate about what I do. I’m not saying that you should find some crappy job you don’t like. What I’m saying is that the ancients had a much different attitude to that word than we do know. You look at the Stoics, they see the passions as being these sort of dangerous currents that run through the body that lead us astray. Today we think passion is this like raw bit of authenticity that must be cultivated.
I tend to make the distinction between purpose and passion. Would you rather have—if you’re hiring a young person to work for you—would you rather them be very purposeful or be very passionate? I see purposeful as someone who knows what they’re trying to accomplish. They have a bigger goal that they’ve attached themselves to. They’re working hard. They’re dedicated. They’re willing to endure things for the sake of this purpose, so on and so forth.
Then I see passion as this kind of person who kind of likes what they’re doing but really they’re just throwing a lot of energy at it. They’re all over the place. They’re hard to contain. They’ve replaced energy with intelligence in some ways. So I see passion as being this difficult-to-control force whereas purpose, that control and that direction, has been done for you.
I think, look, if you don’t care about what you’re doing, if it doesn’t get you excited, that’s a bad sign. But if the main ingredient that you are bringing to a project is your energy, that can in many cases be a negative asset because if not directed properly it’s just going to sort of explode all over the place.
Roger Dooley: Yeah, what I get out of that part of the book I think, Ryan, was that passion is so much about emotion that sometimes rational thought gets suppressed. Some of the examples that you give, like the folks who were—Dick Cheney and all in the lead up to Iraq and I’m sure you could probably take the much earlier Bay of Pigs team of decision makers.
What it leads to is confirmation bias where you’re so wrapped up in the emotion that you reject information that doesn’t agree with your preconceived notions. Then of course you look for supportive information. I think we’re all subject to confirmation bias but when we’re passionate about something, it can get even more intense and obviously if you’re making high-level decisions, that can be a flaw.
Ryan Holiday: Yeah, absolutely. Even when I was writing this book, originally I sat down and I wanted to write a book about humility. That’s the original sort of what the proposal was about. But what I realized when I was doing the research and sort of kicking my notes and my outline around, that was really hard to do. I realized that ego was a better lens to attack the same problem.
I’m sure you’ve talked with writers before, it’s like, “I’m writing this book and I sit down and I write 5,000 words every morning and I’m going to be done in six weeks and then I’m good to go.” That sort of deliberative process is lost. So they throw all this energy and so much of that energy is wasted.
So one of the things John Boyd would talk about, most of his greatest discoveries were preceded by what he would call a “draw down” period. He’d have this idea, he’d be really excited about it. He’d have researched some of it and then he’d sort of put it aside and sit on it for a little bit and just kind of meditate on the idea.
Has anyone thought of this before? What are some potential problems with this idea? If I proceed on this, what is it going to look like? Taking that beat to consider things. To me, that’s the difference between purpose and passion. Passion just, you know, it’s zero to one hundred. It doesn’t stop to think. It’s shoot first, ask questions later, which can work except for when it doesn’t work, it really doesn’t work.
One of the hardest things to do as a writer for instance is to toss out things that you sweated over making. So if you’re not thinking before you’re writing, you’re putting yourself in a position where you’ve really got to do that.
Roger Dooley: Yeah. One guy that keeps cropping up in the book is Bill Belichick, coach of the football Patriots. According to Wikipedia, by the way, the Patriots read your Obstacle book during their last Super Bowl victory which created a great mental image there of these sweaty guys in pads reading your book.
Be that as it may, I read Halberstam’s biography of Belichick as well. A great book. He’s such a gifted biographer and author. But you know, at the end of it I was a little bit disappointed. I expected to find that there was another side or perhaps several sides to Belichick besides football and film. After reading the book, I came away feeling, well, there’s really not much else there. This guy is all about football and film. That’s what he does.
At the same time he, to some degree, suppresses his ego. He’s not out there. He’s not out in the press the way so many coaches are and so on. He doesn’t look for personal attention. To what extent does he exemplify the sort of leader that you would want to see in your book?
Ryan Holiday: It is interesting. I think when you read about like Nick Saban who is one of Belichick’s protégés, he’s like the same way. He’s now sort of built up from scratch three different football power houses. Even just a couple years ago he was considering leaving to do it again.
He has this inability to be satisfied with the immensity of his accomplishments. Which I think has obviously driven him to be incredibly accomplished but it’s probably not a recipe for individual personal happiness. I think that’s certainly something to be concerned with personally and I took that from the Halberstam book as well. I don’t know Bill, but that single-minded focus makes you very good at what you do but also makes you very vulnerable, especially when that thing is not going well.
One of the chapters I have in the book, the Patriots are famous for having drafted Tom Brady. Most people, since he’s probably the greatest quarterback—he’s certainly the greatest quarterback playing today—maybe the greatest quarterback of all time.
Roger Dooley: I’m a Colts fan, so we can have that discussion later.
Ryan Holiday: Yeah, I mean, they’re couldn’t have been a better way for Manning to go out. But I think sort of year in, year out, Tom Brady is one of the greatest quarterbacks to ever play the game.
Roger Dooley: Sure.
Ryan Holiday: So people forget because they just see that, they don’t understand that he was drafted as like a sixth-round pick and he was like 200th in the draft. It was not great. So you’d think in that way he’s probably the greatest draft pick of all time. For him to be drafted where he was drafted and then to accomplish what he’s accomplished, that would be like picking up Google stock for like one penny on IPO day. Just a tremendous bet.
They talk about this in the Halberstam book. When you look at the Patriot’s response to that drafting, they don’t pat themselves on the back on it. In fact, they consider it to be a failure because their intelligence was wrong. They thought they were picking him at about where he was valued. Then their error was only made clear to them when Drew Bledsoe got hurt and Tom Brady replaced him. So it was really random luck for all…
Roger Dooley: So Brady made them all look like geniuses.
Ryan Holiday: Yeah. For all of Belichick’s genius, which he clearly has as both a picker of players and as a coach and as a strategist, it might not exist were it not for this random, fortuitous break. The Patriots are aware of that and they’ve put that into their self-image. One of the most dangerous things that can happen when you’re successful is that you take credit for everything that happens and you gloss over all the lucky accidents.
I’ll give you an example of my personal life. The Obstacle is the Way is my most successful book. It’s outsold my books by three or four times. I could sit here and be like, “Oh, I made this amazing book. It sold so well.” But I could conveniently ignore the fact that a random computer glitch on Amazon, like an uncaring algorithm discounted the book for like seven months.
We don’t really know why this happened. We just know that I was the beneficiary of a suppressed e-book price that drove an immense amount of discovery for the book that’s become sort of a self-fulfilling prophesy. Now that I’m doing my second book, I can’t sit here and go—or not my second book—now that I’m releasing the sequel to that, it would be real dangerous for me to walk around with the assumption that my book is going to sell out of the gate like that again. That people are just going to pick it up.
I’ve got to remember, hey, I got a lucky break. If I want to repeat that success, then I have to be even better the second time. I have to make up for the lack of that break. So that’s the problem with ego. Ego loves taking credit for things that it had nothing to do with.
I think the Patriots have gotten pretty good at sort of putting everything on the system and everything on the analysis and not letting—look you can’t build one of the most successful franchises in history year in and year old if you’re convinced that it’s yours by right and it’s going to proceed forever.
In fact, in football, as you know, once you win the league, that’s what impacts your salary cap. That’s what impacts your draft status. That’s what impacts your schedule the following year. So in a weird way, football is this perverse form of socialism that makes it harder to do well year in and year out.
Roger Dooley: Right. It’s really geared toward parity and of course, your Super Bowl winning players are now in high demand as well from other teams.
Ryan Holiday: Totally.
Roger Dooley: Yeah, what they’ve done over the years has really been pretty amazing. Your last two books have been more philosophy, self-help to a degree, sort of applied philosophy I guess. Do you have another marketing book coming ever or are you going to stick in this newer genre?
Ryan Holiday: I call it practical philosophy which I think is a bit ironic because philosophy has always tended to be practical, it’s just only in recent times it sort of stopped being that. I started with a marketing book. My second book was a marketing book. Although I’ve been writing about this stuff before I got into marketing so I sort of get it from both sides. People are like, “When are you going to write another marketing book?” But when I was writing marketing books, people were like, “When are you going to write these other books?”
Roger Dooley: You just have to do both, Ryan.
Ryan Holiday: Yeah, I have a marketing book coming in 2017. I want to focus on classic products. I’m really interested in, again, like with something like the Patriots, what’s the business equivalent of the Patriots when you find out? It’s like, “Oh, this company has been in business for 400 years.” Or, “This diner has been open in the same spot and they’ve never closed since 1918.” I’m really interested in the marketing and the business approach that it takes to create something that really lasts.
Roger Dooley: That sounds like a fascinating book. We’ll have to be watching for that one. Let me remind our listeners that we are speaking with Ryan Holiday, author of Growth Hacker Marketing, The Obstacle is the Way, and his new book, Ego is the Enemy. Ryan, how can our listeners find you and your content online?
Ryan Holiday: I’m @RyanHoliday on Twitter and my website is ryanholiday.net. You can check me out at either of those places.
Roger Dooley: Great. We will link to those places as well as all of Ryan’s books and the other resources we talked about in our conversation on the show notes page at rogerdooley.com/podcast. We’ll have a text version of our conversation there too. Ryan, thanks for being on the show.
Ryan Holiday: Thank you so much for having me.
Thank you for joining me for this episode of the Brainfluence Podcast. To continue the discussion and to find your own path to brainy success, please visit us at RogerDooley.com.