The Jay Kim Show #12: Ryan Holiday (Transcript)
Today’s guest is Ryan Holiday. Ryan is an author and media strategist and the former director of marketing for American Apparel. He’s written five books now and has advised many prominent best-selling authors, including Tucker Max, Neil Strauss, and Tony Robbins.
Ryan’s story is particularly interesting because he dropped out of college at the age of 19 to apprentice under a famous author, Robert Greene. We talk about specifically how his family reacted when they heard the news that he was dropping out of college and how he dealt with this and overcame the challenges of not having a traditional college degree.
Ryan’s written three best-selling books on stoicism. His latest is called Ego Is The Enemy. I highly recommend you reading this book and learning more about stoicism. It’s practical philosophy that we can use in our everyday lives. I hope you enjoy this episode.
Jay: Ryan, thanks for coming on. I’m very excited to talk to you. Congratulations on your book launch.
Ryan: Thank you.
Jay: It’s amazing, the speed in which you pump these books out is amazing. Congratulations. I think you’re doing a great job.
Ryan: Thank you.
Jay: I’ve read all four of your books, and each one has some very unique messages. Really, I think your first one was very eye opening for me because I don’t know anything about the media industry. I think that was an eye opener. Your last two especially were more actionable type books which I loved.
Ryan: Thank you.
Jay: Let’s get right into it. I want to first talk about, I think it’s so unique that you dropped out of college and you’ve then just had such an incredible success. I think that, I’m Asian. I’m from the States but I’ve been in Hong Kong for probably 11 years now. The audience here is very, obviously very Asian. Doing something like that is unheard of in Asian culture. It’s not exactly encouraged either in Western culture. I just want to ask you about your experience doing that. What prompted you, pushed you or pulled you to do that and how did you so successfully parlay that into your career?
Ryan: It was a terrifying thing, to be perfectly honest with you. It’s not as discouraged in Western culture as maybe it is in other cultures. That doesn’t mean that it’s encouraged. There’s really no map that says, “Hey, this is what dropping out looks like.” Because most of the people that drop out, drop out because they’re not doing well in school. Then the other percentage of the population that drops out, when Mark Zuckerberg left [state 00:03:55], it’s a different thing. He’s got a multimillion dollar business that’s chugging along.
That’s not what it was for me. It was on a much smaller scale, maybe the way it looks like to a basketball player or something where you went to school to maybe go professional in this thing. I got an offer to do that. Instead of making a means of dollars, I was making $30,000. I had to really do the math and think, okay. The purpose of going to school is to secure some employment or advantage in this field that I’m pursuing. I’ve got that. I’m going to have to do it. It was terrifying and my parents were very upset. We didn’t talk for a long time. It challenges all the safety nets that we’ve built up as a middle-class society.
Jay: What was it, though? Was there an opportunity that you saw that pulled you to do this?
Ryan: I had an internship at a talent agency. I had help them work with some bands. They said, “Hey, now we’ve signed these bands. We can’t have you go back to school, basically. We need your help.” It was this digital transformation in the business and I knew what I was doing in that regard. Not in anything else in my life. They wanted me not to go back to school. I really wanted to do this thing they were asking me to do. I said, “Okay, let’s do it.” It was, again, scary. You got to realize just because it works out in retrospect does not man that there was that much indication that it would have worked out at the time.
Jay: Right, exactly. I think that the biggest, my parents would have been like, “Okay. We’re going to disown you now and don’t ever come back, because how are we ever going to be able to tell anyone what you’re doing?” I guess your parents were I guess kind of supportive and the fact that they actually let you pursue this. I’m assuming you didn’t have a huge blowout with them.
Ryan: No, no. We had a huge blowout.
Jay: Oh, okay.
Ryan: I reject the idea that one’s parents can let them do anything. At 18, you’re an adult. You can make your own decisions, and you had to be able to own the consequences. The consequences of my decision was that my parents were very upset. They tried to pull whatever strings they had with me, cutting various things off. They tried to use the most persuasive of all parental metrics, which is the withdrawal of affection or approval. It made a very difficult thing even harder. Over time, I think they begin to realize their mistake. I began to realize that I’m not sure I wouldn’t have done the same thing. The role of a parent ultimately is to keep you safe, not necessarily to make you … not encourage you to take risks that may or may not help you thrive as a person.
Jay: Right. Then you go into this whole question of education is changing as the way we know it now. Everything that you learn in school you can basically learn on your own or online. I think the way education will be taught in the future is also going to change. I don’t think it’s going to be …
Jay: Yeah. I think …
Ryan: It’s absurd to me that the obligation of the modern parent is to pick up the tab of $100,000 worth of education at the end, after your child has legally become an adult. That’s absurd to me and sad. I understand it because if you don’t do it, you’re disadvantaging them, but it’s completely unfair to everyone.
Jay: Right, right. Okay, so then the talent agency, how did you then network or meet or run into the next stage of your career? I don’t know if it was working with Robert or Tucker.
Ryan: It all happened at about the same time. I didn’t just leave to go to the agency. I had also met Robert Greene, and he was a research assistant. That was something that I thought was going to happen but I wasn’t totally sure yet so I took a flyer there and ended up coming together around the same time after I dropped out. I had these two jobs. I was cobbling together a decent living at that age. I was doing exactly what I wanted to do. I felt very lucky in that regard.
Then from Robert, Robert is on the Board of Directors for American Apparel. After some time passed working for him, he made a referral there, and this process happened again. That’s what I don’t think people realize is that they think getting a degree is what’s going to get them ahead. That might be true in certain fields that very, very much require those degrees. Knowing a person and doing good work for that person who has the ability to make calls or decisions is ultimately going to be far better than any piece of paper.
Jay: Yeah. If you can get there without having to have that degree or using the recruiting process through the school, then I think that that’s all that matters, really. For me, I went to, I went to UNC Chapel Hill. I went to work on Wall Street right afterwards. Just the fact that I was in the South and I didn’t go to an Ivy League school, it was a lot harder for me to network to get up to Wall Street. It was one of these things where, hey, if my diploma had said Harvard or Princeton, then it would be a lot easier to get a job like that. I don’t think that, I think if you can get there without it, then by all means, right? Yeah, I think it’s incredible what you did.
Also I think I want to ask you, because it takes also a certain level of maturity. I think at that age, for me, when I was 19, I was getting drunk every night. I didn’t even think about, oh, what do I want to do with my life? What I want to do 5, 10, 15 years down the line? I was just following what all of my peers were doing, having the time of my life. Was there a point?
Ryan: I think that’s one of the problems with this system is it infantilizes people who in a previous era would have been fighting wars or having kids or exploring into the frontier. It was great. I was 20 years old and all of a sudden I was responsible for myself. I made a lot of mistakes certainly, but I didn’t get to go drink and dick around because I just took an enormous, it’s like I burned the boats behind me. I couldn’t go back. I couldn’t blow it either.
Jay: Yeah, that makes sense. It’s also tricky because I’m a finance professional. I work in a hedge fund now. I also, I’m a fitness entrepreneur. I’ve written a book that’s being published now. I’m building a fitness product type stuff. I’ve always done entrepreneurial stuff in my past. I’ve also always had sort of a day job. There’s been, in-between careers I’ve had brakes but I’ve always had that day job to go back to. I think that there’s two camps. The one camp is really, really overplayed where they’re like, oh, you got to quit your day job and you got to chase your dreams, blah, blah, blah. For me that’s not very practical.
I think that a lot of kids, unless they know young people, unless they know exactly what they’re doing and maybe they’re financially secure, I don’t necessarily advocate them doing that. Because a lot of times what happens is you do that and then you realize you’re way in over your head and you don’t know what you’ve done and you’ve given up this great job that has given you the security that you don’t have to worry about paying your rent or keeping the lights on. Then all of a sudden you have this added pressure to get your startup, whatever you’re doing successful. This whole concept of chasing money versus the dream. For me it’s always been, okay, let me get too money first so I don’t have to worry about that.
Ryan: This is the first period in my life, about the last year and a half, that I haven’t had a day job as the director of marketing for American Apparel for a very long time, even when I wrote my first three books. I left in 2014. Now I have a consulting, I own my own company, but then I’m also a writer. It’s like in a weird way I have a similar set up. Then I have two sources of income. I’m not living or dying off either one.
Anyway, I did some investing and stuff as well, which wasn’t bad. The idea being I think that if you’re really good at what you do, you don’t need to quit your job to have things on the sides because it doesn’t require the full breadth of your capacity in the way that might for someone who’s not quite as good as that same occupation. For me, I’ve been able to have multiple irons in the fire. It’s been great because it creates some independence. It’s not like you’re a trust fund kid, but you get to think a little bit more long-term about stuff. You don’t just have to say, “Look, I need to take this gig or I can’t eat.”
Jay: Yeah. I think the other problem is, and I’m guilty of this as well, is people getting patient. You kind of, yeah, I just want to hit it big or I just need that lucky break. You don’t realize that, and Robert Greene talks about this in Mastery that the people that have achieved the pinnacles of success, they been working at it for years and years and years. It doesn’t happen overnight. It’s not just something like, oh, today I’m going to wake up and I’m going to hit it big because I’m going to be a master at this. It takes years and years.
Ryan: That’s what’s dangerous about that advice of following your passion. That’s like 1/10th of what you needed to succeed. It’s great to have passion I suppose, but if it’s not combined with some sense of purpose, if it’s not also combined skill, if it’s not also combined with a plan, it’s just desire.
Jay: Right. Yeah, that makes sense. Okay, I want to talk about your book for a bit, the latest one, Ego Is The Enemy. I thought it was awesome. I thought it really, I felt much more personal to me I guess. I don’t know if it’s because of the way you intro’d it. You opened the curtain and showed some vulnerability. I think that for me, and I think a lot of I think Asians are more conservative in general. My folks were very conservative Christian background type Asians. The whole concept of ego is definitely shunned upon. They were like, okay, don’t be proud, don’t have an ego, don’t showboat so to speak. I’m not sure if that’s coming from the Christianity side of the Asian side or whatever.
I was raised that way. It wasn’t like this whole thing like oh, I’m a parent and I’m going to stroke my kid’s ego and say, “Oh, you’re just fine. You’re very special, you’re really good at whatever you do.” Even though the kids sucks at it. Which I think also is an issue these days with some parents, that they push that. I wanted to clarify something. I know you talk about ego, and then there’s a chapter or so where you talk about pride separately, so the difference between the two. How can you define that very clearly between ego and pride?
Ryan: I’m defining ego as a collection of negative traits. I think pride, maybe undue pride is probably one of those traits. I think you raised a good point. Ego is not one thing. It manifests itself a little bit differently in different cultures. What I think is interesting is how often our smug pride and our egolessness is itself a form of ego and pride. We can think, if we think that we’re better than other people because we’re not other showboating, maybe those people actually aren’t showboating, they’re just striving for something better and you put yourself in a position where as a quiet person in the corner, you’re just judging everyone else. I try to focus less on other people and try to apply it more towards yourself. Is this who I am? Is this who I want to be? Am I being honest with myself? Am I being aware about my strength and weaknesses? Am I presenting myself in an honest, authentic way?
Jay: Now that you written this book, and I know you follow stoicism and all that. Do you find it at times difficult to not see everyone through this lens of, oh, this guy has an ego, like an ego meter on everyone that you meet and interact with, you know what I mean?
Ryan: When you write a book, you end up seeing the ideas in that book everywhere. That’s the only way you can make a book. Yeah, of course. People are like, yesterday I guess was the vote about Britain leaving the European Union. Everyone’s like, “Is this all ego?” It’s like, I don’t know. It’s not my expertise. Certainly not everything is ego. Sometimes things are stupidity. Sometimes things are … sometimes people are right to stand on their own and make decisions, I don’t know. I don’t think everything is ego, but I do think we are currently awash in ego and that it’s at the root of many of our problems.
Jay: Yeah, I think you’re right.
Ryan: Look, we have a presidential candidate in America who’s probably one of the most delusional, thin-skinned, arrogant, and at the same time utterly unqualified human beings to ever covet that office. That is the definition of everything that I’m talking about in the book. Bernie Sanders, is he similar to Trump in a lot of ways? Yes, but I don’t think it’s ego. I think it’s from a totally different place. You got to make those distinctions.
Jay: It’s funny because the title of your book is Ego Is The Enemy. I was thinking about, oh, I’m obviously going to do, it’s good because I’m going to try to give some of the books that I got away. Then I was like, oh, my boss could really use this book. Then I was like, wait a minute, this is difficult. This is not an easy book to give because literally as soon as you give it, someone sees the title and they’re like, “Hey, what are you trying to say here?”
Ryan: Yeah, that’s something I’ve certainly thought about. We tried to make different versions of the book where are open much more harshly and we realized that that was going to suppress people’s willingness to press it into others people’s hands.
Jay: Right. In the book, one of my favorite chapters is the Malcolm X chapter and the alive time, dead time thing. I relate to that so much, especially like I said, I’ve always had a day job and there have been times where I’ve just been miserable and I’m like, I can’t deal with this, I want to quit right away. Then I’ve always taken the more conservative path and been like, okay, I’m just going to collect this paycheck and side hustle it here. I think that’s, I love that chapter. I think that ties in a lot with the message that I want to get out there to some of these younger entrepreneurs. That also, you talked about this a bit as well I think in Obstacle Is The Way with regards to when you’re in this type of situation where you really hate your boss or whatever and trying to actually derive some value out of that experience as opposed to just being miserable, right?
Ryan: Yes. I mean, look, I got some very frustrating, bad news. I won’t get into it, but it crushed me in an unexpected way. I didn’t think I would care about it. I’ve just been so burned out from all the work I’ve been doing. It caught me off guard. I just got home from traveling. Oh, I’m just going to lay around all day. That dead time embodied, it’s like, oh, you hurt me by doing this thing and now I’m going to respond by wasting one of the days of my life when I don’t know how many days I have on this earth, that’s a terrible decision. You have to catch yourself.
What I didn’t do is what I sometimes do in situations is just throw myself into working, which is just a way of denying your feelings. I don’t think that’s productive either. I just said, “Look, I’m going to take it easy because I’m not feeling great.” I’m going to read. I’m not going to watch TV all day. I’m not going to sleep all day. I’m going to actually try to do something that if I had complete freedom over my day, like if I didn’t have any responsibilities, I would probably spend a good chunk of it reading. I’m going to treat myself in that regard. That alive time, dead time concept, which again is from Robert Greene, not mine. It’s taking a situation that could be wasteful and turning it into something productive.
Jay: Right. I think it’s brilliant. You talk about stoicism a lot. I think the first person that I was introduced that to, not the word but looking into the concept of stoicism more was obviously Tim Ferris. I know you … basically Obstacle Is The Way is an entire stoicism-based book. If you could just in one or two sentences for the layman describe what stoicism is, how would you put it?
Ryan: Stoicism is a practical philosophy that was popular in ancient Greece and Rome. That doesn’t really matter to anyone. I could give you the names. Marcus Aurelius, Seneca, Epictetus, Zeno, maybe you’ve heard of some of those names. It doesn’t really matter. I guess what I try to tell people is stoicism is a philosophy that basically holds as human beings, we don’t control the world around us. We control how we respond. It’s a philosophy around that singular idea. It’s very empowering if you can live your life that way. It seems disempowering, but in fact it’s very empowering.
Jay: Right, right. I think it’s such a unique way of reframing your mind and thinking about situations that if you can successfully carve out your emotions and actually believe that mindset, that it really, really does help. We’re coming up on the end here. I want to get one more question out to you. If you had one piece of advice that you could give a young entrepreneur, whether they’re coming out of college or they’re working somewhere and they’re doing the side hustle, what piece of advice would that be?
Ryan: Look, I think it would be hard to do better than that, you don’t control what happens to you, you control how you respond in terms of a life philosophy and piece of advice [inaudible 00:24:19], so the opposite of most advice out there. I guess if I was speaking a bit more practically I would say, look, you are in charge of your own education. No one’s going to magically teach you anything. You’re not magically going to pick up the skills that you need. If you’re trying to build your business, you’re trying to run a career or business on the side, the learning is what you need to be doing at this age. You’ve got time. You’ve got however long you’re going to work at it, however long you’re going to be on this planet. If it’s not built on a foundation of knowledge and experience, it’s probably not going to work out.
Jay: Right. Yeah, the one actionable thing that I’ve always told people is read. I know you’re a huge, you read [firstly 00:25:12] as well and you have a reading list and whatnot. I think the amount of stuff that you can learn, I guess I was writing this fitness book and I was like, look, I’ve spent 15 years of my life trying to decode fitness. I’ve finally done it and condensed it into 200 pages or whatever have you. It’s like, if you can get someone, 15 years of experience in two hours of reading, why wouldn’t you?
Ryan: Totally. I have a quote in [inaudible 00:25:43] from Bismarck where he’s saying any fool can learn by experience, I prefer to learn from the experiences of others. If you’re not living your life that way, then you’re the fool.
Jay: Right, brilliant. Okay, Ryan, thanks so much. You’re at RyanHoliday.net, right?
Jay: That’s your personal I guess homepage. I will direct listeners there. We’re going to have this, it’s going to roll out in probably the next couple months, probably six weeks. I’ll definitely send you an email and link you up. I don’t know if you’re … are you ever in Asia or have you ever done any sort of work in Asia?
Ryan: I gave a talk in Thailand in December. Other than that, I’ve not been out there much.
Jay: Yeah, so Hong Kong is kind of a unique place because first of all everything’s so slow out here. One of the reasons why were doing this podcast is that, look, podcasts have been around for over 10 years and really popular, and no one does them out here. I was like …
Jay: Yeah. I’m working with Invest HK, which is part of the Hong Kong government. I’m like, dude, we got to get on the ball here. No one is doing this. This is so great. It’s content that can be there forever basically and anyone can access it. This is my big push. I’m trying to get this out there. Yeah, if you’re ever, I’d love to have you out here at some point in the future. If you’re ever in town or in Asia, definitely drop me a line. It would be great to catch up with you. Thanks so much for your time, Ryan. Congrats again on the book. I wish you all the success.
Ryan: All right, good luck with your show.
Jay: All right, thanks, man. Talk to you later.
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