Episode 048: Ryan Holiday - Conspiracy

Legacy of Monsters an Apple Original series. The world is on fire. I decided to do something about it on November 17th.

This place.

It's not ours. Believe me. The most massive event of the year arrives. If you come with me, you'll know everything. I promise.

Oh my God.

Go, go, Go. Legacy of Monsters streaming November 17th only on Apple TV plus Apple Card is.

The credit card created by Apple. You earn 3% daily cash back up front when you use it to buy a new iPhone, 15 AirPods or any products at Apple. And you can automatically grow your daily cash at 4.15% annual percentage yield when you open a high yield savings account. Apply for Apple Card in the Wallet app on iPhone. Apple Card subject to credit approval. Savings is available to Apple card owners subject to eligibility. Savings accounts by Goldman Sachs Bank USA member FDIC terms apply.

This is the Rise of the Young podcast, bringing you insights from the most innovative entrepreneurs and influencers of this era. Hosted by 17 year old entrepreneur, author, public speaker and branding expert, Casey Adams. Now let's get right into the show.

What's going on, everyone? Casey Adams here. Welcome to the Rise of the Young podcast. Today we have a special guest. I'm sure a lot of you guys know who he is. We have Mr. Ryan Holiday. Ryan is a media columnist, marketer and best selling author. And his recent book Conspiracy is something that I really want to share with you guys today. So Ryan, I really appreciate you coming on.

Thanks for having me.

Absolutely, man. So, I mean, first off, man, whenever I have people on my show, obviously time is a super important asset. But for everyone that may not know who you are and, and where you grew up, I'd love for you to share about that, man.

Sure. So I dropped out of college when I was 19. I ended up with a job at American Apparel, the clothing company. Became director of marketing by the time I was 21. Wrote my first book at 24 and by 30, I'm on number seven. Sold about a million copies worldwide in 30 languages. And just sort of doing the thing I always thought I would, I wanted to do. Which was. Which was be a writer.

That's amazing, man. I know that. I've done a lot of research on your story. I've seen a bunch of your different interviews with Gerard Adams and Tom Bilyeu and all these amazing people, man. But my question that I really wanted to ask you, man, and I'm sure you wanted to touch on this as well. So when it comes to just writing, I know I've read a lot of your books as well. And what age, like, did you start writing at? And has that always been a main interest for you?

I think I always loved writing. I was a huge reader. But the idea that I could actually do that for a living, that took a lot longer for me to realize. I guess none of my parents, friends were professional writers. It seemed like this thing that special people got to do. It wasn't until I started meeting the people that, whose books I liked. You know, in college I just started sending emails to writers that I admired and I started talking to them. And it was from that I kind of realized, oh, wait, these are just like people. And this is a job like being an insurance broker or a car salesman. I mean, it's a cooler job and I think it's harder, but it's not. It's not like, I don't know, it's not like being a movie star or something. It's attainable. And so that sort of breakthrough was really important for me, just realizing, like, I think I could do this.

Yeah, for sure, man. So, I know regarding you said you dropped out of college when you were 19 and then you started working with Robert Greene. So, like, that entire experience, what was like the biggest thing that you learned from that and how did that experience even come about?

Well, I think the big, the sort of meta lesson for me that I try to share with other people is like, if you want to do something, find someone who is doing it and learn everything that you can from them. Robert Greene is probably my favorite living author. And so being able to be his research assistant, getting to sort of learn at his feet was not only an incredibly cool experience, but it let me jump ahead in line in a big way. It let me learn directly from the source rather than trying to figure out a lot of things by trial and error.

For sure, definitely, man. So obviously, when it comes to just the books that you've been able to produce, this is something I was super curious about and I'm sure everyone listening would find value in. So when it just comes to a book itself, I mean, you've had amazing books that you've written. What's your process of writing a book? How does the idea originate, and what's the process from start to finish for you?

Well, you have lots of ideas for books, right? Not every one of them actually deserves to be made or could even be made if you were to try. So I think part of it is just sort of filtering the good ideas from the bad ideas. To me, it's sort of, I want something that I'm super interested in that. I feel deeply passionate about that I feel like is meaningful and important, but then also is going to have a realistic chance of helping people. On the other side of the transaction, people are purchasing a book and so it's got to deliver a lot of value. And then ideally they like it so much they recommend it to other people. So I see a lot of people going, oh, so and so is doing this. So I'm just going to copy them. And they're not actually making something that's like better or new or fresh or different that really satisfies that criteria. So I always try to think like, look, has someone done this before? Are there a dozen other similar books to this one? And if the answer is yes, then like, I've got to keep thinking, I've got to keep refining my ideas until I have something fresh and different.

Definitely, man. So that's super cool because I feel like especially I've read a lot of books and I'm sure you have as well. But so whenever you're just so I can regroup and rephrase on this. So whenever you start to write a book, is that a process that takes months to kind of cultivate those ideas or what's been your experience with just like the time frame of it?

Well, every project is different, but I'm always thinking about what my next idea is. So it's just sort of marinating in the back of my mind until it's ready. And then, yeah, in publishing, you make a proposal, you sell that proposal. So you got to go out and get other people's buy in. You've got to actually sort of make this thing viable and workable and get other people's support. So it's the first part, the hardest part is coming up with the idea. And the second hardest part, like you have an idea for a company, if you can't get investors, that might be a sign that there's something wrong with the idea. So to me, it's this sort of interplay between those two things. And then you sit down at your computer and you work day after day until you make it real for sure.

Like you said, day after day. Because I know writing a book obviously requires tons of patience. So when it comes to just the process of day by day, are you someone that when you're writing a book, is it something that you literally do every single day or do you have periods that you just dump your ideas? How does the writing portion look for you? I'm super interested in that.

So I'm Always writing. I'm not always writing a book. So I try every day to sit down and do some level of writing, some serious, sort of quiet, contemplative, creative time. You know, sitting down in front of a blank screen, writing a book is more. Is that, you know, probably cranked up a few notches because there's a very specific thing you're doing. You have deadlines, you have very specific parts of the project that you have to nail down or you can't move forward. But I'm always writing. I think if you're just sort of going around, like, expecting inspiration to sort of get you through, I think are going to be misguided. And I tend to be nervous. For instance, I'll hear people go, you know, I'm going to Paris for two weeks to write, or I'm traveling, you know, to a vacation house for a month, and I'm just going to write. I don't like that. To me, I'm much more of a. You do it every day. You build a routine. You know, you inch your way there. I think trying to do it in some sort of stuff. Sprint is typically misguided.

Definitely. Man, that's super cool. That's definitely a cool outlook. But I wanted to ask you, because I know you were the director of marketing at American Apparel for a long period of time. So with that entire story and chapter in your life, like, how did that kind of cultivate and with you being a marketer, how did that transition in your life unroll?

Well, look, I think marketing is an underrated skill, particularly if you want to be a creative person. Right. If you have great ideas, you make great art, or you have a brilliant business idea, if you can't sell that to the world, you're screwed. The idea that just like, oh, I'm going to put up this Instagram account and it's magically going to get a million followers. That's just not how it happens. You got to know how to sell yourself and sell your work. You know, working with a company that was controversial, that was provocative, that was sort of lean and creative and willing to try new things was really great. It's also a cautionary tale. You know, there's a company that was at one point worth over a billion dollars, and now it's not. So I learned a lot of what to do on the marketing side and a lot of what not to do on the leadership and marketing side. And so I've tried to take those lessons. And now that I work for myself and I have my own Projects. Try to. Try to do better.

For sure, man. So what age did you get the position of director of marketing there?

I think I started there when I was 20 or 21, and I don't remember the. It wasn't like a, you're officially the director of marketing. It was a slower process than that. But by the time I was 21 or 22, that was. That was my position. And I. I held it until I was, I don't know, 26 or 27.

Okay, cool. Yeah, you had some good time there then. So when it comes to you dropping out of college, man, because for me, I have tons of young listeners, and I myself, I'm 17, still in high school, actually. But when it comes to your mindset of when you dropped out of college and you actually going to college, I love to ask my guests to just, what's their mindset on college and how did it play a role in your life? And then what. What was the main trigger for you to really just pull the trigger and drop out?

Well, I think college is a great default, provided you're not running up a ton of debt that will be hard for you to repay. Right. So if your parents are paying for college, great. You should go. You should try to use it as a place to figure out what you want to do in life. If you're not sure what you want to do in life and you've got a scholarship, great. You know, I wouldn't. $200,000 for a college education to then hopefully, at the end of it, maybe know what you want to do with your life. That's tough. You could have learned a lot of those lessons a lot more cheaply if you'd been a bit more disciplined and patient. For me, college was great. I loved it. I learned a ton. I met great people. I learned things about myself. But I was going to college to be a marketer and to be a writer. And the relationships that I made and the gigs that I'd gotten while I was there took off quickly enough that I was able to leave and get started in the same way that Mark Zuckerberg wanted to be an entrepreneur. He starts this company at Harvard. What, is he going to put the company on hold to finish at Harvard? That's ridiculous. You can always go back to college. You can't always get a moment or an opportunity back.

Definitely. Definitely. I totally agree with you on that. And that's something I feel like after having a ton of people on my podcast, man, I feel like that stipulation of just the now Factor of like, what are you getting going to do now and what are you sacrificing in return of going to college or not. Right. So for you, man, I know that you said you were 19 when you dropped out. What year was that for you?

This would have been 2007. And I guess, you know, I've written a lot about dropping out of college, and so I hear from lots of kids that are thinking about it. I think, to me, dropping out of college, going to college and not knowing what you want to do is not great. Dropping out of college and not knowing what you want to do is even worse. Right. So I hear a lot of kids are like, oh, I'm not doing well in school. I don't really like it. I'm going to drop out and then I'm going to figure it out. You probably won't, you know, if you can't figure it out while you're in college, while, you know, you've got your living expenses paid for, while you're surrounded by, you know, these great books and libraries and interesting classes, you're probably not going to figure it out when you're, when you move back home with your parents. Right. So it's important that if you do leave college, in my opinion, you're leaving it for something that's better than college.

Yeah, for sure. Like actually having a route to pursue rather than just jumping out and diving into deep end.

Yeah, yeah. Don't jump off the cliff if you can't see where you're gonna land.

Yeah, yeah, for sure, for sure. That's a total agree with you, man. So when it comes to your backstory, man, like before college, before you started getting all these positions with different people, what was your life like when you were in high school and when you were like someone younger, were you always someone that was optimistic about entrepreneurship or. I know that you spoke, spoke about writing, but when you were in high school, let's say, because I know a lot of people listening are in this stage of their life. Where were you at during that phase and what was your mindset back then?

I feel like I was really, really average. I don't, I don't think I. I don't know how much potential I showed. I don't think my parents thought I was gonna do much. You know, I got along well with some of my teachers, you know, not other teachers. Like, I was just very middle of the road. But, like, I knew I wanted to do something different. Like, I knew I didn't want to have an office job, my Whole life I knew I wanted to be creative. I knew that I loved books and I wanted that to be a part of my life. And so I was just really still figuring it out. And so the idea that you don't have it figured out or that you have to have it figured out right now at 16 is just ridiculous. I'll give you an example. Sometimes people go, if the 16 year old version of me could see me right now, they'd be so disappointed. No offense, but like when I was 16 or 17 even like I was an idiot, like I didn't know anything. So like, you're gonna evolve and grow and you still have a lot to learn and see and so like, don't. It's like you, you shouldn't expect that you'd have this thing that many adults haven't figured out. You shouldn't expect that you'd have it figured out by 17. And I. And I know I didn't.

Okay, for sure. For sure. So when it comes to like everything you do now, man, and just the routine you're in. I had Dean Graziosi recently on my podcast and he talks a lot about just his daily routine. And that's something that I always like to ask people on my podcast. But is there something in particular that you see yourself doing that helps you stay focused and helps you stay aligned with what you're working on day to day?

Yeah, I get up early and I get to work every morning. That's like, I do the important things early in the day, right. I have a to do list, maybe four or five things. I'm crossing them off. I'm leaving time to be creative early on. That's important to me. Two things I wish I'd maybe discovered earlier. In high school, I ran track and cross country and I just hated it. My parents made me do it and I hated it. And now I willingly run every single day. So I always laugh about it. But the idea of having some sort of form of exercise, something that pushes you, that you're challenging yourself with. I have a lot of my best ideas when I'm running. And then I go for a long. Every morning I journal and I go for a long walk. And this sort of helps me ease into my routine as well. And these are things that I, you know, I was resistant to at first and they really work. And I wish that I had been more open minded early on.

Okay, cool. And then something that I also like to touch on with a lot of people. So when it comes to just morning, I know how you said, like, that's the most creative part of your day. And I know that some people say, hey, like they don't go on social media for a certain amount of hours. Is that something that you tend to do in the morning as well?

Yeah, I try not to get sucked immediately into email. I try to, you know, work. I try to get that important creative work done. And yeah, that's super, super important if you're just immediately getting sucked in to social media and random crap that happened while you were sleeping, like your friends drinking or what some celebrity tweeted or what the president said, man, you're playing from behind already. And that's not a great position to be in.

Definitely. Yeah, definitely. That's something I've been doing for the last months now. Just really trying to disconnect in the morning. And I feel like a lot of people that have my podcast, they sort of have that same mentality that just start with creativity. And I love how you said that, man. So I recently had your team, they sent me one of your copies of your books, man, your new book, Conspiracy. I was just reading through it, man, but I really wanted to talk about that because I know that's something that you recently put out there. And I'd love for you to share a little bit about the process of creating that book and kind of what it's about and what's the purpose of writing it and what's the purpose you want to get to the audience?

Yeah. So to me, it's this incredible story of this billionaire who sets out to destroy this enemy, this media outlet that had cruelly outed him as gay 10 years previous. And I think, I mean, if I was your age, I would study someone like Peter Thiel. He's someone who's been, you know, a contrarian, who's been right about a lot of big topics. He wrote a fascinating book called Zero to One. I'm just fascinated with him as this sort of representative figure of our time. And so to me, Conspiracy was about this, you know, unusual, distinct, almost freakish person who had this theory that he could do this impossible thing. And, you know, some people are going to think that the thing he did makes him kind of like a James Bond villain. But I actually think that what he did is much more complicated and nuanced than that. And so the book Conspiracy is this sort of meditation on what it means to try to be powerful and have power and to try to shape the world in your image.

Okay, yeah, cuz I was reading through it, man. I just the work that you're put into your books, man, like, it's just something that whenever you, whenever you put out a book, man, I always, I get it and just read it fully. And I just think that's something that a lot of people don't have that skill set. And that's why I was so honored to have you my podcast, because the way you just drag people right into the book, I think it's just such an amazing way that you're right. And it's definitely been something that's impacted my life really heavily.

Well, thank you. No, I appreciate that. I think this is again, an incredibly unreal story.

Like.

The Adam is gay and he just steps back and he schemes and he plots and he waits for almost five years and he's waiting for the perfect opportunity. Like when I was 17, the idea of waiting like five minutes for anything was like inconceivable, you know, and he waits for five years and he finds the perfect opportunity. Gawker runs an illegally recorded sex tape of the wrestler Hulk Hogan. And he sees that that's the perfect thing he can use and he spends $10 million of his own money funding this lawsuit on Hulk Hogan's behalf in secret. And again, Gawker still doesn't even know that Thiel is doing this. And he's just patiently working behind the scenes. He's waiting. It takes four years from the time he files the lawsuit until he gets the verdict and then boom, he's done it. They go bankrupt. It's $141 million judgment and then the rest is history.

For sure, man. And for everyone listening, that will definitely be the link down below for this podcast interview. But we'll. One more thing, man, I have a couple more questions. So when it comes to this book in particular, I know I've read Ego is the Enemy, all of your other books in particular, but something about this Nuon really stuck out to me because obviously it's about a story that you covered, something that was interesting to you. How did that topic and book idea. I know that we talked about that in the previous part of the podcast, but how did this all come up? Is this something you've always been interested in in this story? Or what was your reasoning and purpose for just analyzing this entire process of these individuals lives and really writing a book about.

Is funny how life works. You want to be open to opportunities. Because when, you know, I just got a random email from Peter. He read something I wrote and he said, hey, we should get dinner sometime. And I could have ignored the email I could have not seen.

I.

This random email turns into a year and a half later, this book that I'm very, very proud of. And so you want to be open to opportunities and you want to be open to the fact that oftentimes opportunities don't look like opportunities at the time. They just look like an email or a phone call or you bump into someone or you have a little idea. And so it was obviously a story I was fascinated with. But I didn't know if I could do it as a book. I didn't know if they would let me. I didn't know if I had what it took. But I, you know, I rolled the dice and it worked out.

That's super cool, man. So it was just an email that literally came randomly or you guys chatted and then it just, over the course of communication and meeting is turned into something much bigger.

Yeah. And I tended to find that a lot of my things in my life have gone that way. They start small and they evolve and grow very rarely. It all spelled out to you in advance for sure.

That's super cool. That's. I didn't even know it was like that. It's awesome. So even for me, man, cuz like I had like two years ago when I first like met one of my mentors now, Gerard Adams, like one person that happened from an Instagram DM or even how you're on my podcast now is just a simple Instagram dm. I think a lot of people, especially the young people that follow me, like they, they try to look for the big things, but they don't take into consideration the little things like an email or DM and how powerful it can be when it comes to what comes from that, you know?

Completely, Completely. And you've got to be open to experience and open to taking chances. And then when you get a chance, you gotta, you gotta work your ass off and turn it into something definitely for sure, man.

So regarding that, I know whenever people hear the word success and especially the younger generation versus the older generation, everyone has different outlooks on it and just I feel like that word is just thrown around in different ways all over the place. But for you, Ryan, I'd love to kind of hear your intake on what is success to you and what is fulfilling when it comes to just your day to day lifestyle, you know?

Yeah. To me success is about freedom. If your success means that you're always busy, you never have time to do what you want to do to be the person you want to Be to express yourself in the way you want to express yourself. That's not really success, right? That's just a form of imprisonment. For me, success has always been, am I getting more or less free? And so that's always been my test. What do I want my life to look like? Where do I want to live? How much do I want to work? What do I want my relationship to money to be? Am I able to say what I want to say or think what I want to think or dress how I want to dress, make my own hours, whatever it is, that, to me, has always been the important sort of metric for success. So there have been times when I've made more money, but I've been less free and in most cases, less happy. And then other times where maybe I wasn't doing as well financially, but my life was exactly how I wanted it to be. And so I'm always trying to find the right balance with responsibilities and family and things like that, but trying to find the right balance there and get to where I'm happy, for sure.

Man, That's. I totally love that reasoning. So when it comes to just. I have two more questions for you before I let you go, man. So when it just comes to daily routines, I know that you talked about that, but whenever people come on my podcast, I always like to give them three practical things. When it comes to just giving that someone could take away today from listening to this. So when it comes to writing for you, but not just writing the books, but just your journey from marketing, from writing books to meeting all these amazing people and interviewing and being on these shows, what has been just the three biggest takeaways that you've had throughout your journey when it comes to just being an entrepreneur and working for yourself?

Well, to me, journaling is really important. I do it every morning. I've actually made my own journal. It's called the Daily Stoic Journal. I do it in the morning and at night, but it's about setting your intention every morning and then reviewing how you did with that. So, like, not just winging it, not just hoping you're making progress, but actually spending some time with some free association, just writing, putting the thoughts out on paper and actually reflecting on how you're doing. To me, that's helped me grow by leaps and bounds. It's been an important part of my routine. You know, I think, you know, taking care of yourself, being healthy. Like, I try to sleep eight plus hours every night. I'm not. I think if I'm. If I'm Pulling an all nighter. It's because something has gone horribly wrong. Like I don't think, I don't think it's cool. I don't think it's glamorous. You know, I don't think it's, it's like a sign of success. Like I want to, I want to have like a normal life where I get to work the hours that I want to work.

Yeah.

And then, and then I'm trying to think what else. You know, I would say probably one of the most seminal things in my life, routine wise. And I've been with my now wife since we were about 19 years old. We only got married about three years ago, but we've been together that whole time. And I think when I was young I maybe thought that relationships and success were mutually exclusive or that relationships would hurt my chances of being successful. And the truth is like having this person who was on my team who understood me and we were together was really, really important for doing what I was doing. So I would just urge people not to write off having a relationship just because, you know, Tinder is easier or because they think it's not cool.

Yeah, for sure. That's some good stuff. You don't hear that often, man. That's definitely something that super unique. So last thing, man, I know that you've dropped a lot of bombs on this podcast and I definitely appreciate you being on, man. But regarding, I know that you've written a lot of best selling books, but on the flip side, what has been a book that has really just impacted your life so much and just something you'd want to share with the audience when it comes to just a book that has impacted you that you'd want to share with the audience today.

I'll give you a couple. So I think everyone should read Robert Greene's the 48 Laws of Power and his book Mastery. Both of those are super important. I think you should read what Makes Sammy Run. It's one of my favorite novels. And then I would encourage everyone to read Steven Pressfield's the War of Art. I think those four books, if those are the only books you read in your whole life, I think you'll be a better person for it.

Wow. Okay, man. Really, I really appreciate you chopping that, man. I've heard a few of them. But honestly man, like I said at the beginning, I really appreciate your time coming on here. And for everyone that does not follow Ryan or hasn't gotten his books, all of that information will be down below in the make sure to DM him, go check him out on Instagram, go get a copy of his new book, Conspiracy. I'm reading it myself right now and I'm only about halfway through it and it's just amazing. But Ryan, honestly man, I really appreciate you coming on. You've added so much value to not just my life, but thousands and millions of other people. But thanks so much, man. We'll definitely stay connected.

Thanks for having me, dude.

Absolutely, man. We'll talk soon. Thank you so much.

Monarch Legacy of Monsters An Apple Original Series the world is on fire. I decided to do something about it on November 17th. This place, it's not ours. Believe me, the most massive event of the year arrives. If you come with me, you'll know everything. I promise.

Oh my God.

Go, go, go. Legacy of monsters streaming November 17th only on Apple TV. Plus.