Ryan Holiday, Author, “Ego Is The Enemy”
Mastering Adversity – An Interview with Ryan Holiday
Ryan Holiday, strategist, media manipulator, and marketing genius, is the author of Wall Street Journal best-seller, Trust Me, I’m Lying: Confessions of a Media Manipulator (2012).
Foundr caught up with Holiday to discuss marketing, hustle, and his latest book, The Obstacle is the Way (2014).
At just 26 years old, Holiday has already had a career that most people would kill for. He has worked as the director of marketing for American Apparel, written a best seller and strategized for exclusive clientele and mentors including Robert Greene, Tim Ferris, and Dov Charney. And if that wasn’t impressive enough, Twitter, YouTube, and Google are now using Holiday’s strategies as case studies. He’s also a prolific reader and works as a partner at his own marketing agency that represents authors, brands and public figures.
His latest book, The Obstacle is the Way argues that we all face adversity, but it’s how we respond to it that determines whether we achieve greatness and growth, or failure and obscurity. In it, Holiday looks to the stoics, ancient generals and some truly amazing historical case studies to learn how we can approach adversity and achieve lasting greatness. The result is a bold and powerful manual showing how others have turned their darkest days into catalysts for growth, fame, and opportunity. And in turn, how you can too.
Ryan told us that the inspiration for the book came from the great Roman Emperor Marcus Aurelius who once said, “The impediment to action advances action. What stands in the way becomes the way.” or as Holiday puts it more simply, “The Obstacle is the Way.”
Everyone faces obstacles, both professionally and personally; it’s part of this thing called life. However as an entrepreneur you can definitely expect more challenges than the average “office Joe”. So it’s something you need to understand, expect and prepare for.
So, what is adversity – is fate a miserable bastard, or is life just an up-hill battle… all struggle and then you die? We were keen to hear Ryan’s insights on how we, as entrepreneurs, can understand and deal with it.
Turns out, much of the friction in our lives that we call ‘adversity’ isn’t some cosmic force or bad juju, it’s actually caused by our perception of what happens to us and around us.
Ryan spoke with us about three things clash and cause friction in our lives:
- The way we want the world to be
- The way we think the world should be
- And, the way the world ultimately turns out.
He explained that it’s the disconnect between these things that causes everyone to face adversity, from minor challenges to major obstacles. It’s a resistance between what’s happening and what we want to happen that causes this experience.
However, there’s no need to despair, a season of hard lessons and dealing with frustrating obstacles could actually be the catalyst for you to change and grow for the better. Holiday told us that it’s all about how you choose to react: “In every one of these instances, you are faced with a choice: you can decide to see it as challenge and as an opportunity to practice excellence in some way.”
The first action step in dealing with any adverse situation is to hit pause on your emotional freak-out. Holiday pointed out that most people waste untold energy in their initial reaction by stressing out about things they can’t control. By avoiding the tantrum, you’ll be surprised by how much more energy you’ll have to instead channel into problem solving. Importantly, “ adds up over time, making you stronger and better each time you face a challenge.”
The next step Holiday recommends is “a simple mindset shift… It’s always remembering that you don’t control the world around you – you only control how you respond to it.”
Responding to adversity: Holiday uses Demosthenes as an example of excellence in the face of overwhelming adversity.
“He was an Athenian orator who was born disabled – he has a speech impediment, his parents die, then his guardians steal all of his money and you would think that that would be the kind of thing that knocks a child on their ass – and in a way it did – but Demosthenes decides instead he’s going to teach himself the law, he’s going to overcome his speech impediment, he’s going to challenge them in court to win back the inheritance that the guardians had stole from him and it’s almost like a movie.
It’s this training montage: he goes underground, he shaves his head so that he is too embarrassed to go outside and instead becomes so knowledgeable and so skilled in public speaking that when he eventually challenges them in court, he wins and in the process he becomes one of the most influential speakers and politicians in Athens.”
So when you next receive a frustrating e-mail, or a problem hits your desk, don’t waste mental and emotional energy reacting to things outside of your control or blowing up about it, just skip straight to dealing with what you can change and begin to problem solve. And as Ryan recommends, look to the greats and view each situation as an opportunity to practice excellence
We couldn’t let a master of marketing go without asking for some tips on how to approach branding and positioning. Holiday has repeatedly engineered internationally successful marketing launches for authors and entrepreneurs alike, so what does he do differently? He told us that he often looks for the gaps that everyone else has missed.
“I try to take advantage of whatever everyone else is failing to…”
And when it comes to finding an interesting marketing angle, Holiday tries to think about something that:
• “No one else wants to do”
• “No one else has thought of”
• “Or something that’s interesting and unexpected”
So before you follow the crowd and try to ‘model’ the rest, take a leaf out of Holiday’s playbook and look for a fresh hook that others have overlooked.
How to Hustle like Holiday
Finally, we were curious as to how someone as young as Holiday had achieved so much and how he maximized his hustle.
He told us, “I think part of the hustling is having a goal, whether you can articulate it or not. I also think it’s not so much caring about the results, but liking the hustle. Athletes that love practice are the ones who become excellent. And for me – I love the hustle, I love the work, I love coming up and doing things, I love this road, the chase. I love that. And I love it because it depends on me.”
- The secret to driving attention to your business with social proof
- How to pitch journalists and bloggers from major media channels
- The importance of self-reflection and humility in order to succeed
- What works and doesn’t work when it comes to successful PR
- Where to go and what to do when you need a mentor
Full Transcript of Podcast with Ryan Holiday
Nathan: Hello and welcome to another episode of the “Foundr Podcast.” My name is Nathan Chan, CEO and Publisher of “Foundr Magazine,” and I’m coming to you live from hometown, homegrown, Melbourne, Australia. Hope you all are having a wonderful day wherever you are around the world, really pumped about today’s guest. He’s kind of like one of my personal heroes, this guy. His name is Ryan Holiday. Been following his work pretty much ever since I started “Foundr” in 2013 and yeah, we really connected on this episode. It was really cool and we talk to Ryan about all sorts of interesting things. He just released this amazing book called, “The Ego Is the Enemy,” and, you know, what I found was really awesome. Is with full transparency, guys, you know, sometimes I’ve struggled with this where it’s easy to drink your own Kool-Aid and we’ve been guilty with this at “Foundr.”
You know, the brand has grown at a reasonably good pace and constantly people, you know, tell you that you’re doing an awesome job and sometimes you start to believe that and you start to buy into your own hype and that’s when you make mistakes and that’s something that I’ve personally found and I always have to try and keep myself in check and it’s something that’s really, really important for an entrepreneur. I think as time goes on and, you know, once you start kicking some goals, sometimes things can happen where you start to, you know, believe in your own hype and that’s something that I wanna be really, really careful of, and me and Ryan had a really amazing discussion around this piece but not only that.
Like Ryan is a serious marketing guru, PR, just a weapon. He knows how to yield the media to his…you know, to however he wants it pretty. This guy’s a marketing genius and he’s behind, you know, a lot of really, really successful marketing campaigns. He used to work for American Apparel, he’s done all sorts of crazy stuff. He used to do Tim Ferriss‘… some of his book launches. He has a really successful book marketing company. So we talk about all things marketing and PR, so if you guys are interested in PR, you guys are in for an absolute treat. Ryan does not hold back and he’s just a really, really great guy and I had an awesome conversation. I hope that you can really draw a ton of gold from this one, I certainly did. So that’s it for me guys.
If you are enjoying these episodes, please do take the time to leave us a review. Please do check out, you know, some of our other fruits of our labor, like the magazine or, you know, just sign up to our newsletter. Check out the free Richard Branson issue, check out Foundr’s Club. We’re working on a ton of cool things, we’re working on a physical coffee table style book which I’m really, really pumped about. Me and the team, we’re gonna work on something awesome. So if you’re enjoying these interviews, you’re gonna be reading the best of soon. So if you wanna know more, sign up at foundrmag.com/book. I know you guys are gonna love this one. But anyways, that’s it for me, now let’s jump into the show. The first question I ask everyone that comes on is how did you get your job?
Ryan: Well, I guess I would have to think about what job you’re referring to. As a writer, the cool part is no one gives you that job, you just sort of take it. I started…I was a research assistant for a writer named Robert Greene which is how I learned how to write. I started a blog which no one gave me permission to do. I just started doing and over time, I built up an audience and that gave me the opportunity to eventually get a book deal and then I’m now on my, I guess, my fourth or fifth book. As a marketer, my first real marketing job was for American Apparel where I went on to become the director of marketing and there, I got a journal from the owner of the company. So I’ve definitely not played by the rules in terms of getting what I have gotten, I’ll say that.
Nathan: So you’re fairly young. How old are you, Ryan?
Ryan: I just turned 29.
Nathan: Oh, gee, same age as me, bro. Oh, awesome.
Ryan: Nice. Congrats. Good age.
Nathan: Thanks. Yeah, it is good. We’re trying to get so much done before we hit 30, hey?
Ryan: That’s exactly right.
Nathan: Yeah, well, look, it’s safe to say I think you’ve done a lot more than me, but let’s talk about that. So I know you didn’t finish college, is that correct?
Ryan: Yeah, actually I dropped out to work for Robert Greene. I was sort of looking at it like, hey, this is the kind of thing I would have been ecstatic to get if I was graduating tomorrow, so why am I gonna stay in school for that? So look, one of the secrets, I think, to doing things young is to sort of pushing up the timeline. So, you know, instead of getting my first real job when I was 22 or 23 the way that a lot of my friends did, some of them even waited longer because the job market was so terrible in 2008/2009, but I started when I was 20 or 19 even. So I started early and that’s given me a head start certainly.
Nathan: So, you know, you strike me as someone you’ve written quite a few books, “Trust me, I’m Lying,” that was a killer book, “Growth Hacker Marketing,” “Obstacle Is the Way,” and now your new book, “Ego Is the Enemy.” So you strike me as someone that is obsessed with learning and I cannot even begin to imagine how many books that you have read, but I really just wanna delve a little deeper like where does that, you know, insatiable hunger that you have for learning come from that we see in your books right now? Have you always had this as a kid growing up? You know, what was life like growing up for you?
Ryan: I think I always really liked learning. I mean, I was obsessed with reading as a kid although mostly what I read were like Westerns and James Bond novels and stuff like that. So I wasn’t exactly learning, but I loved reading and I loved getting lost in books which I think is its own, you know, sort of form of entertainment and learning. But one of the big weird things for me that sort of made me so into learning is when I left college, I was very honest with myself about what I was giving up, right? Like I’m giving up having to go to a class every day and having a really smart person care whether you learn something or not, which would be the professor and the TAs and all that sort of stuff. So in leaving college, I sort of had told myself like, “Okay, if you’re gonna do this, then your education is now your responsibility. Like you’re gonna have to learn and keep learning to make up for the fact that you’re not gonna have the same base of knowledge as everyone else.” So I sort of think about it that way and then, well, look, I’ve just found out and I’m sure you agree, I’ve found that the more that I go out and learn stuff on my own, the more opportunities that creates for me and the better I am at my job. So I don’t see it like, oh, learning is this hunger that I have and it’s fun, although it is. I see it as like, hey, the more books I read, the more money I make and the more interesting people I meet and the more opportunities magically come my way.
Nathan: I see. So there was no… Did you have some pivotal moment where everything changed for you where you were just like really into strategy learning, reading, is kind of just kind of developed over time?
Ryan: Definitely developed over time. I do remember I was with the girlfriend that I was with in high school and we ended up going to the same college together and she dumped me maybe the end of my freshman year. And I remember I had this Amazon wish list of like books that I’d always wanted to read that I’d sort of put off reading but I never had the time for. And I remember, you know, one day I was probably just in my room crying or something and I said, “Well, I’m not gonna do this anymore. I’m gonna go to the store and I’m gonna read all the books that I’ve been meaning to read.” And I bought, you know, like a huge stack of them and I just, one by one, went through them and then when I was done I read more. So it was sort of like I’ve been putting this thing off and I got really serious about it when I was sort of at a moment of personal crisis.
Nathan: I see. So your first kind of apprenticeship or way you started learning because, you know, I know you’ve worked with Tim Ferriss, you helped with “The 4-Hour WorkWeek” with that book launch, you helped Tucker Max, you also helped and worked with Robert Greene as a research assistant. I think you’ve helped with a lot of PR and marketing strategy and now you’ve got your own book marketing agency, you’ve worked with a ton of impressive really, really impressive clients. You know, your strategies are wrote about or used as case studies by Google, Twitter, all these all other big companies. So where does all this strategy, where do you get marketing chops from, man?
Ryan: That’s a good question. I don’t think I was born with them, obviously. You know, working for someone like Robert, who’s I think one of the greatest strategic living minds, was obviously a huge part of it. You know, you just sort of learn by osmosis around him and then I learned a lot from Tucker who’s a great marketing mind. Even at American Apparel, although I was doing the marketing, was a sort of a natural born genius marketer. So I was always around really smart people who were instructing me and teaching me and they were paying me to learn essentially, right? They were saying like, you know, “You have a natural aptitude for this, but like here, go do this or have you thought about this?” So I learned a lot that way, but a huge part of it was just what I learned on the job, is sort of being, you know, working for internet authors who didn’t have really any…they didn’t have huge budgets, but they also didn’t have anything to lose, right? They were willing to try an experiment. Gave me a chance to do things that maybe I couldn’t have done if I was working for a Fortune 500 bank as a marketing intern or something like that.
Nathan: I see. So were you responsible for a lot of like the cool kind of stuff that American Apparel have done? Do you still work with them or not anymore?
Ryan: I don’t work with them anymore, but I was the Director of Marketing for like six plus years so I was involved in a ton of their really cool campaigns. What’s so cool about a company like American Apparel is that it’s vertically integrated so it does all of its own marketing, advertising, PR, design, all of that. There was a great team of people and they were all involved but it was… What was cool about that company is like there was almost nothing that we couldn’t at least try and so we did a lot of interesting experiments. Some of them worked, some of them blew up in our faces and, you know, it was all over the news and we got in a lot of trouble about it. But, you know, we could try just about anything because it wasn’t like formed out to some agency who did it all for us.
Nathan: Gotcha. So it was all in-house. So actually, let’s talk about some of these campaigns that you’ve been behind the scenes kind of architecting, strategizing because I think people would really find that interesting and they can get a real grasp of your marketing chops. Yeah, can you just tell us like, you know, maybe two or three of your favorite coolest like, you know, I don’t if you call them growth hacking PR campaigns or whatever. So yeah, that makes it. So you’ve got a lot of experience now.
Ryan: I’ll tell you one that I really liked for American Apparel because I think if you ask someone what an American Apparel advertising campaign was or, you know, you ask them to choose one, they’d probably pick one of like a young model, a really attractive model who is not wearing very many clothes and they might say like, “Oh, that’s easy to do because like sex sells.” Probably the single most effective earned PR campaign that American Apparel ever did was one of the creative directors. She lived in Manhattan, her name is Marsha Brady. She was walking down the street and she saw this older woman who was just… I think the where she is she said she was regal. She was just like a beautifully dressed like this older woman with this incredible amount of poise and the creative director just walked up to her and she said, you know, “I work for American Apparel. I’d love to use you as a model. Can I take some photos with you?” And of course, this model knew who American Apparel was and she just laughed, right? She thought it was hilarious, like you’re not gonna use a woman in her 60s as an American Apparel model. You’ve got to be kidding me. But they ended up collaborating, she took a bunch of photos and the creative director, she showed me these and she said, you know, “Obviously, we can’t use these, but I think they’re cool.”
And I said, “Why can’t we use them? What if we brand… Like, you know, we’re not gonna put this on the the back cover of Vogue, but what if we just ran them online and what if we picked just a few small websites that we could run them on, like really fashion-centric websites and then hopefully, media would pick up on the ad campaign and it would get a lot of attention? It could be more of a statement than a sort of a real ad campaign.” So we bought $1,000 worth of advertising on a site called Advanced Style that we found and this site is actually… It still exists, but the site is it’s a fashion blog of older people like really coolly dressed elderly people. It’s like this great idea. So we run the ad there, I take a screenshot of the ad and I send it…I think I sent it to a reporter at fashionista.com, which is a news site that covers the fashion industry, and from that, so one set of photos, $1,000 ad buy and a screenshot, this ad campaign ends up being seen by millions and millions of people. The model is, I believe, on “Good Morning America,” she’s all over every news channel. She becomes like a legitimate celebrity, she’s been used by other brands now. Millions of online impressions. It’s like one of the iconic American Apparel advertising campaigns and it all comes from, you know, a chance encounter on the street, a small ad buy and then sort of knowing what is gonna be newsworthy and generate attention.
Nathan: So where do most people go wrong when they try to generate PR? A lot of people work with agencies, I personally never have. In fact, I’ve never had much luck with PR, like mainstream never really done much. It’s often orchestrated bias. Like where do most people go wrong?
Ryan: I think one, they go wrong, they think that someone could just magically do this for them. So they hire someone, they spend a lot of money like sometimes $10,000 or $15,000 a month for 6 months or a year and they get nothing and it’s because they really, other than money, they put nothing in. But I think that the main reason that most people don’t get PR is because they’re boring and if you think about it, it’s like it’s not as if reporters are sitting around going, “There’s so much interesting stuff to talk about, I can’t squeeze it all in.”In fact, most reporters are bored, dying for really interesting news. They’re dying to talk about and break stories and talk about trends and fascinating events. So if you can do that, if you can make news with your company, with what you do, you’ll get a lot of attention and you’ll get it for free.
You know, American Apparel got to a point where we had more attention than we even wanted because of ad campaigns like the one I was just telling you about. Sometimes we would put an image on our website and then a reporter would write about it and they’d say, “American Apparel’s new ad campaign is controversial for the following reasons,” and it’s like, “No, no, that’s just like a random photo on our website. That’s not an ad campaign.” So we actually created this monster that was almost bigger than we wanted or needed it to be, but that’s what… When you are provocative and you don’t necessarily play by the rules and you’re willing to take risks, you can have the opposite problem which is too much publicity. It’s when you’re conservative and boring that, you know, you get nothing.
Nathan: So I’ve got a question. I’m gonna ask the PR master an idea, and I don’t know where this is gonna go, just for a project that we’re working on and I’d love to hear insights and I’m sure the audience would love to hear as well. So one thing that we’re working on is a coffee table style book, self-published, beautiful imagery, and it’s just gonna be just a collection of the best of the best interviews that we’ve done from all the front covers of the magazine. So like interviews with like Richard Branson, Ariane Huffington, many like, you know, iconic kind of well-known, very, very influential entrepreneurs in the startup or, you know, online space. We’re gonna do a Kickstarter campaign and I haven’t worked out the logistics yet around costing and all those kinds of things, but we wanna go out with a bang. Where would you start with the thought process or from a strategic standpoint where we could generate a ton of press for this physical coffee table style book?
Ryan: It’s a good question. I don’t necessarily know if this lends itself…from how I’m hearing it, if this lends itself to getting a ton of press. I’ll give you a couple of reasons. One, you know, if this was 2011 and Kickstarter was this sort of new platform, in some ways, anything that anyone did on Kickstarter was newsworthy. That’s not the case. If it was the first book on Kickstarter, it might get a lot of attention. If it was a book about something that doesn’t happen very often like you were doing a coffee table book of female founders or you were doing a coffee table book of, you know, Asian American founders or different…you know, something different, I think that might lend itself more to some media angles. When I’m hearing it now, I’m hearing it’s a coffee table book about entrepreneurship of interviews of well-known people but they’re all from your site. And so what makes this hard is that it’s not sort of extreme in any one category that would necessarily lend itself well to the media going, “I have to cover that right now.”
Now, does that mean that you can’t drive a ton of attention to it? Of course not. I’m just wondering if press is the best way to do it. For instance, let’s say every one of the founders who you interview tweets about this project or let’s say you are donating the proceeds to charity and the charity is driving attention to it or you do some sort of affiliate deal or… There’s a number of things I think you can do that can drive a ton of attention to the actual Kickstarter page and therefore drive a lot of contributions, but I would wonder like what do you think is exciting about this that is worth the media covering it and maybe we can dig into that?
Nathan: Yeah, that’s the part to give me a cool fun project for us.
Ryan: I did too.
Nathan: Yeah, and I know that it’s more…more than anything, it’s just a craft like, you know, our magazine is digital, all of our content is digital, we’ve never done anything print physical. I know the design will be amazing, I know we’d be able to fund it because we have quite a big platform and quite a sizable audience, but yeah, like I always see these Kickstarters, man, and it seems like, you know, everyone says it’s all about the press and I was just wondering how would we position it or how could we make it like strike some controversy? Like I know that… I thought it was brilliant what you guys did with Tim Ferriss’ book, how… I can’t remember which one it was. I think it was maybe “The 4-Hour Body” where you guys put it on…like you put it on the torrent site. Was that the one?
Ryan: Yeah, that was “4-Hour Chef.” Yeah, we put it on BitTorrent.
Nathan: Yeah, yeah. So it’s like do we need to come up with something crazy like that like or… Like I don’t know, man, but yeah, you’re right. I know what you’re saying. Like it isn’t that exciting, it isn’t that interesting. It would be cool body of work, I think, and, you know, I think we would be able to fund it from the size of that platform, but I don’t know if it’s that exciting to media outlets. I mean…
Ryan: The funny thing about the Tim Ferriss BitTorrent thing is he did get some media attention from it, but BitTorrent was where all the traffic came from. Do you know what I mean? So sometimes I think people are confused like, I mean, you just hear people saying like it’s all about the press for Kickstarter or whatever. It kind of is, but really it’s about how much traffic you can drive to something. Yeah, the media is more about social proof often times and less it’s like some incredibly viral, you know, imagery or ads. I don’t think like this is like boring and there’s no opportunities, I just try to think, okay, what’s… I try to put myself in the shoes of a reporter who gets pitched all day and I try to go, what would get them excited here? What would get me excited if I were them? And I think you’re close, you’re just not totally there yet.
Nathan: Okay. Interesting. Well, let’s switch gears and let’s talk about your latest book, “Ego Is the Enemy.” I think it’s an interesting concept because I find myself the more and more our company grows, unfortunately, sometimes, you know, when you get e-mails or every single day when people tell you how great you are and what you doing is so awesome and you crushing it, how can you not like, you know, it’s very… You have to fend off drinking your own Kool-Aid, man.
Ryan: Totally. Yeah, there’s this show, “Billions,” in the U.S. and I love this line, I quote it all the time. He’s like this hedge fund manager and he makes this really bad trade even though everyone was telling him that he shouldn’t do it and he’s talking to the therapist and she asked him why and then he says, “You know, when people tell you you’re Superman long enough, you start to think you can fly.” And I think that’s one of the dangers of being successful, is that all of a sudden the people who are in your life change, right? A good portion of the people that you or I might interact with are people that work for us, right, or people that want something from you and that changes the kind of information that you get, that changes the way people interact with you, and it can make you almost live kind of in a fake reality and it’s really important that you resist that. So what I’m talking about is how one sort of counter acts that impulse to start to think that you’re better than other people, that you’re special, that the world revolves around you because although it might be natural to feel that way, the reality is we don’t do good work when we were sort of high on ourselves. When we think that we’re amazing, that’s precisely when we’ll start working on something and stop listening to other people and make something that isn’t as good as it could be or that people don’t actually want or that has some sort of fatal flaw that we could’ve improved or fixed or caught in time but we didn’t because our ears were closed.
Nathan: So how did the basis of this book come about? Because, man, like you’re producing a lot of content these days. It seems like only not that long ago you created “Obstacle Is the Way.” So yeah, tell us about how this concept came about.
Ryan: Yeah, it was about two years between the books. I sort of, for the reasons you’re just talking about, I like to have my next book in the works sort of before I finish the one that I’m working on because I don’t want… If it fails, I don’t wanna be discouraged and if it succeeds wildly, I don’t wanna be distracted. I wanna have like my next thing. And I had plenty of time to work on this book. Again, I had a little over two years, but the idea was sort of what you’re talking about, which is as you become successful, as you pursue, you know, achievements and success, you can feel this ego inside you, this sort of arrogance coming up and I wanted to write a book that instead of encouraging that, the way that I think so many TED talks and articles and videos are out there sort of like, “Rah-rah, like you’re amazing, you’re worth it, go do this, like you’re the best, you know, take it,” all that sort of stuff, I wanted to write a book that sort of encourages people to maybe take a step back and to think and to question and to practice humility because I think really great, truthful, honest work comes from a place of vulnerability and humility, not arrogance and certainty.
Nathan: So, you know, what’s… You know, you’ve achieved so much at the age of 29, what do you do to keep yourself in check? How do you tame your ego? Can you ever conquer it? Is that possible?
Ryan: I don’t know if egolessness is like accomplishable. I don’t even know if that’s like necessarily, you know, what I’m shooting for, but what I think I am trying to do is make sure that whatever I’ve done doesn’t go to my head because you don’t know. Like you don’t know if the success that you’re achieving right now is the most success you’re ever gonna have or if it’s just a taste of what’s to come, right? So there’s really no reason to change because you don’t know. There’s this quote from Marcus Aurelius that I like. He says, you know, “You have to learn to accept it without arrogance and let it go with indifference.” And what I think he means is like the good stuff, you have to accept and celebrate without ever thinking that it makes you better than other people and then when that changes or it shifts, like if all of a sudden your company stops doing as well or, you know, there’s some financial crisis or there’s a problem, that you sort of…that washes right off you back too.
So that’s how I try to think about it and I guess one of the ways that I do it is by studying philosophy, you know, reading from great men and women from history who have accomplished far more than I’m ever going to and I like to learn from the lessons that they’ve sort of said to themselves. You know, they’re reminders to, “Hey, like, you know, you have to treat people well,” and, “Hey, you know, you don’t know how long this is gonna last,” and, “Hey, like, you gotta move on and focus on the next project now.” I like those little reminders, those have been very helpful to me.
Nathan: And what other practical pieces of advice would you have to people that are starting to see some success and it might be going to their head, but they don’t even know it? And I think that’s the most dangerous thing. It’s like a fog, right? Like you might be there but you don’t even know.
Ryan: Yeah, you don’t even know because the ego makes you think like you’re making all the right decisions. So I think one of the things you do is you have to be able to stop and pause and examine your own behavior, right? If you’re just reacting, reacting, reacting all the time, right? Like you get a nasty email, you’re like, “Boom, how am I gonna respond?” Right? Or like, you know, an employee isn’t working well, you’re like, “Boom, I gotta fire him.” Or, you know, some opportunity comes by, you’re like, “Boom, I gotta decide right now what am I gonna do.” If you’re sort of reacting all the time, you’re not able to ever go, “You know what? Is that the right thing to do here? Is this what I wanna do?” So one of the things I try to incorporate into my life is just like a bit more reflection and just like not just sleeping on decisions, but like, “Hey, I’m gonna take the weekend and think about this.”
And I remember I was feeling rushed about some decision recently, it was like an investment, and I was talking about it with one of my business partners and the guy that was trying to get us to invest was like, “You’ve got to decide by like end of today,” and he had just come to us with this. He said, “You’ve got to decide by the end of today or not.” And I went to my partner, I was like, “We have to choose or we’re gonna miss out on this.” You know, and he basically said like, “If they’re rushing you and they say you only have a day to decide, that’s a good reason not to do it. That means it’s probably not a good opportunity. Like good opportunities aren’t rushed like that and they aren’t urgent like this person is making them out to be. And like don’t let the fear of missing out or that you might seem like an idiot for passing on something that turned out to be good.” He was saying like, “Don’t let that make you make a mistake or rush when you don’t actually need to be.” And I’m really glad that I didn’t say say because something better came along like a couple of days later that didn’t require me to make a split second decision.
Nathan: I see. So from what I’m hearing, a big part of taming that ego because when you’re, you know, making decisions from an…like an ego-driven decision, that’s when you tend to make mistakes. So one of the ways to, I guess, stay more grounded is to spend more time on reflection and thinking about things and that’s something that I think is definitely underrated. Everyone is only looking at the hustle, everyone is all about getting things done as fast as possible. But I think it’s really important just to reflect and take time to think about decisions often.
Ryan: Yeah, I remember with my first book, I felt like if, and I remember even telling the publisher about this and I feel so embarrassed now, I was like, if this doesn’t come out like right now, it’s like not even worth doing. I was like this is so on trend and this is…I’ve so nailed this. You know, this is me in my egotistical like. Like this has to come out and if it doesn’t like, what are we even doing here? You know, and they were like… You know, they probably just like… They were probably just like laughing at me when I wasn’t there. And it ended up coming out and it took like I think nine months from like when I finished the book to when it was released which felt like an eternity, but it is actually really fast in publishing time.
But anyways, you know, the book is still selling and it’s been out for like four years and so I feel like such an idiot and there’s so many problems in the book that I wish I could fix. So I was totally wrong. Like I felt like…because this book was important to me, I felt like it was the center of the universe and that if I didn’t hurry like everyone was gonna move on, but in reality, like no one was paying attention and nobody cared and if I’d taken my time, it would have been a better book and if I’d been less self-absorbed and if I’d been less sort of bullish, I could’ve listened to the people around me that were trying to tell me exactly what is now incredibly obvious to me four years later, which is like, you don’t rush things, you take your time, it’s always better.
Nathan: Yeah, I think one thing that I found helps with decision making often is if it’s a decent size decision, I don’t… I know like execution is fast, you have to be always following your gut and, you know, trust that and you wanna be on the move fast. At the same time, I think it’s always good to bounce ideas around with other people to get, you know, a different perspective and that helps as well because I think if the ego is involved and always at play, you don’t need to ask anyone their opinion because you already know the answer.
Ryan: Yes, you know.
Ryan: Totally, although one thing I found is that like sometimes like let’s say there’s some conflict going on, right? Like if you’re negotiating with someone or someone like a client is upset or if someone’s sort of misbehaving or whatever, I found that if you’re in this sort of ego state, you’re like you’re pouncing on it, and you’re trying to get other people involved, and you’re calling, and you’re gossiping, and you’re thinking, and you’re practicing what you’re gonna say, and you’re all addled up about it. Whereas, like if you’re not in an ego state, you’re like, all right, I don’t like this. I’m gonna put it aside for a minute, I’m gonna go back to what’s important, and then I’m gonna come back to this when I’m calmer and I can see it more clearly. So I think you’re totally right. So you always wanna be getting other opinions and you wanna be judging things calmly and openly, but you also wanna make sure that you’re not just riling yourself and other people up because like this thing that fell in your lap is the most exciting thing to you right in that moment. At least that’s something I’ve had to work on personally.
Nathan: Yeah, I know. I think that’s something I personally got much better at because I’m very reactive still but…
Nathan: So also before we move on, we have to work towards wrapping up, but I was going to say, when it comes to the book, you’ve drawn on lots of very famous, you know, olden day super successful people. One thing that you said you found is a lot of these people they had to conquer their ego.
Ryan: Yeah, yeah. I’ll give you an example. So I talked about George Marshall who is a World War II General and then the Secretary of State and the Secretary of Defense for the United States. He won the Nobel Peace Prize, the Marshall Plan in Europe was named after him, he’s named ambassador China as well. Someone was talking to his wife and they were talking about how like that he basically had no ego. They said like, you know, “Your husband he has no ego, he’s so much better than everyone else.” They were basically making him out to be this sort of god-like figure who didn’t have any of the urges that the rest of us humans do. And she was saying like, “No, that’s not true at all. He had an ego, he had flaws. He just worked to overcome them harder than other people.”
And I think that’s… I like that because it’s saying that like, you know, these other people aren’t superman, they’ve just made it a priority because they understand that hey, when I’m running around like an egotistical jerk, I’m not as good as I could be. Like Kanye West is like this brilliant amazing musician, but like how much better would he be and how much further could his career have gone if he wasn’t getting into these like pointless battles all the time and he wasn’t pissing people off all the time who could be his fans?
Nathan: But do you think that that… Like I’ve always wondered with Kanye, is that like a PR stunt? Like where he gets on Twitter and he asks, you know, Mark Zuckerberg for a billion dollars in investment or… Is that just PR to keep himself relevant?
Ryan: Well, I think to a certain degree it has the effect of PR. It can sometimes make someone controversial and provocative and raise their brand. Like Donald Trump, clearly, is more famous as a result of his inability to like not open his mouth. But I find that having worked for people like that in the past, I tend to find that it’s… Like I would watch stuff happen at American Apparel and then people go like, oh, what a brilliant PR move. Like, you guys did it again. And it was like actually a complete accident or like I was begging them not to do that because it would have been a huge mistake and they like did it anyway because they thought I was wrong. Do you know what I mean? So you tend to find that controversial people, they have a knack for getting attention, but also like they can’t turn it off and they often cause a lot of problems for themselves even when they’re not meaning to.
Nathan: Yeah. Okay, that’s interesting. So you think it’s not so much strategy for Kanye, just is who he is.
Ryan: I think some of it is clearly strategy, but I think, you know, when he gets up there and he interrupts Taylor Swift on stage the first time, I think that’s not… He didn’t know how that was gonna go.It was like he just didn’t think. And he can’t not… He’s like I have an opinion, you have to know my opinion. Whereas like someone who is just doing a marketing stunt probably wouldn’t have, you know, attacked America’s sweetheart and expected it to go well.
Nathan: Got it. Well, look, we have to work towards wrapping up. I could talk to you all day, man, but I think one thing that people would really find interesting is one thing I noticed that we get a lot is, you know, constantly a lot of people, write to people in our team and Foundr in general is people wanna know like how do you find a mentor? And you’ve done very… You know, you’ve got incredible swathe of mentors or, you know, unquote unquote, I doubt you even call them mentors, but people you can draw upon whenever you need, you know, help or if you’re stuck on a decision or need to bounce an idea around. I’m just curious, you know, what advice do you give around that pace because yeah, you’ve got an incredible network of people that we can always learn from?
Ryan: Well, thank you and I feel very grateful to have been sort of top of the people who taught me. I will say like most of those relationships are not official in the way that I think people who want a mentor think that they are, right? Like in no cases have I ever gone up to someone and said like, “Will you be my mentor?” Right?
Nathan: Yeah, it’s just a thing, you know.
Ryan: Yeah, and I don’t think they ever said that… I don’t even know if they would have identified as a mentor. It’s just that I learned a lot from them. Like, look, some of the people that have mentored me, they’ve never even met me or some of them are dead, right, and I just learned from their books. So it’s not so much an official thing although there is this quote from Sheryl Sandberg and I’ve used in a couple of articles. Basically, she’s saying that people think it’s like if you wanna do well, you should find a mentor when it’s actually if you do well, mentors will find you. It’s when you start to be showing momentum and progress that successful people seek you out and they want you to work for them or they want to ask you a question or they wanna point you in the right direction because they see something in you. So you wanna make sure that you don’t think that it’s this like altruistic exchange. In reality, it’s like if you have your act together and you show potential and you’re a hard worker who is going places, finding mentors is not gonna be a problem. It’s gonna be like deciding which one and which opportunities to take is the hard part.
So like when I get e-mails from people and they’re like, “Oh, can you be my mentor,” it’s like, “I’m sorry that’s not how it works and I wish that I could, but I can’t.” Or even other times people go like, “I don’t want anything from you, I just want to work for you and I’ll work for you for free.” That’s very nice, but what I wish they would understand is like I don’t just like have a bunch of tasks sitting around that I’m not doing because no one has offered to do them for free for me. You know what I mean? And I think you’re probably the same way. You don’t just like have a bucket of like unpleasant things that you’re just like hoping someone will take care of. It’s like if someone came to you and they said,” Hey, Nathan. Like I’m really good at SEO and I noticed that like your site is not doing these things right or you haven’t tried these things, I’d like to offer to help you do them,” you might be like, “Sure, I’ll give you a chance.” Or if someone’s like, “Hey, you know, I’m an expert about this,” or, “Hey, I have this crazy idea.” That’s how I started working for Tucker Max, is that I had this idea for something that he could do on his site advertising wise and he said, “Sure, give it a shot. Like I don’t care.” It was all upside for him. What I didn’t say is like, “Will you hold my hand and teach me everything?” You know, it doesn’t work like that.
Nathan: Yeah, I think that’s so true. And I think, you know, just on that intern piece, so I wanna work for free, like it actually…it’s more of a cost in time than anything that people don’t want to spend time. They would rather happily spend money. If you want to hire someone, you just hire them and you’d rather hire someone experienced and just pay them as opposed to just someone working for free to do stuff that you have to teach.
Ryan: Yeah, it’s like if I could pay someone and they’re gonna do it once and it’s gonna be good, I’d rather do that than have to teach you how to do it and then you do it for free. So it’s like if I am gonna teach you, I want to know that you’re…it’s that I think you’re going places and that this is the best thing for you to start with. So that’s why it’s so important that you go out there and you make something or you create something or you have a resume that shows like, “Hey, I’m not just some random guy waiting for my chance. I’ve gone out there and I’ve done it and now I’m looking to take it to the next level.”
Nathan: Yeah. I know, that’s where it’s at, that’s where it’s at. All right, look, I have two more questions for you, Ryan. One, where do you see your career as a marketer, an entrepreneur, a writer/author going? I’m sure you feel you’re just scratching the surface and then lastly, where is the best place people can find you and, you know, find out more about “Ego Is the Enemy,” your latest book?
Ryan: Thank you. Yeah, I think for me, I’ve tried to… One of the dangerous things, and this is related to ego, is that as you become successful, you’ve just accomplished the thing you set out to do. Instead of like appreciating that, you’re like, “What’s the next thing? I gotta beat this all the time,” and that’s like exhausting. So I really like writing, so I wanna do that. Like I wanna do more of this and so I see my career as having been really fast at the beginning and now I’m going into a period where I really have to put in a lot of time and energy to improve and grow and that it’s not gonna be as fast from here but I’m settling in for the long haul. So that’s how I see my career as a writer and a marketer and I think I’m really happy about that. It took a lot of some soul searching and some thinking to get there, but I’m excited about that. And then if anyone, you know, likes my books, they can find them all on Amazon or wherever books are sold and my website is ryanholiday.net and I think I’m @ryanholiday on pretty much every platform.
Nathan: Awesome. All right. Well, look, thank you so much for your time, man. It’s been an awesome conversation, glad we could finally connect.
Nathan: We can wrap there.
Ryan: Thanks, man. Thank you for having me, I really appreciate it. You guys do amazing stuff.