Ryan Holiday is a media strategist for notorious clients like Tucker Max and Dov Charney. He is the Director of Marketing at American Apparel, where his work in advertising is internationally known. His strategies are used as case studies by Twitter, YouTube and Google and have been written about in AdAge, the New York Times, Gawker, and Fast Company. His book, Trust Me, I’m Lying: Confessions of a Media Manipulator was a Wall Street Journal Bestseller.
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Resource Mentioned:
- Your Big Idea: Successful Entrepreneurs have One Big Idea. Follow JLD’s FREE training & you’ll discover Your Big Idea in less than an hour!
Success Quote
- “The way to success is strategically along the way of least expectation and tactically along the line of least resistance.” – William Tecumseh Sherman.
Business Failure
- Ryan fails every day, and he shares his outlook on the term failure with us. It’s quite an insight.
Entrepreneurial AHA Moment
- Ryan believes it’s the everyday small AHA moments that lead you to greatness. He shares some of his along the way and how he uses those moments to turn brilliance into gold.
Current Business
- Ryan is all about thinking outside of the box. Some of his ideas have truly been revolutionary and are now mimicked across the globe.
Small Business Resources
- Blogs
Best Business Book
- Mastery by Robert Greene
- The Meditations Of Marcus Aurelius by Marcus Aurelius
- Trust Me I’m Lying by Ryan Holiday
Interview Links
Killer Resources!
1) The Common Path to Uncommon Success: JLD’s 1st traditionally published book! Over 3000 interviews with the world’s most successful Entrepreneurs compiled into a 17-step roadmap to financial freedom and fulfillment!
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3) Podcasters’ Paradise: The #1 podcasting community in the world!
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Full Transcript
John Lee Dumas: Hire Fire Nation and thank you for joining me for another episode of EntrepreneurOnFire.com, your daily dose of inspiration. If you enjoy this free podcast, please show your support by leaving a rating and review here at iTunes. I will make sure to give you a shout out on an upcoming showing to thank you!
John Lee Dumas: Okay. Let’s get started. I am simply inspired to introduce my guest today, Ryan Holiday. Ryan, are you prepared to ignite?
Ryan Holiday: I am.
John Lee Dumas: My man! Ryan is a media strategist for notorious clients like Tucker Max and Dov Charney. He’s the Director of Marketing at American Apparel where his work in advertising is internationally known. His strategies are used as case studies by Twitter, YouTube and Google and have been written about in AdAge, in New York Times, Gawker and Fast Company. His first book, “Trust Me, I’m Lying: Confessions of a Media Manipulator” was a Wall Street Journal best seller.
Ryan, I’ve given Fire Nation a little overview of your business and what you do. Why don’t you give us a little more in-depth about who you are?
Ryan Holiday: Yes. So what I do I guess in short is I help clients get the attention they feel like they deserve in what is increasingly a chaotic and sort of bitter fight on the Internet. I mean like there’s a million people trying to be heard over a million other people, and how do I and my clients make sure that their messages are the ones that get through, and that’s what I’ve come to specialize in.
John Lee Dumas: Well, you really do dive into that in your book Trust Me, I’m Lying, which I read and I definitely truly enjoyed, and I look forward to delving into that later in the show.
Ryan Holiday: Okay.
John Lee Dumas: Let’s start off right now with a success quote. We always start the show at EntrepreneurOnFire with a success quote to get the motivational ball rolling to get our listeners really fired up and pumped up for the rest of your content. So what do you have for us today?
Ryan Holiday: Yes. So one of my favorite books is a biography of William Tecumseh Sherman by B.H. Liddell Hart, who was sort of an early 20th century military historian. So he has this quote – I’m sort of paraphrasing it – but he says that sort of “the deep truth of strategy is that the way to success is strategically along the line of least expectation, and tactically along the line of least resistance.” I think that has always underpinned how I think about marketing and think about strategy and think about everything that I do, which is how do you find the thing that no one is expecting, and because they’re not expecting it, you have the resources and the skills to pull it off. When you combine those two things, you get explosive results.
John Lee Dumas: Explosive results. That’s a great thing. Being an American Studies major back in the day during college, I’m pretty confident that William Sherman was a Union general who really was attributed with potentially ending the war by ravaging the south. Is that correct?
Ryan Holiday: Yes, yes. So basically, Sherman and Grant were sort of these – it’s actually sort of a fascinating friendship, but basically, Grant and Lee were sort of locked in battle in the northern front, in Northern Virginia particularly. Then Sherman came from the west and sort of went behind the southern lines and cut themselves in half.
He understood that what was powering the south was its people’s passion for the war, and he took the war to the people and he ripped the guts out of the Confederacy so it didn’t have to end in some sort of epic battle between Grant and Lee. It was much more a matter of ripping out its will to fight. Like obviously that’s a pretty gruesome metaphor, but I think his approach, which was to understand the real center of gravity of the war, and to attack all these energy and resources there was what ended the war substantially earlier than it would have gone on otherwise.
John Lee Dumas: Yes. Absolutely. Being an army officer specifically for eight years myself, I can definitely see the strategic importance of doing that, and I could definitely talk about this aspect of just your quote all day. It’s just I have another passion for American history specifically, and being from Maine, we do have a rich tradition with Joshua Chamberlain who was the general of the Little Round Top who was attributed with the turning point in the Battle of Gettysburg. So we really have a lot of pride up here for that reason and for that individual specifically.
Let’s move on from that because again, I can get carried away, but I really enjoyed that little side note, and I hope our listeners did too. Let’s just kind of get into real quickly, how do you specifically use that quote to your everyday life, or just to your mentality in business?
Ryan Holiday: So I’ve always represented clients that are a bit more controversial than your average clients. So I don’t represent like yoga studios or charities. I tend to represent very controversial, often polarizing authors. So for us, we’ve always said, Okay, look. Here’s where everyone else is competing for attention. Everyone is trying to get their book reviewed in The New York Times. Everyone is trying to get on CNN. Everyone is sort of trying to go this traditional route of publicity, which is you sort of wine and dine and you schmooze the reporters or journalists that you want to write about you.
Then we said, Look, that’s what everyone’s expecting us to do. And if we do that, they’re going to reject us because we don’t fit in their typical box. So how can we make our own news that is not only cheaper and easier to do, but gets us attention in a way that otherwise we wouldn’t be able to?
So with my clients, I say, “Look, we want to be in The New York Times. How can we do something that’s so interesting and so sort of counterintuitive and crazy that The New York Times comes to us and says, ‘We’d like to do a story about you?’” That’s fundamentally different than submitting your book for review, waiting for months, hoping they write about you, and then ultimately that review having very little impact on sales. So for my clients, we’ve always been very aggressive and very untraditional in terms of the lengths and the ideas that we’re willing to implement, if that makes sense.
John Lee Dumas: Well, it makes total sense, and the way that you implement it, it actually puts you in charge in a way because you’re able to dictate, because as you said, they’re coming to you. You’re not waiting around for them to maybe publish it on a day that you might not even be ready for months and months down the road. They’re coming to you, you’re setting the ground lines, and you’re going forth from there. So that’s a very nontraditional, but effective way to go about it.
Ryan Holiday: Right. When you’re going along the line of expectation, you’re having to outfight or out warrant attention from people who are bigger and frankly more interesting than you. Like The New York Times has hundreds of books sitting there waiting for articles, right? To me, that’s just not a fight I’m likely to win. As good as I think my books are and my clients’ books are, that’s a tough fight to win. But if I can do something interesting and if I can engage in sort of publicity stunt, if I can attack some sacred cow, or if I can do something that’s truly newsworthy, I get to go to the front of the line, and I like going to the front of the line because I hate waiting.
John Lee Dumas: Absolutely. Thanks for that inside look. That is just great. Ryan, we’re going to use that to transition to our next topic because at EntrepreneurOnFire, we really like to go back in your journey as an entrepreneur. Your story of what you’ve done in your past to get to where you currently are today.
For every entrepreneur, at some point in your journey, you encountered failure or you’ve encountered an obstacle or a challenge of some sort that you’ve had to overcome. Obviously, there are small ones every single day that we face, but can you look back into your journey and pull out a very telling failure or obstacle that you came across and how you reacted to that?
Ryan Holiday: Yes. If I look at my path, I see it as sort of one of continual failure in that I’m sort of completely self-taught. I dropped out of college. I have no formal training in any of the things that I do, but I had really good mentors who were able to sort of walk me through this process. I think that one of the best ways to learn from mentors – and this is what I do when I’m sort of trying to return the favor – which is you throw someone into the deep end of the pool. You let them make mistakes, and then you sort of slowly correct them from there.
So I can’t think of one like catastrophic failure off the top of my head, but for me, it was, Okay, Ryan, I need you to help market this book for me, and I have absolutely no idea how to do that. Then sort of teaching myself from scratch how to do these things is how I learned and how I got to where I am now.
It’s interesting that you bring that up because like I think all of us know in our heads that we learn from failure, but we spend so much of our time and energy trying to prevent failure from happening, and we try to do everything perfect and we try to take on things that we know about or that are in our comfort zone.
For me, what I did was – and I think I was only able to do this because I was sort of a brash teenager honestly when I started – which is just take on things that I was just objectively not qualified to deal with, and if I could just eke out a tiny bit of success, for me I’m coming out ahead.
So I got to where I am, I guess in short, by taking on projects that were way above my level, and just struggling like hell to not let anyone down. When you do that, you end up learning so quickly and taking on more than you can handle, and I strongly recommend that for people.
John Lee Dumas: So not being afraid of failing, and a failure in and of itself, was a major lesson that you learned from diving in into the deep end and really having to self-teach yourself certain skills that people thought or assumed that you already had. So that’s a great lesson that you pulled out of that. Can you get specific and pull out one more lesson that you really learned from these challenges that you’ve faced in your past?
Ryan Holiday: Yes. So when you learn by trial and error, obviously you’re learning hundreds of lessons. For me, it was this sort of gradual awakening. I feel like if I’d been trained and if I had gotten a degree in marketing or business, and then I worked for a PR agency and then I sort of slowly developed my own clients, what I would’ve learned is the old way of doing things. That would have made it a lot harder for me to see this new way of doing things because you get very whetted to the way that you learned.
So for me, having almost complete freedom to do these things however I thought it made the most sense for them to be done. Look, obviously my instincts were wrong all the time and I would touch a stove and get burned and not touch that stove anymore, but I sort of was able to see the media system very clearly for what it was without any allusions or without any of the edifice or artificial sort of structure that PR people put on it.
So I sort of saw it as this chaotic, wild west where everyone was out trying to make a name for themselves, and I figured out how to do that better than a lot of people or how to use that to my advantage. So I think what I learned what really like see things for what they are and don’t come into a new field with all these baggage because I think if anything, we’re starting to learn that so many of the dominant industries that we’ve taken for granted are really showing their age. They’re starting to fall apart and they’re starting to show major flaws.
If you go in them from a traditional path, you carry a lot of those assumptions with you and it’s harder to throw away a bad assumption than it is to pick up a new good one. So for me, my untraditional path was very freeing in that I got to take only the good stuff and I didn’t have to pick up any of the bad habits.
John Lee Dumas: Now this is just a perfect segue into our next topic, which is the aha moment. How you lead your life and how you face every day, it just means that you are having these little aha moments every day. You’re just realizing things. These little light bulbs are going off in your head and you’re seeing things for what they are – the reality of them – and that’s so important as an entrepreneur. Can you go back, and at some point in your journey, did you have a major light bulb moment that just kind of shined above and brighter than all the little ones that you were experiencing consistently and continually?
Ryan Holiday: Well, I like what you’re saying about the little light bulb moments because I think those are better than the big ones. I can’t think of one big moment where sort of it all became clear. That I had this epiphany and that’s how I understood it. It’s much more. It’s like, look, if you’re going out and doing battle every day, if you’re stepping into the arena and you’re seeing how things work, then you’re gradually learning. You pick up a trick here and you pick up a trick there, and you pick up an understanding somewhere else. Then finally, gradually, you build this familiarity and sort of a deep intuitive understanding of what you do. That sort of accumulatively adds up to your big epiphany, or at least that’s how it worked for me.
So it was dealing with hundreds of bloggers, writing hundreds of press releases, doing hundreds of campaigns. So American Apparel, who’s one of my bigger clients where I’ve been the Director of Marketing for the last several years, it’s a company that doesn’t do like sort of big seasonal launches, but instead it rolls dozens of products a year, if not more. Not dozens probably. I’m underselling it. Hundreds of products.
So for American Apparel, instead of doing one or two big product launches where you see how it works, I was doing many, many of those, and each time I would get a little better at it. I would understand a little bit more I could learn from what I did last time. So it was like I was able to condense years of experience down into a much shorter period. Like let’s say you do movie PR. Even a good studio only puts out a few movies every year. So it’s going to take a long time for you to really get good at doing it because you just don’t have the opportunity to experience it in multiple iterations.
So I strongly recommend that people, even if it’s harder and you make less money and it’s more work, is take on a place where you get many, many at bats rather than like a few symbolic ones, because you learn every time you step up to the plate. You know what I mean?
John Lee Dumas: Absolutely. I would just love to share an aha moment that I had while reading your book that I would kind of like you to expound upon before our listeners that was just so powerful to me. That’s when you were operating as the Director of Marketing for American Apparel and you just had this epiphany that’s kind of an out of the box light bulb or a thought yourself of, “You know what? Nobody’s reaching out to these young, wildly popular with massive subscriber audiences bloggers about fashion. I want to be that person that’s reaching out with them, really connecting with them, and having them have a feel good vibe about American Apparel because we’ve earned it.” Can you speak to that?
Ryan Holiday: Yes. I think this goes back to what we were talking about earlier. If I had sort of started as an intern at a magazine, then I became the marketing director there. Then I moved over to the industry side, and then I was working for a brand. I would have had all these assumptions about how fashion PR is supposed to work, and I would’ve internalized this notion of gatekeepers, and that it’s magazines that drive the fashion cycle or it’s television or celebrities. But instead, I came to it from a world where blogs sort of drive the public conversation, and blogs are really easy and much more casual about their relationships than traditional media.
So I sort of saw these fashion blogs coming out of nowhere when this thing was first starting, and I said, “Well, let’s just talk to them. Why not?” Like there’s no question people in the company who would come the other way were resistant to this idea. It’s like who’s going to take fashion advice from some random girl in Connecticut who posted on a blog? And my feeling was lots of people. This is going to be the future of the industry. I was able to see it that way because, again, I didn’t have any preconceived notions about how it was supposed to work. I just knew an opportunity when I saw one.
So we started sending them stuff, we started working together, and it became so effective so quickly that all the other people in the company got really into it. But I was able to get that ball rolling because I could be more open-minded than they were. Then once the results were there, everyone sees that this is a good idea. But it’s when you’re able to – like you were saying – see things as they are, you can spot opportunities and take small, calculated risks, and that’s where new things come from.
John Lee Dumas: I just love when people can think outside the box, which you were able to do coming from “outside the industry,” and I really have to applaud American Apparel for really putting you in the position to implement that because that was really forward-thinking of them as well. So I really enjoyed both aspects of that.
My next question is kind of an interesting question. People definitely answer it in a different way every single time, which is why I like it. Have you had an I’ve made it moment yet?
Ryan Holiday: For me, having the book make the bestseller list was sort of like a weird moment where it’s like – I don’t know. It’s weird. So you sit down and you write a book, and that’s not a thing that most people do, but I feel like a lot of people write books. Then I’ve known a fair amount of people who have gotten book deals.
So it’s sort of like for me it was this funnel. Then by the time I got to the part where it was like a bestselling book, I really felt like I could give myself the credit to say like, “Hey, I’m an author.” Like I wrote a book. That was cool, but I’ve always tried to remind myself that like external validation is not proof that you’ve made it. It’s not what you should be shooting for. You should be trying to do good work that you appreciate and stand by and are proud of.
So to me, making it has sort of always been this weird sort of subjective benchmark that I’ve tried not too much stock into, but it’s nice to be recognized by your peers and have something to kind of hang your hat on, because I think for me, I actually felt like once I had done that, I could calm down a little bit. It’s like, okay, everything from here on out is just extra. That’s been a cool feeling for me.
John Lee Dumas: It’s kind of a catch 22 at the same time because you never as an entrepreneur want to fully rest on your laurels and just sit there and really take it all in while not just reaching out and setting your next goal even higher once you’ve attained that original goal.
So you always want to be pushing yourself further and further once you’ve reached that goal, but at the same time, it is important every now and then, once you have hit a benchmark, to take it all in and to appreciate it because that’s what all the hard work is for. So I definitely applaud you for doing that and I definitely see where you’re going in the future as far as where you want to keep pushing yourself higher.
Ryan Holiday: Yes, because at the end of the day, you don’t have much control over these things. And if you fool yourself into thinking you do, you’re going to be really disappointed when things are snatched from you.
So for me for the book, the goal was to hit The New York Times Bestseller List, and I objectively moved enough copies to hit that benchmark, but The New York Times is sort of very secretive and particular about how they decide who’s a bestseller or not.
John Lee Dumas: Right.
Ryan Holiday: And they took it away from me. Like I qualified and I think they didn’t approve of the kind of content that my book is, and I didn’t make it. So although that was my goal, deliberately knowing that this could happen, I didn’t want to make it feel like making the list or not making the list said anything about me as a person because I would’ve been crushed when I was unfairly deprived of something that was mine.
I like to think about it as like you have your goal, but it’s not a matter of life or death if you achieve it or not because at the end of the day, there’s so many things that are outside of your control that can take a goal from you, that can change the direction of your life, that can prevent things that seem like a sure thing from happening. I think the last thing you want to do is put so much on something, that when it doesn’t happen you’re devastated because life is too short to be devastated.
John Lee Dumas: So let’s talk about present day right now. In your current situation, what you’re doing. What is one thing that’s really exciting you right now?
Ryan Holiday: I don’t know. I’m starting to think about my second book. So for me, the research phase is the most fun part of writing a book. Writing can get sort of tedious. Editing is miserable. For me, it’s throwing together like the outline of an idea, and then going out there and trying to collect as much meat to throw in with those bones. That gets me really excited.
My next book is going to be about practical philosophy. Stoicism, most directly. So now I sort of get to go out and I’m getting paid to read books about things that get me excited. That’s gotten me up every morning. Some of the books I’m doing marketing for in the next few weeks have gotten me really excited. Robert Greene has an amazing book coming out about mastery, which I think is a really timely subject. The idea of becoming the best at something and sort of doing an apprenticeship, learning something, working at it for years being a journeyman, and then becoming a mastery. I think there are a couple of things like that that have gotten me excited. So that’s what I’ve been focusing on recently.
John Lee Dumas: We’ve all got to put in our 10,000 hours, that’s for sure.
Ryan Holiday: Yes. Exactly. Actually, what he’s saying in the book is the real research has shown that it actually takes 20,000 hours. 20,000 hours is how you get to the level of not just being really good at something and being the best, but remaking that thing and redefining it and changing the rules. It takes 10,000 hours to understand the rules better than anyone else and learn them, but it takes 20,000 hours to so internalize those rules that you rewrite them and you take whatever it is that you’re doing to the next level.
John Lee Dumas: Bummer! I just hit 3% for podcasting.
Ryan Holiday: Right.
John Lee Dumas: And now I’m down to 1.5% with this new information.
Ryan Holiday: Yes. Exactly. You get your 10,000 hours, and then you’re like, “Oh man, I’m halfway there.”
John Lee Dumas: [Laughs] So Ryan, obviously, no two days are the same for you. As an entrepreneur, you have a variety of tasks that demand your attention, but at the same time at EntrepreneurOnFire, we really kind of like to pull back the veil a little bit and show that we as entrepreneurs still have tasks that we need to complete each and every day that take up our time. What are two tasks that seem to occupy a portion of your day?
Ryan Holiday: Yes. Weirdly, the two tasks that I make sure that I do every day actually are sort of – in a way, they have nothing to do with what I do, but to me they have everything to do with what I do. So I do at least two hours of like hard, strenuous physical exercise. I do like Brazilian jujitsu in the morning, and then I normally run and swim in the afternoon.
To me, it’s having that sort of disciplined activity that I think strengthens me and allows me to apply that mindset to the rest of the things that I do. I think exercise is also important because it disconnects us from our cell phone, from the TV. It’s sort of we’re one with ourselves. To me, a lot of my best ideas come from having worked all of the first half of the day, and then I go for a run in the afternoon and my mind is just sort of relaxed and ideas come to me.
Then the other is I read a lot. I consider myself a voracious reader. I don’t schedule reading time every day, but whenever I have a free moment, I pick up a book. For me, again, having no real formal training, like I consider books to be my sort of alma mater, and I consider reading to be part of my job. Like no one says, “Hey, Ryan…” Like we’re paying you to market our book. Like we want to make sure you’re doing a lot of reading, but it’s in reading those books that I get most of my best ideas. So I consider those two things to probably be, if anything, the secrets to my success.
John Lee Dumas: So many people would look at what you said and they would say, “I don’t even have time to work out once a day. Let alone twice a day.” Well, the reality is is that they’re just having this massive space of time that is just increasing to the time that they’re allotting to it, whereas you have a very disciplined program where you’re working in the morning. You know that you’re focused during the day now to get all of what you need to get done done before your afternoon or evening workout.
So it’s a great approach to it. I really have to applaud that. I’m a big proponent of exercise myself. I’m really into the P90X Insanity trip right now, so I’m really excited about all that stuff.
Ryan Holiday: Yes. It’s funny. Like when I was working in an office, I never had time to work out, or I felt like I barely had enough time to squeeze in all the things that I did during the day. Then when I started working from home, I could make my own schedule and I wasn’t worried about appearances. I wasn’t worried about spending time in the office. It’s like, look, running is important to me. It helps with my work, and so does reading books. I’m going to do it when I feel like it.
Now, when I go back – because I still have an office. When I go back, it’s like how did I ever spend 8 or 10 hours here? Like there’s not enough to do. I want to go running right now, but I can’t because it’d be like why am I leaving in the middle of the day? It’s once you break the mold, it’s sort of you find out. Like you were saying, I think it’s Parkinson’s Law. How much you’re just slowing things down to fit the mold that you’d been told your workday has to fit in.
John Lee Dumas: Absolutely. Now, this next question I’m really excited for because I feel like you are truly cutting edge in what you do. So Ryan, what’s your vision for the future?
Ryan Holiday: Yes. So my book is sort of all about how the media system works right now and how I think it’s pretty broken and how people have to do these things that are scary and sort of at a gray area in terms of tactics. I see people needing to circumvent the media system and go directly to their audience.
So right now, you have to get an article in The New York Times to get people to hear about your product launch. That’s a bottleneck that controls everything that companies do. I really see the future being one where you have direct access to your customer, whether it’s through Twitter or Facebook or through email lists.
That’s why I focus my clients on doing this. Building those permission assets so you don’t need to court media attention and engage in publicity stunts and sway bloggers and create the news so you can be in the news, because when you have a new thing that you want to tell your customers about, you just tell them about it.
John Lee Dumas: I love that vision, and I cannot wait for it to come to fruition. So Ryan, we’ve now reached my favorite part of the show. We’re about to enter the Lightning Round. This is where I provide you with a series of questions and you just come back at us with amazing and mind-blowing answers. Does that sound like a plan?
Ryan Holiday: Yes. It sounds like a plan.
John Lee Dumas: Awesome! Take like 30 seconds for a nice direct answer to these, and let’s just really get our bang for the buck here.
Ryan Holiday: Okay.
John Lee Dumas: What was the number one thing that was holding you back from becoming an entrepreneur?
Ryan Holiday: It’s the fear of the unknown I think is what holds me back. It’s what holds people back. It’s how am I supposed to make money? What am I supposed to do during the day? How is it going to work out? The scary thing is that it seems like you are doing what you’re not supposed to do. It seems like you’re taking this massive risk.
In fact, you’re not only not taking a risk because in my experience, it’s more profitable and it’s more enjoyable, but when you get to a state where you don’t have to show up in an office every day, and you can do what you’re passionate about and you can do what you care about, you realize how much more aligned that is with human nature and the way we’re supposed to live our lives, that you end up almost accelerating. You work more and you work harder and you love what you’re doing more. Like you’re more creative. Ideas come to you.
So for me, it was this fear of what’s it like if it’s not like this? Sort of The 40-Hour Workweek. What’s it like if it’s not like this? It’s a funny fear because it turns out that life is so much better. It’s not only not something to be afraid of. It’s something you should look forward to.
John Lee Dumas: That has absolutely been a reality since I launched EntrepreneurOnFire. What is the best business advice you ever received?
Ryan Holiday: So Dov Charney who’s the CEO of American Apparel, he’s been a mentor for me. I remember one time, I was working on some project, and it ended up going really well. I sent it to him and I was like, “Hey, look. We made all this money. It went really well.”
Then he called me and he was like, “You know what? It’s great. I’m proud of you. You did good, but you’ve got to be a miserable Jew about what you’re working on.” I was like, “What do you mean?” He’s Jewish, but he’s saying, “You got to be a miserable Jew. You can’t look at what went right here. You’ve got to look at all of the things that could’ve been a little bit better. You got to be neurotic and obsessed and almost depressed about what you’re working on so you’re constantly refining and refreshing and changing and improving because you’re never satisfied with what you’re doing.”
To me, that was a fundamental flip because I think that especially people in my generation, you’re looking for what you did well. You’re looking at what went right and what you’re happy with. That’s great and it’s probably better for your personal sanity, but it doesn’t make you improve what you’re working on. It doesn’t make you hungry, and I think being hungry is the essence of entrepreneurship.
John Lee Dumas: What is something that’s working for you right now?
Ryan Holiday: Just sort of living my life on my own terms is working for me. It’s doing the things that I care about, working on the things that I like about, ignoring the things that I don’t. Setting my own pace.
John Lee Dumas: Ignoring the things that you don’t care about, that is so critical, and I definitely am glad you brought that point up. Do you have an Internet resource that you could recommend to the listeners that you are just in love with right now?
Ryan Holiday: I mean there are a couple of blogs that I like. I like reading blogs from people who aren’t blogging for a living. They just write about things that they care about. So for instance, like I love Mark Cuban’s blog because like Mark Cuban’s a billionaire. So when he sits down to write about something, it’s something that he cares about and he felt like needed to be written, and not like someone’s paying him to write about it.
There are a couple other good blogs like that where the person is sort of not dependent on the blog for their living, and they’re able to be so much more honest and authentic. I think that’s what blogging originally brought to the table. A lot of the negativity and criticism that I have in my book is for sort of The Huffington Post model of journalism where they’re trying to eke out these tiny profits over thousands of articles. I like people who are writing because they have something to say, and not because they’re trying to make advertising revenue.
John Lee Dumas: Absolutely. Now you’ve already mentioned Robert Greene and Mastery, and I’m definitely going to link up your book in the show notes as well. What would you say is the best business book besides those two that you’ve read in the last six months?
Ryan Holiday: Business book, or can it be any book?
John Lee Dumas: It can be any book.
Ryan Holiday: So my favorite book in – and this goes to one of the things that I’m going to be working on in my next one – my favorite book is the book that I never travel anywhere without that I’ve read probably a hundred times is The Meditations of Marcus Aurelius, which I think is sort of the greatest book ever written for self-improvement and discipline and humility and resilience and robustness, which are not just great for making you a better person, but I think they very much dovetail with the lessons that entrepreneurs and businesspeople need to learn.
John Lee Dumas: Very unique. I love that. So Ryan, this last question is my favorite, but it’s kind of a tricky one. So definitely take your time, digest it before you answer. This is the question. If you woke up tomorrow morning and you still had all of the experience, knowledge and money that you currently have right now, but your business had completely disappeared in every way, shape and form, leaving you essentially with a clean slate, which many of our listeners find themselves in right now, what would you do in the next seven days?
Ryan Holiday: I’m really excited about like the Amazon self-publishing platform. I think it’s never been easier for authors and writers and thinkers to develop an audience and to develop a sort of direct relationship with customers. I could very easily see myself, if I needed to make money tomorrow and I didn’t have any contacts, I didn’t have anything to start with, how could I use like sort of the principles of free, the principles of close to free, of self-publishing, of sort of being a ubiquitous presence and selling ideas, I think Amazon’s platform for self-publishing and for e-books is really for people in a fascinating, exciting place to do new and cool things.
John Lee Dumas: That is exciting. This whole interview has truly been exciting and inspiring. So honestly, thank you so much for joining us today. You’ve given us some great actionable advice, and we are definitely all better for it. Give Fire Nation one last piece of guidance, then give yourself a plug, and then we’ll say goodbye.
Ryan Holiday: Yes. It’s funny. One of the other best business advices I got was also from Dov, and I think it goes with the question you just asked because he was reminding me that the run rates always start at zero, and so often we’re thinking about how to make this huge thing, that we forget that we have to like start with nothing, and that you have to put in a lot of work before you can go from zero dollars in revenue to one dollar in revenue. But once you make that, it’s a lot easier to go from $1 to $100 to $1,000 to $10,000. So don’t be afraid to try and don’t be discouraged that you’re starting just at zero.
I think my book is a good way to take that thing that you started that you want to get in from of customers and you want to get attention for your work. My book is sort of a how to and it’s a blueprint for doing that in the Internet era.
John Lee Dumas: Wonderful! Well, that will all be linked up in the show notes. Ryan, thank you so much once again, and we’ll catch you on the flipside.
Ryan Holiday: Thanks for having me.
