Hack the System Podcast — How Ryan Holiday Hacked the Media at American Apparel


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Welcome to the latest episode of the Hack The System show!

You should subscribe to this show on iTunes.

In case you haven’t heard, the Hack The System Podcast is your access to interviews with the world’s foremost experts on blogging, lifestyle design, traveling, and life/system hacking. In short–you’re going to learn how to kick ass.

In this episode, I feature Ryan Holiday, author of the bestselling book, Trust Me, I’m Lying, a book about how to exploit the media, and hack marketing and media. He’s currently the Director of Marketing for American Apparel, a media strategist for clients like Tucker Max and Dov Charney,

Ryan and I have a funny past: we went to middle school together in California. For some reason, I remember us as not-friends–enemies almost.

I reconnected with Ryan after college, and found both of us followed similar paths: we both left college without completing it, and then ended up doing work in similar industries. Ryan worked for incredible authors like Robert Greene, who wrote The 48 Laws of Power and The Art of Seduction (both which had a significant impact on my life).

When I began working with Tim Ferriss on The 4-Hour Chef, I found out that Tim had also hired Ryan to help on the book as well. We worked together on the project.

Check out the interview: learn how to manipulate the media, and engineer ways to get your video to become viral.

Watch it here:

Transcript of the Podcast Episode

Maneesh: [00:00:00] Hey, guys. Maneesh Sethi from Hack the System. I’m here today, I’m with Ryan Holiday from Ryan and “Trust Me, I’m Lying: The Confessions of a Media Manipulator,” your new book. What’s up, Ryan?

Ryan: [00:00:13] Thanks, man.

Maneesh: [00:00:13] It’s good to see you. It’s good to see you again, yeah. It’s been a while. So Ryan and I actually … a funny story. We went to middle school together.

Ryan: [00:00:19] Yeah.

Maneesh: [00:00:19] I remember sitting next to you in Ms. Thatcher’s class. And then … Did we go to high school?

Ryan: [00:00:23] No. I moved and then you went to Bella Vista, right?

Maneesh: [00:00:27] Yeah.

Ryan: [00:00:27] And I went to Grand Bay.

Maneesh: [00:00:28] Got it. Yeah, I remember like seeing Ryan’s name pop up and I remember talking about how there’s very few people from our high school ever did anything interesting.

Ryan: [00:00:35] I think there are very few people from our generation that are doing anything. I feel like they’re still in school or they’re living at home with their parents sort of trying to fig – like the economy and sort of the toughness of the job market so overwhelmed everyone that they’re just like still reeling from it.

Maneesh: [00:00:53] It’s definitely true, and one of the biggest themes that we’ll be talking about today is about pursuing excellence or becoming … like doing something in our time [inaudible 00:01:00]. But before we get to that, introduce yourself and talk a little bit about your book. I think it’s interesting.

Ryan: [00:01:06] Yeah, so in my day job I’m the director of marketing for American Apparel, the fashion retailer. Then I work with a bunch of different bestselling authors, public figures, strategists, and I advise them on Internet marketing, marketing and just sort of general all around strategy. So the book is sort of an expose of what I feel like is the dark side of that business, the forces that control what we see and hear online. The first half of the book is sort of the how-to for how to do all this stuff for people who’d want to do it. And then the second half of the book is for people who want to sort of enlarge their perspective about this. It’s sort of the consequences and the risks that playing with these dark arts entail.

Maneesh: [00:01:49] Yeah. The first half … what was really interesting for me, I was like taking notes on my … how can I [inaudible 00:01:53]?

Ryan: [00:01:53] Right.

Maneesh: [00:01:54] How am I going to get myself up there? The second half of the book was interesting about the consequences, and I feel like there might be a shift from – like for you, at least personally, it seems like you shifted from wanting to get into the media to not wanting to get into the media. You found that to be true?

Ryan: [00:02:08] Yeah, I think that’s part of it. It’s like I understand the game and I understand these are the things that people need to do to get attention in an attention economy. But then there’s another part of me that understands sort of what this all means when everyone is fighting each other for that attention. Like what does it mean when there’s a million blogs trying to be heard over a million other blogs? It’s really quickly a race to the bottom, and I think sort of intellectually, I began to understand that maybe this isn’t the right way to do it. That’s not to say that this isn’t how you do it today but is this the long term system we want to have?

Maneesh: [00:02:43] So Ryan said that you worked with some authors that all of my readers are definitely familiar with so you worked with Robert Greene, Tucker Max –

Ryan: [00:02:50] Yeah.

Maneesh: [00:02:51] Oh, Tucker Max. And then “The 48 Laws of Power” was written by Robert Greene, right?

Ryan: [00:02:54] Yeah.

Maneesh: [00:02:54] “The Art of Seduction,” my favorite.

Ryan: [00:02:56] Yeah. Tucker Max wrote the book, “I Hope They Serve Beer in Hell.”

Maneesh: [00:03:00] Yeah, the number one New York Times bestseller. I think it sold something like two million copies.

Ryan: [00:03:04] Inspiring for people who are into the game.

Maneesh: [00:03:09] Yeah. And then have you worked with any authors that we know?

Ryan: [00:03:12] Yeah, but those are the only authors that like me talk about our association. Understandably, some people want to play the game but part of the game is keeping your hands clean, straight from “The 48 Laws of Power.” They don’t want to be associated with these tactics and frankly I don’t blame them.

Maneesh: [00:03:29] That makes sense. That also makes sense that Robert Greene and Tucker Max don’t mind.

Ryan: [00:03:33] Right.

Maneesh: [00:03:34] (Laughs) They don’t mind having a [inaudible 00:03:35] media strategist working with them. So how many people work with you at American Apparel? Like so how does the org chart go?

Ryan: [00:03:42] Yeah, so I run the marketing department at American Apparel. It’s probably seven to ten people. And then obviously it’s a fully vertically integrated company so instead of … if you’re the VP of marketing, I would say like Coca-Cola, you’re not designing your own advertisements. They’re not being made in-house. But American Apparel does its own photography, does its own design, does its own ad buying, and then we do everything from the product design to the shipping, the retailing and the publicity.

Maneesh: [00:04:12] You got the whole company completely running. It’s all based in the US?

Ryan: [00:04:14] Yeah, it’s not only all based in the US, it’s actually all based in two buildings in downtown Los Angeles.

Maneesh: [00:04:19] Really?

Ryan: [00:04:19] Yeah. So like right outside my office is sewers who are sewing but I think the factory makes about 15 million garments a year.

Maneesh: [00:04:26] So I want to talk to you about a little bit how did you get into this game? I know you first met Robert Greene, right?

Ryan: [00:04:33] Yeah, I met Robert. When I was in college, I started working for Tucker. I was helping him with various Internet problems. I sort of emailed –

Maneesh: [00:04:41] How did you meet Tucker the first time?

Ryan: [00:04:42] Yeah, I was like, “Dude, I want to work for you. I’ll work for you for free. You don’t have to pay me anything. I feel like I could contribute to what you’re doing, and the potential downside here is zero dollars.” So he accepted that, he started teaching me things, I started learning things, took a lot of initiatives and I sort of figured out how all this stuff worked. And then I had lunch with Tucker and Robert was there in Los Angeles. This would have been like 2007 or so. And Robert, sort of having similar problems, he was researching for his book, “The 50th Law,” and he couldn’t find a good research assistant and I sort of jumped on it again. I was like, “I will work for you for free right now –“

Maneesh: [Inaudible 00:05:23].

Ryan: [00:05:24] Yeah, [inaudible 00:05:24] wasn’t doing the research. Robert is obviously a high level strategic thinker and there were just certain things that he wanted someone whose time was basically worthless, which was me, to go out and chase these leads wherever they would go. And so I spent hours and hours reading whatever books he asked me to read, marking passages, tracking things down. And, you know, I was very fortunate to be able to contribute to that book and sort of went from there. And then, through Robert, who’s on the board of American Apparel, I met Doug who is the CEO and owner of American Apparel and, again, Internet problems that I’m sort of uniquely equipped to deal with and I came in and I never left.

Maneesh: [00:06:07] Got it. So you stayed working with American Apparel even through all of these ups and downs and you’re writing your book. Why do you continue to stay with American Apparel?

Ryan. [00:06:15] It’s weird. I don’t think I’ve ever stopped working for anyone.

Maneesh: [00:06:19] (Laughs)

Ryan: [00:06:20] I still work at all the clients. It’s like every time I meet someone new or new company, I say yes to the opportunity without thinking whether it’s going to … what’s that going to mean for my other things and I just sort of like expand my amount of working hours to facilitate that. So I’m very anti-four-hour work in that regard.

Maneesh: [00:06:40] I remember like in seventh grade my dad told me, he’s like, “Hey, I need somebody to help update our site, the website for our church.” I’m like, “Yeah, I …” He’s like, “I’ll give you $35 one time.” That’s such a steal. So now, until today, I still have to update his website.

Ryan: [00:06:54] (Laughs) You guys never renegotiated?

Maneesh: [00:06:56] I haven’t renegotiated the contract yet so it’s like … you got to be careful sometimes but what I noticed is that people who tend to excel, especially at young ages in our generation, always leave the door open to yes. They say yes a lot more. I think you’re 26? 25?

Ryan: [00:07:10] Twenty-five.

Maneesh: [00:07:10] Yeah, you’re 25, I’m 24. At our age, it’s important to say yes and to try to do new things ‘til you achieve these goals and you don’t know what [inaudible 00:07:18].

Ryan: [00:07:19] I mean unemployment for people our age is like what, 25%-30%? If you’re saying no to opportunities, there’s something wrong with you.

Maneesh: [00:07:26] Did you meet Charlie Hoehn at your book launch party? Have you met him before?

Ryan: [00:07:31] No, I met Charlie three-four years ago. I’m a big proponent of … I’m sure you’ve read Charlie’s book, “The Recession-Proof Graduate,” where he’s like saying, look, the way to getting a job is not like applying through some traditional process but it’s sort of like free apprenticeships and, I mean, I’d already done that before I met Charlie but when I read that book, I was like, “This is exactly what I did myself,” and so I totally support that. And it’s weird now, it’s hard for me not to think that way. It’s weird for me to ask people to pay me for what I do because I’m still so eager and hungry to work on cool stuff that it’s almost weird to have that discussion about money.

Maneesh: [00:08:16] Yeah. On my way over here, my roommate walked in while I was checking my email. I had an email from somebody that said, “I want to work with you on your … I will update your Facebook page and your email list for free,” and I would [inaudible 00:08:27]. And I’ve already had this guy do some work for me. He’s pretty good so we’ll talk about hiring him later. But my roommate saw his picture and he saw the headline, he’s just like, “Why would somebody send that email out? That seems like a bad way to get at this opportunity.” No, actually, it’s a good way to get to the top of the …

Ryan: [00:08:42] I think it’s kind of the only way because if you think about the competitive advantage that young people have, it’s that their cost of living is so much lower and the value of their labor is lower, and you’ve got to exploit that because you’re competing with people who might have ten or 20 years of experience that just got laid off that are willing to fight for those same entry level positions as you.

Maneesh: [00:09:03] Exactly. So say you’re just out of college, a 22-year old, 23-year old, and let’s say you have an interest in a lot of different things but you [inaudible 00:09:11] and you really don’t have any skills that are sellable. What would you do? Who would you approach? What exactly would you do to figure out a way to a path through life?

Ryan: [00:09:21] I don’t know if you want to talk specifics because I don’t know who … I feel like it’s hard to say, “You should approach this person,” because I don’t know who we’re talking about. But I think I would do exactly what Charlie says, which is find someone whose work you’re passionate about, whose space you’re already familiar with and have done research on, who you feel like you could add value to their operations. And then the twist I would add is look for someone who – Let’s say you want to work with an author. Don’t email Stephen King and say, “I want to work for you.” Find someone who’s about to publish a bestseller or who is sort of getting a lot of buzz or is just sort of developing so when you help them, you’re fates rise together and you’re not going … like don’t … if you want to network with important people, don’t crash a Richard Branson party and hope that you can sort of connect with him immediately. You know what I mean? Start small and build up a base and that’s why I would focus on developing people because not only is your access easier but you’re efforts are going to have more of an effect quicker than something that you do with Stephen King.

Maneesh: [00:10:32] Absolutely.

Ryan: [00:10:33] So it’s important to check the tiers of the people you’re talking to. If you jump right to the top, it’s really tough. But when you start low, you can grow kind of like you’re blogging … kind of like getting a post in the first half … kind of like getting a post on the Huffington Post –

Maneesh: [00:10:46] Yeah, right.

Ryan: [00:10:46] Exactly the same way. So don’t go pitch to the New York Times, pitch to the Huffington Post because they have different sets of standards and not to say that one is worse than the other but one is more accessible and likely and realistic for what you’re trying to do.

Maneesh: [00:11:00] So I see these emails that come from my readers. A lot of times it’s very interesting to see these emails because people are so afraid about achieving their passion and they’re not doing what they should be with their life. And I just went to this conference called The World Domination Summit and speaking there was one of my favorite authors. His name is Cal Newport.

Ryan: [00:11:18] Yeah, yeah.

Maneesh: [00:11:19] Are you familiar with Cal Newport?

Ryan: [00:11:19] Yeah, he’s the [inaudible 00:11:20] education guy, right? Study X?

Maneesh: [00:11:23] Yeah, exactly. And he had just released this new book. Well, it’s not out yet but I read it, the pre-copy, and it’s called “So Good, They Can’t Ignore You,” and it’s about why following your passion is the worst advice you can possibly have. And the way he said it, the way he showed, he showed the chart of the etymology of the words ‘follow your passion’ and it’s a complete inverse correlation. It only started being said in 1980 and it’s an exact inverse correlation with the use of that word in books and job satisfaction, and it’s like a very funny graph. And so what he was saying is that he did a bunch of interviews, he did a bunch of studies where he looked at people who are passionate about their jobs and he found that the only recurring trait of people who are passionate about their jobs was the amount of time that they spent at that job – essentially, that it was passion was built; it wasn’t found. And so his recommendation was when you’re young, look at your interests, not your passion because nobody has a [inaudible 00:12:17]. But with your interests, especially the ones that you think you can leverage in the future, you can get really good at this skill, like video editing or email marketing or working with getting people’s website popular, those are skills that you’re going to be able to leverage in the future. Look for an interest, work really hard at it, develop your skill as a craftsman and then use that in the future to leverage at the traits of the job you want.

Ryan: [00:12:40] Yeah. I think that you want to find a convergence of your passion plus your skill set and also does that fit into some sort of profitable market, right? Like, let’s say, you’re really interested in collecting Russian nesting dolls. That’s probably not a passion you want to pursue as a career so you want to find something that you’re good at and you also – I had no idea that I was interested in PR, that I was good at it. I just sort of … I was interested in reading about it. I was reading about it and I wanted to test out some of my ideas. And so I sought out some of my … Tucker who gave me an opportunity to do that and it just happened that the first thing that I picked worked out for me. But maybe I would have hated it and then I was … I set myself up enough that the cost of failure was cheap so I could still try other things.

Maneesh: [00:13:30] Yeah, exactly. So you worked for Tucker for free. It’s not like you’re hired into a two-year contract.

Ryan: [00:13:35] Right. If things work out, then they work out.

Maneesh: [00:13:37] And was he already popular at this time or –?

Ryan: [00:13:39] He was a popular blogger but his book hadn’t come out. And I think so when people go, “I’m good at arguing. I’m going to go to law school.” That’s the worst thing that you can do because you’re not just experimenting with something, you’re putting down like a hundred thousand dollars and two years of your life that you can never get back and you’ve never even actually tried. It’s like spending all this money to qualify for a career that you may or may not like. And that, to me, is a risk that I’m not willing to take.

Maneesh: [00:14:09] Big college is one of those big scams that scares the hell out of me. If you need to go to college –

Ryan: [00:14:13] I dropped out at the end of my sophomore year. But, again, I didn’t even … I liked school, it’s just I had this opportunity to do this thing over the summer which was I was working at a talent management agency that was representing Tucker and I was sort of shepherding his projects through that company. And it turned out that I loved it and I wanted to do it. And then that option was better than college so I didn’t go back. But that only came about because I was willing to pursue an interest and pursue a skill that’s sort of a nascent skill that became more than just a nascent skill and became a full-blown talent, and then it was like ‘do I want to go back … do I want to put all this shit on hold to go back to school to not be able to do what I want to do?’

Maneesh: [00:14:55] It makes sense that people today, especially when I was in college – and I saw your guest post on, which was about dropping out of college and why it makes sense – I feel like there’s a … ever since we were young, we were being told that you have to go to college, you have to go to college, you have to go to college. I know we went to the same middle school and we were told that every day.

Ryan: [00:15:11] I mean we were … in middle school, we were being trained to go to college so we were taking our high school classes in middle school so then we could take our college classes in high school so then when you get to college, it’s like … and then you get to college and you’re like, “Wait. This is what I was preparing for?”

Maneesh: [00:15:27] It’s easier than high school.

Ryan: [00:15:29] It’s not only easier than high school, you’re doing the same dumb group projects, the same crappy study groups, and … I don’t know … I just thought college was going to be like bastion of learning and everyone was going to be talking about books and theories and all this neat stuff and then it turns out it’s like none of these people care. They care even less about learning than they did in high school.

Maneesh: [00:15:49] Exactly. There’s not even like a segmented AP class anymore, which is everyone with the same skill. And I find that … I advise all my readers who are in college. They’re like, “So what do I do? You know, I have this opportunity [inaudible 00:15:58] from school.” And I’m like, “Listen, guys, the only reason that we think school is important is because our parents tell us it’s important and their generation.” And when they were in school, it made sense. You go to college, you will get a job. That’s how it was 40 years ago. Today, things have changed. Prices have gone up and the quantity of people trying to go there has gone up and the amount of jobs has gone down.

Ryan: [00:16:18] And the value of the degree is roughly the same.

Maneesh: [00:16:20] Exactly.

Ryan: [00:16:21] And I think – although, what I tell people about dropping out is don’t just drop out for the sake of dropping out. You need to have another option. College is a great placeholder option. It’s what you should do in the absence of any compelling other options. But if you’re thinking that just going to college and then you graduate, there are going to be people knocking down your door to give you the job of your dreams, then you’ve got another think coming.

Maneesh: [00:16:48] My graduating year, I took several years off at Stanford and the year before I was there, there was an 81% employment rate coming out of Stanford. The year I dropped out was 2008, and there was an 18% employment rate from Stanford University. It was like unreal.

Ryan: [00:17:04] Yeah. I mean, like –

Maneesh: [00:17:05] I think times have changed and suddenly even the best and brightest universities can’t get jobs.

Ryan: [00:17:09] I mean I think the majority of all dropped college graduates return home and live with their parents after they leave school. So, to me, that’s like the scariest on the world. That’s way worse than being out in the world and not having a degree. I’d rather have my own apartment than a degree and live with my parents.

Maneesh: [00:17:24] Absolutely. So you seem to be one of these experts in networking. You’re really good at meeting the right people, getting you ahead. And you said it started off getting lucky at the beginning by just like stumbling … I guess getting lucky but also putting up effort – to me, Tucker Max. Since then have you found any traits or any patterns that will help someone meet the people that they think they need to meet?

Ryan: [00:17:46] Yeah. I mean, I think if … so old friends, it’s like when I talk about blogging, like how to sort of get stuff on blogs, right? And then people always go, “Well, so what blog should we get on?” And to me that’s like, wait, if you don’t know what sites are popular in your niche, then you don’t care enough about your thing to really be giving it a go in the first place. If you’re not reading all the influences in your space, you’re not doing your job, right?

Maneesh: [00:18:12] That’s true.

Ryan: [00:18:12] And so, for me, I don’t see networking as being the separate end or this task that people should do. If you’re not so interested and passionate about your space that you want to meet the leaders in it and you know who they are and you’re sort of like traveling in the same circles, it’s like you’re not doing your job. That’s the way that I look at it. I don’t look at networking as being this special thing I do on the side. It’s like I care about what I do and I want to get better at it and I want to know all the secrets and tricks, and so meeting and talking and trading information with the people in my space is like the best way to do that.

Maneesh: [00:18:47] That makes sense. So your book is basically about how to get things, like how to get articles are written from [inaudible 00:18:53] to blogs up to bigger and higher to your blog spread.

Ryan: [00:18:55] I’ll give you an example of some marketing we’ve done for American Apparel. Yeah, like we just did this campaign last week where we used a 60-year old model, like basically an old [inaudible 00:19:06] in one of our ads. I think the photos are really compelling and they’re really interesting, and they ended up being all over the Internet, all over the media. They probably did millions of impressions. But people don’t know, we spent $1,500 on that ad campaign. [inaudible 00:19:20] about $50 an hour so the cost of using the model were incredibly great but the way we marketed that campaign was we bought space on an influential blog for not a lot of money and then we knew that if we made something that was so interesting and so compelling that people couldn’t not talk about it, that ad would stop being just an advertisement and start being sort of a social object, like a source of discussion and it would cross the boundary from ad to content; and we design our campaigns with that in mind. How do we make this become something that people talk about? And that tiny story broke on, I think, a blog called, and it ended with stories in the Hollywood Reporter, the Daily Mail in the UK, you know, huge other blogs like from Gawker and Jezebel to AdWeek. And that was because we did something that was cool and interesting but we traded up the chain from a tiny blog to basically the biggest sources in advertising.

Maneesh: [00:20:21] So you engineered your campaigns to be viral, have a [inaudible 00:20:25] into it. You also have a new … in like apparel, so it’s going to be shaped and then thrown upwards on its own. But, say like Ryan, you got your blog, your own personal blog, Ryan, and so have you done anything with that to try to get it to spread virally?

Ryan: [00:20:39] Yeah, I mean, that happens all the time where it’s like you write a story and Tyler Cohen of Marginal Revolution … you know he reads your blogs so he gives you a link. And then you know that the LA Times reads Sarah [inaudible 00:20:50]’s blog, and so the next thing you know, you’re being featured in the LA Times. But if you pitch to the LA Times, they’d never be interested in writing about you because they’re like, “Who the fuck are you?” But when you sort of pop up on their radar organically, then it’s like they’re discovering you and they’re more than willing to talk about you and your stuff.

Maneesh: [00:21:09] So it’s kind of like have a friend recommend you to be on a blog rather than emailing blogger directly, saying –

Ryan: [00:21:14] Right. You’ve got to cultivate a list of influential readers who have bigger platforms than you so when you … because not everything you write is destined to go viral. I’m not as good as the guys at [inaudible 00:21:29]. That’s not what I’m trying to do either. I don’t do this full time. But if I know that the people at [inaudible 00:21:35] are reading my stuff, when I do something that fits with them, they’re going to popularize it for me.

Maneesh: [00:21:40] Makes sense. It’s also interesting that like you talk a lot about engineering your content to the top valence to either be positive or negative but to inspire emotion – not sadness but anger or posit intense support.

Ryan: [00:21:54] You’ve got to provoke a reaction if you want people to have a reaction. You can’t just hope that what you do resonates with people. You’ve got to think about what resonates with people. You’ve got to deliberately try to attain that. Otherwise, you’re just hoping, and hoping doesn’t work.

Maneesh: [00:22:11] So what did [inaudible 00:22:11] the in blogger to like … say, for example, I have a friend in Benny Lewis who writes a blog about [inaudible 00:22:17] language and his most popular post of all time, which is crazy popular, is called “21 Reasons I’ll Never Live in the United States of America.” And, of course, you look at the comments, it’s like 50% are saying, “Yeah, fuck the US!” and the other half are saying, “You guys are idiots. It’s the best place to live in the world.” And that makes sense for him because it’s true. But I feel like people might read this book and then they’ll launch a blog that’s just designed just to have viewpoints that are contrary or inspire anger. And you think that for a beginning blogger, that might be a bad –

Ryan: [00:22:46] Yeah. I don’t think this is something you pursue all the time. And I don’t think this is something you pursue off the bat because, first off, you have to have a base audience of people who support and like your stuff. Otherwise, you just become sort of … otherwise, you’re just better of writing articles for Cracked, you know what I mean? Your one-off articles for other sites and get paid to do that but if you’re trying to build your own site, I think you want to mix sort of crazy pieces that bring people in and then also the day to day content that makes people read regularly.

Maneesh: [00:23:18] That makes sense. And do you think that there’s a quantity that should be used for up and coming bloggers?

Ryan: [00:23:23] I think you can get really Asperger-y about it and sort of like saying, “Oh, 20% of your post should be this and 20% should be that.” I don’t think about it like that. I just think you’ve got your audience who you want to serve and then you’ve got all the people out there who don’t know about your stuff that you want to know about your stuff. And you’ve got to throw something out; you’ve got to reach out to them occasionally to bring them in. And so I think guest posts are a great way to do that because, that way, you’re writing the really solid consistent stuff for your site for your loyal readers and then, every once in a while, you’re going out there and you’re putting something on a different platform with different rules and you’re acquiring lots of readers, like your how to learn any language in 30 days post that you did for Lifehacker and stuff. If you’ve done that on your own site, would it have been as popular?

Maneesh: [00:24:12] It wouldn’t have been popular at all.

Ryan: [00:24:13] Right.

Maneesh: [00:24:13] And that’s actually one of the biggest problems I had is thinking about like I have all of these really high-quality 2,000 [inaudible 00:24:19] waiting. And if I posted on my site, there’s like a couple of hundred hits. It’s like is it worth even posting on my site?

Ryan: [00:24:25] Yeah, and I think about saving those things or maybe you get a guest post on the Huffington Post, maybe Forbes lets you write there, and those are good places because they want that more high-quality content, those longer pieces that if you even post it on your own site, it’d be too long and no one will read that. So you might as well use them as a free way of acquiring new users.

Maneesh: [00:24:48] And I was also … a question I had for you from your book was about the length of posts because I’ve always learned … well, I’ve always tried to write extremely high-quality posts that are 2,000-plus words, and you mentioned a usability expert –

Ryan: [00:25:03] Yeah … Nielsen.

Maneesh: – [00:25:05] about that all posts should basically be removed … 40% of it should be removed and you’ll only lose 30% [inaudible 00:25:10].

Ryan: [00:25:10] Right.

Maneesh: [00:25:11] So how do you feel about the length of posts?

Ryan: [00:25:13] What I was trying to say there is that’s the prevailing wisdom on the Internet. I don’t necessarily agree with that. I’m just saying when people for business insiders sit down and write posts, they think, “How can we make this 800 words or less.” They’re not thinking about making high-quality content because they don’t get paid to do that. You want to write a 2,000-word, high-quality piece because you know you’re not making money on the piece, right? So you want to do something that spreads your brand, gets high-quality readers and generates positive brand association for you. If you’re a churn and burn blogger, that’s just sort of outside of your job description.

Maneesh: [00:25:50] That’s true. So a lot of campaigns you’re talking about are bringing in like Huffington Post, bringing in just as much traffic for page views or ad clicks. It’s not bringing in email lists or like high-volume subscribers who will continue to subscribe and read your stuff.

Ryan: [00:26:02] Yeah. And I think you got to ask yourself what are you after? Are you blogging for money or are you blogging to develop an audience that you can sell products to or books to or you can do speaking gigs from?

Maneesh: [00:26:13] That comes more from trust rather than –

Ryan: [00:26:15] It’s the difference between playing a short game and a long game.

Maneesh: [00:26:18] Got it. So you’ve seen that the biggest companies these days tend to be trying to run the short game.

Ryan: [00:26:24] Overwhelmingly so.

Maneesh: [00:26:25] So who are the biggest or the worst players in this category?

Ryan: [00:26:29] I think Gawker, Business Insider, most of the Hollywood gossip stuff. Perez Hilton doesn’t care if the story that you break turns out to be right or not because he wants pages from it because he knows that once you click, you can’t unclick. You know, there’s no dislike button and so they just want to get as much traffic as they can day in and day out and they know that they don’t have subscribers anyway. They just have people who put their headlines on Google News. So if you’re an individual blogger, I don’t think it makes any sense to play that game and I think you want to deliberately not play that game and develop a long-term brand.

Maneesh: [00:27:04] That makes sense. So if you guys are trying to start your own blog that will get you a high-quality readership, don’t just write shit that gets you popular for one post.

Ryan: [00:27:11] I mean, I think Tim Ferriss is a great example. The money that he makes from his blog pales in comparison to what he makes selling books and speaking gigs and investing in start-ups. So the last thing he’s going to do is screw his readers over by publishing crap. And I think we can emulate that model and write really high-quality stuff that violates all the supposed rules of blogging and know that we’re doing that on purpose because what we’re trying to build is a long-term valuable reputation with people for quality shit.

Maneesh: [00:27:46] That makes sense. The people I’ve seen who are experts in any industry tend to follow a specific routine, morning ritual or they do something in particular. Do you have a morning ritual that you follow?

Ryan: [00:27:56] It’s been different for me because like writing this book was sort of a new phase in my work life so last year I changed my routine. So I get up in the morning around 8:00. I write usually for like two-two-and-a-half hours and then I do Brazilian jiu-jitsu. Then I have breakfast or lunch, and then I usually answer emails, phone calls. I try to do all my administrative crap in the middle of the day. And then around 2:00 or 3:00, I go to the gym again or I run. So I run, swim or box or do some sort of other physical activity. The reason I do two physical activities is I do Brazilian jiu-jitsu for like because I’m training in a thing that I think sort of takes my mind off stuff. Then when I run or swim, it’s an opportunity since I’ve put all my work aside, like all the writing that I did in the morning that I was struggling with, now I’m processing that and I usually have ideas that I write down and then like … it’s like when you stop thinking about it, that’s when you get your good ideas. So then in afternoon … so I run and swim in the afternoon, which is usually like an indirect way of sort of getting inspiration or ideas. I work again in the evening, take a break, hang out with my girlfriend and then I usually write again at night.

Maneesh: [00:29:07] So you’re working the whole day with specific breaks in between.

Ryan: [00:29:11] Yeah. There’s this cool site – I forget who runs it – but basically the word or the phrase he uses to describe what he does is paid to exist.

Maneesh: [00:29:20] Yeah, Jonathan Mead.

Ryan: [00:29:21] Yeah, yeah. I think that phrase is really cool where like if you’re paid to exist, that means everything you do is part of your job, you know? And I sort of think about things like that. I think like how can I … like no one pays me to read but I know that it makes me better at my job so I do that as part of my job. So I read during the middle of the day and I don’t feel guilty like I’m not doing work. That’s part of my job. Since I get ideas when I run, that’s part of my job, and since it makes me stronger and fitter and more emotionally regulated, I consider it a part of my job. So I work from when I wake up to when I go to sleep but a lot of the things that I do are not work or would not be considered work to other people.

Maneesh: [00:30:06] So when you say that you write at the beginning of the day, that’s like a creative period it feels like.

Ryan: [00:30:10] Yeah.

Maneesh: [00:30:11] Do you write without even opening a laptop or without turning on the Internet, you do not check your emails before?

Ryan: [00:30:15] It depends. When I was writing a book, I would go and I was deliberately sort of disconnected from everything. Sometimes I check my email in the morning. I like checking my email in the morning before everyone else is awake. So it’s like I respond and then I responded before they’re up so it’s sort of a nice subtle reminder that I’m working harder and longer than they are. So I may check my email in the morning but just enough that I don’t get like overwhelmed and sort of in like response mode, and then, yeah, I write. I like to … I usually go to a library and write and I write not on my computer. I use like a library computer where none of my shit is there.

Maneesh: [00:30:57] That makes sense. I like the idea. I feel like the … [inaudible 00:31:01] this course called A Way to Productivity, where he talks about this grey zone for people who are trying to become productive but he calls it the snacking society. Basically, nobody really sits down for meals anymore. People are like eating chips during the day. In the same way, nobody really sits down to work anymore. There’s no 9 to 5 regimen. Now, it’s like Skype is open and chat is open. But breaking that grey zone and building a focus pattern is one of the most important things you can possibly do.

Ryan: [00:31:25] Totally. It’s really interesting. I like when you watch movies, even like Mad Men or something, where they’re sitting at their desk and you’re like, “Where’s the computer?” And there’s no computer at their desk and you realize that it makes me think what do they do from like 8:00 in the morning to 5:00 at night? Are they just like sitting there?

Maneesh: [00:31:41] What do they do?

Ryan: [00:31:42] What does an accountant do? Is he like doing math problems? What was he doing? And you realize there’s a full day’s work in work, not sitting at your computer, you know what I mean? And some of that work is thinking or reading or doing the things that we feel like is not work because we have a computer. That was the hardest part about working in an office for me is like no one wants … none of my employees would want me sitting at my desk while they’re working on stuff and I’ve got my feet up reading a book. But now that I work remotely, I still consider that part of my job. It sort of takes the stigma out of a lot of those work things.

Maneesh: [00:32:23] So how do you see yourself in the future? Do you see yourself moving back to LA to work one on one or –?

Ryan: [00:32:27] I don’t know where I’m going to go. I like New York a lot. I like Los Angeles a lot but then I don’t know. It’s not like the right culture for me. New Orleans isn’t either so I’m going to check out some cities and see where I go.

Maneesh: [00:32:41] New York is a pretty fun place, man.

Ryan: [00:32:43] You like it?

Maneesh: [00:32:43] I’m trying to decide right now where I want to settle down and I’ve been finding that New York or Portland are my two thoughts. I don’t know if you’ve ever been there.

Ryan: [00:32:49] I’ve been to Portland not a lot. I like Austin a lot too.

Maneesh: [00:32:52] Austin is cool, yeah.

Ryan: [00:32:53] The four I had in mind were Austin, San Francisco, New York and Portland.

Maneesh: [00:32:59] No international cities for you, only in the US?

Ryan: [00:33:01] I think I need to settle somewhere in the US for a while. I noticed that since I come … I mean, you know me, right? Always been traveling for years but I’ve noticed that since I’ve come back to the US, having the American culture of working hard really help me focus on the business side. The one thing that I don’t like about New Orleans, even though it’s like a great city and I love the people there, is that you’re sort of out of the loop in the sense that you live in New York or LA, there’s always people passing through. And people only pass through New Orleans to party. And so I’m like missing the sort of random encounters with cool people who are like, “Hey, I’m going to be in New York next week. Let’s get coffee or let’s get lunch.” And I wish if I pick a city, I think it’s really important to pick a city that puts you in the middle of other people’s travel plans.

Maneesh: [00:33:46] New York is so perfect for that.

Ryan: [00:33:48] Totally.

Maneesh: [00:33:48] It’s right. It’s anywhere that anybody connects always flies through New York.

Ryan: [00:33:51] Right, exactly. And people are here for a variety of important reasons. They’re not here on vacation. It’s the truth.

Maneesh: [00:33:58] Anyway, Ryan, thank you so much for joining us for this interview. Guys, check out Ryan’s site at … Is it Ryan or .net?

Ryan: [00:34:05] .net.

Maneesh: [00:34:05] Ryan Ryan also has a really cool email. That’s where he talks about the books that he recommends and you guys should check it out. I’ve read a ton of the books that you recommend. And, Ryan, thank you so much.

Ryan: [00:34:18] Cool, man.

[End of Audio – 00:34:19]

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Chetan January 5, 2014 at 2:44 pm

Great interview guys! You & Ryan are definitely some of the smartest dudes of our time. Cheers


Mike Auerbach January 29, 2013 at 8:44 am

Just wanted to drop in and say that this was a great interview.


Omar January 18, 2013 at 12:21 pm

That was an awesome interview! Maneesh you’re really good at this hosting thing bro! Keep it up.

I hope people really absorb this stuff because it’s really important to achieve success in life. I wish we had more of this kind of material when I was getting out of college.

The Internet is bringing so much to people. I hope people aren’t just wasting it away.


George Mihaly January 17, 2013 at 11:04 am

I loved Ryan’s book and really enjoyed hearing the backstory from this interview. Really excited for his next book on Stoicism and it’s modern day application.

Looking forward to more interviews. Thanks Maneesh! -George


Valerie January 17, 2013 at 8:44 am

Is Ryan responsible for the new wave of pencil-sketched looking American Apparel ads that look like child pornography?

This is not like hiring someone to slap you and getting attention. This is like hiring a model because she looks underage and then using that ickiness to get attention.

Talk about races to the bottom.


Chetan January 5, 2014 at 2:41 pm

Ha! You missed the whole point, didn’t you? Did you even watch the interview? They “actively seek” this kind of a reaction, like the one you just showed, that is what gets them attention which they so desperately want to sell their stuff. So when you actually write about this or comment, you are helping AA’s cause not hurting it ! Quite the irony huh!


Andrew January 17, 2013 at 7:29 am

Really great interview Maneesh. I read Ryan’s book and it sort of disgusted me. I liked the book, but the way media is being manipulated by these huge bloggers is just disgusting. It’s hard now for me to believe what I read when I read bloggers on sites like the Huffington Post. I’m always wondering if they’re writing this because they really are interested in it and have a passion, or because they want page views.


Ryan January 17, 2013 at 7:17 am

Hey guys,

Great info. Also a fan of Charlie Hoehn and the apprentice model. Interesting blog posting strategies. Hey Ryan, I do jiu jitsu too. What belt are you? And who do you train under?


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