Ryan Holiday Dissects Power and Money in Media

He was a research assistant for him who wrote the books on power laws. I didn't get a chance to to talk about that, but we really delved into what's going on with the media, the whole problem with digital marketing, blogging, um, all of the sort of click happy so social media, uh, the filter bubbles that have been created by Facebook and Google and Twitter. Um. It really is an interesting question. He has quite an amazing story. Drops out of school

very young, eventually gets a gig at American Apparel. I think he's twenty when he becomes their head of pr and here it is barely a decade and changed later, and he's five books or six books published, some of which have become extremely successful best sellers. Uh, just really an unusual, interesting, fascinating history for a writer. I found the conversation quite intriguing, and I think you will also, so, with no further ado, my conversation with Ryan Holiday. I'm

Barry Hults. You're listening to Masters in Business on Bloomberg Radio. My special guest today is Ryan Holiday. He is an American author, marketer, and entrepreneur. He is the former director of PR for American Apparel. He is a media strategist and calumnist, and the former editor at large for The New York Observer at the young age of barely thirty.

He is the author of multiple books, including Trust Me, I'm Lying, The Obstacle Is The Way, Ego Is The Enemy, Growth Hacker, Marketing, The Daily Stoic, and his most recent book is Conspiracy, Peter, Theel Hulk, Holgan, Gawker, and The Anatomy of Intrigue. Ryan Holliday, Welcome to Bloomberg. Thank you for having me. So we kind of threw this together pretty quickly. As soon as I saw the book was published.

I've been fascinated by this entire tawdry episode. The new book is an inside look at the Gawker trial um, which we learned was backed by Peter Thiel. This is so different than everything else you've written. What what attracted you to this subject matter? I have the same reaction to the story. I mean, it feels like it's something that should have happened in the nineteenth century. It's what It's what Vanderbilt, a Rockefeller or Carnegie would have done

to an enemy. The idea of this billionaire having this personal grudge for good reasons or batteriasons against the media outlet and then plotting secretly in the shadows to to destroy them sounds epic. In fact, it's not even the nineteenth century. It's Shakespeare or tark or something. The Spanish American War, yellow journalism, all that sort of of behind the scenes manipulation. The most fascinating thing is you had written a couple of columns on Gawker and Field for

The Observer. After this whole thing goes down, both Nick Denton, the founder of Glawker, and Peter Field, separately and unaware of the other, reach out to you to tell their side of the story. What what was that like? It was surreal? I mean, there was one night at the end of two thousand and sixteen, where I had dinner at Peter Teel's house, and then the next night I had uh I went to an event at at Denton's house, and it struck me that I was probably the only

person speaking to these two mortal enemies. These two people had spent north of twenty million dollars fighting each other, that embarrassed each other in the press. What Nick Nick had only recently moved back into his apartment, having had to rent it out on Airbnb to cover the mortgage during his bankruptcy when all his assets had been frozen. And to bring everybody up to speed, feel wins a giant case, or I should say Hulk Hogan in in the guise of his real life persona wins a hundred

plus million dollar litigation. It's bank, it's bankrolled by Peter Field. It ultimately bankrupts Gawker and forces Nick Denton and the founder and soul owner, a majority owner of of Gawker Ye into personal bankruptcy. So these aren't people just having

a Twitter battle. These are really people at each other's throats. No, I mean, this is an epic conflict that it begins in two thousand and seven, when at at Nick's prompting, Gawker out's Teal is gay, So back up a sex So Gawker Properties owns Valley Wag, which was the Silicon

Valley version of a gossip. So Gawker started, it's sort of like a a page six with no limitations, a high hitting, hard hitting in the way that you would need to be a celebrity to be on t M, to be on TMZ or page six, Hawker said, anyone doing something tawdry or provocative or unusual, or that has a secret of some kind is a potential sort of subject for one of our stories. And so so two thousand and seven, what was the title of the post that had come out in Value Peter Teal is totally

gay people. And I think that in one there's a an early Gawker memo that said every post should have a glint of meanness. Yeah, I read that, and I think that that that headline perfectly encapsulates that. It's it's it's not just that you're taking a relatively private figure, someone who is certainly a well known investor, But just because you're an investor doesn't mean people get to know who you have sex with. Or not um. But wasn't by the way, let me interrupt you here, wasn't it

the worst kept secret in the world. I mean, it wasn't that he was closeted. People knew, in fact, the author of that post was gay. And he said half of San Francisco knew Peter Field was gay. Yeah, that that that's what they claim. I think Peter would say, you know, my parents knew, my close colleagues knew. The people I went to college with new perhaps, but that doesn't mean that it should be broadcast to an audience of potentially millions of people. Do you know what I mean?

Isn't that sort of an odd distinction, because if someone out someone who's closeted, that's a terrible violation. Anybody who is gay should feel free to out themselves at a time of their own choosing. But what I find fascinating is this epic battle is started by not even taking something that was private making public, but taking something that was known but not publicized and saying we're gonna take this and spread it around a little bit and put a little glauk Er stink on it. Well, let's say

that you and your wife have an open marriage. Obviously some people would know by definition of it being open, have you heard any Yeah, But let's say I had heard something. Does that mean at what point do you become a fully public figure the way a president or a celebrity or a rock star is a fully public person. And at what point are you sort of on the fringes? And and so I think I think there's some argument over whether it should be private or shouldn't be private.

But what I think there's less argument is this is the sensitivity with which such a subject is treated. Right, So he gets blindsided by this article, and in to some respects, in some respects, it doesn't actually matter whether he should have been out it or not. What mattered is that he felt that it was a grave violation. Right. It's like, uh, it doesn't matter if the Count of Monte Cristo actually was wrong. What matters is that he's

doing in prison about it. So let's ask the question, is Peter Thiel Finskin, should he have let this be? The expression I grew up with, was water off a duck's let's call it back? Or or was this a real slight that wanted this sort of Because it seems like someone shot him with a pea shooter, and he took a bazooker and fired back. Well to that, we gotta go back into time a little bit and think about you know, in two thousand seven, Obama hasn't even come out in favor of gay marriage, so it is

a different issue at the show time. And I think he had his own complicated relationship with his own sexuality. He's a he's a he's conservative, he he's he's private. I think he wrestled with that. I think really what it was is that this is his rude awakening, his rude introduction into this media outlet that operates with the glint of meanness that says the things that other people can't say, right, that that uh, that sort of attacks

publishes first and verifies second. And and you got to remember he doesn't really actively begin to plot against Hawker until probably around two thousand eleven. So it's really this thing that's just sort of bouncing around in his head. And he's just dating. He's he's seeing things that are writing about other people. He's seeing them right about his businesses, he's seeing them right about complete strangers who did nothing wrong.

And it's, as you said, it's just it's just it, and it's growing, and it's this thing that he can't stop thinking about. And that's really where this conspiracy is born out of. Let's talk a little bit about the person who planted the seed in the mind of Peter that there was an opportunity to uh seek his revenge against Nick Denton and Glawker by exploring the possibility of of funding litigation against them. So how who is Mr A and how did he hatch up this whole crazy conspiracy.

So in April of two thousand eleven, Peter meets with this young recent college graduate in in Berlin. And this is sort of his m O. He looks for talented young people, people he's going to invest in. People's gonna place at his startups. The PayPal mafia, which we now see as sort of one of the most powerful networks of investors probably in history, originates because of this habit from Teal. And so he meets with with this young man.

I refer to him as Mr A. Um. I know the identity of the source, but my agreement with the sources that I wouldn't I wouldn't amask him. But uh, they meet and they're talking about Gawker and Tio's complaining and they're they're talking about this unfair coverage, and Peter says, you know, but of course there's nothing you can do about it. And Mr A looks Teal in the eye.

It's it's remarkable that he would have the stones to do this, and he says, you know, Peter, what would the world look like if if everyone thought that way? And this is like the perfect thing you could say to provoke Peter into doing something, And then he goes into this pitch. He says, look, I think, I think buried within Gawker's archives is a number of UH posts that would be UH violation of some law or civil

or or or criminal in one way or another. I think if you, if you put up the money, in the time, the resources, we could pursue causes of action in those instances and eventually be able to hold them accountable. What they did to you out in you is not illegal at least it's on the line, but they may

have gone way over the line in other cases. And so they Peter agrees in this meeting to to budget ten million dollars on this completely insane project that ultimately culminates in a hundred and forty million dollar judgment and Gawker's so good. R O I on that in the at least from a venture capital perspective, and at the time just to put ten million dollars, which sounds like a lot of money into perspective, he's worth. He's one

of the early investors in Facebook. He's been extremely successful as a VC, not just PayPal but Facebook and go down a long list of successful investments. I believe at the time Facebook was about a billion dollar holding for him. I don't know if he was still holding all of it, but yeah, Facebook is going to I p O about one year later, and he's gonna own ten percent of it at the I p O. This is a fraction of his net worth. Uh, this is you know, chump change.

But it is also objectively a way more money than anyone has ever spent on something like this before. The assumption is, hey, if you had ten million dollars to burn through, could you find a more productive usage for it or is it just simply self indulgent revenge? Well that that is that is the question. But Peter has come to say that he believes this is the most philanthrop thing he's ever done. His point was he believes

that we've sort of accepted this idea of technological determinism. Right, Blogging is invented Gauger's Gauger is an outgrowth of that of that that technology, and then we're as a society just sort of a slave to whatever this thing does. Right for Recruider much less genteel because of no holds barred. And you could argue we have the same attitude towards our cell phones, towards Facebook, towards Twitter, like this is what it is, right, it was invented with this is

and and Peter Peter sort of rejected that idea. And he thought that Gawker was this sort of representation of everything he felt was wrong with the media. And then if you could do something about it, if you could hold them accountable in quarter, you could, you could wipe them off the face of the earth, that it would

actually change the direction of culture. I think this is what so so it's ideological in addition to being deeply personal and and sort of revenge based, right, It's it's this complicated mix of motivation, and we should never underestimate the ability of of ideologus to rationalize any behavior in furtherance of the cause. Well, and probably never underestimate the ability of extremely wealthy people to rationalize whatever their preferences as being part of the greater good. So let's let's

discuss the pushback to that. Some people have looked at this and said, hey, it's concerning that an angry billionaire has the ability to effectively close down a media outlet. Are we going to now have to start treating the point oh one percent and point o one percent with kid gloves? Isn't this a direct contradiction of the First Amendment and a robust free press in a democracy. So what Peter would say is that this case had absolutely nothing to do with the First Amendment. This was an

invasion of privacy claim. And in fact, when they when he sits down with Mr A and then ultimately Charles Harder, the lo or that they hire to litigate these cases, they are specifically looking for cases that are not liabele

in defamation. They're looking for copyright violations, UH, violations of of federal trade laws, violations of UH, you know, individual privacy that and so the reason they end up suing Gawker in Florida UH is that the they're running a sex tape of of an individual is is of a very sort of specific violation there uh that they can ultimately be held accountable for. So they picked Florida because

of the state laws. What was anybody related in Florida? Anybody? Well, Hogan lives there and that's what what is his his terry Terry Balaya. So one of the things that strikes me about the book, And I was talking to you offline saying I didn't expect to like it, but I'm really enjoying it, and kudos to you. It's really well written. Um, having only read The Daily Stoic previously, I was not expecting this. But one of the things that struck me

is everybody involved is just a wholly unsympathetic character. You you may be impressed with their intellect, but everybody here is a bad after in some way. And yet it's kind of a compelling narrative. Well, I think it's extremely compelling, just and almost unbelievable what actually happened. You know that it's these two Florida DJs and a professional wrestler and somehow Donald Trump ends up entering the story at the very end. The DJs not get ted because they literally

stole property and then released it. You would think their liabilities on them as much as anybody. Well, I mean, one of the weird arguments, and this is where it gets so sort of conspiracy theory esque, is that the FBI investigates the person who stole the tape, and the lawyer who was brokering the tape decide declines to prosecute

despite having overwhelming evidence. And then that lawyer is the same lawyer who now represents those two porn stars who are accused of of gring secret deals with Donald Trump in the in the two at the end of the two thousand and sixteen campaign. So the whole story is insane. But I think part of that, the sordidness and the the the quickness with which you want to judge the person who you disagree with most has has actually blinded

people to what happened. And I think one of the reasons, one of the reasons I wanted to write this story and why I was so focused on it, is that beneath all that there is a level of sort of extreme competence and ruthlessness and effectiveness. It's a triumph of planning and organization, that he did this thing that everyone thought was impossible, right underneath the noses of everyone who

was supposed to be looking into it. And and and I think we've got to first understand exactly what happened before we make those judgments. And I think, you know, the media has done a poor job covering this story because they're either obsessed with the sensational aspects or they're so self interested in afraid that this could happen to them.

The fact that first, for instance, I'm the first person to report on the existence of Mr. A not his name, but that he even existed in one of the most covered stories in the history of media, is in some ways incredibly alarming. It's like the media was so quick to jump to conclusions they thought Peter Thiel was the personally, you know, reviewing legal briefs in the in the ky

which is absurd. And so I want, I want to we've got to understand how power works, because I think this is indicative or perhaps a sign of what's to come now that Silicon Valley is in some ways the power center of the entire planet. We were discussing earlier the role of the media in this book, and how they really kind of dropped the ball it. It seemed that the more salacious aspects lead to very sensational coverage. Tell us about how Mr a came about in your

your understanding of how this whole a fair unrolled. I remember I was first interviewing Peter and he mentioned you know. I was like, how did you get this idea? And he says, oh, well, I was in this meeting and this you know this person. I was, what, there, there's someone other than you involved in this. This is unbelievable. Nobody had reported about it, Nobody had said not until

after the book came out. I think BuzzFeed out and Mr Ray and I know you're not allowed to confirm or deny, but if you google the book and BuzzFeed, you could get at least one person's best guests, right, and and and and that story only breaks because my depending release of the book. Right. So it is it is incredible that this man's identity was able, not again not just his his actual name, his legal name, but

that his role entire whole episode. And and in fact, that was what allowed the conspiracy to be so successful, is that there was at you know, three levels or three layers removed between Peter and whole Cogan, and that was able to separate these things. You know, I think Peter said to me one time when I was asking, he said, you know, I think what was so incredible to me. He's like, I was so paranoid people were

right about to discover us. And then he said, in retrospect, I realized they weren't even thinking about what it wasn't even looking for. And he said this about his investment strategies. He says, it's not so much that people often think that I'm wrong about one of his big contrarian bets, is that they're not thinking about it at all. Um. And those are the opportunities that he actually looks for.

And I think the media, even after this, even after his identity and Mr A's identity is broken again, is so focused on, you know, what this means for their business, rather than communicating facts to the public. Um. You know that that again we sort of get this weird sell this media bubble around these really important issues. And I think this applies as much to the coverage of this case as the coverage of Donald Trump or the coverage

of any sort of controversial thing. We were told why we should be outraged, but we're not really fully explained to what the thing is, what the facts are, and this is a weird filter bubble that we're in. So let's let's talk a little bit about your background and how you ended up becoming, uh, this media scourge. You drop out of college to take a job at a Hollywood talent agency. That sounds like a risky plan. What were you thinking at the time? That was the question

my parents, of course asked At the time. I I felt like this was you know, this is two thousand seven sort of media is in this uh, media and technology and cultures in this weird shift, we're embracing all these new trends, and I just thought, why would I stay in school when I have the chance to sort of do things in the real world, right, Like, why would I stay in school and then hopefully read about the things that I was going to be doing rather

than you know, actually going out and doing them. And so I sort of got a you know, a jump on people of my age group. I you know, I skipped two years of waiting in line essentially, and and I happened to end up working for a number of really controversial clients, and I think it sort of showed me a wait, this is how the sausage gets made on sort of on the marketing side, on the news side. And then my first book ended up being this kind of expose of that, which was very controversial at the time.

And then ironically, you know, given that I wrote this book about fake news, was probably five or so years early to the entire trend, you know, all about fake Twitter accounts and media controversy. So since you wrote that book, how many years ago? It's almost a decade ago. It came out in two thousand and twelve. Okay, so six years ago, seven years ago. Uh, fake news has become a presidential utterance all the time. Uh, Facebook, Google, Search, Twitter.

There are all sorts of these accusations that not just the mainstream media, but the technology aspect of that completely dropped the ball in this How has the entire media landscape change society? And what does this mean for us in a democracy where you can almost argue that sort of an equivalent to the financial industry and that, you know, the financial crisis, there had been a number of warnings.

They were sort of the writing on the wall. There were these people who are pointing out problems and then they sort of you know, greed and self interest sort of motivates people to sort of push past that, and

then you get this sort of catastrophic failure. I think in in media, we've had a similar situation in which the incentives were toxic, uh and complicated the you know, the idea of paying people by the page, you the idea of of sort of most the news being filtered through these social networks where they have to either go viral and if they're not, then no one sees them. These incentives were were there, and they were brewing, and you know, I wrote about it, and many other people

were like, look, this is dangerous something. This is ripe for manipulation. Not only is this rife with miss manipulation, it's right for very serious manipulation. And they sort of slept walked on and and you know, Russia and you could argue, Donald Trump and and other people sort of figured out the loopholes in that system where the weak points, and they've hit them so many times that that that

now where where we are. You know, whether it's uh tens of thousands of fake accounts by Russian bots, or whether it's Donald Trump getting two billion dollars worth of free publicity by sort of leveraging this constant controversy and outrage. And then we wonder why we're in the situation we're in. There's this old quote from a media critic, and he says, you know, America as a country governed by public opinion.

So what governs public opinion governs the governs the country In the nineteen in the early he said this, it was newspapers, but now it's blogs and social media and and and the sort of online journalism. So let's talk a little bit about blogs. You you wrote, the business model for blogs and cars is publishers and writers to value the click above other potential goals like truth, accuracy, and fairness. So once that toothpaste is out of the tube,

is there any putting it back? Or are we just stuck with this somewhat reckless, not quite mainstream form of of media. I think we're stuck in some ways, although there there is some you know, things to be optimistic too. I think, for instance, one of the reasons we're seeing this massive uh sort of land Russian podcasts is because podcasts aren't subject to those same toxic economics right, A podcast is this self contained unit. It's long, it's deep,

it's thoughtful. There's no viral headline that makes people share it. It's you subscribe to this podcast and you listen to it, and you have this relationship with the host, and they have a reputation to a pold that's very different than the Huffington's Post trying to churn out as many articles as they can per day to get you to click on one thing, and whether they burn you, they don't care because they know in six months they'll get you

on another one. I was gonna call this Ryan Holiday's sex tape escapade, but you're telling me that's just too clicking and not not what my listeners want to hear. I imagine for the most part, the titles have very little impact on whether the difference between your episodes probably has more to do with the guests than the provocative nature of the headline. It's the quality of the content, but that doesn't exist in web or print based media. Well.

I do think you're starting to see some improvements with paywalls, for instance, like if you think about the I write about this in trust Me, I'm lying Tyler Cowen, the brilliant economist is yeah, he's the best. He was saying, you know, what are the what's the economics of of a paywall? It's saying, Okay, the first five articles are free, the first ten articles are free, and everything else you

have to pay. So now they're incentive is to write at least eleven pay worthy articles, right, They they've got to get you. That's very different than I've got to write as many articles as I can to trick you into reading to get a halfpenny of advertising revenue each time. And some of the kids at glkers, and they were kids, were doing eight ten posts a day, seven days a week. It sounded like a relentless grinds. I mean, it's a digital sweatshop in some ways. And and you know, for instance,

is the headline. You would never you would never want a Bloomberg reporter to be writing about a stock that they own, right, that would be a conflict of interest. But what if the Bloomberg reporter is paid and this is how it was at GAKRA and it is still at many blogs. What if you're paid based on how many views your article does? Right now, your stock is the content, right, so you're not gonna You're not gonna write a complicated, nuanced piece without a strong conclusion. You're

gonna say, uh, you're gonna simplify that issue. You're gonna try to make it as provocative or incendiary as possible, because these are the emotions that drive that kind of virality. And so the conflict of interest isn't in one stock. It isn't that they're writing about Google. It's that they want to slam Google or they want to praise Google because that's where the traffic is, and that's just as manipulative.

Let's talk a little bit about what you've done outside of of writing books, and I definitely want to get back to the Daily dec But I have to ask you about American Apparel. You're a young kid, you're like nineteen or twenty, you're just dropped out of college. How on earth do you get hired as the head of pr for them? Well, they're right in the middle of a sexual harassment scandal with their founder of Charney and all sorts of other things. They had a very salacious

advertising campaign. No one was really surprised by this. The timeline there is it's a it's a bit confusing, but uh, you know, I got hired as sort of a consultant. Early on, I was friends with someone who's on the board of directors, the author Robert Greene, And I come in as a consultant. Then I started cleaning stuff up, organizing. Uh, you know, the way the marketing efforts are done. There was no marketing department. I put one together and then

I'm in charge of that. And then, you know, one publicity scandal after another. Uh it was it was an exhausting,

chaotic company, I'll put it that way. But it was also sort of a crash course, both not in not just in corporate pr and strategy and all these things, but also in just seeing how these scandals are reported by the media, where there might be a lot of truth to to them, but that doesn't mean the reporting about them is necessarily accurate, right, And so there was and Cocker was a company that covered American appair all

the time. So I got to really see how that sausage was made and it made me, you know, not want to eat any So, so the company eventually files for bankruptcy. They went through reorganization. Uh, the founder of Charnie gets forced out. Uh. The company now has an old woman board of directors. So what was that place like to work in? Was it as insane as it appeared from the outside? Was that just an image? I

would say it was both less insane and more insane. Right, it wasn't the Playboy Mansion, but it was chaotic and dysfunctional and and and oftentimes sort of startups that are still run by the person who found them are are that way, right. Uh, oftentimes the genius of the creator is also their biggest weakness. But I think that's a good way to encapsulate what was what was wrong at American Apparel. So you effectively get a crash course in the art of manipulating the media. How on earth did

did you find your way to that? And did you successfully help keep the company alive for long enough so that they could go through this re or bankruptcy. Well, it's a it's a really sad story in the sense that it was a company once worth a billion dollars and it was a great idea. Hey, sweatshop free apparel. Yeah, it was brilliant. I mean we sold millions, hundreds of millions of garments. We had twelve thousand employees, we had

stores in twenty countries. To me, it's evident. You can have the best idea in the world, you can totally resonate with your company, with your customers. But if you don't manage yourself, well, if you're not disciplined and organized, you don't bring in that adult supervision doesn't matter. Execution is everything. Yeah, and so it sort of tore itself apart both with scandals. But uh, you know, companies can survive scandals. What they can't survive as bad management. And

I think that's ultimately what happened there. So you write a book after this cold trust me I'm lying? Yea, which in I love the title. So are you lying? Why should people trust you? You? You raise the question yourself, Yeah, trust me I'm lying. Is the liar's paradox. If someone tells you the lying, can you believe them? Uh? And my answer to that is, you know, if I was intending to manipulate people, I probably wouldn't write a book where I gave away exactly how all this works. You know,

that's first thinking. Second level thinking is, oh, I'm going to show them so nobody really believes this. The idea for I thought I was look, I I sort of had grown disillusioned and disgusted with how all this worked. And I had this sort of premonition that some manipulating the media to sell T shirts is not the world's worst sin, right, but I had this sense that the same things could be done for much more ominous ends.

That's really why I wrote the book, and I think that's ultimately why it resonated, why it's taught in all these journalism schools. Uh And And the sad part was that people who really needed to listen to it didn't listen to it, and they didn't wake up to the sort of uh, you know, the the exposure there until basically after Donald Trump was elected and and then they said, oh wait, this is real serious, there's real cost to this. So I can tell if this Times review is a

compliment or a slight quote. He is like a snake oil salesman who swears he is abandoned the snake oil, but not the highly effective snake oil sales tactics. So how do you respond to something like that? First of all, is that a compliment or is that a a dig

on you? Well, that's sort of your typical Times sort of looking down their nose at you and and uh, overall, that article was not a bad piece of pr No, But you know, profiles are filled with these sort of subtle digs get you too, that that you walk away thinking that obviously the writer is period to the person that they're writing about, and there's a little bit of that in the piece, which the territory. That's the nature of all criticism and reviews. Yeah, right, you you can't.

You don't outwardly attack them. You undermine them with the anecdotal details. Right, Um, But I think, uh, I I don't. I don't think it's snake oil tactics. I mean the the you write a book, you have an idea, you have something you have to get out in the world. If you don't sell it, how will anyone ever find out about it? And I think that's how there. You know, you could say that the shelves grown under the weight of undiscovered, brilliant books. And I think what I bring

to my writing is stuff that resonates with people. The vast majority of mysels sales come from word of mouth. But I also know how to how to create a stir around that book when it comes out, and and to and to get a discussion going, which is what the job of an author is so conspiracy, you know

it's gonna sell itself. Given the content, the details, and a lot of the never before discover details the daily stoic about a two thousand year old philosophy, I have to pivot and ask you a what motivated you to write this? And be how does such a what sounds like a dry I mean I found the book because in college I studied a lot of philosophy and I'm fascinated by a ton of people from Marcus Royalist, go down the list. So this was one of those things.

It's like, oh, that's a surprising title. Let's let's try that. How did this become such a fireball in Silicon Valley? Well, you know, I fell in love a stoicism when I was in college. It was it was it was like, oh, wait, this is how you're supposed to live right And and I would say it was very helpful amidst the chaos of American apparel, not wanting to get implicated in it

and sucked into it. So so layout for for people who may not be philosophy majors lay out the details in a few bullet points of what Stoicism is about what's a philosophy of sort of inner strength and discipline. It holds that sort of virtue and and and constancy

or the highest goods. And then I think my sort of definition to it to lay people is like a stoic says, you don't control the world around you, but you always control how you respond, and you got to respond well, and that you you see everything good and bad as this sort of opportunity for that response. Right. You can't make it stop raining, but you can remember to bring an umbrella. Is really the oversimplified version. Yeah, that which people, by the way, you find hard to

grasp sometimes. Right, And and you know, most of what was happening that American apparel was outside my control, but I did control, you know, the direction of my own career, the direction of my own life, the decisions I was going to make personally right, and what I was going to learn from what was happening and all these things. Did the residents in Silicon Valley come as any sort of surprise to you? I mean that it really seemed

to have caught on there. The Silicon Valley residents surprised me a lot less than its residents in professional sports. I mean, there are dozens of major league franchises in every sport that are that read the Day the stock on a daily basis, of politicians that read it in the Senate dining room. It's been this very absurd, sort

of surreal experience. And so when people, you know, talk to me about my controversial books, it's it's always I sort of smile and laugh, because they've sold a fraction, uh of the copies that my serious books on silk philosophy have sold, and the impact, and none of those people care who I am, and those books have essentially marketed themselves. I'm one of those people who I had no idea you had authored this book until I started researching Conspiracy. And I'm like, wait a second, I have

not one, but two copies. I have one in the office and one at home. You're telling me the guy

who wrote Conspiracy wrote this all right? Now, I'm intrigued by this person as an author, because these two books could not be further apart in terms of subject matter, and and Peter Thield could have used a little stoicism in his life, and certainly Nick Detton, actually Nick Detton is a fan of the Daily Stoic as well, and that's one of the things we can because that's that's what you turned to when you're forced into personal bankruptcy by a secret vendetta from a person you didn't even

know you'd upset, right, Um, but but you know it's it's weird too. And I remember talking about it with that New York Times reporter you're mentioning, you know, I was saying, like, look, I'm a good marketer. I can sell anything. Why would I have chosen a two thousand year old philosophy that that has the sort of stereo

emotionless uh dry, uh without joy? Why would I have chosen stoicism unless that's what I'm actually interested in, Unless I really felt like it could make a difference if if if I was financially motivated, I'd be working in cryptocurrencies or you know that there's any something a little hotter than than stoicism, right right, And and and it really is something that has been deeply impactful in my life, that's helped me through my own sort of difficult circumstances,

and and and something I I felt like was worthy of, you know, sort of making my my life's work. And is it true you read the meditations four times in a row as a college student or is that just it would have been? I mean four times in a row is probably an understand I probably read that book. You really? Yeah? Wow, that's that's fascinating. We have been speaking to Ryan Holiday, author most recently of Conspiracy and

previously of The Daily Stoic. If you enjoy these conversations, be sure and check out the podcast extras, where we keep the tape rolling and continue to discuss all things conspiracy related. You can find that at iTunes, Overcast, Bloomberg, SoundCloud, wherever your finer podcasts are sold. We love your comments, feedback and suggestions right to us at m IB podcast at Bloomberg dot net. Check out my daily column on Bloomberg View dot com. You could follow me on Twitter

at rid Holts. I'm Barry Ridholts. You're listening to the Master's in Business on Bloomberg Radio. Welcome to the podcast. Ryan, Thank you so much for doing this this you know a little inside baseball. Um. I prepare these daily reads for Bloomberg every day, and as I'm and always, as soon as I hit send, twenty minutes later, I find something interesting and I find Derrick Thompson of the Atlantic, who wrote the book. Um, I want to say hit Makers, right,

who was previous? Yeah, wonderful, he's the previous guest of the show. I find his conversation with you and I'm like, oh my god, this is so much more interesting than I ever expected conspiracy to be. There's so many questions we didn't get to. I have to give you a few quotes of yours and have you push back them. Blogging is a digital blood sport. Explained Well, it's not just uh, this sort of battle inside a company for clicks, right,

Who who's the best writer, Who's getting the best scoops? Uh, it's it's this juror. It's this intense battle between journalists and all these different outlets. You gotta be first, you gotta you gotta brand your story the best, you gotta have the best headline. All these news sources are competing with each other for a finite amount of attention. So it's a blood sport that way. But then also we could say we take a as a as the view

in public. We take a great deal of pleasure and watching people it particularly well known people get torn apart. So it's this blood sport I think in both directions. Isn't the history of that sort of tabloid journalism and that really gossipy celebrity rag type of approach to media. Hasn't that been around for forever? Yeah? I think Oscar Wilde said, we used to have the rack and now we have the press. That's how we used to torture people, and now we do it. Uh you know, now we

do it digitally. Um. So, So I think it's just an an escalation or a growth in a trend that's always been there. Another quote, and this one was from trust Me on lying my job was so easy that it scared me. Yes, and you're obviously referring to the media and your ability to manage the coverage they were doing. Explain why it scared you. I'll give you an example. When I was putting out and trust Me, I'm lying. Um, I thought, what can I do that sort of proves

this book right? And so I I put out a press release where I announced the size of the advance, which I doubled. Uh wait, so let me. Let's so you claimed the two fifty advance. Now I claimed that to fifty advance was a five dred thousand dollar advance because nobody fact checks press releases. So so it was a two fifty you claimed five hundred, and people bought it, immediately picked up. No One became tremendous amount of buzz about where is this who is this person? How do

you just get a half a million? And he said, hey, this guy is writing a book about lying to the press. Maybe we should fact check what he saying. Yeah, nobody said, let's call the publisher and get the size of the advance. Right, So that's the first thing, and then us So it starts to get picked up. And then I I send an anonymous tip to Gawker, a writer named Hamilton Nolan, and I say, how could this person have gotten a half a million dollar book deal? It must be a

celebrity tell All about his clients. And you just basically read me. He sends me an email. Uh, and I say, I can't answer this, no comment right, and uh manufactured buzz Right. Five minutes later, you know, is Ryan Holliday's new book A Celebrity Tell All? You know Boom, that story to this to this day has not been corrected.

And this is the same website that you know would attack me for writing this book or that would say that, you know, Peter Thiel destroyed a venerable institution of journalism in his in his lot, and it's like, actually, no, this was in many cases a rumor mill, right, a clearinghouse for rumors and gossip up in poorly fact checked information. And and we this revisionist history does not quite encapsulate how the system actually works. And so my point is, look, I did that as a joke for a book to

prove a point. But what could I do if I wanted to propagate some racist theory or if you had a more nefarious intense Exactly? Wow, that that is just astonishing. Who was the media editor at The Observer when you were there? Uh? Well, Ken Kerson was the editor in chief. That's who edited my columns. The one thing I didn't get to about conspiracy earlier was U M b TA. That was Peter Thiel's acronym, Yeah for for Gawker tell us about they called his acronym stands for Manhattan based

terrorist organization. And that's that's what he believes. This is not just a hey, I'm annoyed that they did this. He's really looking at them as a very significant um problem for or anybody who's potentially in the public eye. Yeah, and I think he deeply believed that, right or wrong, But it is the predilection of anyone in a feud or in a conflict. You label your opponent as evil and it allows you to justify the lengths to which you're going to demonize them, and they're no longer a person.

So we we have the Hulk Hogan sex tape. That wasn't the only sex tape, didn't um was it Fred Durst of Limp Biscuit. And they run a number of sex tapes and what was so and and leaked celebrity photos. They've done a number of things. And what was actually so remarkable of the act actress cell phones with all the nude selfies on them. What I mean that was that was in the press for like six months, a different one every day. What was so remarkable was that

no one had actually taken doctor to trial before. And that was Tell's insight, right, He felt like, no, not only did most people not have the money, but most people didn't have the determination or the stamina to take it that far. And so there's this remarkable moment in the trial that I talked about her pre trial where in the depositions, you know, the first question you're asked that a deposition is have you ever been deposed before?

And the answer from the folks at Gawker's universally no, all the most controversial media outlet on the planet that had been never sued, and so they were in uncharted territory. They didn't know how dangerous the predicament they were in actually was. Because would you like writing this book? I could tell you really loved writing Daily Stoic. You could see this is a very personal book for you. Yes,

this one. I get the sense that you may empathize more with some parties and others, but this felt like there was a little bit of an arms length distance. Am I am I overstating that? No? No, I would say Conspiracy was harder to write, and I enjoyed it

as the artistic challenge that it was. I would say it's not personally fulfilling the way that writing the obstacles away and he goes the enemy, and and and the Daily stock have been from me because they've challenged this book challenged me as a person, no question, but they challenged me as the person I want to be in everyday life. They challenge challenges me to be better and ask tough questions. This was this was much more challenge

as a as a creative person. So in response to to what you're saying philosophically, do you find, given your history with places like American Apparel, does that interfere with the way people perceive you? And and as a stoic

does it matter? What matters is your response to them? Right? Well, I look, if I if I was writing my own life story for the purposes of getting credibility of total strangers, of course my experience with controversial clients is not what I would put in there, right, And those are mistakes, are not mistakes, So those are choices that I live with and have learned from. Uh huh. But you are very you know, I mean to be fair to you.

You are twenty at American Apparel. At twenty, I was, you know, going to Kegger's in college and getting high all the time. I can imagine having a real job at that age. Yeah, And and there are things I would do differently, uh if it made me who I am. But there are things I would do differently. But I think, you know, historically it's a strange argument, right, because Seneca is Nero's tutor, So I think anything on the right side of that, it's pretty safe, do you know what

I'm saying? Like he was the advisor to the worst emperor in history, a deranged psychopath, and he still felt that was consistent with stoicism. So I feel like it's pretty respect if you you weren't advising the person who led to the full of realmes for you. Um, let's get to some of my favorite questions, the standard things I ask all of my guests. And this is a tough question to ask you because I don't know if there's the answer to this. What's the most important thing

people don't know about you? That's a good question. I mean, I think people tend to think I'm not a person, right, Like I'm either the sort of machine that turns out books or that I've worked for these controversial clients, so I must be this horrible person, and you know, I'm just a normal person who writes books. Pretty reasonable. I try. I try to be That's that. I would like to be a successful normal person. That's my goal. Good, good girl. Tell us about some of your early mentors who who

uh sure affected who you are and your philosophy. Well, you know, one of the most trying things in American apparel watching this company collapse and implode, is that Dove Charney was this great friend of mine, this person who had seen talent and promising me, who would groom to me, wo had given me many opportunities. It's very alarming when someone who says I see some of myself and you

catastrophically implodes, right, and you start to question things. But you know, Robert Green, the writer uh the forty forty A Laws of Power and Mastery, I was his apprentice on the side as all this is going on, I'm also a research assistant to Robert Green, and and that was my sort of crash course in how to be a writer? And and he's like sort of the model for how I try to live my life. Not I don't try to live my life by the forty Laws

of Power. I try to live my life the way that the author of the forty at Laws of Power, who is this sort of disciplined, kind, generous person, happens to live his life in the profession that I'm also in How did you find your Way? To Robert Green? He's such a fascinating character. I was an enormous fan, and I was working for a different author who happened to know Robert, and I just wouldn't would Yeah, huh, that's interesting. So who else influenced your approach to media

to media? Well, one of the books I would suggest everyone read who Who's looking to sort of understand media as a book by Upton Sinclair called The Brass Check actually the name of my marketing company as well. But he writes this book after the Jungle. He writes an expose of journalism in the in the early twentieth century, and it's just as disgusting as the meat packing industry. And it's you could replace You could take the exact same book, replace newspaper with blog and it would be

equally true today. So funny you say that there's this book from the early twenties something I'm trying to remember the name of the author, how trade stocks, And you could replace any of the dot coms with any of the telegraph companies and everything is exactly the same. It's it's amazing you said that's name exactly. Well, that's what the Stokes say, is that history is just this constant repetition of the same people doing the same Human nature

is unchanging. It's it's no surprise. So you mentioned, um that book. Tell us about some of your favorite books. That's ah that It's always hard to give general book recommendation. By the way, this is the one question I get more emails about what was the book that he recommended more than any single thing. People want good recommendation. So it doesn't have to be general, or it could be general or specific. It's what books do you think are important to you and if people enjoy it or not,

that's on them. So I'll give you a couple. So one I would say everyone should read Robert Green forty Laws of Power and Mastery, incredibly important books. I'm a big Rich Cohen fan. Uh. He wrote Tough Jews. He wrote The Fish That Ate the Whale about Annuals of Murray, the founder of United Fruit. One of my favorite books of all time, The Well, Yeah, it's a it's an incredible story of of of financial operations and entrepreneurism. Uh. And and you know government and Rich Cohen as I'm

a huge fan of Rich Cohen. Um, I'm a big William to come to Sherman fan. He's one of my favorite I love Sherman and Grant, so I both of their memoirs. I would strongly urge people have I've read so many biographies of Grant that I feel guilty about reading another thousand page But I love churn out. His book on Rockefeller's fantastics. I think his book on Andrew Hamilton's is as good as you would expect. His book on Washington is fantastic. I'm a big biography fan. I

think biography is how we learned. And then I would say Plutarch's Lives. Uh, there's a reason that almost every great historical figure is either in that book or obsessed with that book. Um, and then of course the Stoics. If you the most powerful a man in the world, Marcus Currelius sat down every night and wrote in a journal notes to himself about how to be a better person, and that survives to us. Yeah, you would be an

idiot not to read that book. I mean, it's just an incredible years old and it just persists ongoing exactly that that is for someone said, I don't know if I have any books. That's a nice list of books. What excites you right now? What are you looking out at and saying that's really interesting. I mean, I do think cryptocurrencies are interesting that I think someone will solve

someone will find a practical use for blockchain. Uh And and I think it's a race to find there is the speculative bubble of cryptocurrency to separate things, the technology and the trading there, and someone will solve it. And I think that will be really interesting. So I'm interested in that. You know, I live in Austin. I live on a small farm. I think I was just reading this article. Elon Musk's brother was saying he thinks millennials

will move to farms. He thinks that they will flee the city, not to the suburbs, but to keep going the land. And uh that mac that that lines up with my experience. And and I'm bolish on that. Although cities continue to attract young people and ever greater numbers, especially now that jobs have become fairly plentiful. Yes, but I think, like if my own career is somewhat ahead of the curve because I started early and got lucky

in many ways. It's that you go to the city, you make your money, you build a business, a reputation, and then you can work from wherever you want. And then you go, why am I living in New York City? And so I think that I think it will be interesting to see how millennials chade. Our millennials going to move into the suburbs, back into the suburbs they grew up in, or they're gonna piety or their own thing. Right.

The answer to the question is the food is while you live here, you can't get good Chinese food on a farm or if that's not yes, if that's if that's or Vietnamese food or or go down the list, pick your favorite cuisine. Um. But at a certain point it's hard living in a city versus having little elbow space and a big sky. That's a very different lifestyle that that I think suits you once you work through your twenties and theories hy hypothetically, Um, So we've been

talking a lot about the media. What do you think the next set of changes are that's gonna wash over the media landscape. I think we're going to see more and more subscription based content, especially as millennials get older and their time is worth more money. Uh. The idea like the reason people pay for Bloomberg terminals is because those the time and the information is extremely valuable to those people, right, and uh, you know millennials originally pirate

and music. We were never downloading anything, and now we pay monthly for Spotify, right because our time gets more, or Amazon Prime or Apple iTunes are going down the list you have. It's a there's a wealth of of everything. I'm not I don't know if you've discovered this, but I grew up in an era where you would actually get videotapes or DVDs. That's done. Everything we watch on video is either Amazon Prime, Netflix, Hulu going out in

the list. Nobody is buying this sort of physical stuff anymore. Yes, but I I do think you're going to see in the information space people realizing that free information is very expensive. Free information it's worth what it costs you, Especially so the Washington Post behind a paywall, The New York Times, the Wollster Journal has always been beyond the pay and they haven't. I was just reading about their technology. Yeah, how much should we charge you? How likely are you

to pay? And I think that technology is only going to get better, like they do with selling airline seats. In other words, that's quite that's quite interesting tell us about a time you failed and what you learned from the experience. That that's always the tough question. I feel like I've been lucky in a lot of ways. Uh My, my failures have been slips rather than falls for the

most part. And so in some ways, you know, the stoic exercises to think constantly about the next like to to be prepared for some big setback, some big correction. So I do think about that a lot. But uh, you know, when I was building my marketing company, I'm I was. It was going well, and then I decided I really wanted to scale it and build it in

a in a big way. And you know, I took on some partners and some investments and investor money and hired a bunch of people and and and I remember my wife saying like, why are you have the perfect thing? Why are you doing this? And I didn't listen to her, which is always a mistake, and it went horribly wrong. It sort of blew up my relationships with a bunch of people. I ended up being miserable. It was it

was working way more and making probably less money. Um, and so it was it was a good failure for me. And that sometimes you've got to figure out what you don't want to clarify what it is that you actually do want. That makes that makes perfect sense. Um, tell us what you do for fun? Uh? You write an awful lot. What do you you to just relax? I would say when I'm not writing, that's what I'm having

the least amount of fun. Like, I don't have a book that I'm in the middle of right now, And it's weird, right I'm like, how do I fill all this time? Like it's that's that's where I dedicate a lot of my energy. Uh, but you know, I I'm a big I run and swim every day. Those are my like two that's my two favorite parts of the day. Or if I'm doing both, that's my favorite thing to do. And the new iPod has a waterproof feature. You can actually listen to music in the pool. I reject that entirely.

I think the pool is the I say the pool is the last quiet place on Earth, no screens, no noise. It's I love swimming precisely because it's one hour of nothing. You're in the pool for a solid hour and try I try forty five minutes to an hour. I tried

to do. I'm impressed. If a millennial or a budding writer were to come to you and ask for a career advice, what would you tell them, Well, I'd give the writer the advice that that I got, which is that you have to go do interesting things, right, don't go learn how to write, well, go learn things about the world that you can then communicate in the writing.

So when you were asking me about some of my controversial choices career wise, or things I've got myself in trouble with or whatever, on the one hand, you know, those might not be great for my brand, but they've also been the few I wouldn't have written my first book done that, and it's given me a perspective at an angle and a you know, material, and so a writer needs material more than they need anyone can write

like you know. I'd read Keith Richard's biography. It was written in cran you know, and was filled with misspellings because he's lived an incredible life, right, And so a writer has to go have experiences that fuel their writing. That's quite fascinating. And our final question, what is it that you know about the world of media and literature today that you wish you knew ten fifteen years ago

when you were first getting started. The incentives make it almost impossible for it to have the traits that we want to have, right We we want media to be empathetic and truthful and reasoned and balanced and fair and all the all the things you would explain, You're like, I'm describing what I would want to see in the ideal media outlet are essentially economically impossible, right there an economically impossible, and then worse, there's a culture on top

of it that that that exacerbates it, uh, rather than corrects or mitigates it. Are you referring to digital, prince, electronic, all the above? I would say all of the above. Like, I'm biased, but I think books are one of the few safer mediums right because you pay for books, they take a long time to make their design to last for a long time. So the only mediums I'm I'm I'm a fan of right now are books and podcasts.

Quite quite fascinating. We have been speaking to Ryan Holliday, author of the book Conspiracy, Peter Teel, Hulk Hogan, Glocker and The Anonomy of Intrigue, as well as several other books including the Daily Stoic. If you enjoy this conversation, be sure and look up an inch or down an inch, and you could see any of the other, let's call it hundred and eighties seven such prior conversations that we've had. We love your comments, feedback and suggestions right to us

at m IB podcast at Bloomberg dot net. I would be remiss if I did not thank my crack staff for helping to put together this podcast each week. Medina Parwana is our producer. Slash audio engineer. Taylor Riggs is our booker Slash producer. Michael bat Nick is our head of research. I'm Barry rid Hults. You've been listening to Masters in Business on Bloomberg Radio.