Transcript: Ryan Holiday



The transcript from this week’s MIB: Ryan Holiday is below.

You can stream/download the full conversation, including the podcast extras on iTunesBloombergOvercast, and Soundcloud. Our earlier podcasts can all be found on iTunesSoundcloudOvercast and Bloomberg.


ANNOUNCER: This is Masters in Business with Barry Ritholtz on Bloomberg Radio.

BARRY RITHOLTZ, HOST: This week on the podcast, I have a very interesting and not quite as controversial as his reputation makes out. Ryan Holiday is the author of really a very fascinating book about the entire Hulk Hogan, Peter Thiel, Gawker litigation called “Conspiracy.” He has really a fascinating amazing background. I wish I had another hour because I had so many more questions.

I’m a big fan of Robert Green. He was a research assistant for him who wrote the books on power laws. I didn’t get a chance to talk about that. But we really delved into what’s going on with the media, the whole problem with digital marketing, blogging, all of the sort of click-happy social media, the filter bubbles that have been created by Facebook, and Google, and Twitter.

It really is an interesting question. He has quite an amazing story, drops out of school, very young, eventually gets a gig in American Apparel. I think he’s 20 when he becomes their Head of P.R., 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 bestsellers. 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 Ritholtz. 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 P.R. for American Apparel. He is a media strategist and columnist and the former Editor at Large for the New York Observer. At the young age of barely 30, 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 Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue.”

Ryan Holiday, welcome to Bloomberg.


RITHOLTZ: 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 a inside look at the Gawker trial, which we learned was backed by Peter Thiel. This is so different than everything else you’ve written. What attracted you to this — this subject matter?

HOLIDAY: I have the same reaction to the story. I mean, it — it feels like it’s something that should have happened in the 19th century. It’s what a — it’s what Vanderbilt or Rockefeller or Carnegie would have done to an enemy. The idea of this billionaire having this personal grudge for good reasons or bad reasons against the media outlet, and then plotting secretly in the shadows to — to destroy them sounds epic.

In fact, it’s not even the 19th century, it’s Shakespeare or Plutarch —


HOLIDAY: — or something.

RITHOLTZ: The Spanish-American War, yellow journalism, all that sort of behind-the-scenes manipulation.


RITHOLTZ: The — the most fascinating thing is you had written a couple of columns on Gawker and Thiel for the Observer.


RITHOLTZ: After this whole thing goes down, both Nick Denton —


RITHOLTZ: — the founder of Gawker and Peter Thiel separately unaware of the other reach out to you to tell their side of the story. What — what was that like?

HOLIDAY: It — it was surreal. I mean, there was one night at the end of 2016 where I had dinner at Peter Thiel’s house, and then the next night I had — I went to an event at — at Denton’s house. And I — it struck me that I was probably the only person speaking to these two mortal enemies, these two people who had spent north of $20 million fighting each other, that embarrassed each other in the press.

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 so —

RITHOLTZ: And to bring everybody up to speed, Thiel wins the giant case or I should say Hulk Hogan in — in the guise of his real-life persona —


RITHOLTZ: — wins $100 million plus litigation. It’s bank — it’s bankrolled by Peter Thiel. It ultimately bankrupts Gawker —


RITHOLTZ: — and forces Nick Denton, the founder and — and sole owner or majority owner of — of Gawker —


RITHOLTZ: — into personal bankruptcy. So these aren’t people just having a — a Twitter battle —


RITHOLTZ: — these are really people at each other’s throats.

HOLIDAY: No, I mean, this is an epic conflict. It begins in 2007 when at — at Nick’s prompting Gawker out, Thiel is gay. He — he —

RITHOLTZ: So back up a sec. So, Gawker Properties owns Valleywag —


RITHOLTZ: — which was the —

HOLIDAY: They’re sort of.

RITHOLTZ: — tally version of a gossip. So —


RITHOLTZ: — Gawker started it sort of like a — a Page Six with no limitations, a high hitting, hard —


RITHOLTZ: — hitting —

HOLIDAY: And the way that you would need to be a celebrity to be on — to be on TMZ or Page Six, Gawker 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 —

RITHOLTZ: So — so 2007, what was the title of the post that had come out in Valleywag.

HOLIDAY: It was “Peter Thiel is totally gay, people.” And I think that in — one — there’s an early Gawker memo that said every post should have a glint of meanness, nastiness, right.

RITHOLTZ: Yeah, I read that.

HOLIDAY: And I think that —

RITHOLTZ: I read that in your book.

HOLIDAY: — that — that headline perfectly encapsulates that it’s — it’s not just that you’re taking a — a relatively private figure, someone who is certainly a well-known investor but just because you’re an investor doesn’t mean people —


HOLIDAY: — get to know who you have sex with or not.


HOLIDAY: And — and —

RITHOLTZ: But it 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 Thiel was gay.

HOLIDAY: Yeah, that — that — that’s what they claimed. I think Peter would say, you know, my parents knew, my close colleagues knew, the people I went to college would knew 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?

RITHOLTZ: Is — isn’t that sort of an odd distinction — because if someone outs 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 —


RITHOLTZ: — 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 going to take this and spread it around a little bit, and put a little Gawker stink on it.”

HOLIDAY: Well, let’s say that you and your wife have an open marriage. Obviously, some people would know by definition of it being open.

RITHOLTZ: Have — have you heard anything?

HOLIDAY: Yeah. But —

RITHOLTZ: What am I not — what am I missing?

HOLIDAY: — let’s say — let’s say I had heard something —


HOLIDAY: — does that mean at what point do you become a fully public figure the way a president —


HOLIDAY: — or a celebrity or a rock star as 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 to some respects — in some respects, it doesn’t actually matter whether he should have been outed or not. What mattered is that he felt that it was a grave violation, right? It’s like it doesn’t matter if the Count of Monte Cristo actually was wrong, what matters is that he is stewing in prison about it.

RITHOLTZ: So let’s ask the question, is Peter Thiel thin-skinned? 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 slate that warranted this sort of — because it seems like someone shot him with a pea shooter —


RITHOLTZ: — and he took a bazooka and fired back.

HOLIDAY: Well, we got to go back into time a little bit and think about, you know, in 2007, Obama hasn’t even come out in favor —


HOLIDAY: — of gay marriage, so it is a different issue at that line.


HOLIDAY: And I — I think he had his own complicated relationship with his own sexuality. He’s a — he’s a — he’s conservative, 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 a glint of meanness that says the things that other people can’t say, right, that — that — that sort of attacks, publishes first and verifies second. And — and you got to remember, he doesn’t really actively begin to plot against Gawker until probably around 2011, so it’s really this thing that’s just sort of bouncing around in his head and he’s —

RITHOLTZ: Just dating for four years.

HOLIDAY: He’s a — he’s seeing things they’re writing about other people. He’s seeing them write about his businesses, he’s seeing them write about complete strangers who did nothing wrong. And it’s —

RITHOLTZ: (Inaudible).

HOLIDAY: — as you said, it’s just — it’s just — 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.

RITHOLTZ: Let’s talk a little bit about the person who planted the seed in the mind of Peter that there was an opportunity to seek his revenge against Nick Denton and Gawker 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?

HOLIDAY: So in April of 2011, 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 he’s going to place at his start-ups.

The PayPal mafia, which we now see as sort of the — one of the most powerful networks of investors probably in history originates because of this habit from Thiel. And so he — he meets with — with this young man. I refer to him as Mr. A. I — I know the identity of the source, but my agreement with the source is that I — I wouldn’t — I wouldn’t unmask him.

But they meet and they’re talking about Gawker and — and Thiel’s complaining and 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 Thiel in the eye. It’s remarkable that he would have the — the stones to do this —


HOLIDAY: — 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.


HOLIDAY: And then he goes into this pitch. He says, “Look, I think — I think buried within Gawker archives is a number of posts that would be a violation of some law — civil or — or — or criminal in one way or another. I think if you — if you put up the money, 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 into you is not illegal or at least it’s on the line, but they may have got way over the line in other cases. And so that Peter agrees in this meeting to — to budget $10 million on this completely insane project that ultimately culminates in $140 million judgment in Gawker bankruptcy.

RITHOLTZ: So — so good ROI on that investment —


RITHOLTZ: — at least from a venture capital perspective.

And at the time, just to put $10 million, which sounds like a lot of money —


RITHOLTZ: — into perspective, he’s worth — he’s one of the early investors in Facebook.


RITHOLTZ: He’s been extremely successful as a V.C. not just PayPal, but Facebook and — and go now on a long list of —


RITHOLTZ: — successful investments, I believe, at the time, Facebook was about $1 billion holding for him. I don’t know if he was still holding all of it but —

HOLIDAY: Yes, Facebook is going to IPO about one year later, and he’s going to own 10 percent of it at the IPO.

RITHOLTZ: That’s unbelievable.

HOLIDAY: So, this is a fraction of his net worth. This is, you know, chump change, but it is also objectively way more money than anyone has ever spent on something like this before.

RITHOLTZ: The — the assumption is, hey, if you had $10 million to burn through —


RITHOLTZ: — could you find a more productive usage for it or is it just simply self-indulgent revenge?

HOLIDAY: Well, that is — that is the question. But Peter has come to say that he believes this is the most philanthropic thing he’s ever done. His point was he believes that we sort of accepted this idea of technological determinants, right? Blogging is invented. Gawker is an outgrowth of that — of that technology. And then we’re, as a society, just sort of a slave to whatever this thing does, right?

RITHOLTZ: Of course your recruiter much less genteel because of no holds barred.

HOLIDAY: And you could argue we have the same attitude towards our cell phones, towards Facebook, towards Twitter —


HOLIDAY: — like, oh, this is what it is, right? It was invented. And — and Peter — Peter sort of rejected that idea. 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 on corridor (ph) 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 —


HOLIDAY: — and — and sort of revenge-based, right? It’s — it’s this complicated mix of motivation.

RITHOLTZ: And — and we should never underestimate the ability of — of ideologues to rationalize any behavior in furtherance of the clause,

HOLIDAY: Well — and probably never underestimate the ability of extremely wealthy people to rationalize whatever their preference is as being part of the greater good.

RITHOLTZ: 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 0.1 percent and 0.001 percent with kid gloves? Isn’t this a — a direct contradiction of the First Amendment and a robust free press in a democracy?

HOLIDAY: 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 lawyer that they — they hire to litigate these cases, they are specifically looking for cases that are not libel and defamation, they are looking for copyright violations, violations of — of federal trade laws, violations of, you know, individual privacy.

And so the reason they end up suing Gawker in Florida is — is that they’re running a sex tape of a — of an individual is — is of a very sort of specific violation there that they can ultimately be held accountable for.

RITHOLTZ: So they picked Florida because of the state laws. Was — was anybody related in Florida? Anybody —

HOLIDAY: Well, Hogan lives there and that’s what Terry has reported.

RITHOLTZ: Now, what is his — his —

HOLIDAY: Terry Bollea.

RITHOLTZ: Terry Bollea. So one of things that strikes me about the book, and I — 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.

HOLIDAY: Thank you, thank you.

RITHOLTZ: Having only read “The Daily Stoic” previously, I was not expecting this. But one of 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 actor in some way, and yet it’s kind of a compelling narrative.

HOLIDAY: Well, I think it’s extremely compelling just — and — and almost unbelievable what actually happened. You know, there’s — these two Florida DJs and a professional wrestler and somehow Donald Trump ends up entering the story at the very end, right?

RITHOLTZ: How did the DJs not get tagged because they literally stole —

HOLIDAY: They did it, yeah.

RITHOLTZ: — private property and then released it. You would think the liability is on them as much as anybody.

HOLIDAY: Well, I mean, one of the weird arguments and this is where it gets so sort of conspiracy theory ask is that the FBI investigates the — the person who stole the tape, and the lawyer who is brokering the tape decide — declines to prosecute despite having overwhelming evidence. And then that lawyer is the same one who now represents those two porn stars who are accused of — of brokering secret deals with Donald Trump in the — in the — at the end of the 2016 campaign, so the whole story is insane.

But I think part of the — the sordid mess 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 reason — one of the reasons I wanted to write the 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 is 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 and 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 personally, you know, reviewing legal briefs in the —


HOLIDAY: — in the case, 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 — a sign of what’s to come now that Silicon Valley is, in some ways, the — the power center of the entire planet.

RITHOLTZ: 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 led to very sensational coverage. Tell us about how Mr. A came about in your — your understanding of — of how this whole affair unrolled.

HOLIDAY: I remember I was first interviewing Peter, and he mentioned — 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’s someone other than you involved in this? This is unbelievable.”

RITHOLTZ: Nobody had reported about it, nobody had said —


RITHOLTZ: — not until after the book came out. I think BuzzFeed out (ph) and Mr. A, and I know I know you’re not allowed to confirm or deny.


RITHOLTZ: But if you Google the book and BuzzFeed you could gets at least one person’s best guess.

HOLIDAY: Right. And — and — and that story only breaks because my — the pending 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 — the role — the role entirely.

RITHOLTZ: It’s the whole episode.

HOLIDAY: And, in fact, that was what allowed the conspiracy to be so successful is that there was a — you know, three levels or three layers removed between Peter and Hulk Hogan and — and that was able to separate these things.

You know, I think Peter said to me one time when I was asking him, he said, “You know, I think what was so incredible to me is 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 it.”

RITHOLTZ: Was — wasn’t even looking for it.

HOLIDAY: And — 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. He said they’re not thinking about it at all.

RITHOLTZ: That’s fascinating.

HOLIDAY: 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 he’s so focused on, you know, what this means for their business rather than communicating facts to the public, you know, 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 — 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.

RITHOLTZ: So let’s talk a little about your background and how you ended up becoming this media scourge. You dropped out of college to take a job at a Hollywood talent agency. That sounds like a risky plan. What — what were you thinking at the time?

HOLIDAY: Well, that was the question my parents, of course, asked at the time. I — I felt like this — you know, this was 2007 sort of media in this media, and — and technology, and culture is 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 happen to end up working for a number of really controversial clients. I think it sort of showed me, oh, 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 exposé 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.

RITHOLTZ: 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.

HOLIDAY: I — it came out in 2012.

RITHOLTZ: OK. So, six years ago, seven years ago fake news has become a presidential utterance all the time.


RITHOLTZ: Facebook, Google Search, Twitter, they’re all sorts of these accusations that not just the mainstream media, but the technology aspect of that completely dropped the ball on this. How has the entire media landscape changed society? And what does this mean for us in a democracy?

HOLIDAY: Well, you could almost argue they’re sort of an equivalent to the financial industry. And that — that, you know, the financial crisis, there have been a number of warnings, there are sort of the writing on the wall, there were these people who are pointing out problems. And it’s 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 had a similar situation in which the incentives were toxic and complicated. You know, the idea of paying people by the page view, the idea of — of sort of most news being filtered through the social networks where they have to either go viral, and if they’re not, then no one sees them.

These incentives were — were there. They were brewing and, you know, I wrote about it. Many other people were like, look, this is dangerous. Some — this is ripe for — and not only is this ripe with manipulation, it’s ripe for very serious manipulation.

And it 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 — the weak points, and they’ve hit them so many times that — that — that now we’re where we are, you know, whether it’s tens of thousands of fake accounts by Russian bots or whether it’s Donald Trump getting $2 billion worth of free publicity by sort of leveraging this constant controversy in 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 is a country governed by public opinion. So what governs public opinion governs the country. In — in the 19 — the early 1900s, what he said there was newspapers, but now it’s blogs and social media and — and — and this sort of online journalism.

RITHOLTZ: So let’s talk a lot about blogs. You — you wrote the business model for blogs encourages publishers and writers to value the click above other potential goals like truth, accuracy and fairness.


RITHOLTZ: So once that toothpaste is out of the tube, is there a way of putting it back or are we just stuck with this somewhat reckless, not quite mainstream form of — of media?

HOLIDAY: 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 sort of land rushing (ph) podcasts is because podcasts aren’t subject to those same toxic economics, right? A podcast —

RITHOLTZ: (Inaudible).

HOLIDAY: — 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 uphold it. That’s very different than the “Huffington 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.

RITHOLTZ: Right, I was going to call this Ryan Holiday’s sex tape escapade —


RITHOLTZ: — but you’re telling me that —


RITHOLTZ: — that’s two clicking and not — not what my listeners want to hear.

HOLIDAY: I imagine for the most part, the titles have very little impact on whether — the — the — the difference between your episodes —


HOLIDAY: — probably has more to do with the guest than —


HOLIDAY: — the provocative nature of the headline, right?

RITHOLTZ: A hundred percent.

HOLIDAY: It’s the — it’s the quality of the content.

RITHOLTZ: But that doesn’t exist in web or print-based media.

HOLIDAY: Well, I do think you’re starting to see some improvements with paywalls, for instance, like if you think about the — I — I read about this in “Trust Me Online” Tyler Cowen, the — the brilliant economist —

RITHOLTZ: He writes for Bloomberg?

HOLIDAY: Yeah, he’s — he’s the best. He was saying, you know, what are the — what’s the economics of a — of a paywall and said, OK, the first five articles are free. The first 10 articles are free. Everything else you have to pay. So now their incentive is to write at least 11 pay-worthy articles, right?


HOLIDAY: 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 half penny of advertising revenue each time, right?

RITHOLTZ: And some other kids at Gawkers and they were kids, were doing eight, 10 posts a day —


RITHOLTZ: — seven days a week. It sounded like a relentless grind.

HOLIDAY: I mean, it’s a digital sweatshop, in some ways.


HOLIDAY: And — and, you know, for instance…

RITHOLTZ: There’s the headline.

HOLIDAY: You would — you would never want a Bloomberg reporter to be writing about a stock that they own, right?


HOLIDAY: That would be a conflict of interest.

RITHOLTZ: For sure.

HOLIDAY: But what if the Bloomberg reporter is paid and this is how it was at Gawker, 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 going to — you’re not going to write a complicated nuanced piece without a strong conclusion, you’re going to say — you’re going to simplify that issue, you’re going to try to make it as provocative or incendiary as possible because these are the emotions that drive that kind of virility.

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.

RITHOLTZ: Let’s talk a little bit about what you’ve done outside of — of writing books. And I — I definitely want to get back to The Daily Stoic, but I have to ask you about American Apparel. You’re a young kid, you’re like 19 or 20, you —


RITHOLTZ: — just dropped out of college. How on earth do you get hired as the Head of P.R. for them while they’re right in the middle of a sexual harassment scandal with their founder Dov Charney and all sorts of other things? They had a very salacious advertising campaign. No one was really surprised by this.

HOLIDAY: The — the time line there, it’s a — it’s a bit confusing but, you know, I got hired as sort of a consultant early on. I was friends with someone is on the board of directors, the author Robert Greene. And I come in as a consultant, then I’d start cleaning stuff up, organizing, you know, the — 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, 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 and — not just in corporate P.R. 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 Gawker was a company that covered American Apparel all the time.

So I — I got to really see how that sausage was made, and it made me, you know, not want to eat any.

RITHOLTZ: So — so the company eventually files for bankruptcy. They went through reorganization. The founder, Dov Charney gets forced out. The company now has an all-woman board of directors. So what was that place like to work in? Was it as insane as it appeared from the outside or was that just an image?

HOLIDAY: I would say it was both less than sane and more than sane, right? It wasn’t —


HOLIDAY: — a playboy mansion —


HOLIDAY: — but it was chaotic and dysfunctional. And — and — and often times sort of start-ups that are still run by the person who found them —


HOLIDAY: — are — are that way, right? Oftentimes, the genius of the creator is also their biggest weakness.


HOLIDAY: And I think that’s a good way to encapsulate what was — what was wrong at American Apparel.

RITHOLTZ: 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 reorg bankruptcy?

HOLIDAY: Well, it’s a — it’s a really sad story in the sense that it was a company once worth $1 billion and it’s —

RITHOLTZ: And it was a great idea. Hey, sweatshop free apparel.

HOLIDAY: Yeah, it was brilliant. I mean, we sold millions — hundreds of millions of garments. We had 12,000 employees. We had stores in 20 countries.


HOLIDAY: To me, it’s evident you 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 —


HOLIDAY: — disciplined and organized, you don’t bring in that adult supervision —


HOLIDAY: — it doesn’t matter.

RITHOLTZ: Execution is everything.

HOLIDAY: Yeah. And — and so it sort of tore itself apart, both with scandals. But, you know, companies can survive scandals. What they can’t survive is bad management, and I think that’s ultimately what happened there.

RITHOLTZ: So you write a book after this called “Trust Me, I’m Lying.” —


RITHOLTZ: — which I love the title. So are you lying? Why should people trust you? You — you raised a question yourself.

HOLIDAY: Yeah, “Trust Me, I’m Lying” is the liar’s paradox. If someone tells you they’re lying, can you believe them?

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 —

RITHOLTZ: That’s first level thinking. Second level thinking is, oh, I’m going to show them so nobody really believes this.

HOLIDAY: The idea for — I thought I was — look, I — I sort of had grown disillusioned and disgusted with how all this work. And — and I had this sort of premonition that some — manipulating the media sell to t-shirts is not the world’s worst —


HOLIDAY: — 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 resonates, why it’s taught in all these journalism schools. And — and the sad part was the people who really needed to listen to it didn’t listen to it, and they didn’t wake up to this sort of, you know, the — the — the exposure there until basically after Donald Trump was elected. And — and they said, “Oh, wait, this is real serious. There’s real cost to this.”

RITHOLTZ: So I can’t tell if this Times review is a compliment or a slate, quote, “He is like a snake oil salesman who swears. He has 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?

HOLIDAY: Well, that’s your — your typical times sort of looking down their nose at you and — and —

RITHOLTZ: Overall, that article was not a bad piece of P.R.

HOLIDAY: No, but, you know, profiles are filled with these sort of subtle digs.


HOLIDAY: They’ll get you to — that — that you walk away thinking that obviously the writer is superior to the person that they’re writing about. And there’s a little bit of — of that in the piece, which is —


HOLIDAY: — with the territory.

RITHOLTZ: Right, that’s the nature of all criticism and reviews.

HOLIDAY: Yeah, right. You — you can’t — you don’t outwardly attack them, you undermine them with the anecdotal details, right?


HOLIDAY: But I — I think — 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 — that, you know, you can 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 my sales — sales come from word of mouth —


HOLIDAY: — 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.

RITHOLTZ: So, conspiracy, you know, it’s going to sell itself given the content, the details and a lot of the never before discovered details. The Daily Stoic, about a 2,000-year-old philosophy —


RITHOLTZ: — I have to pivot and ask you, A, what motivated you to write this? And B, 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 Aurelius go down the list.


RITHOLTZ: So, this was on those things, it’s like, oh, that’s a surprising title. Let’s — let’s try that. How did this become such a — a — a fireball in Silicon Valley?

HOLIDAY: Well, I — you know, I felt [the doses] when I was in college. It was — it was the — 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.

RITHOLTZ: So — so lay out for — for people who may not be philosophy majors, lay out the details in a few bullet points —


RITHOLTZ: — of what stoicism is about.

HOLIDAY: Well, the philosophy of sort of inner strength and discipline. It holds that sort of virtue and — and — and constancy are the highest goods. And then I think my — my sort of definition to — to lay people is like a stoic says you don’t control the world around you, but you always control how you respond.

RITHOLTZ: That’s right.

HOLIDAY: And you got to respond well and that you see everything good and bad as this sort of opportunity for that response.

RITHOLTZ: Right, you can’t make it stop raining but you can remember to bring an umbrella is really the over simplified version —

HOLIDAY: Yeah, that’s exactly —

RITHOLTZ: — which people, by the way, find hard to grab sometimes.

HOLIDAY: Right. And — and, you know, most of what was happening at 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.

RITHOLTZ: Did — did the residents in Silicon Valley come as any sort of surprise to you? I mean, it really seem to have caught on there?

HOLIDAY: 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 Daily Stoic on a daily basis. There’s 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, talked to me about my controversial books, it’s — it’s always — I sort of smile and laugh because they’ve sold a fraction of the copies that my serious books on stoic philosophy have sold and — and the impact. And none of those people care who I am, and those books have essentially marketed themselves.

RITHOLTZ: 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 Thiel could have used a little stoicism in his life —

HOLIDAY: And certainly Nick Denton actually —

RITHOLTZ: — as well.

HOLIDAY: — Nick Denton is a — is a fan of The Daily Stoic as well, and that’s one of the things we can lay over —

RITHOLTZ: (Inaudible).

HOLIDAY: — because that’s — that’s what you turn to when you’re forced into personal bankruptcy —


HOLIDAY: — by a secret vendetta from a person you didn’t even know you’d upset, right?

But — but, you know, it’s — it’s weird, too, I — and I remember talking about it with that New York Times reporter you were mentioning. You know, I — I was saying like, look, I’m a good marketer, I can sell anything. Why would I have chosen a 2,000-year-old philosophy —


HOLIDAY: — that — that has the sort of stereo — you know, a motionless, dry, 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.

I — if — if — if I was financially motivated, I’d be working in crypto currencies —


HOLIDAY: — or, you know, there’s any —

RITHOLTZ: Something a little hotter than — that stoicism.

HOLIDAY: 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 something I — I — I felt like was worthy of, you know, sort of making my — my life’s work and —

RITHOLTZ: Is it true you read the meditations four times in a row as a college student or is that just a (inaudible)?

HOLIDAY: It would have been — I mean, four times in a row is probably an — I — I probably read that book, you know, 200 times.



RITHOLTZ: Wow, 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. Write to us at Check out my daily column on You can follow me on Twitter @ritholtz. I’m Barry Ritholtz. You’re listening to Masters in Business on Bloomberg Radio.

Welcome to the podcast, Ryan. Thank you so much for doing this. This —

HOLIDAY: (Inaudible).

RITHOLTZ: You know, a little inside baseball, I prepare these daily reads for Bloomberg every day. And as I am — and I always assumes I hit Send, and 20 minutes later I find something interesting. And I find Derek Thompson —


RITHOLTZ: — of “The Atlantic” who wrote the book — I want to say it’s —

HOLIDAY: “Hit Makers”.

RITHOLTZ: — “Hit Makers”, right, who is previous —

HOLIDAY: Wonderful book.

RITHOLTZ: Yeah, wonderful — his previous guest to 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 so many questions we didn’t get to.


RITHOLTZ: I — I have to give you a few quotes of yours and have you push back —

HOLIDAY: All right.

RITHOLTZ: — on them. Blogging is a digital blood sport, explain.

HOLIDAY: Well, it’s not just this sort of battle inside a company for clicks, right, who is the best writer, who’s getting the best scoops. It’s — it’s this juror, it’s this intense battle between journalists at all of these different outlets. You got to be first, you got a — you got a brand new story, the best — you get the best headline.

All of these new sources are competing with each other for a finite amount of attention, so the blood sport that way, but then also we could say we take a — as a — as the — the view in public, we take a great deal of pleasure and watching people — and particularly well-known people get torn apart. So it’s this blood sport, I think, in both directions.

RITHOLTZ: Isn’t the history of that sort of tabloid journalism and that really gossipy celebrity rag type of approach to — to media has not been around for forever?

HOLIDAY: Yeah, I think Oscar Wilde said we used to have the racket, now we have the press. That’s how we used to torture people, and now we do it — you know, now we do it digitally. So — so I think it’s just that an — an escalation or a — a growth and a trend that’s always been there.

RITHOLTZ: Another quote, and this one was from “Trust Me, I’m Lying,” “My job was so easy that it scared me.”


RITHOLTZ: And you’re obviously referring to the media and your ability to manage the coverage they were doing. Explain why it scared you.

HOLIDAY: I’ll — I’ll give you an example. When I was putting on “Trust Me, I’m Lying,” I thought what can I do that sort of proves this book, right? And so I — I — I put out a press release where I announced the size of the advance, which I doubled.

RITHOLTZ: Wait, so let me — let’s — so you claimed the 250 advance —

HOLIDAY: No, I claimed the 250 advance was a $500,000 advance because nobody fact-checks press releases, right?

RITHOLTZ: Wait, so — so was the 250 you claimed 500?


RITHOLTZ: And people bought it?

HOLIDAY: Immediately picked up.

RITHOLTZ: And that became —

HOLIDAY: No one — no one —

RITHOLTZ: — tremendous amount of buzz about that book.

HOLIDAY: Right, where is this — who is this person? How did you just get a $0.5 million book deal?

RITHOLTZ: Nobody said, hey, this guy is writing a book about lying to the press.


RITHOLTZ: — maybe we should fact-check what he said.

HOLIDAY: Yeah, nobody said let’s call the publisher —


HOLIDAY: — and get the size of the advance, right? So that’s the first thing. And then —

RITHOLTZ: That is hilarious, you know.

HOLIDAY: So — 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 $0.5 million book deal? It must be a celebrity tell-all about his clients.”

RITHOLTZ: Oh, you’ve (ph) just basically led me —


RITHOLTZ: — to the lion.

HOLIDAY: He — he sends me an email, and I say, “I can’t answer this. No comment,” right? And —

RITHOLTZ: Manufactured buzz.

HOLIDAY: Right. Five minutes later, you know, is Ryan Holiday’s new book a celebrity tell-all? You know, boom, that story —

RITHOLTZ: Too easy.

HOLIDAY: — exists to this day —


HOLIDAY: — has not been corrected, and this is the same website that, you know, would attack me for writing this book or that would say, you know, Peter Thiel destroyed a venerable institution of journalism in his — in his — and it’s like actually, no, this was, in many cases, a rumor mill, right, a clearing house for rumors and gossip and 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 this as a joke for a book to prove a point, but what could I do if I wanted to propagate some racist theory or —

RITHOLTZ: If you have a more nefarious intent.

HOLIDAY: Exactly.

RITHOLTZ: Wow, that — that is just astonishing. Who was the media editor at “The Observer” when you were there?

HOLIDAY: Well, Ken Kurson was the Editor-in-Chief. That’s who edited my columns.

RITHOLTZ: Right. The one thing I didn’t get to about conspiracy earlier was MBTO, that was Peter Thiel’s —

HOLIDAY: Acronym, yeah.

RITHOLTZ: — for — for Gawker, tell us about that.

HOLIDAY: They call — his acronym stands for Manhattan-Based Terrorist Organization. And that’s — that’s what he believed.

RITHOLTZ: So that — this is really — this is not just a, hey, I’m annoyed that they did this.


RITHOLTZ: He’s really looking at them as a very significant problem —


RITHOLTZ: — for anybody who’s potentially in the public eye.

HOLIDAY: Yeah. And — and I think he deeply believed that, right or wrong. But it is the predilection of — and anyone in the 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 go.

RITHOLTZ: You demonize them and they’re no longer a person.


RITHOLTZ: So, we — we have the Hulk Hogan sex tape. That wasn’t the only sex tape. Didn’t — was it Fred Durst of Limp Bizkit? Am I remembering —

HOLIDAY: They run a number of sex tapes. And what was —


HOLIDAY: — so — and — and leaked celebrity photos. They’ve done a number of things. And — and what was actually so remarkable about it —

RITHOLTZ: The actresses’ cell phones with all the nude selfies on them —

HOLIDAY: What was —

RITHOLTZ: — I mean, that was — that was in the press for like six months, a different one every day.

HOLIDAY: What was so remarkable was that no one had actually taken Gawker to trial before, and that was Thiel’s insight, right? He felt like not only did most people not have the money, but most people didn’t have the determination or the stamina to take it by far.


HOLIDAY: And so there’s this remarkable moment at the trial that I talked about a pre-trial wherein the depositions, you know, the first question you’re asked at a deposition is have you ever been deposed before? And the answer from the folks at Gawkers universally no.

RITHOLTZ: That’s amazing.

HOLIDAY: All — the most controversial media outlet on the planet that had been —

RITHOLTZ: Never sued.

HOLIDAY: — never sued. And so they were in uncharted territory. They didn’t know how dangerous the predicament they were in actually was because they do have the (inaudible).

RITHOLTZ: Did 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.


RITHOLTZ: 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 arm’s length distance. Am I — am I overstating that?

HOLIDAY: No, no, I — 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 Obstacle is the Way” and “Ego is the Enemy”, and — and “The Daily Stoic” have been for me because they have — 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.

RITHOLTZ: 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 that.

HOLIDAY: Right. Well, I — 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 it there, right? And those are mistakes or — not mistakes, so those are choices that I live with and have learned from but —

RITHOLTZ: You’re a very — you know, I mean —


RITHOLTZ: — to be fair to you, you are 20 at American Apparel.


RITHOLTZ: At 20, I was, you know, going to CAGRS (ph) in college and getting high all the time. I can imagine having a real job at that age.

HOLIDAY: Yeah, and — and there are things I would do differently. They 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 is pretty safe. Do you know what I’m saying? Like he — he was the advisor to the worst ember (ph) in history —

RITHOLTZ: That’s right.

HOLIDAY: — a deranged psychopath. And he still felt that was consistent with stoicism. So I feel like it’s pretty generous.

RITHOLTZ: (Inaudible) —


RITHOLTZ: — you — you were advising the — the person who led to the fall of Rome.

HOLIDAY: Right, exactly.

RITHOLTZ: So — so you got vacuum.

Let’s get to some of my favorite questions —


RITHOLTZ: — 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?

HOLIDAY: 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 churns 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 — a normal person who writes books for a living.

RITHOLTZ: You — you seem pretty reasonable.

HOLIDAY: I try — I try to be. That’s — I would like to be a successful normal person, that’s my goal.

RITHOLTZ: Good, good goal. Tell us about some of your early mentors, who — who —


RITHOLTZ: — affected who you are and — and your philosophy.

HOLIDAY: Well, you know, one of the most trying things at American Apparel watching this company collapse and implode is that Dov Charney was this great friend of mine, this person who had seen talent and promise in me, who’d groom me, who’ve given me many opportunities. It’s very alarming when someone who says, “I see some of myself in you,” catastrophically implodes, right? You start question them.

But, you know, Robert Greene, the —

RITHOLTZ: The 48 —

HOLIDAY: — 48 Laws of Power —


HOLIDAY: — and Mastery, I was his apprentice on the side. As all of this is going on, I’m also a research assistant to Robert Greene.

RITHOLTZ: That’s fascinating.

HOLIDAY: 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 48 laws of power, I try to live my life the way that the author of the 48 Laws of Power who is this sort of disciplined, kind, generous person happens to live his — his life, in the profession that I’m also in.

RITHOLTZ: How did you find your way to Robert Greene? He’s such a fascinating character.

HOLIDAY: I was an enormous fan, and I was working for a different author who happen to know Robert, and I just wouldn’t — wouldn’t let go.

RITHOLTZ: Want to go, yeah. That’s interesting.

So, who else influenced your approach to media?

HOLIDAY: To media, well, one of the books I would suggest everyone read who — who’s looking to sort of understand media, there’s a book by Upton Sinclair called “The Brass Check,” (inaudible) the name of my marketing company as well. But he writes this book after “The Jungle.”


HOLIDAY: He writes an exposé of journalism in the — in the early 20th century, and it’s just as disgusting as the meat packing industry.


HOLIDAY: And if you could take the exact same book, replace newspaper with blog then it would be equally true today.

RITHOLTZ: So funny you say that. There’s this book from the early 20’s, 1920 something. I’m trying to remember the name of the author, How I Trade Stocks. And you could replace —


RITHOLTZ: — any of the dot coms with any of the —


RITHOLTZ: — telegraph companies, and everything is exactly the same. It’s — it’s amazing you said that same exact thing.

HOLIDAY: Well, that’s what the stoics say that history is just this constant repetition of the same people doing the same (inaudible).

RITHOLTZ: Human nature is unchanging, it’s no surprise.

So you mentioned that book. Tell us about some of your favorite books.

HOLIDAY: That’s a — it’s always hard to give general book recommendations but —

RITHOLTZ: 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 recommendations. So —


RITHOLTZ: — it doesn’t have to be general —


RITHOLTZ: — or it could be general or specific. It’s what books do you think are important to you have —


RITHOLTZ: — and if people enjoy it or not —


RITHOLTZ: — that’s on them.

HOLIDAY: So I’ll give you a couple. So, one, I would say everyone should read Robert Greene 48 Laws of Power and Mastery, incredibly important books.

I’m a big Rich Cohen fan. He wrote “Tough Jews,” he wrote “The Fish That Ate the Whale,” about Sam Zemurray, the founder of United Fruit, one of my favorite books of all time.

RITHOLTZ: “The Fish That Ate the Whale.”

HOLIDAY: Yeah. It’s a — it’s an incredible story of — of — of financial operations and entrepreneurism and — and, you know, government and —

RITHOLTZ: Rich Cohen.

HOLIDAY: Rich Cohen as I’m a huge fan of Rich Cohen. I’m a big William Tecumseh Sherman fan. He’s one of my favorite. I — I love Sherman and Grant, so I — both of their memoirs I would strongly urge people to read.

RITHOLTZ: Have you read the Chernow book?

HOLIDAY: I’ve read so many biographies of Grant that I feel guilty about reading another 1,000-page —


HOLIDAY: — but I love Chernow. His book on Rockefeller is fantastic.

RITHOLTZ: Sure. Titan, I think.

HOLIDAY: Yeah, his book on Andrew Hamilton is — is as good as you would expect.


HOLIDAY: His book on Washington is fantastic.

I’m a big biography fan. I think biography is how we learn.

And then I would say Plutarch’s lives, there’s a reason that almost every great historical figure is either in that book or obsessed with that book and then, of course, the stoics. If you — the most powerful man in the world, Marcus Aurelius sat down every night and wrote in the journal notes to himself about how to be a better person, and that survives to us. You would be —

RITHOLTZ: Meditation.

HOLIDAY: Yeah, you’d be an idiot not to read that book. I mean, it’s just an — an incredible historical occurrence.

RITHOLTZ: It’s literally 2,000 years old, and it just persists ongoing.

HOLIDAY: Exactly.

RITHOLTZ: That — that is for someone who 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?

HOLIDAY: I mean, I — I do think crypto currencies are interesting. The — I think someone will solve — someone will find a practical use for block chain. And — and I think it’s a race to find — there is a speculative bubble of crypto currency.

RITHOLTZ: Two separate things, the technology and the trading vehicle.

HOLIDAY: And — and someone will solve it, and I think that will be really interesting so I’m — I’m sub interested in that.

You know, I live in Austin. I — 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 —

RITHOLTZ: Keep going —

HOLIDAY: — the land, yeah.


HOLIDAY: And that — that that lines up with my experience, and — and I’m — I’m bullish on that.

RITHOLTZ: Although cities continue to attract young people in ever greater numbers especially now that jobs are — become fairly plentiful.

HOLIDAY: Yes, but I — I think like if my own career is somewhat ahead of the curve because I started early and — and got lucky in many ways, it’s that you go to the city, you make your body, you build a business and reputation, and then you can work from wherever you want, and then you go —


HOLIDAY: — why am I living in New York City.


HOLIDAY: And so I think that — I think it will be interesting to see how millennials shade (ph). Our millennials is going to move into the suburbs, back into the suburbs they grew up in or they’re going to (inaudible) their own thing?

RITHOLTZ: Right. The answer to the question is the food is why you live here. You can’t get good Chinese food on a farm —

HOLIDAY: Or not that (inaudible) but yes.

RITHOLTZ: — but if that’s not — if that’s — if that’s — or Vietnamese food or —


RITHOLTZ: — or go down the list, pick your favorite cuisine. But at a certain point, it’s hard living in a city versus having little elbow space and — and a big sky. That’s a very different lifestyle —

HOLIDAY: Agreed.

RITHOLTZ: — that — that I think suits you once you work through your 20’s and 30’s —


RITHOLTZ: — hypothetically.


RITHOLTZ: So we’ve been talking a lot about the media. What do you think the next set of changes are that’s going to wash over the media landscape?

HOLIDAY: 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 —


HOLIDAY: — the idea like the reason people pay for Bloomberg terminals is because those — the time and the information is extremely valuable to those people.


HOLIDAY: And, you know, millennials originally pirated music. We were never downloading anything.


HOLIDAY: And now we pay monthly for Spotify, right —


HOLIDAY: — because our time gets more valuable.

RITHOLTZ: Or — or Amazon Prime or Apple iTunes are going on in the list.


RITHOLTZ: You have a — it’s a — there’s a wealth of — of everything. I’m — I don’t know if you’ve discovered this, but I grew up in a year where you would actually get video tapes or DVDs.


RITHOLTZ: That’s done. Everything we watch on video is either Amazon Prime, Netflix, Hulu go down the list.


RITHOLTZ: Nobody is buying the sort of physical stuff anymore.

HOLIDAY: Yes, but I — I do think you’re going to see in the information space, people realizing that free information is very expensive, right.

RITHOLTZ: Free information —

HOLIDAY: It’s so wrong.

RITHOLTZ: — it’s worth what it cost you.

HOLIDAY: Exactly.

RITHOLTZ: So the “Washington Post” behind a paywall, The “New York Times,” the “Wall Street Journal” has always been beyond a paywall.

HOLIDAY: And they have a — I was just reading about their technology.

RITHOLTZ: It’s sort of a flex paywall.

HOLIDAY: It’s – yeah, how much should we charge you, how likely are you to pay, and I think that technology is only going to get better.

RITHOLTZ: Like they do with selling airline seats —


RITHOLTZ: — in other words/


RITHOLTZ: That’s quite — that’s quite interesting. Tell us about a time you failed and what you learned from the experience.

HOLIDAY: That — that’s always the tough question. I feel like I’ve been lucky in a lot of ways. My — my failures have been slips rather than falls for the most part. And so, in some ways, you know, the stoic exercise is to think constantly about the neck like to — to be prepared for some big setbacks, some big correction. So I — I do think about that a lot.

But, you know, when I was building my marketing company, I — I’m — 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 I — and I took on some partners and some investments, investor money and hired a bunch of people. And I remember my wife saying like you have the perfect thing, why are you doing this?


HOLIDAY: And I didn’t do 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 and I ended up being miserable. It was — I was working way more and making probably less money. 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.

RITHOLTZ: Right, that makes — that makes perfect sense. Tell us what you do for fun. You write an awful lot. What do you do to just relax?

HOLIDAY: I would say when I’m not writing that’s when 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 —


HOLIDAY: — how do I feel all this time, like it’s — that’s — that’s where I dedicate a lot of my energy.

But, you know, I — 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 if I’m doing both. That my favorite thing to do.

RITHOLTZ: And the new iPod has a water proof feature. You can actually listen to music in the pool.

HOLIDAY: I reject that entirely. I think the pool is the — I say the pool is the last quiet place on earth.

RITHOLTZ: That’s a fair statement.

HOLIDAY: No screens, no noise. It’s — I love swimming precisely because it’s one hour of nothing.

RITHOLTZ: You’re in the pool for a solid hour.

HOLIDAY: I try — I try 45 minutes to an hour, yeah.

RITHOLTZ: That’s a —

HOLIDAY: I try to do a mile, a mile and a half.

RITHOLTZ: — that’s a good workout, wow. 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?

HOLIDAY: 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 into writing. So when you were asking me about some of my controversial choices career-wise or things I’ve, you know, gotten myself in trouble with, 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 if I had done that.

RITHOLTZ: (Inaudible), yeah.

HOLIDAY: And — and it’s given me a perspective and an angle and, you know, material. And so a writer needs material more than they need. Anyone can write like, you know, I believe Keith Richards biography is written in crayon, you know —


HOLIDAY: — 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.

RITHOLTZ: 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 10, 15 years ago when you were first getting started?

HOLIDAY: 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 — all the things you would expect in your life. I’m describing what I would want to see in the ideal media outlet are essentially economically impossible, right? They’re economically impossible, and then worse, there’s a culture on top of it that — that — that exacerbates it rather than corrects or mitigates it.

RITHOLTZ: Are you referring to digital print, electronic, all the above?

HOLIDAY: I — I would say all of the above like a bias, but I think books are one of the few safer mediums, right, because you pay for books.


HOLIDAY: That takes a long time to make. They’re designed 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.

Rio Quite — quite fascinating. We have been speaking to Ryan Holiday, author of the book “Conspiracy: Peter Thiel, Hulk Hogan, Gawker and the Anatomy of Intrigue,” as well as several other books including The Daily Stoic.

If you enjoyed 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 187 such prior conversations that we’ve had. We love your comments, feedback and suggestions. Write to us at

I would be remiss if I did not thank my crack staff for helping to put together this podcast each week. Madina Parwana is our producer/audio engineer. Taylor Riggs is our booker/producer. Michael Batnick is our Head of Research.

I’m Barry Ritholtz. You’ve been listening to Masters in Business on Bloomberg Radio.


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