in: Advice, Character, Podcast

• Last updated: September 30, 2021

Podcast #412: The Power of Conspiracy and Secrets

Back in 2016, a bizarre story emerged in pop culture. Professional wrestler Hulk Hogan won a $115 million dollar lawsuit against the gossip website Gawker for publishing a sex tape that had been made without his consent. The victory was somewhat surprising but the real surprise was who was actually behind the lawsuit; it wasn’t Hogan himself, but the billionaire founder of PayPal, Peter Thiel. 
Thiel had his own axe to grind against Gawker, and he had been honing it since 2007. He had been plotting to take down Gawker for almost a decade.
What may sound like a tawdry story of celebrity and scandal, actually contains surprisingly potent lessons on revenge, Stoicism, strategy, perseverance, hubris, privacy, and the underrated power of secrets.
My guest today dug into this story and its insights in his new book, Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue. His name is Ryan Holiday, and he’s also the author of Growth Hacker Marketing, The Obstacle Is the Way, Ego Is the Enemy, andThe Daily Stoic. Today on the show Ryan and I discuss his latest book, and the lessons we can take from a story that reads much like a modern-day Count of Monte Cristo.

Show Highlights

  • Why was Ryan drawn to this story? How did he end up chronicling it?
  • How did Ryan choose an approach to this book? How did he write it differently than most journalists already had?
  • The backstory of and its outing of Peter Thiel 
  • Why it took 4+ years for Thiel to realize he could do something about it 
  • How did Thiel find and end up paying for Hulk Hogan’s case against Gawker? 
  • What Ryan meant in calling Thiel a “high agency” individual  
  • Can a person become high agency? Or are you born that way?
  • Why Thiel wants to be underestimated and under-the-radar 
  • Why competition is for losers 
  • The difference between conspiracy and war 
  • Why Thiel sought revenge rather than taking, say, a Stoic approach to the problem 
  • Did Thiel go too far? Why was his identity and scheme revealed?
  • Why secrecy can actually be an effective, powerful tool in getting things done 
  • The value of privacy in our modern transparent society 
  • How did all the players in this story turn out?
  • What happened when Thiel and Denton met in person?
  • Ryan’s takeaways on strategy, getting things done, etc. 

Resources/People/Articles Mentioned in Podcast

Book cover of Conspiracy by Ryan Holiday.

Connect With Ryan 

Ryan on Twitter 

Ryan’s website

Ryan on Instagram

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Read the Transcript

Brett McKay: Welcome to another edition of The Art of Manliness Podcast. Back in 2016, a bizarre story emerged in pop culture. Professional wrestler Hulk Hogan won a $115-million lawsuit against the gossip website Gawker for publishing a sex tape of him that had been made without his consent. The victory was somewhat surprising, but the real surprise was who was actually behind the lawsuit. It wasn’t Hogan himself, but the billionaire founder of PayPal Peter Thiel. Thiel had his own ax to grind against Gawker and had been honing it since 2007. In fact, he had been plotting to take down Gawker for almost a decade. And what may sound like a tawdry story of celebrity and scandal actually contained surprisingly potent lessons on revenge, stoicism, strategy, perseverance, hubris, privacy, and the underrated power of secrets.

My guest today dug into this story and its insights in his new book Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue. His name is Ryan Holiday. Had him on the show several times. He’s the author of Growth Hacker Marketing, The Obstacle Is the Way, Ego Is the Enemy, and The Daily Stoic. Today on the show, Ryan and I discuss his latest book and the lessons we can take from a story that reads much like a modern-day Count of Monte Cristo. After the show’s over, check out the show notes at Ryan joins me now via

All right, Ryan Holiday, welcome back to the show.

Ryan Holiday: Yeah, thanks for having me. It’s been a while.

Brett McKay: Yeah. I think this is a three-peat for you. I think you’re one of the-

Ryan Holiday: Is that a record?

Brett McKay: Well, no, it’s not a record, but it’s exclusive company.

Ryan Holiday: Okay.

Brett McKay: I think there’s like only two or three people who’ve done the three-peat.

Ryan Holiday: I’ll take it.

Brett McKay: Well, you got a new book out. It’s called Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue. This is a book about one of the most bizarre legal cases in American media history. We’ll get into some of the details later on for those who aren’t familiar with it, but I’m curious, how did you end up being the guy who sort of wrote the history of this weird case involving billionaires, a millionaire, a media mogul, and the Hulk? How’d that happen?

Ryan Holiday: In some ways, I have no idea. It caught as much by surprise as I think it caught anyone else. In some ways, I think it’s a little bit of right place, right time, but to me it’s also this is why you put yourself out there and you take risks and you try to write about different things. That it’d written pretty extensively about media over the years, and I wrote a column about this case because I was following it in the news. Just the idea of this billionaire plotting in secret for 10 years to get revenge was my initial take on what had happened, and I wrote this article about it. And Peter Thiel, who was that billionaire, sent me an email about it after, so he and I started talking. And then I wrote a column about why people should stop watching the news, how we consume way too much news, and I sort of took a philosophical take on this. And then I got an unsolicited email after that from Nick Denton, who is the founder of Gawker, who is the company Thiel had taken his revenge out on.

So I was sort of thinking about doing a book, and then I had access to both these two principles. It occurred to me I was probably the only person on the planet talking to these two mortal enemies. And then I just sort of floated the idea to my publisher, and it was off to the races. And it was really intimidating and scary, obviously, not having written in this sort of narrative, nonfiction form before and writing about a guy who’d just bankrupted $100-million company he didn’t like. So it was scary in a lot of ways, but to me mostly, those are exactly the kind of projects you want to take on as a writer, and so all of those things kind of came together, and the book is a result of that.

Brett McKay: How did you approach this book? Because, okay, it’s about a sex tape, and so it’d be easy to be just focusing on that and the sordid detail of that, but you didn’t do that. You seemed to take a more of a philosophical approach in how you retold the story and also what we can learn from it.

Ryan Holiday: Well, one of the weird things, because this has obviously been an intensely-reported story. It involves Silicon Valley and New York media and the media itself and the First Amendment and a professional wrestler. It’s all these things, so it’s been covered by journalists a lot. And what felt like they fundamentally got wrong, and I think we see this across the board with a lot of media coverage and when people watch sports and have comments or when they follow politics and they have comments, people want to argue with other people’s motivations.

Peter Thiel said he did this because he thought it was about justice and it was about improving the world. And then everyone in the media said, “No, that’s not true. You did this because you’re afraid or you’re evil or all these things.” It’s like, if I tell you, Brett, that I’m offended, you can’t argue with me over whether I’m offended or not, but what you can do is take the time to figure out why I feel the way that I feel.

And so what I tried to do in the book, ultimately, and this was a stretch for me as just a human being who had preconceived notions myself, is like, okay, why did this guy who’s worth billions of dollars, who could do anything he wants with his time, whose founded these enormous companies, PayPal, he’s the first investor in Facebook, he’s the founder of Palantir, why on earth would he have spent all this time on this thing? It must have been really important to him, and he must’ve had some sincere motivation. So I’m going to ask him, and I’m going to figure out what that is, and I’m going to try to express it as vividly and as deeply as he feels it.

And then on the other hand, it’s not as if Gawker, and we’ll sort of, I guess, sort of drop in little hints of the story, but the reason Thiel and Gawker were opposed to each other is that a Gawker writer in 2007 had outed Thiel as gay. Now, when Gawker wrote this article, they weren’t thinking, “What’s the cruelest, meanest, scummiest thing that we can do?” They were thinking that this was important, that this was newsworthy. They had their own motivations. There’s this line from Socrates where he says, “Nobody does wrong on purpose.”

And so one of the premises of the book for me was like, let’s figure out why everyone did what they did and try to explain it. And once we lay this all out, then the reader can judge who’s the good guy or the bad guy. And I think too much of what we see and read and hear these days is designed to tell us how other people feel rather than get to the truth of that actual feeling, if that makes sense.

Brett McKay: Yeah, that makes sense. All right, let’s get some background for this because I want to delve into some points, but I think it’s important for … We got to understand sort of the story. You mentioned there was a website called Gawker, 2008, published an article outing Peter Thiel as gay. Well, talk about Gawker. I mean, for those who aren’t familiar with Gawker, what is Gawker and what sort of websites do they run?

Ryan Holiday: Gawker starts as a blog in Nick Denton’s living room. The first one is about tech gadgets, the second is about gossip, and it very quickly just explodes. Tens of millions, eventually billions of page views a month in a year. And it is a website that sort of revels in being an outsider and revels in critiquing and holding powerful people to account. That’s how they see it.

Now, a couple tweaks on that. One, Gawker loved to write the stories that other people wouldn’t write. So if there was a rumor that someone else didn’t feel had been verified, that’s the kind of story that Gawker would love to run. If someone had stolen something and was trying to leak it to the media, and the media was like, “Well, I don’t know where this came from,” that’s the kind of scoop that Gawker wanted. And then on top of this, Gawker was the website that pioneered the strategy of paying their writers at least in part based on how much traffic their articles do.

So it’s this explosive controversial media company that starts really small, it stays independent, and then it becomes incredibly powerful by writing the kinds of gossipy, dark, no-holds-barred stories that readers love to eat up.

Brett McKay: All right. Then, in 2008, they wrote just sort of an offhand article, “Peter Thiel is gay.”

Ryan Holiday: Yeah. In 2007, they published an article, and the headline was, “Peter Thiel is totally gay, people.” And it’s an anonymously-sourced article that posits that Peter Thiel, who is essentially an unknown person outside Silicon Valley at that time, is not only gay, but Nick Denton speculates at the bottom of the piece that there’s something … that why is he so secret about it? What is he hiding? Why is he ashamed of being gay? And this is Thiel’s rude introduction to this media company and how they work.

Brett McKay: Also, Denton is also gay, so it’d be kind of-

Ryan Holiday: Denton is gay, and the writer who writes it is gay. And this is actually sort of an MO of Gawker. They were one of the first to report that Anderson Cooper was gay. They’ve outed a number of other people. And Denton would say that he believed that it was only out of a misplaced sense of decency that media outlets refuse to do what Gawker was doing. So it is a strange, contrarian, unusual worldview that Denton and Gawker has, and that’s what puts them on this collision course with Thiel.

Brett McKay: Okay. Thiel got outed, and he didn’t like that. I mean, why is that? Because this is 2007, it’s the 21st century, acceptance of homosexuals is pretty mainstream at this point. Why did this-

Ryan Holiday: We got to go back in time. Prop 8, which bans gay marriage in California, hasn’t even been passed yet. That’s months in the future. Obama obviously hasn’t been elected in 2007, and he himself and Hillary Clinton, neither of them have come out in favor of gay marriage. So it is not what it is today back then.

But I think primarily what Thiel objects to is, why the hell is this anyone’s business? I don’t know the sexuality of any of the other early investors in Facebook. And I think his point was, “Why are you writing this about me? What did I ever do to you? And even if you are writing it about me, why are you writing it in such a cruel and mean way? Why are you implying that there’s something wrong with me for wanting to keep this private piece of information private?” And so he stews on this. He doesn’t do anything right away. He can’t. It’s not illegal to out someone. It’s certainly in bad taste, but it’s not illegal.

And so for the next several years, literally years, he just sort of despairs of being able to do anything about this. He meets Gawker writers, and he asks them about it. He talks to a sort of a notorious New York City sort of fixer, a lawyer and PR genius, and they’re basically like, “Look, this is the new reality for you. You are going to be a target for these websites. You’ve just got to take it.” And Thiel, he just doesn’t like that, and he doesn’t want to have to accept that.

Brett McKay: So he stews on it, and I think he kind of resigns himself to the fact that there’s nothing he could do about it because Gawker could always claim First Amendment, right?

Ryan Holiday: Yes.

Brett McKay: And that was a big protection for them.

Ryan Holiday: Totally. And rightfully so. I mean, the media has special protections and centuries of precedent protecting its right to do what it had done to Thiel. So it’s not until 2011, so four-plus years later, that Thiel has a dinner in New York City with a young man. Thiel obviously, as an investor, is always looking for sort of ambitious young people who he can place in startups or invest in, and he meets with this kid, really. I call him Mr. A in the book. He is not-yet been identified.

And Mr. A essentially pitches to Thiel, he says, “Look, I know what Gawker did to you was upsetting but not illegal. But here’s the thing. I think they may have done other things that more clearly cross various legal lines. Maybe it’s copyright violations. Maybe it’s invasions of privacy. It’s intentional infliction of emotional distress. Maybe it’s defamation. Maybe it’s libel. A website that would push the boundary so far in what they did to you, may have pushed it more egregiously so in other instances.” And he says, “I have a plan. I have a legal firm I think we can work with, and I think with about a $10-million budget and three to five years of runway, I think we can take these people down.” And he says, “I think the world would be a better place if you did this.”

And Thiel says to him, “Look, I’ve thought about this. There’s nothing you can do about it.” And Mr. A looks him in the eye, this is incredible that this 26-year-old kid would do it, and he says, “Peter, if everyone thought that way, what would the world look like?” And that’s sort of exactly what Thiel needed to hear, and he ends up backing what I call a conspiracy for the next five years on the spot. He basically gives him an unlimited budget and says, “Let’s do this.”

Brett McKay: Okay. That’s some great stuff. We’re going to unpack some of the stuff you just talked about. How did they end up representing or paying for the Hulk Hogan case? How did they connect there?

Ryan Holiday: Again, though, Thiel puts up this money, but it’s not money that’s going to win this sort of war against Gawker. What Thiel knows is that he needs the right case. If Thiel had thrown $10 million, again, litigating his case against Gawker, that they’d outed him, he would’ve lost. And so what he and Mr. A do, and the lawyer that they ultimately hire and his team do, is they begin to troll through Gawker’s archive to find examples of it potentially violating laws in various places. And they don’t find anything that immediately stands out. And they do this for about a year, and it’s not until October of 2012 that Gawker runs a stolen sex tape of the professional wrestler Hulk Hogan that had been recorded without Hogan’s consent by his best friend, of all things, that they realize that they may have the case of a lifetime here.

Again, I know some of these sensational details might just seem uninteresting to people or unimportant, but I think what I tried to do in the book and what I think is so important about what Thiel did here is that he didn’t just rush into this. First, he waits, then he assembles the right team, but then most importantly, he waits for the right opportunity. He said to me that capital wasn’t the scarce resource. It was having the right creative idea. And so he has this patience to wait literally like several years until this Hulk Hogan opportunity comes his way that then they’re able to file a $100-million lawsuit on Hogan’s behalf. Gawker has no idea that Thiel is responsible and totally laughed the case off. But it’s because Thiel had the patience, like a great investor, to wait for the right opportunity that he’s able to put himself in a position to win.

Brett McKay: Okay. So yeah, they end up winning the case. Let’s talk about the lessons from that. Because that’s what I loved about this book. It was sort of something like Machiavelli or Plutarch would write, right?

Ryan Holiday: Yes.

Brett McKay: They would take just these stories of intrigue and like, what can people learn about this, about morality, about strategy, et cetera? Let’s talk about that you’ve written that Peter Thiel is a high-agency person. What do you mean by that? What are the attributes of a high-agency person?

Ryan Holiday: Well, honestly, it’s very flattering to me that you said Plutarch because that was sort of a model for me writing the book. Plutarch has this series called Parallel Lives, where he sort of contrasts and compares really epic people, like a Cicero and a Caesar, and in some ways, I feel like Nick and Peter and people like that. So that’s what I tried to do in the book.

A high-agency individual is also like those epic characters from history that we love, I think would fall in that category. The phrase comes from someone who works with Peter, a guy named Eric Weinstein, who’s this sort of brilliant mathematician and economist. He says that there are people who when they hear “no” accept that they’ve heard a “no,” and then there’s people who hearing “no” begins a very different conversation for them, that they try to see what can be done. They don’t accept that “no.” And I think Thiel and Mr. A are good examples of that.

Thiel said it took him a while to get there, to be a high-agency person, but he just doesn’t like being told that there’s nothing you can do about the situation. And I think that’s why he stews on it for so long and why he lights up when he hears Mr. A’s plan because he’s like, “Oh, I don’t have to accept this.” And if everyone in the world accepted everything that they didn’t like, things would never change, and they would certainly never get better. And so he sees he’s on this slim but ambitious plan to do something about Gawker because he’s a high-agency individual who does not want to resign himself to the status quo.

Brett McKay: How do you think one becomes a high-agency person? Is it something about Thiel’s background that … Is it genetic? It is temperament? Upbringing? Or can you actively decide, “I’m just going to not take ‘no’ for an answer no matter what”?

Ryan Holiday: Yeah, that’s a good question. I mean, entrepreneurs are by definition high-agency individuals. You are trying to make something where there isn’t a thing before. So that’s part of it. But I think it’s about practice. Thiel had started one company. He’d started another company. He’d started a third company. He’d done this, so he’d experienced many times in his life people telling him that things were the way they were for a reason and that they couldn’t be changed and that it was impossible for a little guy to beat the big guy or for this person to do this or that. And so I think he’d slowly built up this sort of reservoir of confidence that told him, “I don’t have to listen to these people.”

He has a quote that I have in the book. He was talking about, he’s like, “Actually, I’m not that interested in things that people don’t think are possible.” He’s like, “Those things are kind of interesting to me.” He’s like, “What’s really interesting to me, the things that I think I’m really right about are the things that other people aren’t even thinking about at all.” And so what was so incredible about this conspiracy is that no one … It’s not like people suspected that something was behind it and they just didn’t know who. It’s that literally no one even considered something was happening. Myself included.

One of the Gawker editors says this, he’s like, “We scarcely could’ve believed that something so conspiratorial could’ve happened.” And of course, that’s exactly why it happened. And so I think Thiel specializes in finding the things that other people don’t think are viable, and that’s what he bets on. And ideally, he wants to be underestimated or not even considered at all because that’s where the really big opportunities are.

Brett McKay: Yeah. And that goes counter to how a lot of people approach success in our modern world. They want as much attention as possible, but Thiel likes to fly under the radar.

Ryan Holiday: Yeah. I think a lot of us sort of gravitate towards where there’s competition. Lots of people want to be professional football players, so we think that would be fun. Or we hear lots of people go to Harvard, so we want to go to Harvard because it must be good because a lot of people want to go there. And I think Thiel’s point … Thiel has this line in his book Zero to One, which everyone should read even if you don’t like Peter, even if you disagree with him. And he says, “Competition is for losers.” And I love that line because it’s true. What you ideally want to do is find where there’s no competition, where you’re the only one.

When you launched Art of Manliness, it’s not like there was 500 other manliness websites, and you were just 10,000 times better than them. It’s that you were the only one. And so what’s interesting now is someone might be listening to this and they see what you’re doing, and they’re like, “Oh, I’m going to make a website about how to be a man or how to be a better man.” And that’s actually the wrong lesson. What you should do is find something new or different that was as new and groundbreaking as Art of Manliness was when you started it.

So that’s what I try to do with my books, and I think that’s what Thiel tried to do with this conspiracy. He tried to do the thing that no one even thought was possible.

Brett McKay: Right, yeah. So that, “competition is for losers,” he makes a point. That’s a good point about strategy, right?

Ryan Holiday: Yeah.

Brett McKay: Because competition is costly. You have to spend a lot of money outcompeting your competition. In war, was is extremely costly. It’s like, lives and money. But the conspiracy thing, okay, let’s talk … This is basically a story of revenge. Because I thought it was interesting. When I was reading this, I was like, “Man, this is just like the Count of Monte Cristo.” What he did was an act of competition. He had to spend a ton of money, a ton of bandwidth, and a ton of … So how does that jibe with his idea competition is for losers, and here he is, secretly, but he’s competing.

Ryan Holiday: That’s true. But let’s think about the difference between, say, a war and a conspiracy. Sometimes conflict is inevitable. Two people have two competing visions or two people are jockeying for something, and so only one of them can be victorious. Machiavelli talks about this. He says, “Look, only the really powerful or the reckless can afford to go to outright war with each other, like two armies in the field clashing.” But Machiavelli says a conspiracy is more secretive and effective and can be wielded by anyone. And so what Thiel didn’t do is sort of announce that he was going after Gawker and that he wanted to destroy them.

Nick Denton said this to me, he’s like, “Why didn’t Thiel just write about what his critique of us and start a conversation about it?” And Thiel’s point is that that wouldn’t have worked. That’s why he didn’t do it. What Thiel said was, “I’m not going to let them know that I’m coming for them. I’m going to operate in secret. I am going to find a weak point or an undefended sort of chink in their armor, and that’s where I’m going to plow all my resource.”

And so in some ways, it’s like finding the exhaust vent in the Death Star. You’re not trying to win a war of attrition necessarily, or you’re not trying to just match strength against strength. You’re trying to put strength against weakness. And so what Thiel did here, again, first off by just not even pursuing his own case but by pursuing other cases, he’s already put Gawker at a disadvantage because they don’t know who they’re fighting against. But then he looked for the most egregious violations that they’d made, and he did it in things that they didn’t expect to be attacked for.

If you’re a celebrity, and a stolen sex tape of you is run on a website, the last thing you would rationally do is sue about it because you’re only going to draw more attention to it. And so what Thiel did by sort of taking care of Hulk Hogan and said, “Look, you don’t have to spend a dollar of your money here, and you can keep all the winnings if you win, you just have to let me back this on your behalf,” he was catching Gawker off guard because they didn’t think Hulk Hogan was going to go the distance on this $100-million lawsuit. They just assumed he would settle at some point, and then this would all go away.

Brett McKay: Staying on this idea of revenge, it’s interesting because you’ve written a lot of books about stoicism. We’ve had you on the podcast to talk about stoicism. The stoic would probably tell Peter Thiel, “Well, if someone writes this mean thing about you, you’d just ignore it. You don’t have any control over that. Just move on with your life.” But he didn’t.

Ryan Holiday: Sure. No, no. That’s a great point. And you’re absolutely right, the stoics would say that. I mean, Marcus Aurelius has a great quote. He says, “The best revenge is to not be like that.” If you think what Gawker did was disgusting and vile, your best revenge is just to be a better person. But again, this goes to my original point is, I’m not arguing with what Thiel felt or whether he should have felt that or not. He felt that this was deeply wrong.

And the stoics are also advocates for justice, and I think what Thiel felt ultimately was that what Gawker did to him and to other people wasn’t simply mean or hurtful but was genuinely wrong and needed to be stopped. And so I think he told himself that this was this quest of good against evil, and I don’t make any judgments about that because that’s what he felt, and we should try to understand what he felt just as we should try to understand what Gawker felt. However, what I think that quest allowed him to do was rationalize partly this quest of revenge and allowed it to make it bigger than himself, so he didn’t have to stop and think, “Hey, am I doing this for me, or is this actually about other people?”

Look, revenge is very dangerous. I mean, look, two famous expressions about revenge, “Revenge is a dish best served cold.” We think that’s about taste, but the more that I thought about it, it’s that the dish is hot. You don’t want to touch the dish. You’ll burn yourself. And so you need that patience, and so that was one of the things that Thiel had.

But the other famous saying about revenge is, “If you set out on a journey of revenge, first dig two graves.” And there’s a cautionary element in this story for that reason. I mean, Thiel sets out to fight this battle for his privacy, and he ends up becoming more famous as a result. And he ends up doing, I think, some things you could only charitably describe as quite dark in pursuit of this revenge. So it was not without cost to Thiel either, and that’s the thing. If you’re thinking about revenge, you’ve really got to weigh those costs and benefits because it might not be as satisfying as you think.

Brett McKay: Right. Yeah, there’s that other line, too, about, “Be careful who your enemies are because you end up like them,” or something like that.

Ryan Holiday: Yes. Yeah, and that was something that one of Thiel’s friends told him, and he obviously pursues it anyway. But there’s an argument to be made that in some cases, Thiel and Gawker just switched places at the end of the story. At the end, Thiel is the powerful one who destroyed someone, who embarrassed and humiliated them. There’s also the quote, “Those who fight monsters must be careful that they do not become a monster,” so that’s what’s so epic about this story.

I think we should remember, when you read history, when you read Plutarch or Machiavelli or even Homer, like the Iliad and the Odyssey, none of the characters are fully good or bad. They embody these sort of larger-than-life traits that we’re supposed to learn both what to do and also what not to do. And I think there’s a lot of that in Peter, and I definitely think there’s a lot of that of Gawker and Nick Denton. Hubris is probably the main theme on both sides through this book.

Brett McKay: Yeah. Gawker’s obviously hubristic because they just thought they could do anything and get away with it. How did Thiel display hubris?

Ryan Holiday: Well, first, I think that he thought he could get away with this. Not only did he think he would never get caught. At the end, as this case was sort of winding towards its verdict, and it became very clear to him that they were going to win, he still ends up pursuing other cases, several other cases on behalf of other clients against Gawker that are so sort of over-the-top and much less legitimate, I would say, appear to be much less legitimate than the Gawker case. And enough of this happens in a small amount of time.

Plus, Peter has begun to loosen his lips. He starts telling privately other people that he’s been doing this. And eventually, all of this contributes to his identity being revealed after the verdict. He could’ve gotten away with this had his discipline not relaxed, even just a half breath, the way that it did, perhaps he would’ve gotten away with it. And I think he regrets that.

Brett McKay: Yeah. I mean, I think a lot of war strategists have said that the most dangerous time in war is at the point of victory.

Ryan Holiday: Yes.

Brett McKay: And that’s what happened here.

Ryan Holiday: Yeah. I mean, Robert Greene talks about this. Do not go past the point that you aimed for. And I think Thiel wanted to win a knockout blow against Gawker but ends up piling on after. Actually, I would talk to Hulk Hogan about this, and he would say, “Look, that’s a lesson that I learned in wrestling, is you’re winning, but if you beat up too much on the other guy, the crowd turns on you, and the hero becomes the villain.” And I think that’s part of Thiel’s story.

I mean, look, he’s a billionaire, and he kind of likes controversial, contrarian things, so I don’t think it’s keeping him up at night. But I do think it would’ve been easier and better for him had he managed to get away with this entirely. And part of the reason that he didn’t is that he just told one too many people because he was so proud of it.

Brett McKay: Yeah. This book, it’s called Conspiracy, you call what Thiel did, it was a conspiracy. Because, okay, conspiracy, it’s a legal term. It’s something that’s done in secret when there’s more than one person involved.

Ryan Holiday: Yeah. And I think it’s typically something that’s disruptive. Two friends don’t conspire to go get ice cream, but you might conspire to get the mayor of your town impeached, or you might conspire to start a protest for civil rights. There are things you can conspire to do … They’re typically disruptive. That’s not to say positive or negative, but they are disruptive.

Brett McKay: Yeah. But we live in a society, an age that puts a premium on transparency. We don’t like secrets. But from reading the book, you kind of get the impression that, wow, no, secrets can actually be very powerful, a powerful tool in getting things done. Why is that? Why are secrets so good in getting … Why was Thiel’s obsessed … Because it seems like he was a very private person.

Ryan Holiday: Right.

Brett McKay: What’s his background that made him think that privacy, secrecy, not being fully transparent actually could help you get more stuff done?

Ryan Holiday: Well, there’s this line from Napoleon where he says, “Never do what your enemy wants you to do for the reason that they want you to do it.” If someone says you should do something, it’s probably better for them than it is for you. And so I think one of the interesting things about secrecy is the fact that people don’t want you to keep secrets is probably evidence that there’s something powerful or valuable in secrecy. And so I think Thiel’s point is, “Why would I tell Gawker that I was coming for them if that would make it easier for them to defend themselves?”

We see this now in the social media world that we live in. It’s like you have to tweet about every frigging thought that you have. People, for instance, are always asking me, they’ll say, “What’s the next book that you’re working on?” It’s like, why would I tell … Unless there was a clear marketing purpose because it’s … why would I want to alert my competition of what I’m working on and give them a chance to beat me, or give them a chance to undermine my argument or be prepared to undermine it? And so I think part of what secrecy is, is about planning and trying to do something ambitious enough that there are going to be people who want to stop you, and those are precisely the people that you want to keep your secrets from. And so I think that is one element of it.

The privacy element, I think is related but distinct. I think Thiel’s point about privacy is that, look, we’ve got to give people room to have controversial thoughts, to try different things, to be different or weird. What Gawker did was a nondiscriminating hater. They would make fun of anyone for anything, so if you tried something and failed, Gawker loved that because they would make fun of you for it. If you had a weird belief, Gawker would make fun of you for it. If you, I don’t know, took a risk and tried to do something different with your clothes, Gawker would make fun of you for it. If you tried to explain yourself about some controversial issue, and you failed, Gawker would nail you for it.

And so all of this is this sort of intense scrutiny and criticism of people instead of giving them space to experiment and try things, and I think that has a societal and cultural cost of making us more conservative and risk-averse, and it also prevents … The way to have good ideas is to have lots of bad ideas. But if we mock and criticize everyone for every bad idea and, conversely, if we tweet every bad idea that we have, we’re not going to have the space we need to filter the good from the bad.

Brett McKay: Right, yeah. Because people won’t let you live it down. That’s the thing I’ve noticed, right?

Ryan Holiday: Yeah.

Brett McKay: Is they’ll always remind you about your bad idea, and it’ll dog you for the rest of your life.

Ryan Holiday: Yeah. And then, people who are afraid of that will stop even trying at all. I think Thiel’s point is it’s very hard to measure what we lose because of that, but it’s probably very, very costly. We say we admire someone like Elon Musk, but we don’t really create room for there to be more Elon Musks because we hit them so hard early on in their career before they become Elon Musk that we prevent that from ever happening.

Brett McKay: Yeah. One of the problems with conspiracies is that you have conspirators that are in on the secret. What did Ben Franklin say? “Once two people know about a secret, it’s no longer a secret.”

Ryan Holiday: Yeah. Right.

Brett McKay: How did Thiel keep the funding of his lawsuit a secret for so long? You had Hogan that could’ve just bailed on this at any moment. He had all these people who knew about it, but they didn’t disclose. How did he keep that tightness in the group for so long?

Ryan Holiday: Well, that’s a great point because it also helps you realize why most conspiracy theories aren’t true. When people talk about, “Was 9/11 an inside job?,” the amount of people that would’ve had to be in on that conspiracy for it to be real is just so improbable that it can’t possibly have happened. But in this case, what Thiel did was Thiel hired Mr. A, Mr. A hired Charles Harder, who’s the lawyer, and Charles Harder solicits representing Hulk Hogan. So there are all these layers that are obscuring who is really behind it.

So the lawyer and Hulk Hogan both are in the dark about who is actually funding this lawsuit. They just know that a business person is funding it. So that was their secret, but they didn’t even know the full secret that they were keeping, and I think that was a big part of it. Let’s say you have a company, and you have this larger strategic vision. Obviously, certain people in the company need to know it, but not everyone in the company needs to know everything about it. Down to the doorman doesn’t need to know everything that you’re doing.

                                    Apple, for instance, is a very secretive company, and that’s part of how they manage to surprise us with all of these amazing products, is that news isn’t getting out as it’s happening, and so we don’t have super high expectations each time. We’re kind of caught off guard. We’re like, “Wow, I didn’t even know that I wanted that.”

So secrecy is important for a lot of reasons, and there’s a lot of ways to do it. There’s this line from a Roman general that I quote in the book, and one of his men says, “What time are we moving out tomorrow, are we marching?” And the general says, “If my shirt knew the answer to that question, I would burn it.” He’s like, “No one is going to know except me, and that’s going to give us an edge over our enemy because the more people that know, the more likely it is that the enemy will find out.”

Brett McKay: How did all the players in this story turn out? What happened to Denton? He lost his $100-million company.

Ryan Holiday: Yeah. A $300-million company. Yeah.

Brett McKay: Okay, $300-million. That’s a big deal. What happened to him?

Ryan Holiday: Right. The verdict comes back. It’s $140 million verdict. It bankrupts the company. They have to sell it off. Denton leaves the company. Two interesting players are Nick, who is the owner and founder of the company, and then a guy named A.J. Daulerio, who was the editor who ran the story of the Hogan sex tape. And what’s so interesting about them, what I say in the book is that although Thiel wins, there’s very rarely much character in winning. Winning sort of doesn’t often make you better. But on the other hand, Denton and Daulerio lose everything, and there often is a lot of character in losing everything because it forces you to question so many things.

One of the weird twists of this story and why I was motivated to write the book is that it turns out that both Denton and Daulerio turned to stoic philosophy, and actually happen to have read my books, because they were looking at how to sort of pick up the wreckage of their lives and move forward. Because that’s the only thing that you can do. And so A.J. ends up going into recovery and gets clean and sober, and he has a family now, and he’s trying to sort of rebuild his life as a writer. And Denton got married and is thinking about starting a family and has moved to Europe and is just sort of exploring what he wants to do next.

But what I think is so remarkable is even if you think that they deserved what happened to them, it would also follow that both of them would be bitter about the experience. I mean, to have been destroyed by this person who is so much more powerful than you over something you’d totally forgotten, that’s a bitter pill to swallow. And yet neither of them are, and I think that’s to their credit. Both of them are resilient, strong people who just said, “Look, I can’t control that this happened to me. I’m not going to let it ruin my life. I’m going to move on, and I’m going to do something next.” And that’s where they both are.

And look, to a certain degree, we have to give a little bit of credit to Peter in that Peter was willing to settle and let this thing go. He didn’t want to salt the earth after his victory or destroy them completely. He was willing to let them move on. And so I think if there’s any happy ending in this, it’s that everyone has sort of moved on to whatever they’re going to do next.

Brett McKay: Did Thiel and Denton ever meet face to face after this thing happened?

Ryan Holiday: They did. I mean, just the idea, that is so insane that both of these men who’d spent tens of millions of dollars fighting each other, that one had destroyed the other in court, the other had humiliated the other in the media, and they end up meeting after the verdict because even though it was a large verdict, eventually, these things can be appealed and fought, and they can drag on for years to the point where no one actually gets the money. The saying is that, “The lawyers are the ones who always win.”

Thiel and Denton meet. They meet first at the house of a friend, and then later again in a conference room in New York City. And they hash this thing out, and they say … Both of them are very suspicious of each other. Neither of them is willing to budge much, but they come to kind of a hard peace. And so far, that peace has held, and they’ve both gone on and done other things.

Brett McKay: How’d the Hulk turn out in all this? Is the sex tape gone?

Ryan Holiday: Well, the sex tape is mostly gone. And look, he walked away with many millions of dollars, so I think he’s doing all right. But again, having won, I’m not sure how much sort of reflection and character comes from winning. I think he’s actually quite proud of what happened. I think he thinks he improved the world by it. Again, that’s his opinion, and we should sort of probe that and grant it while not necessarily agreeing with it wholeheartedly. But I think he saw this as kind of a big part of the third act of his life.

Brett McKay: Yeah. I mean, the Hulk had a rough go going up into that thing. Son’s in jail, his wife divorced him and left him for a younger man, daughter’s career really wasn’t going that great. So this kind of …

Ryan Holiday: Yeah. The tape itself was a sort of culmination of the darkest period of his life, and so perhaps the case ultimately is sort of closure and what allows him to move on and do whatever he’s going to do next. So I think there was a catharsis in it for him for sure.

Brett McKay: Throughout the book, you not only talk about sort of strategy and how to get things done, but you’re also using it as a chance to explore our current media age. And after this thing happened of the verdict came in favor for Hogan, and people found out that Thiel was the one that funded it, like you said in the beginning, there’s all this handwringing like, what does this mean for media? Does this mean that billionaires can just take out media companies they don’t like? What do you think are the implications of this case going forward in the media?

Ryan Holiday: I actually think the precedent legally is much less than people are worried about because the truth is, most media would never run this story to begin with. And so Thiel nailed them on a very narrow sort of invasion of privacy claim. And I think before Thiel’s involvement was revealed, that’s what most legal experts thought as well. It’s just the context changes when you find out a billionaire brought it about.

But I think the general idea of using a lawsuit as a weapon to destroy someone, to go after an enemy, I think there is some larger precedent there. I mean, look, Alex Jones just got sued multiple times for defamation. Donald Trump might get brought down by the Stormy Daniels case. James O’Keefe, the sort of conservative media provocateur, is fighting a number of legal battles. I think people are realizing that, oh, just criticizing someone in an op-ed isn’t really doing it anymore, and if you want to stop them, you have to pursue other, perhaps more involved or permanent means of doing so.

Brett McKay:Do you t hink other blogs like Gawker, this was a wake-up call for them to actually kind of have some ethics about what they decide to publish or not publish?

Ryan Holiday: I think so. I mean, probably for better and for worse. On the one hand, the media is going to be more conservative about attacking potentially litigious people. On the other hand, Gawker should’ve thought twice before they ran this Hulk Hogan tape. There’s some argument, for instance, over whether Denton even knew that the Hulk Hogan tape was in Gawker’s possession and that they were thinking of running it until after it was posted, which is insane. The publisher of a media company should know before his website does something like that.

And so, hopefully, it makes them better at crossing their Ts and dotting their Is, but hopefully doesn’t make them unafraid. I’m glad The New York Times ran its expose on Harvey Weinstein or that the media reported on Bill Cosby, and it’s embarrassing and shameful that they didn’t do it earlier. But if you’re going to do those stories, you’d better make sure you’re bulletproof. And so that’s, I think, the balance that the media is going to have to figure out.

Brett McKay: After writing this book, curious, what do you think were the big takeaways you got from just about getting stuff done, strategy? Because these are ideas you’ve been thinking about a long time. So what were the big takeaways for you personally?

Ryan Holiday: One, I think that idea of patience. You don’t rush in. I say, “A fight breaks out, a conspiracy brews.” I think Thiel gives us a very interesting example here of just patiently waiting. And then, you’ve talked about John Boyd before in articles and on the podcast. He had this line, he said, “A fighter pilot always goes through the backdoor, never the front.” And what he means is that the fighter pilot looks for the weakness, looks for the opportunity. They don’t go head on. And I think that’s a strategic lesson here, too. The reason Thiel was able to win is that Gawker was overconfident and undefended in this area where they were taking risks that they shouldn’t have been taking.

And then, look, I think Thiel’s willingness to sort of get his hands dirty is a lesson, too. It’s very satisfying to go march in a protest or to donate money to a politician or a cause that you support or to sign a petition. But how effective are these things actually, and how often do you actually see if you have accomplished what you set out to accomplish? And so I think what Thiel did is he was like, “I’m going to solve this.” He’s like, “No one else is going to solve it. I’m going to take matters in my own hands, and I’m going to work really hard for a long time to solve this.”

And I think there’s some strategic lessons there, too. I’m relatively pro-Second-Amendment, but if you think we need gun control in this country, well, don’t just yell about it, but figure out what can actually be done. And that’s going to involve compromise. That’s going to involve collaboration. That’s going to involve patience. That’s going to involve the long game. If you think Donald Trump is evil, don’t just tweet about it, man. You’re going to have to work at removing him from office. Or if you think there’s a problem with suppressing free speech on college campuses, well, maybe you’ve got to find, like Thiel did, the perfect representative case that helps you set a precedent that you want to set that protects the people that you want to protect. And so on and so forth.

So I think that’s the real strategic lesson, which is that change is possible, but it’s not going to come just because you think that it’s right. It has to be made real.

Brett McKay: Well, Ryan, this has been a great conversation. Where can people go to learn more about the book?

Ryan Holiday: The book is Conspiracy. It’s on Amazon, everywhere books are sold. And you can go to my website at

Brett McKay: All right. Ryan Holiday. Thank you so much for your time. It’s been a pleasure.

Ryan Holiday: Thank you.

Brett McKay: My guest today was Ryan Holiday. He is the author of the book Conspiracy. It’s available on and bookstores everywhere. Also, check out his website, While you’re there, sign up for his reading list, email newsletters. One of my favorite newsletters I get. He shares what he’s been reading. Gotten a lot of recommendations from that. Also, check out our show notes at, where you can find links to resources where you can delve deeper into this topic.

Well, that wraps up another edition of The Art of Manliness Podcast. For more manly tips and advice, make sure to check out The Art of Manliness website at And if you enjoyed the show, you got something out of it, appreciate you taking one minute to give us a review on iTunes or Stitcher. It helps out a lot. If you’ve done that already, please consider sharing the podcast with a friend or family member who you’d think get something out of it. Really appreciate that. As always, thank you for your continuing support. Until next time, this is Brett McKay telling you to stay manly.

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