Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue

by Ryan Holiday

Conspiracy entails determined, coordinated action, done in secret—always in secret—that aims to disrupt the status quo or accomplish some aim.

There is a moment in The Great Gatsby when Jay Gatsby introduces Nick Carraway to Meyer Wolfsheim, mentioning offhandedly that he is the man who fixed the 1919 World Series.

It was unbelievable to him then, as it is to us now, that a single person could have been responsible for changing the outcome of an event watched by some fifty million people.

He would remark years later that the revelation of the conspiracy that had thrown the series produced a profound change in his perspective about the world; it taught him never to trust in first appearances.

The truth, he says, is that “No one can carry out complicated plans. All parties and groups are fractious and bumbling.” We nod our heads in agreement. We shake our heads in disappointment.

Nick Denton, whom you will come to know in these pages, is a kind of freethinker who has always held that the things other people are afraid to say are precisely the ones that need saying most.

Peter Thiel, whom you will also come to know, has famously become associated with one question, which he uses in interviews and over long dinners: “What important truth do very few people agree with you on?”

There are no grand, towering bookcases befitting a billionaire in the New York City apartment of Peter Thiel, yet the space is defined by books. They lie in neatly arranged stacks of different heights on nearly every table. Colorful paperbacks and ancient hardcovers about economics, chess, history, and politics fill sets of small, modern shelves in the corners and against the walls.

Indeed, most of the pages in that book don’t matter for this story. Flip past them for now, you can read them another time. But there, buried between notes on how hereditary rulers lose their kingdoms and the effect of noises upon troops in battle, the title of chapter VI in book III stands out refreshingly in its simplicity. It is just one word: Conspiracies.

and something in Thiel allowed him to see past Machiavelli’s deceptive warnings against conspiracies and hear the wily strategist’s true message: that some situations present only one option.

It’s the option available to many but pursued by few: intrigue. To strategize, coordinate, and sustain a concerted effort to remove someone from power, to secretly move against an enemy, to do what Machiavelli would say was one of the hardest things to do in the world: to overthrow an existing order and do something new. To engage in a conspiracy to change the world.

They had been confident of victory for some time, having already experienced this moment, twice, in expensive mock jury proceedings. All that remained to be decided, as far as Thiel was concerned, was how much it was going to cost Gawker. The final tally? $115 million—$60 million of it for emotional distress.

can see the copy of Discourses over his right shoulder as he describes his personal war against Gawker in defense of a right he believes it threatened—privacy—and for what that privacy offers—the space to be peculiar, to think for oneself and to live as one wishes. The chef brings the first, second, and third courses as Thiel talks, revealing a painstakingly organized plot—the plan to reassert agency over a situation many believed was unchangeable, to protect something that most of his Silicon Valley peers had written off as an anachronism, but also to destroy an enemy and make the world a little bit closer to his vision of what it should be.

quick scan of Denton’s darkly lit apartment confirms that books define it, too. They are built into the architecture itself, lining each window, inset and running up to the thirteen-foot ceilings. Again, one book catches the eye. It’s a copy of the works of the Stoic philosopher Seneca, and it’s there precisely because of the conspiracy Peter Thiel had led against its possessor.

And because winning is typically preferable to losing, this book is about how one man came to experience what Genghis Khan supposedly called the greatest of life’s pleasures: to overcome your enemies, to drive them before you, to see their friends and allies bathed in tears, to take their possessions as your own.

“We live in a world where people don’t think conspiracies are possible,” Thiel would tell me. “We tend to denounce ‘conspiracy theories’ because we are skeptical of privileged claims to knowledge and of strong claims of human agency. Many people think they are not possible, that they can’t be pulled off.”

Machiavelli said that a proper conspiracy moves through three distinct phases: the planning, the doing, and the aftermath. Each of these phases requires different skills—from organization to strategic thinking to recruiting, funding, aiming, secrecy, managing public relations, leadership, foresight, and ultimately, knowing when to stop. Most important, a conspiracy requires patience and fortitude, so much patience, as much as it relies on boldness or courage.

“The beginnings of all things are small,” Cicero reminds us. What becomes powerful or significant often begins inauspiciously, and so, too, do the causes that eventually pit powerful forces against one another.

He calls it the “NASDAQ of Content,” but it’s closer to the millennial id. If the untapped energy of young people was his first great breakthrough, this is his second. The first offers the power of being heard, the second provides the power of reach and then of quantification—turning blogging into something you can win. How? By getting the most readers.

These are the essential beginnings of a conspiracy. First, a slight of some kind, which grows into a larger dissatisfaction with the status quo. A sense that things should be different, and will be different, except for the worse, if something doesn’t change. But then comes a second step, a weighing of the stakes. What if I do something about this? What might happen? What might happen if I do nothing? Which is riskier: to act or to ignore?

The Fifteen Decisive Battles of the World by Sir Edward Shepherd Creasy, the book he had read as he’d mulled his options over.

The epigraph to the chapter on the Battle of Valmy quotes Shakespeare: A little fire is quickly trodden out, Which, being suffered, rivers cannot quench.

You rush in to stamp out the sparks and end up fanning them into flames. This is the risk.

But a rich man has feelings, just like a poor man, worries and fears and opinions like a regular man. The difference is that the former has a way of thinking that he ought to spend his money doing something about them. And rich men don’t tend to like feeling small, feeling that same powerlessness they had once felt at a young age that had driven them to accomplish the things they had accomplished.

If someone asks him a question—say, about some controversial issue of the day—he does not simply react with an opinion, or pluck a conclusion from nowhere. Instead, he begins with, “One view of these things is that . . . ,” and then proceeds to explain the exact opposite of what he happens to personally believe. Only after he has finished, with complete sincerity and deference, describing how most people think about the issue, will he then give you his opinion, which almost always happens to be something radically unorthodox—all of it punctuated with liberal pauses to consider what he is saying as he is saying it. Even when he does describe his opinion, he prefaces it with “I tend to think . . .” or “It’s always this question of . . . ,” as if what he is about to tell you is simply capturing where his opinion falls the majority of the time when running a thought exercise on the topic, as if he is always in the process of deciding what he thinks. And this is simply the process for articulating what he thinks.

if there is a 20 percent chance that Gawker will cost me $1 billion, then it makes perfect sense to spend up to $200 million trying to prevent that from happening. Negative expected value—it’s a calculation Wall Street guys make every day.

Machiavelli said that conspiracies were weapons of the people. Only princes could afford to send an army against another army, he observed, but a conspiracy is available to every man. Which is why it is usually the desperate who turn to conspiracy and why the powerful fear them so much.

It’s the logic of two campers and the bear—you don’t need to be faster than the bear, just faster than the other camper.

Eddie Hayes. In addition to being a capable lawyer, Hayes also served as literary inspiration to the author Tom Wolfe, was a friend of the late Andy Warhol, and is a talented actor who played Robert De Niro’s lawyer in Goodfellas, as well as De Niro’s attorney in real life. He is a notorious and well-connected “fixer” who has been a confidant and problem solver for actual mob bosses, celebrities, artists, and politicians. His infamous slogan, “I can get ya outta anything!,”

They act on motives. It’s when we begin to see that something deeper than self-interest is at play, that they cannot be made to see reason, that we begin to despair of ordinary means of resolution.

One of the most profound intellectual influences on Peter Thiel is a French thinker named René Girard, whom he met while at Stanford and whose funeral he would eventually speak at in 2015. Girard’s theory of mimetic desire holds that people have no idea what they want, or what they value, so they are drawn to what other people want. They want what other people have. They covet. It’s this, Girard says, that is the source of almost all the conflict in the world. Is this not the source of the tension between Denton and Thiel, not because they are so different, but because they are so similar?

Denton would explain in an interview with Playboy that this kind of radical honesty was partly a defense strategy: “The easy way to insulate yourself against snark is to preemptively snark. Snark before anybody else does. That’s a kind of classic defensive humor. Make fun of yourself before somebody else does and lower everybody’s expectations. . . . I lower everyone’s commercial expectations. ‘Oh, nothing to see here. There’s no business here.

Peter Thiel’s friend, the mathematician and economist Eric Weinstein, has a category of individual he defines as a “high-agency person.” How do you respond when told something is impossible? Is that the end of the conversation or the start of one? What’s the reaction to being told you can’t—that no one can? One type accepts it, wallows in it even. The other questions it, fights it, rejects it. This choice defines us. Puts us at a crossroads with ourselves and what we think about the kind of person we are.

“Anyone who is threatened and is forced by necessity either to act or to suffer,” writes Machiavelli, “becomes a very dangerous man to the prince.”

Machiavelli writes that a conspiracy without any coconspirators is not a conspiracy. It’s just a crime. This is also basic legal principle. If you kill someone by yourself, in the heat of the moment, it’s murder. If you meticulously plan it with someone else beforehand, that’s conspiracy.

In his definitive book on the subject of strategy, Lawrence Freedman writes that “combining with others often constitutes the most strategic move.” By definition, the first move in the act of a conspiracy is the assemblage of allies and operators: your coconspirators. Someone to do your bidding, to work with you, someone you can trust, who agrees with you that there’s a problem, or is willing to be paid to agree with the sentiment that it’s about time someone, somebody did something about this. Each hand doesn’t need to know what the other is doing, but there needs to be more than one set.

Thus, Thiel’s vague idea to do something about Gawker is concretized into conspiracy on April 6, 2011. It began unremarkably, when Thiel traveled to Germany to speak at a conference and had dinner with a student he’d met on a tour of a university a few years before. Peter arrives, driven in a black S-class Mercedes, the same model he has idling outside with a driver, twenty-four hours a day, seven days a week, wherever he is in the world. From the hotel emerges a short, fit young man of indiscernible origin. Aside from his Ivy League education, the young man has at this point achieved next to nothing. But Peter attracts these types—mostly men early in their potentially ascendant careers—and puts them to good use: investing in them, giving them advice, placing them in start-ups, assigning them important roles in his operations. This specific young man in Berlin we shall refer to as Mr. A, the pseudonym that almost everyone involved in the conspiracy refers to him by.

Mr. A is not just young, but ambitious, ambitious in a way that makes observers slightly uncomfortable, that makes him stand out even among the cadre of upstarts in Peter’s orbit. It’s not fame he wants, or money either, or even to create the next big tech company. He read Machiavelli at thirteen. He...

In contrast, Mr. A is ambitious, but it’s paired with self-confidence, social adeptness, and a clear sense of what Thiel wanted. Even so, the prospect of meeting with Thiel is intimidating: his stomach churning, every nerve and synapse alive and flowing. He’s twenty-six years old. He’s sitting down for a one-on-one evening with a man worth, by 2011, some $1.5 billion and who owns a significant chunk of the biggest social network in the world, on whose board of directors he also sits. Even if Thiel were just an ordinary investor, dinner with him would make anyone nervous. One quickly finds that he is a man notoriously averse to small talk, or what a friend once deemed “casual bar talk.” Even the most perfunctory comment to Thiel can elicit long, deep pauses of consideration in response—so long you wonder if you’ve said something monumentally stupid. The tiny assumptions that grease the wheels of conversation find no quarter with Thiel. There is no chatting with Peter about the weather or about politics in general. It’s got to be, “I’ve been studying opening moves in chess, and I think king’s pawn might be the best one.” Or, “What do you think of the bubble in higher education?” And then you have to be prepared to talk about it at the expert level for hours on end. You can’t talk about television or music or pop culture because the person you’re sitting across from doesn’t care about these things and he couldn’t pretend to be familiar with them if he wanted to.

The butterflies settle. The conversation has wound itself down naturally and now there is nothing left but for Mr. A to seize the moment. This moment that few get. The chance for a pitch that can change your life. There is something popular with ambitious people called the “briefcase technique.” You don’t show up to a meeting with a few vague ideas, you have a full-fledged plan that you take out of your briefcase and hand to the person you are pitching. Even if nothing comes of this plan, the person on the other side is knocked over by your effort, so impressed by the unexpected certainty that they cannot help but see your usefulness to them. Mr. A unlocks that figurative briefcase on the table: “Okay, I know what you think about Gawker, here’s what I am proposing. . . .”

Mr. A’s proposal is more than just an idea, it’s a comprehensive, structured plan: he has researched some names, he has a timeline and a budget. Three to five years and $10 million.

But Mr. A is different. Multiple people, describing him to me, borrowed Robert Caro’s description of LBJ as a young man: a professional son. Lyndon Johnson knew how to identify a susceptibility for protégés in older successful people and then make himself into theirs. Mr. A had that. In fact, he would self-identify with the label of professional son, too.

begins. It would be a mistake to confuse Peter’s pondering Socratic-ness for uncertainty. His mind, for all its detours and considerations, ultimately meanders toward precision, the kind that calculates down to the ten-thousandth decimal point in ordinary conversation. He is the kind of man who might make a multimillion dollar bet without hesitation. It’s only if you ask him a question about an arcane point in Russian literature that you get the long pause of consideration. He wouldn’t want to just spout off. But if he thinks he has some deep idea about human nature, about the market, he’ll go all in.

At a certain point in every conspiracy each participant realizes that proceeding will require of them something that little else in their life ever has. What that is isn’t willpower or resources or creativity, but instead a certain hardness and viciousness—the hard, unforgiving utilization of power or even violence against other human beings.

While Machiavelli never said—as some might claim—that we must lose that part of ourselves altogether in the pursuit of power, he did say that for the prince who wishes to remake the world to his liking, the natural impulse to be kind, forgiving, and empathetic must temporarily be suppressed. This is not an easy thing to do, even in the face of overwhelming necessity.

By 1939, Franz Halder, a German general, had taken to carrying a pistol so that when he was in the room with Hitler, he might assassinate him. But he could never pull the trigger. He could not reconcile how he could take up as “human being and a Christian to shoot down an unarmed man.” In fact, many German generals knew that someone should do it, they wanted it to have been done, but they could not do it themselves . . . because it was unethical. Hans Oster, himself a dogged German conspirator against Hitler, would despair, “We have no one who will throw the bomb in order to liberate our generals from their scruples.”

The man believes he has considered any and all reservations, but only when it looks and feels like it will actually happen—when he stands in the same room with the enemy, forced to really do the deed that had been only theoretical before—do the real concerns hit him. Many are stopped in their tracks in that moment, perhaps to the benefit of all involved.

He had thought about bringing about Gawker’s destruction via legal and ethical means, but to think and to do are always different things.

Thiel’s default state is to embody contradiction. Doing so is what makes him such a brilliant investor, considering each trade and investment anew from a dozen perspectives, seeing what others aren’t able to see and doing it on a regenerative basis. A friend would say that “Peter is of two minds on everything. If you were able to open his skull, you would see a number of Mexican standoffs between powerful antagonistic ideas you wouldn’t think could be safely housed in the same brain.”

His style as a CEO had been deftly adapted to this quirk. At PayPal, as the CEO, Peter was once required to make the unpleasant decision about whether the company should conduct transactions on behalf of porn companies. As a normal human being, as a Christian, he can see one point of view. As a libertarian, he can just as easily articulate the other, as Nick Denton did when he started Fleshbot: give the people what they want. Thiel’s solution to this standoff was simple. He called a staff meeting to let the employees decide. In deference to their feed...