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

by Ryan Holiday

Our tendency to shy away from this truth creates a profound ignorance of how things really work,

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

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?”

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.

Seneca is the author you read when your life’s work has been destroyed, as Denton’s undeniably has.

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.

Peter Thiel Is Totally Gay, People.

Gawker’s first editor, Elizabeth Spiers, was paid $2,000 per month for twelve posts a day, seven days a week. Her job was to mock the club of New York elites she had never been invited to join. Her job was to, with a kind of humorous contempt that’s come to be called snark, dismiss people and institutions as laughably unimportant, even as, in writing about them, she was in fact admitting how important they actually were (and that perhaps, deep down, she’d like to join them someday). Denton had a knack for recruiting talent like her, and for cultivating their voices as he did with Spiers and, eventually, Owen Thomas.

He calls it the “NASDAQ of Content,” but it’s closer to the millennial id.

Never fight a battle against someone who buys ink by the barrel. It’s easier to just let the whole thing go.

“two bodies in space, repelling and attracting, forever swinging about each other in sickening orbit from which neither could escape”?

Gawker Media’s reputation as the site that would “say the things other people wouldn’t say.” And with that we would have a casus belli.

As Cicero said, the beginnings of all things are small,

There is an old Scottish motto: nemo me impune lacessit. No one attacks me with impunity.

Fights break out. Conspiracies brew.

In 2003, Thiel registered a company called Palantir with the Securities and Exchange Commission.

The Fifteen Decisive Battles of the World

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.

The kind of mathematical equation someone like Peter might consider would look something like this: 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.

Twenty-five hundred years ago, Thucydides would say that the three strongest motives for men were “fear, honor, and self-interest.” Fear. Honor. Self-interest. All covered. Which is the truest of them for Thiel? Does it matter? Someone had begun to think seriously that something needed to be done and believed that he might be the person to do it.

After the series of famous Washington Post stories by Bob Woodward and Carl Bernstein about the Watergate scandal in 1972, President Nixon not only fails to destroy the paper’s publisher, Katharine Graham, he destroys himself in the process and officially ends the traditional deference between the press corps and the presidency. Barbra Streisand sues to remove a picture of her house from the internet, and not only does she lose, but more people see the photo than otherwise would. It is a behavioral phenomenon that gets dubbed, fittingly, the Streisand Effect and has stood as a warning since: the media always wins in the end.

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.

It is always revealing to see how a person responds to those situations where he’s told: “There’s nothing you can do about it. This is the way of the world.” 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.”

There is a scene in the movie The Assassination of Jesse James by the Coward Robert Ford. At the beginning, in the woods, Robert Ford, played by Casey Affleck, illustrates this phenomenon. He thinks the outlaw Jesse James is a great man. He thinks that he, himself, is a great man, too. He wants someone to recognize that in him. He wants someone to give him an opportunity—a project through which he can prove his worth. It just happens that Frank James would size the delusional, awkward boy up in the woods outside Blue Cut, Missouri: “You don’t have the ingredients, son.”

Mr. A takes a certain pride in this little lie, the use of the word individuals instead of individual. Throughout the conspiracy, he would try to refer to Thiel as “my principals”—implying that there was some consortium of backers involved. Mr. A believed it was much less likely that Harder would demand to speak to them, to go over the head of this twenty-something, if it was much less clear whom he would be going to. And finally, the plurality of benefactors gave Mr. A a certain duplicative freedom. If money was slow, he could blame the delay on coordination problems. If he was unsure of something, he could buy time to deliberate. He could use the illusion of a group for pressure, as cover for different opinions, for expressing doubts, and for anything else he needed.

This compartmentalization is key to a conspiracy. Not everyone can be in charge. Mr. Harder works for the clients whose bills are paid by Mr. A, who works for Mr. Thiel (while Mr. Harder does not know who Mr. Thiel is). Not everyone can know every element, or give their opinion on all of it. Not every decision can be explained or needs to be. At some point, some people’s job is just to answer the phones, to press the buttons, to shred the documents, to argue in court, because that’s what they are paid to do. They are paid to do a job.

In the search for collaborators, hunger is an essential qualification. While it’s dangerous to conspire with people who have a lot to lose, you can’t conspire without someone who is afraid to bet on themselves, who isn’t willing to take a big stake on something that very well could fail. Where these two traits overlap there is often a sweet spot: the man or woman who has something to prove and something to protect, the strong sense of self-belief coupled with that killer instinct. It’s these two, Mr. A and Charles Harder, one much older than the other, who will do the bulk of the work and both walk this delicate balance of hunger and competence. In the business of bringing down Gawker, Mr. A was the president, Harder was the CEO, and Thiel the majority shareholder who expected his men to mind his money and find the returns he is after. This is the model he likes to operate. Early in the two companies he cofounded, PayPal and Palantir, Thiel would install strong CEOs and leaders. He relies on what might be called the plenipotentiary model—empowering trusted, skilled people on his behalf to execute the bold vision he has created.

A start-up is, in Peter’s definition, “a small group of people that you’ve convinced of a truth that nobody else believes in.”

“With patience and resources,” Mr. A would come to say often on his weekly calls with Peter, “we can do almost anything.” Tolstoy had a motto for Field Marshal Mikhail Kutuzov in War and Peace—“Patience and Time.” “There is nothing stronger than those two,” he said, “. . . they will do it all.” In 1812 and in real life, Kutuzov gave Napoleon an abject lesson in the truth of that during a long Russian winter.

To begin you must study the end. You don’t want to be the first to act, you want to be the last man standing. History is littered with examples of those who acted rashly in pursuit of their goals, who plunged ahead without much in the way of a plan, and suffered as a result.

The great strategist B. H. Liddell Hart would say that all great victories come along “the line of least resistance and the line of least expectation.” John Boyd, a fighter pilot before he was a strategist, would say that a good pilot never goes through the front door. He wins by coming through the back.

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. There is no other way to say this.

It has been the great collective self-deception of Silicon Valley, and perhaps of our age, that a person can engage in aggressive “disruption” of existing industries while pretending that they are not at least similar to the ruthless capitalist barons of the previous century, that there is not a drop of Carnegie or Rockefeller or Vanderbilt DNA in the whole business. Peter Thiel didn’t have to personally fire the bank tellers that he put out of a job at PayPal. He wasn’t deliberately driving down the stocks of the newspapers in order to boost the stock of Facebook, even if that was the ultimate effect. He never had to personally sign off on any drone strikes or SEAL Team Six raids at Palantir, even if the data his company handed off made them possible. All the nasty stuff was far from view. The start-up CEO can tell himself that he is a good guy, because from his vantage point he is.

The Count of Monte Cristo would put it better: “What a fool I was not to tear my heart out on the day when I resolved to avenge myself!” Ah, but what dangerous business this is. This artificial hardening is a dangerous crossroads, a bargain with our primal forces that not everyone escapes or can emerge from with clean hands. William James knew that every man is “ready to be savage in some cause.” The distinction, he said, between good people and bad people is “the choice of the cause.”

choose your enemies wisely, he had been told, because you become just like them—but plunged ahead nonetheless, with a piece of his heart torn out.

Caesar, hoping simply to stand for election to consul, is unfairly ordered by the Senate to disband his army and return to Rome. On January 10, 49 BC, he pauses on the banks of the Rubicon, utters those famous words Alea iacta est—“the die is cast”—and crosses the river with his army. He is marching on his own country.

It is here, for the first time, in March 2012, that all our characters begin to intersect in the way that will move this conspiracy from planning toward action.

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

It’s the drive where you hit every red light. The project where everything seems to go wrong, at the same time.

It is the nature of conspiracy. If it was easy, everyone would do it. Fate rarely conspired to help conspirators—and if it was on their side, why were they forced to do all this sneaking around then? No, fate sends to the conspirators of the world the best of its Murphy’s Law and entropy and crises of confidence.

And so the essential trait of the successful man is not only perseverance but almost a perverse expectation of how difficult it is going to be. It is having redundancies on top of redundancies, so you can absorb the losses you eventually incur. One must not just steel one’s heart but also one’s spirit so that there is no such thing as an obstacle—just information. The earlier you spot and anticipate setbacks, the less demoralizing they will be. We want things to be easy. We want them to be clean. They rarely are. Napoleon’s dictum for the general-in-chief is that he “must not allow himself to be elated by good news or depressed by bad.” In the course of any campaign there will be plenty of both. A conspiracy meets with more setbacks than successes. It’s rolling the dice—making a decision, knowing that unforeseen issues will come up. Lots of them.

The early setbacks, coming one right after another, would also contribute to the growing confidence of their opponent. Judge Whittemore’s repeated rulings had given Gawker the sense that the law was overwhelmingly on its side. Gawker’s confidence, as it had been since its beginnings as a company, tended to bleed over into contempt. Its early belief that Judge Campbell had no power over them, that they could disregard her rulings, would undoubtedly make Gawker less sympathetic to her in the years of motions to come. Finally, it was no small thing that the media coverage had been favorable to Gawker and its chances. Far away from Florida, Nick Denton would be surrounded by peers, even competitors, who were convinced that this case was open and shut, that it was only a matter of time before it resolved in his favor, and that in the meantime it didn’t need to be taken seriously.

But the past is no indicator of the future—ask the fattened Thanksgiving turkey or the proverbial man stacking straws on a camel’s back. It’s Rome telling itself that no one could ever cross the Alps. Then one day Hannibal appears in Italy with his elephant. Shit, they can do that?

There were many moments in World War II when it looked like Hitler’s unshakable faith in Enigma would finally and correctly be shaken. Each time, the Allies must do what they can to keep the ruse alive, to keep the secret safe. How many ships do we allow the U-boats to sink? How many can we save? What kind of defense can we give the city of Coventry, knowing a terrible bombing is coming? What are we willing to sacrifice of ourselves to keep this edge?

In every conspiracy, there is temptation to talk, especially as you near your goal. The weight of silence and deceit begins to weigh on the participants. You might be sitting at a dinner with all your friends. Each speaks with such ease about their recent successes, each is able to talk freely and share their opinions. Yet you can say nothing. The conspiracy has consumed countless waking moments, produced a number of successes you want to brag about, and probably even more difficulties that you could desperately use support and reassurance on, but you don’t say a word.

And so secrets aren’t necessarily forever. You have to live with it coming out at the end.”

This is not a pretty image, relentlessly pursuing an adversary until he begins to stumble from exhaustion. But it must be this way. The enemy is weaker when plunged into what the statesman Demosthenes described as a “welter of confusion and folly.” A single attack allows resistance to be concentrated, but two or three or four put the enemy between the horns of a dilemma, choosing between equally subpar options. Or, blindly hoping to avoid one attack, he falls headfirst into the other without even knowing. Nero poisoned a suspicious, paranoid rival not by putting poison in his food, because each dish was tested by an attendant. Instead, he arranged for the man to be served a harmless but very hot bowl of soup. It was in the cold water, requested and poured in by the man himself, that deadly poison was delivered. Without this suppressive cover, the countermove is too obvious: when you know where the enemy is going, you go there and block them.

Pressure. Pressure. Remorseless pressure.

Being feared, Machiavelli says, is an important protection against a conspiracy. The ultimate protection, he says, however, is to be well liked. Not simply because people who love you are less likely to want to take you down, but because they are less likely to tolerate anyone else trying to, either. If a prince guards himself against that hatred, Machiavelli writes, “simple particular offenses will make less trouble for him . . . because if they were even of spirit and had the power to do it, they are held back by the universal benevolence that they see the prince has.”

“At some point the word ‘strategy’ becomes a euphemism for procrastination. A lot of different plans, a lot of different plans, and they will take a long time and you never—” and there he cut himself off as he so often does. So I’ll finish it for him.