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

by Ryan Holiday

A young lieutenant colonel in the U.S. Army named Dwight Eisenhower eagerly followed the game as the scores came in via telegram, and like everyone else, never suspected a thing. 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.

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.

“The beginnings of all things are small,”

Gawker’s first editor, Elizabeth Spiers, was paid $2,000 per month for twelve posts a day, seven days a week.

Previous generations of writers came to New York City with a dream. This generation came with a bone to pick—for

A New York Times writer would later dub this ethos the “rage of the creative underclass.” A Gawker headline captures it better: “It’s OK to Be a Hater Because Everything Is Bad.”

turning blogging into something you can win. How? By getting the most readers. With what? That’s for you to decide.

And it isn’t scoops that the sites were looking for, it was scalps:

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

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

He venerated privacy, in creating space for weirdos and the politically incorrect to do what they do. Because he believed that’s where progress came from.

deranged individual who starts companies. You’ve created cryptocurrencies designed to replace the U.S. monetary system that somehow turned into a business that helps people sell Beanie Babies and laser pointers over the internet and ends up being worth billions of dollars. Where others saw science fiction, you’ve always seen opportunities—for real, legitimate business. You’re the kind of person who is a libertarian before that word had any kind of social respectability. You’re a conservative at Stanford. You’re the person who likes Ayn Rand and thinks she’s something more than an author teenage boys like to read. You were driven to entrepreneurship because it was a safe space from consensus, and from convention. How do you respond to social shaming? You hate it. How do you respond to petulant blogs implying there is something wrong with you for being a gay person who isn’t public about his sexuality? Well, that’s the question now, isn’t it?

There must have been a way that Gawker reminded Thiel of the self-righteous people he had been railing against since he was a conservative polemicist in college: the people who claim the moral high ground, who claim to be about freedom of choice, but who bully everyone who doesn’t choose their way of freedom.

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

Even when he does describe his opinion, he prefaces it with “I tend to think . . .” or “It’s always this question of .

In May 2007, an erroneous report by Engadget, a Gizmodo competitor, temporarily knocked $4 billion off the market cap of Apple.

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.

But if he looked beyond Gawker’s potential cost to him in dollars to the cost to society in total, the math changed.

If the continued effect of Valleywag is that it makes Silicon Valley 1 percent less ambitious, what is that cost?

For every dollar in revenue that Gawker makes, how much economic value is it destroying, for Peter and for other people?

Through Choire and Hayes, Thiel is also introduced to Ryan Tate, who in 2009 became the editor of Valleywag. At a wine bar in Palo Alto, Peter Thiel sits down with Tate and supposedly says, “See, I do negotiate with terrorists.”

“It’s super unclear how to negotiate with sociopaths,” Thiel said.

They are perhaps the only two people on the planet, one person who had studied them closely observed to me, who might actually identify as plutocrats.

Girard’s theory of mimetic desire holds that people have no idea what they want, or what they value, so are drawn to what other people want. They want what other people have. They covet.

One thing I learned from him was to keep all your shit out, in public, and ultimately, that’s a protective shield.”

“The easy way to insulate yourself against snark is to preemptively snark.

‘Oh, nothing to see here. There’s no business here. This thing has the revenue of a hamburger stand. We have no journalistic ambitions. If we ever commit journalism, it’s by accident.’”

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.

“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 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.

It was paramount to Peter that he not be associated with the plot in any way.

“Gawker’s modus operandi was to have hurtful speech with no repercussions because they believed that the court system didn’t work, that the people had no access to it,”

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.”

Peace—“Patience and Time.” “There is nothing stronger than those two,”

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.

The jungle fighter doesn’t choose guerrilla warfare from an array of strategies laid out in some glass-walled conference room.

Peter seems to have a preternatural ability to sense which lever to pull, what angle is the best approach, and it’s almost always something radically different from what your average person would select.

The edge here is believing that the strategy every other would-be Gawker foe had dismissed as too obvious or too difficult is actually possible.

It only seemed difficult because no one had ever truly committed to trying, nor had any individual actually had the resources to test its simple hypothesis.

“We don’t need to really worry about those people very much, because since they don’t think it’s possible they won’t take us very seriously. And they will not actually try to stop us until it’s too late.”

It’s Thiel’s investment strategy: with the right conditions, a little boldness will make much more progress than timidity will ever protect. So here Thiel finds his first edge: a willingness to try. To prove something in the court of law, to a jury.

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.”

Jezebel would define its views more clearly in outrage when a rival blog published a controversial story about someone’s sexuality: “Don’t out someone who doesn’t want to be out. The end. Everyone has a right to privacy. . . .” Except Peter Thiel, and now Terry Bollea, apparently.

“The problem with the Silicon Valley,” as Jim Barksdale, the former CEO and president of Netscape, once put it, “is that we tend to confuse a clear view with a short distance.”

Here, too, like the founders of a start-up, the conspirators have smacked into reality. The reality of the legal system. The defensive bulwark of the First Amendment. The reality of the odds. They have discovered the difference between a good plan and how far they’ll need to travel to fulfill it. They have trouble even serving Denton with papers. Harder has to request a 120-day extension just to wrap his head around Gawker’s financial and corporate structure. This is going to be harder than they thought.

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.”

setbacks with a greater degree of equanimity. “If you think of what you’re doing too probabilistically where you have all these different steps, and there’s a chance that all these steps fail, then the conspiracy is very complicated, like a Rube Goldberg contraption,

“What Mr. A convinced me of in 2011 was that this is not a statistical concatenation of probabilities—it was that if we simply executed on a few of these things correctly you would win.”