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.

The instinct to curl into a ball. The hope that this will go away. The anger at the unfairness of it, the randomness of it, the needless im-politeness of it. The sense that someone was doing this for sport, as part of a game. That someone had this power and wielded it so capriciously . . . It is from these kinds of thoughts that conspiracies are born.

In a fight, one responds to a punch by throwing a punch. In a conspiracy, one holds their punches and plots instead for the complete destruction of their antagonist, while often intending to escape with knuckles unbloodied and untraceable prints. Fights break out. Conspiracies brew.

You were driven to entrepreneurship because it was a safe space from consensus, and from convention.

Thiel saw Gawker not so much as a revolution but as anarchy masquerading as a movement.

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.

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.”

“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.”

By definition, the first move in the act of a conspiracy is the assemblage of allies and operators: your coconspirators.

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.

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.

That they’d actually made an enemy, that this wasn’t some theatrical production, did not yet compute.

The downfall of all ruling power?

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

Liddell Hart would compare a strategic plan to a tree, saying that a healthy one has multiple branches, and that a plan with a single branch is but a barren pole. A tree with a single branch is not a tree at all, it’s a gallows.

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.

Opposite of advice from The Prince?

Gawker’s growth would make it precisely what it criticized: powerful, unaccountable, unaware.

A rare mutual friend of Thiel’s and Denton’s would tell me that this was Gawker’s main weakness, one that was inevitably going to cause a fatal problem, if not from Thiel then from someone, eventually. There were no competent managers or operators in the company.

“A wound to the reputation not only does not heal, but grows deeper every day which goes by,” E. L. Godkin wrote in Scribner’s Magazine more than 125 years ago. He wrote this about the rise of the mass newspaper, in an article that would inform Justice Brandeis’s “Right to Privacy” argument.

discretion is the responsibility of freedom, the obligation that comes along with rights.

Doesn’t matter if you have a good or bad case. You’re going to run out of money.’ They made that argument against Hulk Hogan,” Thiel says. “‘You will get no justice because you have no money.’”

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

Machiavelli would say that a coup or a conspiracy can succeed only if the will of the people is on its side.

“If you can convince a jury in Tampa that this is not the way the technological future should look,” Peter says to me, “they can tell history to stop.”

He had proven that “nothing you can do about it” is just what people who don’t want to do anything about it like to say to make themselves feel better about their inaction.

Scipio Africanus, the general who defeated Hannibal, would say that an army should not only leave a road for their enemy to retreat by, they should pave it. The Romans had a name for this road, the Gallic Way.

“The idea of a conspiracy,” Thiel would say to me, “is linked with intentionality, with planning, working towards longer-term goals. In a world where you don’t have conspiracies maybe also those things disappear.”

I said in the introduction that we might live in a world of too few conspiracies, not too many. We have plenty of opinions—plenty of histrionic complaints about how terrible and awful and stuck we are—but not enough people with the patience, coordination, and ambition to do anything about

In ancient times it was the foolish sophists who believed that every problem could be talked through, that the logical, obvious, and right thing would simply come about if explained well enough. It’s the realists who know that this isn’t how things actually work, who know that realpolitik is how things actually get done.

If you want to have a different world, it is on you to make it so.

Nick would tell me, in one of our almost weekly chats that I had come to enjoy so much, that the lesson he had learned was that free speech was not necessarily noble by itself, that it needed to be paired with compassion and understanding.