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

by Ryan Holiday

In real life, the 1919 World Series was fixed not by Wolfsheim, but with great skill and audacity by Arnold Rothstein, a Jewish gangster. 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...

This is a book for a world that has come to think like Nick Carraway, riding in disbelief through life on the wake of conspiracies we won’t believe until we see, unable to comprehend why they happen and who makes them happen.

This ignorance of how things really work is depressing to me. Because it opens us up to manipulation. It closes us off from opportunities to produce fruitful change and advance our own goals. It is time to grow up.

“What important truth do very few people agree with you on?”

Perhaps we have too few conspiracies, not too many. Too little scheming, rather than too much.

What would happen if more people took up plotting, coordinating how to eliminate what they believe are negative forces and obstacles, and tried to wiel...

We could almost always use more boldness, and l...

We could use less telegraphing of our intentions or ambitions and see what secrecy, patience, and planning might accomplish. We could use a little more craziness and dis...

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.

Every conspiracy is a story of people.

The question of justice is beside the point; every conqueror believes their cause just and righteous—a thought that makes the fruits taste sweeter.

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 re...

What becomes powerful or significant often begins inauspiciously, and so, too, do the causes that eventually pit powerful forces against one another.

A friend would say that Peter burned to be the best technology investor in the world. To insert “gay” into that, to be seen as the best gay technology investor, seemed artificially limiting. Like it was cheating him of something he was desperate to earn.

he was, above all, a quiet, private person.

When one considers Thiel’s burning ambitions against this backdrop, and the potential for this Valleywag story to be the first thing to broadly define him outside the Valley, one might better understand Thiel’s reaction

A little over ten years into Gawker’s run, its revenues would be nearly $40 million a year and the sites would have more than 40 million readers a month.

“As a publishing entrepreneur who built an operation out of nothing, I had to go where the energy was,”

That energy was mostly the

energy of disillusioned youth, of outsiders criti...

The existentialists spoke of

ressentiment,

or the way that resentment creates frustration which fuel...

Gawker would revel in ressentiment, of its writers and readers. Like most movements that harness the power of an underappreciated class, the env...

but you could not argue that the results were not also entert...

Especially when combined with financi...

What Denton did, in effect, was turn writing, social commentary, and journalism into a video game. Writing wasn’t a craft you mastered. It was a delivery mechanism.

The people and companies you wrote about, like Peter Thiel, weren’t people, they were characters on a screen—fodder for your weekly churn.

And the people you got to read this writing? They were points. The score was right t...

And it isn’t scoops that the sites were looking for, it was scalps: who can we get, who did something stupid, what are other people afraid to say, and who are they afraid to say it about?

If a piece didn’t go hard enough, if there were rumors the reporter wanted to talk about but couldn’t justify even with Gawker’s thin standards, there was always the comments section to push the story from behind—or the bottom, as it were—and drum up tips and speculation and titillation that might lead to more attention.

It was all great fun for him, for his writers. Why wouldn’t it be?

Especially when the old guard yells at you, and you

are the type who takes that as a sign you’re doing ...

it cannot be said that readers didn’t love Gawker. There was a unique freeness to what Gawker wrote, a kind of raw unfiltered honesty, an exaggerated way of telling the truth.

The writers said the things that people thought in private—they fulfilled their wishes.

the site would be dedicated to publishing “open secrets”—the things that are said between the knowing in private but denied to the rest of the world in public.

Facts. Details. Secrets. Exactly the kinds of things Peter

Thiel considered private, Denton believed belonge...

and both agreed there was power in con...

For his bravado, Nick Denton was an incisive reader of other people.

What he knew was that most people did not have the stomach—or the cash—to actually take it very far against a media outlet.

They would pick people who seemed attracted to publicity and write about them over and over again as the tips came in.

Every freelancer is on a kind of extended job interview, dreaming of a pathway to salary and benefits, and most importantly, trying not to get fired.

Perhaps Peter should have understood this, that it wasn’t about him. Perhaps he should have had thicker skin. But he didn’t.

What he did understand and what he did believe was that once these articles had started, they probably weren’t going to stop.