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

by Ryan Holiday

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.

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.

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.”

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.

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

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.

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.

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 line attributed to the management guru Peter Drucker is that culture eats strategy. It’s a truism that applies as much to conspiracies as it does to businesses. It doesn’t matter how great your plan is, it doesn’t matter who your people are, if what binds them all together is weak or toxic, so, too, will be the outcome—if you even get that far. But if the ties that bind you together are strong, if you have a sense of purpose and mission, you can withstand great trials.

Another maxim from Napoleon: “Never interrupt an enemy making a mistake.”

Thiel knew the importance of finishing. He had written it in Zero to One. “It is much better to be the last mover,” not the first mover.