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

by Ryan Holiday

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 ...

This choice def...

One quickly finds that he is a man notoriously averse to small talk, or what a friend once deemed “casual bar talk.” Even the most perfunctory comment to Thiel can elicit long, deep pauses of consideration in response—so long you wonder if you’ve said something monumentally stupid.

seize the moment. This moment that few get. The chance for a pitch that can change your life. 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...

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...

Robert Caro’s description of LBJ as a young man:

a professional

Lyndon Johnson knew how to identify a susceptibility for protégés in older successful people and t...

The professional son understands what every father wants—a progeny worth his time, someone to invest in,

someone who can further his legacy. The professional father wants to see his greatness given a second body—a younger one, with more energy, with the benefit of his hard-won experiences.

Rooted in every conspiracy is often shared loneliness, a smoldering frustration or bitterness. Of not being listened to. Of the world not understanding.

Two people come together and this smoldering becomes the small flicker of a flame for the first time. Someone shares this with me. I am not alone.

Two is more than one and can become three, fou...

“one definition of evil is to fail to recognize the humanity in the other: to see a person as an object or tool, something to be put to use.”

The image of Silicon Valley is that the start-up comes together quickly, from idea to minimum viable product to world-changing business in a montage of exciting steps.

In truth, like conspiracies, it takes a little longer. The path can be meandering.

This compartmentalization is key to a conspiracy. Not everyone can be in charge.

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.

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.”

We are often taught that successful strategy is a matter of boldness,

but it has also always been the case that it’s as much a matter of patience and due diligence as it is of noticeable action.

it had taken four full years since then to conceive of what kind of response might even be

possible. Thiel founded and sold PayPal in considerably less time.

The target, Nick Denton, is not a patient man.

Most entrepreneurs aren’t. Most powerful people are not.

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 user of special means must scorn the obvious—ignore the conventional wisdom and voices from the sideline.

“There are things that were very tempting, an eye for an eye, tooth for a tooth. Retributive justice,”

“But I think those would’ve ultimately been self-defeating. That’s where you just become that which you hate.”

we decided very early on we would only do things that are totally legal, which is a big limitation. But it forced us to think really hard about what to actually do,”

As they had decided from the outset, Thiel would not be a claimant in any of these cases and, equally early, Thiel claimed to be interested only in litigating and funding claims that could be expected to survive appeal, were they fortunate enough to reach a positive verdict.

Libel and defamation cases are notoriously hard to win in the American legal system.

That was one of the benefits of his patience: he wasn’t angry anymore, he didn’t need people rallying to his side.

He wasn’t thinking of revenge, but of accomplishing something that would stick.

Just because you decide to operate along a line of interior ethics, however,

doesn’t mean you’re stupid about it. You don’t have to disclose your intentions, for instance. No one said the fight needs to be fair, or that punches should be pulled.

The search for weakness remains. The exploitation of that weakne...

The degree to which one succeeds or fails in this endeavor tends to determine not only how well one sleeps at night, but also how the public ultimately views who was in the right.

Ethics don’t win the war, but they do help keep the peace.

It wasn’t just a question of which strategy might actually win, it

was also figuring out which one could actually do real damage.

as Denton would himself admit to me later, free speech is sort of a Maginot Line. “It looks formidable,” he said, “it gives false confidence to defenders, but there are plenty of ways around if you’re nimble and ruthless enough.”