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

by Ryan Holiday

The great strategist B. H. Liddell Hart would say that all

great victories come along “the line of least resistance and the line of least expectation.”

Contained within Gawker’s hundreds of thousands of articles, Mr. A was sure, were the seeds of destruction.

They were looking for Al Capone’s tax evasion,

a legal mistake that no one else had bothered to enforce, something dismissed potentially even by the person on the other side of the story.

Not just the kinds of cases that a judge would allow to proceed, but ones that would resonate with a jury of ordinary people in whatever jurisdiction they might find themselves.

It was obvious, too, that this process was accelerating, which was not

exactly a bad thing if you were sitting on the outside looking for a weakness that could be exploited, or hoping for your enemy to make a fatal mistake.

It was almost a matter of fact that this could not continue without eventually causing serious trouble.

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 ...

nor had any individual actually had the resources to test its...

Gawker had built this calculation into its approach.

Thiel had been asked about one of his strange investments that many people were sure would not work out.

“That’s a good thing,” he said. He liked hearing that criticism.

“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 a...

“Given the same amount of intelligence, timidity will do one thousand times more damage in war than audacity”

It’s Thiel’s investment strategy:

with the right conditions, a little boldness will make much more progress than ti...

This is slow business. It’s not glamorous. It’s expensive. There’s no visible sign of momentum. It’s not even obvious to anyone else, including your opponent, what is at stake. But what this option trades in immediate gratification and public validation, it receives in the potential for long-term effectiveness.

At a certain point in every conspiracy each participant realizes that proceeding will require of them something that little else in their life ever has. What that is isn’t willpower or resources or creativity, but instead a certain hardness and viciousness—the hard, unforgiving utilization of power or even violence against other human beings.

There is no other way to say this.

There are perpetrators and victims in a conspiracy, he...

It has been the great collective self-deception of Silicon Valley, and perhaps of our age, that a person can engage in aggressive “disruption” of existing industries while pretending that they are not at least similar to the ruthless capitalist barons of the previous century, that there is not a drop of Carnegie or Rockefeller or Vanderbilt DNA in the whole business.

Almost every conspiracy is defined by a moment in which the timeline is radically altered, when the conspirators scramble to respond to a sudden change of events.

It’s the drive where you hit every red light. The project where everything seems to go wrong, at the same time. When you ask yourself, “Why can I not just catch a fucking break?”

It is the nature of conspiracy. If it was easy, everyone would do it.

The essayist and investor Paul Graham, a peer and rival of Peter Thiel’s, has charted the trajectory of a start-up, with all its ups and downs.

“trough of sorrow.”

“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.”

This is going to be harder than they thought.

It always is.

Yes, it had not occurred exactly as expected, but that’s how it goes.

In being forced to drop the case in federal court and limit their case entirely to state court, the conspirators were given a lucky break.

There were other subtle advantages, too, which were there now but would only come to reveal themselves as time passed.

Thiel was the one behind the conspiracy, so he gets all the credit and the blame.

Yet Hogan deserves some, too.

He was the one who charged ahead, who could have accepted any of the settlement offers that would be forthcoming, who didn’t need to and probably shouldn’t...

It probably would have been smarter for him ...

It cannot be said that Gawker was not warned.

Deterrence is an important strategy. The more intimidating you are, the less people conspire against you. Yet the powerful must always be very careful with their threats, with their demonstrations of superior resources.

Aimed poorly, they have a nasty habit of backfiring.

makes it clear how much he relished this kind of ignorance. It’s what he exploits, counts on even.

“The things that I think I’m right about,” Thiel said, “other people are in some sense not even wrong about, because they’re not thinking about them.”

In this sense, it’s an oversimplification to say that Gawker was wrong abo...

It was actually much worse. It was totally and utterly un...

If they had never been deposed, it meant that this was all unfamiliar territory to them, and that the decisions Gawker would be making were going to be tinged with that arrogance.

what would a jury think of those comments? What would it be like to put these two on the stand?

There is something invigorating about taking action, getting away from the planning and toward the doing. But the feeling you get when it seems like real progress is being made, that you could ac...