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

Updated: November 1, 2022 Reading Time: 9 minutes rating: 9
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Peter Thiel will go down in history as one of the most mysterious yet successful characters of our generation. People will study him for his tactics and strategies and for his ability to hold controversial and opposing views in his mind at the same time. After all it is not common to be a gay libertarian that supported Trump during his first candidacy so much that he even spoke at the Republican convention in 2016.

This book is inspiring on multiple fronts.

In my view it is Ryan Holiday’s best writing because it is in some ways very different from his other books (mostly on stoicism and marketing) and yet very similar as Thiel’s conspiracy against Gawker had many traits of everything that Ryan is an expert of: history, fighting and embracing obstacles, deceitful media and strategies. In retrospect, there couldn’t be anyone more suited to tell this story than him

Thiel’s story is inspiring because it shows that even for the most powerful people of this world things can be scary only a handful are brave enough to risk their reputation (and a bit of their money) to fight for a cause that they believe in but that to most people is “not worth fighting for”. In a sense it is also a story about starting up and Thiel is an expert at that. Like a startup a conspiracy requires finding a group of people “crazy” enough to work on something that nobody believes in and that is most likely to fail

All Highlights and Notes

Conspiracy is a neutral word. It depends on what one does with it. Our tendency to shy away from this truth creates a profound ignorance of how things really work, and what it means to be strategic, to be powerful, and to try and shape events rather than simply be shaped by them

“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 wield power in an attempt to change the world? We could almost always use more boldness, and less complacency. 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 disruption, even from the people we disagree with.

Privacy. The space to be peculiar, to think for oneself and to live as one wishes.

Every conqueror believes their cause just and righteous—a thought that makes the fruits taste sweeter.

His writers obsess over this number (view count), refreshing the stat counter over and over, and begins to pay them accordingly. He puts up a large screen in the office that ranks the writers and the articles based on traffic. He calls it the “NASDAQ of Content”

What Denton did, in effect, was turn writing, social commentary, and journalism into a video game.

They were practicing journalism by tomahawk. 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?

Fights break out. Conspiracies brew

The economist Tyler Cowen once observed that at some point in the 1970s, Americans went from being the country that took literal moonshots to being the people who waited patiently in long lines for gasoline. It’s not completely accurate, of course, but it is a criticism that resonates with Thiel as he sits in his office at the Presidio one day looking at the Golden Gate Bridge and wonder if people will ever build something like that again. Do people even have the arrogance anymore? To test the limits? To try big things?

Only after he has finished, with complete sincerity and deference, describing how most people think about the issue, will he then give you his opinion, which almost always happens to be something radically unorthodox—all of it punctuated with liberal pauses to consider what he is saying as he is saying it. Even when he does describe his opinion, he prefaces it with “I tend to think…” or “It’s always this question of …”

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.

Machiavelli said that conspiracies were weapons of the people. Only princes could afford to send an army against another army.

One can’t shame the shameless

“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 it even. The other questions it, fights it, rejects it.

Lawrence Freedman writes that “combining with others often constitutes the most strategic move.” By definition, the first move in the act of a conspiracy is the assemblage of allies and operators

One quickly finds that he is a man notoriously averse to small talk, or what a friend once deemed “casual bar talk”

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

  • The same holds true in most endeavors. There can’t be more than one captain
  • “Mucho Cacique y poco indio”

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

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."

His favorite chess player was José Raúl Capablanca, and remind himself of the man’s famous dictum: To being you must study the end. You don’t want to be the first to act, you want to be the last man standing

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”

What do I know about this company that other investors don’t know? In other words: Do we have an edge?

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

Thiel’s default state is to embody contradiction. Doing so is what makes him such a brilliant investor, considering each trade and investment anew from a dozen perspectives, seeing what others aren’t able to see and doing it on a regenerative basis. A friend would say that “Peter is of two minds on everything. If you were able to open his skull, you would see a number of Mexican standoffs between powerful antagonistic ideas you wouldn’t think could be safely housed in the same brain."

One of the informal mottos of the libertarian community is “Don’t hurt people and don’t take their stuff”

It’s the drive were 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. Fate rarely conspired to help conspirators—and if it was on their sid, why were they forced to do all this sneaking around then? No, fate sends to the conspirators of the world the best of its Murphy’s Law and entropy and crises of confidence.

The essential trait of the successful man is not only perseverance but almost a perverse expectation of how difficult it is going to be. It is having redundancies on top of redundancies, so you can absorb the losses you eventually incur.

“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”

We have a complex relationship with secrecy. Transparency carries now in the modern mind the weight of moral imperative.

Being feared, Machiavelli says, is an important protection against a conspiracy. The ultimate protection, he says, however, is to be well liked

This kind of purity is childish, the domain of people who live in the realm of theory and words and recoil from the real world where someone can punch you in the face if you say the wrong words to the wrong person.

“You argue the law to show how much you know about the law,” he would say, " but it’s not how you win a case in front of a jury”

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

Charlie Wilson worked with the CIA to fund a guerrilla resistance to the Soviets in Afghanistan and won. There wasn’t much of a plan for what to do with these trained and armed fighters afterward. He would say, “These things happened. They were glorious and they changed the world. And the people who deserved the credit are the ones who made the sacrifice. And then we fucked up the endgame.” Those same fighters became the Taliban and sheltered Osama bin Laden.

Of the dangers after a successful conspiracy, Machiavelli would say, “there is only one, and that is when someone is left who may avenge the dead prince.” For this reason, Robert Greene, warns, one must “crush your enemies totally”

“There is a special sadness in achievement, in the knowledge that a long-desired goal has been attained at last, and that life must now be shaped towards new ends.” - Arthur C. Clarke in “The City and The Stars”

“The idea of a conspiracy is linked with intentionality, with planning, working towards long-term goals” - Peter Thiel

The Education of a Libertarian by Peter Thiel Strategy: A History by Lawerence Freedman On War by Clausewitz