2018

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

von Ryan Holiday

★★★★★

“Anyone who is threatened and is forced by necessity either to act or to suffer,” writes Machiavelli, “becomes a very dangerous man to the prince.” Confusum est, quidquid usque in pulverem sectum est—cut anything into tiny pieces and it all becomes a mass of confusion.

Core Learnings
01

“Anyone who is threatened and is forced by necessity either to act or to suffer,” writes Machiavelli, “becomes a very dangerous man to the prince.”

02

Confusum est, quidquid usque in pulverem sectum est—cut anything into tiny pieces and it all becomes a mass of confusion.

03

“Anyone who has a guilty conscience can easily be led to believe that people are talking about him,” Machiavelli warns conspirators. “A word with another meaning is overheard which shakes your courage and makes you think it was said with respect to your plans. The result is that you either reveal the conspiracy yourself by fleeing or you confuse the undertaking by acting at the wrong time.”

04

An investor tells me that with each investment, Peter Thiel likes to ask: What do I know about this company that other investors don’t know? In other words: Do we have an edge? It’s only with some sort of informational asymmetry, goes the thinking, that one can not only beat the market but dominate it, and get the kind of return that takes a $500,000 check and turns it into a billion.

05

We used to throw bombs, now we throw tantrums—or worse, tweets. In ancient times it was the foolish sophists who believed that every problem could be talked through, that the logical, obvious, and right thing would simply come about if explained well enough. It’s the realists who know that this isn’t how things actually work, who know that realpolitik is how things actually get done.

Top Highlights
"“Anyone who is threatened and is forced by necessity either to act or to suffer,” writes Machiavelli, “becomes a very dangerous man to the prince.”"
"Confusum est, quidquid usque in pulverem sectum est—cut anything into tiny pieces and it all becomes a mass of confusion."
"Machiavelli would say that when overconfidence enters men’s hearts, “it causes them to go beyond their mark . . . to lose the opportunity of possessing a certain good by hoping to obtain a better one that is uncertain.” In plain language: perfect is the enemy of good (or good enough). Clausewitz warned generals about the “culminating point of victory.” A point where, if blindly ridden past, flush with the momentum of winning and strength, you imperil everything you have achieved. The decision to attack one additional city, to charge after the enemy who has retreated, or to extend the battle for one more day might not just be subject to diminishing returns, it might snatch defeat from the jaws of victory. Every conspiracy runs this risk, and often, the conspirators know they have passed it only after it is too late."
"Being feared, Machiavelli says, is an important protection against a conspiracy. The ultimate protection, he says, however, is to be well liked. Not simply because people who love you are less likely to want to take you down, but because they are less likely to tolerate anyone else trying to, either. If a prince guards himself against that hatred, Machiavelli writes, “simple particular offenses will make less trouble for him . . . because if they were even of spirit and had the power to do it, they are held back by the universal benevolence that they see the prince has.”"
"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."
"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."
"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."
Action Items
  • →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. Which is the truest of them for Thiel? Does it matter? Someone had begun to think seriously that something needed to be done and believed that he might be the person to do it.
  • →You launch a conspiracy to protect your privacy and make yourself famous. You seek to rid the world of a bully and you find yourself with Trump. The nihilists on the left are sent in a diaspora from Gawker to other media outlets, matched tit for tat by the nihilists on the right. And most of them hate you.
  • →Being feared, Machiavelli says, is an important protection against a conspiracy. The ultimate protection, he says, however, is to be well liked. Not simply because people who love you are less likely to want to take you down, but because they are less likely to tolerate anyone else trying to, either.
  • →If you want to have a different world, it is on you to make it so. It will not be easy to do it—it may even require things that you are reluctant to consider. It always has. Moreover, that is your obligation if you are called to a higher task. To do what it takes, to see it through.

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