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

by Ryan Holiday

No man attacks me with impunity is well and good, but also a recipe for diving headfirst into a feud or a boondoggle. Instead, it’s the careful consideration of the costs and benefits that separates the successful conspiracies from the regrettable ones—or the pyrrhic ones.

Negative expected value—it’s a calculation Wall Street guys make every day.

It had preemptively made itself next to impossible to criticize. It was the bully that had convinced people it was the underdog, and was so confident in it, it even told everyone that’s what it was doing.

“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.”

“With patience and resources,” Mr. A would come to say often on his weekly calls with Peter, “we can do almost anything.” Tolstoy had a motto for Field Marshal Mikhail Kutuzov in War and Peace—“Patience and Time.” “There is nothing stronger than those two,” he said, “. . . they will do it all.” In 1812 and in real life, Kutuzov gave Napoleon an abject lesson in the truth of that during a long Russian winter.

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.” John Boyd, a fighter pilot before he was a strategist, would say that a good pilot never goes through the front door. He wins by coming through the back.

Liddell Hart’s maxims for strategy: “Keep your object always in mind, while adapting your plan to circumstances.” “Take a line of operation which offers alternative objectives.” “Ensure that both plans and dispositions are flexible—adaptable to circumstances.” “Do not throw your weight into a stroke whilst your opponent is on guard—whilst he is well placed to parry or evade it.”

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.