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

by Ryan Holiday

Machiavelli wrote that fortune—misfortune in fact—aims herself where “dikes and dams have not been made to contain her.” Clausewitz said that battle plans were great but ultimately subject to “friction”—delays, confusion, mistakes, and complications. What is friction? Friction is when you’re Pericles and you lay out a brilliant plan to defend Athens against Sparta and then your city is hit by the plague. Friction is when your trusted research tells you one thing but you come to find the situation on the ground is completely different, that the data had it all wrong. Friction is the Russian rasputitsa, the endless mud that makes quick work of brilliant plans and bigger armies. And so 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. One must not just steel one’s heart but also one’s spirit so that there is no such thing as an obstacle—just information. The earlier you spot and anticipate setbacks, the less demoralizing they will be. We want things to be easy. We want them to be clean. They rarely are. Napoleon’s dictum for the general-in-chief is that he “must not allow himself to be elated by good news or depressed by bad.” In the course of any campaign there will be plenty of both. A conspiracy meets with more setbacks than successes. It’s rolling the dice—making a decision, knowing that...