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

(New York: Portfolio / Penguin, 2018), 336


  • Discourses on Livy by Machiavelli: chapter on Conspiracies; sometimes conspiracies are the way to solve problems
  • This book is a meditation on how to conspire

Chapter 6

  • Peter Thiel: holds opposing views in his mind to probe them
  • Journalists: the ends justify the means

Chapter 9

  • Denton and Dalerio underestimated the deposition and their testimony came back to haunt them: never underestimate your enemies
  • This was Gawker’s black swan: can’t predict the future with the past, cf. Nassim Nicholas Taleb’s Turkey

Chapter 10 - the power of secrets

  • “History is one long exercise in the triumph of secrets”; but transparency carries in the modern world the weight of moral imperative

Chapter 15

  • "A leader may be defeated but should never be surprised"

Chapter 16

  • “Thiel had proven that ‘nothing you can do about it’ is just what people who don’t want to do anything about it say to make themselves feel better about their inaction.”

Chapter 18

  • One of Thiel’s favorite novels: The City and the Stars by Arthur C. Clarke


  • “If you want to have a different world, it’s on you to make it so”...
    “In a time when computers are replacing many basic human functions, it will eventually come to be that audaciousness, vision, courage, creativity, a sense of justice: these will be the only tasks left to us.”

Source: Dad


  • Discourses on Livy by Machiavelli
    • The City and the Stars by Arthur C. Clarke

Created: 2021-12-20-Mon
Updated: 2023-01-23-Mon