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

By Ryan Holiday

Published: December 1, 2020 Reading Time: 9 minutes rating: 9


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

  1. Might this period have played a role into the current cancel culture movement? Nobody says anything anymore because we all fear being cancelled by the mob. Thiel had the audacity, and the money, to shut Gawker down. I believe it was good but wonder if the battle can ever be won. ↩︎

  2. Perhaps the only solution is to “escape competition” (borrowing from Thiel’s Zero To One) and become unemployable and uncancellable. Taleb says that the only people you should fear being cancelled by are your barber and your butcher, i.e. the people closest to you that you depend on, the rest doesn’t matter. ↩︎

  3. The first world societies have become too soft. We are complacent, we don’t have many problems, so we focus on the incremental, on the minutiae, so we end up fighting over school names, diets, etc. rather than focusing on fixing humanities biggest' challenges and building the future. Also, see It’s Time To Build. ↩︎

  4. See The Obstacle Is The Way ↩︎

  5. See Antifragile ↩︎