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Conspiracy by Ryan Holiday: Summary & Notes cover

Conspiracy by Ryan Holiday: Summary & Notes

by Ryan Holiday

8/10Get on Amazon2-min readUpdated Nov 2025

In One Sentence

The true story of Peter Thiel's secret, decade-long plan to destroy Gawker Media through funding Hulk Hogan's lawsuit—a modern tale of power, revenge, and patience.

Key Takeaways

  • Long-term thinking and patience can achieve seemingly impossible goals
  • Strategic secrecy is sometimes necessary
  • Revenge served cold: wait for the right moment
  • Understand your enemy's weaknesses
  • Legal and financial warfare are real tools
  • Even powerful institutions have vulnerabilities

Summary

A fascinating book, despite being a self-admitted departure from Ryan Holiday’s usual writing. I listened to this as an audiobook, which I think is the best way for this particular book.  The story itself is fascinating - a modern conspiracy actually carried to fruition, but the questions it brings up are even better:What would it look like if more people planned, took deliberate action, to accomplish a goal?What if more people took action to change the world behind the scenes, instead of talking about it?Immaculate contingency planning, humility, and resources can bring great results. Where can I incorporate these tactics in my own life?Overall, a fun departure from typical non-fiction that I very much enjoyed.  Would certainly recommend, and as I mentioned, I’d suggest the audiobook.

Who Should Read This Book

  • Anyone interested in power and strategy
  • Media and tech industry observers
  • People who enjoy true stories of revenge
  • Strategic thinkers

FAQ

What is Conspiracy by Ryan Holiday about?

It tells how Peter Thiel secretly funded Hulk Hogan's lawsuit against Gawker for publishing his sex tape. Thiel waited years after Gawker outed him as gay, found the right case, and systematically destroyed the media company through the legal system.

Click to expand comprehensive chapter-by-chapter breakdown (~15-20 min read)

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