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Conspiracy – behind the scenes

Apr 07, 2018 | Posted by Cristina in Articles

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Conspiracy“, Ryan Holiday‘s new book, is the anatomy of how tech billionaire Peter Thiel brought down Gakwker media to avenge an injustice. A nearly-decade long story that involved unimaginable amounts of money and secret plotting, a sex tape of Terry Bollea, the FBI, and ended in a $100+ million verdict in a Florida lawsuit.

How Peter Thiel conspired to bring down Gawker is just the main narrative of the book (and one that’s good enough to be turned into a movie, might I add). Along the way, Holiday introduces us to many other sub-narratives.

It’s a crash-course into conspiracies throughout the history, spiced up with questions of ethics, free speech, poetic justice, power, patience, ambition, secret plotting, gaps in the legal system, underdogs, and how easy can the masses be manipulated.

Hold it right there. Before we move onto other details, a few words about all the names I previously dropped, just to make sure you have the context:

Peter Thiel is part of the so-called “PayPal Mafia” (together with Elon Musk), venture capitalist (the first investor in Facebook), founder of big data company Palantir, author of “Zero to One” – one of the most recommended books by entrepreneurs. In the recent years he also became known for his support for Trump, and the fact that he’s a doomsday prepper.

Gawker Media was one of the biggest online media companies, started by Nick Denton in 2003.

Terry Bollea? You surely know him by his stage name: Hulk Hogan.

And Ryan Holiday is… well, leaving asides the fact that he’s one of my favorite authors and, in case of a fire, I’d probably save his books first? He’s a media strategist, expert in culture and human condition. Through his creative advisory company, Brass Check, he’s worked with names from Google to Complex, Tim Ferriss, Arrianna Huffington, and more.

Holiday had direct access to all characters involved in the story and researched this book while keeping a truly curious, open mind. He doesn’t take sides, you’ll never feel he’s judgmental (though one could also argue that he was afraid to do so – not that he’s seen the possible repercussions).

This is not a fight between good and evil. It’s got all the tones of grey that are characteristic to real life’s randomness. You really get to understand their reasons and where they come from, and you’ll finish it having mixed feelings of fascination and terrible fear.

“Conspiracy” is a must read for any entrepreneur who:

… wants to learn more about strategic thinking.
… read Peter Thiel’s “Zero to One” and wants to explore even more his contrarian views and discover how his fascinating brain is wired.
… wants to learn more about how media works and manipulates, but also how it can turn against you in the blink of an eye.

Read it together with:


If you’re interested in the subject, but don’t want (or you’re not convinced yet) to read the whole book, you can also just listen to Ryan Holiday’s talk with James Altucher.

Altucher worked with Holiday in the past, so you’ll feel like eavesdropping into the late night conversation of two old friends. They dig into all the details about how Holiday built the book, his relationship with the characters involved, and a few interesting thought exercises.

James is a famous entrepreneur, angel investor and author, so in his podcast he interviewed many other fellow entrepreneurs and investors – including Peter Thiel, in 2014.

So here it is: Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue, by Ryan Holiday. It’s the type of book that you’ll probably either completely love or hate – no middle ground.

If you’re going to give it a chance, drop a comment afterwards and let me know what your thoughts are on Peter Thiel’s decisions. What scares you most? What would you have done differently?

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