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Podcast #412: The Power of Conspiracy and Secrets | The Art of Manliness

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Back in 2016, a bizarre story emerged in pop culture. Professional wrestler Hulk Hogan won a $115 million dollar lawsuit against the gossip website Gawker for publishing a sex tape that had been made without his consent. The victory was somewhat surprising but the real surprise was who was actually behind the lawsuit; it wasn’t Hogan himself, but the billionaire founder of PayPal, Peter Thiel.

Thiel had his own axe to grind against Gawker, and he had been honing it since 2007. He had been plotting to take down Gawker for almost a decade.

What may sound like a tawdry story of celebrity and scandal, actually contains surprisingly potent lessons on revenge, Stoicism, strategy, perseverance, hubris, privacy, and the underrated power of secrets.

My guest today dug into this story and its insights in his new book, Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue. His name is Ryan Holiday, and he’s also the author of Growth Hacker Marketing, The Obstacle Is the Way, Ego Is the Enemy, andThe Daily Stoic. Today on the show Ryan and I discuss his latest book, and the lessons we can take from a story that reads much like a modern-day Count of Monte Cristo.

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