Podcast #412: The Power of Conspiracy and Secrets

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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.

Show Highlights

Why was Ryan drawn to this story? How did he end up chronicling it?
How did Ryan choose an approach to this book? How did he write it differently than most journalists already had?
The backstory of Gawker.com and its outing of Peter Thiel
Why it took 4+ years for Thiel to realize he could do something about it
How did Thiel find and end up paying for Hulk Hogan’s case against Gawker?
What Ryan meant in calling Thiel a “high agency” individual
Can a person become high agency? Or are you born that way?
Why Thiel wants to be underestimated and under-the-radar
Why competition is for losers
The difference between conspiracy and war
Why Thiel sought revenge rather than taking, say, a Stoic approach to the problem
Did Thiel go too far? Why was his identity and scheme revealed?
Why secrecy can actually be an effective, powerful tool in getting things done
The value of privacy in our modern transparent society
How did all the players in this story turn out?
What happened when Thiel and Denton met in person?
Ryan’s takeaways on strategy, getting things done, etc.

Resources/People/Articles Mentioned in Podcast

Connect With Ryan

Ryan on Twitter

Ryan’s website

Ryan on Instagram

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