In 2007, a short blog post on Valleywag, the Silicon Valley gossip site of Gawker Media, outed PayPal founder and billionaire investor Peter Thiel as gay. Thiel's sexuality had been known to close friends, but he didn't consider himself a public figure and believed the information was private. According to author Ryan Holiday, Thiel then began to plot his revenge.

Thiel’s plan found him with an unlikely ally: wrestling star Hulk Hogan. After receiving an unsanctioned sex tape featuring Hogan, Gawker published the controversial video. Holiday says this was the opportunity Thiel was looking for; he would pit Hogan against Gawker in a multiyear proxy war through the Florida legal system, culminating in a $140 million dollar judgment against Gawker, leading to its bankruptcy and closure.

Only later would the world learn that Gawker's demise was not incidental—it had been masterminded by Thiel himself. The verdict and the reveal of Thiel as its mastermind stunned the world. Why had he done this? How had no one discovered it? What would this mean for the First Amendment? For privacy? For culture?

Join us as Ryan Holiday recounts this wild tale.