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ryan_holiday2288 karma

To me, this story is not just the story of a ten year revenge plot, it's really the story of all conspiracies. You know we live in this world of conspiracy theories (I happen to live in Austin, the hometown of Alex Jones) but few actual conspiracies. But any student of history knows that the world often pivots on something a few people cooked up in secret. So to me, this book was a chance to tell that larger story. The fact that Thiel was willing to go on the record and explain his process was, in my view as an author, an unprecedented chance to lay out how power really works in a way that few have been able to before. It's ironic, Gawker's informal motto was that they showed "How Things Work"--the story behind the story. But in this case, they missed what was actually happening. So did everyone in the media. What I tried to do here was step back, take judgment out of the picture, and show what went down and why. I think the book captures that, but ultimately that will be for the readers to decide.

ryan_holiday2128 karma

I thought he would seem much more angry than he ended up seeming. I spent enough time with him that if that had been the primary motivation, I think the mask would have slipped--if only for a second. Instead, he seemed very calm, very detached, very strategic about the whole thing.

The other interesting part of Thiel's personality is that he uses the steel man technique when arguing or explaining a complicated issue. This surprised me given that he had taken to calling Gawker terrorists and such. But really, he was always very open-minded when it came to discussing things. For instance, if you ask Thiel a question—about Gawker or Trump or whatever—he doesn't just pull up some half-formed opinion. Instead, he begins with, “One view of these things is that . . . ,” and then proceeds to explain the exact opposite of what he happens to personally believe. Only after he has finished, with complete sincerity and deference, describing how most people think about the issue, will he then give you his opinion, which almost always happens to be something radically unorthodox—all of it punctuated with liberal pauses to consider what he is saying as he is saying it. Even when he does describe his opinion, he prefaces it with “I tend to think . . .” or “It’s always this question of . . . ,” as if what he is about to tell you is simply capturing where his opinion falls the majority of the time when running a thought exercise on the topic, as if he is always in the process of deciding what he thinks. I found that to be very impressive and unusual. It was hard to be a lazy thinker around him.

ryan_holiday2106 karma

The police reports, which you can pull out from the trial documents off the website of the Pinellas County Courthouse, suspected that the tapes were leaked by a rival radio DJ Matt 'Spiceboy' Loyd. He was never charged with the crime so we should be careful about pointing fingers, but as far as a best guess goes from both the FBI and the Tampa Police, that's it. Even weirder--weirder than this entire dispute being put into motion by a fight between two shock jocks--is that the lawyer who represented the brokering of the sales of the tape was a man named Keith M. Davidson, who later came to represent Stormy Daniels after her alleged affair with the man who is now the President of the United States of America...

Edit: article here about that insane set of circumstances.

ryan_holiday1137 karma

I'm not sure I convinced them, so much as the fates aligned. I happened to get an unsolicited email from Thiel in late 2016--he had read some of my Gawker columns and suggested we get dinner sometime. I got an email from Denton not long after saying he'd read some of my philosophical writing and wanted to know if I wanted to get together. That I was talking to both of them I think was intriguing to them both, and also meant the other would want to keep talking for fear that the project might be too heavily weighted by one side. I also kept the project's direction really open for a long time--was it a book about media or technology or these two characters or was it about revenge? I really didn't know, but that allowed me to ask about a wide range of things so it never felt super invasive or "gotcha"-y. Denton preferred to do his interviews over chat, so our process was also much less of an imposition. Meanwhile, I think Thiel is quite proud of what he had accomplished and was tired of the very biased reporting around it.

ryan_holiday964 karma

The central question of this story to me is, who was the bully? Was Thiel the bully or was it Gawker? Was Peter the billionaire who destroyed a millionaire? Or was he a righteous man who attempted to use his money to solve a problem that only power and money could solve? Was it the media outlet that thoughtlessly outed a then-mostly unknown tech investor? Or was it the billionaire who spent millions plotting against him for it? Was it the website who loved to out gay men or was it the team who would back Trump in the 2016 election, and in the case of Charles Harder, write an 11 page letter threatening to sue Michael Wolff for his book about Trump? Was it Denton who never apologized, who ignored judicial orders or was it Thiel, who never showed his face until after his revenge was complete?

It depends on where you sit, but one thing that has been lost in the coverage since the verdict: Gawker thought they were winning until suddenly, they lost. It was Gawker who had filed endless motions and appeals, who had fought Hulk Hogan with scorched earth tactics, and never apologized for obtaining an illegally recorded sextape and publishing it for more than seven million people to gawk at (and then spent $10M+ vigorously insisting it was right to do so). There was a moment in mid-2014, when Gawker’s lawyers threatened Hulk Hogan, telling him that it was his last chance to drop the case before they went after him for attorney’s fees. More than anything, what the jury and the judge reacted to had been their arrogance. The verdict reflected that.

Nick Denton told me, “The idea that Thiel was terrified of the next Gawker piece is still absurd to me—and given how things turned out, we had much more to fear from him than the other way around." But it wasn’t that absurd at the time, when they were a website with hundreds of millions of readers, when Gawker was the site that had never been challenged in court and published whatever it wanted, Thiel believed that Gawker’s power was partly in pretending that it was more powerful than it was. Now that they're gone...it looks different.

As for who is the bully now? As I said, backing Trump and some of the clients Charles Harder has taken on since give me pause...but that doesn't have the power to rewrite where things were in 2007.