After Conspiracy: Ryan Holiday’s Latest Take on Thiel

Ryan Holiday is the bestselling author of Trust Me, I’m Lying, The Obstacle Is The Way, and Ego Is The Enemy among others.

His most recent release Conspiracy explores how billionaire Peter Thiel leveraged Hulk Hogan’s privacy case against Gawker Media to bring down the controversial media site. It’s one of the most fascinating courtroom dramas of our age and one that’s sure to have lasting legal repercussions. We caught up with Holiday to get his take on how the story’s developed since Conspiracy was published.

The Gawker-Thiel story has been unfolding for quite some time now. When did it begin to pique your interest?

Like many people, I followed the story as it was happening because it was insanely entertaining. A professional wrestler, a sex tape with his best friend’s wife, a $100M lawsuit against a gossip website, the twists and turns of the trial and then a $140 million dollar, bankruptcy-inducing verdict? I mean the whole thing is insane. Then to add on top of that—which nobody, myself included, suspected—that it was all put into motion and funded by a billionaire seeking justice and revenge for something the website had done to him? It’s an incredible, Shakespearean story that does not come along often.

Since the publication of Conspiracy in February this year, it’s emerged that Thiel has ended his bid to buy the now-defunct Gawker site. What’s your take on this?

Thiel’s goal, from the outset, was to destroy Gawker. This was the stated intention almost all the way through among the conspirators. I don’t think he ever wanted to own Gawker. If he did, he could have bought it, or tried to buy it at really any time. In fact, Peter Thiel and Sean Parker did hypothetically discuss purchasing Gawker a few times between 2007 and 2012. And again, between the two of them they could have purchased the $300M company without flinching.

The premise is to show how this all happened, so we can, as I said, understand how power works. You can’t learn from what you turn up your nose at.

The reluctance was 1) in rewarding what they believed was evil behavior and 2) then having to own the website and figure out what to do with it. After the verdict and once the site was bankrupt, I think Thiel found himself in the negotiations to buy it partly because he didn’t want other people to have it (like former Gawker writers) but really I suspect it was a negotiation tactic. As part of the settlement, Gawker’s estate is dropping any claims they have against him in return for him not purchasing the site. So in this way he got to finally negotiate a peace through the leverage he had with the threat to purchase.

Is there anything that didn’t make it into the book that you would have liked to include?

I mean, so many things. This book only scratches the surface of what happened. If I had the space I would have written about how this tape came into existence and how it was stolen. But there is only so much room and I think it says something about the material I was blessed with here that the consensual hook up between Hulk Hogan and the wife of his best friend (named Bubba the Love Sponge), and then its subsequent extortion attempt (which was orchestrated by Keith M. Davidson, the man who negotiated the Stormy Daniels settlement with Trump’s lawyers) was cut because it wasn’t interesting enough.

Was Gawker just unlucky? Tabloids publish salacious details about prominent people all the time. What’s the difference here?

Unlucky?! That’s not the word I would use here at all. First off, Gawker repeatedly picked fights with powerful, aggressive people—that was their style and they loved it. Secondly, Gawker published—without thinking or hesitation—a tape even TMZ declined to publish. It was a surreptitiously recorded sex tape that had been stolen! The people in the tape promised to sue whoever ran it, begged Gawker to take it down, a judge ordered Gawker to take it down… Unlucky is not the word I would use to describe what happened to Gawker. Not at all.

What’s the lesson here for media sites? What message does this case send out?

It’s pretty simple. Don’t be stupid. Don’t be cruel. Know who your enemies are and keep a close eye on them. And like the line from The Wire, if you shoot at the king, you best not miss.

In Nick Denton’s final post on the site, he wrote that the entire story of its demise was “the ultimate Gawker story. It shows how things work.” Is this true or just compelling spin?

It’s completely true. It was the ultimate Gawker story in many ways, which is what makes it so interesting that in some ways, Gawker was the last to realize it. Thiel said to me at one point—and I think he knew this was a bit glib—“What does it say that an investigative journalism outlet can’t uncover a conspiracy directed against them?” And I think there is truth in that. But really to me, this story shows how power really works and how it can get what it wants, when it is determined and disciplined enough. It’s scary what this story shows, in some ways, but also enlightening and important.

Does the law actually uphold freedom of speech while protecting privacy, or simply protect the interests of the people who can afford the exorbitant legal fees?

This is a silly argument to me. Hulk Hogan won his case. A Florida jury and a judge looked at the facts of the case and ruled overwhelmingly in his favor.

Don’t be stupid. Don’t be cruel. Know who your enemies are and keep a close eye on them. And like the line from The Wire, if you shoot at the king, you best not miss.

The idea it required $10 million dollars of Peter Thiel’s money to get there is in its own way an indication of the problem of our legal system. The notion that Gawker, who spent $10M+ of their own money, was deprived of justice because they lost is ridiculous to me. The idea that it is essentially impossible for even a wealthy individual like Hulk Hogan to litigate a fairly simple case like this on his own? That to me is evidence that our legal system in America might only protect people who can afford exorbitant legal fees.

Where’s the line between the public violation of Hulk Hogan’s privacy and the covert privacy violation of 87 million Facebook users?

Well, there is now some evidence that Thiel’s company Palantir was connected to Cambridge Analytica, but other than that I don’t think there is much of a connection… unless a smart, enterprising person wanted to pick up Thiel’s playbook and find a way to hold Facebook accountable. That’s what I want people to realize about this book. The premise is to show how this all happened, so we can, as I said, understand how power works. You can’t learn from what you turn up your nose at.

Do you have any final thoughts or conclusions on this story that you’d like to add?

I think it’s my best book. I’m glad I wrote it and I hope people read it. The people I would most like to read it are the people who think they already know what happened and have strong opinions about it. Because the embarrassing thing about this is how many very talented reporters and analysts have not only missed what the really important themes of this story are, in some cases, they’ve just gotten the whole story dead wrong. I saw it even in the coverage of the book, reporters whose agendas and preconceptions were so strong, there is no other word to describe their actions but as “bad faith.” It almost makes you understand why people sue media outlets…

Our thanks to Ryan Holiday for taking the time to share his thoughts with us. And if you haven’t yet, check out the Blinks to Conspiracy. And then buy the book, because once you start reading about this case, you’re going to want to know the full story.

And don’t forget to listen to his Simplify interview here.