In the book’s biggest revelation, Holiday reports for the first time that a twentysomething acquaintance of Thiel’s, identified only as Mr. A, not only came up with the idea in April 2011—before the publication of the Hogan video—to target Gawker through an open-ended legal fund but also spearheaded the plot to take down Gawker using Thiel’s money.

I spoke to Holiday last week about the new information he’s uncovered, whether he thinks Gawker could have saved itself before the trial, and whether news reporters reflecting on Gawker’s demise should live in fear of upsetting rich people with their work. This interview has been edited and condensed for clarity.

Derek Thompson: On December 19, 2007, Gawker’s tech blog Valleywag published a post under the headline “Peter Thiel is totally gay, people,” ending with the sentence, “I think it's important to say this: Peter Thiel, the smartest VC in the world, is gay. More power to him.” Based on your conversations with Thiel, why do you think he’s so mad about this blog post, if most of his friends (and their friends) knew he was gay?

Ryan Holiday: My initial instinct was that it must have been pure anger. What was strange, though, is that in speaking to Peter Thiel, I never saw the anger. Of course, sources can present a mask. But I feel like I would have seen a flicker of it.

I think what happened was this: The article comes out, and it is a rude awakening for a private person. The article was legal, but it was also tasteless and deliberately insensitive. But what Peter reacts to the most is the comment on the bottom, which was written by Denton. [The comment is one sentence long: “The only thing that’s strange about Thiel’s sexuality: why on earth was he so paranoid about its discovery for so long?”] He thought Denton was implying that Peter had psychological problems. When you read the comment it doesn’t feel that way. But Thiel thought, here is the publisher of a media outlet, not just a blogger, going after me. That blog post felt like the first article in years of negative Gawker coverage against Thiel.

Thompson: Since Thiel’s war on Gawker bankrupted the company, that’s probably the most expensive internet comment in world history. I was really struck by your reporting that Thiel went around calling Gawker “the MBTO,” which stood for “Manhattan-Based Terrorist Organization.” Why did he feel terrorized?

Holiday: I think there is an element of unpredictability to it. Most of the media plays by certain rules. But Gawker wrote its own rules, and that scared certain powerful people. Outing was more or less off limits for most news outlets. So I think what kept Thiel and people like him up at night was: If they can out me, then what’s next? Will they publish a harmful rumor? Even a false rumor?

Thompson: Thiel ponders revenge for years. Then, as you report, in April 2011, he is in Berlin and he takes a dinner meeting with a then-26-year-old Thiel devotee, who you call Mr. A. This young man essentially tells Thiel, I know you’re obsessed with Gawker, and I have an idea to destroy them. He says Thiel should create a shell company to fund investigators and lawyers to find causes of action against Gawker and ultimately sue it into oblivion. He estimates that the plan will take up to five years and up to $10 million in funding, which is prophetic. What struck you most about Mr. A’s story?