The Most Important Gamble I’ve Made in My Career

A writer betrays their craft if they do not push themselves.

For the last few years, I have been on a good track. I had a string of successful books and had successfully pivoted from my more controversial writing into work well-received across the political and cultural spectrum. Yet in 2016, I made a decision that gambled all those gains.

It began with two surprise emails. First from the billionaire Peter Thiel and later from the founder of Gawker Media, Nick Denton. Although I had interacted with both men previously, it struck me then, in the fall of 2016, after the landmark $140 million verdict against Gawker that had been engineered by Peter Thiel, that I was one of the few people on the planet to be speaking to both of them. The idea of writing a book about what had happened came up, but I quickly pushed it away.

I had many reasons to say no: It was outside my wheelhouse. It would be a ton of work. It would be the kind of project that would upset a lot of people. It was also personally risky…to be writing about a powerful gossip merchant and a right-wing billionaire who had just shut down a media outlet he didn’t like.

Yet for some reason, I said yes. Because although I knew it would be hard, and I knew that it might not work, I could also see that it might be the most interesting thing I ever did. And if it did work, it would be a book unlike almost any other.

Because there was really nothing like this story in all of American history. While conspiracy theories are legion, rarely do we ever see an actual conspiracy and rarer still will the people behind it admit to or talk about what happened. As I studied it, it came to feel to me like something that would have happened 130 years ago — that would only seem real if you read it as a history, like a scene in Plutarch’s Lives and not as news. As I looked for comparisons, often fiction was the only analog, Alexandre Dumas’s The Count of Monte Cristo (which as I would learn was based on a true and even weirder story) jumped out at me as a kind of prequel to my story, where a billionaire spent 10 years of his life plotting revenge for a wrong that nearly everyone else had dismissed as a function of the internet. I just could not get the story and its themes — justice, power, privacy, strategy, secrecy, hubris, corruption, evil — out of my head, as crazy and out of reach as they seemed.

After much thought, I went for it. (More on this below, but if you want to check out the book right now, here it is, Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue).

Everyone should know that a leap of faith for a writer, or really any professional, is not usually met with immediate gratification. Just as often it is followed quickly by regret. In this case, I had many. For starters, I was not a journalist. All my previous writing had either been in the first person or based on ancient history. I had little experience pulling documents or reading case files. My only exposure to interviewing sources had been as a research assistant transcribing interviews other people had done. Now I had to produce a 90,000 word book of contemporary journalism and I had to beat out a number of talented reporters who were looking to produce books of their own on the topic.

Perhaps regret is not a strong enough word. I despaired.

Pulling the legal documents alone was an ordeal. First, it required downloading nearly 3,000 of the legal case files from the Pinellas County Clerk of the Circuit Court website (7.97 gigs worth). Each file had a name like 123761.tiff so it required renaming each one to a consistent standard of YEAR-MONTH-DAY-DESCRIPTION and later converting them all to PDFs:

In the end, after sorting through the thousands of files — initially close to 30,000 pages–I sent them to the local print shop. The final quote was nearly $2,000 to print over 7,300 double-sided pages, organized in 18 binders. There was the trial itself for which a video archive cost $894 to access for six months and included some 67 hours of footage.

My son was born a week before I was supposed to start seriously researching the book, which only further threw my life into chaos and (welcome) distraction. I remember thinking beforehand that I’d have quiet time to flip through the legal binders when he was sleeping. Let’s just say that did not go as planned.

Still, I proceeded with my interviews. Sometimes I was in San Francisco in Thiel’s office. Sometimes I was gchatting with Denton from Austin. Then I would take breaks and repair fences and burn brush on my farm. In all I would conduct countless hours of interviews, at least 450 pages worth of the ones I was allowed to record and transcribe, and many hundreds of pages more done via email and chat. It took roughly 2 months to get through the legal documents and another month to produce what became a 50,000+ word, 129 page timeline of every event that had transpired in this insane story. It was a timeline that stretched from March 2002 to March 2017. At long last, I had at least nailed down what had happened.

(Timeline’s page count and word count.)

(From Timeline: Snapshot of the reveal of Peter Thiel’s involvement in May 2016.)

On February 6th, 2017, I started writing. I don’t remember when the first line of the book came to me, but I liked it as soon as I put it down. “This is the story of a conspiracy, the story of a billionaire who set out to make an example of millionaire, to destroy the man’s life’s work in response to a cruel transgression made as thoughtlessly as it was quickly forgotten.”

The sentences which came after did not come so easily. Because again, I had never written anything like this. What should the tone be? How much should I be in the book? What events were worth including? Which had to be cut? How the hell was I going to make it all the way to the end with so little time? I wrote a few pieces around this time and spoke in an interview about just how much the book I was working on was kicking my ass — and it was. I couldn’t wrap my head around it all and I couldn’t figure out my angle on it.

With time I would find the angle I was looking for and make the decision to cut with precedent and create my own style. I wouldn’t simply write a work of journalism, which I found had generally failed in previous attempts to capture the events of the plot and trial, I would mix reporting with historical analysis and anecdotes. When I had first researched the story, it felt like something that should have happened centuries ago, so why not write it that way? And I would pull in examples and stories from other conspiracies to make this book bigger than simply what happened between Thiel and Denton, because it was bigger. In this story was the story of all conspiracies — something we don’t talk about enough.

Even with this breakthrough, there would be a reason that the words would not come as easily as my previous writing had, namely that as much I saw them as historical archetypes, I was writing about real people — people who in the course of my interviews and conversations I could not help but deeply admire. Nick Denton came over to my house and his husband would hold my son, then five months old. We would stand in my office, the same office where I would write the book, where I am writing this article. How could I then write critically about him? How could I publish a book that would contain many pages he would not like? And what about Thiel? I admired him too. He gave me incredible access to his thoughts, his friends, his partners in crime. He did this in part because he believed we shared the same point of view about media and because he hoped I would be fair. Still, there would be many pages in the book he would not like either.

My editor would send me a copy of The Journalist and The Murderer as I was writing Conspiracy. It was a kind gesture but as far as clarity goes, served to painfully mess with my head. In the book, Janet Malcolm writes that journalism inherently relies on a kind of duplicity on behalf of the writer — it’s a dance, where you try to lull the source into a place of vulnerability and honesty, only to later expose that moment to as many people as possible (and hope to profit from it). “If everybody put his cards on the table, the game would be over,” she wrote. “The journalist must do his work in a kind of deliberately induced state of moral anarchy.” Denton himself would say in one of the depositions I watched, “It’s up to others to determine the boundaries of acceptable social, ethical and legalistic norms. . . . It’s up to others to have regard for their own emotional well-being. The job of a journalist would be unbearable if one was always to put oneself in the shoes of a subject.”

Maybe that’s true, but it didn’t make the process any easier. I agonized over it. Over every word. Especially the words about Nick, criticism of Peter, quotes from sources I knew they would probably rue ever giving to me. Considering I had written critically of Gawker in the past, and considering how reprehensible I found many of their actions, I never thought that would be the case. Each person I talked to, no matter my preconceptions, was obviously a person — and people rarely act out of malevolence. They always have reasons and often those reasons are pretty good. At some point in the interview process, after many long conversations, A.J Daulerio suddenly asked me to stop contacting him. I was crushed.

Maybe I lack the strength of character for this line of work, or maybe that empathy created something special across the pages I am publishing. The reader will have to decide that. I did tell myself that if both Thiel and Denton were unhappy with parts of the book then I did my job. If there were parts each liked, then I did my job well there too.

Perhaps what made all these issues more difficult was the compressed timeframe in which they all needed to be addressed. The book was proposed, sold, researched, written, edited and printed in roughly a year. The schedule was rushed first because this was a story that remained in the headlines and contained a certain contemporariness that we wanted to capture, but it was also rushed because there was a constant threat of being scooped by other writers. I could tell in my conversations with journalists who had covered the case — some of whom admitted it to me when I tried to interview them — that they were shopping their own books on the trial. Beating them to market required both speed and stealth: For instance, inside my publisher the book was referred to only as “Ryan’s upcoming media book,” (my shorthand was UMB) and only three or four individuals knew its true subject matter. When we announced the book in the summer of 2017, I played a little trick. We put the expected release date as Winter 2017, even though it would be next to impossible to hit that deadline — the intention was to deter other publishers from buying books on the case. By the time it became clear the book wouldn’t be released until early spring of 2018 it was too late for anyone to catch me.

Last week, the copies finally arrived. I could hold the book in my hands. This strange, surreal, career-detour of a book. It struck me as I held it that from start to finish it was the same age as my son, and how cool that was. But mostly I was proud of what I had made.

It’s a book very different than anything else I have done. How many copies it will sell, whether the media will savage it for daring to question the dominant narrative of those events which transpired from 2007 to 2017, I cannot possibly know. Whether my own fans will appreciate it right away or whether it will take time to earn its reputation, I don’t know either. I take some solace, in advance, of Rick Rubin’s line, which I quoted in Perennial Seller, that “the best art divides the audience.” I know I have written something unique and of value. I believe I said something important — in these tumultuous times especially.

But for now, it remains a gamble with an uncertain payoff.

We’ll see what comes of it.

In the meantime, I ask you to give it a chance — as I did — and let me know what you think.

Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue

Bestselling author of ‘Conspiracy,’ ‘Ego is the Enemy’ & ‘The Obstacle Is The Way’