I’ve been a Ryan Holiday superfan since 2012.
He’s a modern-day genius and my favorite writer. I was fortunate that I was able to meet him and see him speak in a small venue back in 2017.
In the years since, Holiday’s popularity has exploded. He has spoken to senators and professional sports teams, executives and armed forces. While Holiday has become well-known for his work focusing on Stoicism, the best book of his entire oeuvre is actually one that is not dedicated to that philosophical discipline.
In 2018, he published Conspiracy, the inside story of how Peter Thiel and an operative secretly funded Hulk Hogan’s lawsuit against the gossip website Gawker that resulted in a $140 million verdict and led to the site’s bankruptcy and shuttering.
While serving as Director of Marketing at American Apparel, Holiday had been the subject of Gawker posts from time to time, but the impetus for the book came about after both Peter Thiel and Gawker founder Nick Denton reached out to speak to him independently shortly after the verdict.
The result is a captivating read that details how a brilliant Silicon Valley billionaire, a maverick New York publisher, and a sex tape of a very famous professional wrestler that was recorded by a radio shock job all collided into one another.
In a review for The New York Times written at the time of the book’s publication, William D. Cohan acknowledges that the book is “one helluva page-turner,” but is also critical that Holiday’s “incessant name-dropping” (he loves to quote widely) “tends to detract from his gripping narrative” and that he’s “less successful…in pushing his view throughout the book that [this was] an old-fashioned ‘conspiracy.’”
My contention, however, is that those elements are what elevate it, that make it a superb book rather than simply a fine one. It’s this approach that takes the work beyond one that is a cash grab in the form of a simple recounting of events that transpired. A lesser book, by a lesser author, would have read like a detailed Wikipedia entry, a rote retelling and nothing beyond that.
There would not have been larger ideas — about conspiracies and strategy and the ultimate cost that revenge takes, even on those that are victorious. That lesser book would not be filled with quotes from the likes of Machiavelli, Lucretius, Sun Tzu, Herodotus, Thucydides, and Clausewitz or include references to Hamlet and Hofstdter’s Law, the Gunpowder Plot and the surrender at Appomattox.
A glimpse of that other book can seen in how the paperback version differs from the hardcover. The original subtitle for Conspiracy — Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue — is understated. It presents the book as it is — the result of deep thought that gives great consideration to the long-term ramifications of what transpired.
Conversely, when the book was published in paperback, it was replaced by a far more tantalizing (but less intellectual) subtitle — A True Story of Power, Sex, and a Billionaire’s Secret Plot to Destroy a Media Empire — along with a photo of a visibly angry Thiel.
In interviews, Holiday has said that this was one of his lowest-selling books but also the one he’s most proud of, as he pored over twenty-thousand pages of legal documents and stretched himself as a writer in tackling narrative nonfiction for the first time.
While the new subtitle and cover virtually guarantee more copies sold, they also cheapen the book a bit and make it feel far more shallow than it is. As the Times review says, it’s a “profound masterwork” of strategy and intrigue, not a salacious tell-all of celebrity sex.
However, as Holiday often says, “You have to meet people where they are,” and Gawker’s post of a highlight reel of Hogan’s sex tape garnered five million page views, proving once again what the public really wants.
Christopher Pierznik is the worst-selling author of nine books. His work has appeared on XXL, Cuepoint, Business Insider, The Cauldron, Fatherly, Hip Hop Golden Age, and many more. Connect on Facebook. Please feel free to get in touch at CPierznik99@gmail.com.
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