Great Reads: Conspiracy By Ryan Holiday

What does it mean to conspire against someone? How would you go about secretly plotting and planning to destroy your target? In the age of social media where every move is broadcasted to the world, is a real conspiracy even possible?  All valid questions when we think about what a conspiracy is. The word alone can conjure up many thoughts and theories about historical events, each seemingly wilder than the next, however, in the modern age the general public tends to believe they are no longer possible to achieve or exist (in the real world at least). In his newest book, Conspiracy, Ryan Holiday takes his readers on a journey as he illustrates an authentic plot that was both incredible and frightening when one thinks about the implications of the result. The possibilities of what can be done, and what can’t are put to the test as one’s resources are able to tip the scale of justice in their favor. 

Over the last year, Ryan Holiday has become one of my favorite authors, his writing is incredibly straightforward, his concepts are fascinating, and his books have an excellent re-reading value that most authors just can’t achieve. As a result of reading many of his books like, Ego is the Enemy (twice), Obstacle Is The Way, and Perennial Seller, I always try to stay up to date with what he puts out, even if it is a blog post. That’s why when I discovered he had a new book called Conspiracy, I was intrigued because this project seemed like it would be unlike any of his previous releases; I was correct in my assumption.

In this book, Ryan carefully followed a plot by billionaire tech investor Peter Thiel to destroy the insanely popular gossip blog, Gawker. In 2016 Gawker was forced to declare bankruptcy as a result of a 140 million dollar lawsuit by former pro-wrestler Hulk Hogan. At first glance of the story, I was confused at how every part of the equation fit. Peter Thiel was one of the early major investors of Facebook and a co-creator of PayPal, what did he have to do with Hulk Hogan, and why was Hogan suing a blog site for such a significant amount of money? It was up to me to read so this puzzle could be put together.

In 2007, Gawker published an article that would unleash the chain of events Conspiracy followed. The title of the article was, “Peter Thiel is totally gay, people.” Today celebrities are “exposed” so frequently that no one bats an eye when we the public are told something about a celebrity’s private life. It is the norm. However, in 2007 many people, including Thiel, were shocked when their personal business was made public at the whim of a blog who only saw their secrets as a means to gain traffic to their sites. Thiel’s sexual preference was described as an open secret in the tech community. He felt it was not essential to talk about, and why should he? Other people, mainly Gawker owner Nick Denton did not share the same sentiments. Denton, who is also a gay man, created Gawker with the belief that all information should be transparent and open to the public and was unapologetic about what he believed because the first amendment was a staple for his philosophy. Thus the stage for our story is set, two wealthy men, one a billionaire and another a millionaire, who have conflicting ideas would be on track for a head-on collision that would not come for almost another 10 whole years. 

The idea of a conspiracy is to carefully (and secretly) plan out the downfall of an adversary. Gawker had become very powerful as a media entity and had made a lot of enemies along the way. Peter Thiel was one of the more outspoken people who felt Gawker had gotten out of control. He felt something needed to be done, but everyone around him told him nothing could be. Instead of hoping and waiting, he decided to take matters into his own hands and eliminate this problem personally. 

As Ryan described Thiel’s train of thought while starting this plan, I likened this mindset into anything that required “thinking big.” Conspiracies don’t necessarily have to be negative, that is always based on perception. Many people have dreams of making something happen, like an invention, or a business, but never think it could be them to pull it off. Peter Thiel asked a question that has caused every important change in the world, “why not?” Why can’t you start that business, or invent that thing which will make everyone’s life easier? Why couldn’t Peter Thiel legally fight a blog which he felt was ruining the lives of others? This mindset is what Conspiracy was about. With years of planning and a bit of luck, Peter Thiel was able to covertly use his resources to put an end to a problem he felt would change the culture for the worst. 

In 2012, years after Thiel had been ousted as gay, a Gawker editor released a video on its site showing Hulk Hogan having sex with his best friend’s wife. The video had been filmed AND acquired illegally, and Hogan sued. Thiel and his co-conspirator “Mr. A” saw this as a perfect opportunity to put an end to Gawker and offered to fund Hogan’s case. He had no idea Peter Thiel; billionaire tech investor was responsible for covering his legal expenses. This detail, along with many other moves and countermoves, explained in the book led to the downfall of Gawker.  

So now what does this mean for the future of journalism and the first amendment?  Will other billionaires be able to now secretly fund legal cases to eliminate publications that speak ill about them? Will publishers (and writers) be afraid to cover stories in fear of retribution? Only time will tell, Ryan Holiday gives a fair and balanced analysis of what this could mean going forward, and also the motivations of the people involved. I highly recommend this book. Great Read.


Malcom X. Bowser is a writer, curator, and founder of Urban X.

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