Rating:  ☆☆☆☆

Recommended by:  Mike Brady

Author:   Ryan Holliday

Genre:    Nonfiction, Business, History, Politics, Biography

331 pages, published February 27, 2018

Reading Format:  Book

Summary

Conspiracy tells the tale of Peter Theil, Paypal founder and billionaire investor, and the conspiracy he funded to exact revenge on Gawker Media.   In 2007, in a short blogpost on Valleywag, Gawker outed Peter Thiel as gay.  While Thiel’s sexuality had been known to close friends and family, he didn’t consider himself a public figure and was incensed that his privacy had been invaded.  It took almost a decade, but Thiel finally exacted his revenge.  He financed a lawsuit by Hulk Hogan who sued Gawker for invasion of privacy after they posted a videotape of him having sex with his best friend’s wife.  Hogan would end up with a $140 million dollar judgment against Gawker which had declare bankruptcy.  Only later would Thiel’s role in bringing down Gawker become public.

Quotes 

“It is always revealing to see how a person responds to those situations where he’s told: “There’s nothing you can do about it. This is the way of the world.” Peter Thiel’s friend, the mathematician and economist Eric Weinstein, has a category of individual he defines as a “high-agency person.” How do you respond when told something is impossible? Is that the end of the conversation or the start of one? What’s the reaction to being told you can’t—that no one can? One type accepts it, wallows in it even. The other questions it, fights it, rejects it.”

 

“His path was in some ways traditional—Stanford to Stanford Law to judicial clerkship to high-powered law firm—but it was also marked by bouts of rebellion. At Stanford he created and published a radical conservative journal called The Stanford Review, then he wrote a book that railed against multiculturalism and “militant homosexuals” on campus, despite being both gay and foreign born. His friends thought he might become a political pundit. Instead he became a lawyer. Then one day, surprising even himself, he walked out of one of the most prestigious securities law firms in the world, Sullivan & Cromwell, after seven months and three days on the job. Within a few short years, Thiel formed and then sold PayPal, an online payments company, to eBay for $ 1.5 billion in July 2002, the month that Nick Denton registered the domain for his first site, Gizmodo. With proceeds of some $ 55 million, Thiel assembled an empire. He retooled a hedge fund called Clarium into a vehicle to make large, counterintuitive bets on global macro trends, seeding it with $ 10 million of his own money. In 2003, Thiel registered a company called Palantir with the Securities and Exchange Commission. In 2004, he would found it in earnest. The company would take antifraud technology from PayPal and apply it to intelligence gathering—fighting terrorism, predicting crime, providing military insights. It would take money from the venture capital arm of the CIA and soon take on almost every other arm of the government as clients.”

 

“You rush in to stamp out the sparks and end up fanning them into flames. This is the risk.”

 

“For all the claims that what Peter had done was personal and unethical and wrong, that he had made the world a worse place and horribly wronged a group of journalists, something surprising happened: Media actually did change. Because they knew they needed to.”

 

“The Count of Monte Cristo would put it better: “What a fool I was not to tear my heart out on the day when I resolved to avenge myself!” Ah, but what dangerous business this is. This artificial hardening is a dangerous crossroads, a bargain with our primal forces that not everyone escapes or can emerge from with clean hands. William James knew that every man is “ready to be savage in some cause.” The distinction, he said, between good people and bad people is “the choice of the cause.”

 

“Peter and a team of conspirators and a judge and a jury in Florida had spoken. They said: We don’t want to live in a world where the media can publish someone having sex—even if it’s just the “highlights”—simply because that person has talked about his sex life in public”

 

“We live in a world where only people like Peter Thiel can pull something so intentional and long-term off—and it’s not because, as Gawker has tried to make it seem, he’s rich. It’s because he’s one of the few who believes it can be done.”

 

“There is a moment in The Great Gatsby when Jay Gatsby introduces Nick Carraway to Meyer Wolfsheim, mentioning offhandedly that he is the man who fixed the 1919 World Series. The idea staggers Gatsby’s idealistic young friend. Of course, Carraway knew the series had been thrown. But “if I had thought of it at all,” he says, “I would have thought of it as a thing that merely happened, the end of some inevitable chain.” It was unbelievable to him then, as it is to us now, that a single person could have been responsible for changing the outcome of an event watched by some fifty million people. In real life, the 1919 World Series was fixed not by Wolfsheim, but with great skill and audacity by Arnold Rothstein, a Jewish gangster. A young lieutenant colonel in the U.S. Army named Dwight Eisenhower eagerly followed the game as the scores came in via telegram, and like everyone else, never suspected a thing. He would remark years later that the revelation of the conspiracy that had thrown the series produced a profound change in his perspective about the world; it taught him never to trust in first appearances.”

 

“The essayist and investor Paul Graham, a peer and rival of Peter Thiel’s, has charted the trajectory of a start-up, with all its ups and downs. After the initial bump of media attention, the rush of excitement from the unexpected success, Graham says that the founders enter a phase where the novelty begins to wear off, and they quickly descend from their early euphoria into what he calls the “trough of sorrow.” A start-up launches with its investments, gets a few press hits, and then smacks right into reality. Many companies never make it out of this ditch. “The problem with the Silicon Valley,” as Jim Barksdale, the former CEO and president of Netscape, once put it, “is that we tend to confuse a clear view with a short distance.” Here, too, like the founders of a start-up, the conspirators have smacked into reality. The reality of the legal system. The defensive bulwark of the First Amendment. The reality of the odds. They have discovered the difference between a good plan and how far they’ll need to travel to fulfill it. They have trouble even serving Denton with papers. Harder has to request a 120-day extension just to wrap his head around Gawker’s financial and corporate structure. This is going to be harder than they thought. It always is. To say that in 2013 all the rush and excitement present on those courthouse steps several months earlier had dissipated would be a preposterous understatement. If a conspiracy, by its inherent desperation and disadvantaged position, is that long struggle in a dark hallway, here is the point where one considers simply sitting down and sobbing in despair, not even sure what direction to go. Is this even possible? Are we wrong? Machiavelli wrote that fortune—misfortune in fact—aims herself where “dikes and dams have not been made to contain her.” Clausewitz said that battle plans were great but ultimately subject to “friction”—delays, confusion, mistakes, and complications. What is friction? Friction is when you’re Pericles and you lay out a brilliant plan to defend Athens against Sparta and then your city is hit by the plague.”

 

“The line attributed to the management guru Peter Drucker is that culture eats strategy. It’s a truism that applies as much to conspiracies as it does to businesses. It doesn’t matter how great your plan is, it doesn’t matter who your people are, if what binds them all together is weak or toxic, so, too, will be the outcome—if you even get that far. But if the ties that bind you together are strong, if you have a sense of purpose and mission, you can withstand great trials.”

My Take

Conspiracy was a captivating page turner.  Even though you know how it ends, the book still manages to create a great deal of suspense and wonder as to how Thiel and Hogan are going to pull off a legal win.  While I had previously read Ego is the Enemy by Ryan Holiday, I really preferred Conspiracy.  Holiday takes himself a bit too seriously at time, but he still manages to weave a compelling tale.