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Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue by Ryan Holiday
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“You rush in to stamp out the sparks and end up fanning them into flames. This is the risk.”
Ryan Holiday, Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue
“It’s the logic of two campers and the bear—you don’t need to be faster than the bear, just faster than the other camper.”
Ryan Holiday, Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue
“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.”
Ryan Holiday, Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue
“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. This choice defines us. Puts us at a crossroads with ourselves and what we think about the kind of person we are. “Anyone who is threatened and is forced by necessity either to act or to suffer,” writes Machiavelli, “becomes a very dangerous man to the prince.” And Peter Thiel was driven into a desperate position, of and not of his own making, that had started with a matter of his identity and become about a deeper identity. Now he had not only decided to act against Gawker, but he would conspire to destroy them.”
Ryan Holiday, Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue
“someone,”
Ryan Holiday, Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue
“The gating resource here was not capital,” Thiel said. “The gating resource was the ideas and the people and executing it well. It’s not like lawsuits haven’t been brought in the past. It’s something that’s been done, so we were required to think very creatively about this space, what kind of lawsuit to bring.” Most of the ideas do not stand up to scrutiny, or to Thiel’s ambitions. A slap on the wrist from the FCC about affiliate commissions will accomplish little. Exploiting the financial misdeeds of the company would likely require an inside man, and this would be nasty, deceitful business. It wasn’t just a question of which strategy might actually win, it was also figuring out which one could actually do real damage. “It was important for us to win cases,” Thiel said. “We had to win. We had to get a large judgment. We did not want to bring meritless cases. We wanted to bring cases that were very strong. It was a very narrow set of context in which you could do that. You did not want to involve political speech, you did not want to involve anything that had anything remotely connected to the public interest. Ideally, our cases would not even involve the First Amendment at all.” The First Amendment was unappealing not because Thiel is a libertarian, though he is, but because as a strategist he understood that it was Gawker’s strongest and most entrenched position: we’re allowed to say anything we want. It challenges the legal system and conventional wisdom where they are the most clearly established. Forget the blocking and tackling of proof and precedent. At an almost philosophical level, the right to free speech is virtually absolute. But as Denton would himself admit to me later, free speech is sort of a Maginot Line. “It looks formidable,” he said, “it gives false confidence to defenders, but there are plenty of ways around if you’re nimble and ruthless enough.” That’s what Thiel was doing now, that’s what he was paying Charles Harder to find. Someone from Gawker would observe with some satisfaction to me, many years away from this period of preliminary strategizing from Thiel, that if Thiel had tried to go after Gawker in court for what it had written about him, litigating damages and distress from being outed, for example, he certainly would have lost. This was said as a sort of condemnation of the direction that Thiel ultimately did attack Gawker from. Which is strange because that was the point. The great strategist B. H. Liddell Hart would say that all great victories come along “the line of least resistance and the line of least expectation.” John Boyd, a fighter pilot before he was a strategist, would say that a good pilot never goes through the front door. He wins by coming through the back. And first, that door has to be located.”
Ryan Holiday, Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue
“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”
Ryan Holiday, Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue
“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”
Ryan Holiday, Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue
“The line from the Obamas was “When they go low, we go high.” It’s a dignified and impressive mantra, if only because for the most part, whether you liked them or not, it’s hard to deny that they followed it. But the now cliché remark should not be taken conclusively, for it makes one dangerous omission. It forgets that from time to time in life, we might have to take someone out behind the woodshed. How we have lost this. How squeamish we have become. We now blindly demonize what is often one of the most effective forms of action. How vulnerable this ignorance has made us to the few real conspiracies, successful or not, that exist in the world. In this rare occasion, though, we got a glimpse, a peek behind the curtain, as the title of Gawker’s last post put it, of how things work. Now we know. Peter showed us. And yet our instinct is to turn away, to put our fingers in our ears. It’s why not once in nearly a decade of concentrated effort and scheming directed at a single enemy—at an entity who was obsessively covered and followed by the media—by an opponent who publicly stated his undying hatred of that enemy, did a single spectator, victim, or even many of the participants suspect any of what you read in the pages of this book. There is no question that what Thiel did over those years was brilliant, cunning, and ruthless. It is equally true that Gawker mostly beat itself. Denton and company allowed this to happen. Even the most cynical and aggressive media site on the planet had missed what was happening right in front of them; they did nothing to save themselves. “The idea of a conspiracy,” Thiel would say to me, “is linked with intentionality, with planning, working towards longer-term goals. In a world where you don’t have conspiracies maybe also those things disappear.”
Ryan Holiday, Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue
“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”
Ryan Holiday, Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue
“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.”
Ryan Holiday, Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue
“but it was the evil nature of our enemy that was somehow super galvanizing.”
Ryan Holiday, Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue
“Thiel, what ties them together really is Gawker and what they’d come to feel about it. Gawker had not only incited a conspiracy, but in the course of the trial, its actions, its tone, its arrogance had fused its unknown, unnamed opponents together”
Ryan Holiday, Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue
“Mr. A had said the more they studied Gawker, the more they interacted with this organization, the harder it was to see any redeeming qualities: because of what Gawker’s writers would say, how its lawyers acted, and everyone’s inability to show even a slight understanding of what Terry Bollea was so upset about.”
Ryan Holiday, Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue
“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.”
Ryan Holiday, Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue
“The Russians call this maskirovka—the art of deception and confusion. It is as old as strategy itself. Undermine your enemy, Sun Tzu advised 2,500 years ago. “Subvert him, attack his morale, strike at his economy, corrupt him. Sow internal discord among his leaders; destroy him without fighting him.” Call down the fog of war, he was telling conspirators and generals and swordsmen, let it descend on your opponent until they cannot see what is right before them. Because “all warfare,” Sun Tzu reminds us, “is based on deception.” Not just keeping secrets—that’s the first part, the passive part, a refusal to reveal your true intentions—but active, outwardly focused deceit intended to disorient and weaken the enemy. The long-term strategic drive to a decisive legal action—the hope of taking a case against Gawker to a real jury of normal people outside the Manhattan media bubble—had been set by Peter Thiel early on. By 2012, not only was the ideal case found with which to execute this strategy, but a lawsuit was filed within days of discovery. As the case wound its way through the legal system in 2013, it had seen many setbacks, some expected and others not, but these setbacks were not without their upside. They had, in the end, created a scenario in which the case’s final home in Florida district court might spell a bankruptcy-level event for Gawker Media.”
Ryan Holiday, Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue
“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.”
Ryan Holiday, Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue
“Grandmaster José Raúl Capablanca”—Thiel’s favorite chess player—“put it well: to succeed ‘you must study the endgame before everything else.”
Ryan Holiday, Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue
“The job of a journalist would be unbearable if one was always to put oneself in the shoes of a subject.”
Ryan Holiday, Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue
“This is the nature of the American legal system, and of conspiracy as well. It’s slow, adversarial. Moral quandaries and personal issues are reduced to brief moments and decided on small points of law. Even a winning case will likely see as many setbacks as it does victories, and it falls upon the constitution of the players to weather the former to get to the latter. And this isn’t even the real legal battle—these are just arguments over the attempts to obtain what is called “prior restraint” of speech. The conspirators were trying to get the tape taken down before—until—they’d won their case. Harder’s thinking was that a sex tape recorded without consent was so egregious that a judge would be sympathetic. Gawker’s lawyers enjoy disabusing their opponent of this notion. So does the judge.”
Ryan Holiday, Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue
“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.”
Ryan Holiday, Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue
“This is a book for a world that has come to think like Nick Carraway, riding in disbelief through life on the wake of conspiracies we won’t believe until we see, unable to comprehend why they happen and who makes them happen. This ignorance of how things really work is depressing to me. Because it opens us up to manipulation. It closes us off from opportunities to produce fruitful change and advance our own goals. It is time to grow up.”
Ryan Holiday, Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue
“When personal gossip attains the dignity of print, and crowds the space available for matters of real interest to the community,” future Supreme Court justice Louis Brandeis wrote in the Harvard Law Review in 1890, in a piece which formed the basis for what we now know as the “right to privacy,” it “destroys at once robustness of thought and delicacy of feeling. No enthusiasm can flourish, no generous impulse can survive under its blighting influence.” Brandeis’s words reflected some of the darkness of Kierkegaard’s worries from fifty years earlier and foretold some of that sullying paranoia that was still to come fifty years in the future. Thiel had read this article at Stanford. Many law students do. Most regard it as another piece of the puzzle that makes up American constitutional legal theory. But Peter believed it. He venerated privacy, in creating space for weirdos and the politically incorrect to do what they do. Because he believed that’s where progress came from. Imagine for a second that you’re the kind of deranged individual who starts companies. You’ve created cryptocurrencies designed to replace the U.S. monetary system that somehow turned into a business that helps people sell Beanie Babies and laser pointers over the internet and ends up being worth billions of dollars. Where others saw science fiction, you’ve always seen opportunities—for real, legitimate business. You’re the kind of person who is a libertarian before that word had any kind of social respectability. You’re a conservative at Stanford. You’re the person who likes Ayn Rand and thinks she’s something more than an author teenage boys like to read. You were driven to entrepreneurship because it was a safe space from consensus, and from convention. How do you respond to social shaming? You hate it. How do you respond to petulant blogs implying there is something wrong with you for being a gay person who isn’t public about his sexuality? Well, that’s the question now, isn’t it?”
Ryan Holiday, Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue
“First, a slight of some kind, which grows into a larger dissatisfaction with the status quo. A sense that things should be different, and will be different, except for the worse, if something doesn’t change. But then comes a second step, a weighing of the stakes. What if I do something about this? What might happen? What might happen if I do nothing? Which is riskier: to act or to ignore? History is uncertain on this question, as were the people in Peter’s life, the ones trying to tell him that there wasn’t much that could be done. Peter would, at one point, pass me a copy of The Fifteen Decisive Battles of the World by Sir Edward Shepherd Creasy, the book he had read as he’d mulled his options over. The epigraph to the chapter on the Battle of Valmy quotes Shakespeare: A little fire is quickly trodden out, Which, being suffered, rivers cannot quench.”
Ryan Holiday, Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue
“It is just one word: Conspiracies. What follows is Machiavelli’s guide for rising up against a powerful enemy, for ending the reign of a supposed tyrant, for protecting yourself against those who wish to do you harm. It is appropriate that such a book sits just within arm’s reach of one of Thiel’s wingback armchairs and not far from the chess set which occupies considerable amounts of his time. Something in these pages planted itself deep into Thiel’s mind when he first read it long ago, and something in Thiel allowed him to see past Machiavelli’s deceptive warnings against conspiracies and hear the wily strategist’s true message: that some situations present only one option. It’s the option available to many but pursued by few: intrigue. To strategize, coordinate, and sustain a concerted effort to remove someone from power, to secretly move against an enemy, to do what Machiavelli would say was one of the hardest things to do in the world: to overthrow an existing order and do something new. To engage in a conspiracy to change the world.”
Ryan Holiday, Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue
“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.”
Ryan Holiday, Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue
“Twenty-five hundred years ago, Thucydides would say that the three strongest motives for men were “fear, honor, and self-interest.” Fear. Honor. Self-interest. All covered. Which is the truest of them for Thiel? Does it matter? Someone had begun to think seriously that something needed to be done and believed that he might be the person to do it.”
Ryan Holiday, Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue
“Every conspiracy is a story of people. The protagonists of this one are two of the most distinctly unique personalities of their time, Nick Denton and Peter Thiel. Two characters who, not unlike the cowboys in your cliché western, found that the town—whether it was Silicon Valley or New York City or the world’s stage—was not big enough for them to coexist. The gravitational pull of the two figures would bring dozens of other people into their orbit over their ten-year cold war along with the FBI, the First and Fourth Amendments, and soon enough, the president of the United States. It somehow dragged me in, too. In 2016, I would find myself the recipient of unsolicited emails from both Peter Thiel and Nick Denton. Both wanted to talk, both were intrigued to hear I had spoken to the other. Both gave me questions to ask the other. And so for more than a year, I spent hundreds of hours researching, writing about, and speaking to nearly everyone involved. I would read more than twenty thousand pages of legal documents and pore through the history of media, of feuds, of warfare, and of strategy not only to make sense of what happened here, but to make something more than just some work of contemporary long-form journalism or some chronological retelling of events by a disinterested observer (which I am not). The result is a different kind of book from my other work, but given this extraordinary story, I had little choice. What follows then are both the facts and the lessons from this conflict—an extended meditation on what it means to successfully conspire, on the one hand, and how to be caught defenseless against a conspiracy and be its victim, on the other. So that we can see what power and conviction look like in real terms, as well as the costs of hubris, and recklessness. And because winning is typically preferable to losing, this book is about how one man came to experience what Genghis Khan supposedly called the greatest of life’s pleasures: to overcome your enemies, to drive them before you, to see their friends and allies bathed in tears, to take their possessions as your own. The question of justice is beside the point; every conqueror believes their cause just and righteous—a thought that makes the fruits taste sweeter.”
Ryan Holiday, Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue
“Machiavelli writes that a conspiracy without any coconspirators is not a conspiracy. It’s just a crime. This is also basic legal principle. If you kill someone by yourself, in the heat of the moment, it’s murder. If you meticulously plan it with someone else beforehand, that’s conspiracy. Lee Harvey Oswald almost certainly assassinated John F. Kennedy by himself. What he hoped would happen as a result is unclear. John Wilkes Booth conspired not only to assassinate Abraham Lincoln, but working with Lewis Powell and George Atzerodt also aimed to assassinate Andrew Johnson and William Seward. It was a coordinated attempt by Confederate sympathizers to usurp the United States government. It’s not simply a single crime, but a crazed, desperate effort to turn back the tide of a lost war. In his definitive book on the subject of strategy, Lawrence Freedman writes that “combining with others often constitutes the most strategic move.” By definition, the first move in the act of a conspiracy is the assemblage of allies and operators: your coconspirators. Someone to do your bidding, to work with you, someone you can trust, who agrees with you that there’s a problem, or is willing to be paid to agree with the sentiment that it’s about time someone, somebody did something about this. Each hand doesn’t need to know what the other is doing, but there needs to be more than one set. Thus, Thiel’s vague idea to do something about Gawker is concretized into conspiracy on April 6, 2011. It began unremarkably, when Thiel traveled to Germany to speak at a conference and had dinner with a student he’d met on a tour of a university a few years before. Peter arrives, driven in a black S-class Mercedes, the same model he has idling outside with a driver, twenty-four hours a day, seven days a week, wherever he is in the world.”
Ryan Holiday, Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue
“The historian E. P. Thompson said that history never happens as the actors suspect, that history is instead the “record of unintended consequences.” The assassination of Julius Caesar does not restore the Roman Republic, it leads to a brutal civil war and, at the end, another emperor. The Allied powers destroy Hitler and Germany but empower Russia and Stalin and create a new Cold War to follow the conclusion of the hot one. There is always something you didn’t expect, always some second-or third-order consequence. Peter Thiel’s conspiracy had achieved its intended outcome. A negotiated peace had been found. Gawker.com would cease to publish. A new leader was in charge of the rest of the sites, some of the offending articles would be removed. But what would the consequences, intended and otherwise, of it all be? What had this brilliant, independent mind neglected to see? What, if anything, would come as a surprise? His own power and strength for one.”
Ryan Holiday, Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue

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