Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue - by Ryan Holiday

Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue – by Ryan Holiday

How strongly I recommend it: 7/10
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Go to the Amazon page for details.
Entertaining read full of intrigue. It shows you the whole plot behind the scenes.


Conspiracy entails determined, coordinated action, done in secret—always in secret—that aims to disrupt the status quo or accomplish some aim.
Nick Denton, whom you will come to know in these pages, is a kind of freethinker who has always held that the things other people are afraid to say are precisely the ones that need saying most.
Perhaps we have too few conspiracies, not too many. Too little scheming, rather than too much. What would happen if more people took up plotting, coordinating how to eliminate what they believe are negative forces and obstacles, and tried to wield power in an attempt to change the world? We could almost always use more boldness, and less complacency. We could use less telegraphing of our intentions or ambitions and see what secrecy, patience, and planning might accomplish. We could use a little more craziness and disruption, even from the people we disagree with.
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.
Machiavelli said that a proper conspiracy moves through three distinct phases: the planning, the doing, and the aftermath. Each of these phases requires different skills—from organization to strategic thinking to recruiting, funding, aiming, secrecy, managing public relations, leadership, foresight, and ultimately, knowing when to stop. Most important, a conspiracy requires patience and fortitude, so much patience, as much as it relies on boldness or courage.
The question that remains: What would a world without these skills look like? And would a world with more of them be a nightmare or something better?
The distinction between a conspiracy and a feud is as much in the time it takes for one to spring into action as it is in the type of action that one takes. In a fight, one responds to a punch by throwing a punch. In a conspiracy, one holds their punches and plots instead for the complete destruction of their antagonist, while often intending to escape with knuckles unbloodied and untraceable prints. Fights break out. Conspiracies brew.
These are the essential beginnings of a conspiracy. 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?
The Fifteen Decisive Battles of the World by Sir Edward Shepherd Creasy, the book he had read as he’d mulled his options over.
This buzzing frustration, this warmness in his cheeks is not a familiar feeling to the adult life of Peter Thiel. His anger is at odds with the cautious mind that is his nature; he is not a man prone to being ruled by his emotions. If someone asks him a question—say, about some controversial issue of the day—he does not simply react with an opinion, or pluck a conclusion from nowhere. Instead, he begins with, “One view of these things is that . . . ,” and then proceeds to explain the exact opposite of what he happens to personally believe. Only after he has finished, with complete sincerity and deference, describing how most people think about the issue, will he then give you his opinion, which almost always happens to be something radically unorthodox—all of it punctuated with liberal pauses to consider what he is saying as he is saying it.

CHAPTER 3 Turning to Conspiracy

Machiavelli said that conspiracies were weapons of the people. Only princes could afford to send an army against another army, he observed, but a conspiracy is available to every man. Which is why it is usually the desperate who turn to conspiracy and why the powerful fear them so much.
It is the weaker party who relies on secrecy and surprise and “low tactics.” Because they have to.
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.

CHAPTER 4 Assembling the Team

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.
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.
The butterflies settle. The conversation has wound itself down naturally and now there is nothing left but for Mr. A to seize the moment. This moment that few get. The chance for a pitch that can change your life. There is something popular with ambitious people called the “briefcase technique.” You don’t show up to a meeting with a few vague ideas, you have a full-fledged plan that you take out of your briefcase and hand to the person you are pitching. Even if nothing comes of this plan, the person on the other side is knocked over by your effort, so impressed by the unexpected certainty that they cannot help but see your usefulness to them. Mr. A unlocks that figurative briefcase on the table: “Okay, I know what you think about Gawker, here’s what I am proposing. . . .”
Ambition and opportunity have collided and the kid in front of him is proposing a solution to that problem that Thiel has set upon trying to solve: Peter should create a shell company to hire former investigative reporters and lawyers to find causes of action against Gawker. Gawker has written thousands of articles about thousands of people; it must have made a mistake somewhere. Mr. A’s proposal is more than just an idea, it’s a comprehensive, structured plan: he has researched some names, he has a timeline and a budget.
Here is where the ambition and naïveté of youth are so powerful. Mr. A responded with words that were absurd for someone of his age, someone who in fact knew little about the world except from what he had read and learned in school. Except he was right and the words he spoke were the type a man like Thiel could not resist. “Peter, if everyone thought that way, what would the world look like?” “Just hearing that was so refreshing,” Peter would say later, “because of course what you always heard were these incremental things that wouldn’t quite do it.”
It is more than the servant whispering to Darius, “Master, remember the Athenians.” It is Peter, think about all the people they’ve hurt. It’s going to keep happening. It’s only going to get worse. If you—the billionaire—can’t do anything about it, who can?
The professional son understands what every father wants—a progeny worth his time, someone to invest in, someone who can further his legacy. The professional father wants to see his greatness given a second body—a younger one, with more energy, with the benefit of his hard-won experiences. Peter was then not married, and he has no children. There is a loneliness there.
Rooted in every conspiracy is often shared loneliness, a smoldering frustration or bitterness. Of not being listened to. Of the world not understanding. Two people come together and this smoldering becomes the small flicker of a flame for the first time. Someone shares this with me. I am not alone. Two is more than one and can become three, four, five quickly. And so across the table at that restaurant in Berlin, the conspiracy begins.
He wouldn’t want to just spout off. But if he thinks he has some deep idea about human nature, about the market, he’ll go all in.
With his first hire, Thiel’s conspiracy is stronger, by virtue of simply existing, yet it is also naturally weaker. This is the risk of combining with allies. The strategic benefit of adding a new coconspirator comes at the cost of substantially increasing the chance of getting caught. While you do want to find the right people . . . you typically want as few of them as possible.
The image of Silicon Valley is that the start-up comes together quickly, from idea to minimum viable product to world-changing business in a montage of exciting steps. In truth, like conspiracies, it takes a little longer. The path can be meandering. PayPal’s anti-fraud insights took several years to become Palantir. Thiel had registered the name before he truly founded the company that looked for outside investment. Even Peter’s hedge fund had been something he’d started before PayPal and only came back to after PayPal. Thiel calls this the prehistory of a company, of a conspiracy.
And what does Harder see in this twenty-something who has come into his office, who alternates between fantastical certainty and obsequious flattery? He sees the same thing that Peter Thiel sees in the professional son: an opportunity, energy, raw potential, and talent.
In the search for collaborators, hunger is an essential qualification. While it’s dangerous to conspire with people who have a lot to lose, you can’t conspire without someone who is afraid to bet on themselves, who isn’t willing to take a big stake on something that very well could fail. Where these two traits overlap there is often a sweet spot: the man or woman who has something to prove and something to protect, the strong sense of self-belief coupled with that killer instinct.
In the business of bringing down Gawker, Mr. A was the president, Harder was the CEO, and Thiel the majority shareholder who expected his men to mind his money and find the returns he is after. This is the model he likes to operate. Early in the two companies he cofounded, PayPal and Palantir, Thiel would install strong CEOs and leaders. He relies on what might be called the plenipotentiary model—empowering trusted, skilled people on his behalf to execute the bold vision he has created. In Mr. A and Harder, he needed representatives whose judgments were close enough to his own that he could be confident in his ignorance of specific issues and deploy them to the places he couldn’t go, trusting them to discern which decisions were important enough to be made by Thiel alone.

CHAPTER 5 Finding the Back Door

We are often taught that successful strategy is a matter of boldness, but it has also always been the case that it’s as much a matter of patience and due diligence as it is of noticeable action.
“With patience and resources,” Mr. A would come to say often on his weekly calls with Peter, “we can do almost anything.” Tolstoy had a motto for Field Marshal Mikhail Kutuzov in War and Peace—“Patience and Time.” “There is nothing stronger than those two,” he said, “. . . they will do it all.” In 1812 and in real life, Kutuzov gave Napoleon an abject lesson in the truth of that during a long Russian winter.
Editorially, Nick Denton wanted to be first—which is a form of power in itself. But this isn’t how Thiel thinks. He would say his favorite chess player was José Raúl Capablanca, and remind himself of the man’s famous dictum: To begin you must study the end. You don’t want to be the first to act, you want to be the last man standing.
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.
Peter seems to have a preternatural ability to sense which lever to pull, what angle is the best approach, and it’s almost always something radically different from what your average person would select. He wasn’t looking for an opportunity to score a few points against Nick Denton, but trying to locate some singular button that would be the man’s undoing. An investor tells me that with each investment, Peter Thiel likes to ask: What do I know about this company that other investors don’t know? In other words: Do we have an edge? It’s only with some sort of informational asymmetry, goes the thinking, that one can not only beat the market but dominate it, and get the kind of return that takes a $500,000 check and turns it into a billion.

CHAPTER 6 Tear Out Your Heart

There are perpetrators and victims in a conspiracy, heroes and villains. The chess pieces are not ivory vessels on boards like those that decorate Thiel’s homes and offices, they are people. And yet, to further one’s ends, these people cannot be treated as people. To recoil at this thought is natural. While Machiavelli never said—as some might claim—that we must lose that part of ourselves altogether in the pursuit of power, he did say that for the prince who wishes to remake the world to his liking, the natural impulse to be kind, forgiving, and empathetic must temporarily be suppressed. This is not an easy thing to do, even in the face of overwhelming necessity.
Or so we tell ourselves. The ends justify the means.

CHAPTER 7 Seizing the Sword

Machiavelli’s warning once again rings prophetic: “Anyone who is threatened and is forced by necessity either to act or to suffer becomes a very dangerous man to the prince.”

PART II The Doing

CHAPTER 8 Prepare for Setbacks

A conspiracy meets with more setbacks than successes. It’s rolling the dice—making a decision, knowing that unforeseen issues will come up. Lots of them.
“If you think of what you’re doing too probabilistically where you have all these different steps, and there’s a chance that all these steps fail, then the conspiracy is very complicated, like a Rube Goldberg contraption, where something is just going to break down for one reason or another,” Peter explains. “What Mr. A convinced me of in 2011 was that this is not a statistical concatenation of probabilities—it was that if we simply executed on a few of these things correctly you would win.”
it had not occurred exactly as expected, but that’s how it goes. “You take two steps forward and one backwards but as long as you’re progressing that’s what matters,” said Mr. A.

CHAPTER 9 Know Thy Enemy

The great Sun Tzu said that you must know your enemy as well as yourself. To not know yourself is dangerous, but to not know your enemy is reckless or worse. Because without this knowledge, you are unaware of the opportunities your enemy is presenting to you, and worse, you are ignorant of the opportunities you present to those who wish to do you harm.
Deterrence is an important strategy. The more intimidating you are, the less people conspire against you. Yet the powerful must always be very careful with their threats, with their demonstrations of superior resources. Aimed poorly, they have a nasty habit of backfiring.

CHAPTER 10 The Power of Secrets

Secrecy has always been the essential element in conspiracies. It is, after all, very hard to have a secret plan you’ve told everyone about. For obvious reasons, it’s more difficult to destroy someone or something when they know you’re coming for them.
When people who don’t like what you’re doing know that you’re trying to do it, they are more likely to be able to stop you. It’s that simple.
Secrecy is not just the best option, it’s the only one.
Peter had learned from his early experiences with Gawker and the media that those with unconventional beliefs should probably keep most of what they think to themselves. But a conspiracy is more than just an unusual opinion. Thiel’s strategy inherently depends on secrecy. The various coconspirators see only what Peter allows them to see.
The troops can’t and shouldn’t know everything the general is doing, which means the general stands alone and suffers alone. The less the conspirators know about the leader’s plans, the less likely they are to expose them—the less likely they are to undermine or question them. The less likely it is that the enemy will find out and block them.
In every conspiracy, there is temptation to talk, especially as you near your goal. The weight of silence and deceit begins to weigh on the participants.
“Psychologically, there is this weird thing where you want to brag about these things that you’re not supposed to,” Thiel would say to me. Freud explained this phenomenon a hundred years ago: “He that has eyes to see and ears to hear may convince himself that no mortal can keep a secret. If his lips are silent, he chatters with his finger-tips; betrayal oozes out of him at every pore.” This is how Peter justified the few friends he told and how he suspects he was eventually discovered. Just as rules are meant to be broken, it seems, secrets are meant to be shared. Even benign conspiracies are revealed this way, through the irresistibility of telling someone, anyone. The author J. K. Rowling’s pseudonym “Robert Galbraith”—which she conceived of with her publisher and attorney so she might write other fare without the weight of Harry Potter expectations sinking the chances of its success—was revealed when her lawyer told a friend of his wife’s who promptly gave the secret away on Twitter. Robert Greene: “The main weakness in any conspiracy is usually human nature: the higher the number of people who are in on the plot, the higher the odds that someone will reveal it, whether deliberately or accidentally.”
A conspirator cannot tell someone they’re coming for them, even if they ask you directly, “Are you coming for me?” The endeavor is already difficult enough, the odds far enough outside one’s favor, that to give advance notice would likely be fatal. The fox must outsmart the lion, it must avoid the snare the hunters set for it.
“Anyone who has a guilty conscience can easily be led to believe that people are talking about him,” Machiavelli warns conspirators. “A word with another meaning is overheard which shakes your courage and makes you think it was said with respect to your plans. The result is that you either reveal the conspiracy yourself by fleeing or you confuse the undertaking by acting at the wrong time.”

CHAPTER 11 Sow Confusion and Disorder

Being feared, Machiavelli says, is an important protection against a conspiracy. The ultimate protection, he says, however, is to be well liked. Not simply because people who love you are less likely to want to take you down, but because they are less likely to tolerate anyone else trying to, either.

CHAPTER 12 The Ties That Bind

Most conspiracies are not found out. They are betrayed. Or they collapse from within, a betrayal of the cause itself.
he secrecy of a conspiracy and its execution, then, is not purely a matter of planning and discipline, but also a matter of the bonds that bind the conspirators together. Once you get everyone on the bus, how do you keep them onboard? How do you reward them for loyalty? How do you get the best out of them? How do you trust them, knowing as you do the lengths to which they’re willing to go and secrets they’re willing to keep?

CHAPTER 14 Who Wants It More?

There is a story about a young John D. Rockefeller who found himself stuck with bullying, corrupt business partners. He wants to break with them, but he can’t, because they control the votes. They are squeezing his business to death. They abuse him, talk about forcing him out. What is he to do? Quietly, Rockefeller lines up financing from another oilman and waits. Finally there is a confrontation; one of them tries to threaten him: “You really want to break it up?” Yes. He calls their bluff. They go along, knowing that the firm’s assets will have to go to auction. They’re sure they’ll win—Rockefeller doesn’t have that kind of money. He bids, they bid, he bids, they bid. Rockefeller wins the auction. A few weeks later, the newspapers announce his new partnership—revealing who had backed his bid—and the news that Rockefeller is, at twenty-five, an owner of one of the largest refineries in the world. On that day his partners “woke up and saw for the first time that my mind had not been idle while they were talking so big and loud,” he would say later. They were shocked. They’d seen their empire dismantled and taken from them by the young man they had dismissed. Rockefeller had wanted it more.

PART III The Aftermath

CHAPTER 15 The Battle for Hearts and Minds

Machiavelli would say that when overconfidence enters men’s hearts, “it causes them to go beyond their mark . . . to lose the opportunity of possessing a certain good by hoping to obtain a better one that is uncertain.” In plain language: perfect is the enemy of good (or good enough). Clausewitz warned generals about the “culminating point of victory.”
The decision to attack one additional city, to charge after the enemy who has retreated, or to extend the battle for one more day might not just be subject to diminishing returns, it might snatch defeat from the jaws of victory. Every conspiracy runs this risk, and often, the conspirators know they have passed it only after it is too late.
Machiavelli warns conspirators that the most dangerous time is after the deed is done. It is as if Peter and Harder did not fully consider this. “We thought the point of maximum tension would be the trial and once we were done with that, you know, if they couldn’t figure it out at the trial they never would,” Peter says. He would also say that he thought the end of the trial would put them past the “point of maximum danger.” In fact, this was exactly the point of the highest vulnerability. Loss inherently makes the loser sympathetic. We can easily be made to feel bad for the person on the other side of a true catastrophe, even if just minutes before we thought they had it coming to them.
In a conspiracy that was so brilliantly planned and orchestrated, calculated in every way down to its probabilistic decimal point, where no expense was spared, this can’t be seen as anything but little and late. If we are to flash back to 2012, as Mr. A and Harder are meeting for the first time, as Thiel strategizes with them from afar, we find the roots of this mistake. They had considered so many different variables. They thought about Gawker’s weaknesses and how to exploit them. They explored a dozen different routes to the endgame—a decisive legal judgment against Gawker. But like so many conspirators, they seem not to have stopped to ask, Okay, then what?
Way back at the beginning, Thiel and Mr. A decided on limiting themselves to ethical and legal means of remedy against Gawker, because as Thiel had said, secrets often have expiration dates. Mr. A had begun exploring bankruptcy lawyers in anticipation of a favorable verdict as early as 2015, but he had made fewer preparations for a favorable verdict where the curtain was pulled back and the puppet masters revealed.
Thiel knew the importance of finishing. He had written it in Zero to One. “It is much better to be the last mover,” not the first mover. “Grandmaster José Raúl Capablanca”—Thiel’s favorite chess player—“put it well: to succeed ‘you must study the endgame before everything else.’” The conspirators had studied it, but only so far as their maneuvering took to get the other man’s king on its side. What they failed to consider was that in any chess match between masters, there is always more than one game. Each requires its own unique plan.

CHAPTER 17 The Art of Settling

Of the dangers after a successful conspiracy, Machiavelli would say, “there is only one, and that is when someone is left who may avenge the dead prince.” For this reason, Robert Greene warns, one must “crush your enemies totally.” Remember, after David fells Goliath with his well-placed stone, that’s not the end of it. Then began the gruesome work of hacking off the giant’s head with the man’s own sword. The point is: you can’t leave them even an inch to come back at you.

CHAPTER 18 There Are Always Unintended Consequences

In a time when computers are replacing many basic human functions, it will eventually come to be that audaciousness, vision, courage, creativity, a sense of justice—these will be the only tasks left to us. A computer can’t practice secrecy or misdirection, a computer can’t feel an urge to remake the world. Only humans can be that crazy. What you will do with this lesson, what ends you will put it to, are up to you. All I can say is that it is in these times of flux and upheaval that we may need that ambition most.