Conspiracy Book Cover Conspiracy
Ryan Holiday
Biography & Autobiography
February 27, 2018

I am a Ryan Holiday fan-boy. I just want to be clear. I love how he writes. This book is a bit of a departure for him. It was enjoyable.

In 2007, Gawker Media, outed PayPal founder and billionaire investor Peter Thiel as gay. Thiel's didn't consider himself a public figure, and believed the information was private.

This lead to a decade-long, "meticulously plotted conspiracy" that would end nearly a decade later with a $140 million dollar judgment against Gawker, its bankruptcy and with Nick Denton, Gawker's CEO and founder, out of a job.

Why had Thiel done this? How had no one discovered it? What would this mean--for the First Amendment? For privacy? For culture?

It's a study in power, strategy, and one of the most wildly ambitious--and successful--secret plots in recent memory. I agree with the outcome. I am not 100% sure it was right.

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.

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.

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.

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.

What Denton did, in effect, was turn writing, social commentary, and journalism into a video game. Writing wasn’t a craft you mastered. It was a delivery mechanism. The people and companies you wrote about, like Peter Thiel, weren’t people, they were characters on a screen—fodder for your weekly churn. And the people you got to read this writing? They were points. The score was right there next to your byline. Views: 1,000. 10,000. 100,000. 1,000,000. The highest prize, the best ticket to traffic? Scandalum magnatum— going after great men and women.

“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.”

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.

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

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.

One of the most profound intellectual influences on Peter Thiel is a French thinker named René Girard, whom he met while at Stanford and whose funeral he would eventually speak at in 2015. Girard’s theory of mimetic desire holds that people have no idea what they want, or what they value, so are drawn to what other people want. They want what other people have. They covet. It’s this, Girard says, that is the source of almost all the conflict in the world.

“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.”

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.

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. Friction is when your trusted research tells you one thing but you come to find the situation on the ground is completely different, that the data had it all wrong.

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 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.

It’s the writers who stayed, year after year, then, who de-fined the culture. The effect of this over time was that Gawker was staffed by the kind of impolite, impolitic people who could not work at your average company.

Culture eats strategy.

“The terrible thing about people like you is that decent people have to become so much like you in order to stop you—in order to survive.”

The great sin for a leader, Frederick the Great once observed, was not in being defeated but in being surprised.

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.” A point where, if blindly ridden past, flush with the momentum of winning and strength, you imperil everything you have achieved. 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.

Scipio Africanus, the general who defeated Hannibal, would say that an army should not only leave a road for their enemy to retreat by, they should pave it. The Romans had a name for this road, the Gallic Way.

There is always something you didn’t expect, always some second- or third-order consequence.

The nineteenth-century French economist and libertarian thinker Frédéric Bastiat would say there is just one difference between a good economist and a bad one. “The bad economist confines himself to the visible effect; the good economist takes into account both the effect that can be seen and those effects that must be foreseen.”

Thiel’s friend Eric Weinstein would observe that you “can’t just exact revenge at no cost to yourself.” For Thiel, the unintended consequences were there, and the costs were not cheap. But there was also success. He had done what he had set out to do, and in fact done much more than he could have reasonably anticipated. He had changed media. He had created a pivot point in culture and it had worked. He would end this story at the place so well captured at the end of one of his favorite novels, Arthur C. Clarke’s The City and the Stars: “There is a special sadness in achievement, in the knowledge that a longdesired goal has been attained at last, and that life must now be shaped towards new ends.”