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. (Location 155)

Tags: conspiracy

Note: Conspiracies have three phases: Planning, doing & aftermath

“As a publishing entrepreneur who built an operation out of nothing, I had to go where the energy was,” Denton would say. That energy was mostly the energy of disillusioned youth, of outsiders criticizing insiders. In being anti this and that, and rarely for something else instead. Mankind has always crucified and burned, a great playwright once said. We take a secret pleasure in the misfortune of our friends, said another wise man. (Location 222)

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. But in a bind, and with so many posts to get out each day, ordinary people would do just as well. (Location 244)

Note: Denton turned writing into a computer game

For his bravado, Nick Denton was an incisive reader of other people. What he knew was that most people did not have the stomach—or the cash—to actually take it very far against a media outlet. He felt protected by the moat explained in the old twentieth-century proverb: Never fight a battle against someone who buys ink by the barrel. It’s easier to just let the whole thing go. (Location 306)

Tags: media

Note: Never fight a battle against someone who buys ink by the barrel

The Fifteen Decisive Battles of the World by Sir Edward Shepherd Creasy, (Location 506)

Tags: toread

Note: .toread

The kind of mathematical equation someone like Peter might consider would look something like this: if there is a 20 percent chance that Gawker will cost me $1 billion, then it makes perfect sense to spend up to $200 million trying to prevent that from happening. Negative expected value—it’s a calculation Wall Street guys make every day. (Location 541)

A start-up is, in Peter’s definition, “a small group of people that you’ve convinced of a truth that nobody else believes in.” (Location 896)

Tags: startup

Note: .startup

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. (Location 914)

Note: Plan to be the last man standing

read a public memo from Denton to his staff in mid-2010 that says, “The staples of old yellow journalism are the staples of the new yellow journalism: sex; crime; and even better, sex crime.” (Location 1071)

to think and to do are always different things. (Location 1143)

Tags: execution

Note: .execution

This ability to rope off your human side was exactly how Gawker’s writers and editors had learned to function. The writers were, as A. J. Daulerio would describe, “puppies that have been trained to bite—even people who came into the house.” Their job was turning part of themselves off, leaning into the lack of empathy, saying loudly the things considerate people would have been driven to soften or say only in a cupped whisper. If you wanted to be a great blogger, if you wanted to succeed in that environment, you had to. “The mortal sin at Gawker,” A.J. would tell me, “was not running a story that would hurt someone’s feelings.” (Location 1179)

Note: Gawker staff were like puppies trained to bite

choose your enemies wisely, he had been told, because you become just like them— (Location 1261)

Note: You become like your enemies

A Gawker writer would defend a similar story a few years later by saying, “Stories don’t need an upside. Not everyone has to feel good about the truth. If it’s true, you publish.” (Location 1415)

Note: If its true you publish

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. (Location 1805)

Tags: enemy

Note: .enemy know your enemy as well as yourself

“I believe in total freedom and informational transparency. I want everybody to know everything. And I think society, this country that I moved to will be better off if we could talk freely about everything. So that’s—I’m an extremist when it comes to that. That’s why I love the U.S. I love the presumption that the expression is free and I want to make fullest use of that liberty that the internet provides,” he said calmly to the camera. (Location 1887)

Note: Total freedom and transparency of information

“The things that I think I’m right about,” Thiel said, “other people are in some sense not even wrong about, because they’re not thinking about them.” In this sense, it’s an oversimplification to say that Gawker was wrong about the threat it faced. It was actually much worse. It was totally and utterly unaware of it—unaware of how much harder it was making it for itself with each decision, each misreading, each misjudgment. (Location 1985)

Note: Peope arent wrong because they arent even thinking about it

“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. (Location 2131)

Note: The more people that know of the plan, the greater the chance it will be revealed

“The truest way to be deceived is to think oneself more knowing than others” is La Rochefoucauld’s maxim. (Location 2189)

Most conspiracies are not found out. They are betrayed. Or they collapse from within, a betrayal of the cause itself. (Location 2474)

Note: Most conspiracys are betrayed or collapse from within

Gawker was staffed by the kind of impolite, impolitic people who could not work at your average company. This was their home, the island where they were not misfits. It was, as one longtime Gawker writer would say, a “fellowship of the weird and surly and otherwise unemployable, the culture of writers who couldn’t quite imagine being anywhere else, with anyone else.” (Location 2529)

It always takes longer than expected, per Hofstadter’s Law, even when—and this is the critical part—one takes Hofstadter’s Law into account. (Location 2709)

Tags: favorite

Note: Everything takes longer than expected

The great sin for a leader, Frederick the Great once observed, was not in being defeated but in being surprised. (Location 3332)

Note: A leader should not be surprised

perfect is the enemy of good (or good enough). (Location 3488)

Occam’s razor had set in (the simpler explanation is more likely) (Location 3528)

Tags: heuristics

Note: .heuristics

Harder told me that he found the media to be like a pack of crows, “If you kill a crow outside your house, the whole pack will descend upon you and never leave you alone. If you go for a walk, they will attack you. That’s the media that would help out Gawker.” (Location 3644)

Note: The media are like crows

an army should not only leave a road for their enemy to retreat by, they should pave it. The (Location 3728)

He learned another important lesson in that Florida courtroom, this one also about America—that average and ordinary people cared little for the assumptions of the so-called elites. I think he also learned something about his own willingness to put up a middle finger at those elites, and how vulnerable they might be. There was a pleasure in making these people howl, in taking real action and, as he had said, finding oneself capable of the power to “tell history to stop.” (Location 3805)

It would be a little more elegant if the reading public recognized their own contribution, that they get precisely the media that they click on and talk about.” (Location 3905)

amor fati—loving, embracing the good in what has happened. (Location 3940)

Tags: mindset

Goethe would say that many who clamor for freedom of the press do so in order to abuse it. (Location 3967)

Note: Those who want freedom of the press do so to abuse it

The line from the Obamas was “When they go low, we go high.” (Location 4023)

Note: Be dignified

For those who are upset and angry about what happened here, it’s worth asking: What are you really mad about? That a man, when attacked by a media outlet, pursued legal means of recourse in the justice system? Or are you upset that the media outlet would be so stupid as to flagrantly violate someone’s sexual privacy—contradicting its own grandstanding on the topic—and then not only refuse to apologize and make the situation right, but mount an aggressive but self-defeating legal strategy that gave a judge and jury no choice but to hold it accountable to the laws passed by the voters of Florida? Even with whatever good work Gawker’s reporters had done, is that recklessness and arrogance so worth protecting that it should come at the cost of Peter Thiel’s and Hulk Hogan’s access to the law? We should deprive them of their rights because they are rich? Because they have strange personal lives? Because we don’t like their politics? (Location 4073)

you want to have a different world, it is on you to make it so. It will not be easy to do it—it may even require things that you are reluctant to consider. It always has. Moreover, that is your obligation if you are called to a higher task. To do what it takes, to see it through. (Location 4103)

Note: If you want a different world its on you to change it