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“There’s a saying: friends come and go, but enemies accumulate,”
Max Chafkin, The Contrarian: Peter Thiel and Silicon Valley's Pursuit of Power
“In order to create something that deserves to sit alongside the best products in the world, you have to have spent enough time interacting with the best products.”
Max Chafkin, Design Crazy
“This group includes Elon Musk, plus the founders of YouTube, Yelp, and LinkedIn. They would provide the capital to Airbnb, Lyft, Spotify, Stripe, DeepMind—now better known as Google’s world-leading artificial intelligence project—and, of course, to Facebook.”
Max Chafkin, The Contrarian: Peter Thiel and the Rise of the Silicon Valley Oligarchs
“This shift was part and parcel with Thiel’s other project: an attempt to impose a brand of extreme libertarianism that shifts power from traditional institutions toward startup companies and the billionaires who control them.”
Max Chafkin, The Contrarian: Peter Thiel and the Rise of the Silicon Valley Oligarchs
“More than any other Silicon Valley investor or entrepreneur—more so even than Jeff Bezos, or Google founders Larry Page and Sergey Brin, or Zuckerberg himself—he has been responsible for creating the ideology that has come to define Silicon Valley: that technological progress should be pursued relentlessly—with little, if any, regard for potential costs or dangers to society.”
Max Chafkin, The Contrarian: Peter Thiel and the Rise of the Silicon Valley Oligarchs
“In 1996, there were no tech companies among the five most valuable traded on U.S. exchanges; in 2021 the entire top five consisted of U.S. tech companies. Today, the most prolific Hollywood studio is Netflix. More Americans get their news from social media, primarily Facebook, than from cable television.”
Max Chafkin, The Contrarian: Peter Thiel and Silicon Valley's Pursuit of Power
“It looks like it’s from another planet,” Jobs said. “A planet with better designers.”
Max Chafkin, Design Crazy: Good Looks, Hot Tempers, and True Genius at Apple
“X gave most of its customers checking accounts, and so those customers who were able to get their mail would sometimes immediately take advantage by writing a series of bad checks. “I was thinking, ‘What the hell did I step into,’ ” said an early hire who was tasked with handling fraud. “There was no sort of risk mitigation in place.” When employees told Musk that the bank that X had partnered with to handle the checking accounts was complaining about bounced checks, Musk seemed confused by the concept. “I don’t understand,” Musk said. “If you don’t have money in your account, why would you write a check?”
Max Chafkin, The Contrarian: Peter Thiel and the Rise of the Silicon Valley Oligarchs
“The libertarian success manual also argues that monopolies are good, that monarchies are the most efficient form of government, and that tech founders are godlike. It has sold more than 1.25 million copies worldwide.”
Max Chafkin, The Contrarian: Peter Thiel and the Rise of the Silicon Valley Oligarchs
“Today, the most prolific Hollywood studio is Netflix. More Americans get their news from social media, primarily Facebook, than from cable television.”
Max Chafkin, The Contrarian: Peter Thiel and the Rise of the Silicon Valley Oligarchs
“PayPal had been a libertarian company—in Thiel’s most extreme imaginings, it had been a way to unilaterally strip governments of the power to control their own money supplies. But Thiel was, after 9/11 anyway, no longer much of a libertarian, if he’d ever been one in the first place. He was growing skeptical of democracy, of immigration, and of all other forms of globalization—and he was, just then, working on a new company to suit his new politics.”
Max Chafkin, The Contrarian: Peter Thiel and the Rise of the Silicon Valley Oligarchs
“Thiel was pulled over, and the trooper asked if he knew how fast he was going. The young men in the rest of the car, simultaneously relieved to have been stopped and scared of the trooper, looked at each other nervously. “Well,” Thiel responded, in his calmest, most measured baritone. “I’m not sure if the concept of a speed limit makes sense.” The officer said nothing. Thiel continued: “It may be unconstitutional. And it’s definitely an infringement on liberty.”
Max Chafkin, The Contrarian: Peter Thiel and the Rise of the Silicon Valley Oligarchs
“he has been responsible for creating the ideology that has come to define Silicon Valley: that technological progress should be pursued relentlessly—with little, if any, regard for potential costs or dangers to society.”
Max Chafkin, The Contrarian: Peter Thiel and Silicon Valley's Pursuit of Power
“Another former chess player shared his own fond memory of Thiel from this era. Around the spring of 1988, the team was driving to Monterey for a tournament, with Thiel behind the wheel of the Rabbit. They took California’s Route 17, a four-lane highway that crosses the Santa Cruz Mountains and is regarded as one of the state’s most dangerous. The team was in no particular hurry, but Thiel drove as if he were a man possessed. He navigated the turns like Michael Andretti, weaving in and out of lanes, nearly rear-ending cars as he slipped past them, and seemed to be flooring the accelerator for large portions of the trip. Somewhat predictably, the lights of a California Highway Patrol cruiser eventually appeared in his rearview. Thiel was pulled over, and the trooper asked if he knew how fast he was going. The young men in the rest of the car, simultaneously relieved to have been stopped and scared of the trooper, looked at each other nervously. “Well,” Thiel responded, in his calmest, most measured baritone. “I’m not sure if the concept of a speed limit makes sense.” The officer said nothing. Thiel continued: “It may be unconstitutional. And it’s definitely an infringement on liberty.” The officer looked at Thiel and the geeks in the beater car and decided the whole thing wasn’t worth his time. He told Thiel to slow down and have a nice day. “I don’t remember any of the games we played,” said the man, now in his fifties, who’d been in the passenger seat. “But I will never forget that drive.”
Max Chafkin, The Contrarian: Peter Thiel and the Rise of the Silicon Valley Oligarchs
“Girard’s big idea—which Thiel would internalize and adopt as a guiding principle, both in investing and in life—was that people are motivated, at their core, by a desire to imitate one another. We don’t want the things we want, Girard argued, because we judge them to be good; we want them because other people want them. This “mimetic desire” was universal, leading to envy and, in turn, violence. Societies had historically used scapegoating—turning the violent impulse on a single, innocent member of the community—to channel and control these feelings, providing an outlet that staved off wars and mass killings.”
Max Chafkin, The Contrarian: Peter Thiel and Silicon Valley's Pursuit of Power
“The far-right ideas had been there for as long as the tech industry had existed—all the way back to the founding of Stanford University. But it had taken Peter Thiel to bring those ideas above the surface, and then to weaponize them.”
Max Chafkin, The Contrarian: Peter Thiel and the Rise of the Silicon Valley Oligarchs
“Clinton’s campaign had refused this kind of help, a decision Face-book executives later suggested might have cost her the election.”
Max Chafkin, The Contrarian: Peter Thiel and Silicon Valley's Pursuit of Power
“His worldview is that if you get one big thing right, and move hard with conviction, then nothing else matters,” said an early Clarium employee.”
Max Chafkin, The Contrarian: Peter Thiel and Silicon Valley's Pursuit of Power
“He wanted to control everything that touched his product: the creation of the product, the manufacturing, how that product went to market, and how the customer interacted with the product.”
Max Chafkin, Design Crazy: Good Looks, Hot Tempers, and True Genius at Apple
“We were a marketing-driven company that wasn’t focused on design or even delivering a product.”
Max Chafkin, Design Crazy: Good Looks, Hot Tempers, and True Genius at Apple
“I thought that a lot of the conventional ways people competed resulted in too many people [doing] conventional things,” he would say years later. “Then you end up in very competitive dynamics, and then even when you win it’s not quite worth it. You might get a slightly better paying job than you otherwise would, but you sort of have to sell your soul. That doesn’t sound like a very good economic or moral tradeoff.”
Max Chafkin, The Contrarian: Peter Thiel and Silicon Valley's Pursuit of Power
“Team Rogue.” It roughly meant doing whatever had to be done, even pushing ethical limits. It’s unlikely that Thiel knew about Team Rogue, but Chmieliauskas said that Palantir’s senior leaders certainly did, and in any case Chmieliauskas was following one of the most important rules of the Thielverse: Ignore the rules when necessary.”
Max Chafkin, The Contrarian: Peter Thiel and the Rise of the Silicon Valley Oligarchs
“When a reporter noted that many other online payment companies had chosen to comply with federal banking regulations—by, for instance, asking for social security numbers and verifying customers’ addresses before allowing them to make payments—Thiel called them “insane” and suggested that was why they were growing so slowly.”
Max Chafkin, The Contrarian: Peter Thiel and Silicon Valley's Pursuit of Power
“But with the car nearing production, Musk needed capital and asked Thiel if he’d be interested in investing. Thiel said no—indicating that he was passing in part because, according to Musk, “he doesn’t fully buy into the climate change thing.” In doing so, and in choosing his own political bias over the audacity of Musk’s bet (not to mention the overwhelming evidence offered by mainstream climate science), Thiel lost out on a chance to own a substantial chunk of a company that would be worth $800 billion by the end of 2020. Instead of Founders Fund, Musk took the deal to VantagePoint Venture Partners, a little-known firm with a reputation for investing in green energy companies. VantagePoint wound up with 9 percent of Tesla when it eventually went public.”
Max Chafkin, The Contrarian: Peter Thiel and the Rise of the Silicon Valley Oligarchs
“The challenge in delivering simplicity is, marketing wants to bring more functionality to bear, engineering wants to bring more options to bear—and all of that just adds to confusion and clutter. That’s when a task like printing a document becomes confounded with all these buttons and fields and tabs.”
Max Chafkin, Design Crazy: Good Looks, Hot Tempers, and True Genius at Apple
“Thiel has also contributed to a reactionary turn in our politics and society that has left the United States in a much more uncertain place than he found it in when he went into business for himself in the mid-1990s. He is a critic of big tech who has done more to increase the dominance of big tech than perhaps any living person. He is a self-proclaimed privacy advocate who founded one of the world’s largest surveillance companies. He is a champion of meritocracy and intellectual diversity who has surrounded himself with a self-proclaimed mafia of loyalists. And he is a champion of free speech who secretly killed a major U.S. media outlet. “He’s a nihilist, a really smart nihilist,” said Matt Stoller, the anti-monopoly activist and author of Goliath: The 100-Year War Between Monopoly Power and Democracy. “He’s entirely about power—it’s the law of the jungle. ‘I’m a predator and the predators win.’ ” That, more than anything, may be the lesson that Thiel’s followers have learned—the real meaning of “move fast and break things.”
Max Chafkin, The Contrarian: Peter Thiel and Silicon Valley's Pursuit of Power
“Using a fixed dock on the bottom of the screen and relying heavily on visual metaphors and animation, it would evolve into the modern versions of both OS X and iOS while exerting an obvious influence on operating systems offered by Microsoft and Google, and”
Max Chafkin, Design Crazy: Good Looks, Hot Tempers, and True Genius at Apple
“Balaji Srinivasan, an investor who was one of Thiel’s picks to lead the FDA under Trump—has argued that the media deserves to be destroyed and replaced by something he calls “full stack narrative”—public relations, in other words. “Builders must critique the critiques,” he tweeted, using the Randian word for entrepreneur that is favored by Thiel and his friends. “Stop the people standing athwart the future yelling stop. It’s your duty.”
Max Chafkin, The Contrarian: Peter Thiel and Silicon Valley's Pursuit of Power
“The challenge in delivering simplicity is, marketing wants to bring more functionality to bear, engineering wants to bring more options to bear—and all of that just adds to confusion and clutter.”
Max Chafkin, Design Crazy: Good Looks, Hot Tempers, and True Genius at Apple
“An ambitious effort to build the first handheld computer, the Newton, seemed to sputter even before the first version was released.”
Max Chafkin, Design Crazy: Good Looks, Hot Tempers, and True Genius at Apple

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