Olivia: Alright Jackson, if Peter Thiel wrote a self-help book, what would the title be? Jackson: Easy. How to Win Friends and Bankrupt Your Enemies. Or maybe, The Subtle Art of Not Giving a Fck... About Democracy.* Olivia: That's disturbingly accurate. And it perfectly sets the stage for the book we're diving into today: The Contrarian: Peter Thiel and Silicon Valley’s Pursuit of Power by Max Chafkin. Jackson: I’ve heard this one is a bombshell. It’s got some pretty polarizing reviews, with some readers calling it a bold, essential portrait and others seeing it as a biased takedown. Olivia: It definitely is. And Chafkin is the perfect person to write this. He's a veteran tech reporter for Bloomberg Businessweek, so he's been covering this world for over a decade. He's not just an outsider looking in; he understands the culture he's dissecting. The book is this deeply reported, almost chilling look at one of the most powerful and enigmatic figures of our time. Jackson: And that culture, as Chafkin shows, really starts with Thiel's own bizarre and lonely childhood. It's a wild origin story.

Olivia: It really is. The book opens with this incredible image of Thiel as a kid in the 1980s, living in a bland California suburb. He and his friends were these classic nerds, obsessed with Dungeons & Dragons. But here’s the tell: Thiel always, always had to be the Dungeon Master. Jackson: The one who controls the game. Olivia: Exactly. A friend of his from that time is quoted in the book saying that for Thiel, being the Dungeon Master meant, "You get to determine the reality." And that one line becomes a powerful metaphor for his entire life. He’s always trying to be the one who sets the rules of the game, whether it's in finance, technology, or politics. Jackson: That’s fascinating. So this isn't just a power trip that started when he got rich; it was baked in from the beginning. Where did that come from? Olivia: Chafkin traces it back to this profound sense of otherness. Thiel was an immigrant from Germany, his family moved around a lot, even living in apartheid-era South Africa for a time. He was intellectually brilliant—a chess prodigy who was nationally ranked—but he was also socially awkward and, according to his friends, relentlessly serious. He was bullied, pranksters would put 'For Sale' signs on his lawn. He was an outsider. Jackson: So he's basically building his entire identity around being the guy who says the opposite of whatever is popular? It's like a brand. Olivia: It becomes his brand, but Chafkin argues it started as a defense mechanism. This culminates when he gets to Stanford University in the 80s. He expects this rigorous intellectual haven, but instead, he finds what he sees as a culture of unserious parties and liberal "groupthink." He feels completely alienated. Jackson: I can see how that would be frustrating for a super-serious, brilliant kid. But a lot of people feel out of place in college. What did Thiel do about it? Olivia: He didn't just withdraw; he went on the attack. He co-founds a right-wing campus newspaper called the Stanford Review. It was his first real venture, and it was designed to be a provocation. It was his platform to challenge what he called the "pernicious liberal plot" on campus. Jackson: What kind of stuff were they publishing? Olivia: Chafkin details some pretty shocking examples. The paper attacked affirmative action, feminism, and gay rights. Thiel himself, during this period, was known to defend apartheid in South Africa on purely economic grounds, shocking his classmates. He was deliberately cultivating this persona of a right-wing provocateur. Jackson: Wow. Defending apartheid is a pretty extreme way to be a contrarian. It sounds less like intellectual curiosity and more like he just enjoyed being inflammatory. Olivia: And that's the tension the book explores. Is he a genuine intellectual challenging orthodoxy, or is he just a brilliant mind fueled by resentment? He was deeply influenced by the philosopher René Girard, who wrote about 'mimetic desire'—the idea that we all just copy each other's desires, leading to mindless competition. Thiel saw himself as the one person who could see outside this system. Jackson: He's the hero in his own story, the one who isn't just following the herd. Olivia: Precisely. He even had a quote he'd use to explain his thinking: "Maybe I do always have this background program running where I’m trying to think of, ‘O.K., what’s the opposite of what you’re saying?’ and then I’ll try that. It works surprisingly often." He built an entire ideology out of being the opposition. Jackson: It's one thing to have that ideology as a college student writing for a campus paper. It's another thing to have it when you have billions of dollars. Olivia: And that’s the pivot. This contrarian, 'burn it all down' philosophy wasn't just for college newspapers. He took it and built one of the most influential companies in Silicon Valley history: PayPal.

Jackson: Okay, so PayPal. Most of us just think of it as that button you click to buy stuff online. But in Chafkin's book, it sounds more like a revolutionary project. Olivia: It was. Thiel's original vision for PayPal was incredibly radical. He saw it as a way to create a new global currency, one that was outside the control of governments and central banks. He once said that PayPal could make it impossible for governments to regulate their economies through inflation. It was a deeply libertarian, almost anarchic, vision. Jackson: That is a much bigger idea than just making online payments easier. How did they even get it off the ground? Olivia: This is where the contrarian playbook gets weaponized. They embraced a strategy that would later be called 'blitzscaling.' The only thing that mattered was growth, at any cost. They literally gave money away. They offered $10 to every new user and another $10 for every user they referred. Jackson: Hold on, they were just paying people to sign up? That sounds completely insane. How could they afford that? Olivia: They couldn't! In early 2000, they were burning through $100,000 a day just on these bonuses. The company was hemorrhaging money. But Thiel and his team didn't care about short-term profitability. They had this internal metric they obsessed over called the "World Domination Index." Jackson: You're kidding. A 'World Domination Index'? That sounds like something from a movie. Olivia: It was real. It was a screen in their office that tracked user growth. As long as that number was going up, they felt they were winning. The goal wasn't to build a profitable business in the traditional sense; it was to achieve a monopoly so total that they could set the rules later. This meant ignoring conventional business wisdom, and also, ignoring a lot of laws. Jackson: What do you mean, ignoring laws? Olivia: PayPal operated in a massive legal gray area. They argued they were a technology company, not a bank, which allowed them to sidestep a mountain of federal banking regulations. They were essentially moving money around the world without the oversight that a normal financial institution would have. Thiel’s response to a reporter who asked if they were a bank was, "No one knows what defines a bank. There’s no clear standard." Jackson: That is audacious. It's the classic Silicon Valley move: 'It's not illegal if we call it something else.' Olivia: Exactly. And this is the blueprint. Chafkin argues that the 'PayPal Mafia'—this tight-knit group of early employees like Elon Musk, Reid Hoffman, and others who all became incredibly successful—exported this playbook across Silicon Valley. When you see Uber rolling into cities and ignoring taxi laws, or Facebook's early motto of "Move fast and break things," that's the legacy of PayPal's 'blitzscaling' philosophy. It's a culture of growth at all costs, where the rules are for other people. Jackson: And it creates this culture of loyalty, right? The book talks about the 'PayPal Mafia' being almost all young, white men from similar backgrounds. Olivia: Yes, Thiel famously said, "We were all the same kind of nerd." He hired people from his network, often from the Stanford Review. It created this intense, insular, and fiercely loyal culture. They saw themselves as rebels fighting against a corrupt establishment, and that bond became incredibly powerful. This network of people would go on to found or fund LinkedIn, YouTube, Yelp, SpaceX, and dozens of other world-changing companies. Jackson: So he's built this massive fortune and this network of loyalists. What does a man like that, who has already 'determined the reality' of online finance, do next? Olivia: He goes after his enemies. And he sets his sights on the ultimate prize: political power.

Jackson: This is the part of the book that feels like it shifts from a business biography to a political thriller. The Gawker lawsuit is just mind-blowing. Olivia: It's one of the most chilling stories of modern power I've ever read. For those who don't know, in 2007, Gawker's Silicon Valley blog, Valleywag, published a post titled "Peter Thiel is totally gay, people." Thiel was not publicly out at the time, and he saw this as a profound violation. Jackson: And his response wasn't to issue a statement or write an op-ed. Olivia: No. His response, as Chafkin meticulously details, was to secretly fund a multi-year, multi-million-dollar legal war to destroy the entire media company. He hired a team to find people who had been wronged by Gawker and then bankrolled their lawsuits. The most famous of these was the wrestler Hulk Hogan, who sued Gawker for publishing a sex tape. Jackson: And Thiel was behind that the whole time, in secret? Olivia: For nearly a decade. He spent at least $10 million on it. When his involvement was finally revealed after Gawker was forced into bankruptcy by a $140 million judgment, Thiel was asked about it. His response was incredible. He said, "It's the most philanthropic thing I've ever done." Jackson: Philanthropic? That’s genuinely terrifying. The idea that a billionaire can decide a news organization is a 'bad actor' and then secretly erase it from existence is a massive threat to a free press. Olivia: It sent a shockwave through journalism. But for Thiel, it was a demonstration of his core belief: that there are enemies who need to be defeated, and that power, including financial power, is the tool you use to do it. This wasn't just business; it was a personal vendetta executed with the precision of a corporate takeover. Jackson: And this same logic seems to apply to his political moves, especially his support for Donald Trump. Olivia: Absolutely. The book makes it clear that Thiel's support for Trump was another contrarian bet. In early 2016, most of Silicon Valley was horrified by Trump. But Thiel saw an opportunity. He believed Trump, like him, was an outsider challenging a corrupt system. Jackson: But the most shocking part was when he made his biggest move. Olivia: Right. In October 2016, the Access Hollywood tape comes out. Trump's campaign is in a death spiral. Republicans are abandoning him in droves. And what does Peter Thiel do? He donates $1.25 million to a pro-Trump Super PAC. He didn't just stick with Trump; he doubled down when everyone else was running for the exits. Jackson: Chafkin portrays this as a pure power play, not a genuine belief in Trump's ideology, right? Olivia: Exactly. It was a calculated risk. If Trump lost, Thiel would be a pariah, but he was already seen that way by many in the Valley. If Trump won, however, Thiel would be one of the only people in a powerful industry who had been loyal to him. He would have unparalleled access and influence. Jackson: And that's exactly what happened. Trump wins, and suddenly Peter Thiel is on the transition team, suggesting cabinet members and shaping policy. He tried to get his allies appointed to dismantle what he called the "administrative state"—agencies like the FDA. Olivia: He even used his influence to benefit his own companies. Palantir, his data-surveillance company, won a massive $800 million contract with the U.S. Army after years of being shut out. Anduril, another defense company he backed, got contracts to build Trump's border wall. His bet paid off, not just in political influence, but in cold, hard cash. Jackson: It's the ultimate expression of his philosophy. Challenge the system, back the ultimate contrarian, and then rewrite the rules of reality to benefit yourself.

Olivia: So when you connect all the dots, from the D&D-playing kid who wanted to control the game, to the PayPal founder who broke the rules to win, to the political kingmaker who backed an outsider to upend the system... it's all the same story. Jackson: It’s a consistent through-line. The methods get more sophisticated and the stakes get higher, but the core motivation seems to be the same. Olivia: And that's the deep insight of Chafkin's book. He argues this isn't just about one man's strange and vengeful personality. It's about how Silicon Valley's pursuit of power, personified by Thiel, has become a political force that is actively trying to remake America in its own image—less democratic, more hierarchical, and run by a small group of 'builders' who believe they know best. Jackson: The book is called The Contrarian, but it seems like his contrarianism is just a means to an end. The end being power. Olivia: That's the chilling conclusion. He’s a privacy advocate who founded a surveillance company. A free-speech champion who secretly killed a media outlet. A libertarian who profits from massive government contracts. The contradictions are the point. They allow him to be whatever he needs to be to win. Jackson: And it leaves you with a really unsettling question: In a world where billionaires can bankrupt media outlets and install their allies in government, what does 'power' even mean anymore? And who holds them accountable? Olivia: It's a heavy question, and we'd love to know what you think. Does Thiel represent the future of innovation, or a threat to democracy? Let us know your thoughts on our socials. Jackson: This is Aibrary, signing off.