The Contrarian

Sharing my learnings from the book, The Contrarian by Max Chafkin

The Contrarian by Max Chafkin

Since the days of the dot-com bubble in the late 1990s, no industry has made a greater impact on the world than Silicon Valley. And few individuals have done more to shape Silicon Valley than Peter Thiel. The billionaire venture capitalist and entrepreneur has been a behind-the-scenes operator influencing countless aspects of our contemporary way of life, from the technologies we use every day to the delicate power balance between Silicon Valley, Wall Street, and Washington. But despite his power and the ubiquity of his projects, no public figure is quite so mysterious.

In the first major biography of Thiel, Max Chafkin traces the trajectory of the innovator’s singular life and worldview, from his upbringing as the child of immigrant parents and years at Stanford as a burgeoning conservative thought leader to his founding of PayPal and Palantir, early investment in Facebook and SpaceX, and relationships with fellow tech titans Mark Zuckerberg, Elon Musk, and Eric Schmidt. The Contrarian illuminates the extent to which Thiel has sought to export his values to the corridors of power beyond Silicon Valley, including funding the lawsuit that destroyed the blog Gawker and strenuously backing far-right political candidates, notably Donald Trump for president in 2016. 

Eye-opening and deeply reported, The Contrarian is a revelatory biography of a one-of-a-kind leader and an incisive portrait of a tech industry whose explosive growth and power is both thrilling and fraught with controversy.

• Peter Thiel has had an outsize influence on one of the centers of the modern world: Silicon Valley. He’s founded spectacularly successful tech companies – and even sat at a US president’s side.
• Peter Thiel was a smart kid. At school, Thiel excelled at everything academic. He was also a brilliant chess player. At one point, he was among the best under-13 players in the whole country. He kept a sticker on his chess set that boasted, “born to win.” This haughty attitude meant that he wasn’t well liked at school. But he didn’t seem to care – according to one classmate, he walked around with an expression that said, “Fuck you, world.”
• There was one thing, though, that the young Thiel cared for deeply: the world of fantasy. He played Dungeons & Dragons, read the science-fiction novels of Isaac Asimov, and recited whole paragraphs of J.R.R. Tolkien. In their different ways, all of these passions would influence him. His senior-year quote, from the animated version of The Hobbit, said it all: “The greatest adventure is what lies ahead. / Today and tomorrow are yet to be said.”
• With his brilliant grades, Thiel secured a place at Stanford University to study philosophy. Rather than the elite learning environment he was hoping for, Thiel found a party atmosphere at Stanford. In response to this debauchery, Thiel developed a ritual. He would leave his dorm each morning, stride to the water fountain, and take a handful of vitamins. This was his way of showing how disciplined and superior he was to his hungover peers.
• While completing his studies, Thiel founded the Stanford Review, a right-wing tabloid newspaper. Its position was that Stanford was incurably left-wing and morally deviant. Thiel took aim at the university, its lecturers, and other students. 
• After graduating from Stanford, Thiel drifted between various high-flying jobs. He worked as a clerk for a judge, as a lawyer for the firm Sullivan & Cromwell, and then as a derivatives trader for Credit Suisse in New York. But when he returned to California and saw how the new tech companies were flourishing, he sensed his true calling.
• In the Bay Area, he met a young, brilliant software engineer called Max Levchin. The two of them embarked on one of the most important projects of Thiel’s life. It allowed him to unite his appetite for the internet boom with his ideology. This was PayPal.
• PayPal, which began life as Confinity, was founded in December 1998 by Thiel and Levchin. Their idea for the company was a digital wallet that provided an alternative to paper money. In those early days, it relied on a device called the PalmPilot: a personal digital assistant
• In 2000, PayPal merged with X.com, a financial startup run by another entrepreneur with a major career ahead: Elon Musk. Musk became CEO, but there were soon disagreements between him and Thiel. While Musk was away enjoying his honeymoon, he was ousted from the role. Thiel stepped in to head the company.
• But Thiel was always looking for the next opportunity. PayPal was floated on the stock market in 2002; that same year, without warning his colleagues, Thiel stepped down from his role and sold his shares. He’d use the proceeds for his next plan: he was going to set up a hedge fund called Clarium Capital.
• Clarium quickly became successful, largely through betting on big events in the global economy. On one of those – the oil crisis of 2003 – the company bet against the health of the US economy. Thiel and Clarium suddenly had $260 million under management as a result of this bet. Thiel also started to quietly invest in tech companies. One of those was headed by an abrasive, awkward Harvard student: Mark Zuckerberg. Attracted by its rapid growth across college campuses, Thiel became the first outside investor in Facebook.
• Thiel’s surveillance company Palantir revealed an authoritarian shift in his politics. Harking back to his love of fantasy, Thiel named the company after the palantíri, which were indestructible balls of crystal used as “seeing stones” in Lord of the Rings.
• In 2016, Thiel pledged his support to Donald Trump. In many ways, Trump was the perfect answer to all the liberals Thiel despised. Before long, Thiel and his billions were on the Trump train. At the 2016 Republican convention, Thiel gave a speech in support of Trump. “It’s time to rebuild America,” he said.
• After the 2016 election, Thiel found himself invited to join Trump’s transition team alongside Steve Bannon and Donald Trump Jr. His role was to draw up candidates for governmental positions, from Technology Officer to the head of the Food and Drug Administration.
• On December 14, 2016 – not long after his election victory – the president-elect called a big meeting of the US’s most successful tech leaders. In public, many of these tech leaders had supported Hillary Clinton and opposed Trump. However, now that they were all in the room with Trump, not one of them challenged him on the inflammatory things he’d said on the campaign trail. When push came to shove, it appeared these liberal tech CEOs cared more about their bottom lines than their principles.