Subscriber OnlyBooks

The Contrarian. Peter Thiel and Silicon Valley’s Pursuit of Power: horribly fascinating

Book review: It is extraordinary the PayPal founder’s actions failed to make him a pariah

The Contrarian: Peter Thiel and Silicon Valley’s Pursuit of Power
The Contrarian: Peter Thiel and Silicon Valley’s Pursuit of Power
Author: Max Chafkin
ISBN-13: 978-1526619556
Publisher: Bloomsbury
Guideline Price: £25

In July 1999 I was visiting Silicon Valley when a public relations friend rang. He had a little story for me, he said. He was working with a small tech start-up called Confinity. It was launching a new service that would enable people to transfer money to each other digitally, using the infrared port built into Palm Pilots, the hot Valley handheld device of the moment.

Confinity had just staged a launch stunt at which Nokia Ventures beamed $3 million in venture funding into the Palm Pilot of Confinity’s chief executive – just the sort of geeky-wacky story hook that might interest readers of, which I occasionally wrote for, and The Irish Times. He set up an interview with the chief executive. The new money transfer service was called PayPal.

The chief executive was an unknown named Peter Thiel.

Before long, Confinity “pivoted”, as the Valley term goes. PayPal became the company, not the product, and infrared ports on Palm Pilots were ditched. Instead, PayPal became the payment method of choice on auction site eBay, which would eventually buy the company, and online. Along the way, Elon Musk would serve as chief executive, too, and then he and Thiel would have a famous falling out. And Thiel would evolve into a Valley giant.


Meanwhile, my brief Confinity story, one of the first written on Thiel and PayPal, would bring years of headaches. Hundreds of people wrote me emails, complaining that they'd been scammed by supposed online sellers using PayPal, and demanding I make Thiel or Musk return their money (as if).

The problem was that, initially, PayPal wasn’t registered as a bank, and so offered no fraud protection. I’d assumed this was an oversight at a phenomenally fast-growing start-up that would swiftly be addressed.

A feature

How wrong I was. According to Max Chafkin’s new biography of Thiel, this financial wild west was a feature, not a bug, and wasn’t addressed for ages. Thiel, inspired by the fictional independent crypto-island in Neal Stephenson’s 1999 cult sci-fi novel Cryptonomicon, wanted an untethered financial transaction service. PayPal was, at least at first, to be the ultimate in geek libertarian offshoring: anonymous, untraceable, outside the mainstream banking grid, able to be utilised by anyone, including hackers, scammers, pornographers, and illegal arms and drugs merchants – indeed, many of the those who would quickly embrace cryptocurrencies, for the same murky reasons.

In Ireland, some might vaguely know of the mega-billionaire for (1) his apparent interest in injecting the blood of young people to curtail ageing, (2) acting as a supporter and adviser to Donald Trump, (3) receiving ardent genuflections at past Web Summits or (4) as a major investor in Stripe, the huge online payments company founded by the Collison brothers from Limerick.

Well, if you admire Peter Thiel, you probably won’t after even just a chapter or two of The Contrarian: Peter Thiel and Silicon Valley’s Pursuit of Power. Not if you aren’t an anti-immigrant, sexist, homophobic, white supremacist, “Nazi-curious”, alt-right sympathiser, that is. Chafkin documents all those Thiel leanings – some are even enthusiasms.

Chafkin carefully documents a detestable man of extraordinary contradictions alongside his (self-) vaunted contrarianism – someone who even Steve Bannon pronounces too extreme in his beliefs and intentions for the Trump White House (thus, few of Thiel’s 100-plus recommended political appointees bore serious consideration). “Thiel’s ideas were so extreme that they didn’t easily fit into any political ideology,” writes Chafkin.

Solitary, ruthless

Thiel, a childhood immigrant from Germany, was an odd, solitary, ruthless, chess-obsessed youth. Then as an academically brilliant Stanford student, Thiel – who is gay – wrote, supported and edited vile, anti-gay, racist pieces in the ultra-conservative Stanford Review (and regularly employs Review alumni in key positions in his companies). He’s dismissive of women (in 2009, Thiel wrote an essay arguing that the growth of the welfare state and the extension of the vote to women were the two factors that had demolished “the notion of a capitalist democracy”.

It’s all horrible, and horribly fascinating, from Stanford to PayPal to his secretive surveillance companies Palantir and Clearview, his failure as a hedge fund creator, his extreme libertarianism, his critical Facebook board role in making Zuckerberg powerfully unanswerable, his public posturing as an ideological and financial guru, his political ascent due to Trump, and his vast increase in personal wealth during a pandemic in which he seems indifferent to its deaths.

What comes across is Thiel’s ultimate unknowableness, and how extraordinary it is that his actions and beliefs failed to long ago make him a pariah.

What appals is just how much Silicon Valley is happy to venerate and (literally) codify so many of his repugnant excesses (the book’s section on what really happened at that famous Thiel-arranged roundtable between Trump and big name tech chief executives will make it hard to ever again take their diversity statements seriously).

And, what thoroughly alarms is how interconnected and recurrent the same people are in this tale, mostly male and white, across politics, finance, business, academia and technology. If there’s a deep state, it’s surely the vast ultra-conservative intermesh of names in the modern techno-political-military-industrial complex exposed here.

Karlin Lillington

Karlin Lillington

Karlin Lillington, a contributor to The Irish Times, writes about technology