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Book review: The Contrarian - Peter Thiel’s biography is a messy tale of a messy man

Bloomberg Businessweek journalist Max Chafkin attempts to uncover the mysterious man behind Silicon Valley's biggest companies and investment firms- PayPal, Palantir, Founders Fund, et al. Who is Peter Thiel really?

October 09, 2021 / 09:11 AM IST

Don’t judge a book by its cover, they say. I did not. But after reading The Contrarian- Peter Thiel and Silicon Valley’s Pursuit of Power , I realised the book’s cover- where the billionaire is steadfastly, slightly menacingly, gazing at something, is a surprisingly accurate early indicator of what this book thinks Thiel isa cold, unflinching, calculating power broker. But is that all Peter Thiel really is?

Thiel is a billionaire, entrepreneur, venture capitalist, hedge fund manager, savvy political operator- a few more descriptors than even Tony Stark can fit in; and yet nobody really knows him, except what he wants you to know about him, via the odd interview or column.

Silicon Valley is in a curious place in 2021- where money is flowing freely, valuations are interplanetary (because sky high seems tame at this point) and yet somehow large technology companies are under more scrutiny than ever before. This is a great time to shed light on one of its most influential figures someone who has ridden the dotcom boom, backed Stripe, SpaceX and Facebook, and has staunchly supported Donald Trump. Max Chafkin, Features Editor at Bloomberg takes on the compelling but challenging task of unmasking someone who never seems to take off his mask. The result is a vastly compelling but somewhat uneven tale of a man who seems too Machiavellian for Machiavelli himself to believe. 

Thiel is not your usual Silicon Valley billionaire- a ‘contrarian’ in every sense of the word. Thiel has lamented the rise of social media and apparent fall of real technology innovation, but is an early investor and long time board member of Facebook. He has predicted financial, economic and political shifts, and bet on them when it seemed crazy. He is gay but also has a curious history of being associated with far-right, anti-LGBTQ groups. He has encouraged students to drop out of expensive colleges and start up, but dozens of his own associates and connections come from his alma mater Stanford.

Chafkin examines these apparent contradictions, and in the process, the man himself. Despite not getting any access to Thiel himself, Chafkin attempts to unearth details beyond what people know, and succeeds in many ways. For instance, his portrayal of Thiel’s Stanford days- where he pursued his bachelor’s degree in philosophy and then also studied law- is compelling. A picture emerges of a young man already entrenched in far-right political beliefs, in a university whose President David Starr Jordan himself endorsed many of these views.


In one case, apparently an African American student confronted Thiel about his pro-apartheid stance. Thiel told her that South Africa's systematic denial of civil rights to Black people was economically sound. Any moral issues were irrelevant .These thoughts and college writings get a lot of air time- maybe more than needed, considering how much people change in the years after, but the book also tries to prove that Thiel has not changed much since then- the calculated pursuit of profit, with technology, politics and people being merely tools to it.

The writing here is particularly sharp, and I often felt transported to Stanford, with vivid descriptions of beer-laden chess games, racist shouts and memorable anecdotes.

If you’re curious about who Peter Thiel is, the book offers many revelatory details, including large scale tax evasion, being a nationalist and wanting to quash immigration, but securing a citizenship in New Zealand, cold wars with Elon Musk at PayPal, and how Facebook spread disinformation before, during and after the COVID-19 pandemic, and far from Thiel- a board member- stopping it, he may have benefitted from it.

Thiel’s cybersecurity business Palantir- born out of post 9/11 surveillance paranoia is also well-explained, along with how despite Thiel’s anti-government stance, the US government gave Palantir huge revenues, even though its actual efficacy in some cases (such as capturing Bin Laden) is questionable.

His relationship with Trump is fascinating, but a little less so than what the book thinks. The book’s main insight in many places, but especially in relation to Trump seems to be Thiel’s hypocrisy- of saying one thing and practising another, or cozying up to Trump purely for business reasons, even if he did not fully agree with Trump’s typically incendiary rhetoric (but did agree with the underlying philosophy). It is perfectly valid to examine this contradiction or Thiel’s thinking, but billionaires, or rather anyone of influence, being a hypocrite is not a surprise to anyone.

The political beliefs of Thiel and his close business associates are also revealing, even as the book says Thiel projects different versions of himself and his beliefs to people he meets- investors, Democrats, Republicans, the press, depending on what he wants each of them to see. I suspect many of us do this on a day to day basis. Throughout the book, the words far-right, alt-right and libertarian are used so often that they lose meaning by the end.

Thiel's beliefs versus his actions, and his actions versus ambitions are examined in detail, and every anecdote and incident is a pixel in the same image- of a cold, profit-minded, and in woke terms, ‘problematic’ billionaire.

Except for a few courtesy throwaway lines, there is nothing flattering about Thiel in this book. It is ironic that after Chafkin spoke to hundreds of people over years for this book, his portrayal of Thiel is largely what everyone already knows of him, albeit with a lot more details.

If a biography is meant to tell you a person’s emotions and feelings, there is none of that here, because Thiel does not seem to have emotions as much as very strong ideas about things that he communicates in a haphazard manner.

Despite being very critical though, The Contrarian: Peter Thiel and Silicon Valley’s Pursuit offers a detailed, well-narrated and comprehensive look at one of the world’s most powerful people, and how he came to wield it.

The Contrarian: Peter Thiel and Silicon Valley's Pursuit of Power

By Max Chafkin

Publisher: Penguin Press

Available on Amazon
M. Sriram
first published: Oct 9, 2021 09:11 am

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