Trying To Understand Peter Thiel

Does one of his past books offer clues to the billionaire's motivations?

I grew up as a Massachusetts liberal Democrat, but every once in a while, I’d listen to Rush Limbaugh. Not because I believed what he was saying, but because I wanted to understand the people who did. It’s one of my most annoying Libra qualities, according to some of my friends: I always want to understand both sides.

I have struggled a lot with that in recent years, with people I know and like being enthusiastic for things I don’t believe in or don’t feel make sense. I was devastated by losing the chance to have a second (and better) President Clinton and mystified by people who chose Trump. However, it didn’t cost me friends or relationships. We got through it, and normalcy prevailed for a while.

This time is different and has been for a while. The gradual rightward shift of much of Silicon Valley caught me off guard to some extent. I was always aware there was a division between the liberalness of San Francisco and the cloaked conservatism of Silicon Valley. I knew about Peter Thiel from the old days of the PayPal mafia and wrote about some of his doings as part of my overall billionaire coverage when I was editing a luxury website. Just another billionaire with an interest in private bunkers, remote real estate, and making more money. Sure, he wanted people to quit school and become founders, and he believed in creating independent government-free areas including floating cities, still none of that was super unusual for Silicon Valley.

It wasn’t until he funded the lawsuits that ended Gawker Media that I realized we had a nemesis on our hands. This is a man who is willing to wait for his revenge, paying back Gawker back for outing Thiel in Valleywag, its Silicon Valley blog. Or maybe not. If Nick Denton, Gawker’s founder, is to be believed, what Thiel was really angry about was the coverage of the very messy things happening at PayPal. What he was upset about doesn’t matter as much as his ability to bring down a media outlet.

Since then, I’ve found myself saying watch Peter Thiel more times than I can count and far before the 2024 elections. It’s the old follow-the-money rule in action. Don’t pay attention to who is on the stage, look for who is in the shadows. He’s not a flashy billionaire, but he’s a connected one and as the co-founder of Palantir, he is benefiting as much from government favor as Elon Musk, perhaps more. He is the main reason JD Vance is vice president.

My willingness to see both sides is fading, but in the spirit of that, it was time to read some Thiel. Zero To One is Thiel’s book on founder culture, written with venture capitalist and Thiel acolyte Blake Masters. Masters has tried to run for political office multiple times and, like Thiel, is deeply connected to both Trump and JD Vance. This book came out in 2014, so it may not represent Thiel’s current views, but it was also written at a time when he probably felt freer to write what he felt. There’s nothing earth-shattering in the book. It’s a pretty bland espousing of typical beliefs on founder-led companies.

However, there are a few things in the book that feel especially relevant. Ability to risk, which I see in so many founder stories, comes up here, too. Boldness matters, as does moving forward quickly. It’s an echo of the Zuckerberg move-fast-and-break-things ethos, which he may actually have learned or been encouraged in by Thiel. There’s a lot of talk about building the foundations of a successful company and the value of treating people well, but not larding them with perks. According to the book, the ideal company has a small board, is founder-led, is run by employees who believe in the mission, and can create a monopoly.

Thiel just closed another fund for his Founders Fund, this one with 720 investors at $4.6 billion. Thiel’s tentacles are everywhere, in the fast-growing payments app Ramp, in Palmer Luckey’s Anduril, in nuclear power. I pay attention to Thiel not just as someone who wants to know who is curious about who is pulling the strings in government, but also as an investor.

I don’t know if following Thiel’s investments will bring you riches, but he is smart, ruthless, and his track record is the stuff of legend. Of course, he has the two things that accelerate wealth: enough money to risk and access to a wide variety of early-stage investments. However, it’s relatively easy to determine what his funds are investing in and watch those companies as they become public. Or you can follow his general interests: technology and biotech. Both sectors are full of volatile start-ups. Thiel’s guidance is to look for companies that can build and maintain market control of some sort.

At the end of the book, Thiel says: “Above all, don’t overestimate your own power as an individual. Founders aren’t important not because they are the only ones whose work has value, but rather because a great founder can bring out the best work from everybody at his company.” Part of what makes Thiel hard to pin down is that he’s libertarian but also Catholic and gay, both an individualist and a collectivist. Today’s billionaires seem to see the power of their money to remake the world with little thought to how it benefits those not within their circles.

I will leave you with one more quote from the book: “Perhaps every modern king is just a scapegoat who has managed to delay his own execution.”