Before billionaire LinkedIn founder Reid Hoffman met Peter Thiel in college, the ‘pinko commie’ had heard of the ‘libertarian wacko’ — now, they have been friends for 30 years

Reid Hoffman, left, and Peter Thiel have been close friends for 30 years, even though their ideological divide is as drastic as ever. Greylock Partners
  • Reid Hoffman and Peter Thiel have been been friends for 30 years and worked together at PayPal.
  • From the day they met at Stanford, they were ideological opposites.
  • The results of their friendship have made them two of the most influential people in Silicon Valley.

To a casual observer, the friendship between Reid Hoffman and Peter Thiel may not make any sense. The two billionaire investors are actively on opposite sides of the political spectrum, with Thiel as President Donald Trump’s connection to the tech world and Hoffman as a donor to and advocate of the politicians opposing Trump every step of the way.

While the stakes are high enough now that their support can affect the entire United States, their roles as ideological opposites were established from the day they met. It’s actually the crux of their 30-year friendship, Hoffman explained in a recent episode of Business Insider’s podcast “Success! How I Did It” – and this friendship has been one of the most influential in Silicon Valley’s history.

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Hoffman and Thiel met as sophomores at Stanford, after both had heard plenty about the other: Hoffman heard Thiel was a “libertarian wacko” and Thiel heard Hoffman was a “pinko commie,” as Hoffman put it in an episode of his own podcast, “Masters of Scale.”

Hoffman told us that as soon as they started talking to each other, they began arguing, “and the first umpteen conversations were all literally discovering all of the areas where we disagreed. And I think part of the reason that our friendship formed [was] that in those discussions, we both realised that we had a real strong belief in truth, we had a real strong belief in discourse as the way of getting there, we had a strong belief in listening to alternative perspectives. I know that he certainly made my thinking a lot sharper and I hope I did the same for him.”

Several years after college, in the mid-1990s, the two even had a short-lived public access TV show in California. They would have a guest on, like an editor from the conservative magazine “The American Spectator,” for the purpose of discussing a topic, but Hoffman said the conversations always ended up as he and Thiel arguing with each other.

When Thiel launched the online payment service PayPal in late 1998, he brought Hoffman along as a founding board member. Hoffman would join as a full time employee in 2000, staying until they sold the company to eBay in 2002.

This was the age of the so-called “PayPal Mafia,” where Hoffman and Thiel worked alongside a cast of tech power players like SpaceX and Tesla CEO Elon Musk and the founders of YouTube. The team Thiel assembled became the foundation for a generation of Silicon Valley entrepreneurs who not only built their own successful companies but guided subsequent generations.

One of those younger entrepreneurs was Mark Zuckerberg, who met Hoffman in 2004 when the 20-year-old college dropout was looking for funding for his startup, The Facebook. Hoffman called up Thiel to join him in a meeting with Zuckerberg, and they ended up becoming the first investors in the company.

Today, the two friends are notable players in some of the most vicious times in recent American political history, but while Hoffman hates that Thiel supports Trump, he still turns to him for entrepreneurial insights.

“Peter is, as anyone who knows, super smart – an out-of-the-box thinker and as likely to provoke you with a question that you hadn’t thought of as anyone else on the planet,” Hoffman said.