As his buddy Thiel very publicly supported future US President Donald Trump, Hoffman became an increasingly prominent Democratic donor to combat Trump, and he told us that he views his political donations to candidates the same way he does his tech investments.
He's also emerged in the last five years or so as a leading public expert on entrepreneurialism and careers, writing two career guides and hosting a popular business podcast called "Masters of Scale."
Hoffman told us that he's learned that having a master plan for his career is nowhere near as effective as continuing to build and contribute to his network and seeing what comes of that.
It's because, he said, "that's the thing that most catapults you, in terms of your capabilities, in terms of your abilities to do things."
Through his investments, Hoffman has built an incredible network of entrepreneurs and executives in tech.
The deal closed last December and Hoffman joined Microsoft's board, with Weiner still at the helm and the promise that LinkedIn would act as an independent subsidiary of Microsoft.
Hoffman told us the decision was very difficult but that he and his executive team ultimately decided that after discussions with Microsoft CEO Satya Nadella and his team about his goals and theirs, "There was a natural alignment of those missions, and we realized that we could better reach our mission combined."
Hoffman and Weiner have had a close working relationship and Weiner became one of the most lauded CEOs in any industry.
"Part of what made it very clear very early that Jeff was the right CEO is that he had actually really started embodying, acting as a founder," Hoffman said.
LinkedIn went public in 2011.
Hoffman told Wired in 2012 that Yee prefers to stay out of the spotlight.
Hoffman was intrigued but didn't want to be a lead investor in a potential deal, since he was building his own social network. He called up Thiel and they met with Zuckerberg.
Hoffman told us that he and Thiel found Zuckerberg to a painfully awkward kid, but they made a deal — the first investment into Facebook — and Thiel joined the company's board.
The two have served as friends and advisers to Zuckerberg over the past 15 years, and Hoffman told us that he's never seen anyone else make such a radical transformation into a high-functioning and visionary CEO than Zuck.
"I am learning from a bunch of things that he does," Hoffman said.
When eBay acquired PayPal for $1.5 billion in 2002, PayPal's stacked team of brilliant executives with alpha personalities went off to start their own companies, fueled by newly grown bank accounts.
The combination of the site being ahead of its time and Hoffman's inexperience as a manager caused him to abandon the project in 1999.
He considers it, however, an important crash course in both social networks in general and what it takes to run a company.
He told us that his favorite philosophers are Aristotle, Friedrich Nietzsche, and Ludwig Wittgenstein.
Hoffman said he realized at Oxford that if he went into academia, he would be focused on writing for an academic community rather than pursuing his long-held, highly ambitious guiding question, "How do I help humanity evolve?"
He does not remotely regret the education he received, but decided to go into tech. Why? He told us that while at Stanford, he saw how entrepreneurs were building businesses with the intention of improving the world, and he became a true believer.
Hoffman met Thiel when they were sophomores, and at that point Hoffman had a reputation for being a "pinko commie" and Thiel a "libertarian wacko," as Hoffman joked in an episode of his podcast "Masters of Scale." It was this contentious dynamic that proved to be the heart of their unlikely bond.
This friendship would go on to be one of the most impactful in Silicon Valley's history.
The Putney School's magazine The Putney Post interviewed several of Hoffman's classmates and teachers in 2009, and learned that Hoffman was an introspective kid who displayed his intelligence in class discussions.
While Hoffman was picked on for what teenagers would consider his love of "nerdy" things, he has only had good things to say as an adult about his time at Putney.
He said there was "a very pragmatic kind of 'work on solving the problem' versus 'being an expert within a discipline,'" at the school, and that he is grateful for learning that you could take "this kind of entrepreneurial focus on a personal life," instead of associating his future self with a single title like "product manager," "artist," or "lawyer."
"There's nothing obsessive like a kid," Hoffman told us, referring to his game-playing habit. "I spent literally days and days and days and days just doing that and that led me to a sense of strategy which was then, of course, very helpful when I later got to my entrepreneurial and business life."
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