Contrasting Elon Musk, Peter Thiel, and Sam Altman

And Launching The Turpentine Awards

Housekeeping:

8 years ago, I tried to launch this site called The Rise Awards — basically a way to surface/highlight top talent. I also did an experiment like this with Cosign, where I got 1,000 people to share people they thought had potential to start big companies or be influential in some way. Looking back at the selections, the picks were actually useful and predictive. I didn’t end up scaling either of those efforts because On Deck and Village Global started taking all my time, but in continuing my tradition of trying the same idea over and over, I’ll soon be launching The Turpentine Awards, which will highlight people, companies, and products that the tech ecosystem should pay more attention to.

If you’re in the tech industry, please fill this out by the end of next week. We need hundreds of people to do so, so your participation will be greatly appreciated.

In exchange for doing so, you’ll get an invite to a Turpentine event, as well as exclusive early access to both the complete results and the full anonymized nomination data—not just the public summary. Thank you in advance!

As for this piece, I’m starting an experiment where I share my favorite conversations and private exchanges from the Turpentine universe to see if they resonate and if I should do more. Samo Burja and I discussed a framework on how to think about Peter Thiel, Elon Musk, and Sam Altman that I fleshed out a bit and wanted to share here.

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Peter Thiel is extremely good at noticing when the common consensus has flawed logic. Even if people are directionally making the right bet for the wrong reasons, there's some financial alpha there.

He’ll take something people take as conventional wisdom and flip it on its head. For example, we hear the word ‘monopoly’ and think that’s something we should avoid, but Peter says it’s something every business should aspire to. And conversely, instead of competing to win, we should avoid competition altogether. Another example is when he says we shouldn’t live every day as if it’s our last, in contrast to the popular phrase. Instead he says we should live every day as though it's going to go on forever—we should treat people like we’re going to see them again in the future and start working on projects that may take a long time

To contrast Peter’s approach with Sam Altman or Elon’s approach, Sam might hear the common wisdom, and his response would be "yes, and..." whereas Thiel's response would be "no, but." And I don't think Elon would even be listening — his perspective is so first principles driven that while he recognizes what is popular or not and can work with it, his decisions about what to do next are not tied at all to the mainstream but are following a technology tree chart derived from basic physics or his favorite science fiction story.

Thiel's question is, "How is the mainstream wrong, and what can we do about it to correct it?" which makes him a great investor

Sam will see where the enthusiasm and energy lie and ask, "Can we harness this and develop it further?" He sees cryptocurrencies and thinks, "What about World Coin - a coin for the world that changes the economic system to prepare for the post-scarcity future?" He sees green energy and thinks, "Let's start a fusion company."

Meanwhile, Elon will look at the space industry when everyone thinks it's hopeless, mature, and hyper-regulated…and he’ll make SpaceX. He'll go into a crowded field of failed green companies and try to make the electric car work this time because the batteries keep getting better. So logically, eventually, a car company would work, but you would have to think of it not in terms of car companies but the raw energy potential of batteries.

It makes sense, then, that Sam would have employees petition to keep him as OpenAI CEO after his ouster given his penchant for generating momentum, that Thiel would do the opposite and find himself outcasted at some point (his Trump bet in 2016), and that Elon would be somewhere in the middle on the agreeability/contrarianism spectrum, alternating between the hero and anti-hero approach depending on what he thinks is true and right. There’s a reason why Jack Dorsey singularly trusted Elon to lead Twitter, both from a competence and a moral perspective.

This brings me to an ideological comparison of the three. All of them have some variant of making sense of and legitimizing their own activity in the economic sphere.

• Thiel's would probably be very closely related to preventing violence on a global scale and the abuse and scapegoating of individuals. 

• Elon's would be focused on species survival — let's expand through the universe, let's have AI not kill us, let's reach a new destiny. 

• Sam is sort of like, "Let's reach abundance," and the critics and advocates of capitalism are both right. Socialists are right and capitalists are right - let's make capitalism work so well that we can all have UBI.

This orientation cashes out in differences in priority — I would expect Peter would be the most willing to back just causes that are unpopular, and Sam would be the most happy with popular causes like UBI which Peter hates. 

Sam is able to identify trends that people are excited about, which makes him an amazing fundraiser and recruiter. Thiel is looking for where the mainstream is wrong, so he's willing to take big bets that make him very unlikable — betting on Trump in 2016, betting against higher education in early 2000s, and saying ‘freedom and democracy are no longer compatible’ in 2009. Elon makes his big bets after a bit more traction, evidenced by buying into Tesla after it was founded and plowing into politics in 2024. Their involvement in politics is actually a helpful case study in describing their proclivities: Sam and Thiel got involved in 2016, with Sam supporting Hillary (the elite-favored candidate and momentum bet) and Thiel supporting Trump (the disreputable candidate and contrarian bet), and Elon mostly stayed out of politics until this past election. Also notably, while Thiel made a ‘seed bet’ in Trump, he didn’t really maintain his involvement and somewhat disassociated himself, whereas Elon got involved in 2024 and bet big enough to receive the benefits.

Thiel is more of a seed investor in contrarian ideas, making a bet and then looking to make the next one, whereas Elon is more of a builder/scaler, often coming in when something has been slightly derisked but taking the project all the way to completion (e.g. politics, xAI, Tesla). And when Elon bets, even if he bets a bit later than Thiel does, he goes all in, whereas Thiel runs a more diversified portfolio and hedges a bit more. Peter famously sold his Facebook shares too early. When Elon and Thiel were working together at Paypal, Thiel wanted to invest the $100M Paypal raised and use it to short the public markets. Elon is more “long-only” and has even been personally offended when people short his companies.

Peter is less likely to start and run a company himself. He might seed an idea, invest, etc, but not be the CEO of an operating company that has to do things day to day. Similarly, Sam doesn’t seem to have ideas in the same way Elon does, but he can smell when something is exciting and super charge it. And he’s amazing at spotting talent, recruiting, fund-raising, etc. And Elon, regardless of whether he gets involved early or late, will will the project to success, and will take ultimate responsibility in doing so.

This broader framework is quite rough, but it’s directionally useful in understanding three of the most important live players in tech (and more recently, politics). To that end, it’ll be interesting to see how Elon does in politics, given he doesn’t have total control like he usually does.