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How I Invest · 3 min · Nov 4, 2026

He screens local founders for venture-scale ambition

JSJack Selby · Managing Director, Thiel Capital

Jack Selby says local founders may bring grit but still need ambition for venture-scale outcomes.

In this episode

Full analysis
  1. 32:21Cheap capital left venture with zombie funds6 min
  2. 42:27AI can produce strong returns without trillion-dollar exits3 min
  3. 18:36Lower entry prices change the venture return math3 min
  4. 6:48Silicon Valley's edge is capital access, not scarce talent6 min
  5. 38:46Mega-funds and early-stage funds need separate benchmarks3 min
  6. 45:31He screens local founders for venture-scale ambition3 min
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“I have to make sure that my entrepreneurs are sufficiently grandiose when they take my money.”
JSJack Selbyat 46:28 · How I Invest
46:28

Takeaways

  1. He needs a path to at least a $500 million company outcome.
  2. He treats founder ambition as separate from grit.
  3. Returning from Silicon Valley can pair high expectations with lower entry costs.

About this segment

Jack Selby says local founders may bring grit but still need ambition for venture-scale outcomes. He looks for grandiosity and values founders who've seen Silicon Valley's operating standards.

JS

Jack Selby

Jack Selby is a Managing director at Thiel Capital, early PayPal team member, and Clarium Capital cofounder.

Joined PayPal as an original employee, led international operations, and co-founded Clarium Capital with Peter Thiel.

From “Peter Thiel's 27-Year Partner on the AI Bubble, the Venture Capital Crisis, and the PayPal Mafia”, Nov 4, 2026. Watch the full episode

Transcript

From the transcript How I Invest publishes with the episode.

  1. 45:43

    to give fairness. It's the one aspect of my geography where I invest noncoastal that I'm the most envious of Silicon Valley. This is probably my biggest challenge. Like, when I meet that entrepreneur in Milwaukee, is he or she... Are they going to be able to work their tail off and get me to one of those minimum $500,000,000 type outcomes? Because oftentimes, he or she will take my money because they think venture capital is special or sexier, whatever it may be, and they're gonna work their tail off, go through blood, sweat, and tears, all these near death experiences.

  2. 46:13

    Like, okay, Jack. We're gonna sell this widget for a $100,000,000, five or seventeen years out. I say, no. No. No. And that's because on a relative basis, they'll be one of the richest people in Milwaukee. And Milwaukee. And God bless them for being the wealthiest person in Milwaukee, but that's not what my money's for. Like, I have to have that minimum $500,000,000 type outcome with my first fund in order for my math to work.

  3. 46:32

    I don't have to find a trillion dollar company, but I have to have that minimum $500,000,000 outcome. And too often, I have found, and this is going back to the analogy of me being a talent scout, I have to make sure that my entrepreneurs are sufficiently grandiose when they take my money. Like, buddy at Greylock coined this phrase that I've stolen, You have to have equal bits, grit, and grandiosity.

  4. 46:53

    Grit, I've got all day long in Milwaukee and Cincinnati and Phoenix. What I often have to be much more on the lookout for is the grandiosity piece. Reminds me of a Jason Lemkin tweet, which I think it was during COVID where he said, in San Francisco, I'm unhappy but productive. Outside of San Francisco, I'm happier but less productive. Therefore, I will stay in San Francisco. I I think there's something to that.

  5. 47:14

    There... There's this memetic copying where, sure, you might have $20,000,000, but if your neighbor has a $100,000,000, now you're suddenly unhappy. And people generally look at this as as a negative in terms of happiness, but in terms of productivity, it's a very positive kind of capitalistic type drive that that leads a lot of these submarkets like a San Francisco. In an ideal world, like, I would love it when young entrepreneurs go to the Bay Area right out of school from one of these noncoastal places and then move back.

  6. 47:40

    And so they've been infected. They could see what great They've been infected by the grandiosity in Palo Alto. Yeah. But they didn't they didn't stick for whatever reason, and they moved back to Phoenix or Milwaukee or Cincinnati or Houston. That's the best model? With our first fund, we saw kind of an equal split between folks that had done some version of that and then just homegrown entrepreneurs.

  7. 47:58

    But I certainly look for it. And because if you've been in Palo Alto and you've seen that work ethic and you have that grandiosity and you just kind of learned how things work, and you can then come back to one