Jack Selby on Chasing 500 Million Dollar Exits Instead of Outliers
Thiel Capital's Jack Selby rejects the trillion-dollar founder hunt, targeting 10% to 20% equity for $3M in non-coastal Series A deals.
Peter Thiel's 27-Year Partner on the AI Bubble, the Venture Capital Crisis, and the PayPal Mafia
With David Weisburd, Jack Selby · Wednesday, November 4, 2026
Jack Selby, Managing Director at Thiel Capital and an early PayPal executive, joins host David Weisburd to critique the hyper-concentration and excessive valuations of today's venture capital ecosystem. Selby breaks down his investment thesis at Copper Sky, which targets non-coastal founders at deep valuation discounts while bridging them to Silicon Valley networks. He also reflects on working alongside Peter Thiel for 27 years, recruiting lessons from PayPal, and why he believes the current AI investment frenzy is a bubble on borrowed time.
Key takeaways
- Jack Selby buys 10% to 20% equity in non-coastal Series A rounds for an average check of $3 million through Copper Sky. Read more →
- Roughly 90% of venture capital remains concentrated in three coastal states: California, New York, and Massachusetts. Read more →
- Thirteen years of zero-interest-rate policy funneled excessive capital into venture investing, creating an oversupply of sub-par managers who failed to distribute cash. Read more →
3 articles from this episode
Jack Selby on Buying Venture Deals at a 90% Discount
Thiel Capital's Jack Selby explains why non-coastal tech startups trade at a 90% discount to Silicon Valley, and why the gap is purely financial.
Jack Selby Says the Venture Capital Cull Is Only in Inning Two
Thiel Capital's Jack Selby explains why zombie VC funds are milking fees and rebranding failed portfolios around AI instead of returning cash.
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