Peter Thiel's 27-Year Partner on the AI Bubble, the Venture Capital Crisis, and the PayPal Mafia
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.
- Jack Selby buys 10% to 20% equity in non-coastal Series A rounds for an average check of $3 million through Copper Sky. Read →
- Roughly 90% of venture capital remains concentrated in three coastal states: California, New York, and Massachusetts. Read →
- 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 →