E451: Peter Thiel's 27-Year Partner on the AI Bubble, the Venture Capital Crisis, and the PayPal Mafia

What if the best venture capital opportunities are hiding in the 47 states Silicon Valley largely ignores?
In this episode, I sit down with Jack Selby, Managing Director at Thiel Capital and an early member of the PayPal Mafia, to explore why he believes venture capital has become dangerously concentrated in Silicon Valley and overpriced AI startups. After working alongside Peter Thiel for 27 years, Jack is pursuing a contrarian strategy through Copper Sky, investing in promising technology companies outside California, New York, and Massachusetts. Jack explains why he can invest at roughly one-tenth of Silicon Valley valuations, how the next Carvana could emerge from cities like Phoenix or Milwaukee, and why venture capital's obsession with trillion-dollar outcomes may be hurting LP returns. We also discuss the hiring culture behind PayPal's extraordinary alumni network, why struggling venture firms have become zombies, and Jack's conviction that today's AI investment boom is a bubble.