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. Highlights: How PayPal assembled a team that went on to build some of Silicon Valley's most influential companies What Jack learned from working alongside Peter Thiel for 27 years Why nearly 90% of venture capital flows to just three states How Copper Sky invests at roughly one-tenth of Silicon Valley valuations Why Silicon Valley's greatest advantage may be access to capital rather than talent How Jack uses his network to connect non-coastal founders with Silicon Valley investors Why entry price matters more than finding the next trillion-dollar company How venture capital's liquidity crisis created a generation of zombie funds Why AI is allowing smaller teams to build valuable companies outside traditional technology hubs Why Jack believes today's AI investment boom is a bubble Guest Bio: Jack Selby is Managing Director at Thiel Capital and an early member of the PayPal founding team, where he led international operations before the company's acquisition by eBay. He has worked alongside Peter Thiel for 27 years and co-founded Clarium Capital, a global macro hedge fund. Jack is also an investor at Copper Sky, a venture capital firm focused on identifying promising technology companies outside traditional coastal venture markets. His investment experience spans technology, finance, venture capital, film, and nonprofit initiatives. Sponsors: Juniper Square: Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit https://www.junipersquare.com/howiinvest . Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdpierce.com . **Stay Connected with David Weisburd: ** X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdcapital.com/ **Stay Connected with Jack Selby: ** LinkedIn: https://www.linkedin.com/in/jackselby/?skipRedirect=true Questions or topics you want us to discuss on How I Invest? Email us at <a href="mailto