David Weisburd and Erik Torenberg sit down with Chris Douvos, founder of Ahoy Capital and former Princeton Endowment manager, for a deep dive into the world of venture capital. Chris shares his perspective on the risk premium in venture, the influence of thought leaders like David Swensen, and the role of fund of funds in shaping the ecosystem. The conversation explores strategies for selecting top venture managers, the rise of Micro VCs, and the impact of regional industry clusters. Chris also weighs in on the evolution of large funds, the growing importance of asymmetric bets, and trends in crypto investing, offering practical advice for family offices and an inside look at the OpenLP movement.

David Weisburd and Erik Torenberg sit down with LP Chris Douvos, founder of Ahoy Capital and formerly Princeton Endowment.

(0:00) Introduction to Chris Douvos and venture capital complexities (1:44) Chris Douvos' venture capital journey (3:10) Understanding venture capital from a financial perspective (5:00) Analyzing the risk premium in venture capital (7:29) David Swenson's impact and the role of fund of funds (11:15) Selecting successful venture capital managers (13:46) Predicting the future of venture capital ecosystems (16:47) Sponsor: AngelList (22:43) AI Squared's investment potential and data scientists as investors (23:38) Balancing specialization and generalization (24:35) The significance of AI and regional industry clusters (25:55) The rise of Micro VCs and solo GPs (27:49) Venture fund life cycle, fund size, and investment strategy (33:45) The evolution of large venture funds and crypto investments (37:03) Embracing asymmetric bets in venture capital (40:41) Preparing for future fund growth and Y Combinator's influence (46:10) Direct investing advice for family offices (47:31) OpenLP movement, transparency, and secondary markets in venture capital (50:06) Closing thoughts and appreciation