Alan Feld sits down with David Weisburd to talk about his experience founding Vintage, the significance of product-market fit in VC, and how Vintage has thrived over two decades. They discuss the impact of personal history on investment decisions, building an enduring VC firm culture, and engaging with General Partners. They also touch on successful GP cultures, investment allocation, and VC-LP relationship transparency. (0:00) Diversification and elephant hunting (0:43) Welcoming Alan Feld to the podcast (1:06) Founding Vintage and the importance of direct investment experience (1:51) Structure and strategy of Vintage (3:19) Trade-offs in structuring funds by sector vs. asset class (5:55) Importance of understanding underlying companies and defining product market fit (8:57) Sponsor: Bidav Insurance Group (9:46) Lessons learned and internal culture at Vintage over 20 years (15:30) Understanding why top VCs make poor investments and the correlation with personal trauma (22:21) Management mistakes, culture, and keys to building an enduring organization (27:15) Hiring operators, engaging with GPs, and Vintage's growth (32:30) Importance of passion and characteristics of successful GPs (37:02) Humility, honesty, and transparency in VC relationships (42:05) Investment allocation and evaluating follow-on investments (45:16) Diversification and concentration in portfolios (46:36) Key takeaways and advice from Alan Feld (47:43) Closing remarks and future engagements