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) Introduction and Alan's journey to founding Vintage (6:37) Importance of product-market fit and sector-based fund structure in venture capital (8:57) Sponsor: Bedav Insurance Group (9:46) Lessons learned from managing and growing Vintage over 20 years (17:05) Role of personal history in shaping successful entrepreneurs and investment decisions (21:29) Building an enduring venture capital firm: Culture, succession, and economic sharing (28:27) Regrets, reflections, and Vintage's approach to engaging with General Partners (33:40) Cultures at GPs that consistently return alpha and importance of humility and honesty (41:30) Allocating investments, follow-on investing, and the value of transparency in VC-LP relationships (46:36) Wrap-up: Reflections on building a lasting venture fund