Inside the VC Game: Conversations with Rising Stars Morgan Gerlak TCV, Jordan Segall Redpoint Ventures, James Green CRV

Three top-tier rising VCs – Jordan Siegel (RedPoint), James Green (CRV), and Morgan Gerlak (TCV) – pull back the curtain on venture capital. In this candid conversation, these friends and competitors share their journey from career pivots and childhood lessons to competitive deal wins and investment philosophies. Discover how they evaluate founders, maintain relationships in a cutthroat industry, and navigate the evolving VC landscape. Perfect for aspiring investors, entrepreneurs, and anyone fascinated by the startup ecosystem.  Episode Notes00:00 Introduction and Guest Welcome00:35 Morgan's Career Challenges: Overcoming rowing setbacks that shaped his approach to failure01:52 Jordan's Career Pivot: Transitioning from engineering to business consulting02:52 James' Childhood Influences: Early lessons in communication and resilience05:01 Friendship in Competition: Balancing relationships while competing for the same deals08:23 Founder Evaluation: What makes a great founder? Grit, market fit, and relentless drive13:46 Dealing with Failure: Staying motivated in a high-rejection industry16:59 Deal Hunt Stories: The lengths they've gone to win competitive deals21:11 Market Trends: Current investment climate and future predictions22:18 Israel's Startup Scene: Future exits and opportunities23:11 VC Challenges: The hardest aspects of the job24:53 Fund Creation: Insights on starting a new venture fund27:26 Work-Life Balance: Managing personal and professional boundaries31:10 Mentor Relationships: The importance of non-transactional connections39:34 Advice for Aspirants: How to break into venture capital43:36 Closing Thoughts: Final reflections on the VC journey Links:  • Morgan Gerlak • Jordan Segall • James Green