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 Notes

• 00:00 Introduction and Guest Welcome
• 00:35 Morgan's Career Challenges: Overcoming rowing setbacks that shaped his approach to failure
• 01:52 Jordan's Career Pivot: Transitioning from engineering to business consulting
• 02:52 James' Childhood Influences: Early lessons in communication and resilience
• 05:01 Friendship in Competition: Balancing relationships while competing for the same deals
• 08:23 Founder Evaluation: What makes a great founder? Grit, market fit, and relentless drive
• 13:46 Dealing with Failure: Staying motivated in a high-rejection industry
• 16:59 Deal Hunt Stories: The lengths they've gone to win competitive deals
• 21:11 Market Trends: Current investment climate and future predictions
• 22:18 Israel's Startup Scene: Future exits and opportunities
• 23:11 VC Challenges: The hardest aspects of the job
• 24:53 Fund Creation: Insights on starting a new venture fund
• 27:26 Work-Life Balance: Managing personal and professional boundaries
• 31:10 Mentor Relationships: The importance of non-transactional connections
• 39:34 Advice for Aspirants: How to break into venture capital
• 43:36 Closing Thoughts: Final reflections on the VC journey

Links: 

• Morgan Gerlak

• Jordan Segall

• James Green