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

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