Kevin Ryan: Are the Best CEOs the Best Fundraisers & Why Ownership Should Not Be a Focus in VC|E1138

Kevin Ryan is one of the leading serial entrepreneurs and investors in New York. Previously he co-founded MongoDB, Business Insider, Gilt Groupe, Zola, Nomad Health, Pearl Health, and was the CEO of DoubleClick (Acquired by Google for $3.1B). Today, Kevin is the founder and CEO of AlleyCorp, a venture capital firm that incubates and invests in transformative companies in healthcare, diversified tech, robotics, and impact. Just yesterday, Alleycorp announced their $250M fund, their first ever external capital. ----------------------------------------------- Timestamps: (0:00) Intro (00:40) Background (01:34) Early Signs of Exceptionalism (05:09) Defining the Biggest Successes (08:57) Lessons from the Dot-com Era (12:47) Market Timing & Future Outlook (17:47) Insider vs. Outsider Founders (21:52) Concerns on AI Advantages & Startup Competition (24:51) Value of Investors in the Early Stages (26:54) Significance of Serial Entrepreneurs (35:13) Why Do Many Incubators Fail? (49:40) Challenges of Liquidity Management & Knowing When to Sell (59:05) The Changing Landscape of Venture Capital (56:36) Relationship to Money (01:02:27) Quick-Fire Round ----------------------------------------------- In Today’s Episode with Kevin Ryan We Discuss: 1. Early Signs of Entrepreneurship: How did Kevin’s early life shape his career? How would his parents and teachers describe him? Does Kevin agree that successful entrepreneurs always show signs early? What does Kevin think about luck vs. skill? Why does Kevin think that most things are out of your control as an entrepreneur? 2. Lessons from Founding 10+ Companies Worth $27BN: Does Kevin agree the best CEOs are also the best fundraisers? What were Kevin’s biggest lessons from scaling DoubleClick from 20 to 2000 employees? What was Kevin’s a-ha moment behind Business Insider? What was the reason behind its success? Why does Kevin believe the best founders are always in unfamiliar fields? 3. Incubating World’s Best Companies: How does Kevin allocate resources between incubations vs. investments? What are the biggest commonalities between successful companies at AlleyCorp? Is Kevin a market-led or people-led investor? What does Kevin think is the most important element in achieving product-market fit? What was Kevin’s biggest miss on selecting founders? What were his takeaways? 4. Current State of Venture: Why does Kevin believe venture is more competitive now than ever before? What does Kevin know now that wish he’d known when he started investing? Does Kevin agree rich investors make better investors? Why does Kevin not care about ownership? Does Kevin agree with Doug Leone that venture has transitioned from a high boutique margin industry to a low margin commoditised industry? Does Kevin agree with Peter Fenton that price is a mental trap? ----------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZTtgTNBKwtZBMHvl?si=85bc9196860e4466 Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-twenty-minute-vc-20vc-venture-capital-startup/id958230465 Follow Harry Stebbings on Twitter: https://twitter.com/HarryStebbings Follow Kevin Ryan on Twitter: https://twitter.com/kevinryan Follow 20VC on Instagram: https://www.instagram.com/20vchq Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/contact ----------------------------------------------- #20vc #harrystebbings #kevinryan #mongodb #alleycorp #ceo #founder #venturecapital #businesstips #investing #businessstrategy #publicmarket