20VC: Are the Best CEOs the Best Fundraisers, Are the Best Founders Insiders or Outsiders to a Problem, Why Ownership Should Not Be a Focus in VC & The Biggest Lessons Scaling MongoDB to $26BN Market Cap with Kevin Ryan, Founder @ AlleyCorp

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. 

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?