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 2. •

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? • 1.

Lessons from Founding 10+ Companies Worth $27BN 2. •

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? • 1.

Incubating World’s Best Companies 2. •

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? • 1.

Current State of Venture 2. •

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? •