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:
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Early Signs of Entrepreneurship
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How did Kevin’s early life shape his career? How would his parents and teachers describe him?
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Does Kevin agree that successful entrepreneurs always show signs early?
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What does Kevin think about luck vs. skill? Why does Kevin think that most things are out of your control as an entrepreneur?
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Lessons from Founding 10+ Companies Worth $27BN
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Does Kevin agree the best CEOs are also the best fundraisers?
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What were Kevin’s biggest lessons from scaling DoubleClick from 20 to 2000 employees?
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What was Kevin’s a-ha moment behind Business Insider? What was the reason behind its success?
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Why does Kevin believe the best founders are always in unfamiliar fields?
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Incubating World’s Best Companies
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How does Kevin allocate resources between incubations vs. investments?
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What are the biggest commonalities between successful companies at AlleyCorp?
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Is Kevin a market-led or people-led investor?
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What does Kevin think is the most important element in achieving product-market fit?
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What was Kevin’s biggest miss on selecting founders? What were his takeaways?
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Current State of Venture
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Why does Kevin believe venture is more competitive now than ever before?
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What does Kevin know now that wish he’d known when he started investing?
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Does Kevin agree rich investors make better investors?
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Why does Kevin not care about ownership?
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Does Kevin agree with Doug Leone that venture has transitioned from a high boutique margin industry to a low margin commoditised industry?
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Does Kevin agree with Peter Fenton that price is a mental trap?
