In this episode, I had the honor of talking to John Cowgill, Partner at Costanoa Ventures.

Costanoa leads Seed and Series A investments in tenacious and thoughtful founders who change how business gets done. The firm's investments include companies such as Alation, BillGo, Demandbase, Kenna Security, Roadster, and Quizlet.

We talked about John past experience as a McKinsey consultant, how he got into the VC industry, the current VC landscape, his investing frameworks, and many other topics.

Here are some of the questions I asked him:

  • How were you as a kid? What were you interested in growing up?
  • When you were in college, you worked in business development for Techweek, a nationwide technology conference company. There, you helped to host the first tech conference ever in Miami, and you booked Pitbull as a keynote speaker. How was that experience?
  • What's your current stance on Miami and the San Francisco exodus?
  • Before you came to Costanoa, you were a consultant at McKinsey, advising consumer and technology companies on strategy and operations projects. How was your experience working at McKinsey? What is your current stance on consulting firms and their role in forecasting and giving their customers insights for the future?
  • After McKinsey, you joined Costanoa Ventures. Back then, was going to VC the only next step you had in mind?
  • VCs have multiple motivations. Some VCs are motivated primarily by money, and others are more motivated by finding and helping great founders, and they let the returns flow from that. How did you perspective on VCs motivations changed over time?
  • Something you value in founders is the combination of an unshakable belief in their ability to succeed and the humility to constantly modify their vision to adapt to market signals. Which are some of the other heuristics you develop to spot inevitable founders?
  • One of your biggest investing regrets has been to pass opportunities where growth and team were great but TAM seemed bounded at the time. What are some other non-intuitive truths you learned about investing?
  • One of the challenges many companies in your portfolio dealt with this past year was the transition to remote work. What have you learned about the companies that transitioned successfully?
  • Your favorite book is How Will You Measure Your Life by the late Clayton Christensen. Also, you recommend founders to read every Bezos and Buffett shareholder and employees letters. Can you talk about how these readings influenced you and mention other influential books?
  • On the quarantine you rediscovered a bunch of hobbies that you lost touch with, such as playing the guitar, writing music, cycling, cooking, playing online poker, etc. How has that changed your routine and how you approach work?
  • Meditating positively impacted your mood, focus, and sleep. Could you talk more about how it changed you? Also, could you share your experience with Sam Harris' Waking Up app?