20VC: Lessons Scaling Insight Partners to a $20BN Latest Fund, The Two Biggest Learnings on Price, How to Manage and Train Young People in Venture, Why Business Classrooms Do Not Work and How to Assess the Two Commodities in Life; Money and Time 

Jeff Lieberman is the Managing Director @ Insight Partners, one of the leading investing franchises of the last 25 years with their most recent flagship fund announced earlier this year being a staggering $20BN. As for Jeff, over the last 24 years at Insight, he has led investments in leading companies such as Qualtrics, DeliveryHero, HelloFresh, Cvent, Mimecast, and Udemy. As a result of his many investing successes, he has been selected by AlwaysOn as a Venture Capital 100 winner and by Forbes as a member of the Midas List.

In Today’s Episode with Jeff Lieberman You Will Learn:

1.) Origins into Venture:

• How did Jeff’s roommate at college open his eyes to the world of venture capital?

• What were Jeff’s biggest lessons from seeing the work ethic of his parents?

• How does Jeff imbue the same level of ambition on his children that he had growing up with no money?

• Why is Jeff keen for his children not to go to college? How does he advise them?

2.) Jeff Lieberman: The Investor:

• What are Jeff’s biggest observations on the current landscape given his seeing first hand the dot com bust and 2008? How is now different? How is it the same?

• Price Sensitivity: How does Jeff reflect on his own price sensitivity? How has it changed over time?

• Deployment Pace: How does Jeff analyse deployment pace today both for the industry and for Insight? Does Jeff agree with the notion of “playing the game on the field”?

• The Biggest Miss: What have been some of Jeff’s biggest misses? How did those misses impact the process with which he invests?

3.) Insight: The Firm

• What are the most challenging elements of firm building today?

• Why do all juniors have control over the Partners calendars? How does this work in practice?

• How does Jeff create an environment of safety where very young, junior people feel like they can challenge anyone and have discussion?

• How do Insight train young people? What is the process? What works? What does not work?

4.) AMA:

• What does Jeff know now about venture that he wishes he had known when he started?

• What would Jeff most like to change about the world of venture capital?

• What advice does Jeff give to young people today entering the industry?

Item’s Mentioned In Today’s Episode with Jeff Lieberman

Jeff’s Favourite Book: Man’s Search For Meaning

Jeff’s Most Recent Investment: Choco