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.

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?

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

Jeff’s Most Recent Investment: Choco