Intro

Episode 422 of The VentureFizz Podcast features David Fialkow, Co-Founder & Managing Director of General Catalyst. Entrepreneur, venture capitalist, philanthropist, and Oscar winner - those are just a few of the words that describe David’s legendary career. As you’ll hear from this interview, he emphasizes the importance of storytelling, which he originally learned from filmmaking, but it goes beyond making a compelling documentary. It is an often-overlooked but essential skill for every entrepreneur. Whether you are hiring, winning over customers, or raising capital, being able to align everyone with your mission through a powerful narrative is critical for success. Most of you are likely familiar with General Catalyst. They are one of the top VC firms in the world, having backed a "Who’s Who" of tech giants including Stripe, Anduril, Circle, Airbnb, HubSpot, Snap, Canva, and Discord - just to name a few. In this interview, we cover a lot of ground, plus David shares lots of stories and interesting advice along the way, such as: What it’s like to win an Oscar and making impactful documentary films. David’s thoughts on the Boston tech scene. His long standing partnership with Joel Cutler (which I didn’t know they met when they were seven years old) and the details on their entrepreneurial initiatives in the travel industry including building the largest tour & cruise business in the U.S. The story of how a donation to Children’s Hospital led him to compete in the Ironman triathlon with just 90 days to train. How General Catalyst got started during the 2001 VC winter after dot-com bubble burst. The firm’s myopic focus on founders and their approach to building a firm with long term, intergenerational value. Investing in pillar Boston companies like HubSpot, Circle, ITA Software, KAYAK, and others… and their thought process around expanding the firm to the West Coast. The importance of surrounding yourself with people who know more than you do. And so much more! Podcast Sponsor: This podcast is brought to you by one of the strongest longtime supporters of the local startup ecosystem, Silicon Valley Bank, a division of First Citizens Bank. With more than 1,500 bankers and relationship advisors and $44B in loans as of Q4 2025 – SVB delivers expert guidance, specialized products and a team that knows the innovation economy inside and out. Learn more at SVB.com.