Uploaded September 2025 | Updated September 2026, 6 hours ago
On this episode of Invested, Michael hosts David Fialkow, co-founder and Managing Director of General Catalyst, one of the world’s leading venture capital firms managing over $40 billion. From early investments in companies like Airbnb, Stripe, and Warby Parker, to scaling global category leaders, General Catalyst has consistently backed transformative founders and ideas. David’s own career bridges entrepreneurship, film, and philanthropy. Before co-founding General Catalyst, he built and sold several companies across travel, specialty retail, and payments/financial services. Beyond investing, he’s an Academy Award–winning documentary producer, with credits including Navalny and Icarus, which exposed Russia’s state-sponsored doping scandal. David is also deeply involved in civic and philanthropic initiatives. With a unique blend of business vision, creative storytelling, and social impact, David brings a rare perspective on how capital can be a force for both innovation and positive change.
Please rate this episode 5 stars wherever you stream your podcasts!
KEY TOPICS
00:00 Intro
02:30 College at Colgate and an ESL Shock
04:19 Discovering Storytelling and Filmmaking
09:06 Founding Last Minute Travel with Joel Cutler
11:32 Duty-Free Cruise Business and Sale to LVMH
13:55 How to Win Mentors: Relevance, Time & Opinions
15:53 Storytelling and “Hot Buttons” in Pitching
18:18 Crohn’s, Children’s Hospital Gift & the Ironman Bet
21:40 Why David Started General Catalyst
23:23 “Shots on Goal” and the VC Mindset
25:19 Starting Fund I and Raising Capital
28:11 Succession Planning
33:01 Ken Chenault Joins General Catalyst
39:28 Filmmaking with his wife Nina Fialkow
41:28 The Vow and Bringing Down NXIVM
46:16 Icarus: Pivot to Russian Doping Scandal
48:45 Navalny, Sugarcane, and Storytelling as Justice
57:00 Raising $12M through Film Screenings
59:26 Pan-Mass Challenge
01:01:27 Dana-Farber’s Impact on Oncology Drugs
01:02:21 On Luck, Teams, and Keeping Ego in Check
01:03:50 Why Israel: Mission, Resilience, and Tech Future
RESOURCES
Follow David on LinkedIn - linkedin.com/in/david-fialkow
Subscribe to Invested here: https://content.aleph.vc/invested
Learn more about Aleph: aleph.vc
Sign up for Aleph’s monthly email newsletter: https://newsletter.aleph.vc/
Subscribe to our YouTube channel: youtube.com/@aleph-vc
Follow Michael on Twitter: twitter.com/mikeeisenberg
Follow Michael on LinkedIn: linkedin.com/in/mieisenberg
Follow Aleph on Twitter: twitter.com/mikeeisenberg
Follow Aleph on LinkedIn: linkedin.com/company/aleph-vc
Follow Aleph on Instagram: instagram.com/aleph.vc
CREDITS
Executive Producer: Erica Marom
Producer: Myron Shneider
Video and Editing: Ron Baranov
Music and Creative Direction: Uri Ar
Content and Editorial: Kira Goldring
Design: Rony Karadi
On this episode of Invested, Michael hosts David Fialkow, co-founder and Managing Director of General Catalyst, one of the world’s leading venture capital firms managing over $40 billion. From early investments in companies like Airbnb, Stripe, and Warby Parker, to scaling global category leaders, General Catalyst has consistently backed transformative founders and ideas. David’s own career bridges entrepreneurship, film, and philanthropy. Before co-founding General Catalyst, he built and sold several companies across travel, specialty retail, and payments/financial services. Beyond investing, he’s an Academy Award–winning documentary producer, with credits including Navalny and Icarus, which exposed Russia’s state-sponsored doping scandal. David is also deeply involved in civic and philanthropic initiatives. With a unique blend of business vision, creative storytelling, and social impact, David brings a rare perspective on how capital can be a force for both innovation and positive change.
Please rate this episode 5 stars wherever you stream your podcasts!
KEY TOPICS
00:00 Intro
02:30 College at Colgate and an ESL Shock
04:19 Discovering Storytelling and Filmmaking
09:06 Founding Last Minute Travel with Joel Cutler
11:32 Duty-Free Cruise Business and Sale to LVMH
13:55 How to Win Mentors: Relevance, Time & Opinions
15:53 Storytelling and “Hot Buttons” in Pitching
18:18 Crohn’s, Children’s Hospital Gift & the Ironman Bet
21:40 Why David Started General Catalyst
23:23 “Shots on Goal” and the VC Mindset
25:19 Starting Fund I and Raising Capital
28:11 Succession Planning
33:01 Ken Chenault Joins General Catalyst
39:28 Filmmaking with his wife Nina Fialkow
41:28 The Vow and Bringing Down NXIVM
46:16 Icarus: Pivot to Russian Doping Scandal
48:45 Navalny, Sugarcane, and Storytelling as Justice
57:00 Raising $12M through Film Screenings
59:26 Pan-Mass Challenge
01:01:27 Dana-Farber’s Impact on Oncology Drugs
01:02:21 On Luck, Teams, and Keeping Ego in Check
01:03:50 Why Israel: Mission, Resilience, and Tech Future
RESOURCES
Follow David on LinkedIn - linkedin.com/in/david-fialkow
Subscribe to Invested here: https://content.aleph.vc/invested
Learn more about Aleph: aleph.vc
Sign up for Aleph’s monthly email newsletter: https://newsletter.aleph.vc/
Subscribe to our YouTube channel: youtube.com/@aleph-vc
Follow Michael on Twitter: twitter.com/mikeeisenberg
Follow Michael on LinkedIn: linkedin.com/in/mieisenberg
Follow Aleph on Twitter: twitter.com/mikeeisenberg
Follow Aleph on LinkedIn: linkedin.com/company/aleph-vc
Follow Aleph on Instagram: instagram.com/aleph.vc
CREDITS
Executive Producer: Erica Marom
Producer: Myron Shneider
Video and Editing: Ron Baranov
Music and Creative Direction: Uri Ar
Content and Editorial: Kira Goldring
Design: Rony Karadi
