General Catalyst Co-Founder David Fialkow on Pitching VCs Through ‘Hot Buttons,’ Billion-Dollar Storytelling & Bringing Down a Cult

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.

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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 - https://www.linkedin.com/in/david-fialkow

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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