David Fialkow, co-founder and managing director of General Catalyst, is an entrepreneur, investor, philanthropist, and Oscar-winning documentary producer. He discusses how storytelling from filmmaking helps founders, Boston’s entrepreneurial culture, building a travel empire with long-term partners, launching General Catalyst during the post-dotcom winter, and the firm’s founder-focused, intergenerational approach to investing.
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question_answer ANECDOTE
Building A Travel Empire From Last Minute Deals
David and Joel Cutler started National Leisure Group selling last-minute discounted trips and built the largest US tour and cruise retail business.
They prioritized customer experience, empowered young leaders, used early tech, and sold the company at the right time.
question_answer ANECDOTE
90 Days To Ironman Sparked General Catalyst
A bet to raise money for hospital research pushed David to learn to swim and complete the Hawaiian Ironman in 90 days.
That intense experience sparked the idea to start a firm to help founders, which became General Catalyst.
volunteer_activism ADVICE
Be Mentors Not Just Investors
When General Catalyst started in 2001 they framed themselves as mentors, not traditional VCs, focusing on founder support over product direction.
Prioritize building teams, getting revenue, and helping founders raise capital rather than dictating product choices.
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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!
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