Rick Heitzmann at Manhatta Standing Table #2

Today we're doing lunch at Manhatta, towering 60 stories above the financial district. Joining us is Rick Heitzmann, co-founder and partner at one of New York's most influential early stage venture firms, First Mark Capital. Rick has been early to some of the most category defining companies of the last decade, backing names like Pinterest, Airbnb, and DraftKings. That foresight has landed him on the Forbes Midas list, not once, not twice, but five times. And if that wasn't enough, he's living the dream of every New York sports fan, joining the ownership group of the New York Yankees. Timecodes: 00:00 – Cold open: The Vilification of AI 01:08 – Meet Rick Heitzmann 03:18 - Philly Sports Fan Turned Yankees Owner 05:02 - How Rick Got Into Yankees Ownership 06:00 - Spotting Trends Early: DraftKings, Airbnb & Pinterest 07:50 - Sports Betting, Prediction Markets & Integrity in Sports 09:40 - Danny Meyer, Hospitality & NYC Restaurant Culture 11:27 - Why the Restaurant Business Is So Tough Right Now 12:46 - AI, Digital Health & The Future of Healthcare 15:45 - The Explosion of Women’s Sports & Sports Merch Culture 18:02 - The Great Jersey Debate: Should Adults Wear Them? —

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Rick Heitzmann at Manhatta Standing Table #2 is an episode from On The Tape by RiskReversal Media.

This episode is 21:06 long.

This episode was published on May 19, 2026.

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