Rick Heitzmann at Manhatta  |  Standing Table #2 episode artwork

EPISODE · May 19, 2026 · 21 MIN

Rick Heitzmann at Manhatta | Standing Table #2

from RiskReversal Pod · host RiskReversal Media

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? — FOLLOW US Instagram: riskreversalmedia   Twitter: https://x.com/riskreversal LinkedIn: riskreversalmedia   #investing #stocks #stockmarket #ApexFintechSolutions Standing Table is made possible through our continued partnership with Apex Fintech Solutions. Apex Fintech Solutions provides the tools and services that enable hundreds of clients to launch, scale, and support digital investing for tens of millions of end investors. The company provides essential infrastructure and a comprehensive ecosystem of cloud-based products to enable and streamline trading, wealth management, cost basis, tax reporting, and, through its subsidiary Apex Clearing™, custody and clearing. For more information, visit the Apex Fintech Solutions website: https://apexfintechsolutions.com/ LinkedIn: apex-fintech SUBSCRIBE: RiskReversal Pod for more from Guy and Dan: https://apple.co/3RzvgpD RiskReversal Media channel for more episodes and content:    / @riskreversalmedia   The financial opinions expressed in Risk Reversal content are for information purposes only. The opinions expressed by the hosts and participants are not an attempt to influence specific trading behavior, investments, or strategies. Past performance does not necessarily predict future outcomes. No specific results or profits are assured when relying on Risk Reversal. Before making any investment or trade, evaluate its suitability for your circumstances and consider consulting your own financial or investment advisor. The financial products discussed in Risk Reversal carry a high level of risk and may not be appropriate for many investors. If you have uncertainties, it's advisable to seek professional advice. Remember that trading involves a risk to your capital, so only invest money that you can afford to lose. Derivatives are not suitable for all investors and involve the risk of losing more than the amount originally deposited and any profit you might have made. This communication is not a recommendation or offer to buy, sell or retain any specific investment or service.​​

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? — FOLLOW US Instagram: riskreversalmedia   Twitter: https://x.com/riskreversal LinkedIn: riskreversalmedia   #investing #stocks #stockmarket #ApexFintechSolutions Standing Table is made possible through our continued partnership with Apex Fintech Solutions. Apex Fintech Solutions provides the tools and services that enable hundreds of clients to launch, scale, and support digital investing for tens of millions of end investors. The company provides essential infrastructure and a comprehensive ecosystem of cloud-based products to enable and streamline trading, wealth management, cost basis, tax reporting, and, through its subsidiary Apex Clearing™, custody and clearing. For more information, visit the Apex Fintech Solutions website: https://apexfintechsolutions.com/ LinkedIn: apex-fintech SUBSCRIBE: RiskReversal Pod for more from Guy and Dan: https://apple.co/3RzvgpD RiskReversal Media channel for more episodes and content:    / @riskreversalmedia   The financial opinions expressed in Risk Reversal content are for information purposes only. The opinions expressed by the hosts and participants are not an attempt to influence specific trading behavior, investments, or strategies. Past performance does not necessarily predict future outcomes. No specific results or profits are assured when relying on Risk Reversal. Before making any investment or trade, evaluate its suitability for your circumstances and consider consulting your own financial or investment advisor. The financial products discussed in Risk Reversal carry a high level of risk and may not be appropriate for many investors. If you have uncertainties, it's advisable to seek professional advice. Remember that trading involves a risk to your capital, so only invest money that you can afford to lose. Derivatives are not suitable for all investors and involve the risk of losing more than the amount originally deposited and any profit you might have made. This communication is not a recommendation or offer to buy, sell or retain any specific investment or service.​​

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Rick Heitzmann at Manhatta | Standing Table #2

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This episode was published on May 19, 2026.

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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...

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