RiskReversal Pod

Rick Heitzmann at Manhatta | Standing Table Podcast Episode #2

RiskReversal Pod

Show Notes

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.​​

More from RiskReversal Pod

Oct 23, 2026

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.

Oct 21, 2026

Dan Nathan hosts Damien Lewke, CEO and founder of AI-native cybersecurity company Nebulock. Lewke recounts his career from nation-state defense at Northrop Grumman to CrowdStrike, Palo Alto Networks, MIT research in NLP, and leading AI detections at Arctic Wolf. They discuss how the threat surface has expanded with distributed environments and how the ChatGPT moment accelerated both defensive usability and offensive capability. Lewke explains Nebulock’s “hunt-first” mission to give any team machine-speed detection and response, positioning it across converging markets like SIEM, MDR, AI SOC, and insider threat/UEBA. The conversation covers enterprise AI adoption, supply-chain risk, investor perceptions following “Mythos” breach disclosures and agent security as insider risk.

Oct 19, 2026

Learn more about Astraeus Wealth Management: ⁠http://astraeuswealth.com/partner-with-us⁠

Oct 16, 2026

Checkout David's Book: https://www.amazon.com/dp/1997701774?lv=shuf&channelId=500&plpRedirect=mhFallback

Oct 14, 2026

Dan Nathan welcomes Deirdre Bosa to the Okay, Computer podcast to discuss her upcoming daily Yahoo Finance show, “Deirdre Bosa Live,” launching November 9 and airing weekdays 1–2 PM PT. They dig into how Microsoft has shifted Copilot toward a model-agnostic approach—routing tasks to the most cost-effective models amid open-source commoditization—while also launching its Maia 300 custom AI chip to manage supply and spending uncertainty. The conversation touches on Meta’s product-driven resurgence, enterprise adoption dynamics, and investor concerns about AI infrastructure capex and debt. They compare emerging personal AI assistants (Muse, Instinct, and OpenAI “Dot”), emphasizing utility, branding, and trust/security as prerequisites for broader adoption, with Apple and identity layers like 1Password seen as potential catalysts. They close on China’s low-cost, high-volume token usage pressuring global pricing and shaping open-source competition.

See all episodes →