Invest Like the Best with Patrick O'Shaughnessy Andrew Milgram - Full-Contact Capitalism - [Invest Like the Best, EP.436]
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Aug 5, 2025 
Andrew Milgram, founder of Marblegate Asset Management, dives into the nuances of distressed investing in the middle market. He discusses the consequences of the K-shaped economy, where small firms struggle as larger entities thrive. Milgram shares his fascinating journey with NYC taxi medallions and stresses the importance of active engagement and negotiation in distressed assets. He also sheds light on niche investments, the emotional challenges of investing, and the need for transparency in the industry, emphasizing collective responsibility in addressing economic disparities.
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NYC Taxi Medallion Investment Story
- Marblegate acquired over 4,500 NYC taxi medallion loans after extensive research including driving taxis themselves.
- They found Uber was pulling drivers away with subsidies but medallion economics remained durable with operational improvements.
Data-Driven Taxi Decisions
- Marblegate obtained terabytes of ride-level NYC taxi data via a FOIA request and analyzed it.
- They discovered clear patterns in rider and driver behavior, enabling data-driven operational improvements.
Building Taxi Loan Portfolio
- Marblegate became largest lender via auctions and negotiations with banks and federal agencies.
- They stood up their own servicer due to complexity and unwillingness of others to handle politically sensitive loans.