Today’s guest, Andrew Milgram, spent $600M buying NYC taxi medallions at the peak of Uber's power—an investment which gives you a sense of Andrew’s style. He describes a “K-shaped economy,” where one small group of companies does incredibly well while the rest struggle. Amidst it all he tries to build unique views in unexplored areas—be that Native American gaming, tax credits, regulatory gaps, or taxis. If you are interested in distressed investing, or the economy outside MAG7 and AI, this is a great listen. Timestamps 0:00 Intro 0:55 Understanding the K-Shaped Economy 3:04 Middle Market Analysis & Data Insights 8:01 Challenges Facing Middle Market Companies 13:45 Distressed Investing Explained 22:27 The Taxi Medallion Investment Story 47:21 Engaging with Regulators and Stakeholders 48:32 Building Relationships with Taxi Workers Alliance 50:27 Taking the Taxi Operation Public 51:35 Challenges and Opportunities in the Taxi Industry 55:00 Investing in Distressed Assets 57:21 Negotiation Principles & Relationship Building 1:01:24 Employee Retention Tax Credit Opportunity 1:27:33 Private Credit and Equity Markets Insights 1:35:30 Personal Reflections & Motivations 1:38:33 The Kindest Thing