Andrew Milgram, founder of Marblegate, reveals shocking data about America's "K-shaped economy". The conversation covers his unique roll-up-the-sleeves approach to distressed investing, why he predicts continued business bankruptcies, and how tariff uncertainty could devastate middle-market companies while potentially benefiting large public corporations. 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 #DistressedInvesting #KShapedEconomy #MiddleMarket #Bankruptcy #EconomicTrends #InvestmentStrategy #CorporateRestructuring #MarbleGate #BusinessFailure #FinancialCrisis Presented by Ramp: https://ramp.com/business-cards?utm_s Sponsored by AlphaSense and Ridgeline: https://www.alpha-sense.com/invest/ https://www.ridgelineapps.com/ ****** Patrick O'Shaughnessy is the CEO of Positive Sum. All opinions expressed by Patrick and podcast guests are solely their own and do not reflect the opinion of Positive Sum. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. Clients of Positive Sum may maintain positions in the securities discussed in this podcast. To learn more, visit psum.vc