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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Understanding the K-Shaped Economy
- The K-shaped economy means some parts of the U.S. economy prosper while others struggle deeply.
- Middle market companies face declining earnings and margins, unlike larger public companies.
Middle Market Earnings Decline
- Middle market EBITDA has declined 20-25% since 2019 while public companies' earnings grow.
- Middle market firms have much narrower margins and tighter capital structures, making survival harder.
Market Power Harms Middle Market
- Middle market companies often serve larger firms without pricing power, pushing costs and risks onto them.
- This creates a corporate class system where larger firms prosper at the expense of smaller suppliers.