My guest today is Andrew Milgram. Andrew is the founder of Marblegate Asset Management, an alternative investment firm that invests in credit opportunities and special situations. He joins me to discuss his unique approach to distressed investing in the middle market, revealing how middle market EBITDA has declined 20-25% since 2019, creating what he calls the "K-shaped economy." His investment stories are legendary, particularly his $600+ million bet on NYC taxi medallions, which we go into in great detail. We discuss Marblegate’s approach to negotiation, sourcing deals directly from hundreds of regional banks, and understanding the human element in distressed situations. Please enjoy this conversation with Andrew Milgram.

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Show Notes:

(00:00:00) Welcome to Invest Like the Best

(00:04:58) Understanding the K-Shaped Economy

(00:07:08) Middle Market Challenges and Data Insights

(00:16:56) Distressed Investing Explained

(00:25:06) The Taxi Medallion Investment Story

(00:46:46) Navigating New York's Taxi Medallion System

(00:47:17) Building Relationships with Regulators and Unions

(00:50:22) Taking the Taxi Operation Public

(00:51:26) The Future of Autonomous Vehicles and Medallions

(00:54:30) Investment Strategies and Risk Management

(00:58:41) Negotiation Principles and Human Drama

(01:11:55) Personal Reflections and Formative Experiences

(01:17:22) The State of the American Economy

(01:23:29) Insights on Private Credit and Equity Markets

(01:30:39) Future of Asset Management

(01:33:16) The Kindest Thing Anyone Has Done For Andrew