Invest Like the Best with Patrick O'Shaughnessy
Andrew Milgram - Full-Contact Capitalism - [Invest Like the Best, EP.436]
05 Aug 2025
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. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Ramp. Ramp’s mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to Ramp.com/invest to sign up for free and get a $250 welcome bonus. – This episode is brought to you by Ridgeline. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Head to ridgelineapps.com to learn more about the platform. – This episode is brought to you by AlphaSense. AlphaSense has completely transformed the research process with cutting-edge AI technology and a vast collection of top-tier, reliable business content. Invest Like the Best listeners can get a free trial now at Alpha-Sense.com/Invest and experience firsthand how AlphaSense and Tegus help you make smarter decisions faster. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). 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
Chapter 1: What is the main topic discussed in this episode?
The best operators have a relentless focus on leverage, finding ways to multiply their impact rather than just working harder. But here's what I see happening in finance teams everywhere. Brilliant people getting buried in expense management busywork. If you think about it, you become a finance leader because you love strategic work.
Chapter 2: What is the K-shaped economy and how does it affect investments?
modeling scenarios, optimizing capital allocation, finding the insights that actually move the business forward. But instead, you're chasing receipts and categorizing transactions. It's the opposite of leverage.
Chapter 3: What challenges are faced by the middle market today?
This is exactly why I'm so bullish on what the team at Ramp has built. Kareem and Eric understood that every minute spent on manual expense management is a minute stolen from high leverage work. So they automated all of it. Automatic categorization, receipt matching, spending controls that actually work. Check out ramp.com slash invest and see what happens when you eliminate the busy work.
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Chapter 4: How is distressed investing explained by the guest?
I want to share a real-world example of how they're making a difference. Let me introduce you to Brian.
Brian, please introduce yourself and tell us a bit about your role. My name is Brian Strang. I'm the Technical Operations Lead, and I work at Congress Asset Management.
How would you describe your experience working with Ridgeline?
Ridgeline is a technology partner, not a software vendor, and the people really care. I get sales calls all the time and I ignore them. Ridgeline sold me very quickly.
Chapter 5: What is the story behind the NYC taxi medallion investment?
We went from 7 billion to 23 billion and the goal is 50 billion. Ridgeline was the clear front runner to help us scale. In your view, what most distinguishes Ridgeline? They reimagined how this industry should work. It was obvious that they were operating on another level.
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Channel checks give you a real-time, expert-driven perspective on public companies weeks before they show in earnings or consensus revisions. AlphaSense uses an AI interviewer to run thousands of expert calls with real human experts every month, asking consistent questions across experts so the signals are clean, comparable, and useful.
You get live updates as interviews come in, full transcript access and coverage across every major sector. Instantly compare insights across experts and analyze quarter over quarter trends in sentiment and key performance indicators. For investors trying to stay ahead of the fast moving markets, it's already table stakes. Hello and welcome, everyone.
I'm Patrick O'Shaughnessy, and this is Invest Like the Best. This show is an open-ended exploration of markets, ideas, stories, and strategies that will help you better invest both your time and your money. If you enjoy these conversations and want to go deeper, check out Colossus Review, our quarterly publication with in-depth profiles of the people shaping business and investing.
You can find Colossus Review along with all of our podcasts at joincolossus.com.
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Chapter 6: How does Marblegate navigate negotiations in distressed situations?
To learn more, visit psum.vc.
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% to 25% since 2019, creating what he calls the K-shaped economy.
His investment stories are legendary, particularly his $600 million bet on New York City 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 distress situations. Please enjoy this great conversation with Andrew Milgram.
Andrew, I think you and I have talked about doing this for five years.
Chapter 7: What investment strategies and risk management practices does Marblegate employ?
On and off, I think that's right. You don't do this a lot or ever. I love the category of guests that are the first and only interviews of this type. And so I'm so excited to do it with you.
Chapter 8: What are the personal reflections and formative experiences of Andrew Milgram?
And I'm especially excited because your style is so distinctive. And we'll talk about a million things related to how you invest and your personal story and getting here. But I thought a framing exercise that would be great starting place would be for you to describe this notion that you have of the K-shaped economy.
You do something that's very specific, and we're going to talk about all aspects, but I want to start broad. So tell us what the K-shaped economy is from your perspective.
Yeah, so it's a notion we talk a lot about with investors and with the companies that we invest in. Everybody in the U.S. economy, at least, has this underlying sense that there are some parts of our economy that are doing exceptionally well.
But at the same time, they have this internal notion that there are other parts that are just worse than it seems, that there's a nagging slowness or a nagging underperformance to the economy in broad areas. They can't quite put their finger on it because they look at CNBC and Bloomberg and they read the Wall Street Journal and there's green arrows in the ticker tape economy. Those companies and
those wealthy individuals who have access to capital, who have access to resources, and can drive unbelievable profits and great outcomes.
But there's a broad part of the economy, and I think we see this in the political sector being expressed pretty acutely, the broad pieces of the economy that are just dissatisfied with their earnings power, with their ability to benefit from the promise of the American economic system.
that discrepancy i think is really hard for people to understand but when we say k-shaped economy it immediately resonates with people because they see it themselves they feel it in real time they understand intuitively that there are those who are having fabulous success but they also understand that there are people and companies that are just not getting their piece of the pie there's this amazing data set that you've just spent time exploring i want you to explain the data set and then all the findings
What I want you to focus on is, so if you think about the K-shape, we all know the upper part. It's the S&P 8 or as people are calling it now, FANG stocks or whatever, AI companies. We know the story that's going well. So maybe talk about this investigation that you've done recently about what's going less well and why and what you learned.
Well, I'll start with at MarbleGate, we focus on the middle market. And the reason we focus on the middle market is, A, it's one-third of U.S. economy. And by the way, over time, it has represented something north of two-thirds of all restructurings, bankruptcies, etc. So it's the area of the most, let's say, action. It's also the area of the economy people know the least amount about.
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