Andrew Milgram - Full-Contact Capitalism - [Invest Like the Best, EP.436]

Invest Like the Best with Patrick O'Shaughnessy

Colossus

Investing, Business, Technology

4.8 • 2.4K Ratings

🗓️ 5 August 2025

⏱️ 94 minutes

🔗️ Recording | iTunes | RSS

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Summary

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

Transcript

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0:00.0	The best operators have a relentless focus on leverage, finding ways to multiply their impact
0:04.7	rather than just working harder. But here's what I see happening in finance teams everywhere,
0:09.0	brilliant people getting buried in expense management busy work. If you think about it,
0:12.8	you become a finance leader because you love strategic work, modeling scenarios, optimizing capital
0:17.2	allocation, finding the insights that actually move the business forward. But instead,
0:20.8	you're chasing receipts and categorizing transactions.
0:23.1	It's the opposite of leverage.
0:24.8	This is exactly why I'm so bullish on what the team at Ramp has built.
0:28.5	Kareem and Eric understood that every minute spent on manual expense management is a minute
0:32.4	stolen from high leverage work.
0:34.0	So they automated all of it.
0:35.6	Automatic categorization, receipt matching, spending controls that
0:38.6	actually work. I love the network effect that this creates. When finance teams at companies like Shopify
0:43.7	and Stripe automate the mundane stuff, they free up cycles to think bigger, to ask for your questions,
0:48.5	spot patterns others miss, and make the kind of strategic bets that separate great companies from good
0:53.0	ones. The math is simple. Get your time back, focus on what matters.
0:57.2	Check out ramp.com slash invest and see what happens when you eliminate the busy work.
1:02.2	Ridgeline is hosting their annual Basecamp conference this September 22nd through the 25th in Deer Valley, Utah.
1:08.7	I will be there on Seoul over 50 top investment management firms from
1:12.0	around the country. Now in its fourth year, Basecamp has become where the future of investment
1:16.1	management is created. Ridgline gets the most influential change makers in the same room learning and
1:20.6	sharing ideas about the latest innovations that are drastically altering how this industry operates.
	...

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