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One of the craziest investing stories I’ve heard in this episode
- uber ascendant in NYC in 2016.
- taxi mediation owners levered them and defaulted
- andrew went and got the ride by ride data for every taxi and uber that no one had ever asked for before
- figured out things had stabilized, medallions worth more than fear driven prices suggest
- bank desperately wanted to get rid of the defaulted medallions
- he pays a “Milgram price” to buy them in bulk
- uses data to help cabs drive optimal routes including the “nascar loop”
- invests to become the best fleet operator for drivers
- ipos the whole portfolio for huge return
Whole wild ride detailed in the epsidoe. One of those stories where you can FEEL the investing return being earned.

5.8. klo 20.00
Today’s guest, Andrew Milgram, spent $600M buying NYC taxi medallions at the peak of Uber's power—an investment which gives you a sense of Andrew’s style.
He describes a “K-shaped economy,” where one small group of companies does incredibly well while the rest struggle.
Amidst it all he tries to build unique views in unexplored areas—be that Native American gaming, tax credits, regulatory gaps, or taxis.
If you are interested in distressed investing, or the economy outside MAG7 and AI, this is a great listen.
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
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