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.

So much wisdom here📝 For example: “Well, defaults are the most easily manipulated statistic in the world. A default doesn't exist unless I, the lender, call it. If I don't want defaults in my portfolio, I simply don't call them.” “I always tell people, don't ask the default rate of a private credit, ask the waiver rate, ask the amendment rate. How much are they having to put hands on their credit to reorient the documents, to fit the reality of the company they're operating in?” 🎯

I know Andrew relatively well, and happen to know Patrick too. Andrew is incredibly sharp and a fantastic distressed investor. I would consider him one of the most well educated people I know in the middle-market. I am deeply looking forward to listening.

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

Prefill on Etched Decode on Cerebras / Groq Would be the most gigabrain inference setup ever and maybe even cost effective

On the power of backing dilution sensitive founders

Such a fascinating lens into how venture actually works vs. how people think it should work. Deep discussion the new venture math and on pattern matching/arbitraging talent and opportunity for upstream capital.

Had a fantastic conversation with @patrick_oshag! We dove deep into my personal journey and the origins of Abstract, exploring how it has grown into what it is today.

I’m always amazed how few investors can explain the specific thing they can do better than others. When I first asked Ramtin (@ramtinnaimi) this question, he gave one of the most specific answers I’ve heard (about how he helps founders end up owning more of their company, along with his specific method for doing so). He details that and a ton more in refreshingly honest fashion. He seems willing to answer any question about himself, and we explore his entire rags to riches to rags to riches story. The stuff on the intense parallels between art and investing is a first, too: how to work the playing field and win. A unique convo with an investor who has never done an interview like this before. Timestamps 0:00 Intro 0:25 The Art of Collecting 4:36 Parallels Between Art and Venture Capital 6:59 Challenges and Strategies in Art Collecting 18:19 The Role of Status and Reputation in Art 20:10 The Business of Art Galleries & Auction Houses 26:43 Building a Successful Venture Capital Firm 41:29 Leading Seed Financings 44:27 The Power of AngelList 46:40 Scaling and Building a Team 49:33 Identifying Exceptional Founders 52:32 The Importance of Dilution Sensitivity 54:18 Efficient Investment Processes 1:05:51 Winning Competitive Deals 1:15:29 The Value of Strong Board Members 1:21:37 The Importance of Personal Branding in VC 1:24:28 The Health of the AI Investment Ecosystem 1:28:11 Early Life and Entrepreneurial Beginnings 1:35:12 Starting a Hedge Fund and Lessons Learned 1:44:59 Building Abstract and Family Life 1:54:06 Insights on LPs and Venture Capital Trends 2:02:18 The Kindest Thing

The war against slop is worth fighting