June 2, 2026

From One $3M Loan to a $25B Firm - How Madison Realty Capital Was Built with Josh Zegen (# 417)

In this episode, Chris sits down with Josh Zegen, Co-Founder & Managing Principal of Madison Realty Capital, a $25 billion real estate private credit firm he started with his college roommate in 2004. They dig into how he built one of the largest private lenders in the country starting from a desk in his dad's law office - and why he still thinks of himself as a businessman first and a real estate guy second.

Josh got into lending almost by accident. Laid off from a VC firm at 26 when the dot-com bubble burst, he took one mortgage deal nobody else would do, saw how fragmented and non-institutional the market was, and built a fund around it before "private credit" meant anything. Chris and Josh go deep on surviving '08, reinventing the business when capital dried up, and how Madison grew into a platform that now lends to other lenders.

They discuss:

How Josh went from a laid-off VC associate living back home to founding a $25B firm
Surviving '09 - including giving up 50% of the company for a $50M anchor that collapsed at the last minute
Why he built servicing, asset management, and capital raising in-house instead of outsourcing
The $10B back-leverage book that makes Madison the lender to ~100 other private lenders
The $720M single loan behind the largest office-to-residential conversion in NYC
Where he sees real estate credit headed - and why he stays away from office, data centers, and anything "binary"

Timestamps:
(00:00) Intro
(00:52) Rate Volatility and a Stalled CRE Investment Market
(09:44) What's Getting Done Today: Construction, Conversions, and Recaps
(18:49) Founding Madison: Seeing Opportunity in a Fragmented Market
(25:19) The GFC: Gating Investors and Going Vertically Integrated
(31:26) The $50M REIT Deal That Nearly Ended Madison—And the Door It Opened
(44:28) Why Borrowers Now Prefer Private Credit Over Banks
(47:17) In-House Loan Servicing as Madison's Competitive Edge
(49:06) The Back Leverage Business: Lending to Private Lenders
(55:35) Capital Markets Expansion and Staying True to Real Estate
(1:05:55) The Pfizer Deal, Lifecycle Lending, and Madison's Road Ahead
(1:15:06) Staying Relevant by Constantly Innovating and Looking for Acquisition Opportunities

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