Real Estate Underground
Real talk from an operator who learned real estate the hard way.
Ed Mathews analyzed 1,100+ deals before buying his first property in 2011. Frozen in fear. He made every mistake, all while traveling 150+ nights a year working for some of Silicon Valley's top companies. 100+ deals later, he shares what actually works and what doesn't.
Each week, Ed brings you candid conversations with experienced operators, investors, and syndicators. No hype. No theory. Just real deals, real lessons, and the street-level intelligence you won't find anywhere else.
You'll learn and hear about:
Deals that worked (and the ones that didn't)
- What we learned when contractors ghosted and we had to step in
- How to vet opportunities when everyone else is sitting on the sidelines
- Conservative underwriting in markets that punish optimism
- Systems that protect capital when deals go sideways
Whether you're analyzing your first deal or your hundredth, this is the conversation you'd have over coffee with someone who's been there, made the mistakes, learned the lessons and built the track record.
New episodes every Tuesday at 12pm ET.
Real Estate Underground
Latest Episodes
Shouting Into the Void: Rob Bergeron on Unsolicited LOIs, Uniting Wholesalers, and the Good Neighbor Data Center
Rob Bergeron writes a free newsletter at five in the morning, five days a week, and has for years. One Saturday he sent it out saying he saw something happening between data and energy and wanted in. A reader named Mark, who had never once repl...
Over-Documented, Under-Underwritten: Will Harvey Rebuilds Hard Money From First Principles
Will Harvey got into real estate the way a lot of people do. He dropped out of college after a double hip surgery ended football, landed on a mortgage desk in 2015, and figured out fast how leverage worked. He bought his first house on a $30,...
"How Do I Lose Money on This Deal?" Vessi Kapoulian's Lender-First Underwriting
Vessi Kapoulian spent fifteen years as a commercial lender. She underwrote more than a thousand deals and managed a credit portfolio north of a billion dollars before she ever bought a building for her own account. That order matters, and it is...
You Don't Find a Deal, You Make a Deal: Dr. Jordan Romano's Zoning Playbook
Most investors say there are no deals. Dr. Jordan Romano says you are looking in the wrong place. Jordan is a physician in the Boston area who has spent about a decade investing in one small New Hampshire town, the town where he did his...
Debt Is Gambling: The Zero-Debt Playbook with Joel Friedland
Joel Friedland calls himself the most risk-averse real estate investor in the United States, and he has the scar tissue to prove it.In 2008 he was carrying $70 million in personal guarantees across 50 buildings. Ten of them were going to...
