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
How a PhD Underwrites Apartments: Jason Williams of Ironclad Underwriting
Jason Williams spent 15 years as a chemical engineer. He's owned real estate since 2003 and large multifamily since 2017. When he started underwriting apartments, half the spreadsheets he was handed had broken cells and equations that didn't wo...
Boring Is Beautiful: Stewart Heath on 13% Cash on Cash and the $300,000 He Did Not Have
Stewart Heath, CPA went into 2008 over-levered and under-reserved. He handed buildings back to the banks. He says that for want of roughly $300,000 in reserves he would still own them, and every rule he operates by now was built backward from t...
The inspector told Jeff Emalaba to run. Confirmation bias cost Jeff $11,000.
Twenty-five years ago Jeff Emalaba was a guest host on CNBC Africa, analyzing derivatives, commodities and futures, and holding an options license in Florida. He describes all of it as one subject: risk transference. That is the lens he brought...
Mark Khuri reviews up to 700 deals a year. He invests in 10. Here's his filter.
Mark Khuri co-founded SMK Capital Management with his father, Dr. Suheil Khuri, pooling family capital informally before opening the firm's doors in 2010. They operated properties directly through 2017, then pivoted entirely to the LP side. Tod...
$30,000 a Door: Dr. Alex Cartwright Brings Dead Hotels Back to Life
Most people hear hotel conversion and picture a novelty deal. Dr. Alex Cartwright built a company around it, and the reason is arbitrage that is not subtle. His firm buys hotels that have no future as hotels. Sometimes they are old and ...
