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
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...
Money Reveals You: Gino Barbaro on the Mindset Behind 2,600 Units
Gino Barbaro is a best-selling author and co-founder of Jake & Gino, but he did not start there. He opened a restaurant with his family in 1994, lost money on his early real estate deals, and only found his footing when he partnered with Ja...
3,000 Flips, Zero Tech Background: How Robbie Crager Uses AI to Scale
Robbie Crager bought his first house at 25 with no money, bad credit, and no idea what he was doing. He had just lost a corporate job and had watched Carlton Sheets on late-night television promise he could buy a house with no money down. So he...
Detroit's Comeback: Turnkey Cash Flow in America's Most Undervalued Market
For the 200th episode of the Real Estate Underground, the conversation lands on a city near and dear to Ed's heart: Detroit. His guests are James Lloyd and Voytek Mardula of US Properties, a Toronto-based t...
