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 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 weekly.

Host

Ed Mathews

Ed Mathews spent 24 years in Silicon Valley, where he learned one truth: First movers win.

He carried that into real estate when he bought his first CT rental property in 2011. Deal by deal, he built a portfolio across New England under Clark St Capital. In 2018, he left corporate for good.

Then, one deal pulled him back into tech. He put his phone away to watch his daughter's softball game. When he called back 90 minutes later, the seller was already with another buyer. That delay cost him $57,000.

Ed didn't get angry. He got to work.

That loss became the founding story of Elevista. His AI voice agent, Katie, now calls leads back within 60 seconds, qualifying sellers, booking appointments, and logging everything, even when Ed can't.

The Real Estate Underground podcast exists for the same reason: real operators, real deals, real lessons. No fluff. No theory. Just what actually moves the needle.

https://www.clarkst.com