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.
Episodes
If you are within three feet of Ed Mathews, you are probably talking about real estate. This week the conversation is with Tom Dunkel, managing principal at Eagle Capital Investments, and it is a clinic in how to vet a deal before a dollar leaves your account.
Tom has been a full-time investor for two decades. Over that span he has raised more than $50 million in private capital from a network of investors who lean on his experien...
Short-term rentals are supposed to be the most hands-on asset class in real estate. Tim Hubbard runs hundreds of them across the U.S. and multiple countries—without ever being on the ground.
Tim is the CEO and co-founder of Corzly, the virtual management company he built after 16 years of operating his own short-term rental portfolio from outside California, then outside the U.S. entirely. His team handles pricing, listings,...
What does it take for a professional snowboarder, six X Games appearances, gold and silver medals, fifteen years on tour, to land in real estate? For Dan Brisse, the answer was watching the guys five and ten years ahead of him lose their houses, their cars, and worse.
That was the wake-up call. While most of his peers spent every pay raise on the biggest house they could buy, Dan was reading books and buying apartments. By the time ...
JB Thibodeaux grew up in Acres Homes in Houston and is a third-generation carpenter and concrete specialist who turned that craft into a vertically-integrated real estate development business. His firms, J.B. Thibodeaux Homes & Properties, CCB Construction LLC, and CCB General Contractors LLC, have led over $100 million in projects across mass development, pocket development, and affordable housing infill. This year, the Housto...
Dan Ihara has sold over $1 billion of real estate, moved 1,600+ units, and completed 400+ 1031 exchanges—without failing a single one.
And he built the whole thing around a niche almost no operator talks about: senior-care real estate.
In this episode, Dan and Ed get into the demographic inevitability that drives his business (“should we all be blessed to live long enough, we’re going to need some level of care&rdqu...
Most multifamily operators treat internet as a tenant problem or a cost line they grumble about. Adam Bell, Founder and CEO of Internet Subway, says they're leaving real money on the table.
Adam runs a modern ISP focused exclusively on apartment communities. His company delivers fiber-to-the-unit (FTTU) in bulk to property owners, who pass it to residents as an included utility and capture the rent spread. Industry data shows 5 to 1...
Brandon Cobb's business model is simple: take farmland, get it approved for housing, and sell it to national home builders like Lennar and DR Horton. The builders have no choice but to buy. They're publicly traded. Plan A is buy land and build houses. Plan B is buy more land and build more houses. There is no Plan C that doesn't involve buying land.
Brandon returns to Real Estate Underground to break down how HPG Capital cre...
Ben Reinberg has done over $1 billion in commercial real estate transactions. He didn't get there chasing returns. He got there by treating CRE as what it actually is: a hard asset that produces cash flow, not a bet.
Ben is the Founder and CEO of Alliance CGC, where he's built one of the most respected portfolios in the country, with deep focus on net-leased properties and medical office buildings.
In this episode, Be...
Clay Lehman spent 20 years in real estate, starting at Arthur Andersen, running the Ocala controller desk for Pulte Homes, and eventually building Lehman's Strategic Partners to help agents grow their businesses. He runs an AI Facebook group with members in 65 countries and now spends most of his time helping real estate pros turn AI from a shiny object into a revenue tool. If you're still using AI to write listing descriptions and...
Joel Kraut co-founded BRRRR Loans after losing $4.2 million in the 2008 crash. He had 144 properties at over 100% leverage when the market turned. Five tenants called the same day to say they couldn't pay rent.
Today he runs one of the country's fastest-growing private lending shops, and he sees the DSCR lending industry doubling in size over the next three years.
In this episode, Joel and Ed break down:
- Why investors are rotating f...
Ladislas Maurice left a corporate career at Nestle to spend the last nine years investing in real estate across emerging and frontier markets around the world. He buys apartments in Nairobi for $65,000, sits on land in Nicaragua, and flips properties in Montenegro. His approach is the opposite of what most US investors are used to: no leverage, no perfect data, and no rushing.
In this episode, Ed and Ladislas talk about:
- Why emer...
Tyler Vinson has spent 25 years in investment real estate, from duplexes and flips to multifamily, commercial, and Class A storage. Now he's building the infrastructure to bring real estate into the digital age as the founder of RE Tokens, one of only about 10 companies in the US with an SEC-registered digital broker dealer ATS license, and the only one focused exclusively on real estate.
In this episode, Tyler breaks down w...
Ashley Garner grew up swinging a hammer on student rentals near West Virginia University. Decades later, he jumped from a 35-unit portfolio to a $21 million, 196-unit acquisition in North Carolina. In this episode, he breaks down what that leap taught him about conservative underwriting, why his dad's "cash is king" advice saved his business more than once, and how he manages a growing portfolio with a core team of three.
Wh...
Neil Henderson is a general partner and Director of Investor Relations at Nomad Capital, a Wilmington, NC-based private equity firm with a twist on self-storage: they buy vacant big-box retail buildings and convert them into climate-controlled storage facilities.
The numbers behind their model are hard to ignore. Ground-up self-storage construction runs $120-130 per square foot and takes nearly three years. Nomad's conversio...
Joe Fairless built Ashcroft Capital into one of the most recognized multifamily syndicators in the country — $2B+ in assets, properties across the Sunbelt, and a vertically integrated management company. But he started with $30K, student loans, and an apartment in New York where one paycheck covered rent and the other covered everything else.
In this episode, Joe gets candid about the deals that didn't work, the market conditi...
In this episode, Ed welcomes Michael Pouliot of Carbon Real Estate Investments, a vertically integrated private equity firm operating workforce housing apartments across the Southeast.
Pouliot explains Carbon’s buy box: 100–300 unit, older vintage (1970s–1990s) properties in strong school districts and stable submarkets, targeting families and raising rents about 20% through substantial CapEx that prioritizes...
This week, Ed welcomes Hawaii-based real estate developer and educator Fuzzy Jardine to Real Estate Underground.
Fuzzy shares his background growing up in Hawaii, getting into trouble with drugs and alcohol, going to prison, and using that time to educate himself with books like Rich Dad Poor Dad.
After struggling to find work as an ex-con, he took multiple jobs, then invested $26,000 in real estate education after hearin...
Melissa Nash spent $10K on a fully renovated $190K property with a tenant already in place.
Cash flows $200/month.
Sounds boring until you realize: $10K all-in. Someone else is buying her a house. And she never left California.
This week on Real Estate Underground: How a self-described "lazy investor" built a portfolio across five markets while coaching 2,000+ investors to do the same. No flying out to properties. No managing contract...
Mastering Short-Term Rentals with Data-Driven Real Estate Strategies - Featuring Kenny Bedwell from STR Insights
In this insightful episode of the Real Estate Underground podcast, host Ed Mathews welcomes Kenny Bedwell from STR Insights to discuss the intricacies of short-term rental investments.
Kenny shares his journey from a data analyst at Citibank to a successful real estate investor specializing in short-term rent...
What if you could turn a 10-hour due diligence process into 20 minutes of review?
Alberto Rizzoli, CEO of V7 Labs, reveals how AI workflow automation is eliminating the "purgatory" of real estate paperwork, and why operators who master it now will 10x their competition within a year.
In this episode, you'll discover:
⚡ The "napkin test" for identifying which processes to automate first (hint: weekly tasks taking 1+ hours)
⚡ Why AI fail...
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