Real Estate Underground

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 not worth remodeling. Sometimes they are newer but stuck in a crowded market as the least desirable option. Sometimes they just carry too much debt. Whatever the story, the test is the same: is the ...

Most small real estate operators manage their finances by looking at what is in the bank. Money in is income, money out is expenses, and the question every Monday is how do I survive the next ninety days. Alex Lopez, CPA calls that looking in the rear-view mirror, and he spent more than a decade learning what the alternative looks like from the inside.

Alex started in real estate right out of high school during the South Florida boo...

Shams Merchant structures syndications and investment funds for clients across the country. He also runs his own fund-of-funds, allocating LP capital across about fifty sponsors, which means he sees both sides of the table: he writes the documents, and he reads other people's documents deciding whether to invest.

That vantage point is what makes this episode useful.

On AI: he gets the ChatGPT question weekly now. His answer is not th...

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 replied in five years, wrote back. That email became a data center company that has since shrunk the standard footprint by 92 percent.

That is the whole method. Rob publishes in public, constant...

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 $30,000 salary with his dad as a co-signer, rented out two of the three bedrooms, and house hacked a deal before he knew the word for it.

Then came the part nobody puts in the brochure. Three rental...

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 the whole reason this conversation is different from most multifamily interviews.

Her framework has four parts, and she looks at them in a deliberate order: the operator, the market, the numb...

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 medical residency. He is hyperlocal on purpose. He uses his own capital only. And his edge is not a list, a lead source, or a dialer. It is curiosity applied to public records, specifically plannin...

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 have to be sold at a loss. He sat his wife down and told her, and he watched her fall back in her chair. What followed was months of depression he describes without flinching in this conversation. ...

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 Jake, set hard parameters, and built a repeatable process for buying multifamily from mom-and-pop owners. That framework carried them through the last cycle without the blowups so many operator...

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 found a wholesaler in the newspaper, contracted the house, and jumped in with both feet while everyone around him begged him not to. Twenty-eight years and thousands of flips later, he calls...

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 team that has spent ten years building a full turnkey operation on the ground in Michigan.

The thesis is contrarian and simple. While most people wrote Detroit off, James and Voytek heard it was in the early innings of recovery, dr...

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...