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 numbers, and last, the structure of the deal. Last. As she puts...
Jul 28
39 min
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 planning and zoning board minutes that almost nobody reads.
That i...
Jul 21
45 min
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. He came out of it with a conclusion most investors never reac...
Jul 14
52 min
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 operators are living through now. Today Gino has transacted more than ...
Jul 7
39 min
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 it one of the best deals he ever did.
This week on Real Est...
Jun 30
34 min
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, drove down to see it for themselves, and found architecturally ...
Jun 23
44 min
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 experience to place money into alternatives most people never see: mu...
Jun 16
40 min
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, guest communication, and back-end operations across Eastern Europe...
Jun 9
28 min
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 his snowboarding career ended, he had 70-some units already p...
Jun 2
42 min
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 Houston market crowned him the "Duplex King." In this episode, Ed an...
May 26
42 min
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