Real Estate Underground

Ashley Romiti is the president and founder of GCA 1031, where she works primarily with retiring real estate investors who want to reposition their portfolios. Most of them have held their properties for a long time, and the hard part isn't the tax code. In her words: "The big thing they're giving up is control." Ashley defines the 1031 exchange, the Delaware Statutory Trust and...

Amar Patel is a CPA and one of the partners at KBKG, where he heads up the Southeast cost segregation practice out of Atlanta. He spends his days inside other people's depreciation schedules, and the first thing he looks for is one line labeled "building" being written off over 27 and a half or 39 years. His point for anyone who skipped the study at closing: "It's kind of...

Stephen Morel has spent more than 20 years as a Louisiana title attorney working in the messiest corner of title work: delinquent tax sale titles. He helped rewrite Louisiana's tax sale law, and after Hurricane Katrina he built a title insurance program that put abandoned, forgotten properties back into the stream of commerce. Now he runs JurisDeed. His opening point is the one most tax lien...

Nasir Ali runs Rise360 Ventures. He comes from eight generations in commercial real estate and is the second generation in manufactured housing, a business his family just marked 45 years in, through at least nine downturns. His case for the asset class is simple. "We own the land. And sure the common areas and whatnot, but essentially we're renting dirt." No plumbing, no electrical...

Forrest Jinks runs Altus Equity Group, a real estate investment company that works with family offices and high net worth investors. Most sponsors chase top-line IRR: get in, get out in two, three or four years. Forrest says that leaves a lot of meat on the bone. "It might be awesome to get an 18% return over 10 years versus a 20% return in three." He cares about the net return, after ta...

Palmy Kitti and her sister Nan started a fashion business with $2,000. Years later their biggest client shut down all its retail stores and 95% of their income was gone overnight. They moved into flipping houses in Los Angeles, then into multifamily syndication. Seven and a half years in, Palmy says they have nearly half a billion dollars in assets under management across Georgia, Arkansas and Tex...

Jason Williams spent 15 years as a chemical engineer. He's owned real estate since 2003 and large multifamily since 2017. When he started underwriting apartments, half the spreadsheets he was handed had broken cells and equations that didn't work, so he built his own model. People kept asking him to show them how it worked, and that model became Ironclad Underwriting. His rule is simple:...

Stewart Heath, CPA went into 2008 over-levered and under-reserved. He handed buildings back to the banks. He says that for want of roughly $300,000 in reserves he would still own them, and every rule he operates by now was built backward from that number. His book is called "Don't Do What I Did." Stewart runs Harvard Grace Capital out of Spring Hill, Tennessee, buying stabilized com...

Twenty-five years ago Jeff Emalaba was a guest host on CNBC Africa, analyzing derivatives, commodities and futures, and holding an options license in Florida. He describes all of it as one subject: risk transference. That is the lens he brought to real estate, which makes what happened next harder to explain and more useful to hear. He drove two hours to see a duplex in North Carolina and walked i...

Mark Khuri co-founded SMK Capital Management with his father, Dr. Suheil Khuri, pooling family capital informally before opening the firm's doors in 2010. They operated properties directly through 2017, then pivoted entirely to the LP side. Today SMK reviews 600 to 700 private real estate deals a year and invests in roughly 1 to 2% of them, call it 5 to 10 deals annually, across diversified f...

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 st...

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...

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...

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....

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 nobod...

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...

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 pu...

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 with...

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 w...

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...

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 i...

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...

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...

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...

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...