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 it with his agent. Nothing looked wrong. He asked the seller why the previous buyer had backed out...
Sep 15
45 min
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 funds, single-asset deals, and one-off syndications for their investor base. Ed and Mark get into the m...
Sep 8
40 min
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 highest and best use of this building multifamily? When the a...
Sep 1
45 min
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 boom, and he was in his early twenties when it all came down. He...
Aug 25
41 min
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 that the technology is bad, he uses it heavily. It is that a m...
Aug 18
43 min
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, constantly and for free, and lets the right people find him.
Rob ca...
Aug 11
41 min
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 rentals in an expensive market, no money left, and the discovery ...
Aug 4
49 min
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 i...
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
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