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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 it, people pay back loans, not properties. The building is collateral and a secondary source of repayment. The person is the deal.
The lender's opening question is the one most passive investors never ask: how do I lose money on this? Not what is the projected return. What is the downside, and where does it come from.
She is direct about where LPs get hurt. The preferred return is not guaranteed, and a lot of investors believe it is. She walks through both waterfalls, the capital event and the cash flow, and what she wants to see about priority when a deal is stressed rather than when it performs. She has walked away from deals where the sponsor checked out and the numbers checked out but the structure did not align.
She also talks about fraud, from both sides. She caught it as a lender. She was a victim of it as a passive investor. That is in the new book, and she does not soften it.
Her latest, The Busy Professional's Guide to Passive Apartment Investing, is written for the doctor, lawyer, accountant, or executive working an eighty-hour week who wants real estate exposure without becoming an operator. Each chapter stands on its own so it works as a reference rather than a front-to-back read. Her first book, Mastering Multifamily Underwriting, is an Amazon bestseller and goes deep on the deal analysis itself. Both are on Amazon in all four formats.
We also get into what changed in her 2026 underwriting on rates and insurance, why she wants insurance modeled well above the standard three percent, why she will not invest where the operator has no local infrastructure, and what a decade of watching LPs lose money taught her about protecting capital.
Connect with Vessi Kapoulian:
dbacapitalgroup.com
masteringmultifamilyunderwriting.com
LinkedIn
Chapters
00:00 A lot of fraud, a lot of scams emerge in this part of the cycle
00:45 Welcome to Real Estate Underground
01:00 A returning guest: Vessi Kapoulian
01:30 Bulgaria, the Iron Curtain, and what it shaped
02:30 Fifteen years underwriting, then buying for her own account
04:00 Parallel paths: Clark St moves to the lending side
04:30 Why she wrote Mastering Multifamily Underwriting
07:00 The four areas, in order: operator, market, numbers, structure
08:00 People pay back loans, not properties
09:00 The Busy Professional's Guide to Passive Apartment Investing
11:00 Fraud, from both sides of the table
12:00 What a lender sees that a syndicator pitching LPs does not
14:00 Following the deck versus reading the documents
15:00 Both waterfalls, and why the preferred return is not guaranteed
17:00 Fees, alignment of incentives, and capital call conditions
18:00 Florida, Georgia, Tennessee, run from Los Angeles
19:00 Why she starts with local boots on the ground
20:00 Underwriting rates and insurance in 2026
22:00 Losing money, and why nobody has until they do
24:00 FOMO, and the deal you should regret more
27:00 Transparency after a loss, and the venture rule about cycled founders
29:00 The Final Five
29:30 Purpose: lasting positive impact
31:00 Best advice: you will get ready when the opportunity is presented
33:00 The decision she would take back, and God's timing
35:00 What is on the nightstand
36:30 Defining success: a life of significance
36:50 Life outside real estate: running, reading, family
37:30 How to reach Vessi
Vessi's books:
The Busy Professional's Guide to Passive Apartment Investing
Mastering Multifamily Underwriting
This week's books: The Family Office Handbook by Kirby Rosplock, and Raising Financially Fit Kids by Jolene Godfrey.
Real Estate Underground with Ed Mathews. Find us wherever you get your podcasts, at clarkst.com/podcast or elevista.com/podcast
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Heads up: If you find this week's book intriguing and you buy using our link, we receive a small commission that helps support the show. Thank you!
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 is how the subdivision deal happened. A 0.9-acre parcel had been sitting on Zillow for six months, a block from a hospital, on town water and sewer, with the house pushed to one edge of the lot line. Jordan asked whether the town would allow a split, paid for a survey, presented to the planning board, and walked out with three lots where there had been one. A nurse at that hospital is going to build on one of them. The developer who owns 200 units nearby, and drove past that property roughly a thousand times a year, is buying the other.
Jordan is also candid about the loss. He needed a zoning variance on a downtown building that should have been four units. A neighbor organized twenty households, the room was the fullest the board had seen in years, and Jordan walked away from the deal. Then he stayed until 11 PM to talk with everyone who had spoken against him.
We also get into his B-class thesis, why he passed on a hundred units and does not regret it as much as you would think, how a busy physician finds deals in what he calls the interstitium, and the rule his grandfather gave him: always know where the exit is.
Connect with Dr. Jordan Romano:
Chapters
This week's book: The Almanac of Naval Ravikant by Eric Jorgenson
Also mentioned: Thinking in Bets by Annie Duke, and Am I Being Too Subtle? by Sam Zell.
Real Estate Underground with Ed Mathews. Find us wherever you get your podcasts, at clarkst.com/podcast or elevista.com/podcast
Elevista - Speed as a Service™
Elevista Connect is the first AI-powered lead conversion system built for real estate investors.
🎧 Subscribe to Real Estate Underground for weekly insights on building wealth through real estate, without sacrificing your sanity.
Additional Resources:
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Heads up: If you find this week's book intriguing and you buy using our link, we receive a small commission that helps support the show. Thank you!
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 reach: the problem was not real estate, it was the way he was structuring the deals.
Today Joel and his team at Brit Properties buy small single-tenant industrial buildings in Chicago, and they buy three out of every four of them with no debt at all. The ceiling is 30% loan-to-value. That boundary is not a strategy so much as a mental health requirement, and he is refreshingly blunt that it costs him upside.
He is also one of maybe five syndicators in the country doing it. He does not know who the other four are.
This is Joel's second appearance on the show. After the first one, Ed changed how Clark St underwrites deals. That is not a marketing line, it is what happened.
What we get into:
Lightning round: the mentors (the Podolsky family, and 99-year-old Nate Wagner, who Joel has bought breakfast nearly every Saturday for 15 years), the deal he wants back, the book on his nightstand, and how he defines success.
Connect with Joel Friedland
Brit Properties: britproperties.com
Book mentioned
1929 by Andrew Ross Sorkin: find it on Amazon
Connect with Ed Mathews and Clark St Capital
Website: clarkst.com
Newsletter: Underground Insights
Submit a deal: clarkst.com/submit-your-deal
Elevista - Speed as a Service™
Elevista Connect is the first AI-powered lead conversion system built for real estate investors.
🎧 Subscribe to Real Estate Underground for weekly insights on building wealth through real estate, without sacrificing your sanity.
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Heads up: If you find this week's book intriguing and you buy using our link, we receive a small commission that helps support the show. Thank you!
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 2,600 units, owns 1,900, and his students have closed over 90,000 units and raised more than $800 million.
This week on Real Estate Underground, Gino sits down with Ed Mathews to talk about the mindset underneath the numbers. His through line is simple and uncomfortable: money does not corrupt a person, it reveals them. And the reason two investors with the same deal get different outcomes usually comes down to what Gino calls financial flashpoints, the money memories each of us was raised inside. Save for a rainy day, money does not grow on trees, it takes money to make money. Gino spent years unlearning those beliefs before he could raise capital, syndicate, and build the portfolio he has now.
What you will learn:
Why your relationship with money, not your spreadsheet, decides whether you close deals, and how to spot the beliefs quietly holding you back. The mind shift from starting a business to make money to starting one to deliver value, and why Gino says it is the difference between one restaurant and six. Why the market moved from valuation through renovation to valuation through operations, and what that means for how you win now. The velocity of money, why you only make money when you exit, and the three things worth doing with capital after a sale. And why no deal is better than a bad deal, and how the ten-minute no became a superpower in a market where sellers still think it is 2021.
Gino also shares the money-coaching business he is building with his wife and son at Barbaro360, why he believes legacy is not something you leave behind but something you activate today, and the six-acre farm in Florida where he goes to get his hands dirty. As he puts it, if you want to learn from someone, just make sure they are still doing it right now.
If you are an operator trying to build something that lasts, this one is full of hard-won lessons from someone still in the work.
Chapters
This week's book: The Psychology of Money by Morgan Housel
More Real Estate Underground episodes: clarkst.com/podcast
Elevista - Speed as a Service™
Elevista Connect is the first AI-powered lead conversion system built for real estate investors.
🎧 Subscribe to Real Estate Underground for weekly insights on building wealth through real estate, without sacrificing your sanity.
Additional Resources:
Social Media:
Heads up: If you find this week's book intriguing and you buy using our link, we receive a small commission that helps support the show. Thank you!
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 Estate Underground, Ed Mathews sits down with Robbie, the operator behind The FlipFlop Flipper, to talk about what it actually takes to run a lean flipping business at scale. Robbie spent two decades buying a couple of houses a week at Florida foreclosure sales. When the auctions moved online and margins got squeezed, he relocated to the island of Puerto Rico and started buying what locals call zombie houses: abandoned homes with no doors, no windows, no power, and nothing but upside. He renovates them back to the point where a first-time buyer can get an FHA loan, then hands over the keys.
What you will learn:
Why a 28-year operator who does not even carry a laptop has his team using AI every day, and why he believes anyone who refuses to learn it will be left at a disadvantage. The three-question filter Robbie runs before entering any new market: will our money go further, can we make a bigger return, and will our impact be one we are proud of. The single biggest mistake of his career, flipping a thousand houses before 2007 and keeping none of them, then losing everything in the crash. How he rebuilt by partnering with people who had capital instead of borrowing hard money, and started investing for cash flow instead of chunks of money. And the closing-table moment that still makes every renovation worth it.
Robbie also shares the story behind a little red brick house in Ukraine. On a humanitarian trip in 2022 he helped a pastor buy a home big enough to adopt three boys out of an orphanage. That same house now shelters and feeds 70 orphans. As Robbie says, every house has a story, and that one is pretty good.
The lightning round covers the joy of missing out, why he says no to most deals that cross his desk, the book he has read front to back five times, and how he defines success now that boats and fast cars stopped mattering.
If you are an operator trying to build something that lasts, this one is full of hard-won lessons from someone still in the work. Find Robbie inside his free FlipFlop Flipper community on Skool, or on YouTube.
Chapters
This week's book: Think and Grow Rich by Napoleon Hill
More Real Estate Underground episodes: clarkst.com/podcast
Elevista - Speed as a Service™
Elevista Connect is the first AI-powered lead conversion system built for real estate investors.
🎧 Subscribe to Real Estate Underground for weekly insights on building wealth through real estate, without sacrificing your sanity.
Additional Resources:
Social Media:
Heads up: If you find this week's book intriguing and you buy using our link, we receive a small commission that helps support the show. Thank you!
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 beautiful colonials in strong historic neighborhoods trading below the cost of construction. They sold off assets elsewhere, including a primary residence, and bought heavy. Ten years and 600-plus renovated homes later, they run a system that takes an investor from a first phone call to a cash-flowing landlord in 30 to 45 days.
This episode is a practical map of remote and cross-border investing. You will hear how they vet a property with a 300-point pre-purchase inspection and block-level analysis, how a foreign national forms a US entity to qualify for financing, and why they refinance instead of flip to scale a portfolio. Voytek breaks down Detroit's 55,000-room hotel shortage against 17 million annual visitors and how that gap feeds their short-term rental strategy. Then the pair walk through the tax stack: opportunity zones that can wipe out capital gains after ten years, and bonus depreciation that can cover a down payment in year one.
The Final Five turns personal: working alongside a lifelong best friend, the books that shaped them, and Voytek's deep dive into AI, which he calls the single most revolutionary tool of his lifetime.
Find them at USProperties.ca.
Chapters
00:00 The most undervalued market in the country
01:00 Welcome to the Real Estate Underground
02:00 Meet James Lloyd, Voytek Mardula, and US Properties
03:00 Why Detroit: the contrarian comeback thesis
05:00 Buying the right house in the right neighborhood
08:00 Managing a remote portfolio with a local team
11:00 The investor journey from first call to cash flow
13:00 The full turnkey system, step by step
14:00 Foreign nationals and US entity formation
16:00 Buy, hold, and refinance to scale
18:00 Short-term rentals and Detroit's hotel shortage
22:00 Opportunity zones and bonus depreciation
26:00 The auto industry and tech sector renaissance
31:00 The final five
32:00 What gets them out of bed
36:00 A decision they would take back
37:00 AI obsession and the book on the nightstand
40:00 Defining success and life off the clock
42:00 How to reach US Properties
This week's book: You to the Power of Two: Redefining Human Potential in the Age of AI by Joseph Bradley and Don Tapscott
More Real Estate Underground episodes: clarkst.com/podcast
Elevista: elevista.com/podcast
Elevista - Speed as a Service™
Elevista Connect is the first AI-powered lead conversion system built for real estate investors.
🎧 Subscribe to Real Estate Underground for weekly insights on building wealth through real estate, without sacrificing your sanity.
Additional Resources:
Social Media:
Heads up: If you find this week's book intriguing and you buy using our link, we receive a small commission that helps support the show. Thank you!
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: multifamily, self-storage, mobile home parks, medical office, and private lending. His pitch is simple. Real diversification is not large cap versus small cap or value versus growth. It is owning assets that do not move when a headline does. As Tom puts it, a tsunami hitting Japan can knock the stock market down 15 percent overnight, but it does nothing to an apartment building in Phoenix or a storage facility in North Carolina.
The backbone of the episode is Tom's SAFE Investing Method, the same screen he uses every day. S is for sponsor: who are you writing the check to, what is their track record, and have you earned the right to ask the hard questions. A is for asset: if you cannot explain the investment to your kid or your elderly parent, you do not understand it well enough to fund it. F is for financials: do the projections hold up, and has this sponsor actually hit numbers like these before. E is for exit: you cannot click your way out of a syndication on a Tuesday afternoon, so you need to know exactly what has to happen, and over what time horizon, before your money comes back.
Then Tom goes off the mainstream script on taxes. The standard advice is to 1031 exchange again and again until you die and hand your heirs a stepped-up basis. Tom's question is blunt: do you really want to be managing properties at 90 the way his mother could be. He prefers the lazy man's 1031, taking the gain, then using fresh depreciation from the next deal to shelter income, all without the rigid timelines and same-title rules that make a true 1031 nearly impossible across a group of 20 or 30 investors. Pay the freedom tax, he argues, and buy yourself passive income and time.
The buy box conversation is just as practical. Tom likes private lending for first-position security and monthly checks. He likes mobile home parks and co-living because they answer the housing affordability crisis with real, unsubsidized supply, and he breaks down how a Philadelphia operator turns a $1,000 row home into $3,000 a month by renting furnished rooms to tenants on fixed income. He covers where self-storage sits after its boom and consolidation, and why he treats it like multifamily underwriting now.
On technology, Tom is candid that he is still early but already getting leverage from AI. His current workflow is to go back and forth with Claude to build a long, specific prompt, then hand it to Manus for deep research on a market like Phoenix multifamily. He even has an AI clone at tomdunkel.ai that will answer your investing questions, as long as you do not bring up the Eagles.
The lightning round digs into purpose beyond family, the best advice he ever got from a nine-figure investor, a job he probably should have turned down, and how he defines success now as an empty nester: geographic and time freedom, plus the room to give back through Tunnel to Towers and a scholarship he started for a friend lost to ALS.
Find Tom at investwitheagle.com, grab his book The Wealth Builder's Playbook, or talk to his clone at tomdunkel.ai.
Chapters
This week's book: Invest Like a Billionaire: Unlocking the Wealth Secrets of the Ultra-Rich by Bob Fraser and Ben Fraser
More Real Estate Underground episodes: clarkst.com/podcast
Elevista - Speed as a Service™
Elevista Connect is the first AI-powered lead conversion system built for real estate investors.
🎧 Subscribe to Real Estate Underground for weekly insights on building wealth through real estate, without sacrificing your sanity.
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Heads up: If you find this week's book intriguing and you buy using our link, we receive a small commission that helps support the show. Thank you!
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, South Africa, the Philippines, and South America—while the owner still controls the housekeepers and maintenance on the ground.
In this episode, Tim and Ed get into why “a B-class property with A-class management beats an A-class property with B-class management,” why the urban short-term rental market is more durable than the vacation-rental crowd realizes, and what the data is actually telling operators about which markets to enter and which to avoid.
What you’ll hear:
Books Tim recommended:
About Tim Hubbard: CEO and co-founder of Corzly. 16-year real estate operator. Host of Short Term Rental Riches, a six-year-old podcast covering virtual STR management, market selection, and the operational discipline behind scaled portfolios.
Find Tim: corsley.com | Short Term Rental Riches podcast (all platforms + YouTube)
Subscribe to Real Estate Underground for weekly conversations with operators who’ve been through the cycle and lived to talk about it.
Elevista - Speed as a Service™
Elevista Connect is the first AI-powered lead conversion system built for real estate investors.
🎧 Subscribe to Real Estate Underground for weekly insights on building wealth through real estate, without sacrificing your sanity.
Additional Resources:
Social Media:
Heads up: If you find this week's book intriguing and you buy using our link, we receive a small commission that helps support the show. Thank you!
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 producing passive income.
Today Dan co-leads Granite Towers Equity Group, a 3,300-unit multifamily portfolio focused on Dallas-Fort Worth, Nashville, and select Minnesota submarkets. The playbook is disciplined: newer assets (1985 and up), 140 to 300 units, $20 to $40 million purchase price, 95%+ occupancy submarkets with real pent-up demand. Eighty-twenty split with LPs. Sixty-five to seventy-five percent loan-to-value, fixed rate, non-recourse. CapEx raised liquid up front, so the bank cannot force a bad spend.
What you'll hear:
Learn more about Granite Towers Equity Group: https://www.granitetowersequitygroup.com/contact-us
Elevista - Speed as a Service™
Elevista Connect is the first AI-powered lead conversion system built for real estate investors.
🎧 Subscribe to Real Estate Underground for weekly insights on building wealth through real estate, without sacrificing your sanity.
Additional Resources:
Social Media:
Heads up: If you find this week's book intriguing and you buy using our link, we receive a small commission that helps support the show. Thank you!
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 and JB unpack a contrarian lesson the real estate education industry rarely teaches: the difference between the real estate hustle and the real estate business. Hustle gets you doors. Business gets you a sustainable enterprise. Most operators only ever learn the first one.
JB walks through the Houston duplex pricing math that vindicated his long conviction on the market, from "praying to get $350" on a 2,500 square foot duplex to selling at $479, almost $500,000. He explains his concept-to-keys pocket-development model, Houston's no-zoning-but-deed-restrictions quirk, the 60/40 build-to-sell vs. build-to-hold split for his client base, and why vertical integration (owning the GC) is a margin lever most flippers underestimate.
In this episode:
If you're a flipper, wholesaler, or operator trying to build a business and not just a deal pipeline, this is the episode.
This week's book: The Miracle Morning by Hal Elrod
Guest: JB Thibodeaux, Founder & Managing Partner, J.B. Thibodeaux Homes & Properties
Website: jbthibodeaux.com
LinkedIn: linkedin.com/in/james-thibodeaux-8a98b51b7
Instagram: @jbthibodeauxhomes
Elevista - Speed as a Service™
Elevista Connect is the first AI-powered lead conversion system built for real estate investors.
🎧 Subscribe to Real Estate Underground for weekly insights on building wealth through real estate, without sacrificing your sanity.
Additional Resources:
Social Media:
Heads up: If you find this week's book intriguing and you buy using our link, we receive a small commission that helps support the show. Thank you!
From the publisher's feed
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,…
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)
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.