Real Estate Underground

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Real Estate Underground episodes

  • "How Do I Lose Money on This Deal?" Vessi Kapoulian's Lender-First Underwriting

    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

    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:

    • Clark St Capital -> Passive real estate investments for busy business owners and executives
    • Elevista -> AI SaaS for real estate investors
    • Clark St Academy on YouTube -> Learn how to invest in real estate

    Social Media:

    • LinkedIn -> Ed Mathews (President at Clark St and Elevista)

    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!

    40 min
  • You Don't Find a Deal, You Make a Deal: Dr. Jordan Romano's Zoning Playbook

    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:

    medicalexpertwitness.com

    Chapters

    00:00 Always know where the exit is
    00:45 Welcome to Real Estate Underground
    01:00 Meet Dr. Jordan Romano
    01:20 A physician, a mother in real estate, and a house bought at the 2006 peak
    03:00 Invest in what you know
    04:00 Put all your eggs in one basket and watch the basket
    05:00 Why hyperlocal beats long distance
    06:00 Diners, broker opens, and off-market deal flow
    07:30 Curiosity as a sourcing engine: planning and zoning boards
    08:30 Reading the signal when a big developer expands
    09:00 The 0.9-acre lot nobody else questioned
    10:30 You don't find a deal, you make a deal
    12:50 Ed's 58-acre farm and the land he almost missed
    13:30 Zillow forensics: empty cabinets, oil heat, and a fall price cut
    14:40 Finding the time: deals in the interstitium
    16:20 Virtuous capitalism and the small-town ripple effect
    17:30 Knocking on doors before you need the vote
    18:00 The strikeout: a full room, a lost variance, a dead deal
    20:00 Staying until 11 PM to talk to everyone who opposed him
    23:00 The Final Five
    23:20 Purpose: impact you can actually see
    26:00 Best advice: his grandfather's rule
    27:00 Sam Zell on markets versus deals
    28:00 The one he'd take back: a hundred units passed on
    29:00 The B-class thesis
    30:00 Five brothers, one highway parcel, and a deal that got away
    33:20 What's on the nightstand
    36:50 Defining success: optionality and flexibility
    39:00 Life outside real estate
    42:30 Two grandfathers, two swimmers, one T-shirt
    43:50 How to reach Jordan

    This week's book: The Almanac of Naval Ravikant by Eric Jorgenson

    Get it on Amazon

    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:

    • Clark St Capital -> Passive real estate investments for busy business owners and executives
    • Elevista -> AI SaaS for real estate investors
    • Clark St Academy on YouTube -> Learn how to invest in real estate

    Social Media:

    • LinkedIn -> Ed Mathews (President at Clark St and Elevista)

    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!

    46 min
  • Debt Is Gambling: The Zero-Debt Playbook with Joel Friedland

    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:

    • Why Joel compares over-leveraged real estate investors to gamblers, right down to the part where they hide the risk from their spouses
    • The 2008 collapse in his own words, and the boundary he set on the other side of it
    • The buy box: single-tenant only, 7,000 to 30,000 square feet, no flex, no multi-tenant, and specific dock, ceiling-height and parking requirements
    • How 20 towns out of 200, and 700 buildings out of 17,000, makes the pipeline small enough to actually work, and why his team still knocks on doors to find deals
    • The secret-sauce exit: 77 of Joel's 82 sales went to owner-occupants who pay a premium over cap-rate buyers, not to investors
    • A live deal he is in the middle of on Stern Avenue, bought for $1.9M with $400K into the rehab, and the neighbor across the street who wants it
    • The Keebler building: bought for $6M, sold for $17M, a 40% IRR over a 15-year Comcast lease, and why that grand slam required the leverage he now avoids
    • Why his 250 investors, averaging roughly $20 million in net worth, are not looking to get rich, and are looking for somewhere that is not the casino
    • Reshoring, tariffs, and the honest math on why manufacturing is not all coming back
    • The batter who never strikes out

    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.

    Additional Resources:

    • Clark St Capital -> Passive real estate investments for busy business owners and executives
    • Elevista -> AI SaaS for real estate investors
    • Clark St Academy on YouTube -> Learn how to invest in real estate

    Social Media:

    • LinkedIn -> Ed Mathews (President at Clark St and Elevista)

    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!

    53 min
  • Money Reveals You: Gino Barbaro on the Mindset Behind 2,600 Units

    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

    00:00 Your relationship with money starts everything
    00:59 Welcome to Real Estate Underground
    01:40 The name, and using AI as a force multiplier
    02:40 Life before and after Jake and Gino
    03:40 Money does not corrupt you, it reveals you
    04:40 Why you really start a business: value for the marketplace
    06:00 A stuck market and the grit AI can cost you
    07:40 No motivated seller, no deal
    10:40 Financial flashpoints: the money memories that shape you
    14:30 Wealth is an exchange of value
    16:20 Valuation through renovation vs valuation through operations
    19:40 Velocity of money: what to do after you exit
    22:40 Paying down debt as a legacy play
    24:40 Retail, industrial, and the discipline to wait
    29:20 The final five: purpose, mentors, and the biggest mistake
    35:40 This week's book and where to find Gino

    This week's book: The Psychology of Money by Morgan Housel

    https://www.amazon.com/Psychology-Money-Timeless-lessons-happiness/dp/0857197681?tag=clarkstholdin-20

    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:

    • Clark St Capital -> Passive real estate investments for busy business owners and executives
    • Elevista -> AI SaaS for real estate investors
    • Clark St Academy on YouTube -> Learn how to invest in real estate

    Social Media:

    • LinkedIn -> Ed Mathews (President at Clark St and Elevista)

    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!

    40 min
  • 3,000 Flips, Zero Tech Background: How Robbie Crager Uses AI to Scale

    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

    00:00 The leap of faith: no money, bad credit, no clue
    00:59 Welcome to Real Estate Underground
    02:14 28 years, thousands of houses, and Puerto Rico zombie homes
    03:33 You don't have to stay in a broken system
    04:07 Quitting at 25 and the Carlton Sheets first deal
    06:40 Scaling to a couple of houses a week for 20 years
    08:47 Using AI every day in a lean flipping business
    10:32 The markets: Florida, the online shift, and Puerto Rico
    11:23 The three-question filter for entering a new market
    13:12 Investing with impact and the Ukraine orphanage house
    17:44 Working with his son McKenna in the business
    21:31 The deal you don't do: the joy of missing out
    23:43 Purpose, legacy, and what gets him out of bed
    26:11 The free FlipFlop Flipper community
    26:46 The biggest mistake: flipping everything, keeping nothing
    29:30 Lightning round: books, success, and travel
    32:47 Where to find Robbie

    This week's book: Think and Grow Rich by Napoleon Hill

    https://www.amazon.com/Think-Grow-Rich-Publication-Foundation/dp/193787950X?tag=clarkstholdin-20

    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:

    • Clark St Capital -> Passive real estate investments for busy business owners and executives
    • Elevista -> AI SaaS for real estate investors
    • Clark St Academy on YouTube -> Learn how to invest in real estate

    Social Media:

    • LinkedIn -> Ed Mathews (President at Clark St and Elevista)

    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!

    35 min
  • Detroit's Comeback: Turnkey Cash Flow in America's Most Undervalued Market

    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:

    • Clark St Capital -> Passive real estate investments for busy business owners and executives
    • Elevista -> AI SaaS for real estate investors
    • Clark St Academy on YouTube -> Learn how to invest in real estate

    Social Media:

    • LinkedIn -> Ed Mathews (President at Clark St and Elevista)

    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!

    45 min
  • Tom Dunkel's SAFE Method: Vetting Every Deal Before You Invest

    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

    00:00 Don't let the tax tail wag the freedom dog
    01:00 Meet Tom Dunkel and Eagle Capital Investments
    03:00 Why true diversification lives outside the stock market
    04:00 The SAFE Investing Method: Sponsor, Asset, Financials, Exit
    08:00 Taxes and the lazy man's 1031 exchange
    13:00 The Wealth Builder's Playbook and being the "who"
    17:00 The buy box: mobile home parks, co-living, multifamily
    22:00 Where self-storage sits after the boom
    24:00 Using Claude and Manus to move faster
    27:00 Lightning round: purpose, significance, and legacy
    30:00 The best advice he ever got
    33:00 A decision he would take back
    34:00 On the nightstand: Invest Like a Billionaire
    36:00 Defining success as an empty nester
    38:00 Golf, a rock and roll cover band, and where to find Tom

    This week's book: Invest Like a Billionaire: Unlocking the Wealth Secrets of the Ultra-Rich by Bob Fraser and Ben Fraser

    https://www.amazon.com/dp/B0F3W2SNDS?tag=clarkstholdin-20

    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:

    • Clark St Capital -> Passive real estate investments for busy business owners and executives
    • Elevista -> AI SaaS for real estate investors
    • Clark St Academy on YouTube -> Learn how to invest in real estate

    Social Media:

    • LinkedIn -> Ed Mathews (President at Clark St and Elevista)

    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!

    41 min
  • B-Class Property, A-Class Management: The Short-Term Rental Edge with Tim Hubbard

    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:

    • Why the “can’t be hands-on AND remote” constraint is the forcing function that built Corzly—and what it means for any operator stuck in their own business
    • The buy box: how Tim underwrites a short-term rental like an apartment building, what data sources actually matter, and the regulatory gotchas that kill deals
    • Why urban short-term rentals quietly outperform vacation markets—more reasons to stay, less seasonal volatility, and the medical-professional and conference angles most investors miss
    • The lightning round: under-budgeting renovations, Dennis Waitley’s “two choices” framing, and why education became Tim’s purpose once the portfolio could run itself
    • Books Tim recommended:

      • Who Not How by Dan Sullivan and Dr. Benjamin Hardy—the framework for finding the right people to delegate to
      • The Slight Edge by Jeff Olson—Tim’s most-recommended book; the case for compounding small daily disciplines
      • 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.

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        🎧 Subscribe to Real Estate Underground for weekly insights on building wealth through real estate, without sacrificing your sanity.

        Additional Resources:

        • Clark St Capital -> Passive real estate investments for busy business owners and executives
        • Elevista -> AI SaaS for real estate investors
        • Clark St Academy on YouTube -> Learn how to invest in real estate

        Social Media:

        • LinkedIn -> Ed Mathews (President at Clark St and Elevista)

        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!

        29 min
      • From X Games Gold to 3,300 Multifamily Units with Dan Brisse

        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:

        • The chairlift moment that reframed every financial decision Dan has made since
        • Why 78% of pro athletes are broke within three years of retirement and the side-hustle move he made to avoid joining them
        • The Cleburne, Texas case study: $6.75M acquisition, $2.1M LP raise, full-cycle returns
        • A second case study where interior upgrades and water conservation drove a 1.8x equity multiple in two years
        • Why Dan believes we are in a generational buying window with multifamily trading at 30-40% discounts versus 2021-22 peaks
        • His sharpest definition of wealth, and why "rich" and "wealthy" aren't the same thing

        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:

        • Clark St Capital -> Passive real estate investments for busy business owners and executives
        • Elevista -> AI SaaS for real estate investors
        • Clark St Academy on YouTube -> Learn how to invest in real estate

        Social Media:

        • LinkedIn -> Ed Mathews (President at Clark St and Elevista)

        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!

        43 min
      • Real Estate Hustle vs. Real Estate Business with JB Thibodeaux

        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:

        • Pocket development inside a major metro: the framework
        • The duplex math that vindicated a Houston long-hold
        • Houston's "no zoning" reality: where the leverage actually lives
        • Why "the gurus teach you doors, not business"
        • House hacking as the duplex exit strategy
        • Generational construction knowledge as competitive moat
        • Mayor Sylvester Turner naming February 20 "James 'JB' Thibodeaux Day" (2019)

        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:

        • Clark St Capital -> Passive real estate investments for busy business owners and executives
        • Elevista -> AI SaaS for real estate investors
        • Clark St Academy on YouTube -> Learn how to invest in real estate

        Social Media:

        • LinkedIn -> Ed Mathews (President at Clark St and Elevista)

        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!

        43 min

      About Real Estate Underground

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      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,…