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  • $30,000 a Door: Dr. Alex Cartwright Brings Dead Hotels Back to Life

    $30,000 a Door: Dr. Alex Cartwright Brings Dead Hotels Back to Life
    2026/09/01
    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 answer is yes, the multifamily price is dramatically higher than the hotel price, and the conversion unlocks the difference. The Denver project makes it concrete. A 310-room Holiday Inn sat next to Stapleton Airport until Denver built a new airport further out and the demand driver moved. Eleven stories, an atrium lobby, a balcony on every room, three underground racquetball courts. Nobody is building that again in a neighborhood of three and four story garden style apartments. Alex bought it a little under $30,000 a door and is spending $40,000 to $45,000 a unit to convert it, against comparable apartments in the mid to upper $200s. In this episode: What an end-of-life hotel is, and the three things that decide whether he enters a market at allWhy a hotel is already most of an apartment building: individual bathrooms, HVAC, front doors, parking, soundproofingWhich rooms get combined, and why going all studios pencils best but still is not the answerWhy the due diligence period runs several months instead of weeks, and why sellers grant itThe Denver numbers: under $30,000 a door in, $40,000 to $45,000 a unit of renovation, roughly $90 a door all inWhy an extended stay hotel converts for $10,000 to $15,000 a room insteadHow lenders underwrite the deal off stabilized value, the same way they underwrite a flip off ARVWhat cities are actually afraid of when you ask for the rezone, and the conversation that gets them to yesThe rent-burden math: more than half of rent-burdened Americans earn $45,000 to $75,000 a yearCutting a resident's housing cost by 35 to 40% without a dollar of taxpayer money Plus the Final Five, a poem called The Man in the Glass, and why you should always be looking for your next mentor. About Dr. Alex Cartwright Dr. Alex Cartwright is the founder of HotelSHIFT Capital, based in Providence, Rhode Island, which acquires end-of-life hotels and converts them to multifamily housing. He spent ten years as an economics professor before moving to the operating side. Connect with Alex: hotelshift.capital. He writes the mailing list himself. This week's book: How Elon Musk Thinks. He also recommended the economics blog Marginal Revolution and the All-In podcast. Chapters 00:00 The rent-burdened middle: $45k to $75k a year 00:35 Welcome to Real Estate Underground 01:21 On location in Rhode Island 01:37 Meet Dr. Alex Cartwright of HotelSHIFT Capital 02:02 We are not in the hotel business 02:23 What an end-of-life hotel is 02:46 The arbitrage: hotel price versus multifamily price 03:04 Fundamentally we're in the apartment business 03:20 The buy box, part one: rent level 04:20 Part two: density and smaller units people accept 04:55 Part three: the regulatory environment 05:15 Why a hotel is already most of an apartment building 06:01 Floor plans: what gets combined and what does not 06:56 Why all studios pencils best and still isn't the answer 08:02 Ed on churn and sticky tenants at the best price in the market 09:05 Sponsor break 10:01 Vertical management or third party 10:41 Hold period, and where Opportunity Zones fit 11:08 The 24 to 36 month renovate-and-lease-up plan 11:18 Refinance and return roughly 100% of capital 12:00 Why due diligence runs months instead of weeks 12:43 The Denver deal: a 310-room Holiday Inn 13:27 Why hotels break down above 200 rooms 13:38 The airport that closed and took the demand with it 14:13 Bought a little under $30,000 a door 14:29 Six months of due diligence and Denver's energy codes 14:48 Adaptive reuse and why the architect comes in early 15:24 Construction cost: the more vertical, the more expensive 15:52 Eleven stories, an atrium, a balcony on every room 16:25 $40,000 to $45,000 a unit, and what that buys 16:44 Putting a kitchen in every room 17:08 An 18-month budget they expect to beat 17:27 Extended stay hotels convert for $10,000 to $15,000 a room 18:39 About $90 a door all in against low $200s 19:37 A-class amenities at a B-plus rent 20:16 How he finds these projects, and why there are more than he can buy 20:39 Why multifamily always deserves a remodel and hotels do not 21:21 The flag treadmill: a new brand every few years 22:24 Fewer hotel buyers, fewer hotel lenders, better deals 23:00 What changed after COVID 23:39 How lenders underwrite it, the same way they underwrite ARV 24:13 Rezoned before closing, so it's multifamily that needs work 24:35 What cities are actually afraid of 25:07 Not capital-A affordable housing 25:44 Who really lives in a $50 a night hotel 26:...
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    46 分
  • The Free Fortune 500 Playbook: Alex Lopez, CPA on Fractional CFOs and the 10-K Nobody Reads

    The Free Fortune 500 Playbook: Alex Lopez, CPA on Fractional CFOs and the 10-K Nobody Reads
    2026/08/25
    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 lost the properties he had bought. Going back to finish his business degree, he hit the two accounting courses every Florida business major has to take, and found that the numbers were a language that explained his own mistakes better than the market crash did. He switched his major, went straight into a global firm, asked to be put on the real estate clients, and drew a $4 billion hotel REIT as his first account. Corporate came next, then helping take a company public, then his own shop.The thing he brought back is the spine of this conversation. The most powerful things those firms do are perfectly doable at any size. It comes down to structure, skill and prioritization, and to somebody actually being assigned the work.In this episode:What a fractional CFO actually does that a bookkeeper does notWhy you should run your company as though it were already much largerThe windshield versus the rear-view mirror, and why most accounting only looks backwardKPIs and plans: NOI, rent per square foot, CAM, occupancy, and how to pick yoursReverse-engineering a business plan into a debt and equity structureThe free playbook hiding in plain sight: the 10-K filings public companies in your field are legally required to publish, KPIs includedWhy the skill set changes completely at every revenue tierPlus the Final Five, a mentor named Anatoly, and the one mistake Alex committed to never making again.About Alex Lopez, CPA Alex Lopez, CPA is the Managing Partner of Osher CPAs, a South Florida firm providing accounting, CFO services, financial due diligence, and tax strategy to real estate investors, property managers, and growing businesses. He works primarily with owners in the low seven-figure to mid eight-figure range.Connect with Alex: alexlopezcpa.comThis week's book: Get Scalable: The Operating System Your Business Needs To Run and Scale Without You by Ryan DeissChapters00:00 The big-firm playbook is available to the rest of us 00:45 Welcome to Real Estate Underground 01:40 Meet Alex Lopez, CPA 02:00 Growing up in the South Florida boom 02:45 The 2008 crash, and losing everything in his early twenties 04:45 Stumbling into accounting: the language of business 05:50 Why the global firms only hire you straight out of school 06:30 Canvassing commercial property the old-fashioned way 08:15 Asking to be put on the real estate clients 08:45 First client: a $4 billion hotel REIT 09:30 Into the corporate world, then taking a company public 11:00 Opening his own shop 11:35 What a fractional CFO actually is 12:30 More than a decade inside: it is structure, skill and prioritization 13:30 Think of yourself as a much larger company 14:30 The windshield, not the rear-view mirror 16:00 KPIs and plans: where a CFO starts 17:00 Reverse-engineering the plan into financials 17:50 The metrics that matter: NOI, rent per square foot, CAM, occupancy 20:00 Debt versus equity, and what you actually need to raise 21:20 Your neighbor's daughter who does the bookkeeping 21:50 The skill set changes at every revenue tier 22:45 The free playbook: read the 10-Ks of public companies in your field 24:45 They share their playbook because legally they have to 25:00 Ed's story: running a $1M company like a $100M company 27:00 You miss 100% of the targets you don't set 28:50 The Final Five 29:00 Purpose: the high-rises of Medellin 29:45 Best advice: intentional hats, from a mentor named Anatoly 30:40 The mistake: selling property 33:50 Nobody regrets holding a property too long 35:40 This week's book: Get Scalable by Ryan Deiss 37:00 The E-Myth, Buy Back Your Time, and who he serves 39:30 How he defines success 40:20 Where to find AlexReal Estate Underground Hosted by Ed Mathews of Clark St Capital. New episodes every Tuesday. clarkst.com/podcastElevista - 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 executivesElevista -> AI SaaS for real estate investorsClark St Academy on YouTube -> Learn how to invest in real estateSocial 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. ...
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    42 分
  • Investors Don't Invest in Deals: Shams Merchant on ChatGPT, the 506(c) Default and What LPs Actually Check

    Investors Don't Invest in Deals: Shams Merchant on ChatGPT, the 506(c) Default and What LPs Actually Check
    2026/08/18

    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 model has no access to which structures have actually been tested and litigated with the SEC, and no discretion about what belongs in a document and what does not. You are not paying for a stack of paper. You are paying for someone whose malpractice insurance stands behind the decision.

    On what LPs check: they can spot AI-drafted documents immediately. They ask who your law firm and your CPA are, because they want to know who is backing you. They do not want a five-hurdle waterfall nobody can follow. They do not want seven stacked fees. They want clawbacks, so a disposition fee disappears if the deal misses its return metrics. And they want a GP contribution that is real cash out of your pocket, not an acquisition fee recycled back into the deal and called skin in the game.

    On 506(b) versus 506(c): Shams defaults to C for nearly everyone. B only makes sense on a small raise, or when you have spent a decade building an investor base deep enough to fill the round from existing relationships. His words: you only know so many human beings.

    The last stretch is the one that will stay with you. Shams thinks there will be meaningfully fewer lawyers within a few years, that one attorney with good tooling can run a two-hundred-million-dollar deal, and that AI already redlines a standard contract better than a first-year associate. Ed pushes on the obvious problem. If nobody hires juniors, where do the seniors come from?

    Books mentioned this week
    The Price of Tomorrow by Jeff Booth
    https://www.amazon.com/Price-Tomorrow-Deflation-Abundant-Future/dp/1999257421?tag=clarkstholdin-20

    The Eight Secrets to Powerful Manifesting by Mandy Morris
    https://www.amazon.com/8-Secrets-to-Powerful-Manifesting/dp/1401969550?tag=clarkstholdin-20

    Connect with Shams Merchant
    Commercial Real Estate Law Group (CRE Lawyer) at MW Law, with offices in Dallas, Houston, and Fort Worth and a national practice.
    Website: cre.law
    LinkedIn: linkedin.com/in/shams-merchant
    As he says at the close: Google "Shams Merchant," it is all public.

    Connect with Ed Mathews
    Website: clarkst.com
    Real Estate Underground is where operators talk about what is actually working. No sales pitches allowed.

    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!
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    44 分
  • Shouting Into the Void: Rob Bergeron on Unsolicited LOIs, Uniting Wholesalers, and the Good Neighbor Data Center

    Shouting Into the Void: Rob Bergeron on Unsolicited LOIs, Uniting Wholesalers, and the Good Neighbor Data Center
    2026/08/11
    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 calls himself the tilapia of realtors. He owns Winner Realty in Louisville, runs OffMarket.deals nationally, writes The Morning Bergeron five days a week, and is building what he hopes becomes the institutional standard for data centers. On paper that is four unrelated businesses. In practice it is one move, repeated. The wholesalers in Louisville were all convinced they were competing for the same buyers. Rob ran comps for them for years and never once took a deal off them. When he finally asked for their buyer lists, they handed them over. He merged those lists with his own, charged two thousand dollars only when he brought the buyer, and made forty two thousand in year one. That business is now OffMarket.deals. He posted on the BiggerPockets subreddit because nobody else was posting there. That produced David Greene. He sent one newsletter into the void about data and energy. That produced a partner, a connection to HKS, and a design that shrinks data center footprints by 92 percent, runs closed loop on 40 gallons of water a year, uses submerged cooling so it makes no noise, and routes its waste heat to farms. And he sends unsolicited letters of intent to listed properties and for-sale-by-owners on behalf of his clients' buy boxes. Direct mail hits at 1.1 percent and costs money. Rob hits at 2.1 percent and spends nothing. His frame for all of it: we are in the NIL era of real estate, where everyone has to earn everyone's business. Nobody is owed a repeat client. Rob also gives one percent of Winner Realty's net profits to Hand in Hand, which builds houses in Belize for about ten thousand dollars each. His stated legacy goal is one house every month, forever. Find Rob: The Morning Bergeron newsletter, and OffMarket.deals for assignable contracts and the buyers list. This week's book: The Power of Moments by Chip Heath and Dan Heath https://www.amazon.com/dp/1501147765?tag=clarkstholdin-20 Chapters 00:00 The NIL era of real estate 00:33 Welcome to Real Estate Underground 01:45 Meet Rob Bergeron, the tilapia of realtors 03:00 Why investor clients are worth the reputation they have 03:30 Louisville: slow to rise, slow to fall 05:00 Where Rob is looking now: energy, water, land, agriculture 06:00 Bloom Energy, small modular nuclear, and a Q1 2027 timeline 07:00 Three Mile Island, and the cousin who built the cleanup robots 08:15 One Saturday email into the void 09:30 The Louisville Network becomes OffMarket.deals 10:45 Uniting the tribes: competing wholesalers, one buyers list 11:00 HKS, SoFi Stadium, and a data center division three months old 12:00 Shrinking the footprint by 92% 12:45 The good neighbor data center 13:45 Why retrofits beat new builds 14:15 Waste heat, farmers, and who is actually getting squeezed 15:45 Let the average person own the residuals, not BlackRock 16:30 Shooting your shot 16:45 How posting on a subreddit produced David Greene 18:00 Louisville as a real estate brain trust 19:00 What the next three years look like 20:30 3D printing, automation, and what is actually viable 21:15 The unsolicited LOI play: 2.1% hit rate, no money spent 22:45 The NIL era: everyone earns everyone's business 23:30 Winner Realty and giving agents more than one trick 23:45 Rob's Brain 24:15 Winner Services: lending, oil and gas, water treatment, data center land 25:15 Three or four things a day 25:45 Hand in Hand, and the house that changed the math 26:45 Two grand versus $1,900 a year 27:00 One house a month, forever 28:15 The Power of Moments 29:30 Water balloons, a record, and sending Panera anonymously 30:00 Why wholesaling is the lowest barrier in the business 31:30 The deal he would take back: a partner with no money in it 32:45 What he should have built on the front end 33:30 Less chips, more steak: how Rob reads 35:00 The highlights someone finds after he is gone 35:30 How Rob defines success 36:15 An ADD brain, AI, and making it linear 38:00 Obsidian, and Ed's own workaround 39:15 Music, sun, and saying weird things in public 40:00 Where to find Rob 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 executivesElevista -> AI SaaS for real estate investorsClark St Academy on YouTube -> Learn how to invest ...
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    42 分
  • Over-Documented, Under-Underwritten: Will Harvey Rebuilds Hard Money From First Principles

    Over-Documented, Under-Underwritten: Will Harvey Rebuilds Hard Money From First Principles
    2026/08/04
    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 that owning property is not passive. As Will puts it, the only genuinely passive position in real estate is limited partner, and you pay for it by giving up control.So he kept moving. He left a high-paying W2 to flip houses, rolled the flip profits into syndications, took bonus depreciation against the gains, did a couple of deals as a GP. And somewhere in there he figured out what actually excites him is the finance side of the table, not the operating side.That led to a friends-and-family fund in 2023, an accidental first hard money loan, and eventually a dedicated 506(c) fund built on a specific idea: that hard money underwriting is due for a rebuild from first principles.Will walks through the seven risks he underwrites against, why he thinks most lenders collect the wrong paperwork while skipping the single most predictive input available, and how he uses AI to compress an underwriting file from hours to about ten minutes without giving up the verification step.He also talks about the $70,000 he lost on a deal he already knew he should not have taken, what he looks for in an investor conversation before he will accept a wire, and why the boring end of real estate is the point rather than the compromise.What you will learnWhy Will chose debt over equity, and what that decision has to do with temperament rather than returnsThe first-principles exercise he ran on lending, and the seven risks it producedWhich document lenders over-collect, and which input they skip entirelyHow AI actually sits in his underwriting stack, and where he still verifies by handWhat he screens for in a first conversation with a prospective investorWhy he charges points and has no prepayment penaltyConnect with Will HarveyWebsite: harvey-capital.comEmail: will@harvey-capital.comLinkedIn: search Will Harvey, Harvey CapitalThis week's bookTitan: The Life of John D. Rockefeller, Sr. by Ron ChernowWill also mentioned The Book of Elon, a compilation of Elon Musk's own thinking pulled from interviews. He reads both the same way: printed out, at night, when his mind has slowed down enough to actually absorb it.Chapters00:00 Cold open: the first call with a borrower00:35 Welcome01:40 Who Will Harvey is and what Harvey Capital does02:27 Dropping out, double hip surgery, and the mortgage desk03:43 House hacking the first deal before he knew the term04:44 Nothing about owning rentals is passive05:29 Leaving a high-paid W2 to flip houses06:31 The realization: he is not an operator, he is a finance guy06:58 The 2023 friends-and-family fund07:50 The accidental first hard money loan08:06 Graduating from a 506(b) to a 506(c)10:02 Why debt instead of equity13:13 How he protects capital13:32 Applying SpaceX first principles to lending15:53 The seven risks he underwrites against16:25 Over-documenting what does not matter17:00 The borrower's story as the real underwriting input18:49 A word from Elevista Connect19:52 Screening investors on temperament, not just accreditation20:04 Why the one-year term filters people out21:00 Boring is the whole point23:20 Where the borrowers actually come from23:30 Google ads, and turning them off24:15 The REIA coin flip28:39 How Will uses AI to run the business28:44 Claude Code on the terminal30:40 Recording borrower calls as a data point31:52 Compressing hours of underwriting into ten minutes32:36 Incumbent lenders move like turtles33:01 Why flippers actually buy speed35:09 No prepayment penalties, and the reason why36:23 Lightning round36:52 What drives him37:50 The best advice he ever got38:25 Buffett: price and value are two different things39:40 The decision he would take back40:44 Losing $70,000 on a deal outside the buy box41:32 The return on brain damage41:52 What is on his nightstand41:58 Titan, and The Book of Elon43:33 Ed's NotebookLM workflow for books he never gets to45:55 How Will defines success46:12 Outcomes are a distraction, focus on the process47:50 You only get 18 summers48:56 How to reach Will49:03 harvey-capital.comThis has been the Real Estate Underground. Don't forget to subscribe, it helps us grow.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 executivesElevista -> AI SaaS for real estate ...
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    50 分
  • "How Do I Lose Money on This Deal?" Vessi Kapoulian's Lender-First Underwriting

    "How Do I Lose Money on This Deal?" Vessi Kapoulian's Lender-First Underwriting
    2026/07/28
    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 LinkedInChapters 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 UnderwritingThis 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/podcastElevista - 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 executivesElevista -> AI SaaS for real estate investorsClark St Academy on YouTube -> Learn how to invest in real estateSocial 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!
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    40 分
  • You Don't Find a Deal, You Make a Deal: Dr. Jordan Romano's Zoning Playbook

    You Don't Find a Deal, You Make a Deal: Dr. Jordan Romano's Zoning Playbook
    2026/07/21
    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 executivesElevista -> AI SaaS for real estate investorsClark St Academy on YouTube -> Learn how to invest in real estateSocial 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!
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    46 分
  • Debt Is Gambling: The Zero-Debt Playbook with Joel Friedland

    Debt Is Gambling: The Zero-Debt Playbook with Joel Friedland
    2026/07/14

    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!
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    53 分