Real Estate Underground copertina

Real Estate Underground

Real Estate Underground

Di: Ed Mathews
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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, all while traveling 150+ nights a year working for some of Silicon Valley's top companies. 100+ deals later, he shares what actually works and what doesn't.


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)

  • What we learned when contractors ghosted and we had to step in
  • How to vet opportunities when everyone else is sitting on the sidelines
  • Conservative underwriting in markets that punish optimism
  • Systems that protect capital when deals go sideways


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.

© 2026 Clark St Holdings LLC Economia Finanza personale Gestione e leadership Leadership Marketing Marketing e vendite
Episodi
  • Over-Documented, Under-Underwritten: Will Harvey Rebuilds Hard Money From First Principles

    Over-Documented, Under-Underwritten: Will Harvey Rebuilds Hard Money From First Principles
    Aug 4 2026
    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 min
  • "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
    Jul 28 2026
    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 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 min
  • 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
    Jul 21 2026
    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 min
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