Real Estate Underground

Ed Mathews
  • 4.8 (18)
  • Investing
  • Updated Weekly

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 inHow to vet opportunities when everyone else is sitting on the sidelinesConservative underwriting in markets that punish optimismSystems 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.

  1. 12h ago

    The inspector told Jeff Emalaba to run. Confirmation bias cost Jeff $11,000.

    Twenty-five years ago Jeff Emalaba was a guest host on CNBC Africa, analyzing derivatives, commodities and futures, and holding an options license in Florida. He describes all of it as one subject: risk transference. That is the lens he brought to real estate, which makes what happened next harder to explain and more useful to hear. He drove two hours to see a duplex in North Carolina and walked it with his agent. Nothing looked wrong. He asked the seller why the previous buyer had backed out and was told they could not get funding. He asked his agent to dig further. Nothing came back. So he paid. Five thousand dollars in non-refundable due diligence fees, five thousand in earnest money, six hundred seventy-five for an inspection, seven hundred for an appraisal. That money was committed before anyone had been inside the walls. Then the inspector came back with one word: run. Foundation, structural, roofing, mold, electrical. Jeff didn't believe him. He decided the inspector was exaggerating and hired a general contractor to go prove it, fully intending to pay that contractor to fix whatever turned out to be wrong. The contractor sent back a ten-page email explaining why he should never buy the property unless he had a hundred thousand dollars to spend. Jeff walked. The seller kept the money. The part Jeff wants investors to understand is how all of that was legal. A seller who already knows about a prior buyer's inspection report can select no representation on the disclosure form, stay silent, and keep the fees when the deal dies. He calls it the no representation loophole, and it is what sent him to build InvestFusion. Ed presses him on the part that matters to anyone evaluating a tool like this: where does the data actually come from, and what happens in the middle when you ingest three inconsistent sources and output one confident answer. Ed asks as an operator who runs his own deals through AI, not as a host taking a pitch. Also in this episode: why Ed thinks a Zestimate is not merely inaccurate but dangerous, what a single government tenant can do to a commercial deal, the four fees an investor can lose before owning anything, Manny Khoshbin's "you make your money on the buy," and Ed's own translation of the word pro forma. Questions from the Underground is back at 26:38. Jack, an investor in North Carolina, analyzed sixty deals in three months and made zero offers because nothing penciled. He wants to know whether the market is broken or he is. Ed's answer: sixty analyzed and zero offered is not caution, and there is a three-step sort that tells you which of your buy box, your cost of capital, or your read on the market is actually wrong. Connect with Jeff Emalaba InvestFusion: investfusion.coLinkedIn: linkedin.com/in/jeff-emalabaJeff made a page just for this show, with his deal-killing red flag cheat sheet and his 60-second vetting blueprint: underground.investfusion.coOn the nightstand Jeff's go-to, read many times over: Goals! by Brian Tracy 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!

  2. Sep 8

    Mark Khuri reviews up to 700 deals a year. He invests in 10. Here's his filter.

    Mark Khuri co-founded SMK Capital Management with his father, Dr. Suheil Khuri, pooling family capital informally before opening the firm's doors in 2010. They operated properties directly through 2017, then pivoted entirely to the LP side. Today SMK reviews 600 to 700 private real estate deals a year and invests in roughly 1 to 2% of them, call it 5 to 10 deals annually, across diversified funds, single-asset deals, and one-off syndications for their investor base. Ed and Mark get into the mechanics of how SMK actually filters that flow: a 40-point due diligence checklist covering firm credentials, deal-level underwriting, and required deliverables, the discipline of comparing an operator's underwritten returns against their actual results on deals that already went full cycle, and the red flags that end a conversation before it starts (a principal who won't share their last name is an automatic no). From there, the conversation turns to mobile home parks, an asset class SMK has been investing in since 2012. Mark explains why new supply is structurally constrained (NIMBYism, unaffordable construction economics), why 70 to 80% of parks are still owned by mom-and-pop operators with no succession plan, and the specific value-add levers SMK targets: occupancy infill and converting park-owned homes into tenant-owned homes through rent-to-own financing structures. He's candid about where the asset class has gotten more competitive, cap rates in some markets have compressed from north of 10% a decade ago to 3 to 4% today, and why SMK stays out of the priciest infill deals and the most distressed ones alike. The episode closes on underwriting discipline: the hardest deal Mark walked away from recently, and why "pro forma" so often needs a second, much more skeptical read. Also in this episode: the first installment of Questions from the Underground, where Ed answers a real problem an investor put to him: a contractor took most of the draws, the job is 40% done, and the contractor has gone dark. What to do first, on tape, no filler. Real Estate Underground publishes every Tuesday. Chapters 0:00:00 Cold open: "We like to see underwritten returns versus reality" 0:00:40 Real Estate Underground intro 0:02:03 Welcome Mark Khuri, SMK Capital Management 0:03:32 From property operator to fund-of-funds: the 2017 pivot 0:05:06 Going for the no: SMK's first filter on any deal 0:07:23 The 40-point sponsor due diligence checklist 0:09:02 Red flags: the people behind the deal 0:11:21 The exit-strategy question that reveals alignment 0:12:33 Why mobile home parks: the supply story 0:14:44 Ownership is still mom-and-pop: the value-add opportunity 0:16:28 Converting park-owned homes to tenant-owned 0:19:30 Still a darling, or getting crowded? Cap rate compression 0:21:28 Where SMK's deals actually come from 0:21:50 Questions from the Underground: the contractor who took the draws and vanished 0:26:49 The hardest deal Mark walked away from 0:27:57 "Pro forma is Latin for full of shite" 0:29:58 Cashflow gets you through the downturns 0:30:51 Final five: purpose, mentors, and the "show them 15" lesson 0:36:32 Who Mark reads: Jay Parsons, Marcus & Millichap, Richard Duncan 0:37:13 Defining success, life in Bend, Oregon, and how to find SMK Connect with Mark Khuri: smkcap.com linkedin.com/in/mark-khuri-7543821 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!

  3. Sep 1

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

    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 all Why a hotel is already most of an apartment building: individual bathrooms, HVAC, front doors, parking, soundproofing Which rooms get combined, and why going all studios pencils best but still is not the answer Why the due diligence period runs several months instead of weeks, and why sellers grant it The Denver numbers: under $30,000 a door in, $40,000 to $45,000 a unit of renovation, roughly $90 a door all in Why an extended stay hotel converts for $10,000 to $15,000 a room instead How lenders underwrite the deal off stabilized value, the same way they underwrite a flip off ARV What cities are actually afraid of when you ask for the rezone, and the conversation that gets them to yes The rent-burden math: more than half of rent-burdened Americans earn $45,000 to $75,000 a year Cutting 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 26:30 The conversation that gets a city to yes 27:34 The Final Five 27:46 Purpose: ten years teaching economics, and what changed 29:27 What rent burdened means 30:07 More than half earn $45,000 to $75,000 31:32 Cutting a resident's rent by 35 to 40% with no taxpayer money 32:32 Best advice: always be looking for your next mentor 33:57 Ed on Mike Godman and the 19 ways he was screwing up 36:24 The decision he wants back: firing too slowly 37:53 Why the person you fire is often relieved 38:47 The bookshelf, and what he's reading now 39:21 How Elon Musk Thinks 40:38 Marginal Revolution and the All-In podcast 41:01 How he defines success 41:55 The Man in the Glass 42:28 Cars, and the Harvard Classics 44:42 Where to find Alex 45:32 Outro Real Estate Underground Hosted by Ed Mathews of Clark St Capital. New episodes every Tuesday. clarkst.com/podcast Elevista - Speed as a Service™ Elevista Connect is the first AI-powered lead conversion system built for real estate investors. 🎧 Subscribe to Real Estate Underground for weekly insights on building wealth through real estate, without sacrificing your sanity. Additional Resources: 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!

  4. Aug 25

    The Free Fortune 500 Playbook: Alex Lopez, CPA on Fractional CFOs and the 10-K Nobody Reads

    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.com This week's book: Get Scalable: The Operating System Your Business Needs To Run and Scale Without You by Ryan Deiss Chapters 00:00 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 Alex Real Estate Underground Hosted by Ed Mathews of Clark St Capital. New episodes every Tuesday. clarkst.com/podcast Elevista - Speed as a Service™ Elevista Connect is the first AI-powered lead conversion system built for real estate investors. 🎧 Subscribe to Real Estate Underground for weekly insights on building wealth through real estate, without sacrificing your sanity. Additional Resources: 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!

  5. Aug 18

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

    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 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!

  6. Aug 11

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

    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 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!

  7. Aug 4

    Over-Documented, Under-Underwritten: Will Harvey Rebuilds Hard Money From First Principles

    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 learn Why 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 penalty Connect with Will Harvey Website: harvey-capital.com Email: will@harvey-capital.com LinkedIn: search Will Harvey, Harvey Capital This week's book Titan: The Life of John D. Rockefeller, Sr. by Ron Chernow Will 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. Chapters 00:00 Cold open: the first call with a borrower 00:35 Welcome 01:40 Who Will Harvey is and what Harvey Capital does 02:27 Dropping out, double hip surgery, and the mortgage desk 03:43 House hacking the first deal before he knew the term 04:44 Nothing about owning rentals is passive 05:29 Leaving a high-paid W2 to flip houses 06:31 The realization: he is not an operator, he is a finance guy 06:58 The 2023 friends-and-family fund 07:50 The accidental first hard money loan 08:06 Graduating from a 506(b) to a 506(c) 10:02 Why debt instead of equity 13:13 How he protects capital 13:32 Applying SpaceX first principles to lending 15:53 The seven risks he underwrites against 16:25 Over-documenting what does not matter 17:00 The borrower's story as the real underwriting input 18:49 A word from Elevista Connect 19:52 Screening investors on temperament, not just accreditation 20:04 Why the one-year term filters people out 21:00 Boring is the whole point 23:20 Where the borrowers actually come from 23:30 Google ads, and turning them off 24:15 The REIA coin flip 28:39 How Will uses AI to run the business 28:44 Claude Code on the terminal 30:40 Recording borrower calls as a data point 31:52 Compressing hours of underwriting into ten minutes 32:36 Incumbent lenders move like turtles 33:01 Why flippers actually buy speed 35:09 No prepayment penalties, and the reason why 36:23 Lightning round 36:52 What drives him 37:50 The best advice he ever got 38:25 Buffett: price and value are two different things 39:40 The decision he would take back 40:44 Losing $70,000 on a deal outside the buy box 41:32 The return on brain damage 41:52 What is on his nightstand 41:58 Titan, and The Book of Elon 43:33 Ed's NotebookLM workflow for books he never gets to 45:55 How Will defines success 46:12 Outcomes are a distraction, focus on the process 47:50 You only get 18 summers 48:56 How to reach Will 49:03 harvey-capital.com This 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 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!

  8. Jul 28

    "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 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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4.8
out of 5
18 Ratings

About

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 inHow to vet opportunities when everyone else is sitting on the sidelinesConservative underwriting in markets that punish optimismSystems 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.

Information

  • Creator
    Ed Mathews
  • Years Active
    2018 - 2026
  • Episodes
    219
  • Rating
    Clean
  • Copyright
    © 2026 Clark St Holdings LLC
  • Show Website
    Real Estate Underground

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