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Nasir Ali runs Rise360 Ventures. He comes from eight generations in commercial real estate and is the second generation in manufactured housing, a business his family just marked 45 years in, through at least nine downturns. His case for the asset class is simple. "We own the land. And sure the common areas and whatnot, but essentially we're renting dirt." No plumbing, no electrical, no toilets for every unit. "I don't own the damn door." Nasir also thinks the hard part of the cycle hasn't hit yet. As credit tightens, he says, it sets the stage for more creativity, more creative financing and alternative financing. And when budgets get cut, "people drop what they don't need. You can't drop shelter." What Ed and Nasir get into: The late-1970s playbook, and why investors who couldn't adapt were left behind Commercial defaults in office and retail, and why they still hit everyone in commercial real estate through the banks Seller financing, master leases and the other options when bank lending dries up Why manufactured housing has been resilient, not just recession resistant "There's plenty of housing. The problem is it's not affordable." Affordability versus attainability Filling half-empty communities with a dealer arm, financing and turnkey three-bed, two-bath homes The get rich slow scheme: a three to five year journey from 60 or 70% occupancy to full What eight generations passed down when the money was lost: tenacity, knowledge and values The HVAC company he bought after 2008 that cratered overnight, and why you make sure you understand your domain Why his definition of success is one word Also in this episode, Questions from the Underground, from Dave in San Clemente, California: an investor rehabbed and rented a house, and the refi appraisal came in short of what he needed to pull his cash back out. Ed covers why you need to be proactive with appraisers, not reactive, the packet he gives every appraiser, why any pushback is about the comp and not the number, and why he underwrites the refi at 90 to 95% of after rehab value before he buys. Book mentioned: How to Win Friends and Influence People by Dale Carnegie, Nasir's pick Get Nasir's free manufactured housing report at rise360ventures.com, or find him on LinkedIn. Got a question you want answered on the show? Send it to [email protected]. Recorded September 2026. 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!

Forrest Jinks runs Altus Equity Group, a real estate investment company that works with family offices and high net worth investors. Most sponsors chase top-line IRR: get in, get out in two, three or four years. Forrest says that leaves a lot of meat on the bone. "It might be awesome to get an 18% return over 10 years versus a 20% return in three." He cares about the net return, after taxes, and about how much risk sits behind the number. Altus runs a lending side too, and Forrest underwrites every loan like an owner. His first question: would we love to own this in our equity business at the debt amount plus foreclosure costs? "If the answer is yes, we're gonna figure out a way to make that loan work." What Ed and Forrest get into: Why a 12% first-position loan at 30% loan to value can beat an 18% ground-up construction deal An industrial building in Mississippi bought for $12 a foot, and the Fortune 500 tenant that signed first Why Forrest calls the Altus debt fund "effectively a proxy for the 10-year Treasury" Walking the property, on equity deals and on loans No back-end leverage, and why Ed's debt fund doesn't borrow to lend either Why the biggest red flag in an investor is wanting to get rich quick Holding for 10 years or more, and why real estate's wider band lets you buy low and sell high in any part of the cycle The day Forrest decided to build a company instead of doing three or four deals a year The promise he made to investors before 2008, and why he'll never make it again His daughter's olive oil business, and why her $7,000 from him is an investment, not a gift Also in this episode, Questions from the Underground: Jose's lender approved half his draw, and his contractor says no money, no work. Ed covers why the fight is really about the definition of done, why your project schedule and your draw schedule need the exact same language, and why you carry a 10 to 20% contingency. Book mentioned: Making the Zeros Count, Forrest's pick Read the Altus Insight, Forrest's monthly article on investing and economics, at altusequity.com/insights. Got a question you want answered on the show? Send it to [email protected]. Recorded September 2026. 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!

Palmy Kitti and her sister Nan started a fashion business with $2,000. Years later their biggest client shut down all its retail stores and 95% of their income was gone overnight. They moved into flipping houses in Los Angeles, then into multifamily syndication. Seven and a half years in, Palmy says they have nearly half a billion dollars in assets under management across Georgia, Arkansas and Texas. Now a lot of that business runs through AI. After a property management changeover, her system flagged that one property had more cash than its reports showed. They'd overfunded the reserve account by $169,000. Finding that used to mean people matching rent rolls against the T12 and the general ledger by hand. She says it took her less than five minutes. She's just as clear about where AI stops. "You can have the best AI tools, but AI doesn't give you that judgment. You have to make that judgment." What Ed and Palmy get into: The $169,000 her AI caught in a reserve account after a property management changeover A fire that burned eight units with only two occupied, and the eight-page report that got the insurer to approve business interruption on all eight: $136,000 through August Her AI investment committee, with a risk role, a capital role and a market role that each try to find the flaws in a deal before a CEO role sums it up Why AI multiplies the advantage you already have and can't create one for you Ed's rule for the AI agents in his flip business: they handle execution, never judgment How a newer investor can use AI to bring real value to an experienced general partner The partner who stole her investor list, and the partners who went quiet during a refinance Why drinks on Thursday doesn't mean you get married on Saturday The investor on their dead list who invested five years later "Earn to own," and what Fortune Builders taught her about owning assets before buying things Also in this episode, Questions from the Underground: when do I quit the job? Ed covers what has to be in place before you leave your W-2: insurance, cash reserves, debt, plus structure and protection. Book mentioned: The Innovation Secrets of Steve Jobs by Carmine Gallo, Palmy's pick Learn about Palmy's AI operating system at kittiroadmap.com, and find The Kitti Sisters at thekittisisters.com and on YouTube, TikTok, Instagram and Facebook. Got a question you want answered on the show? Send it to [email protected]. Recorded September 2026. 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!

Jason Williams spent 15 years as a chemical engineer. He's owned real estate since 2003 and large multifamily since 2017. When he started underwriting apartments, half the spreadsheets he was handed had broken cells and equations that didn't work, so he built his own model. People kept asking him to show them how it worked, and that model became Ironclad Underwriting. His rule is simple: never underwrite off your own numbers. The property manager tells him what each unit can rent for. The insurance broker prices the premium off comparable properties, and he uses the high end of the range. A tax advisor fights the assessment. And the plumber's bid gets multiplied by three, sometimes four. "Every single property I've had from a 1950s build up to early 2000s has had major plumbing issues." What Ed and Jason get into: Why a T12 almost never ties to the bank statements, and when that gap is actually a red flagRent rolls that look clean but hide a rollover cliff, and why the manager, not the spreadsheet, sets pro forma rentsInsurance priced on replacement cost, and what Texas nondisclosure does to your tax bill after you buyThe tax advisor who saved him $20,000 one year and $11,000 this year, paid only on a percentage of what he savesWhy he no longer chases agency debt, even with the better ratesA 72-unit plumbing job that put residents in a hotel for two weeks, and a gas leak that shut off the gas over Easter weekendEd's sewer line on a 10-unit building that passed inspection: a $5,000 to $10,000 fix at purchase that became $44,000 a year and a half laterSix months of reserves, and why Ed doubled his after the pandemicThe zoning mistake on a mobile home community that has cost Jason more than a year of unexpected debt serviceAlso in this episode, Questions from the Underground. An experienced Connecticut investor asked Ed whether it's time to cycle back to cash flow deals or keep riding the appreciation wave. Ed's answer: it's always a cash flow play. Appreciation is the cherry on top, not the basis of a business plan. Books mentioned: Who Not How by Dan Sullivan with Dr. Benjamin Hardy, Jason's favoriteThe E-Myth Revisited by Michael E. GerberConnect with Jason Williams at ironcladunderwriting.com, or on LinkedIn. His free underwriting resources and his weekly underwriting podcast are on the site. Got a question you want answered on the show? Send it to [email protected]. Recorded September 2026. 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!

Stewart Heath, CPA went into 2008 over-levered and under-reserved. He handed buildings back to the banks. He says that for want of roughly $300,000 in reserves he would still own them, and every rule he operates by now was built backward from that number. His book is called "Don't Do What I Did." Stewart runs Harvard Grace Capital out of Spring Hill, Tennessee, buying stabilized commercial assets along the I-65 corridor from Nashville to Birmingham. Medical office, suburban office, storage, retail and warehouse. Eleven assets by the company's count and more than 300,000 square feet. Their tagline is boring is beautiful. It is printed on the banners. "There's not a whole lot boring about 13% cash on cash returns." What Ed and Stewart get into: The 12 months of mortgage reserves he sets aside on every deal, sized as if the property income goes to zero, and what holding that money costs him in returnsWhy medical office is his favorite asset class: hundreds of thousands of dollars of tenant build-out, 10 year leases, triple net with 3% bumps and tenants who treat rent as a line item instead of a negotiationSuburban office and service retail, the class B buildings where a business meets its customers rather than collects its employeesWhy he underwrites a geography and not an asset classWhy he refused to run a fund for years, and what two independent RIA relationships changedRetail moving from 25% food and restaurants to almost 60%, with price per square foot almost doubling in three yearsWhy he stopped doing single-tenant deals after watching a tenant walk out on 10 years of leaseThe contrarian office call: nobody can finance new office, the population is not shrinking and one of his buildings sits in a town under a two year sewer moratoriumAlso in this episode, a new segment called Questions from the Underground. An investor owns 19 units two states away. His manager reports 95% occupancy every month and his distributions have shrunk four quarters in a row. Ed walks through the per unit profit and loss that tells him whether he has a building problem, a manager problem or one bad quarter. Books mentioned: "Don't Do What I Did" by Stewart Heath. Free at harvardgrace.com for an email address.Who Not How by Dan Sullivan with Dr. Benjamin Hardy. Stewart is on his third read.The E-Myth Revisited by Michael E. GerberBuy Back Your Time by Dan MartellRich Dad Poor Dad by Robert Kiyosaki, the book his mentor handed himConnect with Stewart Heath at harvardgrace.com, or on LinkedIn. The free book and his calendar are both on the site, and he will talk real estate with anyone. Got a question you want answered on the show? Send it to [email protected]. Recorded June 2026. 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!

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!

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!

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!

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!

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!

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!

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: [email protected] 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!

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!

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!

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 spousesThe 2008 collapse in his own words, and the boundary he set on the other side of itThe buy box: single-tenant only, 7,000 to 30,000 square feet, no flex, no multi-tenant, and specific dock, ceiling-height and parking requirementsHow 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 dealsThe secret-sauce exit: 77 of Joel's 82 sales went to owner-occupants who pay a premium over cap-rate buyers, not to investorsA 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 itThe 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 avoidsWhy 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 casinoReshoring, tariffs, and the honest math on why manufacturing is not all coming backThe batter who never strikes outLightning 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 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!