Real Estate Underground

Ed Mathews
  • 4.8 (17)
  • 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. 5d ago

    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!

  2. 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!

  3. 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!

  4. Jul 21

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

    Most investors say there are no deals. Dr. Jordan Romano says you are looking in the wrong place. Jordan is a physician in the Boston area who has spent about a decade investing in one small New Hampshire town, the town where he did his medical residency. He is hyperlocal on purpose. He uses his own capital only. And his edge is not a list, a lead source, or a dialer. It is curiosity applied to public records, specifically planning and zoning board minutes that almost nobody reads. That is how the subdivision deal happened. A 0.9-acre parcel had been sitting on Zillow for six months, a block from a hospital, on town water and sewer, with the house pushed to one edge of the lot line. Jordan asked whether the town would allow a split, paid for a survey, presented to the planning board, and walked out with three lots where there had been one. A nurse at that hospital is going to build on one of them. The developer who owns 200 units nearby, and drove past that property roughly a thousand times a year, is buying the other. Jordan is also candid about the loss. He needed a zoning variance on a downtown building that should have been four units. A neighbor organized twenty households, the room was the fullest the board had seen in years, and Jordan walked away from the deal. Then he stayed until 11 PM to talk with everyone who had spoken against him. We also get into his B-class thesis, why he passed on a hundred units and does not regret it as much as you would think, how a busy physician finds deals in what he calls the interstitium, and the rule his grandfather gave him: always know where the exit is. Connect with Dr. Jordan Romano: medicalexpertwitness.com Chapters 00:00 Always know where the exit is 00:45 Welcome to Real Estate Underground 01:00 Meet Dr. Jordan Romano 01:20 A physician, a mother in real estate, and a house bought at the 2006 peak 03:00 Invest in what you know 04:00 Put all your eggs in one basket and watch the basket 05:00 Why hyperlocal beats long distance 06:00 Diners, broker opens, and off-market deal flow 07:30 Curiosity as a sourcing engine: planning and zoning boards 08:30 Reading the signal when a big developer expands 09:00 The 0.9-acre lot nobody else questioned 10:30 You don't find a deal, you make a deal 12:50 Ed's 58-acre farm and the land he almost missed 13:30 Zillow forensics: empty cabinets, oil heat, and a fall price cut 14:40 Finding the time: deals in the interstitium 16:20 Virtuous capitalism and the small-town ripple effect 17:30 Knocking on doors before you need the vote 18:00 The strikeout: a full room, a lost variance, a dead deal 20:00 Staying until 11 PM to talk to everyone who opposed him 23:00 The Final Five 23:20 Purpose: impact you can actually see 26:00 Best advice: his grandfather's rule 27:00 Sam Zell on markets versus deals 28:00 The one he'd take back: a hundred units passed on 29:00 The B-class thesis 30:00 Five brothers, one highway parcel, and a deal that got away 33:20 What's on the nightstand 36:50 Defining success: optionality and flexibility 39:00 Life outside real estate 42:30 Two grandfathers, two swimmers, one T-shirt 43:50 How to reach Jordan This week's book: The Almanac of Naval Ravikant by Eric Jorgenson Get it on Amazon Also mentioned: Thinking in Bets by Annie Duke, and Am I Being Too Subtle? by Sam Zell. Real Estate Underground with Ed Mathews. Find us wherever you get your podcasts, at clarkst.com/podcast or elevista.com/podcast Elevista - Speed as a Service™ Elevista Connect is the first AI-powered lead conversion system built for real estate investors. 🎧 Subscribe to Real Estate Underground for weekly insights on building wealth through real estate, without sacrificing your sanity. Additional Resources: Clark St Capital -> Passive real estate investments for busy business owners and 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. Jul 14

    Debt Is Gambling: The Zero-Debt Playbook with Joel Friedland

    Joel Friedland calls himself the most risk-averse real estate investor in the United States, and he has the scar tissue to prove it. In 2008 he was carrying $70 million in personal guarantees across 50 buildings. Ten of them were going to have to be sold at a loss. He sat his wife down and told her, and he watched her fall back in her chair. What followed was months of depression he describes without flinching in this conversation. He came out of it with a conclusion most investors never reach: the problem was not real estate, it was the way he was structuring the deals. Today Joel and his team at Brit Properties buy small single-tenant industrial buildings in Chicago, and they buy three out of every four of them with no debt at all. The ceiling is 30% loan-to-value. That boundary is not a strategy so much as a mental health requirement, and he is refreshingly blunt that it costs him upside. He is also one of maybe five syndicators in the country doing it. He does not know who the other four are. This is Joel's second appearance on the show. After the first one, Ed changed how Clark St underwrites deals. That is not a marketing line, it is what happened. What we get into: Why Joel compares over-leveraged real estate investors to gamblers, right down to the part where they hide the risk from their 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!

  6. Jul 7

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

    Gino Barbaro is a best-selling author and co-founder of Jake & Gino, but he did not start there. He opened a restaurant with his family in 1994, lost money on his early real estate deals, and only found his footing when he partnered with Jake, set hard parameters, and built a repeatable process for buying multifamily from mom-and-pop owners. That framework carried them through the last cycle without the blowups so many operators are living through now. Today Gino has transacted more than 2,600 units, owns 1,900, and his students have closed over 90,000 units and raised more than $800 million. This week on Real Estate Underground, Gino sits down with Ed Mathews to talk about the mindset underneath the numbers. His through line is simple and uncomfortable: money does not corrupt a person, it reveals them. And the reason two investors with the same deal get different outcomes usually comes down to what Gino calls financial flashpoints, the money memories each of us was raised inside. Save for a rainy day, money does not grow on trees, it takes money to make money. Gino spent years unlearning those beliefs before he could raise capital, syndicate, and build the portfolio he has now. What you will learn: Why your relationship with money, not your spreadsheet, decides whether you close deals, and how to spot the beliefs quietly holding you back. The mind shift from starting a business to make money to starting one to deliver value, and why Gino says it is the difference between one restaurant and six. Why the market moved from valuation through renovation to valuation through operations, and what that means for how you win now. The velocity of money, why you only make money when you exit, and the three things worth doing with capital after a sale. And why no deal is better than a bad deal, and how the ten-minute no became a superpower in a market where sellers still think it is 2021. Gino also shares the money-coaching business he is building with his wife and son at Barbaro360, why he believes legacy is not something you leave behind but something you activate today, and the six-acre farm in Florida where he goes to get his hands dirty. As he puts it, if you want to learn from someone, just make sure they are still doing it right now. If you are an operator trying to build something that lasts, this one is full of hard-won lessons from someone still in the work. Chapters 00:00 Your relationship with money starts everything 00:59 Welcome to Real Estate Underground 01:40 The name, and using AI as a force multiplier 02:40 Life before and after Jake and Gino 03:40 Money does not corrupt you, it reveals you 04:40 Why you really start a business: value for the marketplace 06:00 A stuck market and the grit AI can cost you 07:40 No motivated seller, no deal 10:40 Financial flashpoints: the money memories that shape you 14:30 Wealth is an exchange of value 16:20 Valuation through renovation vs valuation through operations 19:40 Velocity of money: what to do after you exit 22:40 Paying down debt as a legacy play 24:40 Retail, industrial, and the discipline to wait 29:20 The final five: purpose, mentors, and the biggest mistake 35:40 This week's book and where to find Gino This week's book: The Psychology of Money by Morgan Housel https://www.amazon.com/Psychology-Money-Timeless-lessons-happiness/dp/0857197681?tag=clarkstholdin-20 More Real Estate Underground episodes: clarkst.com/podcast Elevista: elevista.com/podcast Elevista - Speed as a Service™ Elevista Connect is the first AI-powered lead conversion system built for real estate investors. 🎧 Subscribe to Real Estate Underground for weekly insights on building wealth through real estate, without sacrificing your sanity. Additional Resources: Clark St Capital -> Passive real estate investments for busy business owners and 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. Jun 30

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

    Robbie Crager bought his first house at 25 with no money, bad credit, and no idea what he was doing. He had just lost a corporate job and had watched Carlton Sheets on late-night television promise he could buy a house with no money down. So he found a wholesaler in the newspaper, contracted the house, and jumped in with both feet while everyone around him begged him not to. Twenty-eight years and thousands of flips later, he calls it one of the best deals he ever did. This week on Real Estate Underground, Ed Mathews sits down with Robbie, the operator behind The FlipFlop Flipper, to talk about what it actually takes to run a lean flipping business at scale. Robbie spent two decades buying a couple of houses a week at Florida foreclosure sales. When the auctions moved online and margins got squeezed, he relocated to the island of Puerto Rico and started buying what locals call zombie houses: abandoned homes with no doors, no windows, no power, and nothing but upside. He renovates them back to the point where a first-time buyer can get an FHA loan, then hands over the keys. What you will learn: Why a 28-year operator who does not even carry a laptop has his team using AI every day, and why he believes anyone who refuses to learn it will be left at a disadvantage. The three-question filter Robbie runs before entering any new market: will our money go further, can we make a bigger return, and will our impact be one we are proud of. The single biggest mistake of his career, flipping a thousand houses before 2007 and keeping none of them, then losing everything in the crash. How he rebuilt by partnering with people who had capital instead of borrowing hard money, and started investing for cash flow instead of chunks of money. And the closing-table moment that still makes every renovation worth it. Robbie also shares the story behind a little red brick house in Ukraine. On a humanitarian trip in 2022 he helped a pastor buy a home big enough to adopt three boys out of an orphanage. That same house now shelters and feeds 70 orphans. As Robbie says, every house has a story, and that one is pretty good. The lightning round covers the joy of missing out, why he says no to most deals that cross his desk, the book he has read front to back five times, and how he defines success now that boats and fast cars stopped mattering. If you are an operator trying to build something that lasts, this one is full of hard-won lessons from someone still in the work. Find Robbie inside his free FlipFlop Flipper community on Skool, or on YouTube. Chapters 00:00 The leap of faith: no money, bad credit, no clue 00:59 Welcome to Real Estate Underground 02:14 28 years, thousands of houses, and Puerto Rico zombie homes 03:33 You don't have to stay in a broken system 04:07 Quitting at 25 and the Carlton Sheets first deal 06:40 Scaling to a couple of houses a week for 20 years 08:47 Using AI every day in a lean flipping business 10:32 The markets: Florida, the online shift, and Puerto Rico 11:23 The three-question filter for entering a new market 13:12 Investing with impact and the Ukraine orphanage house 17:44 Working with his son McKenna in the business 21:31 The deal you don't do: the joy of missing out 23:43 Purpose, legacy, and what gets him out of bed 26:11 The free FlipFlop Flipper community 26:46 The biggest mistake: flipping everything, keeping nothing 29:30 Lightning round: books, success, and travel 32:47 Where to find Robbie This week's book: Think and Grow Rich by Napoleon Hill https://www.amazon.com/Think-Grow-Rich-Publication-Foundation/dp/193787950X?tag=clarkstholdin-20 More Real Estate Underground episodes: clarkst.com/podcast Elevista: elevista.com/podcast Elevista - Speed as a Service™ Elevista Connect is the first AI-powered lead conversion system built for real estate investors. 🎧 Subscribe to Real Estate Underground for weekly insights on building wealth through real estate, without sacrificing your sanity. Additional Resources: Clark St Capital -> Passive real estate investments for busy business owners and 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. Jun 23

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

    For the 200th episode of the Real Estate Underground, the conversation lands on a city near and dear to Ed's heart: Detroit. His guests are James Lloyd and Voytek Mardula of US Properties, a Toronto-based team that has spent ten years building a full turnkey operation on the ground in Michigan. The thesis is contrarian and simple. While most people wrote Detroit off, James and Voytek heard it was in the early innings of recovery, drove down to see it for themselves, and found architecturally beautiful colonials in strong historic neighborhoods trading below the cost of construction. They sold off assets elsewhere, including a primary residence, and bought heavy. Ten years and 600-plus renovated homes later, they run a system that takes an investor from a first phone call to a cash-flowing landlord in 30 to 45 days. This episode is a practical map of remote and cross-border investing. You will hear how they vet a property with a 300-point pre-purchase inspection and block-level analysis, how a foreign national forms a US entity to qualify for financing, and why they refinance instead of flip to scale a portfolio. Voytek breaks down Detroit's 55,000-room hotel shortage against 17 million annual visitors and how that gap feeds their short-term rental strategy. Then the pair walk through the tax stack: opportunity zones that can wipe out capital gains after ten years, and bonus depreciation that can cover a down payment in year one. The Final Five turns personal: working alongside a lifelong best friend, the books that shaped them, and Voytek's deep dive into AI, which he calls the single most revolutionary tool of his lifetime. Find them at USProperties.ca. Chapters 00:00 The most undervalued market in the country 01:00 Welcome to the Real Estate Underground 02:00 Meet James Lloyd, Voytek Mardula, and US Properties 03:00 Why Detroit: the contrarian comeback thesis 05:00 Buying the right house in the right neighborhood 08:00 Managing a remote portfolio with a local team 11:00 The investor journey from first call to cash flow 13:00 The full turnkey system, step by step 14:00 Foreign nationals and US entity formation 16:00 Buy, hold, and refinance to scale 18:00 Short-term rentals and Detroit's hotel shortage 22:00 Opportunity zones and bonus depreciation 26:00 The auto industry and tech sector renaissance 31:00 The final five 32:00 What gets them out of bed 36:00 A decision they would take back 37:00 AI obsession and the book on the nightstand 40:00 Defining success and life off the clock 42:00 How to reach US Properties This week's book: You to the Power of Two: Redefining Human Potential in the Age of AI by Joseph Bradley and Don Tapscott More Real Estate Underground episodes: clarkst.com/podcast Elevista: elevista.com/podcast Elevista - Speed as a Service™ Elevista Connect is the first AI-powered lead conversion system built for real estate investors. 🎧 Subscribe to Real Estate Underground for weekly insights on building wealth through real estate, without sacrificing your sanity. Additional Resources: Clark St Capital -> Passive real estate investments for busy business owners and 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
17 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
    214
  • Rating
    Clean
  • Copyright
    © 2026 Clark St Holdings LLC
  • Show Website
    Real Estate Underground

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