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Real Estate Underground

Real Estate Underground

Hosted by Ed Mathews

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Episodes

198

Latest episode

Jun 2026

Language

EN

About the show

Real talk from an operator who learned real estate the hard way. Ed Mathews analyzed 1,100+ deals before buying his first property in 2011. Frozen in fear. He made every mistake, all while traveling 150+ nights a year working for some of Silicon Valley's top companies. 100+ deals later, he shares what actually works and what doesn't. Each week, Ed brings you candid conversations with experienced operators, investors, and syndicators. No hype. No theory. Just real deals, real lessons, and the street-level intelligence you won't find anywhere else. You'll learn and hear about: Deals that worked (and the ones that didn't) What we learned when contractors ghosted and we had to step in How to vet opportunities when everyone else is sitting on the sidelines Conservative underwriting in markets that punish optimism Systems that protect capital when deals go sideways Whether you're analyzing your first deal or your hundredth, this is the conversation you'd have over coffee with someone who's been there, made the mistakes, learned the lessons and built the track record. New episodes every Tuesday at 12pm ET.

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60 recent
June 16, 2026Episode 19940 min

Tom Dunkel's SAFE Method: Vetting Every Deal Before You Invest

If you are within three feet of Ed Mathews, you are probably talking about real estate. This week the conversation is with Tom Dunkel, managing principal at Eagle Capital Investments, and it is a clinic in how to vet a deal before a dollar leaves your account. Tom has been a full-time investor for two decades. Over that span he has raised more than $50 million in private capital from a network of investors who lean on his experience to place money into alternatives most people never see: multifamily, self-storage, mobile home parks, medical office, and private lending. His pitch is simple. Real diversification is not large cap versus small cap or value versus growth. It is owning assets that do not move when a headline does. As Tom puts it, a tsunami hitting Japan can knock the stock market down 15 percent overnight, but it does nothing to an apartment building in Phoenix or a storage facility in North Carolina. The backbone of the episode is Tom's SAFE Investing Method, the same screen he uses every day. S is for sponsor: who are you writing the check to, what is their track record, and have you earned the right to ask the hard questions. A is for asset: if you cannot explain the investment to your kid or your elderly parent, you do not understand it well enough to fund it. F is for financials: do the projections hold up, and has this sponsor actually hit numbers like these before. E is for exit: you cannot click your way out of a syndication on a Tuesday afternoon, so you need to know exactly what has to happen, and over what time horizon, before your money comes back. Then Tom goes off the mainstream script on taxes. The standard advice is to 1031 exchange again and again until you die and hand your heirs a stepped-up basis. Tom's question is blunt: do you really want to be managing properties at 90 the way his mother could be. He prefers the lazy man's 1031, taking the gain, then using fresh depreciation from the next deal to shelter income, all without the rigid timelines and same-title rules that make a true 1031 nearly impossible across a group of 20 or 30 investors. Pay the freedom tax, he argues, and buy yourself passive income and time. The buy box conversation is just as practical. Tom likes private lending for first-position security and monthly checks. He likes mobile home parks and co-living because they answer the housing affordability crisis with real, unsubsidized supply, and he breaks down how a Philadelphia operator turns a $1,000 row home into $3,000 a month by renting furnished rooms to tenants on fixed income. He covers where self-storage sits after its boom and consolidation, and why he treats it like multifamily underwriting now. On technology, Tom is candid that he is still early but already getting leverage from AI. His current workflow is to go back and forth with Claude to build a long, specific prompt, then hand it to Manus for deep research on a market like Phoenix multifamily. He even has an AI clone at tomdunkel.ai that will answer your investing questions, as long as you do not bring up the Eagles. The lightning round digs into purpose beyond family, the best advice he ever got from a nine-figure investor, a job he probably should have turned down, and how he defines success now as an empty nester: geographic and time freedom, plus the room to give back through Tunnel to Towers and a scholarship he started for a friend lost to ALS. Find Tom at investwitheagle.com, grab his book The Wealth Builder's Playbook, or talk to his clone at tomdunkel.ai. Chapters 00:00 Don't let the tax tail wag the freedom dog 01:00 Meet Tom Dunkel and Eagle Capital Investments 03:00 Why true diversification lives outside the stock market 04:00 The SAFE Investing Method: Sponsor, Asset, Financials, Exit 08:00 Taxes and the lazy man's 1031 exchange 13:00 The Wealth Builder's Playbook and being the "who" 17:00 The buy box: mobile home parks, co-living, multifamily 22:00 Where self-storage sits after the boom 24:00 Using Claude and Manus to move faster 27:00 Lightning round: purpose, significance, and legacy 30:00 The best advice he ever got 33:00 A decision he would take back 34:00 On the nightstand: Invest Like a Billionaire 36:00 Defining success as an empty nester 38:00 Golf, a rock and roll cover band, and where to find Tom This week's book: Invest Like a Billionaire: Unlocking the Wealth Secrets of the Ultra-Rich by Bob Fraser and Ben Fraser https://www.amazon.com/dp/B0F3W2SNDS?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!

June 9, 2026Episode 19828 min

B-Class Property, A-Class Management: The Short-Term Rental Edge with Tim Hubbard

Short-term rentals are supposed to be the most hands-on asset class in real estate. Tim Hubbard runs hundreds of them across the U.S. and multiple countries—without ever being on the ground. Tim is the CEO and co-founder of Corzly, the virtual management company he built after 16 years of operating his own short-term rental portfolio from outside California, then outside the U.S. entirely. His team handles pricing, listings, guest communication, and back-end operations across Eastern Europe, South Africa, the Philippines, and South America—while the owner still controls the housekeepers and maintenance on the ground. In this episode, Tim and Ed get into why “a B-class property with A-class management beats an A-class property with B-class management,” why the urban short-term rental market is more durable than the vacation-rental crowd realizes, and what the data is actually telling operators about which markets to enter and which to avoid. What you’ll hear: Why the “can’t be hands-on AND remote” constraint is the forcing function that built Corzly—and what it means for any operator stuck in their own business The buy box: how Tim underwrites a short-term rental like an apartment building, what data sources actually matter, and the regulatory gotchas that kill deals Why urban short-term rentals quietly outperform vacation markets—more reasons to stay, less seasonal volatility, and the medical-professional and conference angles most investors miss The lightning round: under-budgeting renovations, Dennis Waitley’s “two choices” framing, and why education became Tim’s purpose once the portfolio could run itself Books Tim recommended: Who Not How by Dan Sullivan and Dr. Benjamin Hardy—the framework for finding the right people to delegate to The Slight Edge by Jeff Olson—Tim’s most-recommended book; the case for compounding small daily disciplines About Tim Hubbard: CEO and co-founder of Corzly. 16-year real estate operator. Host of Short Term Rental Riches, a six-year-old podcast covering virtual STR management, market selection, and the operational discipline behind scaled portfolios. Find Tim: corsley.com | Short Term Rental Riches podcast (all platforms + YouTube) Subscribe to Real Estate Underground for weekly conversations with operators who’ve been through the cycle and lived to talk about it. 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!

June 2, 2026Episode 19742 min

From X Games Gold to 3,300 Multifamily Units with Dan Brisse

What does it take for a professional snowboarder, six X Games appearances, gold and silver medals, fifteen years on tour, to land in real estate? For Dan Brisse, the answer was watching the guys five and ten years ahead of him lose their houses, their cars, and worse.That was the wake-up call. While most of his peers spent every pay raise on the biggest house they could buy, Dan was reading books and buying apartments. By the time his snowboarding career ended, he had 70-some units already producing passive income.Today Dan co-leads Granite Towers Equity Group, a 3,300-unit multifamily portfolio focused on Dallas-Fort Worth, Nashville, and select Minnesota submarkets. The playbook is disciplined: newer assets (1985 and up), 140 to 300 units, $20 to $40 million purchase price, 95%+ occupancy submarkets with real pent-up demand. Eighty-twenty split with LPs. Sixty-five to seventy-five percent loan-to-value, fixed rate, non-recourse. CapEx raised liquid up front, so the bank cannot force a bad spend.What you'll hear:The chairlift moment that reframed every financial decision Dan has made sinceWhy 78% of pro athletes are broke within three years of retirement and the side-hustle move he made to avoid joining themThe Cleburne, Texas case study: $6.75M acquisition, $2.1M LP raise, full-cycle returnsA second case study where interior upgrades and water conservation drove a 1.8x equity multiple in two yearsWhy Dan believes we are in a generational buying window with multifamily trading at 30-40% discounts versus 2021-22 peaksHis sharpest definition of wealth, and why "rich" and "wealthy" aren't the same thingLearn more about Granite Towers Equity Group: https://www.granitetowersequitygroup.com/contact-usElevista - 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!

May 26, 2026Episode 19642 min

Real Estate Hustle vs. Real Estate Business with JB Thibodeaux

JB Thibodeaux grew up in Acres Homes in Houston and is a third-generation carpenter and concrete specialist who turned that craft into a vertically-integrated real estate development business. His firms, J.B. Thibodeaux Homes & Properties, CCB Construction LLC, and CCB General Contractors LLC, have led over $100 million in projects across mass development, pocket development, and affordable housing infill. This year, the Houston market crowned him the "Duplex King."In this episode, Ed and JB unpack a contrarian lesson the real estate education industry rarely teaches: the difference between the real estate hustle and the real estate business. Hustle gets you doors. Business gets you a sustainable enterprise. Most operators only ever learn the first one.JB walks through the Houston duplex pricing math that vindicated his long conviction on the market, from "praying to get $350" on a 2,500 square foot duplex to selling at $479, almost $500,000. He explains his concept-to-keys pocket-development model, Houston's no-zoning-but-deed-restrictions quirk, the 60/40 build-to-sell vs. build-to-hold split for his client base, and why vertical integration (owning the GC) is a margin lever most flippers underestimate.In this episode:Pocket development inside a major metro: the frameworkThe duplex math that vindicated a Houston long-holdHouston's "no zoning" reality: where the leverage actually livesWhy "the gurus teach you doors, not business"House hacking as the duplex exit strategyGenerational construction knowledge as competitive moatMayor Sylvester Turner naming February 20 "James 'JB' Thibodeaux Day" (2019)If you're a flipper, wholesaler, or operator trying to build a business and not just a deal pipeline, this is the episode.This week's book: The Miracle Morning by Hal ElrodGuest: JB Thibodeaux, Founder & Managing Partner, J.B. Thibodeaux Homes & PropertiesWebsite: jbthibodeaux.comLinkedIn: linkedin.com/in/james-thibodeaux-8a98b51b7Instagram: @jbthibodeauxhomesElevista - 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!

May 19, 2026Episode 19529 min

400 1031s, Zero Failures: The Senior-Care Niche Hiding in Plain Sight with Dan Ihara

Dan Ihara has sold over $1 billion of real estate, moved 1,600+ units, and completed 400+ 1031 exchanges—without failing a single one.And he built the whole thing around a niche almost no operator talks about: senior-care real estate.In this episode, Dan and Ed get into the demographic inevitability that drives his business (“should we all be blessed to live long enough, we’re going to need some level of care”), why 1031 exchanges fail for everyone else but never for him, and his definition of success that has nothing to do with the billion-dollar number on his resumé.What you’ll hear:The senior-care thesis: why aging boomers are an inevitability, not a trend, and the RE play sitting on top of itHow Dan closed 400 1031 exchanges without a single failure—the process, the team, the disciplineWhy “success is doing what I want, when I want, with whom I want” is the only definition that matters once you have the numbersThe conversation every operator should be having with their family—and almost none areAbout Dan Ihara: 20-year real estate veteran. Billion-dollar producer. Built a specialty practice serving seniors transitioning out of long-held real estate, primarily through 1031 exchanges.Subscribe to Real Estate Underground for weekly conversations with operators who’ve been through the cycle and lived to talk about it.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!

May 12, 2026Episode 19429 min

Internet Isn't a Tenant Cost...It's an NOI Lever - with Adam Bell

Most multifamily operators treat internet as a tenant problem or a cost line they grumble about. Adam Bell, Founder and CEO of Internet Subway, says they're leaving real money on the table.Adam runs a modern ISP focused exclusively on apartment communities. His company delivers fiber-to-the-unit (FTTU) in bulk to property owners, who pass it to residents as an included utility and capture the rent spread. Industry data shows 5 to 15% NOI uplift on well-executed bulk deployments. The math alone is worth the conversation.But the bigger reframe is the one Ed pulls out of him halfway through: the fiber itself is an asset. Billions are flowing into fiber networks nationally. Property owners are in a rare position to own a portion of that infrastructure, a 30-year asset hiding in their own buildings.In this episode:The bulk internet math on a value-add multifamily deal, and how an owner should actually underwrite itWhy "managed WiFi" gets oversold and what to insist on insteadBulk internet versus experience, and why the difference matters more than the priceFiber as a 30-year asset class that scales in capacity, not maintenanceThe contrarian take from his industry piece "Managed Wi-Fi isn't all it's cracked up to be"If you're an operator, syndicator, or value-add multifamily investor, this is the episode that turns a cost line into a revenue line and reframes the building itself as a fiber asset.This week's recommended book: The Confident Mind by Nate ZinzerGuest: Adam Bell, Founder and CEO, Internet SubwayWebsite: internetsubway.comLinkedIn: linkedin.com/in/adamlloydbElevista - 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!

May 5, 2026Episode 19346 min

Plan A, B, and C: Buy More Land with Brandon Cobb

Brandon Cobb's business model is simple: take farmland, get it approved for housing, and sell it to national home builders like Lennar and DR Horton. The builders have no choice but to buy. They're publicly traded. Plan A is buy land and build houses. Plan B is buy more land and build more houses. There is no Plan C that doesn't involve buying land.Brandon returns to Real Estate Underground to break down how HPG Capital creates new housing neighborhoods in Nashville, why he stopped building homes but kept developing land, and how he structures deals that pay investors 18% preferred returns with no personal guarantees.What you'll learn:- The three phases of land development and how to profit from each one without ever building a house- How to de-risk a deal by lining up your buyer and getting city approval before spending real money- Why "big puzzle pieces next to small puzzle pieces" on a GIS map is the buy signal- How he gets 20% deposits from national builders, released day one, to fund development- Why he ditched vertical integration after hitting $22 million in annual development- The biggest mistake he made with strategic partners and how to avoid it- His "Body, Being, Balance, Business" framework for measuring successBooks mentioned: The Surrender Experiment and The Untethered Soul by Michael SingerLearn land development: learnlanddevelopment.com (free 8-hour course)Invest with HPG Capital: hbgcapital.net/waitlistElevista - 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!

April 28, 2026Episode 19234 min

It's Not Gambling, It's Building: A Billion-Dollar CRE Playbook with Ben Reinberg

Ben Reinberg has done over $1 billion in commercial real estate transactions. He didn't get there chasing returns. He got there by treating CRE as what it actually is: a hard asset that produces cash flow, not a bet.Ben is the Founder and CEO of Alliance CGC, where he's built one of the most respected portfolios in the country, with deep focus on net-leased properties and medical office buildings.In this episode, Ben and Ed cover:- Why medical office is recession-resistant in any market (the "human body never goes out of style" rule)- The over-leverage mistake that taught Ben the real lesson of commercial real estate- Cash flow, tax efficiency, and long-term security as the only three goals worth chasing- How to navigate one of the most chaotic markets in decades- The difference between treating real estate as a commodity vs. a hard asset- What old-school CRE investors do that the new wave gets wrongConnect with Ben: benreinberg.comReal Estate Underground is hosted by Ed Mathews of Clark St Capital.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!

April 21, 2026Episode 19142 min

Obscurity is the Enemy: AI, Marketing, and the Operator's Edge with Clay Lehman

Clay Lehman spent 20 years in real estate, starting at Arthur Andersen, running the Ocala controller desk for Pulte Homes, and eventually building Lehman's Strategic Partners to help agents grow their businesses. He runs an AI Facebook group with members in 65 countries and now spends most of his time helping real estate pros turn AI from a shiny object into a revenue tool. If you're still using AI to write listing descriptions and calling it a day, this one will push your thinking.In this episode you'll learn:- Why Clay calls obscurity, not competition, the biggest threat to any real estate business- How the "eliminate, automate, delegate" framework turns documented processes into leverage- Which AI tools Clay actually uses daily, and how Gemini, Claude, and ChatGPT scored in his blind writing test- How Ed built an AI voice agent that gets a lead on the phone in 45 seconds, across five languages- Why the Harvard 391% rule makes speed-to-lead the single biggest edge in real estate today- How solo operators and small teams can look and act like companies many times their sizeResources Mentioned: Google NotebookLM for deal prep and process documentation. Gamma for instant presentations. ylopo for lead nurture automation.Takeaway: AI is a force multiplier, not a crutch. It levels the playing field on access, but experience and wisdom still do the heavy lifting. Use it as the spotter at the gym, not the guy lifting the weight.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!

April 14, 2026Episode 19052 min

123% Leverage and the Crash That Changed Everything with Joel Kraut

Joel Kraut co-founded BRRRR Loans after losing $4.2 million in the 2008 crash. He had 144 properties at over 100% leverage when the market turned. Five tenants called the same day to say they couldn't pay rent.Today he runs one of the country's fastest-growing private lending shops, and he sees the DSCR lending industry doubling in size over the next three years.In this episode, Joel and Ed break down:- Why investors are rotating from Texas and Florida to Ohio, Kentucky, and the Midwest- How DSCR loans actually work (and why 1.0 coverage isn't enough)- The real math on leverage: why the smartest investors stay at 60% LTV or below- Why "relationship capital" matters more than real estate knowledge- What happened when Joel wired money on March 5, 2020 and the market froze- His $99 training modules vs. the $35K guru trap- The best advice he ever got: "Post that in 5 years. Shut up. Go back to work."Joel currently reads: Buy Back Your Time by Dan MartellConnect with Joel: brrrr.comReal Estate Underground is hosted by Ed Mathews of Clark St Capital.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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