Real Estate Underground

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

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

  1. 2d ago

    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-us 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!

    42 min

  2. May 26

    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 Elrod Guest: JB Thibodeaux, Founder & Managing Partner, J.B. Thibodeaux Homes & Properties Website: jbthibodeaux.com LinkedIn: linkedin.com/in/james-thibodeaux-8a98b51b7 Instagram: @jbthibodeauxhomes 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!

    42 min

  3. May 19

    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!

    29 min

  4. May 12

    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 Zinzer Guest: Adam Bell, Founder and CEO, Internet Subway Website: internetsubway.com LinkedIn: linkedin.com/in/adamlloydb 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!

    30 min

  5. May 5

    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 success Books mentioned: The Surrender Experiment and The Untethered Soul by Michael Singer Learn land development: learnlanddevelopment.com (free 8-hour course) Invest with HPG Capital: hbgcapital.net/waitlist 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!

    46 min

  6. Apr 28

    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 wrong Connect with Ben: benreinberg.com Real 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!

    34 min

  7. Apr 21

    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 size Resources 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!

    42 min

  8. Apr 14

    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 Martell Connect with Joel: brrrr.com Real 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!

    52 min
See All (204)

4.8
out of 5
18 Ratings

About

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

Information

  • Creator
    Ed Mathews
  • Years Active
    2018 - 2026
  • Episodes
    204
  • Rating
    Clean
  • Copyright
    © 2026 Clark St Holdings LLC
  • Show Website
    Real Estate Underground

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