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 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 weekly.

  1. 1D AGO

    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

  2. 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

  3. 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

  4. 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

  5. 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

  6. 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

  7. APR 7

    No Government Owns Us: Building a Global Real Estate Portfolio with Ladislas Maurice

    Ladislas Maurice left a corporate career at Nestle to spend the last nine years investing in real estate across emerging and frontier markets around the world. He buys apartments in Nairobi for $65,000, sits on land in Nicaragua, and flips properties in Montenegro. His approach is the opposite of what most US investors are used to: no leverage, no perfect data, and no rushing. In this episode, Ed and Ladislas talk about: Why emerging market real estate is actually a harder asset than US multifamily (and arguably less risky)How he evaluates a new country before putting money in (the Uzbekistan stock exchange story is worth the listen alone)Managing property across dozens of countries with local property managers (and why you always need a backup)The case for putting a small percentage of your portfolio outside the USHow $200K in a Panama bank or $400K in Turkish real estate can buy generational citizenship and a Plan B for your familyThe Ivory Coast deal that went wrong and why you should never skip the buyer's agentHis father's best advice: "You don't have to answer every question"Learn more about Ladislas at The Wandering Investor and on YouTube. 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!

    37 min

  8. MAR 31

    From Gold Bricks to Gold Coins: Real Estate Tokenization with Tyler Vinson

    Tyler Vinson has spent 25 years in investment real estate, from duplexes and flips to multifamily, commercial, and Class A storage. Now he's building the infrastructure to bring real estate into the digital age as the founder of RE Tokens, one of only about 10 companies in the US with an SEC-registered digital broker dealer ATS license, and the only one focused exclusively on real estate. In this episode, Tyler breaks down what real estate tokenization actually is, how it enhances (not replaces) traditional syndication, and why it matters for both GPs and LPs. He explains how restricted shares can become tradeable digital assets, how non-accredited investors can participate after 12 months under Rule 144, and what the secondary marketplace looks like in practice. He also shares the personal story that became his mission: a friend from high school who wanted to invest but didn't qualify. We also get into the lessons Tyler learned from being over-leveraged during the 2008 financial crisis, his disciplined approach to education, and why the future of real estate investing is undeniably digital. What you'll learn in this episode: - What real estate tokenization is and how it works (the gold brick to gold coins analogy) - How tokenization creates a pathway to liquidity for traditionally illiquid LP positions - The SEC compliance framework: Rule 144, ATS marketplaces, and why registration matters - How non-accredited investors can access deals that were previously off limits - Why over-leverage is the #1 risk in real estate and how Tyler rebuilt after 2008 Book on Tyler's nightstand: The Power of the Subconscious Mind by Dr. Joseph Murphy Connect with Tyler Vinson and RE Tokens: - Website: retokens.com (free Quick Start Guide to Real Estate Tokenization) - LinkedIn: Tyler Vinson / RE Tokens - YouTube: RE Tokens 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 (202)

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 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 weekly.

Information

  • Creator
    Ed Mathews
  • Years Active
    2018 - 2026
  • Episodes
    202
  • Rating
    Clean
  • Copyright
    © 2026 Clark St Holdings LLC
  • Show Website
    Real Estate Underground

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