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Real Estate Underground

Real Estate Underground

Written by: Ed Mathews
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About this listen

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 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 weekly.

© 2026 Clark St Holdings LLC
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Episodes
  • 400 1031s, Zero Failures: The Senior-Care Niche Hiding in Plain Sight with Dan Ihara
    May 19 2026

    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 it
    • How Dan closed 400 1031 exchanges without a single failure—the process, the team, the discipline
    • Why “success is doing what I want, when I want, with whom I want” is the only definition that matters once you have the numbers
    • The conversation every operator should be having with their family—and almost none are

    About 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 executives
    • Elevista -> AI SaaS for real estate investors
    • Clark St Academy on YouTube -> Learn how to invest in real estate

    Social 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!

    Show More Show Less
    29 mins
  • Internet Isn't a Tenant Cost...It's an NOI Lever - with Adam Bell
    May 12 2026

    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 it
    • Why "managed WiFi" gets oversold and what to insist on instead
    • Bulk internet versus experience, and why the difference matters more than the price
    • Fiber as a 30-year asset class that scales in capacity, not maintenance
    • The 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 executives
    • Elevista -> AI SaaS for real estate investors
    • Clark St Academy on YouTube -> Learn how to invest in real estate

    Social 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!

    Show More Show Less
    30 mins
  • Plan A, B, and C: Buy More Land with Brandon Cobb
    May 5 2026

    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 executives
    • Elevista -> AI SaaS for real estate investors
    • Clark St Academy on YouTube -> Learn how to invest in real estate

    Social 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!

    Show More Show Less
    46 mins
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