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Real Estate Underground

Real Estate Underground

De : Ed Mathews
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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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Épisodes
  • 123% Leverage and the Crash That Changed Everything with Joel Kraut
    Apr 14 2026

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    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.

    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!

    🎧 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)
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    52 min
  • No Government Owns Us: Building a Global Real Estate Portfolio with Ladislas Maurice
    Apr 7 2026

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    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 US
    • How $200K in a Panama bank or $400K in Turkish real estate can buy generational citizenship and a Plan B for your family
    • The Ivory Coast deal that went wrong and why you should never skip the buyer's agent
    • His 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.

    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!

    🎧 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)
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    37 min
  • From Gold Bricks to Gold Coins: Real Estate Tokenization with Tyler Vinson
    Mar 31 2026

    Send us Fan Mail

    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.

    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!

    🎧 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)
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    52 min
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