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Real Estate Underground

Real Estate Underground

Autor: 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 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.

© 2026 Clark St Holdings LLC
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  • 18% Over 10 Years Beats 20% in Three: Forrest Jinks of Altus Equity Group
    Oct 13 2026

    Forrest Jinks runs Altus Equity Group, a real estate investment company that works with family offices and high net worth investors. Most sponsors chase top-line IRR: get in, get out in two, three or four years. Forrest says that leaves a lot of meat on the bone. "It might be awesome to get an 18% return over 10 years versus a 20% return in three." He cares about the net return, after taxes, and about how much risk sits behind the number.

    Altus runs a lending side too, and Forrest underwrites every loan like an owner. His first question: would we love to own this in our equity business at the debt amount plus foreclosure costs? "If the answer is yes, we're gonna figure out a way to make that loan work."

    What Ed and Forrest get into:

    • Why a 12% first-position loan at 30% loan to value can beat an 18% ground-up construction deal
    • An industrial building in Mississippi bought for $12 a foot, and the Fortune 500 tenant that signed first
    • Why Forrest calls the Altus debt fund "effectively a proxy for the 10-year Treasury"
    • Walking the property, on equity deals and on loans
    • No back-end leverage, and why Ed's debt fund doesn't borrow to lend either
    • Why the biggest red flag in an investor is wanting to get rich quick
    • Holding for 10 years or more, and why real estate's wider band lets you buy low and sell high in any part of the cycle
    • The day Forrest decided to build a company instead of doing three or four deals a year
    • The promise he made to investors before 2008, and why he'll never make it again
    • His daughter's olive oil business, and why her $7,000 from him is an investment, not a gift

    Also in this episode, Questions from the Underground: Jose's lender approved half his draw, and his contractor says no money, no work. Ed covers why the fight is really about the definition of done, why your project schedule and your draw schedule need the exact same language, and why you carry a 10 to 20% contingency.

    Book mentioned:

    • Making the Zeros Count, Forrest's pick

    Read the Altus Insight, Forrest's monthly article on investing and economics, at altusequity.com/insights.

    Got a question you want answered on the show? Send it to ed@clarkst.com.

    Recorded September 2026.

    Real Estate Underground with Ed Mathews. Find us wherever you get your podcasts, at clarkst.com/podcast or 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 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!

    Rozwiń Zwiń
    55 min
  • Building an AI Investment Committee: Palmy Kitti of The Kitti Sisters
    Oct 6 2026

    Palmy Kitti and her sister Nan started a fashion business with $2,000. Years later their biggest client shut down all its retail stores and 95% of their income was gone overnight. They moved into flipping houses in Los Angeles, then into multifamily syndication. Seven and a half years in, Palmy says they have nearly half a billion dollars in assets under management across Georgia, Arkansas and Texas.

    Now a lot of that business runs through AI. After a property management changeover, her system flagged that one property had more cash than its reports showed. They'd overfunded the reserve account by $169,000. Finding that used to mean people matching rent rolls against the T12 and the general ledger by hand. She says it took her less than five minutes.

    She's just as clear about where AI stops. "You can have the best AI tools, but AI doesn't give you that judgment. You have to make that judgment."

    What Ed and Palmy get into:

    • The $169,000 her AI caught in a reserve account after a property management changeover
    • A fire that burned eight units with only two occupied, and the eight-page report that got the insurer to approve business interruption on all eight: $136,000 through August versus $32,000 for two
    • Her AI investment committee, with a risk role, a capital role and a market role that each try to find the flaws in a deal before a CEO role sums it up
    • Why AI multiplies the advantage you already have and can't create one for you
    • Ed's rule for the AI agents in his flip business: they handle execution, never judgment
    • How a newer investor can use AI to bring real value to an experienced general partner
    • The partner who stole her investor list, and the partners who went quiet during a refinance
    • Why drinks on Thursday doesn't mean you get married on Saturday
    • The investor on their dead list who invested five years later
    • "Earn to own," and what Fortune Builders taught her about owning assets before buying things

    Also in this episode, Questions from the Underground: when do I quit the job? Ed covers what has to be in place before you leave your W-2: insurance, cash reserves, debt, plus structure and protection.

    Book mentioned:

    • The Innovation Secrets of Steve Jobs by Carmine Gallo, Palmy's pick

    Learn about Palmy's AI operating system at kittiroadmap.com, and find The Kitti Sisters at thekittisisters.com and on YouTube, TikTok, Instagram and Facebook.

    Got a question you want answered on the show? Send it to ed@clarkst.com.

    Recorded September 2026.

    Real Estate Underground with Ed Mathews. Find us wherever you get your podcasts, at clarkst.com/podcast or 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 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!

    Rozwiń Zwiń
    48 min
  • How a PhD Underwrites Apartments: Jason Williams of Ironclad Underwriting
    Sep 29 2026

    Jason Williams spent 15 years as a chemical engineer. He's owned real estate since 2003 and large multifamily since 2017. When he started underwriting apartments, half the spreadsheets he was handed had broken cells and equations that didn't work, so he built his own model. People kept asking him to show them how it worked, and that model became Ironclad Underwriting.

    His rule is simple: never underwrite off your own numbers. The property manager tells him what each unit can rent for. The insurance broker prices the premium off comparable properties, and he uses the high end of the range. A tax advisor fights the assessment. And the plumber's bid gets multiplied by three, sometimes four.

    "Every single property I've had from a 1950s build up to early 2000s has had major plumbing issues."

    What Ed and Jason get into:

    • Why a T12 almost never ties to the bank statements, and when that gap is actually a red flag
    • Rent rolls that look clean but hide a rollover cliff, and why the manager, not the spreadsheet, sets pro forma rents
    • Insurance priced on replacement cost, and what Texas nondisclosure does to your tax bill after you buy
    • The tax advisor who saved him $20,000 one year and $11,000 this year, paid only on a percentage of what he saves
    • Why he no longer chases agency debt, even with the better rates
    • A 72-unit plumbing job that put residents in a hotel for two weeks, and a gas leak that shut off the gas over Easter weekend
    • Ed's sewer line on a 10-unit building that passed inspection: a $5,000 to $10,000 fix at purchase that became $44,000 a year and a half later
    • Six months of reserves, and why Ed doubled his after the pandemic
    • The zoning mistake on a mobile home community that has cost Jason more than a year of unexpected debt service

    Also in this episode, Questions from the Underground. An experienced Connecticut investor asked Ed whether it's time to cycle back to cash flow deals or keep riding the appreciation wave. Ed's answer: it's always a cash flow play. Appreciation is the cherry on top, not the basis of a business plan.

    Books mentioned:

    • Who Not How by Dan Sullivan with Dr. Benjamin Hardy, Jason's favorite
    • The E-Myth Revisited by Michael E. Gerber

    Connect with Jason Williams at ironcladunderwriting.com, or on LinkedIn. His free underwriting resources and his weekly underwriting podcast are on the site.

    Got a question you want answered on the show? Send it to ed@clarkst.com.

    Recorded September 2026.

    Real Estate Underground with Ed Mathews. Find us wherever you get your podcasts, at clarkst.com/podcast or 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 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!

    Rozwiń Zwiń
    42 min
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