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Real Estate Underground

Real Estate Underground

By: 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
Economics Leadership Management & Leadership Marketing & Sales Personal Finance
Episodes
  • Renting Dirt: Nasir Ali of Rise360 Ventures on Manufactured Housing Communities
    20 Oct 2026

    Nasir Ali runs Rise360 Ventures. He comes from eight generations in commercial real estate and is the second generation in manufactured housing, a business his family just marked 45 years in, through at least nine downturns. His case for the asset class is simple. "We own the land. And sure the common areas and whatnot, but essentially we're renting dirt." No plumbing, no electrical, no toilets for every unit. "I don't own the damn door."

    Nasir also thinks the hard part of the cycle hasn't hit yet. As credit tightens, he says, it sets the stage for more creativity, more creative financing and alternative financing. And when budgets get cut, "people drop what they don't need. You can't drop shelter."

    What Ed and Nasir get into:

    • The late-1970s playbook, and why investors who couldn't adapt were left behind
    • Commercial defaults in office and retail, and why they still hit everyone in commercial real estate through the banks
    • Seller financing, master leases and the other options when bank lending dries up
    • Why manufactured housing has been resilient, not just recession resistant
    • "There's plenty of housing. The problem is it's not affordable." Affordability versus attainability
    • Filling half-empty communities with a dealer arm, financing and turnkey three-bed, two-bath homes
    • The get rich slow scheme: a three to five year journey from 60 or 70% occupancy to full
    • What eight generations passed down when the money was lost: tenacity, knowledge and values
    • The HVAC company he bought after 2008 that cratered overnight, and why you make sure you understand your domain
    • Why his definition of success is one word

    Also in this episode, Questions from the Underground, from Dave in San Clemente, California: an investor rehabbed and rented a house, and the refi appraisal came in short of what he needed to pull his cash back out. Ed covers why you need to be proactive with appraisers, not reactive, the packet he gives every appraiser, why any pushback is about the comp and not the number, and why he underwrites the refi at 90 to 95% of after rehab value before he buys.

    Book mentioned:

    • How to Win Friends and Influence People by Dale Carnegie, Nasir's pick

    Get Nasir's free manufactured housing report at rise360ventures.com, or find him on LinkedIn.

    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!

    Show more Show less
    52 min
  • 18% Over 10 Years Beats 20% in Three: Forrest Jinks of Altus Equity Group
    13 Oct 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!

    Show more Show less
    55 min
  • Building an AI Investment Committee: Palmy Kitti of The Kitti Sisters
    6 Oct 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!

    Show more Show less
    48 min
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