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Real Estate Underground

Real Estate Underground

Written 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 Marketing & Sales Personal Finance
Episodes
  • Debt Is Gambling: The Zero-Debt Playbook with Joel Friedland

    Debt Is Gambling: The Zero-Debt Playbook with Joel Friedland
    Jul 14 2026

    Joel Friedland calls himself the most risk-averse real estate investor in the United States, and he has the scar tissue to prove it.

    In 2008 he was carrying $70 million in personal guarantees across 50 buildings. Ten of them were going to have to be sold at a loss. He sat his wife down and told her, and he watched her fall back in her chair. What followed was months of depression he describes without flinching in this conversation. He came out of it with a conclusion most investors never reach: the problem was not real estate, it was the way he was structuring the deals.

    Today Joel and his team at Brit Properties buy small single-tenant industrial buildings in Chicago, and they buy three out of every four of them with no debt at all. The ceiling is 30% loan-to-value. That boundary is not a strategy so much as a mental health requirement, and he is refreshingly blunt that it costs him upside.

    He is also one of maybe five syndicators in the country doing it. He does not know who the other four are.

    This is Joel's second appearance on the show. After the first one, Ed changed how Clark St underwrites deals. That is not a marketing line, it is what happened.

    What we get into:

    • Why Joel compares over-leveraged real estate investors to gamblers, right down to the part where they hide the risk from their spouses
    • The 2008 collapse in his own words, and the boundary he set on the other side of it
    • The buy box: single-tenant only, 7,000 to 30,000 square feet, no flex, no multi-tenant, and specific dock, ceiling-height and parking requirements
    • How 20 towns out of 200, and 700 buildings out of 17,000, makes the pipeline small enough to actually work, and why his team still knocks on doors to find deals
    • The secret-sauce exit: 77 of Joel's 82 sales went to owner-occupants who pay a premium over cap-rate buyers, not to investors
    • A live deal he is in the middle of on Stern Avenue, bought for $1.9M with $400K into the rehab, and the neighbor across the street who wants it
    • The Keebler building: bought for $6M, sold for $17M, a 40% IRR over a 15-year Comcast lease, and why that grand slam required the leverage he now avoids
    • Why his 250 investors, averaging roughly $20 million in net worth, are not looking to get rich, and are looking for somewhere that is not the casino
    • Reshoring, tariffs, and the honest math on why manufacturing is not all coming back
    • The batter who never strikes out

    Lightning round: the mentors (the Podolsky family, and 99-year-old Nate Wagner, who Joel has bought breakfast nearly every Saturday for 15 years), the deal he wants back, the book on his nightstand, and how he defines success.


    Connect with Joel Friedland

    Brit Properties: britproperties.com


    Book mentioned

    1929 by Andrew Ross Sorkin: find it on Amazon


    Connect with Ed Mathews and Clark St Capital

    Website: clarkst.com

    Newsletter: Underground Insights

    Submit a deal: clarkst.com/submit-your-deal

    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
    53 mins
  • Money Reveals You: Gino Barbaro on the Mindset Behind 2,600 Units

    Money Reveals You: Gino Barbaro on the Mindset Behind 2,600 Units
    Jul 7 2026
    Gino Barbaro is a best-selling author and co-founder of Jake & Gino, but he did not start there. He opened a restaurant with his family in 1994, lost money on his early real estate deals, and only found his footing when he partnered with Jake, set hard parameters, and built a repeatable process for buying multifamily from mom-and-pop owners. That framework carried them through the last cycle without the blowups so many operators are living through now. Today Gino has transacted more than 2,600 units, owns 1,900, and his students have closed over 90,000 units and raised more than $800 million. This week on Real Estate Underground, Gino sits down with Ed Mathews to talk about the mindset underneath the numbers. His through line is simple and uncomfortable: money does not corrupt a person, it reveals them. And the reason two investors with the same deal get different outcomes usually comes down to what Gino calls financial flashpoints, the money memories each of us was raised inside. Save for a rainy day, money does not grow on trees, it takes money to make money. Gino spent years unlearning those beliefs before he could raise capital, syndicate, and build the portfolio he has now. What you will learn: Why your relationship with money, not your spreadsheet, decides whether you close deals, and how to spot the beliefs quietly holding you back. The mind shift from starting a business to make money to starting one to deliver value, and why Gino says it is the difference between one restaurant and six. Why the market moved from valuation through renovation to valuation through operations, and what that means for how you win now. The velocity of money, why you only make money when you exit, and the three things worth doing with capital after a sale. And why no deal is better than a bad deal, and how the ten-minute no became a superpower in a market where sellers still think it is 2021. Gino also shares the money-coaching business he is building with his wife and son at Barbaro360, why he believes legacy is not something you leave behind but something you activate today, and the six-acre farm in Florida where he goes to get his hands dirty. As he puts it, if you want to learn from someone, just make sure they are still doing it right now. If you are an operator trying to build something that lasts, this one is full of hard-won lessons from someone still in the work. Chapters 00:00 Your relationship with money starts everything 00:59 Welcome to Real Estate Underground 01:40 The name, and using AI as a force multiplier 02:40 Life before and after Jake and Gino 03:40 Money does not corrupt you, it reveals you 04:40 Why you really start a business: value for the marketplace 06:00 A stuck market and the grit AI can cost you 07:40 No motivated seller, no deal 10:40 Financial flashpoints: the money memories that shape you 14:30 Wealth is an exchange of value 16:20 Valuation through renovation vs valuation through operations 19:40 Velocity of money: what to do after you exit 22:40 Paying down debt as a legacy play 24:40 Retail, industrial, and the discipline to wait 29:20 The final five: purpose, mentors, and the biggest mistake 35:40 This week's book and where to find Gino This week's book: The Psychology of Money by Morgan Housel https://www.amazon.com/Psychology-Money-Timeless-lessons-happiness/dp/0857197681?tag=clarkstholdin-20 More Real Estate Underground episodes: clarkst.com/podcast Elevista: 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 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!
    Show More Show Less
    39 mins
  • 3,000 Flips, Zero Tech Background: How Robbie Crager Uses AI to Scale

    3,000 Flips, Zero Tech Background: How Robbie Crager Uses AI to Scale
    Jun 30 2026
    Robbie Crager bought his first house at 25 with no money, bad credit, and no idea what he was doing. He had just lost a corporate job and had watched Carlton Sheets on late-night television promise he could buy a house with no money down. So he found a wholesaler in the newspaper, contracted the house, and jumped in with both feet while everyone around him begged him not to. Twenty-eight years and thousands of flips later, he calls it one of the best deals he ever did. This week on Real Estate Underground, Ed Mathews sits down with Robbie, the operator behind The FlipFlop Flipper, to talk about what it actually takes to run a lean flipping business at scale. Robbie spent two decades buying a couple of houses a week at Florida foreclosure sales. When the auctions moved online and margins got squeezed, he relocated to the island of Puerto Rico and started buying what locals call zombie houses: abandoned homes with no doors, no windows, no power, and nothing but upside. He renovates them back to the point where a first-time buyer can get an FHA loan, then hands over the keys. What you will learn: Why a 28-year operator who does not even carry a laptop has his team using AI every day, and why he believes anyone who refuses to learn it will be left at a disadvantage. The three-question filter Robbie runs before entering any new market: will our money go further, can we make a bigger return, and will our impact be one we are proud of. The single biggest mistake of his career, flipping a thousand houses before 2007 and keeping none of them, then losing everything in the crash. How he rebuilt by partnering with people who had capital instead of borrowing hard money, and started investing for cash flow instead of chunks of money. And the closing-table moment that still makes every renovation worth it. Robbie also shares the story behind a little red brick house in Ukraine. On a humanitarian trip in 2022 he helped a pastor buy a home big enough to adopt three boys out of an orphanage. That same house now shelters and feeds 70 orphans. As Robbie says, every house has a story, and that one is pretty good. The lightning round covers the joy of missing out, why he says no to most deals that cross his desk, the book he has read front to back five times, and how he defines success now that boats and fast cars stopped mattering. If you are an operator trying to build something that lasts, this one is full of hard-won lessons from someone still in the work. Find Robbie inside his free FlipFlop Flipper community on Skool, or on YouTube. Chapters 00:00 The leap of faith: no money, bad credit, no clue 00:59 Welcome to Real Estate Underground 02:14 28 years, thousands of houses, and Puerto Rico zombie homes 03:33 You don't have to stay in a broken system 04:07 Quitting at 25 and the Carlton Sheets first deal 06:40 Scaling to a couple of houses a week for 20 years 08:47 Using AI every day in a lean flipping business 10:32 The markets: Florida, the online shift, and Puerto Rico 11:23 The three-question filter for entering a new market 13:12 Investing with impact and the Ukraine orphanage house 17:44 Working with his son McKenna in the business 21:31 The deal you don't do: the joy of missing out 23:43 Purpose, legacy, and what gets him out of bed 26:11 The free FlipFlop Flipper community 26:46 The biggest mistake: flipping everything, keeping nothing 29:30 Lightning round: books, success, and travel 32:47 Where to find Robbie This week's book: Think and Grow Rich by Napoleon Hill https://www.amazon.com/Think-Grow-Rich-Publication-Foundation/dp/193787950X?tag=clarkstholdin-20 More Real Estate Underground episodes: clarkst.com/podcast Elevista: 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 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!
    Show More Show Less
    35 mins
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