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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 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 Direction Economie Finances privées Management et direction Marketing et ventes
Épisodes
  • Tom Dunkel's SAFE Method: Vetting Every Deal Before You Invest

    Tom Dunkel's SAFE Method: Vetting Every Deal Before You Invest
    Jun 16 2026
    If you are within three feet of Ed Mathews, you are probably talking about real estate. This week the conversation is with Tom Dunkel, managing principal at Eagle Capital Investments, and it is a clinic in how to vet a deal before a dollar leaves your account. Tom has been a full-time investor for two decades. Over that span he has raised more than $50 million in private capital from a network of investors who lean on his experience to place money into alternatives most people never see: multifamily, self-storage, mobile home parks, medical office, and private lending. His pitch is simple. Real diversification is not large cap versus small cap or value versus growth. It is owning assets that do not move when a headline does. As Tom puts it, a tsunami hitting Japan can knock the stock market down 15 percent overnight, but it does nothing to an apartment building in Phoenix or a storage facility in North Carolina. The backbone of the episode is Tom's SAFE Investing Method, the same screen he uses every day. S is for sponsor: who are you writing the check to, what is their track record, and have you earned the right to ask the hard questions. A is for asset: if you cannot explain the investment to your kid or your elderly parent, you do not understand it well enough to fund it. F is for financials: do the projections hold up, and has this sponsor actually hit numbers like these before. E is for exit: you cannot click your way out of a syndication on a Tuesday afternoon, so you need to know exactly what has to happen, and over what time horizon, before your money comes back. Then Tom goes off the mainstream script on taxes. The standard advice is to 1031 exchange again and again until you die and hand your heirs a stepped-up basis. Tom's question is blunt: do you really want to be managing properties at 90 the way his mother could be. He prefers the lazy man's 1031, taking the gain, then using fresh depreciation from the next deal to shelter income, all without the rigid timelines and same-title rules that make a true 1031 nearly impossible across a group of 20 or 30 investors. Pay the freedom tax, he argues, and buy yourself passive income and time. The buy box conversation is just as practical. Tom likes private lending for first-position security and monthly checks. He likes mobile home parks and co-living because they answer the housing affordability crisis with real, unsubsidized supply, and he breaks down how a Philadelphia operator turns a $1,000 row home into $3,000 a month by renting furnished rooms to tenants on fixed income. He covers where self-storage sits after its boom and consolidation, and why he treats it like multifamily underwriting now. On technology, Tom is candid that he is still early but already getting leverage from AI. His current workflow is to go back and forth with Claude to build a long, specific prompt, then hand it to Manus for deep research on a market like Phoenix multifamily. He even has an AI clone at tomdunkel.ai that will answer your investing questions, as long as you do not bring up the Eagles. The lightning round digs into purpose beyond family, the best advice he ever got from a nine-figure investor, a job he probably should have turned down, and how he defines success now as an empty nester: geographic and time freedom, plus the room to give back through Tunnel to Towers and a scholarship he started for a friend lost to ALS. Find Tom at investwitheagle.com, grab his book The Wealth Builder's Playbook, or talk to his clone at tomdunkel.ai. Chapters 00:00 Don't let the tax tail wag the freedom dog 01:00 Meet Tom Dunkel and Eagle Capital Investments 03:00 Why true diversification lives outside the stock market 04:00 The SAFE Investing Method: Sponsor, Asset, Financials, Exit 08:00 Taxes and the lazy man's 1031 exchange 13:00 The Wealth Builder's Playbook and being the "who" 17:00 The buy box: mobile home parks, co-living, multifamily 22:00 Where self-storage sits after the boom 24:00 Using Claude and Manus to move faster 27:00 Lightning round: purpose, significance, and legacy 30:00 The best advice he ever got 33:00 A decision he would take back 34:00 On the nightstand: Invest Like a Billionaire 36:00 Defining success as an empty nester 38:00 Golf, a rock and roll cover band, and where to find Tom This week's book: Invest Like a Billionaire: Unlocking the Wealth Secrets of the Ultra-Rich by Bob Fraser and Ben Fraser https://www.amazon.com/dp/B0F3W2SNDS?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 ...
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    40 min
  • B-Class Property, A-Class Management: The Short-Term Rental Edge with Tim Hubbard

    B-Class Property, A-Class Management: The Short-Term Rental Edge with Tim Hubbard
    Jun 9 2026

    Short-term rentals are supposed to be the most hands-on asset class in real estate. Tim Hubbard runs hundreds of them across the U.S. and multiple countries—without ever being on the ground.

    Tim is the CEO and co-founder of Corzly, the virtual management company he built after 16 years of operating his own short-term rental portfolio from outside California, then outside the U.S. entirely. His team handles pricing, listings, guest communication, and back-end operations across Eastern Europe, South Africa, the Philippines, and South America—while the owner still controls the housekeepers and maintenance on the ground.

    In this episode, Tim and Ed get into why “a B-class property with A-class management beats an A-class property with B-class management,” why the urban short-term rental market is more durable than the vacation-rental crowd realizes, and what the data is actually telling operators about which markets to enter and which to avoid.

    What you’ll hear:

    • Why the “can’t be hands-on AND remote” constraint is the forcing function that built Corzly—and what it means for any operator stuck in their own business
    • The buy box: how Tim underwrites a short-term rental like an apartment building, what data sources actually matter, and the regulatory gotchas that kill deals
    • Why urban short-term rentals quietly outperform vacation markets—more reasons to stay, less seasonal volatility, and the medical-professional and conference angles most investors miss
    • The lightning round: under-budgeting renovations, Dennis Waitley’s “two choices” framing, and why education became Tim’s purpose once the portfolio could run itself

    Books Tim recommended:

    • Who Not How by Dan Sullivan and Dr. Benjamin Hardy—the framework for finding the right people to delegate to
    • The Slight Edge by Jeff Olson—Tim’s most-recommended book; the case for compounding small daily disciplines

    About Tim Hubbard: CEO and co-founder of Corzly. 16-year real estate operator. Host of Short Term Rental Riches, a six-year-old podcast covering virtual STR management, market selection, and the operational discipline behind scaled portfolios.

    Find Tim: corsley.com | Short Term Rental Riches podcast (all platforms + YouTube)

    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!
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    28 min
  • From X Games Gold to 3,300 Multifamily Units with Dan Brisse

    From X Games Gold to 3,300 Multifamily Units with Dan Brisse
    Jun 2 2026

    What does it take for a professional snowboarder, six X Games appearances, gold and silver medals, fifteen years on tour, to land in real estate? For Dan Brisse, the answer was watching the guys five and ten years ahead of him lose their houses, their cars, and worse.

    That was the wake-up call. While most of his peers spent every pay raise on the biggest house they could buy, Dan was reading books and buying apartments. By the time his snowboarding career ended, he had 70-some units already producing passive income.

    Today Dan co-leads Granite Towers Equity Group, a 3,300-unit multifamily portfolio focused on Dallas-Fort Worth, Nashville, and select Minnesota submarkets. The playbook is disciplined: newer assets (1985 and up), 140 to 300 units, $20 to $40 million purchase price, 95%+ occupancy submarkets with real pent-up demand. Eighty-twenty split with LPs. Sixty-five to seventy-five percent loan-to-value, fixed rate, non-recourse. CapEx raised liquid up front, so the bank cannot force a bad spend.

    What you'll hear:

    • The chairlift moment that reframed every financial decision Dan has made since
    • Why 78% of pro athletes are broke within three years of retirement and the side-hustle move he made to avoid joining them
    • The Cleburne, Texas case study: $6.75M acquisition, $2.1M LP raise, full-cycle returns
    • A second case study where interior upgrades and water conservation drove a 1.8x equity multiple in two years
    • Why Dan believes we are in a generational buying window with multifamily trading at 30-40% discounts versus 2021-22 peaks
    • His sharpest definition of wealth, and why "rich" and "wealthy" aren't the same thing

    Learn more about Granite Towers Equity Group: https://www.granitetowersequitygroup.com/contact-us

    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!
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    42 min
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