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!

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!

JB Thibodeaux grew up in Acres Homes in Houston and is a third-generation carpenter and concrete specialist who turned that craft into a vertically-integrated real estate development business. His firms, J.B. Thibodeaux Homes & Properties, CCB Construction LLC, and CCB General Contractors LLC, have led over $100 million in projects across mass development, pocket development, and affordable housing infill. This year, the Houston market crowned him the "Duplex King."

In this episode, Ed and JB unpack a contrarian lesson the real estate education industry rarely teaches: the difference between the real estate hustle and the real estate business. Hustle gets you doors. Business gets you a sustainable enterprise. Most operators only ever learn the first one.

JB walks through the Houston duplex pricing math that vindicated his long conviction on the market, from "praying to get $350" on a 2,500 square foot duplex to selling at $479, almost $500,000. He explains his concept-to-keys pocket-development model, Houston's no-zoning-but-deed-restrictions quirk, the 60/40 build-to-sell vs. build-to-hold split for his client base, and why vertical integration (owning the GC) is a margin lever most flippers underestimate.

In this episode:

• Pocket development inside a major metro: the framework
• The duplex math that vindicated a Houston long-hold
• Houston's "no zoning" reality: where the leverage actually lives
• Why "the gurus teach you doors, not business"
• House hacking as the duplex exit strategy
• Generational construction knowledge as competitive moat
• Mayor Sylvester Turner naming February 20 "James 'JB' Thibodeaux Day" (2019)

If you're a flipper, wholesaler, or operator trying to build a business and not just a deal pipeline, this is the episode.

This week's book: The Miracle Morning by Hal Elrod

Guest: JB Thibodeaux, Founder & Managing Partner, J.B. Thibodeaux Homes & Properties

Website: jbthibodeaux.com

LinkedIn: linkedin.com/in/james-thibodeaux-8a98b51b7

Instagram: @jbthibodeauxhomes

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!

Dan Ihara has sold over $1 billion of real estate, moved 1,600+ units, and completed 400+ 1031 exchanges—without failing a single one.

And he built the whole thing around a niche almost no operator talks about: senior-care real estate.

In this episode, Dan and Ed get into the demographic inevitability that drives his business (“should we all be blessed to live long enough, we’re going to need some level of care”), why 1031 exchanges fail for everyone else but never for him, and his definition of success that has nothing to do with the billion-dollar number on his resumé.

What you’ll hear:

• The senior-care thesis: why aging boomers are an inevitability, not a trend, and the RE play sitting on top of it
• How Dan closed 400 1031 exchanges without a single failure—the process, the team, the discipline
• Why “success is doing what I want, when I want, with whom I want” is the only definition that matters once you have the numbers
• The conversation every operator should be having with their family—and almost none are

About Dan Ihara: 20-year real estate veteran. Billion-dollar producer. Built a specialty practice serving seniors transitioning out of long-held real estate, primarily through 1031 exchanges.

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!

Most multifamily operators treat internet as a tenant problem or a cost line they grumble about. Adam Bell, Founder and CEO of Internet Subway, says they're leaving real money on the table.

Adam runs a modern ISP focused exclusively on apartment communities. His company delivers fiber-to-the-unit (FTTU) in bulk to property owners, who pass it to residents as an included utility and capture the rent spread. Industry data shows 5 to 15% NOI uplift on well-executed bulk deployments. The math alone is worth the conversation.

But the bigger reframe is the one Ed pulls out of him halfway through: the fiber itself is an asset. Billions are flowing into fiber networks nationally. Property owners are in a rare position to own a portion of that infrastructure, a 30-year asset hiding in their own buildings.

In this episode:

• The bulk internet math on a value-add multifamily deal, and how an owner should actually underwrite it
• Why "managed WiFi" gets oversold and what to insist on instead
• Bulk internet versus experience, and why the difference matters more than the price
• Fiber as a 30-year asset class that scales in capacity, not maintenance
• The contrarian take from his industry piece "Managed Wi-Fi isn't all it's cracked up to be"

If you're an operator, syndicator, or value-add multifamily investor, this is the episode that turns a cost line into a revenue line and reframes the building itself as a fiber asset.

This week's recommended book: The Confident Mind by Nate Zinzer

Guest: Adam Bell, Founder and CEO, Internet Subway

Website: internetsubway.com

LinkedIn: linkedin.com/in/adamlloydb

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!

Brandon Cobb's business model is simple: take farmland, get it approved for housing, and sell it to national home builders like Lennar and DR Horton. The builders have no choice but to buy. They're publicly traded. Plan A is buy land and build houses. Plan B is buy more land and build more houses. There is no Plan C that doesn't involve buying land.

Brandon returns to Real Estate Underground to break down how HPG Capital creates new housing neighborhoods in Nashville, why he stopped building homes but kept developing land, and how he structures deals that pay investors 18% preferred returns with no personal guarantees.

What you'll learn:

- The three phases of land development and how to profit from each one without ever building a house
- How to de-risk a deal by lining up your buyer and getting city approval before spending real money
- Why "big puzzle pieces next to small puzzle pieces" on a GIS map is the buy signal
- How he gets 20% deposits from national builders, released day one, to fund development
- Why he ditched vertical integration after hitting $22 million in annual development
- The biggest mistake he made with strategic partners and how to avoid it
- His "Body, Being, Balance, Business" framework for measuring success

Books mentioned: The Surrender Experiment and The Untethered Soul by Michael Singer

Learn land development: learnlanddevelopment.com (free 8-hour course)
Invest with HPG Capital: hbgcapital.net/waitlist

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!

Ben Reinberg has done over $1 billion in commercial real estate transactions. He didn't get there chasing returns. He got there by treating CRE as what it actually is: a hard asset that produces cash flow, not a bet.

Ben is the Founder and CEO of Alliance CGC, where he's built one of the most respected portfolios in the country, with deep focus on net-leased properties and medical office buildings.

In this episode, Ben and Ed cover:

- Why medical office is recession-resistant in any market (the "human body never goes out of style" rule)
- The over-leverage mistake that taught Ben the real lesson of commercial real estate
- Cash flow, tax efficiency, and long-term security as the only three goals worth chasing
- How to navigate one of the most chaotic markets in decades
- The difference between treating real estate as a commodity vs. a hard asset
- What old-school CRE investors do that the new wave gets wrong

Connect with Ben: benreinberg.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.

🎧 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!

Clay Lehman spent 20 years in real estate, starting at Arthur Andersen, running the Ocala controller desk for Pulte Homes, and eventually building Lehman's Strategic Partners to help agents grow their businesses. He runs an AI Facebook group with members in 65 countries and now spends most of his time helping real estate pros turn AI from a shiny object into a revenue tool. If you're still using AI to write listing descriptions and calling it a day, this one will push your thinking.

In this episode you'll learn:
- Why Clay calls obscurity, not competition, the biggest threat to any real estate business
- How the "eliminate, automate, delegate" framework turns documented processes into leverage
- Which AI tools Clay actually uses daily, and how Gemini, Claude, and ChatGPT scored in his blind writing test
- How Ed built an AI voice agent that gets a lead on the phone in 45 seconds, across five languages
- Why the Harvard 391% rule makes speed-to-lead the single biggest edge in real estate today
- How solo operators and small teams can look and act like companies many times their size

Resources Mentioned: Google NotebookLM for deal prep and process documentation. Gamma for instant presentations. ylopo for lead nurture automation.

Takeaway: AI is a force multiplier, not a crutch. It levels the playing field on access, but experience and wisdom still do the heavy lifting. Use it as the spotter at the gym, not the guy lifting the weight.

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!