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!