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)

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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)

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