Most people think the hard part of a short-term rental is buying it, but the real work starts the day a guest checks in.
In this episode of the Radical Hospitality Podcast, Zeke Freeman was with Tim Hubbard, founder and CEO of Corzly and host of the Short Term Rental Riches podcast. Tim got into real estate sixteen years ago chasing financial freedom, bought his first short-term rental in California eleven years ago, and slowly turned a remote operation into a business that now supports owners and managers across more than fifty cities. He runs it all from South Brazil with a team spread across the globe.
Tim and Zeke get into what it really takes to operate rentals well, where AI helps and where it still falls short, and the honest lessons from Tim's boutique hotel project in Medellin. It is a practical, grounded conversation about operations, technology, and building hospitality businesses that last.
What You'll Learn
- Learn how Tim structures a fully virtual team into four focused groups that keep operations running smoothly
- Discover the partnership model that lets owners keep their brand and their listings while handing off the day-to-day
- Understand exactly where AI helps in guest communication and where it still needs a human
- Explore the real numbers and setbacks behind a boutique hotel build in Colombia
- Hear why good reviews, not good marketing, decide which properties win in a crowded market
- Understand what to check before you ever invest in real estate in another country
If you own, manage, or dream about short-term rentals, this conversation is worth your time. Listen to the full episode with Tim Hubbard on the Radical Hospitality Podcast.
Connect with Tim Hubbard
LinkedIn: https://www.linkedin.com/in/tim-hubbard-str/
Website: https://corzly.com/
Zeke Freeman's new book, Radical Hospitality, is coming this September.
The book explores how to build cool stuff, serve a lot of people, and create lasting wealth, and how hospitality can be the vehicle for all three.
Join the waitlist: https://radicalhospitality.life/join
Grab the free Radical Hospitality Starter Kit → root-ad.com/starter
Connect with Zeke Freeman:
Instagram: @zekefreeman_rootarchitecture and @rootarchitecture
YouTube: @rootarchitecture
Facebook: @RootArchitectureandDevelopment
LinkedIn: Zeke Freeman
X/Twitter: @zfreemanroot
Ready to get started with your hospitality project?
https://root-ad.com/
Get in Touch: Stay connected with the Radical Hospitality podcast for more episodes exploring the intersection of architecture, design, and unforgettable guest experiences.
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