The STR game has changed—and most operators haven’t caught up.
In this episode, we break down what actually separates top-performing short-term rentals from the ones stuck in the middle. From design and amenities to operations, leadership, and systems—this is a real look at how elite STR businesses are built and sustained in hyper-competitive markets.
This isn’t theory. It’s what’s working right now.
Inside this episode:
- Why “good enough” STRs are getting crushed
- The amenity arms race (and how to win without wasting money)
- What guests notice that most hosts completely miss
- How ops and hospitality matter more than design long-term
- Why disciplined systems protect profit—even in down years
- The leadership mindset required to scale without chaos
If you want longevity in this industry, this episode is required listening.
00:06:15 – Becoming “The Guy” in a Hyper-Competitive STR Market
07:45 – Why Copying Competitors Is a Losing Strategy
09:15 – The New Minimum Standard for STR Design & Amenities
11:40 – Why Half-Upgraded Properties Always Underperform
18:50 – The Amenity Arms Race: What Actually Moves Revenue
20:00 – When Design Stops Mattering and Ops Take Over
26:10 – Building Teams and Systems That Don’t Break Under Stress
30:45 – Leadership Lessons from Military and STR Operations
34:05 – How Efficiency Protects Profit in Down Revenue Years
39:35 – The Long-Term STR Play: Scale, Discipline, and Longevity
Guest Bio:
Shane O’Connor is the CEO & Founder of Alchemy Real Estate & Alchemy Hosting. Alchemy is based in Tampa, FL, building a portfolio of Short-Term Rental assets primarily focused in Central Florida. By delivering vertically integrated, top-tier service from beginning to end in the investment process, Alchemy has grown from a single property (and single employee) to 11 properties & a team of four in less than a year. In that same time, Alchemy will have also delivered more than $3M in closed real estate deals for its clients.
By the end of 2022, it is Shane’s goal to have a blended Direct Ownership & Co Hosting portfolio of 30 properties centered in Florida, to then begin expanding to other markets. Shane is a graduate of the United States Naval Academy and served as an Officer in the U.S. Navy for 9 years. He received an M.S. Degree in Real Estate from the University of Florida. He runs the company with his brother, Captain Devin O’Connor, who is an active duty Marine Corps helicopter pilot in addition to being the Director of Operations for Alchemy.
Guest Link:
https://www.instagram.com/oc_dreams19/
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