#AMA - I built a 20+ home STR/Airbnb management company while working FT as a nurse
Hey everyone, I’m Jeremy Rosen, partner and San Antonio market lead at Five Star Vacation Home Rentals.
Quick background. I spent about a decade as an ICU nurse, including caring for open heart surgery patients. While I was still working those shifts, I started a short term rental management company in San Antonio from scratch. Over roughly three years we grew to 20+ properties. Then I made the call to merge with my mentor’s company to get more scale, better systems, and long term leverage. Today we manage 70+ homes across San Antonio and Austin.
Our focus is higher end homes, mostly 4+ bedrooms with strong amenities.
We run on data and use tools like PriceLabs, AirDNA, OwnerRez, and Hospitable to drive pricing, occupancy, and owner reporting.
Things I’m happy to talk about:
Starting a management company while working a demanding full time job
Pricing strategy and revenue management for large group homes
What owners should look for (and watch out for) in a property manager
Why I chose to merge instead of grow solo, and what that transition really looks like
Tech stack, systems, and building a team so you are not the bottleneck
The San Antonio and Austin STR markets right now
Ask me anything. No question is too basic, and I’ll give you straight answers, including the mistakes we made along the way.


