Matt Floyd and Craig Gerulski started buying vacation rentals in 2018 to build side income while working their W-2 jobs. In 2020 they launched Stay Classy Homes to manage their own properties and a few arbitrage units in San Diego, and they ran it as a side gig for 3 years. Then a trip to STR Wealth in Nashville changed everything. They quit their jobs in 2023, went two years without paying themselves, and have since grown Stay Classy into an 8-figure business with 100+ properties under management across San Diego, Kauai, Nashville and Phoenix.

Now private equity groups are calling.

Fresh off VRMA, Matt and Craig sit down with Mike Sjogren to break down exactly how they rebuilt the business at every stage of growth, and how they’re thinking about a potential exit.

In this episode:

Hiring breakpoints: VAs at 20–40 properties, local staff at 60–80, and leadership after that
Their full team structure at 100+ properties
How many properties each property manager should oversee (and how to bundle them)
The $3,000/month VA fear that almost kept them stuck
How they’re vetting private equity offers: fit, incentives, tuck-ins and rolling equity
“Everybody exits”: the 5 D’s and why you should build to sell even if you never will
The real risks in STR: economic swings, regulation, and the OTAs owning your guest
Why your team problem is usually a leadership problem
How to recruit executives by selling your vision, not just the pay
Mentioned: VRMA, Steve Schwab (Casago), The Happiness Advantage, Igor Simkin (Monarch), Jason Cisneros, Coach Michael Burt, Breezeway, Guesty

 

Matt Floyd and Craig Gerulski’s Bio

Matt and Craig started buying vacation rentals in 2018 to create side income while working W-2 jobs and decided to start Stay Classy Homes in 2020 to manage their own properties and some arbitrages in San Diego where they live. They ran the business as a side-gig for 3 years until they went to STR Wealth in Nashville and decided to take it seriously. Since quitting their W-2 jobs in 2023, they have grown Stay Classy into an 8 figure business with over 100 properties under management in San Diego, Kauai, Nashville and Phoenix.

 

🤝 Connect with Stay Classy Homes:

📸 Instagram: @stayclassyairbnbguys

💼 Partner with Stay Classy: partner@stayclassyhomes.com

📧 Reach Matt directly: matt@stayclassyhomes.com