Ep 316 – From Side Gig to 8-Figure Airbnb Business… and Private Equity Is Calling
STRS Marketing2026-10-21T09:22:53-04:00Matt 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. [...]