From Side Gig to 8-Figure Airbnb Business… and Private Equity Is Calling

We're looking for 10 serious Airbnb operators this month who want to scale past the plateau and build a business they could actually sell one day. If that's you, apply to the STR Secrets Mastermind here 👉 https://api.gostrmarketing.com/widget/form/VxOOgkW3BhQfHjNBpEOd Matt and Craig (this week's guests) came up through this exact community. They're now at 100 doors with private equity knocking. The right room changes everything. Spots are limited and we review every application. 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 🤝 Connect with Stay Classy Homes: 📸 Instagram: @stayclassyairbnbguys 💼 Partner with Stay Classy: partner@stayclassyhomes.com 📧 Reach Matt directly: matt@stayclassyhomes.com ⭐ If this episode helped, leave a rating on Apple Podcasts. It's the #1 way new hosts find the show. 📬 New episodes every Monday. #ShortTermRentals #AirbnbHost #VacationRentals #PropertyManagement #STRSecrets #PrivateEquity #AirbnbBusiness #CoHosting #VRMA #StayClassyHomes