Ep 22 - From $60K Loss to 80 Units: Scaling with Acquisitions w/ Matt Floyd

Jay Ullrich sits down with Matt Floyd, co-founder of Stay Classy Homes, who started his short-term rental company in January 2020—literally the worst possible timing. After losing $60,000 in bookings in a single week when COVID hit, most would've walked away. Instead, Matt and his partner Craig hustled through the chaos and built something remarkable: 80 units across San Diego, Nashville, Phoenix, and Hawaii with 175 five-star Google reviews—not a single bad one.In just the past year, Matt tripled his portfolio from 25 to 80 units through strategic acquisitions, seller financing, and credit stacking. But here's what sets Stay Classy Homes apart: they cracked the code on delivering exceptional quality at scale. Matt reveals the exact acquisition strategy they used (including how to evaluate P&Ls and what red flags to avoid), why they focused on one core market instead of spreading thin, and how they built a boots-on-the-ground team that maintains hospitality standards across dozens of properties.They also dive into the power of community in the STR space, why Matt hosts weekly meetup calls for operators nationwide, and the looming threat of San Diego's proposed $5,000-per-bedroom annual tax on short-term rentals. This is a masterclass in surviving the impossible, scaling through acquisitions, and building a reputation that speaks for itself.Chapters(00:00) - Introduction: The Company That Started During COVID(04:16) - Meeting Through the STR Community(08:28) - Matt's Background: From Wisconsin to San Diego STR Operator(12:45) - The COVID Origin Story: Losing $60K in One Week(18:30) - Starting with Rental Arbitrage in 2020(23:15) - Hitting the Ceiling at 25 Units(28:40) - The Acquisition Strategy: Tripling in One Year(35:20) - Seller Financing & Credit Stacking for Acquisitions(42:10) - What to Look For (and Avoid) When Buying STR Companies(48:25) - Learning from Other Operators' P&Ls(52:30) - Why Focus on One Core Market for Quality(58:45) - Building a Boots-on-the-Ground Team(1:02:15) - 175 Five-Star Google Reviews: The Quality Secret(1:08:40) - The Power of STR Community & Weekly Meetups(1:12:55) - San Diego's Proposed $5K Per Bedroom Tax(1:16:30) - Family Travel & Why STRs Beat Hotels(1:19:11) - Closing ThoughtsConnect on Instagram⁠⁠⁠⁠⁠⁠⁠Jay Ullrich⁠ (@jay_ullrich_)⁠Matt Floyd⁠ (@mfloyd15)KeywordsShort-term rental, Airbnb, property management, Stay Classy Homes, Matt Floyd, COVID survival story, rental arbitrage, STR acquisitions, seller financing, credit stacking, scaling STR business, San Diego short-term rentals, quality management, Google reviews, hospitality at scale, STR community, meetup groups, Nashville STR, Phoenix STR, Hawaii STR, multifamily management, STR regulations, San Diego tax proposal, property acquisition strategy, STR operations, vacation rental management, entrepreneurship, leaving W2 job, business growth