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Live Webinar
How to Scale Your STR Business to 100+ Units
Join this live panel with top STR operators from Stay Classy Homes, Atomic Stays, and The Cohost Company
Wednesday, August 27, 2025 at 11am - 12pm PST
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Join Live to Learn from Top Vacation Rental Operators
Want to scale your property management business without burning out or bleeding cash? Join this powerhouse panel of short-term rental operators as they break down the real strategies, systems, and mistakes behind growing from 30 to 300+ doors.
Whether you’re managing 10 or 75 properties, you’ll walk away with actionable insights to help you scale smarter and more profitably.
✅ The systems that broke—and what replaced them—when scaling past 50, 100, and 200 units.
✅ How to step out of daily operations and finally work on the business, not just in it.
✅ Real-world examples: when to hire, outsource, or automate.
✅ The biggest financial pitfalls that kill profits at scale (and how to avoid them).
✅ What your weekly schedule should look like at different growth stages.
✅ How leading operators think about owner relationships, trust accounting, and operational efficiency,
Who Should Attend?
- STR operators managing 10–100+ units
- COOs and ops leaders looking to optimize internal processes
- Founders ready to delegate and scale
- Anyone asking, “How do I grow without losing my sanity or profit margin?”
Sign up now (if you can't make it live, we'll send you the replay)
Bonus for Attendees
🎁 Exclusive Download: “Scaling Checklist: What to Systemize at 25, 50, and 100+ Units” (Delivered after the session)
Speakers
Moderator
Darren Carter is the Head of Demand Generation at Topkey, the leading platform for helping property managers automate their finances. Before joining Topkey, he spent over 13 years at various technology companies, specializing in fintech and startups, including founding and selling his own company in 2020. He lives in Boulder, CO, with his wife, puppy, and soon-to-be-born baby daughter.
Speaker
Matt grew up in a small town in Wisconsin and has lived in Spain, Boston, St. Maarten in the Caribbean, and now San Diego. He started investing remotely in multi-family and vacation rental properties in 2018 and then started Stay Classy Homes, a Vacation Rental Property Management business at the end of 2019. After persevering through some initial struggles during Covid, they have now built a 7 figure business, left their W-2 jobs, and plan to leverage their hospitality expertise to acquire hotels around the country.
Speaker
Kyle James is the founder of Atomic Stays, a leading vacation rental and boutique hospitality management company known for delivering elevated guest experiences through operational excellence and modern branding. A graduate of the University of Colorado’s Leeds School of Business, Kyle has built a career at the intersection of real estate, hospitality and technology.
Since launching Atomic Stays in 2021, Kyle has scaled the company to over 175 active listings across three markets. His diverse portfolio includes single-family homes, boutique hotels and bed & breakfasts that are each designed and operated with a focus on brand consistency, guest satisfaction and bottom-line performance.
As an investor, Kyle’s personal portfolio has delivered a 28.87% cash-on-cash return after all expenses, including debt service and third-party management. This underscores and is proof of his ability to source, underwrite and operate high-performing assets.
Patryk Swietek is a 27-year-old entrepreneur with a background in building tech companies since the age of 14 years old. Ever since getting into real estate at 24 years old, he's a thought leader in the STR industry teaching the co-hosting model with his own Amazon best seller book and online podcast.
He scaled from 5 of his own properties to managing over 100 signed properties in Joshua Tree in under 1 year. He has bought 3 STR co-hosting companies to become the #1 co-host in one of the most competitive vacation rental markets in the country. His company and homes have been featured on Netflix, Wall Street Journal, NY Times, Dwell, etc.
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