The Blueprint for Building a 500+ Short-Term Rental Portfolio
Real lessons from vacation rental property managers who built portfolios of 540+ and 900+ units.
Join Cheyenne Hayes of Red Rock Companiees (540+ units) and James Girlisch of Gilwest Collection (900+ units) for a tactical webinar on building a 500+ unit portfolio.
Hear the real strategies these operators used to win owners, expand their portfolios, and build the systems to support growth, with practical examples from their own businesses.
You’ll walk away knowing:
- How to attract, win, and retain the right owners.
- How to choose properties that strengthen your portfolio.
- How to prepare your team and systems for your next stage of growth.
- How to increase profitability as you add more units.
Get an inside look at how these operators scaled beyond 500 units, and how you can apply their lessons to your own business. Sign up today.
About the speakers
Experienced entrepreneur with 20+ years of business ownership experience now working in the vacation rental industry here in Southern Utah. Skilled in customer service, operations, financial management, marketing, and team leadership, with years of teaching customer service workshops for different types of businesses. “Profits should be the oxygen to execute great hospitality.” My passion is people and I truly believe the best marketing you can ever do is to focus on solid operations at every turn of your business. Enneagram 3 and I’m all about those efficiencies and getting things done!
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James Gilchrist is an entrepreneur and the founder of Elevate Hospitality Partners, along with several other ventures in the hospitality space. Through his companies, he's built a reputation for scaling operations and delivering results across the properties he manages.

Darren Carter is the Head of Strategic Partnerships 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 baby daughter.
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