How to Build a 250+ Short-Term Rental Portfolio
Real lessons from vacation rental property managers who built portfolios of 250-900+ properties.
- Wednesday, October 28th
- 1:00 PM ET / 10:00 AM PT
- Zoom
Save your spot
Free on Zoom. Can't make it live? Register and we'll send you the replay.
- 900+units
James GilchristGilwest Collection, Founder & CEO - 270+units
Paul MyersSkyRun Vacation Rentals, Co-Owner and Operator - 280+units
Steven ChrobakMyrtle Beach Destinations, Owner
Growing to 250+ properties takes the right owners, the right properties, and a team ready to scale.
Join James Gilchrist of Gilwest Collection (900+ units), Paul Myers of SkyRun Vacation Rentals (270+ units), and Steven Chrobak of Myrtle Beach Destinations (280+ units) for a tactical webinar on building a 250+ unit portfolio.
Hear the strategies they used to win owners, expand their portfolios, and build systems that 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.
On the panel
- 900+ units
James Gilchrist
Gilwest Collection, Founder & CEO - 270+ units
Paul Myers
SkyRun Vacation Rentals, Co-Owner and OperatorPaul Myers is Co-Owner and Operator at SkyRun Vacation Rentals, where he helps lead a portfolio of 279 vacation rental properties. He brings a hands-on perspective on growing a property management business and managing the day-to-day demands of owners.
- 280+ units
Steven Chrobak
Myrtle Beach Destinations, OwnerDedicated military trained professional with 7-years of specialized aviation experience as a Pilot in the Remotely Piloted MQ-9 Aircraft (RPA). Extensive real estate experience including asset management, short-term rentals, long-term rentals, financials, and operations.
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.
Save your spot
Bring your questions and leave with ideas you can put to work. Save your spot today.
- Wednesday, October 28th
- 1:00 PM ET / 10:00 AM PT
- Zoom