--- title: "How to Build a 250+ Short-Term Rental Portfolio" description: "Real lessons from vacation rental property managers who built portfolios of 250-900+ properties." canonical: "https://topkey.io/webinar/how-to-build-a-250-short-term-rental-portfolio" language: "en" --- [ Webinars ](https://topkey.io/webinars) Live webinar Zoom # 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 Gilchrist Gilwest Collection, Founder & CEO - 270+ units Paul Myers SkyRun Vacation Rentals, Co-Owner and Operator - 280+ units Steven Chrobak Myrtle Beach Destinations, Owner About the webinar ## 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: 1. How to attract, win, and retain the right owners. 2. How to choose properties that strengthen your portfolio. 3. How to prepare your team and systems for your next stage of growth. 4. How to increase profitability as you add more units. Who you’ll hear from ## On the panel - 900+ units ### James Gilchrist Gilwest Collection, Founder & CEO - 270+ units ### Paul Myers SkyRun Vacation Rentals, Co-Owner and Operator Paul 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, Owner Dedicated 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. Hosted by Darren Carter Topkey, Head of Strategic Partnerships 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. Wednesday, October 28th 1:00 PM ET / 10:00 AM PT Zoom [Save your spot](#register) Live webinar Zoom ## 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 With James Gilchrist, Paul Myers, Steven Chrobak and Darren Carter ## Disclosures \*Topkey is a financial technology company and is not an FDIC-insured bank. Banking services provided by Thread Bank, Member FDIC. FDIC Insurance available for funds on deposit through Thread Bank, Member FDIC. FDIC deposit insurance covers the failure of an insured bank. Certain conditions must be satisfied for pass-through deposit insurance coverage to apply. The Topkey Visa debit card is issued by Thread Bank, Member FDIC, pursuant to a license from Visa U.S.A. Inc. and may be used anywhere Visa cards are accepted. The Topkey Visa charge card is issued by Thread Bank, Member FDIC, pursuant to a license from Visa U.S.A. 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