Gary has dedicated his career to building successful businesses across real estate, hospitality, and technology. After earning a BA in Economics from Northwestern, he pursued an MBA at Stanford, where he developed a passion for entrepreneurship and continues to serve as a guest lecturer.
Over the years, Gary has played pivotal roles in transformative ventures. At KSL Resorts, he led the acquisition and integration of over $800 million in resort properties. As CFO of pioneering online brokerage ZipRealty, he guided the company to a successful IPO in 2004. Later, as CEO of Joie de Vivre Hospitality, he oversaw the second-largest boutique hotel management company in the U.S.
Before co-founding Roofstock, Gary served as co-CEO of Starwood Waypoint Residential Trust, steering one of the largest single-family rental platforms in the country through its IPO. The company has since become part of Colony Starwood Homes.
Beyond his professional achievements, Gary enjoys skiing with his family, running alongside his golden retriever and office mascot, Bode, and tackling mountain biking trails—doing his best to avoid any broken bones along the way.
