Gary left his co-CEO role at Starwood Waypoint Residential Trust (ticker: SWAY) in April of 2015 to co-found ROOFSTOCK (formerly DwellConnect), a technology-enabled Internet marketplace designed to dramatically improve transactional liquidity in the SFR sector. In 2009 he joined the board of single-family rental (SFR) pioneer Waypoint Homes and began investing in SFR, eventually joining full-time in 2011 to help raise the first significant institutional capital into the sector. In the fall of 2013 Gary helped orchestrate Waypoint’s merger with Starwood Capital Group, forming SWAY and taking the company public on the NYSE in early 2014.
Gary has spent the majority of his career in operationally-intensive and technology-driven companies with a significant real estate component to their businesses. Prior to joining Waypoint, Gary served as CEO of boutique hotel company Joie de Vivre Hospitality and award-winning solar technology start-up Greenvolts. Between 2001 and 2007 Gary was an operating executive with ZipRealty, where as its CFO he led the innovative Internet-based residential brokerage through its successful IPO before eventually being named its President. Gary also spent six years with KSL Resorts where he was instrumental in acquiring and integrating over $800 MM of resort properties. Earlier in his career, Gary worked for leading real estate industry firms LaSalle Partners (now Jones Lang LaSalle) and Security Capital Group.
Gary earned a BA in Economics from Northwestern University and an MBA from Stanford Graduate School of Business.