Gary is the driving force behind Roofstock's goal to power the future of real estate investing. Gary brings a valuable perspective on using technology to disrupt incumbents through his deep industry expertise leading various real estate, hospitality, and tech companies.

“Disrupting a historically fragmented segment is no small feat - but well worth doing. Critically challenging the way that things have been done and solving for it are pieces of the puzzle, but staying motivated and constantly thinking of ‘what's next' is how you truly succeed.”

Gary has a proven track record of starting and launching successful companies, having led two companies through IPOs: ZipRealty as CFO and Starwood Waypoint Residential Trust (now a part of Invitation Homes, the largest single-family rental home REIT in the United States) as co-CEO. In addition, Gary was instrumental in acquiring and integrating more than $800 million of resort properties for KSL Resorts and also served as CEO of Joie De Vivre Hospitality, then the second-largest boutique hotel management company in the United States.

Gary was named a 2019 Top 50 Fintech CEO by Financial Technology Report and HousingWire's 2018 HW Vanguard. He earned his BA in Economics from Northwestern and holds an MBA from Stanford, where he regularly participates as a guest speaker.