Gregg Brockway is a repeat entrepreneur with a track record of turning disruptive ideas into category-defining businesses. He co-founded Chairish in 2013 with his wife Anna, building it into the leading online marketplace for high-end home furnishings, art, and jewelry before its 2025 acquisition by Auction Technology Group.

Previously, Gregg co-founded and scaled multiple travel ventures, including TripIt (acquired by Concur), Hotwire (acquired by Expedia), and served as President of luxury travel provider Classic Vacations. Over 25+ years, he has combined product vision, team leadership, and sharp business acumen to consistently create beloved consumer brands and strong investor outcomes.

A graduate of Dartmouth College and Harvard Business School, Gregg began his career in private equity at Morgan Stanley and Hellman & Friedman. He lives in San Francisco with his family and remains passionate about scaling transformative ideas with lasting impact.