Doug Chertok is a serial founder who co-founded StreetEasy, one of New York's most important real estate platforms later acquired by Zillow, before becoming a venture capital investor at Vast Ventures. His combination of 15 years operating real estate and hospitality businesses plus his experience as a proptech founder gives him deeper operating perspective than most VCs when evaluating early-stage consumer marketplaces and local services companies. Doug Chertok is a serial founder who co-founded StreetEasy, one of New York's most important real estate platforms later acquired by Zillow, before becoming a venture capital investor at Vast Ventures. His combination of 15 years operating real estate and hospitality businesses plus his experience as a proptech founder gives him deeper operating perspective than most VCs when evaluating early-stage consumer marketplaces and local services companies.