Bob Gillespie

Executive Director, REACH Commercial at Second Century Ventures

Bob Gillespie is a serial entrepreneur with over 25 years of experience in technology, leadership, operations and finance. He has worked extensively with over 100 companies, with his mentorship and network connections leading to new customers, partnerships and venture funding for the participating companies. Companies he has worked with as an Executive Consultant have gone on raise over $150M. Bob is currently the Executive Director of REach Commercial after having served as the Executive Director of The Elmspring Accelerator, a venture accelerator that invests in technology startups who aim to disrupt the real estate and housing industry, with innovative solutions in housing, brokerage, smart home automation, multifamily, hospitality, construction and more. Bob has his MBA from the University of Chicago Booth School of Business with concentrations in Entrepreneurship, Strategy and Finance. Bob loves baseball, is an avid reader, and a passionate traveler. He is more than half way to his goal of visiting at least 100 countries in his lifetime. He works from the NAR Headquarters in Chicago, IL.

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  • Executive Director, REACH Commercial

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