Bob Gillespie
Bob Gillespie
Executive Director
Second Century Ventures

Bob Gillespie is a serial entrepreneur with over 30 years of experience in technology, leadership, operations and finance. He believes that the ability to build great teams is the most important factor for success. Companies Bob has founded have gone on to raise over $70M in venture funding with an enterprise value of over $200M. In an advisory role, 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 $100M. 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. The Elmspring portfolio companies have gone on raise over $100M in venture capital after finishing the program. Previously, Bob was a Partner at Anka Capital Management, an accelerator focusing on emerging markets with a focus on Turkey. Bob has mentored over 100 Turkish early and growth stage companies on global market expansion and growth strategies. Many of those companies have gone on to international success with the portfolio companies operating in 41 countries. He was also the co-founder and CEO of Swift Expos which was acquired by Conference Software Solutions in 2013. The company created Software as a Solution (SaaS) products that make tradeshows, events and conferences easier to manage, providing tremendous return on investment (ROI) for both organizers and attendees. Bob co-founded InContext Solutions in 2009 to create an online virtual 3D platform to visualize point of sale environments for manufacturers and retailers of Consumer Packaged Goods. InContext Solutions was named One of America’s Most Promising Companies by Forbes, selected as one of the Rising Stars by the Illinois Technology Association, and selected from over 300 companies as the winner of the Up and Comer Award at the Chicago Innovation Awards. In its third year, InContext was recognized as the 9th fastest growing technology company in America by Lead411. InContext’s customers include many of the most recognized brands in the world. With his fun and engaging style, Bob is a sought after speaker at leadership, entrepreneurial and innovation conferences and events. He has spoken at The University of Chicago Booth School of Business, Northwestern University, DePaul University, The Accelerator Conference for Entrepreneurship, and the Seed11 Entrepreneurship and Venture Capital Conference. He has been interviewed on NBC-5 Chicago, CBS-2 Chicago, BBC-Discovery, CNBC, Bootstrapping in America, the Down and Dirty Craftsman Radio Show, Crain’s Chicago Business and Entrepreneur Magazine. He is a frequent speaker and educator at 1871 in Chicago, the #1 ranked North American Business Incubator by UBI. Bob has his MBA from the University of Chicago Booth School of Business with concentrations in Entrepreneurship and Finance. He is also an adjunct professor of Entrepreneurship at the Accredited Colleges of the Midwest. Bob loves baseball, is an avid reader, and a passionate traveler. He hopes to visit at least 100 countries in his lifetime. He lives in the Albany Park neighborhood of the greatest city in world.

My Sessions
Urban Resilience: Creating communities that bounce back
Panel discussion Main Stage