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    Bob Gillespie

    Executive Director of the REACH Commercial at Second Century Ventures

    Professional Background

    Bob Gillespie is a distinguished serial entrepreneur with over 25 years of extensive experience in technology, leadership, and operations. His entrepreneurial journey has been marked by a passion for innovation and a staunch belief in the importance of building exceptional teams. Throughout his career, Bob has founded multiple companies, each successfully attracting over $60 million in venture funding, culminating in an impressive combined enterprise value exceeding $150 million. This track record of success showcases his ability to not only conceptualize groundbreaking ideas but also to operationalize them into thriving businesses.

    In addition to founding his own companies, Bob has made significant contributions to the startup ecosystem as an advisor. He has worked extensively with over 200 companies participating in accelerator programs, providing mentorship, strategic guidance, and leveraging his vast network to help these companies secure new customers, establish partnerships, and attract vital venture funding. His role as a connector within the industry underscores his commitment to fostering growth and development among emerging businesses.

    Education and Achievements

    Bob Gillespie's educational background lays a strong foundation for his successful career in entrepreneurship. He holds an MBA from the prestigious University of Chicago Booth School of Business, where he concentrated on Entrepreneurship and Finance. This rigorous academic experience equipped him with a deep understanding of the financial markets and business strategy, critical elements for any successful entrepreneur. Additionally, Bob earned his Bachelor of Arts degree in Computer Science and English from Knox College, across which he honed both his technical and communication skills, ensuring he is well-prepared to tackle complex problems and articulate visionary ideas.

    As an executive director at Second Century Ventures, Bob plays a pivotal role in leading initiatives aimed at advancing the growth of real estate technology startups. Furthermore, his previous leadership positions, including his role as board member at Conference Software Solutions, Inc., and as executive director at Elmspring Accelerator underscore his influential standing within the venture capital and tech consulting landscape. His experiences as a partner at Anka Capital Management, LLC, and as co-founder and CEO at Swift Expos, LLC, highlight his diverse skill set and capacity to navigate various facets of business operations successfully.

    Bob also served as the co-founder, chairman, and CEO of InContext Solutions, where he led the company to become a prominent player in the realm of virtual shopping environments and analytics. His earlier roles, including engagement manager at Keane Worldzen and senior engagement manager at Navigant Consulting, showcase his extensive expertise in consulting and operations, providing a solid groundwork for his entrepreneurial initiatives.

    Personal Interests

    Outside of his professional endeavors, Bob Gillespie leads a fulfilling personal life rooted in family, sports, and exploration. A devoted father, he finds immense joy in coaching his son in basketball and baseball—a testament to his commitment to imparting valuable life skills and encouraging teamwork at a young age. Bob’s love for baseball is also reflected in his enthusiastic following of the sport.

    Moreover, Bob is an avid reader who enjoys delving into various genres, constantly seeking knowledge and inspiration. A passionate traveler with a goal to visit at least 100 countries in his lifetime, he embraces the opportunities for cultural exchange and personal growth that travel provides. Currently residing in the Albany Park neighborhood of Chicago, dubbed by many as ‘the greatest city in the world,’ he appreciates the vibrant community that surrounds him.

    Bob Gillespie’s impactful contributions to the world of entrepreneurship, along with his unyielding commitment to mentorship and community engagement, mark him as a leading figure in the technology and venture capital sectors. His journey reflects a blend of strategic thinking, operational excellence, and a genuine dedication to fostering talent in others, establishing him as a transformative force in the industry.

    Bob Gillespie
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    Location

    Greater Chicago Area