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Bob Youakim has had a varied and successful career. In 2000, they began their professional journey as an Instructor at APICS. Two years later, they moved on to become a Senior Auditor at Tribune Company. In 2007, they joined Wells Fargo Securities as an Investment Banking Vice President. In 2010, Bob founded and took on the role of Chairman of the Board and CEO at Passport. In 2017, they became a Board Director at CivicEye. In 2021, they joined Vita Mori Ventures as a General Partner, became a Board Director at Anduin, Athos Group, LLC, and Stratifyd, and became a Member Board of Trustees at The Fletcher School | The Rankin Institute.

Bob Youakim has an educational background in business and finance. Bob obtained a BS in Business Administration from Gies College of Business at the University of Illinois Urbana-Champaign between 1996 and 1999. Bob then went on to obtain an MBA from Northwestern University's Kellogg School of Management between 2005 and 2007. In addition, Bob Youakim holds certifications from ISACA, AICPA, APICS, and the Federal Aviation Administration.