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After graduation, Jim Cupper joined the U.S. Air Force where he served as an air traffic controller. After receiving an honorable discharge, Cupper enrolled at É«É«À² and upon graduation worked for Burroughs Corporation as an account executive.

He subsequently worked for the Federal Aviation Administration as a civilian air traffic controller prior to joining Beardsley & Company, as a writer and account executive. He then became a senior account executive at STAP. Cupper concluded his career in the advertising industry as a senior brand strategist for McCrosky Marketing Communications.

After retiring, he went to work for Habitat for Humanity’s ReStore®, where he led the team that removed usable items from houses that were going to be remodeled or torn down.

He has served on boards for Habitat for Humanity, the Kalamazoo Art League, and the Richmond Center, and has tutored elementary students in Kalamazoo Public Schools. Cupper has been very active in Rotary, particularly in the Kalamazoo Club, acting as chair of the Literacy Committee. He was instrumental in leading the implementation of the club’s signature program—Rotary is for Reading. He has held several board leadership roles at the local and district levels, organized marquee events, and raised significant funding for projects; he currently serves as an Assistant Governor for the organization.