Kaplan graduated from the University of Michigan with a BA in Philosophy, and is also an alumnus of Pi Kappa Phi fraternity.
[1] Kaplan began his career as an investment banker in New York City after his graduation from the University of Michigan, and worked in the industry for three years at Furman Selz.
In 2002, Kaplan started Redbox, testing a variety of different product kiosks, including DVD rental, in a handful of McDonald's restaurants and other miscellaneous locations in Washington DC.
[8] Following his time at Coinstar, he co-founded Modjule LLC, a private investment firm focused on kiosks and small footprint retail.
He also sat on the boards of Chicagoland Entrepreneurial Center, Enova, In Context Solutions, and Network for Teaching Entrepreneurship.