In 1970, after eight years in the military, Kimsey bought a building in downtown Washington, D.C., renting out the top floor. On the ground floor, he built and opened a bar known as The Exchange. He "became successful and opened other bars in the 1970s." In May 1983, Kimsey was brought in as a manufacturing consultant for Control Video Corporation by his West Point friend
Frank Caufield, an investor in the company. Shortly thereafter, Control Video was reorganized as Quantum Computer Services, with co-founders Kimsey as CEO,
Marc Seriff as CTO, and Steve Case. Quantum Computer Services was later reorganized as AOL. Kimsey served as
CEO until 1995, when Steve Case took the helm. Kimsey was a key investor in, and a director of
Triple Canopy, a
private military contractor. ==Philanthropy==