Robert E. Fleck graduated from Harvard Law School in 1958. He married and came back to Cleveland to work as a small business, tax, and trial lawyer with a small commercial law firm run by Homer Marshman, the then largest shareholder of the Cleveland Browns.

He had obtained his B.A. at Western Reserve University, (now Case Western Reserve), in 1953, magna cum laude. He was Phi Beta Kappa his Junior year, and received the Omicron Delta Kappa Key at graduation. He served two years in the U.S. Navy as the Radio Officer/Crypto Officer aboard the Aircraft Carrier U.S.S. Hornet.

In 1965 he had a chance encounter with Richard T. Reminger, his college classmate, and soon joined practice with him and his father. The firm incorporated in 1972 and he became vice-president, director, and legal counsel for the firm. He continued in those positions, working in many areas of defense trial work, and business, tax and estate planning practice until 1991, when he became 'of counsel'.