The recipient of a bachelor's degree in business and accounting from Healds Business College, Ronald Cupp founded Success Unlimited Accounting & Tax Service in 1981 and has continued to operate the Corte Madera, California-based firm ever since. Concurrently, Ronald Cupp has held a variety of other positions in the financial and commercial construction sectors.

Ronald Cupp worked as a controller for Phoenix Simpton Company, a San Francisco-based commercial contractor, early in his career and eventually purchased the company before selling it in 1987. He also founded Cupp Bros. Construction, through which he facilitated the construction of residential buildings as well as numerous commercial ones on behalf of companies such as Cushman Wakefield, Lurie Company, Banana Republic, and Bombay Company. He also offered up his company's services to complete several residential rebuilds following the Loma Prieta earthquake in 1989 and the Oakland firestorm of 1991. The company was in operation from 1981 to 2008, during which time Mr. Cupp supervised more than $30 million in construction projects.

Among Ronald Cupp’s diverse business interests was a chain of three Northern California hypnosis centers, which helped some 7,500 patients deal with personal behavior issues. The centers operated for seven years until he closed them upon his retirement in 2008.