Dick received his Bachelor of Arts degree in business administration and economics from Loras College in Dubuque, Iowa, in 1962, following service in the U.S. Army Reserve. His insurance career began as an underwriting trainee with Home Insurance Company of New York in Chicago. He later accepted a position as multiple lines underwriter for the Westfield Insurance Companies in their Ohio home office and was later promoted to field underwriter in northern Illinois, specializing in commercial and industrial accounts. In 1966, Dick returned to Dubuque, Iowa, and joined Friedman Insurance to begin the third generation in the family insurance agency organized by Henry Friedman in 1928. In 1984, Dick was awarded the CPCU (Chartered Property and Casualty Underwriter) designation by the American Institute of Property and Liability Underwriters.
He has served as chairman of the Mid-America Technical Conference, an organization representing 19 states and serving the American agency system as a forum for discussion on topics of property and casualty insurance coverages, rules, forms and other technical matters, to provide positive and proactive improvements in these areas.
In May of 1993, the Independent Insurance Agents of Iowa selected Dick as the recipient of their most prestigious award, H. H. Red Nelson, Agent of the Year. Dick served the Independent Insurance Agents of Iowa for many years and served as president of the organization from August 1998 through August 1999. During this time, Dick guided the merger of the Professional Insurance Agents of Iowa and the Independent Insurance Agents of Iowa, resulting in one of the leading independent agent trade associations in the country, representing over 8,000 insurance agents in Iowa.
Dick has always been passionate about education. He has encouraged many young insurance industry professionals to participate in insurance education and to seek professional designations. Dick established an educational incentive program at Friedman Insurance to encourage and reward professional development. He has acted as a mentor and leader, encouraging service and giving back to the industry and local communities. Dick currently serves on the board of trustees for Clark College in Dubuque, continuing to act as a role model and encouraging young people to seek higher education.