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Rima & Rick Dresher have owned Affiliated since 2008.  They have been life & business partners for almost 40 years.  They both began their insurance careers working part-time for Rick's father, Walter Dresher.  Mr. Dresher left the Toronto Police Service in 1966 to pursue a career in insurance with The Cooperators.  In 1969, he decided to go off on his own and started Dresher Insurance & Real Estate, working out of the basement of his home at in Etobicoke.

Rima & Rick were married in 1983.  After graduating from the University of Toronto that same year, Rick joined the firm full-time, and Rima followed suit in 1984 after graduating from Ryerson Polytechnical Institute. 1987 saw Rima & Rick take over from Mr. Dresher, who retired.  In 1996, Dresher Insurance Brokers merged with Chamney McWilliams Inc., to form CMD Insurance Services in Mississauga. After the formation of CMD Insurance, until their departure in 2008, Rima & Rick help grow the business into one of the 5 largest insurance firms in Mississauga, with over 35 employees.

However, the Affiliated story goes way farther back than Rima & Rick.  In 1903, William S. Davis left the famed "White Star" steam ship lines, where he worked as a purser, to start  W.S. Davis Real Estate & Insurance.  The business was located at 187-189 Lakeshore Rd. E. in Oakville.  As well as operating a very successful Oakville company, Mr. Davis also served terms as mayor of Oakville in 1908 and the again in 1919.

Upon his passing in 1942, Mr. Davis' third son, William E. (Bill) Davis, took over the operation of the business which was then known as W.S. Davis & Sons Real Estate and Insurance. And in 1978, the third generation took over when Bill retired and his son-in-law, Peter Zulauf, purchased the company. Peter had previously worked for Zurich Insurance in Switzerland and then Commercial Union in Canada.

In 1952, Ewart Carberry started E.F. Carberry Insurance, after first working as a high school teacher and then a life insurance agent.  The first office was located in the rear of Mr. Carberry's home in Oakville.  In 1972, Ewart's son, Michael, joined the family business for a short while, then decided to tour the world and later the rest of Canada.  He rejoined the firm in 1978, and ultimately took over management of the company from Ewart in 1983.

1985 marked the merger of Davis Insurance Agency with Carberry Insurance Agency to form Carberry-Davis Insurance Brokers, which is the company you see today.  The name was changed to Affiliated Insurance Management in 2000, but otherwise remained unchanged until Michael & Peter retired in 2008, selling the company to Rima & Rick.