Pierce Insurance Agency was founded by Harry Pierce, Sr in the 200 block of West Forsyth Street in 1927. Following in his footsteps, Harry Pierce, Jr joined the insurance agency in 1948., followed by his younger brother,  Tom Pierce in 1965. At this time, they were a captive agency, selling insurance products for one company. Decades later in 2003 Greg Pierce, a 3rd generation insurance agent, began working in the agency.  He saw into the independent insurance world, where there were no limitations to what he could offer. When Greg took over the business he did not want to have a franchise agency, where dozens of insurance companies are offered. Instead he only wanted the best companies to offer his clients. Each company they represent was specifically chosen by him.

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Original office loacted at 201 W. Forsyth St. in downtown Jacksonville in the 1930's