Jim Wylie followed in the footsteps of his father, John Wylie, who held the position of General Manager at Howick Mutual, who had followed after his father, James Wylie, one of the original directors for the Howick Mutual Insurance Company.
In April 1936 Jim Wylie, then a secretary of the Howick Mutual Fire Insurance, signed an agreement with Dominion of Canada, for the purpose of providing insurance for properties and automobiles that could not be insured with a Farm Mutual Company.
After an additional 37 years of service, Jim resigned from Howick Mutual in order to form Wylie Insurance Brokers in 1973. Jim operated out of the basement of his home, located at 2069 George St. Gorrie, Ontario.
In 1974 Fern Wylie resigned from her CIBC job in Fordwich, Ontario, and obtained her brokers license. As the business continued to grow a branch office was then opened in Harriston, Ontario, and additional staff was hired.
In 1982 son Stephen Wylie enrolled in the insurance course offered at Mohawk College in Hamilton, Ontario. Stephen Wylie then took his co-op in the family business, and upon graduation started full time in the Harriston office.
Eventually the basement office in the Wylie home was not large enough and in 1990 Wylie Insurance purchased the Howick Township office at 2057 Victoria St, Gorrie.