When colonists from Scotland arrived in Sarasota December 1885, instead of a town they found one building and a trail. The Florida Mortgage and Investment Company had been misled about the area's development. After a winter so cold it snowed in Sarasota, most of the colonists left. The company directors went ahead with building plans and in 1886 sent J. Hamilton Gillespie, son of the company president, to help manage their investment.
Gillespie oversaw construction of the DeSoto Hotel, a boarding house, dock, houses, stores, and the clearing of three miles of streets. Steamer service began between Sarasota and Palma
Sola.
When no land sold in 1886 and only eight lots in 1887, the company directors ordered a voluntary liquidation of their holdings.
In 1902 Sarasota was incorporated as a town, and Gillespie was the first mayor. He held the post for six years. The town council brought electricity to the area by allowing Sarasota Ice, Fish, and Power Company to build a plant. In 1903, it gave permission for a telephone exchange. In 1908, the first property tax was set with $1,200 budgeted for lights.
The Florida Mortgage and Investment Company donated land for a school on Main Street, and Gillespie donated the lumber. The company gave land for the Rosemary Cemetery, a plot to the African Methodist Episcopal Church, and five acres for a black cemetery. The local Episcopal Church of the Redeemer began with a small chapel Gillespie built in his yard.
Gillespie promoted golf in Florida from the time he arrived, and would eventually lay out courses in Sarasota and other cities. After he sold his Sarasota interests to Owen Burns in 1910, he trained boys and young men in the Scottish Volunteer Force during World War I. He returned to Sarasota and was on the golf course when he had his fatal heart attack.