 Among his pursuits, Simmons was the president of the First National Bank of Kenosha, Northwest Telegraphy Company, and the Rock Island Railway Company.In 1859, he was the president of the Kenosha and Rockford Railway Company, while also working at the Wisconsin State Telegraph Company.Beginning at the age of 21, Simmons worked as a general store clerk for pioneer Seth Doan for $200 () per year.