Founder of the Sears, Roebuck and Company department store franchise with partner Alvah Curtis Roebuck.
He worked in telegraphy and as a railroad station agent. He started out selling gold-filled pocket watches in Chicago rail stations.
He published his first Sears catalog in 1893, selling only watches. He was offering clothing, plows, silverware, bicycles, and athletic equipment by 1897.
He married Anna Lydia Meckstroth in June 1868.
He was a close childhood friend of Almanzo Wilder, future husband of Laura Ingalls Wilder.