Born in Mooresburg, in Montour County, Pennsylvania, Sholes moved to nearby Danville and worked there as an apprentice to a printer. After completing his apprenticeship, Sholes moved to Milwaukee, Wisconsin in 1837, and later to Southport, Wisconsin (present-day Kenosha). He became a newspaper publisher and Politician, serving in the Wisconsin State Senate from 1848 to 1849 as a Democrat, in the Wisconsin State Assembly from 1852 to 1853 as a Free Soiler, and again in the Senate as a Republican from 1856 to 1857. He was instrumental in the successful movement to abolish capital punishment in Wisconsin; his newspaper, The Kenosha Telegraph, reported on the trial of John McCaffary in 1851, and then in 1853 he led the campaign in the Wisconsin State Assembly. He was the younger brother of Charles Sholes (1816–1867), who was also a newspaper publisher and Politician who served in both houses of the Wisconsin State Legislature and as mayor of Kenosha.