Jim Fisk

From Wikipedia:
Fisk was born in the hamlet of Pownal, Vermont in the township of Bennington on April Fool's Day. After a brief period in school, he ran away in 1850 and joined Van Amberg's Mammoth Circus & Menagerie. Later, he became a hotel waiter, and finally adopted the business of his father, a peddler. He applied what he learned in the circus to his peddling and grew his father's business. He then became a salesman for Jordan Marsh, a Boston dry goods firm. A failure as a salesman, he was sent to Washington, D.C., in 1861 to sell textiles to the government. By his shrewd dealing in army contracts during the Civil War, and, by some accounts, cotton smuggling across enemy lines (in which he enlisted the help of his father), he accumulated considerable wealth, which he soon lost in speculation.