As a teenager Bowie floated lumber to market in the Avoyelles and Rapides parishes in Louisiana. He and his brother Rezin joined the army during the War of 1812. Their regiment was on its way to join Andrew Jackson at New Orleans when the war ended. After the war he and his brothers entered into the slave-trading business. During this time he developed a reputation as a deadly knife-fighter. He then got into land speculation. He bought large parcels of land and sold them whenever he could make a profit. Many of his land claims turned out to be fraudulent. He and his brothers moved to Arkansas where they soon were involved in new land speculation schemes.