Billy began to live an adventurous life, working on Mississippi riverboats as a stevedore and fireman. He was already strong and once had his fellow workers put a 500 pound bale of cotton on his back. Billy hauled the cotton into the boat and won a bet but cracked the gangplank. All of his life he was to perform amazing tasks and stand out as an individual and nonconformist.
He worked for a while in the coal mines of Missouri, learning the sad songs of the miners that he sang all of his life and passed on to his children. Billy became a plantation overseer and had two hundred slaves under him, yet he hated slavery and refused to fight in the Civil War. Because of his aversion to the slavery system, Billy left Missouri. He had been strongly affected by the cruelty he saw: for the rest of his life he reared back his 6'4", two hundred-pound frame every morning and bellowed out part of an old slave song, "I'm glad I'm free."
Billy fled Missouri and walked to Texas. He wore a leather blacksmith's apron with huge pockets for his tools and carried a saw on his shoulder. Along with all of this was his buffalo gun, "Old Betsy." He depended upon his prowess to survive and stopped in Indian villages for food. He also began to learn Indian dialects. Arriving in Texas, Billy camped along the Palo Pinto River until he built a log cabin and barn. This was in the wilderness area of Palo Pinto County where the nearest neighbor was one hundred miles away. He now had a wife and family and built a stockade around the house and barn for protection against the Indians.