Nothing is known about Billie's early life. One day, he joined the pirate crew of the of the Wicked Wench. He participated in the Pirate Captain's raid on the Spanish island of Isla Tesoro. Billie and his mates successfully invaded the island and captured the main settlement, Puerto Dorado. After the battle, Billie was found drunk in the armory, carelessly letting off rounds of gun-fire. Billie How was leaning on a large crank, drunkenly singing "A Pirate's Life for Me".