Hensley's mother died when he was a baby and he was fostered by his grandmother for five years, until she died. Then he went through a series of foster families for two years, before going to live with his father aged seven. He ran away from home in 1888 to attend school (his father was opposed to white men's education), where he stayed until 1895.
He became a secular and spiritual leader of the Winnebago, Dakota and Ojibwa peoples, spreading the Peyote religion among them.