Wold was born in Oakland, California, USA. When he was four years old, his parents split up. His father played boogie-woogie piano and at five or six years old, Wold tried to learn but could not. At age eight, he learned to play the guitar (he later found out that it was blues) from K. C. Douglas, who worked at his grandfather's garage. Douglas wrote the song "Mercury Blues" and used to play with Tommy Johnson. Wold left home at 13 to avoid abuse at the hands of his stepfather, and lived rough and on the road in Tennessee, Mississippi and elsewhere, until 1973. He would travel long distances by hopping freight trains, looking for work as a farm labourer or in other seasonal jobs, often living as a hobo. At various times, Wold worked as a carnie, cowboy and a migrant worker.
Of this time he once said:
Hobos are people who move around looking for work, tramps are people who move around but don't look for work, and bums are people who don't move and don't work. I've been all three. Wikipedia