After helping form the Dayton Family with Bootleg, Shoestring played a primary role in the group's quick success within the Midwestern hardcore rap underground. Unfortunately, the group's quick success came to an end following their second album, F.B.I., when the group encountered numerous problems with the law.
Despite these obstacles, Shoestring went on to sign with Tommy Boy and released his solo debut, Representin' Till the World Ends, in 1999. Yet when the album didn't meet Tommy Boy's expectations, the Flint, MI, rapper soon found himself without a label deal. In early 2001, he signed with Detroit rapper Esham's Overcore label and released his second album, Cross Addicted, an album that found him returning to his street-level roots.