Born in Toronto, Wabs Whitebird has lived his entire life there. Raised by a single mother, he grew up in the Esplanade, a community living in public housing and condominiums with a varied mix of working class people. He drew inspiration from dealers and hustlers living in the area as the foundation of his music. After witnessing many people struggling, both in and out of the native community, as well as his own friends and family, he decided to address these issues in his lyrics and music. He recorded his first two records, The Bootleg, and Success is the Best Revenge at CMP studios. His record label, Fluffy Records (coined by a nickname of his late father) released both independently. Without airplay or video play of any kind, he relied on his talent and word-of-mouth for exposure in the native and music community, leading to a nomination in the Canadian Aboriginal Music Awards category Best Rap or Hip Hop Album.