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Lif began the usual path for an independent rap artist: long nights spent honing his craft in the studio as well as testing his skill at open-mic sessions. He self-produced his first few independent records ("Elektro", "The Nothing", "Inhuman Capabilities", "Farmhand") while guest spots on notable peers' records like Jedi Mind Tricks' Violent By Design and collaborations with fellow Bostonians such as Akrobatik and 7L & Esoteric further solidified Lif's foothold in the underground movement. Lif made his first significant impact on the local airwaves with his song "Madness in a Cup" which was released by Boston based "Brick Records". Always thinking nationally and globally, Lif kept his targets set on working with a diverse but small collection of labels to project his sound. After working with The Beastie Boys' label "Grand Royal", he struck gold when he handed his debut EP "Enters the Colossus" (2000) to Definitive Jux CEO El-P (of Company Flow) just a couple months after the label was formed.