If you want lessons in reinventing your brand while keeping it relevant for decades, Shaggy is a smart place to start. Fresh off his tour with Sting, the two-time Grammy Award winning artist sits down with Bob to talk about why he risked going AWOL every week to record his first album, how he refreshes his brand while keeping it pure to his Jamaican roots, and why he always embraces the creative energy of the low periods.