Sherwood was co-founder of Carib Gems and Pressure Sounds, and founder of Hitrun Records as well as Green Tea Records and Soundboy Records. He is also the fourth member of industrial hip-hop outfit Tackhead, credited as "mixologist."
In 2003, Sherwood supported Blur at Wolverhampton Civic Hall. The same year, Sherwood released his first album as a solo artist, Never Trust a Hippy, which featured collaborations with various artists such as Sly & Robbie, Steven "Lenky" Marsden, Carlton "Bubblers" Ogilvie and Jazzwad.
In 2006 he released his second album Becoming a Cliché, again with numerous artists such as Lee "Scratch" Perry, the late Bim Sherman, Dennis Bovell, Little Roy, Lee "LSK" Kenny, Samia Farah, Raiz and Mark Stewart. A limited[vague] 2-disc version was released simultaneously with the second disc titled Dub Cliché.
On beginning a solo career, Sherwood stated, "I wanted to do some of my own writing and make something that was challenging for me... As a producer, it's my job to satisfy the artist foremost. I wanted to make something that was a little more aggressive and modern. I wanted to paint a picture that was contemporary, one that specifically showed where my brain was at. I've got to the point in my life where it's time for me to call all of the shots."