In 1998 he founded Anticon Records, the first collectively owned indie Hip-Hop label in the United States. Since then, Sole has played over a thousand shows throughout the U.S., Canada, Europe, the Middle East and Japan. In 2009, Sole pulled his masters from anticon and has re-invented himself as a new kind of artist, business, and political entity. His music has been recently featured in major media outlets such as Rolling Stone, 2DopeBoyz, Pitchfork, MTV, Impose, Huffington Post, Spin, Alarm Press, All Hip-hop, Alternet and many more. Sole has released ten full-length studio albums and over a dozen mixtapes.

In 2009, together with award winning visual artist, Ravi Zupa, he published The Pyre, an illustrated epic poem exploring empire, radical philosophy, anti-capitalism, and collapse.  Throughout his career Sole has been known as one to push the limits in terms of genre and content and is widely heralded as a pioneer of avant garde & experimental rap music. In 2013, Sole launched "The Solecast", a podcast featuring long form interviews with academics, artists and activists. Sole’s activism reaches beyond the studio and stage into his everyday life where he is deeply involved material and logistical support to many projects that engage directly in the class struggle.