In the twenty-first century, a hip hop music label becomes an indispensable source for learning: a young person's resource for information otherwise suppressed by industry regulation, federally censored, or not considered “news worthy” across corporate broadcast modes of distribution. This chapter, “Hip Hop 2.0,” examines how hip hop music label Web sites (Guerrillafunk.com and Slamjamz.com) provide an educational space where young people can interact, learn, and discuss “real world” problems via their commitments to popular culture. These internet music labels “sell” more than music. They broaden how cultural entrepreneurial production and innovative citizen initiatives can be re-interpreted by non-broadcast based media, while constituting a counter-public sphere for political activism and learning through networked digital media. Through these practices, we may witness the realization of the Internet's democratizing possibility at a time when these freedoms are not ensured, both off and online.