In the midst of the worst economic crisis since the Great Depression, there exists a deficit of compelling financial education curricula in urban schools that serve financially vulnerable working-class students. Part of a design-based research investigation aimed at creating culturally-relevant financial literacy learning environments, this study is a Discourse analysis of a discussion of personal finance on a web-based fan forum dedicated to hip hop music and culture. In this analysis the author claims that the discourse strategies and participant roles present in this discussion are an example of the organic production of what has been called a borderlands Discourse that bridges school-based knowledge of financial literacy with the youth culture of hip hop. The analysis presented here highlights the complex and overlapping ways that discursive hybridity in both representational practices and textual performances of identity figure importantly in the financial literacy practices of community participants. The author further contends that the understandings that emerge from this analysis can help design researchers attempt to "engineer" the values, identities and modes of interaction of hip hop discourse communities into academically-oriented learning environments.