Wimsatt co-founded Rebuild the Dream (along with Natalie Foster and Van Jones), and served as its Partnerships and Political Director.
As a philanthropic consultant, he coined the phrase "Cool Rich Kids" (1999) referring to young progressive philanthropists associated with the organization Resource Generation.
[2][3][4][5] Wimsatt's first book was Bomb the Suburbs (1994), a collection of essays celebrating urban life and critiquing the suburban mindset.
Wimsatt released No More Prisons (1999), referencing urbanism and the prison-industrial complex, in conjunction with an underground hip-hop album on Raptivism Records.
[6] Wimsatt also edited the books Another World is Possible (2001) and Future 500: Youth Organizing and Activism in the United States (2003), Wimsatt co-edited How To Get Stupid White Men Out of Office (2004), a collection of stories from youth organizers around the world who won or swung elections.