In this article some of the critical aspects of Web 2.0 are mapped in relation to labor and the production of user generated content. For many years the Internet was considered an apt technology for subversion of capitalism by the Italian post-Marxists. What we have witnessed, however, is that the Internet functions as a double-edged sword; the infrastructure does foster democracy, participation, joy, creativity and sometimes creates zones of piracy. But, at the same time, it has become evident how this same infrastructure also enables companies easily to piggyback on user generated content. Different historical and contemporary examples are provided to map how the architecture of participation sometimes turns into an architecture of exploitation.