Research on digital labor tends to fall into idealized, oppositional binaries that are judgmental rather than based on detailed analyses of the actual system or site. Our goal in this article is to provide a view on digital labor that is grounded less in speculation but in narratives from the producers of the platforms and content of the digital economy. To provide original perspectives on digital work we emphasize the agency of the producers and freelancers working at the global outsourcing firm Samasource and the cable television network Current TV. Our analyses of these two cases reveal important questions regarding 1) the values and organizational culture of firm founders and executives and 2) the mobility of freelance workers within the networks of digital labor. In conclusion we interrogate how wealth is distributed within the network. Across these questions, we introduce a research agenda that considers to bridge the ethical challenges of labor exploitation as well as the promises of social entrepreneurship in the digital economy.