This article compares the work of fashion models and “new media workers” (those who work in the relatively new medium of the Internet as dot-com workers) in order to highlight the processes of entrepreneurial labor in culture industries. Based on interviews and participant-observation in New York City, we trace how entrepreneurial labor becomes intertwined with work identities in cultural industries both on and off the job. While workers are drawn to the autonomy, creativity and excitement that jobs in these media industries can provide, they have also come to accept as normal the high risks associated with this work. Diffused through media images, this normalization of risk serves as a model for how workers in other industries should behave under flexible employment conditions. Using interview data from within the fashion media and the dot-com world, we discuss eight forces that give rise to the phenomenon of entrepreneurial labor: the cultural quality of cool, creativity, autonomy, self-investment, compulsory networking, portfolio evaluations, international competition, and foreshortened careers. We also provide a model of what constitutes the hierarchy of “good work” in cultural industries, and we conclude with implications of what entrepreneurial labor means for theories of work.