This dissertation study explored women's labor in the beauty industries of the YouTube vlogosphere, specifically beauty video production on the ICON network, the beauty and lifestyle channel of YouTube entrepreneur Michelle Phan. Via a case study of ICON's YouTube creators and their video production, this dissertation explored female digital labor by interrogating gender, ethnicity, bodies, and power to address two interconnected elements situated particularly in the YouTube vlogosphere: beauty and entrepreneurship. The study's key research questions asked: In the transnational world of digital employment, what are the material and ideological complexities of beauty YouTubers' experiences? And how do YouTubers interpret their technical production, their beauty ideologies, their power, their authenticity, and the material outcomes of their production for themselves and others? Following an analysis of ICON as a company, interviews with its management and video creators, and its video products, the case study's findings reveal that while ICON recruits beauty creators to market on behalf of its retail partners, the creators see themselves as entrepreneurs who negotiate their own stances regarding their beauty ideals, user-generated content, (post)feminisms, and online authenticity.