This paper provides an analysis of the discursive contradictions and narratives of labour within Hyr, a location-based freelance platform app that caters to the retail, hospitality, and restaurant sectors in Toronto and New York. The app provides companies with access to individuals with a variety of skills in these sectors and provides workers with access to contract jobs. The paper provides an analysis of Hyr’s promotional marketing, that targets urban “millennials,” and discusses how the platform exerts algorithmic and information control over its workers through their legal documentation and conditions of work within the platform. Situated within the “gig economy,” the paper also reviews current local policy proposals to alleviate the situation of gig workers in the Canadian context.