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Transportation network companies (“TNCs”) such as Uber and Lyft manage ridesharing platforms that have increased efficiency and convenience for many passengers. These platforms, however, have also opened the door to many legal and regulatory issues pertaining to their business practices, employment structures, and transportation law and policy. This article provides a perspective on the economic, social, technical, and political aspects of TNCs in two steps, focusing on transportation and employment. First, it examines the future of TNCs in transportation, noting that TNCs could do more in terms of environmentalism to live up to the promise of the “sharing” economy. Second, the article analyzes the interaction of TNCs with labor and employment law. It proposes development of basic protections from the negative side of the TNCs management model, i.e. precarious labor and automatic management through algorithmic surveillance.