In this essay, I will address some of the dynamics regarding the sharing economy model, giving an overview of the fundamental notions and disputes that emerged in the course of time. The sharing economy represent a complex and slippery terrain, on which are examing scholars of many disciplines, such as sociology and labour law and both the national and in-ternational legislator. If on one hand the sharing economy is believed to be an instrument to foster employment, on the other it leads to many controversies, regarding labour law, consumerism, competition, and the tax system. This essay will focus on the labour dimension, highlighting two cases: Uber, with reference to the mobilizations called by Unions and drivers at the international level, and the food delivery system in the Italian context.