In recent years there has been an increase in the number of alternatives offered to the population in the context of urban mobility. Created and developed by private enterprise, services such as blablacar – a system of transportation based on offering rides to others and charging only part of the amount spent in the trip – and Uber – a kind of executive taxi service – have become a common choice of people when thinking about which mean of transportation is the worthiest to one’s specific need. However, the legality of this kind of service has been largely questioned, especially by the people who offer similar services, but in the traditional and previously exclusive way, and pay high monthly amounts of money to work, such as taxi drivers and van companies (in a few cities). On the other side, the new entrepreneurs who have recently joined this kind of business defend the service offered by them, arguing that the law charges companies with taxes and licenses, and they are considered independent contractors. In order to understand the legal and illegal aspects of such new business activities in the context of urban mobility, the current study extends the arguments presented by both sides of the dispute, and discusses their legal basis, according to Brazilian Law.