The Workshop on Cultural Entrepreneurship, organized by GoMad Concerti on June 10, 2021, included a meeting between a professional in the field and a group of young students. The meeting focused on explaining the various bureaucratic, administrative, production and promotion steps to go through in order to create a mural or any other type of cultural work related to street art. The cultural entrepreneur, outlined the peculiarities that characterize the connection between the art world and the business world. The circumstance of an increasingly rich presence of this form of entrepreneurship in Italy considering the induced tourism it manages to generate, has caused the increase in competitiveness and the decrease in available financial resources. Therefore, the processes that are constantly supported by a cultural enterprise so that it can produce induced income in an economically and financially sustainable way were explored. The entrepreneur explained the modus operandi and the various production steps that precede the creation of a work of street art, starting with the agreement with the artist, continuing with the choice of the concept, relations with the public administration, and the application for permits regarding landscape constraints to the superintendency that holds control. The various circumstances concerning relations with the local area, civil society, and all the actors involved during the creation of this type of artistic work were explained in detail. Finally, a model was outlined on everything related to sustainability and budgeting and social, print, and institutional communication.