Olinda is a voluntary association, created with the aim to close and transform a large psychiatric hospital in the northern suburbs of Milan. Social entrepreneurship, welfare, and cultural activities have changed the area into a laboratory of social, urban, and human innovation for disadvantagedpeople as well as for citizens of the metropolitan area. Olinda started a social enterprise in an effort to combine services for the city with those for disadvantaged people. Olinda used conflicts within and outside the organization to advance public discourse and raise visibility regarding their decisions and actions. Olinda shows the role of outsiders with new ideas, skills, and social capital and how bringing different types of people together can generate new insights and developments. Sociability and cultural productions can be a turning point in building a shared interest in innovative action, especially in promoting intercultural activities with second generation migrants.