Social innovation is generally regarded as the capacity to respond to emerging social needs through new solutions and models without the primary aim of pursuing profit. Social enterprises, as organizations that apply business strategies to maximize improvements in human and environmental wellbeing, are widely engaged in social innovation. In Italy, social innovation appears to be a prerogative of social enterprises, especially of social cooperatives that are a type of non-profit social enterprise ruled by specific regulations. This article is a preliminary report on the specificities of social innovation and social entrepreneurship in Italy and in Latvia. The differences are useful to understand the difficulties that ex-soviet countries are encountering in shaking off their communist past and, at the same time, their potentiality for experimenting new forms of social cooperation.