The central contribution of this article is to investigate Italian family capitalism and provide insights into the intricacies between families and family-run firms in one of these industrial districts in Lombardy. I argue that “familistic” relations have created favourable conditions for the development and the reproduction of small-scale industrialization in this region. Yet, some ambivalencies and contraddictions emerge in it as an effective arrangement to preserve the family firm through the next generations. Such contraddictions are also present in the entrepreneurial familism, as it contributes to reproduce a masculine structure of production, incorporating male authority, as well as specific obligations, consensus and conflict. I will contend that the current crisis of Italian family capitalism may have something to do with the contradictions within familism and its embedding properties.