The study proposes to illustrate elements of entrepreneurial culture in small and medium-sized businesses. The sample consists of 428 cottage industry businesses in the manufacturing sector along with the service sector with a cross-section of typical businesses to north eastern Italy (especially the province of Verona). The data collected via questionnaires sent out by mail (with questions regarding economic aspects, organization of work and management of human resources) reveal an interesting dynamic that informs the decisions entrepreneurs’ make in relation to the establishment of a company, investments and transition and the relationship between selected structural elements (size, turnover, choices made regarding innovation) and entrepreneurial choices.