Entrepreneurship initiatives that could have an impact in rural areas are embedded in broader agricultural, rural development or structural policies at the European Union level. Nevertheless, there is a prevailing lack of rural strategies focused on entrepreneurship, especially in aging and depopulated EU rural regions. In this context, the need to have real experiences as an empirical contribution to the academic, political and professional spheres is identified. The purpose of this paper is to contribute to the current empirical research throughout a real experience and its capitalization. The paper portrays the design and implementation of a rural entrepreneurship strategy, in a very depopulated area, engaging civil society participation by adapting the ‘Working With People’ model to the idiosyncratic conditions of the context. The study then considers the main factors of this strategy by analyzing its application in a wider area in the province of Ávila, Spain. We find that rural entrepreneurship can be enriched by strategies designed and assessed by the beneficiaries from the early stages of formulation. This experience is supported by the ‘Fundación Tatiana Pérez de Guzmán el Bueno’, a non-profit institution that manages its legacy to achieve social goals in youth training, scientific research and environmental fields.