Intergenerational entrepreneurial initiatives are aimed at addressing the needs and opportunities of certain social groups and have the potential of becoming successful business projects. Moreover, they are a key to undertake sustainability practices that may represent a competitive advantage for the companies and an example to imitate when creating businesses. The objective of the study is to propose an intergenerational training methodology so that young people and seniors can create companies together, generating social cohesion and sustainable development in response to generational challenges. Intergenerational entrepreneurship seems to be a novel research area, especially when referring to developing methodologies of collaborative entrepreneurship projects. For this purpose, our literature review focuses on, first, the matching theories and experiences applied for intergenerational cooperation; then, literature about training methodologies for entrepreneurship is reviewed; finally, the main theories on training skills for entrepreneurship are approached. Focus groups were conducted as they serve as the main sources of data and are very appropriate for the generation of new ideas within a social context. In general, results show that, for achieving a successful intergenerational cooperation, some specific training is needed for both generations. This paper is a starting point for future research approaching intergenerational entrepreneurship, or entrepreneurial initiatives with singular characteristics, such as rural contexts or people with disabilities.