In Italy, family businesses play a fundamental role. Approximately 40% of the top 100 Italian groups by turnover are controlled by the same family lineage and of these almost 90% have a family CEO, the highest value in Europe even if it is not much different from the others. In this context, the ability to generate knowledge management (KM), share it and make it become company assets is of strategic importance to remain competitive on the market also in light of the latest events linked to the pandemic. If in the past, the literature on KM was theoretically divided with an imbalance on the hard approach. Today a considerable weight concerns the soft approach, based on the management of skills and relationships between organizations and their environment as a means of generating new capabilities. Training and learning are ultimately fundamental processes for activating transformation and innovation actions and also for stimulating corporate creativity, which is increasingly fueled by establishing interconnections with different disciplinary fields, social and human experiences. The paper is aimed at verifying in the field what emerged from the Tagliacarne-Unioncamere (2023) on family businesses using a case study. In the Mosaic model it is required to specify four building blocks are always present in the business model of each company. Training and learning, in addition to improving the skills of the individual, represent a generative process for each person, which goes far beyond the acquisition of new knowledge. Only with strong attention to these issues and their corporate implications is it possible to create a context favorable to the birth of new ideas and the implementation of innovative projects where training and KM become the tool capable of improving people’s lives, the development of business and to advance society as a whole, creating a true learning society, based on solid entrepreneurial awareness.