In their development over time, industrial companies go through repeated cycles of expansion and decline. Previous research into knowledge management and organisational learning has suggested that successful companies use the declining phases as learning processes in order to discard ineffective structures and processes so as to gain more competitiveness, enabling revitalised expansion. Failure to utilise the downturns for learning and development may lead to the demise of companies. Nevertheless, many companies have shown a remarkable ability to sustain their operations over long periods of time. The role of entrepreneurs in the inception and further development of companies has been shown. Nevertheless, the long-range role of individual entrepreneurs in the learning process of companies is largely unknown. Studying the impact of entrepreneurs on the long-term learning process of companies requires longitudinal studies. This paper reports a longitudinal study of three Sweden-based multinational companies, Atlas Copco, SKF and Volvo, over their life span which extends over periods of around or over hundred years of history. The purpose has been to explore the learning process of entrepreneurs in industrial companies. In order to capture the roles of individual entrepreneurs, the lives and deeds of three leading managers in the companies are studied, André Oscar Wallenberg at Atlas Copco, Sven Wingquist at SKF, and Pehr G. Gyllenhammar at Volvo. These managers have all made an important impact on their companies’ development. The methodology has been based on document stories. The results highlight the role of the individuals as entrepreneurs and they are related to theories of entrepreneurial learning as well as organisational learning and knowledge management. On this basis, a framework depicting the role of entrepreneurial learning in the long-term development of manufacturing companies is proposed.