An entrepreneur’s technological development will contribute to economic growth. There are two trends in historical studies on technique development in Japan: co-development with industry and government, represented by Sawai （2011）, and technological development by an individual, represented by Kiyokawa （1995） and Kan （2003）. This study examines the development trajectory that yielded Matsuda Ichiro’s （1894─1966） new shoemaking techniques to manufacture rubber-soled canvas and leather shoes. His method entails compressing vulcanized rubber into canvas or leather using heat. Matsuda recognized the entrepreneurial opportunity in manufacturing durable rubber-soled canvas shoes through his experience in manufacturing low-quality shoes using the Allianz machine. After recognizing the disadvantages of using adhesives to hold shoes together, Matsuda discovered direct vulcanization, which he assumed would enable the production of durable rubber-soled canvas shoes. Although that assumption was incorrect, this false belief led to the successful development of new production techniques. Furthermore, the simple realization that bamboo has stout roots, a detail that Matsuda stumbled upon by chance, was also a contributing factor. The wartime regulations that were established in 1937 forced shoemakers to restructure their businesses. Matsuda engaged in developing rubber-soled leather shoes, applying his technique for manufacturing rubber-soled canvas shoes that he refined with experience. Therefore, Matsuda’s technological development of rubber-soled leather shoes was stimulated by wartime regulations. The history of entrepreneurship will be apparent through the examination of various factors such as society, the economy, experiences of individuals and historical contexts.
