Many rural areas in Japan now face serious problems, characterized by depopulation, a lack of young people, and a decline in community activities. The aim of this chapter is to articulate an entrepreneurial approach in Japan, with some leading examples such as constituting a possible new way for regional actors to revitalize declining rural areas through learning and collaboration. Public–private partnerships between the government and voluntary associations in an entrepreneurial approach are considered as new trends to reform social capital, and the question of how voluntary associations can be accountable to the government for an entrepreneurial program is addressed. Regional learning governance to promote an entrepreneurial approach is also discussed, and the characteristics of legitimacy capital, as a part of social capital in a business context, are examined. It is claimed that legitimacy capital plays an important role in effectively managing conflicts concerning regional development by promoting an alignment of the various interests and opinions of regional agents within a socially legitimate framework.