This chapter investigates companies which contribute to better maintenance of aging and shrinking communities through business and entrepreneurship. Rural communities based on agriculture in developed countries suffer from aging and declining populations and structurally weak local economies, and require creative solutions to maintain the living standards and quality of life of the residents. Redefining and recreating local businesses are among these measures. To identify how businesses can stimulate local economies, two successful companies from Japan and Germany are compared. In both companies, the impact of entrepreneurial leadership is striking. The companies engage in using new combinations of local resources, including aging human capital, to stimulate residents to participate in their enterprises, and their efforts include business and social aspects.