In the late 1990s, Northern Initiatives (NI), a regional economic development organization working in the Upper Peninsula region of Michigan, received one of the first Program Related Investments made by the Kellogg Foundation. In 2007 and 2009, the Center was invited to evaluate the impact of that investment on the evolution of the organization, specifically in terms of the development of their lending capacity, the critical role played by technical assistance/consulting as they worked with the region's entrepreneurs, and the increasingly active role played by NI in regional economic development. This report lays out the history of the organization, its development over time, and the challenges and opportunities it faced. The lessons learned highlighted here should be of value to other community and regional leaders who are undertaking similar efforts in their own unique parts of rural America.