This paper focuses on small business entrepreneurialism in rural areas and its special conditions and needs. Our aim is to present examples of and suggestions for how to encourage firm start-ups and the continuation possibly also the development and growth of existing firms. The paper is based on three cases that illustrate (1) challenges in the support system in rural areas, (2) various forms of support that could be used in rural areas, and (3) expectations that are eligible to put upon support activities designed for rural areas. The following main conclusions were drawn: Firstly, we found that successful support of rural businesses requires a critical mass of regional entrepreneurs, firms, and support actors. Diversity is critical, and the various actors must be coordinated to carry out the desired measures effectively. We also found that expectations for growth and orientation of the firms must be realistic. Many times, broad support is more important than targeted support. Finally, we were able to show that a cross-boundary collaborative work culture that avoids both thought silos and business silos and places no value on prestige should pervade all areas of business support.