The establishment of a solid understanding of regional economic development has proved to be highly elusive. Research efforts within this area have focused largely on major urban areas, yet this somewhat narrow focus means that economic development activities in smaller urban centers have not received the attention that they deserve. This article investigates regional economic development within a small city context through a survey‐based study of the entrepreneurial ecosystems operating in two small cities in the province of Manitoba. The results indicate that many currently accepted bases of regional business community expansion, such as government support and development of local suppliers, have limited utility within these cities. Concurrently, business leader survey responses from the two cities reveal a unique set of factors that drive economic development success in this nonmetropolitan case study, keyed by the pivotal role of a unique mix of nonlocal linkages, local cultural resources, and social connections in catalyzing local business expansion. These findings indicate that business community growth in the study cities proceeds from a distinctive template relative to larger centers, and suggest that increased research attention is necessary to elucidate the bases of business success in a more diverse selection of successful small cities.