Lacking a tradition of settling immigrants and the appropriate infrastructure to integrate them, small- and medium-sized cities often face the challenge of attracting and retaining immigrants. Using a mixed methods approach, this study compares the experiences of immigrant and non-immigrant entrepreneurs in a mid-sized Canadian city, Kelowna, British Columbia. A survey reveals different experiences between these two groups, with immigrants facing more challenges. In the absence of institutionally complete communities or strong ethnic economies, immigrants do not rely extensively on their own community resources, an element considered instrumental for immigrant business development in large cities. Compared to non-immigrants, immigrant entrepreneurs have a more optimistic outlook on doing business in Kelowna; this is encouraging for a city trying hard to attract immigrant investment. Key informants recommended transforming the city into a more welcoming community, establishing appropriate support infrastructure, and removing potential institutional offsets. This paper adds new theoretical insights to the literature on immigrant entrepreneurship; all socio-cultural, political-institutional, and economic-structural considerations are embedded in geography. The findings also have implications for growth strategies in small- and medium-sized cities.