Entrepreneurship can create significant positive changes for economic development in rural areas. Specific to small farmers, who find it difficult to directly compete with large operations through conventional production in local and global marketplaces, the development of new feasible enterprises could be an important sustainable strategy. To understand the motivations of farm businesses, perceived survival risks, and entrepreneurship knowledge, we conducted a primary survey among small agricultural entrepreneurs (SAEs) in Tennessee. Based on the findings from our sample, SAEs are highly passionate and motivated in farming, the majority have business-related education or background (67% of the sampled SAEs) and consider themselves as self-employed (51% of sampled SAEs). Over half of our sampled SAEs developed 1 to 3 new enterprises in their farm or related businesses in the past 5 years while a few SAEs developed up to six new enterprises. However, we found that SAEs find their operation risky to continue and are challenged mainly by the shortage of skilled and reliable labor, finance and loans, and competitive markets. We also examined SAE’s level of understanding of different aspects of entrepreneurship and discussed the implications of our findings.