Employing qualitative empirical data collected in Italy and England for a doctoral research on small-scale primary food producers in the alternative food economy, this chapter provides an interpretation of the peculiar nature of the entrepreneurialism that characterizes those small-scale farmers who entrust their economic reproduction (at least partially) to short, direct supply chains and alternative food networks (AFNs). The chapter summarizes the strategies implemented by farmers to ‘go alternative'as well as the subsequent transformation of growing and business practices that such a process entails, for then comparing the researcher's empirical results with four studies on farmers' entrepreneurialism. Issues of care, trust, change-orientedness, risk-taking, lifestyle, and autonomy are discussed, and farmers' entrepreneurial spirit is found to be cautious, due to the interplay of a traditional farming business orientation, a more pronounced relational disposition, and the characteristics and requirements of the alternative economy in which farmers are embedded.