A growing body of research has examined farmers’ increasing economic challenges in the United States and the new models adopted to help them increase profit, remain in business, and achieve agricultural sustainability. However, the entrepreneurial strategies that Western Corn (Zea mays) Belt farmers use to overcome economic challenges and achieve agricultural sustainability remain understudied. The model system used in this study was eastern South Dakota, and it examined the entrepreneurial aspirations of commodity crop producers using mail and online survey data collected in 2018. Using the diffusion of innovations framework, we investigated how innovation and entrepreneurialism spread among farmers; whether frequent training, building, and using social networks were essential to farmers’ business success; and how age, education level, and farm size relate to their entrepreneurial aspirations. We analyzed these three socio-demographic characteristics of farmers against their adoption of entrepreneurship and engagement in networking and training. Our results show that (1) farmers are looking for ways to adopt entrepreneurship; (2) education and farm size are positively related to the adoption of entrepreneurship; (3) age is negatively related to farmers’ adoption of entrepreneurship, and (4) a larger farm size is associated with farmers’ use of social networks and their participation in training. This study highlights the importance of providing farmers with entrepreneurial training, equipping them with necessary skills, maximizing their use of social networks and opportunities, and encouraging strategic planning and best management practices.