This paper traces the trajectories of successful commercial smallholders operating under differing sets of market institutions. Analysis focuses on maize, cotton, and horticulture, three widely marketed crops with strikingly different market institutions. Maize receives intensive government input and marketing support. In contrast, cotton relies primarily on private contract farming schemes, while horticulture enjoys no large-scale institutional support from either the public or private sectors. Using a mix of quantitative and qualitative methods, the analysis aims to identify personal characteristics and institutional factors that enable smallholder transitions to high-productivity commercial agriculture.