Entrepreneurship is well established as a development strategy to facilitate youth empowerment in Africa. Existing scholarship on youth entrepreneurship, while informative, remains limited given its focus on either normative institutional structures or individual decision-making behaviors. Recent research offers a contextualist approach, featuring the dynamic relationship between individual behavior and structural context. Engaging and building upon a contextualist approach, this paper offers a place-based study of youth entrepreneurship in Botswana. The paper documents empirical findings revealing trends in youth circumstances and experiences, namely empowerment potential, financial strain and knowledge/skill gaps. It then explores the cultural, political and institutional contextual effects shaping youth entrepreneurship within the Young Farmers Fund (YFF). Drawing on elements of 'best practice,' the paper offers suggestions for enhancing practical entrepreneurship in Botswana through educational, technical and operational means. Although the paper contributes a case study of youth and entrepreneurship in Botswana, it also offers and demonstrates the conceptual framework of contextualism as a useful research tool for subsequent place-based studies.