Young people are increasingly turning away from agriculture across many parts of the global South even where agriculture remains the backbone of livelihoods and the rural economy. Despite this youth-agriculture disconnect, many young people are exploring new pathways to agriculture and one of them is agricultural entrepreneurship. This paper focuses on youth entrepreneurship in agriculture to understand socio-economic conditions shaping diverse patterns of youth engagement in agri-enterprises. Empirical evidence for this paper draws on ethnographic studies conducted in rural parts of Nepal with in-depth interviews with youth (from the age range of 16-35 years) complemented by key informant interviews with local leaders and community workers who shared their experiences and local narratives of the links between youth and agriculture. This paper finds that youth engagement in agricultural enterprises is heavily mediated by economic status, caste, and gender in rural contexts. Given the chronic livelihood insecurity and the structural barriers rooted in class, caste, and gender, youth from underprivileged background were unable to successfully engage in agri-entrepreneurship despite their repeated attempts. This paper contributes to emerging scholarly dialogues on youth and agricultural entrepreneurship in Asia.