My study engages with recent works on entrepreneurship and microfinance in the developing world as it seeks to understand youth's interactions with microfinance initiatives in a specific African context. Using the case of urban Dar es Salaam in Tanzania, I apply the theory of value to question the notion that 'entrepreneurship' can be separated from other aspects of cultural and social lives in the community. By providing business grants and entrepreneurship training, microfinance institutions assume that youth from poor backgrounds will also be able to start their own business, sustain it and succeed financially. However, this relationship is not well established and need to be further explored empirically and ethnographically. Through econometric analysis and ethnographic observation of three material sites, namely family, market, money and a project that provided a business grant to 52 secondary school graduates, I look at how youth, as potential entrepreneurs, in the context of limited access to formal education and employment in urban areas, make choices in regard to entrepreneurship investments, daily livelihoods, and future plans.