This chapter argues that community – specifically peer relations – serves as an important support that enables youth from marginalized backgrounds to further their education and earning, particularly when faced with social, economic, and gender inequalities. I draw on critical conceptualizations of social capital to analytically examine longitudinal data from a six-year evaluation of three youth livelihood programs in Kenya, Tanzania, and Uganda. Longitudinal interview data from a total of 230 youth reveal how peers are important sources of knowledge, advice, and financial support over time when faced with inequalities such as power differentials and gender discrimination in education and the labor market. By strategically drawing on their peers, youth are able to overcome inequalities in education and the workplace to further their livelihoods and achieve their goals.