The case stories of the three African social enterprises portray how female leaders have fostered sustainable organisations through prioritising social, over economic and governance investments. Martha Letsoalo, a former domestic worker, founded the Heartfelt Project in South Africa, which now employs fifteen women, ships products all around the world and enriches the community of Makapanstad with its workshop, training and education centre. Victoria Nalongo Namusisi, daughter of a fisherman in rural Uganda, founded Bright Kids Uganda, a thriving care facility, school and community centre that educates vulnerable children, empowers victims of gender-based violence and distributes micro-loans to female entrepreneurs. Gertrude, abandoned in Lusaka, Zambia, founded Chikumbuso, a home of resilience and remembrance to educate children and offer women employment in a cooperative business. Each case documents the founding years of the social enterprise and outlines some of the shared women’s leadership approaches. The case dilemma focuses on why and how women start social enterprises in socially and economically difficult contexts.