The entrepreneurial intentions that foster or reduce income inequality gaps between communities, especially in emerging markets, have been studied worldwide. Although informal entrepreneurial activities occur outside the formal activities regulated by the state, they account for at least 30% of the economic activities worldwide. This chapter delves into the entrepreneurial activity within the informal sector through the reflexive praxis lens to provide an in-depth understanding of the informal sector in the Global South. The experiences and narratives of entrepreneurial stories in this study were drawn from the bustling Evelin Street in Windhoek, the capital city. The study findings align with theoretical frameworks such as Pierre Bourdieu’s social and economic positioning and Sarasvathy’s theory of effectuation. By adopting an exploratory research design approach, this chapter offers an in-depth perspective of how resilience, strategic market positioning, and entrepreneurial mindset shape the narrative of informal businesses in the global south.