The potential of entrepreneurship to reduce poverty is closely tied to critical factors such as access to finance, training and education, networks and social capital, and supportive regulatory environments. Understanding and addressing these underlying issues through the lens of the Social Capital theory can help foster an entrepreneurial spirit in cities and mitigate poverty through business and community development. This paper explores the insights and standpoints of key stakeholders about poverty in Saint John and its impact on entrepreneurship. The study uses a quantitative method and analyzes data from surveys with stakeholders. The results show that social isolation, system inflexibility, individual issues, housing, and financial support programs are significant poverty challenges in Saint John, and these issues have implications for entrepreneurship. By integrating Social Capital Theory into policy initiatives, policymakers can enhance community resilience and empower vulnerable individuals. This application of social capital principles provides a holistic framework for designing effective poverty-reduction measures, offering transformative insights applicable not only to Saint John but also to diverse small cities. The study contributes a nuanced understanding of poverty’s impact on entrepreneurship, advocating for inclusive strategies that resonate with the social fabric of communities.