Entrepreneurship holds transformative potential in economically disadvantaged regions, yet gendered disparities persist in access, performance, and outcomes. This study examines how political and psychological attributes shape entrepreneurial success in the urban contexts of Patna, Ranchi, and Lucknow, the capital cities of three economically disadvantaged North Indian states. Using a concurrent mixed-methods approach, the study analyzed survey data from 496 entrepreneurs and conducted 66 semi-structured interviews. Quantitative analysis revealed that government formal support, government informal support, narcissism, risk-taking, and passion were significant predictors of entrepreneurial success (ENS1 and ENS2). Gender and caste categories moderated these relationships. Male entrepreneurs showed stronger positive associations between success and both types of government support, reflecting their greater access to political networks and institutional resources. Psychological traits such as narcissism were more positively associated with male entrepreneurial outcomes, while passion and risk-taking influenced success across genders, though with varying intensity. Qualitative findings expanded on these insights by illustrating how men often navigate bureaucratic systems through informal networks and institutional ties, while women face compounded challenges due to limited outreach, structural exclusion, and a lack of visibility in formal recognition platforms. Women emphasized intrinsic motivation, ethical integrity, and emotional resilience, in contrast to men's focus on autonomy, strategic endurance, and external validation. Regionally, Patna showed infrastructural and training deficiencies, Ranchi revealed institutional invisibility for women, and Lucknow, despite a more developed entrepreneurial ecosystem, continued to exhibit gendered access barriers. These findings illustrate how entrepreneurial success is shaped by intersecting political access, psychological orientation, and social identity in low-resource urban contexts. Addressing these disparities requires intersectional policy reforms focused on inclusive mentorship, gender-responsive outreach, and integration of women into political and institutional ecosystems. Such strategies are essential for building equitable and sustainable entrepreneurial environments in under-resourced urban regions of India.