In today’s world of wealth centered and technology drivenhuman population, the dawning era of social entrepreneurship acts as an inception agent in finding solutions to nearly all the pivotal and despairing social, environmental and cultural problems prevailing in the society. Throughout history researches carried out on identifying the underlying factors motivating and supporting the evolution and sustainability of social entrepreneurship venture creation, has led to various constructive results. In an attempt to understand the triggering effect these social and entrepreneurial drive factors possess upon an individual’s social entrepreneurship intentions; it was observed that the paradoxical effect of the coexistence of the social and entrepreneurial drive factors on the sustainability of social entrepreneurship has received less attention. Seeking to scrutinize that gap in the literature, this paper aims at identifying the level of inclination social entrepreneurs exhibit towards the social and entrepreneurial drive factors in the process of social entrepreneurship venture creation and the degree of contribution these factors have towards the sustainability of those social ventures from in-person, structured interviews with social entrepreneurs across various fields of operations in Tamil Nadu. This paper follows multivariate analysis techniques for testing the interdependency association amongst the measurement variables measured under entrepreneurial and social drive elements influencing social entrepreneurship. The empirical findings of the paper show that, the entrepreneurial drive factors receive relatively less importance in comparison to the social interests of the entrepreneur. Thus this paper concludes that paradoxical effect between the social and entrepreneurial drive factors have a negative impact on the sustainability of the social enterprises. The paper discussion traces on ways to offset that negative impact and improve sustainability of social enterprises.