This paper is based on the South Asian culture, social institutions and entrepreneurship in particular to Sri Lankan entrepreneurship. Sri Lankan culture demonstrates various complex and unique behavioral patterns. Sri Lankan entrepreneurial culture can be identified to have evolved through two different routes. One can be traced to the origins of Sri Lankan civilization and the other to the western influence, originating from the Industrial Revolution, and imposed through colonization which systematically destroyed the indigenous feudal system. Moreover, the ideology of entrepreneurship training and education in Sri Lanka is exclusively western in origin and character. Observations of this research showed that the heart and the mind of such a system often do not work together and this conflict is apparent. This article focuses on disappointment of continuation of such knowledge by questioning, how such ideologies actually take root and bear fruit in the Sri Lankan setting which demonstrates complex and unique behavioral socio-cultural patterns. This article concludes that utilizing western ideologies could further worsen the effectiveness of entrepreneurship development in Sri Lanka.