In this paper, we are looking at the variegated nature of caste mediated occupational mobility from agriculture to business. More specifically, we are looking at regionally dominant landowning castes whose previous occupational affiliations were organized around agriculture, but due to significant historical and material circumstances, their occupational trajectories have transitioned into the realm of business and entrepreneurship. In the pursuit of this enquiry, we have chosen dominant landowning castes from Andhra Pradesh, who have attained occupational mobility and are traversing the domain of business and entrepreneurship. Using empirical evidence derived from case studies of four Indian family businesses, situated in particular caste, region, and occupational locations, our paper provides a framework that augments current understanding of processes and patterns of occupational mobility by juxtaposing the low and high levels of resource endowment (things that are of value in the production process) and social power (a relational capacity that enables certain social actors to asymmetrically influence the decisions of other actors in favor of the empowered actors' will, interests, and values). Our paper contributes to the larger literature on social and occupational mobilities in the following manner: (i) by explicating the financial and non-financial nature of resources that facilitate occupational mobility (ii) explicating the multidimensional and sociological nature of social power, and its visible components such as access to political power, social networks, institutional support, access to tacit knowledge (iii) Juxtaposing the levels of resource endowments with levels of social power to illustrate differential trajectories of occupational mobility.