Family business in India has a rich history and heritage spanning multiple centuries. Though collectively family businesses have been progressively expanding their dominance over the Indian economy, individually family businesses have significantly varied experiences and fortunes. Some family businesses have retained their prominence and leadership across generations, a few have faded into oblivion and still others have emerged as new-generation family businesses. In this chapter the authors provide a brief historical account of the family businesses in India and trace the evolution of the leading family enterprises across different eras. They look back to look ahead in identifying some of the factors that explain the resilience of thriving multi-generational family businesses and the emergence of new-generation family businesses as well as the reasons for the decline of some of the erstwhile successful family ventures. The authors identify several challenges facing family businesses in India and present a set of normative guidelines for their sustainable future.