Globalization and technological advancements are the key prime factors that have led to the creation of competitive and complex market place. The aspirations and customer needs are changing at a phenomenal pace, creating immense challenge for the organizations. Subsequently, in the dynamic word effective brand positioning remains inevitable. Effective brand positioning assists the customers to know the real differences among the competing products, eventually leading to a better and justified selection of products by the end user. The following case study on Nano, considered as dream project of Mr. Ratan Tata, was envisioned with an objective to provide affordable mobility solutions to middle class Indians. The case focuses on how the initial strategies for launching and positioning Tata Nano as a Peoples Car backfired and how management recognized its shortcomings and mistakes that led to the wrong positioning of Tata Nano as Worlds Cheapest Car among the segment it was created for. And how finally after four years of its commercial launch, understanding the inevitability of positioning management repositioned Tata Nano as a Smart City Car by focusing on the youth to rejuvenate its image.