This paper studies the developments in Air Deccan, a start up in the Indian aviation industry and discusses the linkages among the aspirations of the entrepreneur, enterprise strategy and its sustenance in a competitive environment. It argues that the entrepreneur fails to sustain his/her enterprise and the aspirations if his strategic and operational choices and environmental responses to the choices create a resource or competence imbalance and constrain the entrepreneur. Based on its analysis and discussion, the paper delineates managerial themes like encyclopedic entrepreneurship, sustenance through co-sharing aspirations, managing first and fast mover advantages, dynamics of enterprise and its environment and competence management in start- ups.