This case study examines the opposing forces of innovation and legitimacy that play on new entrants into a market. New entrants in any market aim to provide an innovative product or solution in order to attract buyers. However, there are many situations where innovation may not be as valued as the new entrant expects due to various reasons, including a perceived lack of legitimacy. A case study involving a start-up software company providing a solution to the retail industry is examined, illustrating the strength of the requirement for legitimacy in order to be successful.