The purpose of this research is to explore the business strategies of a firm seeking to develop and profitably market a mobile smartphone application to understand how small, digital entrepreneurships may build sustainable business models given substantial market barriers. Through a detailed examination of one firm’s process to try to commercialize their mobile app, we identify various business model decisions and marketing strategy approaches that hindered the company’s efforts. The case study describes two distinctly different business models adopted in succession, as well as the various adjustments the firm makes to its target market, distribution and pricing approach that led to their current strategy. This research looks closely at business-to-business-to-consumer distribution arrangement for mobile apps and in doing so challenges the rising positive bias that exists for the app store as the dominant actor in the mobile value chain. For practice, this paper suggests unanticipated hurdles small digital entrepreneurs may face if they rely heavily on mobile advertising and the app store to launch and sustain their business.