This chapter discusses a radio promotional strategy of a micro-firm during an extended period of disruptive technological change in the music industry. It explores one firm’s choice to alter its radio promotion strategy in response to shifting market forces. These changes persuaded the firm to ultimately abandon one strategy for another, which became feasible with the disintermediation of the value chain brought about through MP3 technology and the Internet, declining costs in music production and the use of the Internet as a way to educate managers on business practices. The case study provides a rich description of the influences on the strategic decision-making practice surrounding this choice including the use of heuristics, intuition and external advisors. The primary source data came from interviews by five employees of the micro-firm that were directly involved in the decision-making practice. Direct observation and note taking on company culture and employee interaction, analysis of artifacts in the form of company emails, websites, social media sites and magazines, and other items referenced in the interviews were also used as data sources.