Many established professional sport leagues and teams possess ingrained conservative cultures that have poorly anticipated and capitalised on the emergence of new mobile technology services and digital marketplace developments – contrary to their media and marketing messages. Organisational rigidity makes sport professionals typically ill-prepared to respond to a relentless cycle of innovation in the mobile, digital, and telecommunications sectors. For instance, a digital business consultant and advertising executive who worked for major football clubs on two continents commented that the outcome is ‘very lame and very boring’ content and products that are ‘not disruptive [innovative] enough’ (Project Participant 3).1 These provocative statements were collected as part of a wide-ranging program of indepth interviews with industry informants. Generated by means of an international research project investigating the relationship between mobile media and sport, data from this project inform much of the analysis presented throughout this chapter.