The importance of a vibrant and innovative media sector in a democracy has been evident since Toqueville first observed media entrepreneurship in the United States in the 1830s. A major theme in entrepreneurship research is the entrepreneur’s ability to recognize and exploit opportunity. The notion that barriers-to-entry are a matter of perception and can be overcome by individuals with the entrepreneurial mindset runs in contrast to the view in economics research that barriers-to-entry are equal to all new entrants. There is some concern that today’s media marketplace is dominated by an oligopoly that deters new entry. However, recent research has shown media industries enjoy a high degree of entrepreneurship and the kind of turbulence thought to encourage innovation. In other words, entrepreneurship may flourish despite so-called big media hegemony. A simple illustration is pioneers in peer-casting: innovators harnessed peer-to-peer networks, blogging and podcasting to distribute their media where others did not recognize opportunity. This paper presents the results of a grounded theory approach to discovering prospects for new entrants in media and whether “the individual-opportunity nexus” has unique attributes in the case of media.