The current global move to switch from analogue to digital terrestrial television technology has opened up an opportunity for the re-allocation of valuable radio spectrum resources. In one way, radio spectrum once used for analogue television will be completely cleared and in another way, digital terrestrial television technology geographically interleaves parts of radio spectrum to avoid interference between neighbouring TV base stations. This process liberalizes valuable TV radio spectrum, introducing the notion of digital dividend and leaving space for deploying new wireless networks services by small telecommunications players. In this context, this paper studies dynamic radio spectrum management policies and investigates new radio spectrum opportunities, as well as the economic potential and business strategies, towards leveraging entrepreneurship. Following this study, secondary markets for radio spectrum trading are examined and incentives of both primary and secondary telecommunications players are analyzed.