The phenomenon of outsourcing largely arises from overlapping economic and social spaces. Morrison (2001) defines these “spaces” as the available “environmental resources” and “inherited entrepreneurial values and traditions” enabling business start-up. From the globalization point of view, the wave of innovations took two directions: (1) from the “center” (the United States, Europe and other first world economies) to the “periphery” (the third world countries); or (2) from the periphery to the center (Inda and Rosaldo 2002). This research looks at the interaction of these two waves by trying to understand the influences of business process outsourcing (BPO) entrepreneurship emerging from a third world country – the Philippines – to the first world economies. Examples include medical and legal transcription services, software and animation, and call centers from the Philippines servicing United States’ and European clients. More specifically, in this chapter, we probe the unique aspects of culture and society in the provider’s local environment, and study how the characteristics of the provider’s services are related to its socio-cultural environment, which is dynamically changing. Therefore, the two main objectives of this study are to show how location-related preferences can matter in the offshore outsourcing decisions of the clients, and to map the concordance between the socio-cultural dynamics of the BPO entrepreneurs’ local environment with the international clients’ expectations from their service providers.