In today’s global environment, a myriad of communication mechanisms enable cultures around the world to interact with one another and form complex interrelationships. The goal of this chapter is to illustrate an individual-based approach to understanding cultural similarities and differences in the borderless world. Within the context of Web communication, a typology of individual cultural value orientations is proposed. This conceptualization emphasizes the need for making distinctions first at the individual level, before group-level comparisons are meaningful, in order to grasp the complexity of today’s global culture. The empirical study reported here further demonstrates the usefulness of this approach by successfully identifying 16 groups among American Web users as postulated in the proposed typology. Future research should follow the implications provided in this chapter in order to broaden our thinking about the role of culture in a world of global communication.