Business people in multinational environments must deal with a variety of situational barriers and cultural differences, such as time zones, languages, and common practice differences. Learning to accommodate these barriers and differences effectively often takes years of practice. Students who experience some of these barriers and become aware of some of the cultural differences while still in school have the advantage of beginning their practice early. Classroom to classroom videoconferencing (VC) provides an excellent discovery, or active, learning opportunity for business students to interact with, and learn more about, other's cultural similarities and differences. This article presents a case study that describes the videoconferencing interactions experienced by Japanese and U.S. undergraduate business students conducted in three successive years with three different sets of students on each side. In each year, students report learning a great deal about each other's cultures through the discovery learning process; at the same time, faculty learned that some types of discussion vehicles work better than others. Implications for how best to provide a cross-cultural experience via videoconferencing for students who will soon be in the international workforce are discussed.