This project is an international collaboration between music industry educators at higher education institutions in the United States, Australia, and New Zealand. The main goal of the project was to provide a case study and guidelines for collaborative pedagogical practices in higher education music programs in order to promote intercultural understanding, creativity, and social entrepreneurship. After the educators completed their initial planning work, the project was conducted in three phases. During the first phase, groups of songwriting students collaboratively wrote a set of songs that commented on a range of contemporary social issues. The second phase addressed the challenges encountered in successfully realizing international collaborations. In the final phase of the project, entrepreneurship and music industry students evaluated the original songs and incorporated a selection of these songs into student-driven collaborative social entrepreneurship projects. Finally, music industry students came up with promotional strategies to move the final successful project forward. The 38 Vol. 18, No. 1 (2018) following identifies and discusses the social, cultural, educational, and logistical issues we encountered during the project, and concludes with our recommendations on how to mitigate and avoid these difficulties in similar projects.