Musicians work with, and around, various forms of technological media and resources. In today's professional environment, musicians face multifaceted work that may include teaching, performing, marketing, promoting, recording, or composing. The musician as entrepreneurial learner becomes a key focus for authenticity within their learning. Music educators, music professionals, and musicians of all ages need to navigate key career choices along their career paths which can be supported by authentic approaches to learning. This chapter explores how enterprise pedagogy and entrepreneurial pedagogy (i.e., authentic learning experiences) provide opportunities for students to reflect on, and prepare for, the likelihood of multiple jobs and roles in their upcoming career paths. Podcasting as an authentic learning tool is explored through the development of MusicWorks, a podcast series giving voice to the multiple career paths of industry and educational leaders in music.