Born Vanessa Mandekic in Aspach, Germany in 1992, Mai grew up in a musical family with a musician father. Encouraged to sing from a young age, she often performed with her father on-stage, and later appeared in school musicals. In her teens, she was also a member of the hip-hop dance troupe GettinCrazd. In 2012, she joined keyboardist Marc Fischer and guitarist Stefan Kinski as the lead singer in the fledgling pop group Wolkenfrei (Cloud Free). The group's debut, 2014's Endlos Verliebt (Endless Love), spawned several singles and reached number 18 in the album chart. Their follow-up, 2015's Wachgeküsst, fared even better, hitting the Top Ten and achieving gold certification status.