Life began in Philadelphia, Pennsylvania, but unfolded in Waconia, Minnesota, where her family regularly gathered around a piano or guitar to sing. In addition to traditional American music – the 1930 standard “On the Sunny Side of the Street” was a favorite duet for Jenn and her father – the senior Bostic turned her on the soulful sounds of Bonnie Raitt and the purity of Emmylou Harris.

Undeterred, Bostic performed several self-booked tours, and in 2012, released Jealous, which featured “Jealous of the Angels.” On a shoestring budget, she shot a video for the song and posted it on YouTube. Unknown to Jenn, a fan found the video and sent it to veteran DJ Simon Bates, who debuted the song on Smooth Radio. The response was enormous, and shortly after the song was playlisted at BBC Radio 2, Jenn performed the song on BBC Breakfast, and that day the song reached #1 on the iTunes singer/songwriter chart in the UK.
Jenn went on to be the first international independent artist to have three singles—“Jealous of the Angels,” “Not Yet” and “Missin’ a Man”—playlisted at Radio 2, the most listened-to radio station in Europe. That same year she won five International Country Music Association Awards including “Best Songwriter,” “Best Female Artist,” and “Overall Winner.”