Jake made his debut as a country artist in 2014 at Larry Joe Taylor's Festival, where he played what would become his first single, "HIT THE ROAD." Jake and the band cut the song as a demo and it made it's way onto local radio stations in Jake's hometown of Corpus Christi, Texas, eventually reaching the top 30 and becoming one of the top 100 Texas radio songs of 2014. Increasingly successful singles followed, including "IGNORANT BLISS" (#16), and 4 consecutive #1 singles, "TAKE MY HAND" (#1 March 2016), "LONELY STREET" (#1 September 2016), " RESTLESS" (#1 September 2017), and "NOT TOO FAR TO REACH" (#1 February 2018).