[6] After a chance encounter with Leon Bridges, Alexander's first break in the industry came when he was invited to hum and sing background vocals during the recording of his 2015 debut album Coming Home.

[9] In June 2022, Alexander co-wrote a new song with Bridges and Kevin Kaarl called "Summer Moon" inspired by a local Fort Worth coffee shop they frequented during the COVID pandemic.

[14] It was met with critical acclaim from NPR,[1] No Depression,[11] American Songwriter,[15] The Bluegrass Situation,[16] The Tennessean,[17] World Cafe,[13] and KCRW.

[18] He also made his television debut on CBS Saturday Morning, performing his singles "Today," "Tears Run Dry," and "Eye Can See" along with a feature interview.

[23] In addition to his own headline tours, Alexander has supported artists on the road such as Leon Bridges,[24] Charley Crockett,[25] Ani DiFranco,[24] Black Pumas,[26] Gary Clark Jr.,[27] The Lumineers,[28] and Mavis Staples[24] among others.