Who Was K-Holla?
Kyle Holloway started writing at 13 in Beloit, Wisconsin, to process the grief of losing his grandmother. By 15, he was DJing weddings and local bars in Phillips with his mom. In high school, an entire speech class laughed at his presentation on the power of rap lyrics, except for one who told him his delivery was legit. That single spark of validation was all it took. That same year, a classmate gave him the nickname "K-Holla." With a $10 microphone, a homemade pantyhose pop filter, and a free copy of Audacity, he launched his Myspace artist page and the rest was history.
After graduating from Phillips High School and then dropping out of UW-Stout in 2007, he moved back to Phillips and made cult classics like "Philly Get Up" and "In My Hoodie" before landing his first live gig at Mr. Heavy’s in Menomonie in 2010. From 2013 to 2019, Holla became a fixture in Eau Claire and Wisconsin’s Chippewa Valley scene, eventually opening for national acts like Alien Ant Farm, Kottonmouth Kings, and Tom MacDonald. In 2018, he launched hyFen8ed Entertainment LLC, only to watch it collapse under personal chaos, addiction, and debt.
What followed was a two-year run living out of his car across Colorado, Oregon, and Texas before finally returning to Phillips in 2022 to face reality in therapy. Refusing to rely on outside producers, he learned music theory and started cooking his own tracks under the moniker 9trippa Beats in 2022, picking up an acoustic guitar in 2023. After a toxic relationship led to his baptism and nearly a year of sobriety, Kyle had an epiphany on October 11, 2025: it was time to retire the masks. He integrated K-Holla the rapper and 9trippa the producer into one complete, authentic artist: Kyle Holloway. Closing the chapter with the H.A.P.P.Y. Again EP with Mr. Pizzy, Holla officially took his final bow.