Caleb found his love for live productions his junior year of high school. Originally joining his high school theatre program for set design, he was quickly found as a fast learner with technology which moved him into the technical side of the theatre program. After Caleb graduated high school, he was asked to come back as technical director for the after school theatre program. Two years later after the former theatre director left the district, Caleb took the roll of director and directed the theatre program along with running sound and lights at various events around town. In 2013, Caleb collaborated on a community event with Brandon Styles and started his journey with The Brandon Styles Show as lead sound and lighting engineer.