Mr. Caldwell is a native of San Diego where he studied music at San Diego State University. He was an active music student with Marching Bands, Concert Bands, Jazz bands and Jazz combos. Mr. Caldwell paid for his entire college by teaching private lessons and performing in musicals throughout San Diego County. Through the SDSU ensembles he had opportunities to play with the likes of Chubby Checker, the Rockets, Chuck Findly, Charles McPherson and Eric Merinthol. He had performance opportunities such as Super Bowl XXIV, the Holiday Bowl and Charger Football Games. Mr. Caldwell was also involved in many leadership positions. He Served as Alto Section leader for Jazz Bands, Marching Band, and the Wind Symphony. Mr. Caldwell was president of the music service fraternity Kappa Kappa Psi. While president his chapter won "top 10" chapter of the nation award and was runner up to host the national convention. He also served on the Professional Studies and Fine Arts council where he earned "Best Newcomer Award". Mr. Caldwell also Composed and Directed the SDSU Wind Symphony his senior year in his original composition piece "A Reel Shade of Blue".

Mr. Caldwell completed his student teaching at Helix High School where he was not only directing but also the featured guest performer on the Alto Saxophone. Mr. Caldwell taught for three years at Montgomery Middle School in south San Diego where his students earned over 90 trophies for Marching Band and several superior ratings in concert band. He was recognized as "Teacher of the Year" in 1996. Mr. Caldwell has taught at Hillsdale Middle School since 1997. Mr. Caldwell teaches Full-time at Hillsdale as well as two Jazz Bands before school. Mr. Caldwell during his lunch and prep teaches the five elementary schools; Fuerte, Avocado, Vista Grande, Jamacha and Rancho Elementary. Because of this there are over 400 students in music in Rancho San Diego area school between 4th and 8th grade. This innovation and hard work has paid off with runner up to teacher of the year in 2002 for Cajon Valley School District, California Music Educators Association "Jazz Educator of the Year" in 2003, and "Teacher of the Year" for the Cajon Valley School District in 2005. He has been an active member of California Music Educators Association for the last 8 years. Through this organization he has been one of the founding fathers of the San Diego County Honor Band and is now the Honor Band Coordinator. He has also served as Instrumental Representative for San Diego Middle School music teachers for two years where he facilitated training of middle school music teachers for the CMEA Band Directors Conference at Point Loma Nazarene College. Mr. Caldwell has also been hired to judge the San Diego City Schools Middle School Band Festival in 2003, 2005, 2006. He has been hired to judge five years of the Grossmont High School District Honor Band auditions, and has just recently been approved to be a judge for band and orchestra festivals for Southern California School Band and Orchestra Association.