Jason was born and raised in South Burlington, Vermont, and attended the South Burlington Schools. Throughout high school he was passionate about music. He was Principal trumpet for the All State Music Festival all four years of high school. He also participated in the New England Music Festival from 1998-2001, as Principal trumpet in 2000. Throughout middle school and high school, Jason studied with David Brubaker, from whom he attained the skills necessary to be succesful throughout his career. His parents, Cindy Matthews and Frank Whitcomb, have both dedicated their lives to teaching music, at South Burlington School District and Colchester/Burlington School District respectively, giving them 80 years experience between the two of them. Seeing the difference they made in every student they worked with, gave Jason the desire to pursue a degree in which he could have the same importance in students' lives. Music is such a powerful force, and he felt he had to use his talent to help change other peoples' lives.

Jason would attended the Crane School of Music in Potsdam, New York following his graduation in 2001. Jason studied with Dr. John Ellis for the four years he attended the Crane School of Music pursuing his Music Education Degree. He also fulfilled the requirements to receive a Performance Certificate, equivalent to being a Performance Major. From 2001-2005, Jason performed with the Symphonic Band, Concert Band, Wind Ensemble, and Crane Symphony Orchestra. He also performed in various chamber ensembles, one being a brass quintet. Brass Quintet's continue to be a passion of Jason's. Currently he can be heard with his brass quintet, InoraBrass, which consists of Chris Rivers (Trumpet), Lori Salimando-Porter (Trombone), Joy Worland (Horn), and Bill Keck (Tuba). While in Potsdam, Jason was honored to be asked to perform with the Orchestra of Northern New York as well as the Ottawa Symphony, with his teacher, Dr. John Ellis. With the Ottawa Symphony he performed Bruckner's Symphony No. 5 as second trumpet, as well as playing Assistant Principal Trumpet on Shostakovich's Symphony No. 5. It was during performances of Bruckner Symphony No. 5 and Shostakovich Symphony No. 5 with the Ottawa Symphony that Jason realized his passion for performance and bringing emotions to the audience in the way that only music can.

Following his graduation in 2005 with a BM in Music Education and a Performance Certificate, Jason went to the College-Conservatory of Music (CCM) - University of Cincinnati, in Cincinnati, Ohio, to work towards his Master's Degree in Trumpet Performance. While at CCM, Jason studiend with the renowned Principal Trumpet (ret.) of the Cincinnati Symphony Orchestra, Mr. Phillip Collins, as well as Mr. Alan Siebert, Dayton Philharmonic. Jason performed with the Wind Ensemble, as well as the two orchestras. He also performed with the West Virginia Symphony, 2nd trumpet in Gustav Mahler's Symphony No. 2 , as well as Verdi's Requiem. He then performed the same Symphony No. 2 at CCM, as Principal Trumpet. He also performed regularly with the Lima Symphony (Ohio) with friend and Prinpcal trumpet, Stephen Campbell. Throughout his two years at CCM, he performed in the Master's Graduate Brass Quintet. In 2007, Jason went to Lucca, Italy for five weeks through the Opera Music Festival of Lucca. He studied with Marie Speziale for five weeks, both individually as well as in a Brass Ensemble. After returning from Italy, Jason graduated from CCM with his Master's in Trumpet Performance in December of 2007.

After graduating, Jason remained in Cincinnati, supporting himself working various retail jobs in the Cincinnati area. After working for over a year in Ohio, he realized that his talents were going unused and knew that his home state of Vermont needed a trumpet specialist, as the other teacher had moved away. He saw this as an amazing opportunity to move back to the great state of Vermont and begin his professional music career. The opportunity to help advance the thriving music scene in the Burlington area, as well as be near his family was an opportunity he couldn't pass up. He decided to move back to Vermont and begin a playing career as well as start a trumpet studio of his own. Hoping to continue the tradition of high trumpet standards, that his former teacher David Brubaker had started and was extrememly succesful at, as well as combining what he learned over his college years, he moved back to his home state in 2009, striving to achieve this lofty goal.

Since moving back in 2009, Jason has performed with Lyric Theater, Vermont Contemporary Music Ensemble, St. Michaels Playhouse, Vermont Mozart Festival, Vermont Symphony, Opera Company of MIddlebury (OCM), Vermont Wind Symphony, Constitution Brass Quintet, VT Midi (Comp), Burlington High School Musicals, Harwood Union High School Musicals, Mad River Valley Chorale, South Burlington Community Chorus. He also performed with Fanfare (Vermont Symphony Orchestra Music in the schools group), a Vermont Symphony Orchestra Music in the schools brass trio that travels throughout the entire state education K-8 students about brass instruments through performance and demonstrations. He was joined by fellow InoraBrass members Lori and Joy.

In addition to performing regularly throughout the state, Jason has built a trumpet studio consisting of around 50 students a week. Jason began by driving to 30+ students' houses and schools, yet due to demand, has begun teaching at a central location. He teaches at Harwood Union High School once a week during the school year as well as being Adjunct Faculty at St. Michael's College. His students have gone on to pursue music at the Crane School of Music and UVM as well as non-music majors at St. Michaels College and Univeristy of Rochester to name a few. Jason's students regularly participate in the All State Music Festival, New England Music Festival, and the Vermont Youth Orchestra Association (VYOA). Under his guidance, Jason's students work toward the highest level of performance. This has consistently resulted in receiving the highest scores in the state and New England Area following their auditions and results in appointments as Principal trumpet in band and orchestra festivals and the VYOA.

​After filling in for Ray Vega at the University of Vermont while he was on sabbatical in 2017, Jason was asked to remain on faculty as the classical trumpet professor. Since taking over the classical trumpet duties at the University of Vermont, Jason has worked with not only music majors and minors, but also students in many other degree programs. Working with various levels of trumpet abilities has always been a desire, so this is a welcome addition to his studio.