Rich received his BA in Trumpet Performance at San Francisco State University and studied with Joe Alessi while also performing at the San Francisco Conservatory of Music. Early on in his career he toured the U.S. as the Principal Soprano Bugle in the Santa Clara Vanguard Drum & Bugle Corps (84-87).
Just after discovering his vocal talents, he realized his long standing dream of touring and joined forces with Michelle Shocked , touring the U.S. and Europe. Currently, Armstrong is a touring multi-instrumentalist, mostly known for his effected and looped trumpet/flugel, congas, bongos, percussion, rhythm guitar, bass, and also sings lead and background vocals. On occasion, he’ll whip out the harmonica, mandolin, keyboards, DJ turntables, electric percussion pads, and even washboard. Whatever each song requires of him! He is featured on Shock’s "Dub Natural/Deep Natural" double album and also on two of the “Threesome” CDs “Don't Ask, Don't Tell, Mexican Standoff”. With her, he has toured every major city in the US, Canada, Europe, and Australia, and even was featured as a duo in the largest music festival in Tai Pei.