Cinninger was raised in Niles, Michigan where he says his parents' extensive record collection influenced his eclectic tastes in music. Cinninger began playing in many bands by the age of 12, ranging in styles from jazz fusion to country music. After spending some time in the Berklee School of Music, he took classical guitar lessons from Gerry Zubko in Roseland, South Bend, Indiana. In 1997, he started his own band, Ali Baba's Tahini and regularly played shows alongside of another local band, Umphrey's McGee. Cinninger chose to learn his chops by playing with others rather than attend a college musical curriculum, as many of his friends did. Eventually, Ali Baba's Tahini disbanded in 2000 and Cinninger accepted an offer to join as a full-time member of Umphrey's McGee in 2000. His first show as a member of the band was on September 1, 2000.