[2] While at Westlake, Bolles was arrested and suspended for three games after he and four other players extensively vandalized rival Lehi High School's football field.

[4][5] Following his LDS Church mission, Bolles attended Snow College, where he played for the Badgers for two years before transferring to the University of Utah in 2016.

[6][7] Bolles earned NJCAA first-team All-America honors following his sophomore season at Snow College, starting all 11 games played.

He was named the 2015 Western State Football League Offensive Player of the Year in addition to picking up All-WSFL first-team honors.

Bolles was named to the All-Pac-12 Conference First-team in his only season with the University of Utah after opening all 13 games played (891 total snaps) at left tackle.

[2] Bolles earned all-rookie honors from the PFWA, and was the sixth rookie to open the season at left tackle for the Broncos in Week 1.

He was criticized publicly by general manager John Elway for repeatedly getting flagged for holding penalties, more than any other player in the NFL in his first three seasons in the league.

[25] On November 28, 2020, after improving greatly throughout the season, Bolles signed a four-year, $68 million contract extension with the Broncos.