Berry attended Hayward High School where he led his team to a 21-9 record his senior season. After graduating, Berry attended Cal State Monterey Bay for two years where he averaged 18.3 points and 4.1 rebounds per game and twice earned All-Conference First Team honors.
He was the named the team Most Valuable Player and an All-League First Team selection that season. Later he transferred to Weber State where, after seating for the 2011–2012 season per National Collegiate Athletic Association rules, he played and started 68 games for the Wildcats, ranking 15th in WSU history in career scoring with 1,160 career points and also fifth in career 3-point field goal percentage and 10th in career 3-pointers. In his two years at Weber state, he twice earned Big Sky All-Conference First Team honors and First Team All-District honors and was named the 2013-2014 Big Sky Most Valuable Player and the 2012-2013 Big Sky Newcomer of the Year.
After going undrafted in the 2014 National Basketball Association draft, Berry joined the Portland Trail Blazers for the 2014 National Basketball Association Summer League.
On July 25, 2014, he signed with PMS Torino for the 2014-2015 Serie A2 Gold season. However, in late January 2015, he was replaced on the roster by Ian Miller after appearing in 19 games.
He officially parted ways with Torino on March 3, 2015, and the following day, he was acquired by the Maine Red Claws of the National Basketball Association Development League. In July 2015, Berry joined the National Basketball Association Doctorate-League Select Team for the 2015 National Basketball Association Summer League.
In October 2015, he signed with the Changwon LG Sakers of the Korean Basketball League.
However, he managed just three games for Changwon, with his final game coming on November 8. He was released by the club and returned to the United States, where on November 17, he was reacquired by the Maine Red Claws. On March 4, 2016, he was traded to Raptors 905 in exchange for a 2016 third-round draft pick and the returning player rights to Abdul Gaddy.
Berry majored in Technical Sales at Weber State.
He played college basketball for the Weber State Wildcats where he was named Big Sky Conference Player of the Year in 2014. Three days later, he made his season debut for the Red Claws in a 112–93 win over Raptors 905, recording six points, four assists and one steal in 12 minutes. On March 11, he made his debut for Raptors 905 in a 102–98 win over the Iowa Energy, recording three rebounds and three assists in 21 minutes off the bench.
