Bouldin attended ThunderRidge High School in Highlands Ranch, Colorado. In his senior year (2005–06), Bouldin averaged 25.4 ppg, 6.4 rpg and 4.8 assists per game. Bouldin was named the Colorado State Player of the Year as a senior.
Bouldin was named to the 2007 West Coast Conference All-Freshman team at Gonzaga. Following his initial campaign, he played for the silver medalist Team USA in the 2007 FIBA U19 World Championship in Novi Sad, Serbia.
Returning to Gonzaga, Bouldin led the Zags to three straight West Coast Conference titles, making first team All-Conference each time. Bouldin increased his scoring and rebounding averages in each of his four years and led Gonzaga to a Sweet 16 berth in the 2009 NCAA tournament.
Entering his senior year, Bouldin was named to the watch list for several major awards, including the John R. Wooden Award, the Naismith College Player of the Year, the Lowe's Senior CLASS Award and the Bob Cousy Award. After a strong individual season and in leading Gonzaga to a fourth straight WCC title, Bouldin was named the West Coast Conference Men's Basketball Player of the Year.
After going undrafted in the 2010 NBA draft, Bouldin joined the Chicago Bulls for the 2010 NBA Summer League. In October 2010, Bouldin signed for Iraklis Thessaloniki in the Greek League. He was released from the team, after tested positive in a WADA banned substance. He appeared in 10 games for the club averaging 9.7 points, 3.0 rebounds and 1.4 assists per game. In March 2011, he was acquired by the Tulsa 66ers. During the 2011–12 season, Bouldin played for KK Budućnost Podgorica of the Adriatic League.
In September 2012, Bouldin signed with Hapoel Tel Aviv of the Israeli Basketball Super League for whom he played only one game for before being released due to injury in October.
In November 2013, he was acquired by the Los Angeles D-Fenders. On December 19, 2013, he was waived by the D-Fenders. On December 27, he was acquired by the Delaware 87ers. On February 14, 2014, he was traded to the Fort Wayne Mad Ants. On April 26, 2014, the Mad Ants claimed their first D-League championship as they defeated the Santa Cruz Warriors 2 games to 0. Along with his first D-League championship, Bouldin received the Finals Co-MVP award along with teammate Ron Howard.
In July 2014, he joined the Orlando Magic for the 2014 NBA Summer League, but did not appear in a game for them. On March 3, 2015, he was reacquired by the Fort Wayne Mad Ants.
In July 2015, Bouldin joined the NBA D-League Select Team for the 2015 NBA Summer League and was selected by the Changwon LG Sakers with the 13th overall pick in the 2015 Korean Basketball League draft.
On December 18, 2016, Bouldin signed with Busan KT Sonicboom.