High school career
Ashley attended Bishop O'Dowd High School in Oakland, California before transferring to Findlay Prep in Henderson, Nevada for his senior season. He averaged 15.3 points and 6.8 rebounds per game as a senior, and led Findlay to a 32-1 record and an ESPN NHSI national title.
During the 2013–14 season Ashley helped lead the Wildcats to a 21-0 record to start the season before injuring his foot, sidelining him for the rest of the season. The season resulted in an Elite 8 appearance. As a junior, he was named Most Outstanding player of the Pac-12 tournament. Ashley averaged 12.2 points and 5.2 rebounds per game in helping Arizona return to the Elite Eight for the second straight year.
After going undrafted in the 2015 NBA draft, Ashley joined the Atlanta Hawks for the 2015 NBA Summer League. On July 27, 2015, he signed with the Dallas Mavericks. However, he was later waived by the Mavericks on October 24 after appearing in seven preseason games.
On October 31, 2015, Ashley signed with the Texas Legends as an affiliate player. On November 13, he made his professional debut in a 104–82 loss to the Austin Spurs, recording 13 points, three rebounds, three assists and one steal in 26 minutes. On January 29, 2016, he was named in the West All-Star team for the 2016 NBA D-League All-Star Game.