A native of Los Angeles, Engelland, who also served as a ball boy for coach John Wooden's NCAA champions UCLA Bruins in 1975, began his basketball career at Pacific Palisades High School, leading Los Angeles in scoring as a senior in 1979.

Subsequently, he lettered four seasons at Duke University, scoring more than 1,000 points for coach Mike Krzyzewski's Blue Devils and being named the team's captain in his senior year.

In 1993, Engelland started his coaching career, introducing his basketball camps Chip Shots with the aim of helping players of all ages improve their shooting skills; two years later he founded the In-Net Corporation, strengthening his reputation as a clinician and advisor.

[2] He got his first job in the National Basketball Association (NBA) in the 1999–2000 season, serving as a shooting consultant for the Detroit Pistons.

Three years later, he signed with the Denver Nuggets as the director of player development, holding the position for two seasons.