Studstill attended Palm Beach Gardens Community High School, where he lettered in football, basketball, baseball and track.
He accepted a football scholarship from West Virginia University. As a redshirt freshman, he was the backup to quarterback Greg Jones. He also set a new school record with a 76-yard touchdown pass to James Jett against the University of Cincinnati.
In 1991, he was named the starting quarterback, throwing for 1,055 yards with 8 touchdowns and rushing for 307 yards with 2 touchdowns. His starting debut ended early when he suffered a shoulder strain early in the second quarter against the University of Pittsburgh. He returned to action against the University of South Carolina, throwing for 176 yards and rushing for 50 yards.
As a junior, he began sharing the starting position with transfer Jake Kelchner, both players were talented but with very different skill sets. Kelchner was the prototype pocket passer, while Studstill was an all-around athletic player. Head coach Don Nehlen never named a full-time starter, and kept it as a shared position throughout the tenure of both players. He passed for over 1,000 yards for the second consecutive season, posting 1,065 yards passing with 9 touchdowns, while rushing for 65 yards on 39 carries with 2 touchdowns. With a 20-point fourth quarter against the University of Maryland, he engineered the biggest comeback in school history, passing 16 out of 21 attempts for 166 yards and 3 touchdowns, with scoring drives of 78, 73 and 55 yards. With Kelchner out with an injury against the University of Miami, he played the entire game connecting 28 out of 41 attempts for 308 yards. Against Louisiana Tech University he had a 78-yard touchdown pass to Jett, breaking his own school record.
As a senior, he was part of the Mountaineers' undefeated 1993 team. While rotating with Kelchner, he completed 48 passes for 760 yards with 8 touchdowns, rushing for 145 yards on 25 carries with one touchdown. He saw his first action in the third game against the University of Missouri and had his best performance of the season against Rutgers University, completing on 11 of 16 attempts for a season-high 214 yards and 3 touchdowns.
West Virginia played the Florida Gators in the 1994 Sugar Bowl. The Mountaineers first drive went 80-yards and scored on a pass, then stopped the Gators on their first drive. The next Gator-drive almost went three-and-out, until a personal foul on Steve Perkins gave Florida the momentum. Kelchner was playing a good game, but Nehlen surprised many by putting Studstill in. On the Mountaineers first drive, Studstill threw an interception. Florida ran off with the game after that, winning 41–7.
He finished ranked sixth on the school's all-time list in career touchdown passes (27) and seventh in attempts (456) and passing yards (3,158).
Studstill was not considered a pro style quarterback entering the NFL because of his inaccuracy and was selected by the Dallas Cowboys in the sixth round (191st overall) of the 1994 NFL Draft to play defensive back. He spent most of his rookie season in the practice squad, until being activated in December and appearing in one game. He was cut on August 22, 1995.
In 1995, he signed with the Jacksonville Jaguars. He played two seasons and appeared in 15 games, before being released on August 19, 1997.
After being named head coach of Royal Palm Beach High School just one season earlier Studstill was fired in August 2009 just days before the start of training camp for the 2009-2010 season despite great success on the field in his inaugural campaign. He was dismissed partly because he and Principal Guarn Sims differed over the way Studstill handled finances and supervised his assistant coaches, though no one has alleged deliberate wrongdoing by Studstill.
In one season under Studstill Royal Palm Beach went 11-2 and reached the regional finals, and he was a finalist for the county's Lou Groza Coach of the Year award. Before being fired Studstill was given at least two opportunities to resign but declined. An official for the school was quoted as saying "In no way is it an attack on his personal or professional character. This is an isolated issue that directly deals with the direction of the football program." He will also retain his position at the school as a disciplinarian.
In 2010, he signed to be an assistant coach for Suncoast Community High School.