Before Jake's senior year of high school, Keith Diebler accepted the head coaching position at Upper Sandusky High School, so Jake and Jon went with Keith to play basketball at Upper Sandusky.
[6] After his senior year, he committed to Valparaiso to play basketball under coach Homer Drew.
[7] During his junior season, the team finished 22–14 and went to the 2008 College Basketball Invitational and advanced to the second round with the help of Diebler.
That was where I felt like I wanted to be, but I had a heart change and here I am.”[9]“At the end of the day, the most influential people in my life has always been coaches.
"[9] Diebler was first hired by his former college coach Homer Drew to be a student assistant with the team for the 2009–10 season.
They made the NCAA tournament for the first time in 9 years, where they lost in the second round to 3-seed Michigan State[12] Diebler left Valparaiso before the 2013–14 season to accept a position as the video coordinator for Ohio State under head coach Thad Matta.
[13] He also trained professional basketball players like Aaron Craft, D'Angelo Russell, Evan Turner, Mike Conley, Jared Sullinger, Greg Oden, his brother Jon Diebler, Deshaun Thomas, Byron Mullins, and others.
[15] With the help of Diebler, the Commodores made the NCAA tournament, losing to Northwestern and finished with a 19–16 record.
He was the primary recruiter for 5–star point guard Darius Garland,[4] who committed to Vanderbilt on November 13, 2017.
[20] Holtmann was fired on February 14, 2024, and Diebler was named the interim head coach for the Buckeyes.
On March 17, Diebler was officially named Ohio State's head men's basketball coach.