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Jacob B. Cummins has held a variety of roles in their work experience. In 2010, they were a Day Camp Counselor for Westside YMCA. In 2011, they were a Summer Camp Counselor for Camp Takatoka and a Lead Ropes Instructor for Westside YMCA. In 2013, they were a Ropes Course Instructor for Callenge Quest Rogers State University and a Production Assistant for RSUtv. In 2016, they were a Production Assistant for KTUL, a Salesperson for AMERICAN EAGLE OUTFITTERS INC., and an Apprentice for Flightless Engineering. Finally, in 2017 they were a Security for Philbrook Museum of Art.

Jacob B. Cummins completed their education history with a Bachelor of Commerce (B.Com.) from Rogers State University in 2016, majoring in Radio and Television. Jacob B. previously obtained an Associate's degree from Northern Oklahoma College in 2013, majoring in Broadcast Journalism. Jacob B. began their education journey in 2006 at Mannford High School.