Jake has worked in higher education since 2002 as an instructor, career advisor, and administrator at a variety of colleges and universities around the U.S., including MIT, Boston University, Loyola Chicago, and UNLV. He received the MIT Infinite Mile Award for Innovation and Creativity for developing and facilitating improv comedy workshops to help with training and professional development.

He is a graduate of the Improv Asylum Training Center in the North End of Boston. With the last name "Livengood," this career path is quite fitting. Jake has a B.A. in Psychology from SIU Carbondale, a Master of Social Work from the University of Illinois at Urbana-Champaign and a Ph.D. in Higher Education Leadership from UNLV.