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Jeff Fitzsimmons has a long and varied work experience. Starting in 1975 as a Lemonade Proprieter for Jeff's Lemonade, they then became a Newspaper Delivery Boy for a Prominent Regional Newspaper in 1983. From 1988 to 1997, they worked as a Freelance Film Professional in Dallas and Seattle, working on music videos, commercials and feature films. In 1996, they became a Project Manager for Dillon Works Inc. and in 1997 they became a Writer for KOMO TV. In 2005, they were a Creative Director for Caffeine Communications and a Producer for the Milwaukee International Film Festival, where they pioneered the Collaborative Cinema program. From 2006 to 2015, they were a Co-founder and VP of Product Development for HarQen and a Co Founder for Custom Reality Services.

Jeff Fitzsimmons attended the University of Wisconsin-Eau Claire from 1988 to 1990, studying Marketing and Advertising. In 2001, they attended The Evergreen State College for one year, studying Photography and Film Production.