A graduate of the UNIVERSITY OF DUBUQUE with majors in speech and communications, Olsen had no formal art training. He found many of his first brushes discarded by sign painters at Frank Hardie Advertising Inc. where he worked as a janitor during college.
Olsen joined the DUBUQUE COMMUNITY SCHOOL DISTRICT as its Director of Web Development and Public Affairs after a distinguished career in corporate communications. At the JOHN DEERE DUBUQUE WORKS, he produced the award winning company publication, Tracks. Olsen worked in advertising and multimedia design for Frank Hardie Advertising and then for government contractor NCS (now NCS Pearson), helping federal and state government agencies design and build websites. Beginning in 2000 working in education, Gary programmed and managed a completely automated Cable Television Channel, Mediacom 19, which played in the greater Dubuque Tri-State market.
Channel 19, the exclusive domain of the Dubuque Community School District, was launched as a cooperative venture between Dubuque Schools and Mediacom Cable. Programs originated in Dubuque schools and played statewide. Olsen produced the national award winning Kids in the Kitchen, and Garden Organic. He also developed a medical show for children called Doctor! Doctor! and a music education show called The Maestro and Me! In 2008 High School House, a show in which a dozen high school students and a professional contractor and interior designer build a $300,000 house, was in its third season. Olsen also produced Kids & Creatures, Reality Math, Designer's Club (a show about interior decorating), Mudd Puppies! and countless documentaries such as Dubuque, An All-America City.
Olsen won many awards for film making, documentary work, and graphic arts. Kids in the Kitchen, won the cable television industry's most prestigious award, the Beacon, for best series television show in its first year on the air. The show was unique because the kids cooked on the show with nutritional ingredients they purchased in the store with the chef. In January 2008, Olsen and his cast for Kids in the Kitchen were producing their third season in the new kitchen set constructed in 2007 by Hy-Vee, the host sponsor of the show. The kitchen was a state-of-the art instructional cooking facility built to Olsen’s specifications. For two consecutive years, 2006 and 2007, Olsen was named among the top 41 best cable content providers in America by Cable Leaders in Learning, the cable industry's educational advocacy group based in Washington, DC.
Gary Olsen was designated a "Cable Leader in Learning" in May, 2009 by Cable in the Classroom, a foundation funded by the cable industry which puts technology in the hands of teachers to improve learning. Gary received the award for his work on "The Garden Organic," a cable show he created with Dubuque Community Schools and Mediacom Cable. The show chronicled the adventures of children as they grew their own food and prepared dishes right in the garden. "It narrows the intellectual gap between what grows from the earth and what ends up on their plates," explained Olsen. In addition to a $3,000 prize, he received an all-expenses-paid trip to Washington, D.C. where he was honored.