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Bob earned his degree in Telecommunications Engineering in the United States Air Force, where he served for four years at Vandenberg Air Force Base in California. Following his military service, Bob worked as an independent telecommunications contractor, eventually working in management and executive roles in the telecom industry for 16 years.

Bob left the Telecom industry in early August of 2001 to begin a new career in Video Production, a long-time passion. In 2001, Bob Cannon Productions was launched. After several years of building this business, Bob began working with Camp Sweeney. For the past 18 years, Bob has provided year-round production, including Video Production, Photography and Social Media Support for Camp Sweeney.