Kelly has been a fly fishing guide for 27 years. He started guiding in Michigan at the age of 16. He started his fly shop The Troutsman in Traverse City, Michigan, in 1981. He continued to run The Troutsman until the spring of 2002 when he moved to Montana and started The Slide Inn. He is an author and lecturer. His books are Modern Streamers for Trophy Trout (co-authored with Bob Linsenman) and Cripples and Spinners. Kelly has been published by virtually every major magazine in the business and is Editor-at-Large for Fly Fisherman Magazine. Kelly is also one of the hosts of Fly Fish TV on the Outdoor Life Network.