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His father, Dr. Jack McConnell worked at McNeil Laboratories and helped to develop Tylenol. The elder McConnell then started a free health clinic that was staffed by retired health workers in Hilton Head, South Carolina.

McConnell spent a year at Gill St. Bernards High School, in Gladstone, NJ before moving away. McConnell spent his senior year of high school at Lawrence Academy at Groton, in Groton, Massachusetts, and then attended Southern Methodist University from Fall 1982 to Spring 1984. McConnell transferred to Goddard College that fall where he would graduate in December 1987. This is where he met his mentor, Karl Boyle, and wrote his senior study "The Art of Improvisation" under Boyle's guidance.

McConnell joined Phish in 1985 and played his first official show on September 25 of that year. McConnell wrote four Phish originals — "Cars Trucks Buses," "Magilla," "Army of One" and "In a Hole" — and coauthored 11 Phish tracks.