Tom Gillespie was born in 1953 and raised in Seward, Alaska. His father worked as a longshoreman and a logger. The family had a homestead on Old Exit Glacier Road and Clear Creek. Tom is an avid outdoorsman, climber, skier, and runner. He has worked as a hunting guide, in the construction industry, and as a heavy equipment operator. In the 1980s, he and his wife ran Creekside Cabins, a bread and breakfast accomodation in Seward.