Mr. Lipson spent his early career as a computer software analyst. In the early 1980s, companies transitioned from manual processes to computer-supported processes. He worked for Boston Water and Sewer, Lotus Development, Bank of Boston, and Digital Equipment.
He secured a legal degree from Western New England University, transitioned to legal work, and worked in private practice for five years. After receiving an MBA from Columbia University, Gary took a position at IBM and worked as a negotiator for seventeen years, supporting the semiconductor division.