Gary began his career as a doorman for a New York City hotel, upon graduating Fairleigh Dickinson University, with a Bachelor of Science in Business Management and minors in Corporate Finance and Information Systems, Gary accepted a position with ITT Sheraton as a Corporate Trainee.

During his tenure, he rapidly rose through the ranks through a series of increasingly responsible positions, mergers and acquisitions, at both the corporate and property level, in the disciplines of finance and operations.