Gary was raised in small towns in the State of Oregon. He received his BA in philosophy from Yale University and his MBA in finance from the University of New Haven. He started his career in finance at the Connecticut Bank and Trust Company (CBT) as a trainee in their commercial banking program. Over a span of 16 years, Gary held various positions in sales and service for commercial and corporate clients, as well as credit administration and approval positions in both commercial and retail operations. CBT was acquired by Fleet Bank in 1990, where Gary was the Chief Credit and Loan Approval Officer for the $10 billion Fleet Bank of Connecticut.
After leaving Fleet, Gary built a series of small businesses, including cofounding a specialty executive-search firm focusing on banks, finance companies, private equity groups, and family offices. He also cofounded a specialty SBA finance company that eventually spread to 42 states. Gary then joined a group of investors to start a new community bank, The Bank of Southern Connecticut, and was its first president. He also formed a strategic and financial consulting company, FTG Financial, to help other entrepreneurs build their companies.