After graduating from the United States Military Academy at West Point in 1986, Barry served in the Army in command and staff positions mainly within the 82d Airborne Division, and various Field Artillery, Infantry, and Armor units. After 28 years of service, he retired at the rank of Colonel.

Barry began his second career as a Financial Advisor with Northwestern Mutual in 2017 and is a Retirement Income Certified Professional serving clients across the country.

Barry and his family reside in Charlotte North Carolina where they enjoy golf, music, and travel.