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Rick Winchell started their career in 1983 as a Technician and Team Leader for the MK86 Weapon System in the U.S Navy. Rick operated and maintained the weapon system on a nuclear-powered cruiser until 1989. In 1989, they joined Mazak North America as an IT Operations - Service and Security employee, where they officially transferred to the IT department in April 2016.

Rick Winchell attended Certified Ethical Hacker Training in 2013. This training focused on becoming a certified ethical hacker, though no specific degree was obtained. In 1989 to 1991, they attended an MCSE (Microsoft Certified Systems Engineer) program. This training was aimed at becoming a Fire Control Technician for the U.S. Navy. Again, no degree was specified.