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Dick Holbert started their work experience in 1969 as a Captain and Special Action Officer in the US Army, serving until 1972. In 1972, they became the President of Central Flying Service, Inc.

Dick Holbert obtained a Juris Doctor degree from Georgetown University Law Center from 1965 to 1968. Prior to that, from 1961 to 1965, they earned a Bachelor of Science in Business Administration (BSBA) degree with a focus on Business Management from the University of Arkansas. In addition to their formal education, Holbert obtained a Certificate of Completion from Hague Academy of International Law in The Netherlands in 1966. It is not specified whether they obtained any additional certifications from Hague Academy of International Law.