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Richard Simon began their work experience in 1965 at United Service Companies, where they served as the President & CEO. United Service Companies specializes in providing safety, security, maintenance, and staffing services to airlines, public venues, hotels, residential complexes, trade shows, hospitals, and office buildings. Richard held this role for an unspecified duration.

In 2002, Richard joined the Chicago Convention and Tourism Bureau, where they became the Chairman of the Board. Richard held this position until 2005.

Richard Simon has completed education in Financial Mathematics at the Armed Forces Institute, but no start or end year for this education is provided. Additionally, they have obtained a certification as a 100 Ton USCG Master Captain from the USCG to operate watercraft. No information regarding the month or year of obtaining this certification is provided.