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John Olenchalk started their work experience as a teammate for the Montreal Alouettes in 1978. John then joined the Kansas City Chiefs as a teammate from 1981 to 1983. John later worked as a Manufacturer's Rep for Mohasco (Stratford Stratolounger Furniture) from 1983 to 1985. After that, they became a Senior Associate at C.T. B.T. Commercial Real Estate from 1985 to 2008. Currently, John is working as a Senior Vice President and Partner at Kidder Mathews since May 2008.

John Olenchalk attended Stanford University from 1973 to 1977, where they obtained a Bachelor of Arts (B.A.) degree in Human Biology.