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Dwight Wintringer began their work experience in 1988 as an Executive Chef at Food for Thought, where they worked until 1992. In 2006, they joined Peddler's Son as the Director of Corporate Accounts, a role they held until 2015. Dwight also served as the Sales Manager at Peddler's Son from 2009 to 2022. In 2022, Dwight joined Recovery Café as an Operations Manager, where they worked until 2023.

Dwight Wintringer attended Kendall College, a Culinary Arts and Hospitality Management School in Chicago. Dwight studied Culinary Arts and Chef Training at the college. In January 2022, Dwight obtained a certification as a Certified Recovery Coach from the Connecticut Community for Addiction Recovery.