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Riley McCulley II has worked in the hospitality industry since 2012. Riley began their career as a Catering Supervisor at Michaels Catering in 2012. In 2015, they moved to Nando Milano Trattoria as a Manager. In 2016, they became the General Manager of Enoteca crudo. In 2018, they joined Naya Restaurant Group as the Director of Beverage Sales and Sommelier. Most recently, in 2020, they were appointed Regional Vice President, Director of Sales, and Director of Marketing at Kinetic Agency.

Riley McCulley II attended the University of Illinois Urbana-Champaign from 2012 to 2015, where they earned a Bachelor's degree in Philosophy.