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Ben Gastright has a diverse work experience spanning various industries. Ben started their career in 2005 as an English teacher at James Cook Languages and HEB Central Market, where they taught job-specific vocabulary to adults. In 2006, they pursued their passion for music and worked as a musician, composer, and arranger with Bravo, Max!. Ben then worked as a hardwareman at Klingenberg's Hardware from 2012 to 2015. In the same period, they also worked as a bartender at Chuy's Tex Mex. Since 2015, Ben has been associated with the Northern Kentucky Chamber of Commerce, initially as an Export Compliance Manager and currently as the Director of Communications.

Ben Gastright attended Taylor University from 2001 to 2005, where they earned a Bachelor of Arts degree in Mass Communication/Media Studies. In 2005, they attended TEFL Worldwide Prague and obtained an EFL Certification in English/Language Arts Teacher Education. In April 2016, they obtained a certification as an International Commerce Specialist from the World Trade Center Kentucky.