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Chris Mileski has a diverse work experience. Chris started their career in 1998 at NBC Securities, Inc. working in cash management until 2001. From 2002 to 2009, they were a TV Producer/Director for the Turner Broadcasting System, working on the Rick and Bubba Radio Show. In 2011, they became a Radio Personality at Crawford Broadcasting until 2017. Currently, they work as the Director of Marketing and Development at Hometown Lenders, Inc.

Chris Mileski attended Huffman High School from 1984 to 1988, where they obtained a high school diploma. Later, from 2000 to 2004, they attended Birmingham-Southern College and earned a Bachelor of Arts (B.A.) degree in Theology, with a focus on Theological and Ministerial Studies. Additionally, Chris holds a certification in Engineering and Design, known as the CT Certification, although the specific details regarding the institution and date of obtaining the certification are not provided.