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Sy is originally from Chillicothe, Ohio and received his BA in Integrated Strategic Communications from The University of Kentucky in 2009. While attending UK, he worked in the public relations department within the hospitality management field, was a group leader with the Boys and Girls Club of America and also did public speaking for a prosthetics facility. Sy then moved to West Virginia and worked in the education system while also doing some motivational speaking in regards to young athletes. He is currently working on his Masters Degree in Sports Leadership at The University of Kentucky where he hopes to get into the field of higher education concentrating on athletic motivation and leadership. He lives in Lexington with his fiance Sarah and when not working or studying, never misses a CATS basketball game.