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As soon as the LIVE icon lights up, listeners of WWPT, 90.3 FM, in Westport, Connecticut, can expect an award-winning broadcast from 17-year-old Jason Lessing, an avid sports podcaster. A Staples High School senior in Westport, Lessing’s sports podcast earned him and his partners The John Drury High School Radio Award for the best sports talk program in the country last year.