Shadman is a senior at Sacred Heart High School in Massachusetts, where he has debated for four years. In that time, he has won the MBA Round Robin, the Glenbrooks, Yale, Manchester, the Massachusetts State Championship, Columbia, and the New England NFL District Tournament (twice); cleared to octofinals at the TOC; placed 5th at NCFL Nationals; placed in the top 25 at NFL Nationals; reached elimination rounds at Greenhill (twice), Apple Valley (twice, quarterfinalist, 2006; top speaker, 2007), Blue Key, and Harvard; and twice participated in the Greenhill, Lexington (2nd place, 2007), and MBA (5th place, 2007; Champion 2008) Round Robins. In the last two years, he has earned 7 TOC bids.