Simi grew up in the mountains of Aspen, Colorado and began Nordic racing when he was thirteen. A three-time NCAA All American, he joined the US Ski Team in 2010, racing in the Vancouver Olympic Games that February. Simi made his second Olympic team in 2014 Sochi earning a sixth place finish in the classic team sprint. He had a strong 2014 season, winning the freestyle sprint final at the Oberhof Stage World Cup as well as skiing to fifth place in the classic team sprint in Nove Mesto. When not training with the US Ski Team, Simi lives in Stratton, Vermont with sprint-focused teammate, Andy Newell where they both are members of the SMS T2 Team.