Massimo is an industry veteran, having played tennis since he was a young boy growing up in Italy. As a high-performance junior tennis player, Massimo was recruited to train at the world-famous Nick Bollettieri Tennis Academy in Bradenton, Florida and went on to play professionally on the tour. Returning to Italy to attend university, Massimo graduated and returned to the world of tennis as a coach, Director of High Performance Tennis and Director of Tennis at the Aspria Harbour Club Milano, in Milan. During that time, he captained a team of world-ranked players including Omar Camporese (No. 18), Claudio Mezzadri (No. 26) and Paolo Cané (No. 26). In 2013, he was recruited by the prestigious Tennis Corporation of America to become the General Manager of the Midtown Club in Weston, Florida. Over his career, Massimo was the Founder and Organization Director of the Aspria Harbour Club ATP Milan International Tennis Tournament, as well as the Founder of the International Swim Meet, both events attracting top players and athletes from all over the world.