As the son of a letterpress printer in Verona, his interest in the graphic world began at an early age. After a start as a graphic designer for a small publishing company, Diego moved on to gain experience as a junior art director working on branding for Italian sportswear labels. In 2003, he started a new freelance life as a digital art director in Paris. His work with Watoo Agency won the 2005 Flash Festival Award for Best Web Graphics. He also joined the ASE network, a branch of Capgemini consulting, working on workshops for large corporations such as Air France, Bacardi, and Volkswagen.

Diego co-founded UP! in 2006. The firm's talent base enabled them to work with a wide variety of clients such as Kenzo, Vanessa Bruno, Eastpak, and Florence-based fashion fair Pitti. He served as a creative consultant for the branding and communication of Greenpeace France. Since he moved to NYC in early 2010, he worked both with fashion brands and agencies. After he shaped the new Diane von Furstenberg brand identity, he joined Sub Rosa's workshop, working on several successful projects for Nike, Warby Parker, GE and Pantone. He then returned to DVF to lead the creative team, conceiving and executing numerous digital and print campaigns and winning a Clio Award in the Design Category for the book Journey of a dress, published by Rizzoli.