The artist was the youngest of three brothers. When art competitions were a form of play for the brothers, it later grew to his obsession. D’Alessandro attended the Art Institute of California where he explored mixing mediums as well as digital. He also attended illustration, sculpting, and fine art workshops. After spending long periods of time studying different techniques, D’Alessandro’s art became increasingly influenced by artists from the early 1900s. During D’Alessandro’s studies, he painted many different themes. He painted with restless intensity, often painting from morning until night. D’Alessandro was able to indulge his earliest artistic preferences for people, nature, architecture, and landscapes in his illustration and personal pieces.