Alessandro graduated from Harvard University with an A.B. in History. While a student, he worked at Widener Library assisting patrons with research and training new employees. He is a lifelong resident of Boston, and enjoys local and social history. He is particularly interested in New England, Irish, and Italian ancestries. In 2017 he traveled to Italy to conduct research, and he has traced his patrilineal family to the early 1600s. He enjoys deciphering manuscripts and Latin parish records.