Born on July 29, 1972, DeMaio grew up in East Haven and graduated from East Haven High School in 1990 as class salutatorian. He was 2-sport captain in both basketball and baseball and gained 2nd team All-Housatonic and 1st Team All-New Haven Country in basketball and 2nd team All-Housatonic in baseball. After high school he pursued a career in teaching and coaching. DeMaio has a Bachelor’s in History and Teaching Certification from Southern Connecticut State University (1995) and later a Master’s degree in History (2005). He is currently pursuing an additional degree in education administration. DeMaio has been coaching high school basketball since 1992 and also coached baseball as an assistant varsity coach for two years at North Haven High School und Bob DeMaio (unrelated). He has taught social studies at North Haven High School for more than 25 years. DeMaio was awarded Teacher of the Year at North Haven at High School three times was named SCC Coach of the Year on two occasions and was inducted into the North Haven High School Athletic Hall of Fame in 2015. He resides in Wallingford for the past 23 years with his wife and two children.