Lenny was born and raised in Brooklyn, where he learned to swim at the relatively advanced age of 16 while at James Madison High School. He enjoyed being in the water so much that he soon decided to join the James Madison Knights' swim team for his junior and senior years. After graduating, Lenny enrolled at Brooklyn College to study Accounting, where he went on to compete for the Bulldogs' swim team during his freshman and sophomore years. Some of his hobbies include reading books, kickboxing, Brazilian jiu jitsu, ultimate frisbee, going to the gym, and traveling.