Penny's father Dr. Larry Bregman was a founder of the original Hebrew Academy where she was a student. Penny obtained a Bachelor's Degree from the University of Miami where she played volleyball. She then went on to receive her Master’s Degree from Georgia State University. Penny started the health, physical education and athletic program at Greenfield Hebrew Academy. From 1980 to 1999, Penny developed and continued the Dr. Larry Bregman Special Olympics at GHA, where over 100 special Olympians competed. She has also been coaching the girls’ volleyball team for sixteen years, with a record of 292 wins and 63 losses.