Rebellious and free thinking from the age of five, Mordechai insisted that he be considered a "boy-girl" on his first day at his ultra-Orthodox kindergarten. Throughout the next sixteen years in Orthodox yeshivas, Mordechai continued to challenge the gender norms of Orthodox Judaism, while developing a proficiency in Judaic studies. He was the first student in Yeshiva University to come out of the closet. In college Mordechai became New York's first male Certified Rape Crisis Advocate. Mordechai was accepted early-decision to Stony Brook Medical School where he studied medicine for two years until taking a leave of absence to pursue a Masters in social work. Mordechai worked as a social worker for teens at the LGBT Center of Manhattan and as the LGBT consultant for the UN NGO Committee for Human Rights. He founded "JQY," a nonprofit for LGBT youth in the Orthodox community, and serves as its executive director.