Rabbi Weiss received his Semicha at the Hebrew Theological (Bet Midrash L'Torah) in Skokie, Illinois, as well as receiving an M.A. from the University of Illinois in English Literature. He led congregations in Chicago and Dallas and also served as head Jewish chaplain at Rush Medical Center in Chicago. Since making Aliyah in 1992, Rabbi Weiss has directed the Jewish Outreach Center in Ra'anana, helping to facilitate the spiritual absorption of new Olim. Rabbi Weiss is a regular columnist for the Jerusalem Post and Arutz Sheva, and lectures frequently in Israel, the United States and Europe. He also organizes and directs kosher tours and cruises all over the world. He currently serves as a member of the Ra'anana city council, and has been the recipient of the Rabbinic Leadership award from both the Orthodox Union and the Young Israel movement.
Rabbi Weiss is married to Susie and they have 6 children. In Sep. of 2002, the Weiss's eldest son, Sgt. Ari Weiss - a member of an elite anti-terrorist unit in the IDF's Nachal Brigade - was killed during a raid on Hamas headquarters in Shechem (Nablus). Rabbi and Mrs. Weiss have written and spoken extensively in many communities about drawing upon spiritual strength to cope with loss, and maintaining faith in the shadow of tragedy. In Ari's memory, the Ohel Ari Bet Knesset and Torah Learning Center was recently built in Ra'anana. It has become the largest Bet Knesset among Ra'anana's 85 shuls and is a focal point of study, Chesed and community action for the entire city.