Anatomy of a Jewish Leader

Ofer Gutman is the CEO of Masa Israel Journey, the leader of long-term Israel experiences, which has served over 160,000 young adults from more than 60 countries since its founding. Prior to this he was the CEO of Israel Venture Partners, a non-profit organization that provides educational resources to underprivileged youth in Israel, and the Central Sheliach of the World Zionist Organization in North America, where he focused on forging connections between students on college campuses and Israel. Ofer begins with a basic update on how he is doing amidst all of the unrest in the region. He then discusses how he ended up in his role at the World Zionist Organization and the challenges that he faced on college campuses, the difference between experiential and other forms of education, and what the poverty and inequality looks like in Israel and what he has seen to be most effective in combating it. Ofer then speaks about how he has managed leading a global team spread across 15+ countries, how his approach to running Masa has shifted over Covid, and how he dealt with the recent tragedy in Meiron, in which 2 Masa participants passed away. He closes by sharing his feelings around how the culture in many parts of the world are making people genuinely afraid to show support for Israel, what he wants his legacy to be, and what it means to lead.

Dr. Rivka Press Schwartz is an Associate Principal at SAR High School, a fellow at the Shalom Hartman Institute, and the Co-Director of Machon Siach. She holds her PhD from Princeton and lectures on issues of contemporary importance in the Orthodox community. Dr. Rivka Press Schwartz sits down to discuss her transition from being raised in a more “right-wing” community to Modern Orthodoxy and highlights a fascinating story of perseverance which landed her at Princeton. She then speaks about sex education in the Orthodox community, her balance between being grounded in empathy and having a strong teaching style, and the role of women in Judaism. The episode concludes with a discussion about how she hopes for her legacy to be tied to the interplay between Orthodoxy and race relations and what she believes it means to lead.

Rabbi Yehuda Sarna is the Chief Rabbi of the Jewish community of the United Arab Emirates and the Executive Director of the Bronfman Center and a University Chaplain at NYU. Rabbi Sarna sits down to discuss the vision that he had for himself growing up, how his experiences on 9/11 shaped his approach to leadership, and what he feels he can give most to his university students. He speaks about teaching open mindedness, interacting with and overcoming his own preconceived stereotypes, and his experiences in the United Arab Emirates (including what people most misunderstand about his job there). Rabbi Sarna concludes with what it means to lead.

Before this podcast ever launched, the person I most wanted to interview was Rabbi Lord Jonathan Sacks, who unfortunately passed in November 2020. As a member of the House of Lords and Chief Rabbi of the UK, he stood as a pillar of Judaism, politics, philosophy, and morality. While Rabbi Sacks is no longer with us, I felt it critical to still have an episode to assist in better relating to and learning from him. This special episode has three parts: Mrs. Joanna Benarroch was the Director of the Office of Rabbi Sacks and worked closely with him for countless years. She discusses her first interactions with Rabbi Sacks and provides insight into Rabbi Sacks’s personality, how he led and managed a team, and what she learned from working with him. She concludes by highlighting how she believes Rabbi Sacks most exemplified leadership. Dr. Daniel Rynhold is the Dean of Revel, Yeshiva University’s Graduate School of Jewish Studies. He had the privilege of studying under and learning from Rabbi Sacks. He discusses their relationship, what he learned from Rabbi Sacks, and brings to light Rabbi Sacks’s unique role in the world of Jewish philosophy. He concludes by mentioning what he believes Rabbi Sacks’s vision for how a person, and Jew in particular, should view their role in the world. I humbly close the episode with a lesson on both leadership and humanity that I learned from Rabbi Sacks and that has had a profound impact on my life.

Rabbi Haskel Lookstein is the former principal of Ramaz, Rabbi Emeritus of KJ, and one of the most influential American Jewish activists of the last century, to the point where Newsweek called him the most influential orthodox rabbi in America. As there was so much to discuss, this episode was split into two parts. Part 1: Rabbi Lookstein sits down to discuss his close relationships with massive Jewish figures, such as Rav Soloveichik and Rabbi Lamm, how he came to be in the rabbinate, and the experience of becoming the rabbi of the synagogue he grew up attending. Rabbi Lookstein expounds on his outlook on education, explains his commonly-used phrase “don’t let school interfere with your education,” and discusses what zionism means for him on a personal level. Part 2: Rabbi Lookstein speaks about his activism, with a focus on Soviet Jewry (he visited multiple times, had a close relationship with Natan Sharansky before he was even imprisoned, and led countless rallies that had serious impacts). Rabbi Lookstein discusses what it was like to write his Ph.D. with the help of Eli Weisel on “The Public Response of American Jews to the Holocaust, 1938-44.” He then describes the relationship between orthodoxy and open mindedness, his roles in the public eye (participated in Obama’s prayer services and converted Ivanka Trump), and how music and prayer has played a massive role in his life. Rabbi Lookstein concludes by defining what it means to lead.