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.  

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.  

Jonathan Schwab is my personal mentor and the person that I look up to as a leader in my life. He was the Director of Housing at Yeshiva University, where he trained over 100 RAs to be future leaders in the Jewish world, is an advocate about infertility in the orthodox Jewish world, and is currently doing his doctoral research on the religious experience of Jewish students in faith-based universities. Mr. Schwab sits down to discuss his transition from an award-winning scientist and MIT recruit to a YU English major, the difference between “resume leadership” and “real leadership”, and what he learned about leadership from being a Presidential Fellow. He speaks about his experiences going through infertility, what he tried to teach Resident Advisors about leadership, and what it was like being the Director of Housing at the first university in America to have Covid. Mr. Schwab closes by talking about the necessity of self-care, his current research, and what it means to be a leader. 

Rabbi Dov Lipman was the first American-born member of Knesset in 30 years, is an activist and political commentator for the state of Israel, is the author of multiple books, and currently stands as the Secretary General of the Confederation for United Zionists. Rabbi Lipman sits down to discuss how he got involved in politics (hint: he didn’t grow up envisioning it for himself), the personal challenges that come with being in the public sphere, and the bipartisan humanity that he experienced during his time in the Knesset. He talks about how to build unity, addresses the story of a Rosh Yeshiva who disagreed with him, and provides a definition for zionism. Rabbi Lipman then closes with an explanation for what it means to truly lead. 

Mark (Moishe) Bane is the president of the Orthodox Union and a senior partner at the international law firm Ropes & Gray. Mr. Bane sits down to discuss his philosophy on leadership, how he approaches faith, and the difference between being close-minded and judgmental. He provides insight into his psychology and how that impacted his life path, why he chose lay leadership over other Jewish careers, and how he manages to balance all of his responsibilities (sneak peak: family comes first). Mr. Bane concludes by addressing the necessity to focus on the local level, the meaning in living in painful emotions, and what it means to truly lead. 

Arna Poupko Fisher is a widely renowned leader and educator who has lectured in over 120 different communities throughout North America. She was the first individual to be a full time scholar in residence of a federation, she was the president of the JCRC of Cincinnati, is a core faculty member for Wexner, which is the premier organization for Jewish leaders, is a faculty member in the Dept. of Jewish Studies at the University of Cincinnati, was an executive for the federation of Cincinnati, and is now a member of the board of trustees for the foundation. 

Arna Poupko Fisher sits down to discuss her path to Jewish leadership, the experience of being a female Jewish leader, and what she learned from speaking in so many communities. She talks about living a value-driven life, when it’s proper to stand up for one's beliefs, and the importance of parents in religious experience. Mrs. Fisher mentions the necessity of occasionally filling a leadership position because one is needed there, even if one isn’t passionate about it, and provides advice to future leaders. She closes off by highlighting how leadership and teaching are actually quite similar.