Jewish Insights with Justin Pines

As we approach Tu BiShvat, the New Year for Trees, we traditionally look to the roots that sustain us. But in 2026, the most intensive growth on our planet will be found in the “silicon orchards” of data centers and artificial intelligence. How do we ensure that as our world gets smarter, our lives do not become less sacred? In this episode of Jewish Insights, host Justin Pines sits down with Rabbanit Sara Wolkenfeld, Director of Education and Chief Learning Officer at Sefaria (sefaria.org), to explore the profound intersection of Torah and technology. From the democratizing power of the digital Jewish library to ancient Talmudic cautions that feel uncannily relevant in the age of social media, the conversation examines what it means to remain rooted in the values of Sinai while building a world of code. Join us for a thoughtful look at how Jewish ethics may offer the ultimate operating system for the future. For more information go to www.sefaria.org (http://www.sefaria.org)

Do you ever feel like you’re talking into a void? Whether you are navigating a difficult conversation in your marriage or seeking a deeper sense of purpose, the secret to being heard starts with learning how to truly listen. Rabbi Dov Singer is the head of the renowned Makor Chaim Yeshiva and a primary leader in the modern revival of emotional and religious intelligence. He is the author of the life-changing guide Prepare My Prayer, a book dedicated to helping people of all backgrounds bridge the gap between their inner worlds and their daily lives, and established the Beit Midrash L'Hitchadshut - The Study Center for Renewal, an adult spiritual outreach program, and Lifnai VLifnim, an educators’ training program. In this episode, Justin Pines sits down with Rabbi Singer to explore a profound shift in mindset: moving from speaking about our challenges (and the Divine) to speaking to them. By applying the principles of radical listening and intentional speech, we discover that our words are not just descriptions of our reality—they are the very tools we use to build it. This conversation translates deep spiritual concepts into a practical framework for anyone looking to cultivate more presence, humility, and resilience. Key Takeaways Radical Listening: Why we have two ears and only one mouth—and how to listen to the "soul" behind the words of others The Creative Power of Speech: Understanding how intentionality in small moments, like saying "good morning," can reshape your physical and emotional environment. The Art of Creating Space: Why effective leadership and parenting require us to step back (Tzimtzum) to allow those we lead to truly grow.. Connect & Follow Watch the full series: https://www.youtube.com/playlist?list=PLDYxKuIDCjn0TWM937-7qQf9w6JGmCWGX Follow Justin on Instagram: https://www.instagram.com/justinpines/ Follow JBS on Instagram: https://www.instagram.com/jbstvorg/

In a world of constant stress and uncertainty, how do we build a life of purpose and emotional stability? Discover how a former combat commander uses ancient wisdom to build modern resilience and unbreakable character. Rabbi Binny Freedman is the Rosh Yeshiva of Orayta in Jerusalem and a former Company Commander in the IDF. Having survived the 2001 Sbarro bombing, Rabbi Binny’s teachings on gratitude and leadership aren't just theoretical—they are battle-tested insights from a man who has navigated the extremes of human experience. We often view "ethics" as a set of rules, but the Jewish concept of Middot (character traits) is actually a technology for habit-forming. Using the "Maimonides Method," Rabbi Binny explains how to build a "healthy soul" through intentional repetition—turning positive actions into second nature so you can remain balanced even in high-pressure environments. Key Takeaways: The Power of Proactive Giving: Why shifting from a "rights-based" to an "obligations-based" mindset is the ultimate antidote to modern anxiety. The Science of Habit: How to use intentional repetition to overwrite negative behaviors and build lasting inner strength. Willpower as a Muscle: Why setting personal boundaries and ethical "restrictions" actually creates the freedom to succeed in professional and personal life. Connect & Follow Watch Additional Episodes of Jewish Insights: https://www.youtube.com/playlist?list=PLDYxKuIDCjn0TWM937-7qQf9w6JGmCWGX Follow Justin on Instagram: https://www.instagram.com/justinpines/ Follow JBS on Instagram: https://www.instagram.com/jbstvorg/ #Leadership #Wisdom #JewishInsights #Mindset #JustinPines #Resilience #CharacterBuilding #PersonalGrowth

What does it mean to be a Jew outside of Israel? Long before the Maccabees, the Jewish people faced a crisis that would shape their identity forever: the choice to remain in the Diaspora. In Part 1 of this special Chanukah series on Jewish Insights, Justin is joined by Dr. Malka Simkovich to explore the "Second Temple Era" not just as a time of rebuilding, but as the birth of a global Jewish people. Together, they explore exile, Diaspora, and the “failure” to return to Israel, uncovering the surprising history of the Persian era, the thriving Jewish communities of Egypt and Babylon, and the "ingredients" (Shabbat, Kashrut, Circumcision) that kept Judaism alive without a Temple. Dr. Malka Simkovich serves as Editor-in-Chief of the Jewish Publication Society, Visiting Professor at Yeshiva University’s Revel Graduate School for Jewish Studies, is a member of President Isaac Herzog’s Voice of the People delegation, and was the Crown-Ryan Chair of Jewish Studies and Director of Catholic-Jewish Studies at Catholic Theological Union. #Chanukah #JewishHistory #SecondTemple #JewishInsights #JBSTV #Diaspora #JewishIdentity

If truth is one of the foundational pillars of any stable society, how do we navigate a world which often feels post-truth? In this special JI episode in honor of Jewish Book Month’s 100th anniversary, Justin sits down with Tali Rosenblatt Cohen, host of The Five Books podcast. They begin by exploring Tali’s own mission for The Five Books Podcast: the profound power of Jewish literature to foster empathy and a sense of shared purpose, especially during moments of crisis. Tali also shares her insights on the expanding landscape of Jewish storytelling in 2025, 2025, from the enduring resonance of Holocaust literature to the rise of stories exploring Sephardi, Mizrachi, and romantic Jewish experiences. Then, Justin steps into the guest seat to share the five books that shaped his life and led to a lifelong quest for authenticity and truth (Emet)—a search he views as the central project of the Jewish tradition. Listen as Justin shares his five books and discusses: How a classic American novel sparked his obsession with "phonies." Why the Jewish tradition is a centuries-long debate aimed at "getting the answer, not being right." The revolutionary theological concept that every human we meet is a messenger from God. This conversation is a powerful celebration of reading, identity, and the spiritual journey that connects them both. Rabbi Justin Pines' Five Books: The Catcher in the Rye The Jewish Way: Living the Jewish Holidays The Story of Joseph and His Brothers Living Emunah: Achieving a Life of Serenity Through Faith Ohr Yisrael and Other Writings

How does the largest local Jewish philanthropy in the world navigate a decade defined by crisis? In this episode of Jewish Insights, Justin sits down with Eric Goldstein, the outgoing CEO of UJA-Federation of New York, for a candid and profound reflection on his 12-year tenure. From leaving a prestigious legal career to leading the Jewish community through the 2014 Gaza War, the COVID-19 pandemic, the war in Ukraine, and the aftermath of October 7th, Eric shares the lessons he’s learned about leadership, resilience, and the power of community. We discuss the rise of antisemitism—revealing how UJA’s security budget went from $0 to over $6 million in just a few years—and the incredible "surge" of Jewish engagement and philanthropy seen since October 7th. Eric also outlines his vision for the future: moving beyond just fighting enemies to investing in "robust Jews" who are educated, proud, and resilient. Whether you are concerned about the future of American Jewry or seeking inspiration from Jewish leadership, this conversation is a must-watch.

Jennifer Apple, the star of the show "Hannah Senesh," presented by the National Yiddish Theatre Folksbiene, joins Justin to discuss taking on this role, and the impact and legacy of Hannah Senesh. Jennifer originated the role of Anna in the Tony Award-winning "The Band’s Visit" First National Tour and received an Elliott Norton Award for Outstanding Lead Performance as Dina in the Huntington/SpeakEasy Stage production. Learn more at: https://www.jenniferapple.net You can learn more about NYTF’s Hannah Sennesh at: https://nytf.org/hannah-senesh/