Rav Schneur Kessler: How to Give Guidance That Actually Reaches Someone, Openness Without Relativism, and the Path to Innerness in Judaism

"We Change Enough to Remain the Same": On the Anatomy of Daas Torah, Orthodox Judaism's Indeliberate Theology, and Wisdom That Reshapes How You See — with Prof. Benjamin Brown

Prof. Benjamin Brown is a Professor in the Department of Jewish Thought at the Hebrew University of Jerusalem and one of the world's leading academic experts on Orthodox Judaism, its ideology, and Halacha. He is the author of many books, among them a towering intellectual biography of the Chazon Ish, and his warmth through a screen and across an ocean was as palpable as his brilliance. We trace the evolution of Daas Torah, the idea that Torah speaks to every facet of life, even beyond the strictly halachic. We explore the revolution of Chassidus and how revolutions mature and stabilize over time. And we arrive at a perspective on change within Yiddishkeit that I found profound: that we evolve precisely in order to remain the same. I found this conversation deeply enjoyable and illuminating, and I hope you do as well. This episode is dedicated in honor of the birthday of my dear Bubby, whose birthday was on Yud Aleph Tammuz. May she have a beautiful and blessed year, full of health and happiness — physically and spiritually — and filled with nachas from her loving family. Bubby, all my love.

Elliot Wolfson: Mysticism, Paradox, and Speaking the Unspeakable

Professor Elliot Wolfson is one of the most remarkable minds working in Jewish academic thought today. A scholar, philosopher, poet, and artist, Wolfson holds the Marsha and Jay Glazer Chair in Jewish Studies at the University of California, Santa Barbara, and has spent decades mapping the innermost terrain of Jewish mysticism with a rigor and depth that few can match. Born on the nineteenth of Kislev — the holiday known in Chassidic tradition as the Rosh Hashanah of Chassidus, the day the Alter Rebbe was released from Czarist imprisonment and the inner teachings of the Torah were given new license to flow into the world — one might say his birthday itself portended a life devoted to the depths of Jewish mystical thought. We speak about mysticism and philosophy, paradox, the unspeakable, and what this lifelong quest means to him personally. Thank you for listening!

Rav Shlomo Einhorn: The Talmud, AI, and the Future of Jewish Learning

Rav Shlomo Einhorn is a talmid chacham, a master educator, and one of the most dynamic Rabbis I have encountered. For years he served as dean of Yavneh Academy in Los Angeles before stepping into a world most rabbis haven't touched — artificial intelligence. He is the founder and CEO of Mallacore, an AI consulting firm, and has been thinking and writing seriously about what this technology means for Torah, for learning, and for what it means to be human. What I love about Rav Einhorn is that none of this feels like a contradiction. For him, the move from yeshivah to AI was not a departure — it was a natural development. Because he sees in the architecture of the Talmud something that the builders of AI have been trying to approximate without knowing it. In this conversation we explore his claim that the Talmud is humanity's most sophisticated training manual for artificial intelligence, what AI can and cannot do when it comes to learning Torah, what a yeshiva might look like in 2036, and what will be gained and lost when the next generation learns with tools we can barely imagine today. We also talk about what all of this means for what makes us irreducibly human. This was a genuinely fun conversation. I hope you enjoy it.

Rav Schneur Kessler: How to Give Guidance That Actually Reaches Someone, Openness Without Relativism, and the Path to Innerness in Judaism

Friends, I am so excited to share this next episode of People of the Book — a conversation with someone I truly admire and who has been especially important and transformative in my own life. Rav Schneur Kessler is the Rav of the New Haven community and Rosh Kollel of the Kollel there. He is a talmid chacham par excellence, and one of the rare people whose depth of learning is matched only by his largesse of spirit. We talk about what it means to be a rabbi, how to maintain openness and curiosity amidst the specificity of one's own tradition, how to cultivate interiority in one's Judaism, and so much more. I hope you enjoy.

The Soul You Can't Lose: A Pesach Torah

There are two kinds of holiness in this world: the kind that is given to you, and the kind that you claim for yourself. Shabbos arrives like a gift, and then withdraws when the sun goes down. But the sanctity of Pesach, the added soul that a Yom Tov awakens, is something you reach for from within. Once you claim it, it can never be taken away. Based on a teaching from the Kedushas Levi, and a machlokes between Tosfos and Rashbam about the Neshama Yesaira.