Rabbi Yitzchok Lowy grew up in Lakewood in a Hasidic–yeshivish home, learned in top Lithuanian yeshivot, and later immersed himself in the world of contemporary Hasidic and Kabbalistic teachers.

In this conversation, we sit together in his beit midrash in New York and trace the “origin story” of his Beit Midrash Iyun LaMachshava—a study space built for people who can’t turn their minds off, but also don’t want to walk away from Torah or community.

We talk about the disappointment that pushed him away from standard mussar and hashkafa talks—“flat, one-dimensional” Torah that never allows for real complexity—and the attraction he felt to the broader “Hasidic renaissance” and Chabad-inflected thinkers who took ideas, soul, and inner work seriously. But then we follow him further, to the moment he realizes that even those teachers live in their own “boxes,” have red lines they refuse to cross, and sometimes won’t follow their own arguments to their logical end.

From there the conversation opens into bigger questions: the difference between faith and knowledge, why “I believe” is not the same as “I know,” and why the simple sentence “I don’t know” is, for him, a moral and spiritual stance rather than an admission of failure. We talk about the Rambam “ruining” the Talmud’s open-endedness, the loneliness of serious teachers who have no peers, the dangers of charismatic leadership and tzaddik-culture, and what it would take to build a real community of thinkers inside Haredi life rather than outside of it.

If you’ve ever felt “too thoughtful for the system” but still deeply attached to Torah, people, and place, this episode will feel uncomfortably familiar—in a good way.

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Levi Brackman is a rabbi, Ph.D. in psychology, best-selling author of Jewish Wisdom for Business Success, and founder of Invown, a platform for real estate fundraising and investing.