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The Land of AND · May 5, 2026

We Come Bearing Ancient Technology

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Jenna Arnold · The Land of AND

For 5,000 years, asking hard questions hasn’t just been a Jewish pastime — it’s been the mandate. A spiritual practice. A form of love. A duty. Part of what it means to be Jewish is to wrestle: with each other, with the headlines, with paradoxes that refuse to resolve neatly, and with questions so big they’ve outlived every generation that tried to answer them.

And here’s the gift buried inside all that wrestling: we didn’t just inherit the questions. We inherited ancient technology to help us inch closer to the answers. Forged over millennia, centuries of accumulated wisdom about how to argue toward the true. Turns out, those tools are exactly what this moment is asking for.

That’s where this series, Command F, comes in.

We’ve excavated some of the most interesting questions the AI age is handing us. We’ve sourced the wittiest thought partners, the sharpest thinkers, the people brave enough to sit with complexity without flinching. And we’ve tapped the experts who live at the intersection of ancient wisdom and whatever the hell is happening right now.

Command F takes a very modern dilemma — love, grief, identity, art, parenting — and runs it through something much older: debate, disagreement, and a 5,000-year-old collection of clues. Call it a spiritual GPS. A set of coordinates, handed down generation by generation, for exactly the kind of terrain we’re standing in now.

We think there’s something in here for everyone. You don’t have to be Jew-ish to need better questions. You just — like the rest of us — might need smarter ones.

Watch Live: Twitch · Substack · YouTube · Instagram

Here’s what’s coming:

EP 1: A Message for the Unknown (l’dor v’dor) Tuesday, May 6th at 11:30am ET What do we choose to pass on — and who are we, now that AI gets to help tell our story? With Sasha Sagan (For Small Creatures Such as We), Gabriella Di Laccio (TED Fellow & founder of the Donne Foundation), Sara Wolkenfeld of Sefaria, and Jewish futurist David Zvi Kalman.

EP 2: The Power of IDK (machloket) Thursday, June 12th What if uncertainty isn’t a bug — it’s the whole system? Featuring philosopher Chris Largent and comedian ‘Bad Rabbi’ Charlie Buckholtz on the dangers of incuriosity, the patriarchy of “owning” information, and why humility might be the most radical act of 2025.

EP 3: Optimize This (zivug) Wednesday, May 14th Can you optimize love… or does that kill it? With Molly Tolsky (Hey Alma), matchmaker Greta Tufvesson (The Bevy), and maybe your mother’s worst nightmare: data-driven romance.

EP 4: Art for Art’s Sake (l’shma) Tuesday, May 20th Why create when machines can do it faster? With Molly Crabapple (NYT bestselling author of Here Where We Live is Our Country) and others making meaning anyway. On Jewish creative history, art as survival, and whether beauty still has a job.

EP 5: Grief (zecher) Tuesday, May 27th Would you text someone who’s no longer alive… if you could? With death-dinner pioneer Michael Hebb and grief coach CJ Infantino. On AI resurrection, what Judaism says about the soul, and whether letting go is still possible when the dead text back.

EP 6: Golem 2.0 Wednesday, June 4th We built something. It might be smarter than us. Do we owe it dignity — or is the real question whether we’re building our own destroyer and calling it progress? With philosopher Carissa Veliz.

More episodes to come on parenting, identity, multi-faith futures, and the radical act of unplugging.

Watch Live: Twitch · Substack · YouTube · Instagram

Our resident guides — Rabbi Yonah Schiller, founder of Common Era, and David Zvi Kalman, Jewish futurist and the mind behind Jello Menorah — will be weaving in and out of conversations all season.

This isn’t a show about whether AI is good or bad.

It’s about whether we remember how to be human while using it.

The Talmud wasn’t written in a Google Doc. But it was argued over, interrupted, revised, and made better by everyone in the room.

Come be in the room.

Welcome to Command F. Come wrestle with us.

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