How much does AI actually know about halacha? And how do different models stack up against one another?

In this episode of "Depends on the Context" I'm joined by Ben Niewood and Sam Weiss, two members of the five-person team behind HalachaBench, a project that put 24 leading AI models through real Israeli Chief Rabbinate semicha exams.

Ben, Sam and I get into the surprising results, why newer models sometimes perform worse than older ones, the challenges of having AI grade AI, and whether different models have their own halachic tendencies.

We also discuss the difference between knowing halacha and actually paskening, what the results mean for people already using AI to learn Torah or ask shailos, and where HalachaBench goes from here.

Links & Resources:

Website: https://halachabench.ai

X: https://x.com/HalachaBench

GitHub: https://github.com/halachabench/halacha-bench-results

Email: hello@halachabench.ai

*Results are preliminary and subject to further rabbinic validation.*

#DependsOnTheContext #HalachaBench #AI #Halacha

What connects the search for Israel’s lost tribes, learning Torah with an NBA star, and a run for the Knesset?

Rabbi Harry Rozenberg joins me on Depends on the Context to share his unconventional journey—from exploring communities with traditions of Israelite ancestry to building a friendship and learning partnership with Amar’e Stoudemire.

Harry and I have known each other for more than twenty years. We talk about the Vilna Gaon’s influence on his work, helping young men find their place beyond conventional educational paths, and the unexpected opportunities that shaped his life.

Along the way, we get into cannabis and psychedelics, Torah, sleep, the Yanuka, and his involvement in Israel’s Green Leaf party.

Links mentioned:

• Stat Academy: https://www.stat.academy/

• Letter to the Ten Lost Tribes of Israel: https://www.sefaria.org/Letter_to_the_Ten_Lost_Tribes_of_Israel

In this episode of Depends on the Context, I revisit the extraordinary story of Eric Martin, who spent $18,000 of his own money in 2015 trying to win a referral contest for Jet.com, an online retailer that hadn't even launched yet. He won 100,000 stock options. Just 18 months later, Walmart acquired Jet.com for $3.3 billion.

I've loved this story for years, so I recently contacted Eric to find out what happened afterward. He shared details about those three weeks, his conversations with Jet founder Marc Lore, and how the experience changed his life.

Drawing on original reporting and my own correspondence with Eric, I explore the gamble, the unexpected outcome, and what happened next.

Special thanks to Eric Martin for answering my questions and to journalist Kevin Roose, whose 2015 reporting first brought this story to light.

Links & Sources

• Watch the full episode on YouTube: https://youtu.be/E2Ky_AnOqKQ

• Kevin Roose's original 2015 article: https://web.archive.org/web/20171104084437/https://splinternews.com/this-guy-used-an-insane-get-rich-quick-scheme-to-become-1793845680

YUTorah has grown from a collection of cassette recordings into one of the world's largest online Torah libraries, with hundreds of thousands of shiurim available for free.

In this episode of Depends on the Context, I sit down with R' Robert Shur, Director of YUTorah, to explore the platform's history, the technology behind it, and how AI is transforming its future.

Rob shares why he believes AI should enhance Torah learning rather than replace it, why historic recordings are still at risk of being lost, and how AI is helping rebuild the site's search capabilities. Along the way, we explore YUTorah's funding, technical challenges, and what's next for the platform.

Explore YUTorah: https://www.yutorah.org/#YUTorah #TorahLearning #AI #JewishEducation

More than a decade ago, Alex Taub co-founded SocialRank, a platform that helped brands like the NBA, Netflix, and L’Oréal understand the people behind their social media audiences. The business was growing—until Instagram restricted access to its API in 2018, threatening the very foundation of the product.Now Alex is revisiting the same idea with SocialCrank, using AI and new technology to do things that weren't possible the first time around.In this episode of Depends on the Context, Alex and I discuss SocialRank's unlikely beginnings, what happened when Instagram pulled the plug, his journey through Upstream, and why an idea that was ahead of its time might finally have its moment.

Links:

https://www.socialcrank.ai/blog/introducing-socialcrank

In 1995, my family moved from Manhattan to Teaneck, New Jersey, and I took the basketball card collection I shared with my childhood friend Aryeh Buchsbayew ("Boo"). 31 years later, I finally made things right by finding the cards and sending them to Boo.

Boo and I have known each other since preschool, and what starts as a reckoning over the great basketball card heist of '95 turns into a conversation about turning 40, growing older, the lives we imagined versus the lives we've built, moving to Israel, and an unforgettable Limp Bizkit encounter.

Davidi Jonas went from being a high school rebbe and shul rabbi with no college degree to running Straight Path Communications, a company that sold to Verizon for $3.1 billion.

In this episode of Depends on the Context, Davidi and I explore his unlikely journey into telecommunications, the emergence of 5G, navigating the FCC, and the extraordinary bidding war between AT&T and Verizon- including what happened over Shabbos.

Along the way, we discuss opportunity, family connections, hard work, and Hashgacha Pratis- and how much of our success is really in our hands.

Today marks the first yahrzeit of my grandmother, Suri Lichtschein z"l, aka Babi Yaya.

In this special episode, my brother Elie and I look back on Babi's extraordinary 99 years of life — from surviving Auschwitz and rebuilding her life after the Holocaust to becoming the beloved matriarch of our family.

We share childhood memories, funny stories, and reflections on her remarkable sense of humor, unwavering emunah, and the legacy she left behind.

Originally recorded last year for our podcast An Excuse to Talk to My Brother, I'm republishing this conversation here on Depends on the Context in honor of her first yahrzeit.

May her neshamah have an aliyah.