Why I've Been Quiet: Building AI-Powered Jewish Learning App

I haven't posted much lately. Not because I ran out of hot takes about branding or leadership (trust me, those are endless), but because I've been buried in something I couldn't stop building.

For the past several months, I've been heads-down on Derekh Learning , an iOS app that lives right at the intersection of everything I am: the tech guy who builds websites for a living, the proud Jew who grew up in day school, the AI optimist who thinks these tools can actually serve meaning instead of replacing it, and the person who believes ancient wisdom shouldn't be locked behind barriers that don't need to exist.

Here's the thing about Jewish learning: it's profound, it's beautiful, and it's often stuck in formats that don't fit modern life.

Rigid schedules. Intimidating entry points. One-size-fits-all approaches that assume everyone learns the same way, at the same pace, with the same questions. And look, I get it; tradition matters. But somewhere along the way, we made it harder than it needs to be for people to actually engage with the texts.

I kept thinking: what if Torah, Talmud, and Jewish wisdom could meet you where you are? What if learning felt like a conversation with a really smart friend instead of a performance you're supposed to nail? What if the texts could speak to your actual questions about parenting (because Yael asks me wild stuff), work (because office politics is basically applied Talmud), purpose, identity, all of it?

And then the kicker: what if AI could help make that real?

Derekh Learning is a digital beit midrash where ancient texts meet modern curiosity. That's the elevator pitch, anyway.

Here's what that means in practice:

It's personalized . Your derekh (path, literally "the way") through Jewish learning goes at your pace, interests, and tries to help answer the questions you're actually asking. No guilt if you miss a day. No one correct way to do it. Just consistent, curious engagement with the texts that have shaped us for millennia.

It's built with AI , but not in the way you might think. I'm not trying to replace the soul of learning or turn Torah into ChatGPT. The technology helps surface connections you might not see, suggest pathways based on what you're curious about, and meet you in the chaos of real life. You know, when you've got 10 minutes between meetings or during nap time (shoutout to parents everywhere).

It's designed for people who want depth without having to leave their actual lives behind . Small daily practices. Modern questions. Ancient answers. Built for the curious, not just the scholars.

I'm a technologist who believes tools should serve meaning, not replace it. I've spent years building websites that tell stories, and I wanted to build something that helps people write their own story through learning.

I'm a Jew who loves the texts and wants more people to feel at home in them. Growing up, I had access to incredible teachers and a community that made learning feel alive. Not everyone gets that, and it bugs me.

I'm someone who's spent years thinking about AI and what it can unlock when used with intention. Not hype. Not shortcuts. Just smarter ways to connect people to what matters.

And yeah, I'm a Miami guy who thinks learning should have warmth, energy, and a little cafecito-fueled optimism. (And if your approach to Torah doesn't have at least a hint of chutzpah, are you even doing it right?)

Derekh Learning is what happens when you let all of that collide.

The app is live now in the App Store. Sign up today and use code FINDYOURDEREKH in the app setting for 50% off your first year. If you've ever been curious about Jewish learning but didn't know where to start, or if you've been learning for years and want a new way to engage, I'd love for you to try it.

More to share soon about what we're building, the ideas behind it, and the community taking shape around it. But for now: this is what I've been working on. This is my derekh.

And if you've got thoughts, questions, or just want to talk about how AI and ancient texts can coexist without the world ending, you know where to find me.