Why Your AI Learning Projects Keep Fizzling Out
AI and I14 Tammi

Why Your AI Learning Projects Keep Fizzling Out

LLMs have made it absurdly easy to go deep on almost any topic. So why haven’t we all used ChatGPT to earn college degrees we wished we had majored in or pursued a niche interest, like learning how to name the trees in our neighborhood? I know I’m not the only one to feel guilty for well-intentioned attempts at autodidactism that inevitably peter out.


Entrepreneur Nir Zicherman has a reason for this disconnect: LLMs can answer most of your questions, but they won’t notice when you’re lost or pull you back in when your motivation starts to fade.


As the CEO and cofounder of Oboe, a platform that generates personalized courses about everything from the history of snowboarding to JavaScript fundamentals using AI, Zicherman has thought deeply about why the ability to access information does not automatically lead to understanding a concept. In this episode of AI & I, he talks to Dan Shipper about everything he’s learned about learning with LLMs.


They get into Zicherman’s counterintuitive belief that learning is a more passive process than you’d think, the biggest blocker for most people who want to learn something new, and where AI agents currently fall short in providing a meaningful learning experience.


If you found this episode interesting, please like, subscribe, comment, and share!


Want even more?

Sign up for Every to unlock our ultimate guide to prompting ChatGPT here: https://every.ck.page/ultimate-guide-to-prompting-chatgpt. It’s usually only for paying subscribers, but you can get it here for free.

To hear more from Dan Shipper:

Subscribe to Every: https://every.to/subscribe

Follow him on X: https://twitter.com/danshipper


Timestamps:

00:00:00 - Start

00:00:36 - Introduction

00:01:49 - Why you need a dedicated AI learning app

00:04:32 - The process of learning is more passive than you might think

00:10:21 - Live demo of Oboe to create a course about philosopher Ludwig Wittgenstein

00:16:52 - Learning works best when it comes in many formats

00:28:21 - Where AI agents currently fall short in the learning experience

00:34:10 - The importance of making learning feel accessible

00:35:56 - How Zicherman uses Oboe to learn quantum physics

00:40:54 - How embeddings spaces remind Dan of quantum mechanics


Links to resources mentioned in the episode:

Nir Zicherman: @NirZicherman

Learn something new with Oboe: https://oboe.com/

Jaksot(98)

How We Built 'Claudie,' Our AI Project Manager (Full Walkthrough)

How We Built 'Claudie,' Our AI Project Manager (Full Walkthrough)

A few weeks ago, Natalia Quintero wouldn’t have called herself technical. But since the beginning of January, she has woken up at 6 a.m. to vibe code with Claude. The AI project manager she built save...

4 Helmi 47min

How Andrew Wilkinson Uses Opus 4.5 in His Work and Life

How Andrew Wilkinson Uses Opus 4.5 in His Work and Life

Entrepreneur Andrew Wilkinson used to sleep nine hours a night. Now he wakes up at 4 a.m. and goes straight to work—because he can’t wait to keep building with Anthropic’s latest model, Opus 4.5.Two y...

21 Tammi 1h 2min

Vibe Check: Claude Cowork Is Claude Code for the Rest of Us

Vibe Check: Claude Cowork Is Claude Code for the Rest of Us

Anthropic just dropped Claude Cowork—essentially Claude Code for everyone, not just engineers—and we got to chat about it with a product engineer at Anthropic who helped build it.In this live Vibe Che...

13 Tammi 1h 32min

AI in 2026: Reid Hoffman’s Predictions on Agents, Work, and Creation

AI in 2026: Reid Hoffman’s Predictions on Agents, Work, and Creation

From cofounding LinkedIn to backing OpenAI early, Reid Hoffman is in the habit of being right about the future, so we wanted to know what he saw coming in 2026.In his third appearance on AI & I, Hoffm...

7 Tammi 59min

Four Predictions for How AI Will Change Software in 2026

Four Predictions for How AI Will Change Software in 2026

Tomorrow is the first day of 2026, and to give our listeners a view of the trends that’ll shape the year ahead, Dan Shipper had Every COO Brandon Gell on AI & I to discuss their predictions for what’s...

31 Joulu 202537min

Best of the Pod: Reid Hoffman on How AI Is Answering Our Biggest Questions

Best of the Pod: Reid Hoffman on How AI Is Answering Our Biggest Questions

Learn how to use philosophy to run your business more effectively. Reid Hoffman thinks a masters in philosophy will help you run your business better than an MBA. Reid is a founder, investor, podcaste...

24 Joulu 20251h 1min

Attaining A Jhana Live: How Anyone Can Achieve Super Wellbeing

Attaining A Jhana Live: How Anyone Can Achieve Super Wellbeing

We recorded someone guide himself into a Jhana live on our podcast. And he narrated the whole process from start to finish.Jhanas are meditative bliss states and they traditionally require thousands o...

17 Joulu 20251h 15min