We're Starting AI Second Brain Meetups


This fall we're starting AI Second Brain meetups!

The more time we spend with AI, the easier it becomes to go a whole day without a real conversation with another person.

These meetups are a small, deliberate push back against that: in-person gatherings for anyone building a Second Brain, or just AI-curious, in any city with someone willing to host.

​Read the full story.

Want to host one in your city? Volunteer by September 3. It takes five minutes: pick a date, a spot, and tell us why you're in.


Nick Milo Reads My Obsidian Vault Like a Doctor

Nick Milo has spent years at the intersection of Obsidian and AI. I opened my real, working vault and asked him to read it the way a doctor reads an X-ray.

What he noticed in the first ten seconds set up everything else we covered: how to back up your notes before AI touches them, the three files that make any AI model understand how you think, and why organizing still matters even when AI can search a messy pile just fine.


Why Details Are Your New Edge

AI is trained to smooth things over. Ask it to write about anything, and you'll get a vague, polished version, missing the texture that makes an idea memorable.

That means any detail AI hasn't trained on is becoming more valuable. A personal stash of information beats a perfect prompt.

A few ways to build one:

  • Read sources that aren't digitized: out-of-print books, niche publications, anything without an ebook version.
  • Look outside the present moment: History and science fiction both hold details today's models rarely surface.
  • Borrow from a different field: A detail from architecture or music can sharpen a business idea.

AI can only search and shape what you've already captured. No detail, nothing to work with.

Action step: Start paying closer attention to details, in conversations, in what you read, in daily life. Write down the ones that stand out, even the random ones. You won't know which matter until you need them.

Reply and tell me what you've noticed.


A Free Event From the Platform We Trust With Our Business

We were one of Circle's first customers back in 2020, and we're still on it today. Our entire business runs on Circle: courses, community, membership.

That's why I have no hesitation recommending their free Build Summit on August 25-26.

Day one brings six sessions from people who've built what they teach, including Chris Donnelly on keeping members engaged and Melyssa Griffin on staying true to your own vision instead of chasing what sells.

Day two is a live AI hackathon with Circle's team helping you build.

Whatever you've been meaning to create - a course, a membership, a business around your expertise - this is your chance to finally move past “planning” and into “building.”

Thanks to Circle for sponsoring this newsletter.


A Prompt Built To Hunt For What AI Misses

This month inside the Second Brain Membership, our theme is “Finding Alpha”: figuring out what's still worth your attention now that AI hands you the average answer for free. I wrote up the idea here.​

One of our members, Tobias, took it further than I did.

He built a research prompt that runs in eight phases, with a stop after each one. It won't invent sources, and it discounts any dissenter that peers never bothered to refute. It ends with a reading list of primary sources it refuses to summarize for you.

That's exactly what this theme is supposed to produce. Read Tobias's post and grab the prompt for yourself.

Available Nov. 3, 2026

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