What It Means to Live Well


Today, I want to announce the Alumni Mentor Corps – a program we’re building for Cohort 2 of The AI Second Brain, running September 17 to October 8.

Applications are only open to graduates of our founding cohort. But I wanted to share it with everyone anyway.

We believe in building in public, showing you the thinking behind what we create, not just the finished product.

This is a big part of how we're preparing for Cohort 2, and I think the vision behind it is worth your time.


Four Team Members Lived in Recall. This Is Their Verdict

Everyone has access to the same AI tools. Your edge is the context you feed it.

So I handed Recall, an AI knowledge engine, to four people on my team for three weeks of real work. One of them canceled a 10-year subscription on camera. All four hit the same surprising gap.

Here's their honest verdict.

This video is also available as a blog post that you can read here.


What's Your Most-Used AI Connector?

Last week, I asked how much you're spending on AI tools every month. Here's what came back:

  • About 1 in 5 of you pay nothing, and about 1 in 5 pay $100 or more.
  • On X, spending skewed much higher: 43% of respondents there are already at $100+ a month.
  • When people named specific tools in the comments, Claude was the clear favorite, well ahead of ChatGPT and Gemini.

That covers the spend side. What I'm curious about now is the setup side: which apps you've connected to your AI directly.

I just published a guide on Claude Connectors, the tools that let Claude tap into apps such as Google Calendar, Superhuman, or Notion. You can read it here.

Without connectors, I'd have to manually attach files to Claude every time. With connectors, Claude can tap into those apps directly and pull the data itself.

What's your most heavily used connector? Hit reply and tell me which one and what you use it for.


Living Well with Lauren & Tiago | Grief & Pizza Podcast

My wife Lauren and I joined Marie Poulin and Ben Borowski on the Grief & Pizza podcast recently. We talked about...

  • Our move to rural Mexico and what it's done for our nervous systems
  • Raising kids screen-free in a place that honestly feels like the '90s
  • What it looks like to work three to four hours a day and still feel like you're doing more
  • The annual review as a technology: a process disguised as an artifact
  • Why the rush to adopt AI is overblown
  • Why real human connection matters more now, not less

Free Event with Ramit Sethi Next Week

A lot of the money industry runs on keeping you anxious. My friend Ramit Sethi has spent twenty years working against that, and he's hosting a free live event called When Will I Be Rich? that I want to tell you about.

You probably already know his work: the New York Times bestseller I Will Teach You To Be Rich, Netflix's How to Get Rich, and his Money for Couples podcast.

Ramit will show you what rich means on your own terms and the systems that get you there.

If you're tired of being told to feel bad about spending, check this out.

Available Nov. 3, 2026

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Cohort 2 of the AI Second Brain is happening: September 17 to October 8. The Founding Cohort finished with an NPS of 70, and we've spent the time since making it even better. If you're thinking about joining, save those dates now to your calendar. And if you want to be the first to know when enrollment opens, join the waitlist at the link below. Join the Waitlist Your AI Gives Generic Answers? Here's the 3-Step Fix Most people give AI almost nothing to work with, then wonder why the answers...