AI Trailmates
Shut down in September 2026.
A free program and community for non-technical knowledge workers teaching themselves AI without a technical partner or a community. It had self-hosted signup forms, a member portal, a skill-based group matcher, a locked email template and a Slack coach. It came before What Are We Building, and turned into it.
The story
Frances and I tried learning AI alone. Then we just met up, and it worked so much better that we built a community around it. AI Trailmates started in April 2026 as a free, peer-to-peer community that put people at the same AI level into small groups, so nobody had to learn alone. It grew to 166 builders.
Running it taught us that the best part was people showing each other what they had built. In September we shut it down and kept that part: it turned into What Are We Building.
- Launched
- April 2026
A few tips
- I built my own signup forms (a web page, a small server function and a database) instead of using a form tool, so every signup landed in a database I own.
- Shrink photos when people upload them. Member headshots alone used up our free database bandwidth.
- Lock one email template. Three different looks went out in one week before we did.
Related files on this desktop
Tools I used for this project
