Where AI Trailmates is heading.

Right now: upleveling intermediate AI users.

We're starting with intermediate users. People who use Claude or ChatGPT regularly and are ready to go deeper into Co-Work, Code, or building their first agent.

We may eventually help beginners get to intermediate. That's a different program, a different format. The skill curve from intermediate to advanced is sharp, and that's where peer support has the most leverage right now. We're starting where we can do the most good.

What we're testing in this first cohort.

This first beta is a four-week test. We're paying close attention to a few things:

• Time. Does once-a-week work? 30 minutes, or 60? When does a trio feel like a chore versus the thing you look forward to?
• What makes a good match. Skill level matters, but so does timezone, schedule, what people are building, and why they're here. Our intake form is a first guess at the right signals. We'll know more after.
• Community size and shape. We want a Slack that doesn't feel like every other AI WhatsApp or Slack you've muted. Hyper-curated, high quality, low volume.

Where this goes from here.

The beta is where we learn. Long-term, we're hoping AI Trailmates becomes:

• The default place serious AI builders go for peer accountability.
• A small, curated community, not a 10,000-person Slack.
• More cohorts, more focus areas, more facilitators as the right people appear.
• Eventually, programs for companies and curricula that need real peer-supported AI literacy.

We're moving slow on purpose. We'd rather have a small group who loves this than a big one who shrugs.