Today I…

  • Scaled AI Makers Network's post-event engagement
  • Updated the project backlog
  • Updated the website
  • Launched a systematic outreach campaign that tripled our Discord membership from 3 to 10 active members in a single day

Today’s Challenge

The classic community builder's dilemma: how do I maintain momentum between in-person events?

People connect at meetups, exchange pleasantries, but then... nothing. The energy dissipates.

I needed to bridge that gap and create a "cozy web" space where conversations could continue without the time constraints of scheduled events.

My Approach

Personalized LinkedIn Outreach with Intent

Instead of generic "thanks for coming" messages, I crafted highly personal follow-ups referencing specific conversations from our last event. My guess is that casual syntax signaled authenticity (not automation).

Strategic Discord Onboarding

Rather than just dropping a Discord link, I connected people to ongoing conversations that directly related to what they'd discussed at the event. "Hey, there's a thread about AI coaching that would really benefit from your perspective on sequential learning paths."

Pricing Signal Strategy

For upcoming workshops, I'm testing a "normally $Y, but free for the first X people" approach. This plants the seed that value has a price while avoiding the rent-seeking trap (or, at least, impression) that kills early communities.

Key Insights

Medium-specific messaging that subverts norms positively

  • Text messages: Full sentences, proper grammar, emojis
  • LinkedIn: Intentionally casual, typo-inclusive. Read a lot like I was texting while running.
  • Discord: Structured but conversational, topic-focused

This wasn't planned. I noticed myself doing it intuitively and realized people probably respond better when the message format subverts their expectations for that platform in a positive way.

By “subverts” I mean it breaks the normal frame of thinking. I expect long-winded, jargon-filled rants on LinkedIn. When I see thoughtful messages in a Discord server, I sit up because it goes against the norm in a refreshing way.

The "Cozy Web" Beats the Open Web for Community

Discord represents that sweet spot between public social media and private group chats. It's invite-only but not exclusive, structured but not rigid. Perfect for building trust in an AI-savvy community where everyone knows how easy it is to automate "personal" outreach. Importantly, this has to be genuine to work.

Early Pricing Signals Prevent Rent-Seeking Backlash

Communities that start free and suddenly charge money trigger a visceral "what the heck" reaction. By signaling value and eventual pricing for some community features from day one, I attract people who understand sustainability while filtering out pure tire-kickers.

The Numbers

  • Discord growth: 233% increase (3 → 10 members)
  • Response rate: ~80% on personalized LinkedIn messages
  • Volunteer offers: 4 prior event attendees proactively asked how they could help
  • Thank you rate: 50% of last event’s attendees personally thanked me for organizing and facilitating ❤️‍🔥

What's Next

Planning the next in-person event (three weeks out) while developing the workshop format. The goal is creating a sustainable ecosystem where monthly free meetups (the "coffee cart model") stay funded by deeper, paid experiences.

Also prototyping a workflow to assist me document this building process using AI by turning voice notes into structured insights that can help other community builders.

Advice To My Future Self

Break the medium's social expectations in delightful ways

LinkedIn isn't email. Discord isn't Slack. Text isn't Twitter. The same content delivered with formatting that subverts users’ expectations in positive ways will dramatically outperform generic copy-paste or "just automate it, bro" approaches.

And if you're building a community around AI or tech, remember: your audience knows how easy automation is. Authenticity can be a powerful trust signal that you're actually human and actually care. Please don’t abstract it away.

The coffee cart model holds: charge less than Barstucks, create more value than Barstucks, make sustainable income part of the equation but not the whole thing, and build something people want to return to… not because they have to, but because they want to.

This is a Dev Log for the AI Makers Network. If this resonates with you, come say hi.