Welcome Dear Bri, an advice column for community conundrums, fiascos, and drama. In this episode, we’re hearing from Anxious in Atlanta. Their dilemma? They launched a free, private online community as a test—engagement was strong, but now they’re left wondering: Did they use up their one shot at launching a paid community?
To help Anxious navigate this transition, I brought on Evan Hamilton, the incredibly thoughtful and seasoned community manager behind programs at HubSpot, Reddit, and Nextdoor. He’s spent 15+ years in the digital communities space and brings deep wisdom around community building, discovery, and what to test (and when).
If you're in the early launch or discovery phase of a brand community, this episode is packed with insights to help you avoid the most common mistakes in community building—especially when moving from free to paid. You'll also hear why the key to a successful community strategy for online businesses might be focusing less on "community" and more on the actual outcomes your members want.
In this episode:
(05:11) The communitea: Anxious in Atlanta’s letter
(07:29) Evan’s own flop in launching a community strategy that didn’t land
(11:45) The 10/30/90 framework for better internal alignment
(15:06) The difference between testing engagement vs. willingness to pay
(19:12) The emotional pitfalls that cause builders to stay in free mode too long
(24:22) Micro-testing paid community management tips with events
(27:31) Why connection is the most mis-marketed part of a community-building offer
(37:43) Transitioning from free to paid without losing trust
(40:25) Boundaries in paid communities
(45:18) The growing trend of curated, smaller online communities
(49:37) How to set transparent standards for community roles and responsibilities
Expect: Online community building best practices and practical marketing strategy for communities.
Resources Mentioned:
📕 Check out the book Evan mentions: Predictably Irrational by Dan Ariely.
📩 Subscribe to Evan’s Newsletter Community Manager Breakfast.
❤️ Signup for Heartbeat. Bri’s recommended all-in-one community platform.
💛 Join Ember. The place for go-getter community creators building community-powered businesses.
Evan Hamilton
🖥️ Website
Bri Leever
🖥️ Website
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