Skool Stories How to activate your members (Live @ Skool Festival)
Mar 13, 2026
Calvin Hollywood, digital creator and community-builder known for creating engaged online communities. He covers onboarding tactics like personal DMs and profile-based welcomes. He discusses framing communities as connection-first, using levels and leaderboards to boost retention, cohort-based conversions, and smart freemium-to-paid funnels.
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Personalize Approvals With Profile Checks
- Do personalize approvals by reading membership answers and hovering profiles before admitting people to the free community.
- Calvin recommends asking three questions, checking profile pic/description and sending a 30–60s personal DM before approving.
Frame Community As Connection Not Content
- Frame the community as a place to meet and connect, not just consume courses, to attract community-minded members.
- Calvin observed conversion may fall but engagement and long-term retention rise when you sell connection over content.
Welcome By Name Then Hand Off Onboarding
- Send a short name-first welcome DM that thanks them and points out something you share in common, then hand off onboarding calls-to-action to your team.
- Calvin avoids heavy first-message CTAs to prevent pressure and follows up later with onboarding prompts.