What makes a community truly thrive, and why are so many memberships failing to deliver? In this episode, we’re joined by Vincent Pugliese, founder of Membership Freedom and author of The Wealth of Connection, to rethink how we approach online communities in 2025.
Vincent shares his philosophy of leading with connection instead of content, why smaller groups outperform larger ones, and how entrepreneurs can build communities that grow and last. He breaks down the mindset shifts needed for successful recurring revenue, how to build a membership people actually want to stay in, and why the most important strategy has nothing to do with tech.
We also explore Vincent’s “stadium model” for multiple income streams, how to set up a membership that doesn’t burn you out, and what inspired him to create the Unconference, an event designed entirely around hallway conversations.
If you’re tired of building content no one connects with or trying to scale a community that feels hollow, this episode is for you.
Key Points:
- Why “connection before content” builds better communities
- How to launch a membership without needing a big audience
- What most creators get wrong about platforms and tech
- The #1 reason people leave memberships—and how to fix it
- Building multiple income streams around one core idea
- How to create exit-ready memberships that aren’t dependent on you
- Why Vincent built an entire event around hallway conversations
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