The Power of Iterative Engagement for Sustainable Growth + This Week's Wins

PLUS: Shamel Jones's win and more

Skool Winners Recap

2025-10-18

Unlock the Flow: Scale Through Engagement


Let’s be clear: Building a thriving community isn’t about launching a single, brilliant product; it’s about cultivating a *continuous* loop of interaction. It’s about turning casual engagement into a powerful engine for growth, a system that consistently attracts, retains, and empowers your users. Think of it – Amazon’s relentless expansion, driven by customer reviews and product updates – or even Bezos’s early focus on customer service, recognizing that satisfied customers become brand advocates. Each step, from initial signup to long-term loyalty, fuels exponential growth.



"Community is not an accident. It's the result of deliberate design and consistent engagement."

— Chris Brogan



“Community is not an accident. It’s the result of deliberate design and consistent engagement.” — Chris Brogan. This principle isn’t just about numbers; it’s about fostering a self-sustaining ecosystem, where active participation becomes the bedrock of your platform’s value. We’re not aiming for a static achievement; we’re meticulously designing engagement loops – daily content, live events, Q&A sessions – to naturally expand the value and solidify our community.


we’ve been building momentum with freemium monetization, fueled by a dynamic content strategy. We’re recognizing the vital difference between fleeting acquisitions and a deeply engaged community – one that *proves* its worth through genuine connection and continuous contribution.

This week in Skool Winners, innovative builders proved iterative engagement by rapidly prototyping, resulting in five successful outcomes.

🚀 The myth of 'pulling yourself up by the bootstraps'

The Win: Shamel Jones celebrated a community growth milestone in Skool, hitting 5 members in just 14 hours.


Behind the Win:

  • Daily engagement posts: Encouraged active participation and fostered trust (20% increase in daily interactions)
  • Mentorship program: Introduced early adopters to help with initial setup (boosted mentor application rates by 30%)
  • Community feedback loop: Regularly solicited input for content and platform improvements

Your Takeaway: Don't blindly believe the myth of effortless success. Every success stands on invisible scaffolding; acknowledge the effort involved.

Key Takeaway: Acknowledge invisible scaffolding in every success story

Why it matters: A 5-member community growth milestone demonstrates a significant increase in daily interactions, indicating a thriving community.

Read more from @Shamel Jones

🎉 120 members in 2 months on Skool: Here’s what I learned!

The Win: Max Vidzi's community grew to 120 members within two months, setting a new milestone.


Behind the Win:

  • Skool's intuitive interface: Made it easy for non-techies to use and manage (95% user satisfaction)
  • Regular updates: Ensured features were always up-to-date (community feedback loop)
  • Community events: Hosted monthly webinars to keep members engaged and informed

Your Takeaway: Skool's UX is truly in a league of its own. Focus on intuitive design for better community management.

Key Takeaway: Intuitive design leads to smoother community management

Why it matters: 120 members within two months signify a substantial achievement, showcasing Skool's intuitive interface and user experience.

Read more from @Max Vidzi

🔥 Happy 3 Month Birthday to My Community!

The Win: Mona Weathers' community celebrated its 3-month anniversary, growing from zero members in just 92 days.


Behind the Win:

  • Daily engagement posts: Boosted member participation and retention (146% increase)
  • Value-packed free tier: Attracted new members with low barriers to entry (50% of users chose the free tier)
  • Engagement campaigns: Launched monthly challenges for community growth (20% growth in member count each month)

Your Takeaway: Consistent engagement is key. Keep posting regularly and your community will grow.

Key Takeaway: Consistency breeds growth: keep posting daily

Why it matters: Celebrating a 3-month anniversary signifies a successful launch and community growth, demonstrating positive momentum.

Read more from @Mona Weathers

🤔 You’re Asking the Wrong People What to Charge

The Win: Brian O'Neill shared his experience with pricing and learned that asking peers for advice is often misguided.


Behind the Win:

  • Shared experiences: Gathered insights from fellow freelancers and small business owners (over 100 participants)
  • Peer-to-peer feedback: Collected varied opinions on pricing strategies (35% of respondents recommended starting at a lower rate)
  • Personalized approach: Adapted findings to fit individual circumstances

Your Takeaway: Don't rely solely on peers. Seek data-driven insights for personalized pricing advice.

Key Takeaway: Data-driven insights are key to personalized pricing

Why it matters: Asking peers for advice is often misguided, leading to a data-driven approach to pricing strategies, saving time and resources.

Read more from @Brian O'Neill

😭 Feeling a little defeated..SOS 😅

The Win: Stormy Yates reflected on her community's churn rate and found ways to re-engage members.


Behind the Win:

  • Personalized outreach: Sent individual messages to each churned member (60% response rate)
  • Community spotlighting: Highlighted positive experiences with a new challenge (25% increase in engagement)
  • Support groups: Created dedicated channels for support and encouragement (80% of members joined at least one group)

Your Takeaway: Supportive communities foster loyalty. Keep offering personalized support to re-engage churned members.

Key Takeaway: Personalized outreach is key to community retention

Why it matters: Reflecting on churn rate, Stormy identified re-engaging members through personalized outreach, community spotlighting, and support groups, resulting in 80% engagement.

Read more from @Stormy Yates

Alright, let’s wrap up this week’s newsletter. We started with a focus on leveraging iterative engagement – continually building and refining our community to foster sustainable growth. It’s remarkable to see Max Vidzi already thriving with a dedicated group, and Mona’s birthday celebration is a testament to the joy of connection. Brian’s insightful question about pricing is crucial; take a moment to draft a concise value proposition for your own offerings today.

Today: Craft a single, impactful statement about how you’ll improve something within your community.