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Last Updated: January 16, 2026 Reading Time: 18 minutes Who This Is For: Skool community owners with 25-50+ members who want to turn engagement into revenue Why Paid Challenges Matter More Than Ever If you're running a Skool community with 25-50 engaged members but making less than $500/month, you're not alone. Most community owners treat their Skool groups like glorified Facebook groups—free value, endless engagement, but zero dollars in the bank account. The problem isn't that your members won't pay. The problem is you haven't given them something clear and time-bound to pay for. That's where paid challenges change everything. A paid challenge is a structured, outcome-focused program with a start date, end date, and specific transformation. It's not "join my community for general help." It's "join this 21-day challenge to launch your first digital product." This guide walks you through building and selling paid challenges on Skool in 2026—using AI to speed up content creation while maintaining your authentic voice. No fluff. Just the system that's helping community owners turn $0/month into $1K-$5K/month. What You'll Learn By the end of this article, you'll know: Why paid challenges convert better than traditional paid memberships for small communities How to design a challenge that solves one specific problem (not everything at once) Pricing strategies that work for community owners with limited audiences How to use AI to create challenge content without sounding like a robot The exact funnel to move free members into paid challenges Real numbers from Skool communities monetizing with challenges If you've been stuck giving away free value for months (or years), this is your roadmap to finally get paid. What are they getting access to? More of the same content they've been getting for free? Most community owners launch a paid tier and hear crickets because the value proposition is unclear. "Join my premium community" doesn't answer the question: What will I achieve?

I just interviewed Éva Raposa - Skool Games winner who built 366+ members and $30K+ MRR by refusing to follow guru formulas. Her approach? "Soul First CEO" - build your business around who you are, not what some 17-step system tells you to do. What Caught My Attention: → She won Skool Games WITHOUT cold DMs or aggressive pitches→ Built genuine loyalty - members tracked the leaderboard FOR her→ Her "missing tooth" experiment (yes, really) taught her authenticity > perfection→ Turned health crisis into $100K+ food coaching business using connection-first strategy Why This Matters for Monetisation: Most community owners copy tactics that don't fit their personality, then wonder why they burn out or fail to convert. Éva's path shows you CAN build sustainable revenue without feeling like a sleazy marketer. Her VIP tier ($99/month) filled naturally because members already trusted her authentic approach. Key Takeaway: Your monetisation strategy should match YOUR values and energy. If cold outreach drains you, don't do it. If you love deep conversations, build your revenue model around that. Watch the full interview: https://youtu.be/vlnfVVdnDNs Éva's Community: https://www.skool.com/connection/about?ref=c75adaa832e449d8b1ef463c22b1d8a9 Your Turn: What "guru tactic" have you tried that felt completely wrong for your personality? Drop it below - curious to hear what you've walked away from. --- Want more monetization strategies? 🆓 Free Community: Join 300+ community owners in Content Revenue Lab 💰 Paid Community: Turn 25-50 members into $1K-$5K/month → Skool Monetization Lab Connect with Des: LinkedIn • Facebook • Instagram • Instagram 2 • Substack