Is this a fit?
Build a thriving paid community around your expertise using Circle, Skool, or Discord — recurring revenue from members who pay monthly for access, accountability, and connection
Skills to bring or develop
- Community Building
- Content Creation
- Teaching
- Facilitation
The starting sequence
- Define your community positioning and unique value
- Set up platform and recruit 10-15 founding members
- Launch publicly with rituals and accountability pods
- Scale to 50+ members with referrals and content
- Add premium tiers and course/coaching upsells
Find your first customers
Treat this customer profile as a starting hypothesis. Talk to people in this role and find out what they already do, what it costs them, and whether they want help.
Role
Solopreneur or early-stage founder
Industry
Various — whoever shares your niche expertise
Problems to investigate
- Building alone with no one to bounce ideas off or get feedback from
- Consuming content but not implementing because there is no accountability
- Information overload — too many courses, not enough community and support
- Impostor syndrome and lack of confidence because they have no peer group
Channels to test
- Twitter/X
- YouTube
- Content Marketing
- Podcast
First launch approach
Build an audience of 1,000+ followers on one platform first. Create urgency with a hard deadline. Use DMs to personally invite your most engaged followers.
Ways to find your first customer
- Start a free community (Discord/Slack) to test the concept and build initial engagement before charging
- Run a free 5-day challenge on your topic to build urgency and demonstrate your teaching style
- Host a free live workshop, deliver massive value, then pitch the community at the end
- Personally DM your 20 most engaged followers and offer them early access
Content ideas
- Member success stories and transformations (with permission)
- Behind-the-scenes of running the community and lessons learned
- Free versions of community content (teasers that create FOMO)
- Day-in-the-life of a community member
Shape the offer & delivery
These are example packages to adapt, not current market rates or promises of sales. Choose one deliverable, set a revision limit, and test the scope with a real buyer before expanding.
Community Member
$29/mo example price
- Full community access
- Weekly group calls
- Resource library
- Member directory
- Async Q&A
Inner Circle
$79/mo example price
- Everything in Community
- Monthly 1:1 hot seat (15 min)
- Accountability pods (4-5 people)
- Exclusive workshops
- Early access to content
Mastermind
$199-$499/mo example price
- Everything in Inner Circle
- Weekly 1:1 access
- Private Slack/Voxer channel
- Guest expert sessions
- Revenue share opportunities
- In-person retreat invite
Build and deliver the offer
Audience & community
Structure outline
Section
Welcome / Start Here
Purpose
Orientation for new members — what this community is for, how to get the most out of it, and where to introduce themselves.
Section
General discussion
Purpose
The default open space for members to post questions and share wins.
Section
Wins & accountability
Purpose
A dedicated space for members to post progress — social proof and retention both come from visible momentum, not just content.
Section
Resource library
Purpose
Your curated templates, guides, and recorded sessions — the tangible "what am I paying for" artifact members can point to.
Section
Live events / office hours
Content cadence
Frequency
Daily
Content type
A prompt, question, or check-in to keep the space active — silence is the #1 churn driver in paid communities.
Frequency
Weekly
Content type
One piece of real teaching content (a lesson, framework, or template) — this is what justifies the recurring price beyond just "chatting."
Frequency
Weekly or biweekly
Content type
Live call — office hours, Q&A, or a workshop. Record it for members who can't attend live.
Frequency
Monthly
Content type
A themed challenge or focused sprint — gives the community a shared, time-bound goal.
Member onboarding
- Welcome message sent within minutes of joining — automate this, delayed welcomes measurably hurt activation
- Point new members to a specific "first action" (introduce yourself, post one goal) — a community with no clear first move sees new members go quiet and churn
- Personally @ mention or reply to every new member's first post for the first 90 days — this does not scale forever, but it should not scale away before the community has real member-to-member momentum
- Send a 7-day check-in DM asking if they've found what they were looking for — catches silent dissatisfaction before it becomes a cancellation
Moderation guidelines
- Post community guidelines publicly and pin them — most disputes are prevented by clarity, not enforcement
- Respond to any negativity or conflict within 24 hours — unmoderated tension is the fastest way to lose engaged members
- Protect the signal-to-noise ratio: redirect off-topic or purely promotional posts to a dedicated channel rather than deleting outright
Your launch roadmap
Work through the phases at your own pace. Durations and task hours are estimates; client conversations, sales, and other outcomes depend on the response you receive. Growth and exit steps are optional later decisions.
0 of 21 tasks checked
01 · Foundation 7 days · suggested pace
Define your community concept, choose your platform, and recruit founding members
Answer these questions: (1) Who is this community for? (3) Why will they pay YOU vs. consuming free content? (4) What can they get here they cannot get anywhere else? Write a one-paragraph manifesto that captures the community's soul.
Target deliverable: Community positioning document with manifesto, target member profile, and unique value proposition
Tool examples: Notion, ChatGPT
Planning allowance: 3 hours · AI can assist; review the output
Pick your platform based on your audience: Skool (gamification, simple), Circle (professional, courses), Discord (tech-savvy, free to host). Set up channels/spaces: Welcome, Introductions, Wins, Q&A, Resources, Off-Topic. Create community guidelines and a welcome flow that makes new members post within 24 hours.
Target deliverable: Community platform set up with channels, guidelines, and welcome flow
Tool examples: Skool, Circle, Discord
Planning allowance: 4 hours
Pre-load the community with valuable content so it does not feel empty when founding members join. Include: 5 resource posts (guides, templates, tools), 3 discussion prompts, 2 mini-tutorials, and your "Start Here" guide. Use AI to help draft, but add personal stories and examples.
Target deliverable: 30 days of scheduled content + Start Here guide
Tool examples: ChatGPT, Claude, Loom, Canva
Planning allowance: 8 hours · AI can assist; review the output
Personally reach out to your most engaged followers, email subscribers, or colleagues. Frame it as: "I'm building something special and want you to be part of shaping it." Do NOT launch publicly until you have 10+ founding members — an empty community is a dead community.
Target deliverable: 10-15 founding members committed (paid or confirmed)
Tool examples: Twitter/X DMs, Email, LinkedIn
Planning allowance: 4 hours
02 · Launch 14 days · suggested pace
Open publicly, establish culture, and hit 30 members
Run a 60-minute live call with all founding members. Introduce yourself, have everyone share their #1 goal for the next 90 days, and explain the community roadmap. Record this — it becomes social proof. End with action: everyone posts their goal in the community before leaving the call.
Target deliverable: Kickoff call completed, recording available, all members active
Tool examples: Zoom, Community Platform
Planning allowance: 2 hours
Set up recurring community rituals: Monday = Set Your Weekly Goal, Wednesday = Q&A Thread or Live Call, Friday = Win of the Week. These rhythms are the backbone of retention.
Target deliverable: Weekly rhythm documented and first 2 weeks executed
Tool examples: Community Platform, Notion
Planning allowance: 3 hours
Announce the community on all social channels. Use a waitlist or limited-spots model to create urgency. Share founding member testimonials (even if just screenshots of their intro posts). Run a free live workshop that funnels to a community pitch at the end. Email your full list with a 48-hour early-bird offer.
Target deliverable: Public launch executed, 15+ new member applications
Tool examples: Waymaker Social, Waymaker Email, Zoom
Planning allowance: 6 hours · AI can assist; review the output
Group members into pods of 4-5 people with similar goals. Each pod checks in weekly (async or live). Facilitate the first pod meeting, then let them self-organize.
Target deliverable: Accountability pods formed and first check-ins completed
Tool examples: Community Platform, Zoom
Planning allowance: 3 hours
03 · Growth 30 days · suggested pace
Scale to 50+ members with content, referrals, and retention systems
Launch a referral program: members get 1 month free for every new member they refer. Create a shareable "invite your friend" link. Give members social media templates they can use to share the community.
Target deliverable: Referral program live with tracking
Tool examples: Community Platform, Canva
Planning allowance: 3 hours · AI can assist; review the output
Invite an expert your members admire for a 45-minute live Q&A. This is surprisingly easy — most experts say yes because it is free promotion for them. Record and add to your resource library. These sessions are the #1 reason members upgrade to higher tiers.
Target deliverable: First guest expert session hosted and recorded
Tool examples: Zoom, Community Platform, Email
Planning allowance: 4 hours
Track weekly: active member rate, new vs churned members, weekly rhythm participation, and NPS score (survey monthly). If someone goes quiet for 2 weeks, DM them personally.
Target deliverable: Retention dashboard with weekly tracking, re-engagement DM templates
Tool examples: Google Sheets, Community Platform
Planning allowance: 4 hours
Turn community discussions into public content. Member questions become blog posts or tweets. Success stories become case studies. Q&A calls become podcast episodes. This creates a free content engine that attracts new members while serving existing ones.
Target deliverable: Content flywheel process documented and first 4 pieces created
Tool examples: Waymaker Social, ChatGPT, Waymaker Email
Planning allowance: 6 hours · AI can assist; review the output
04 · Scale 60 days · suggested pace
Hit 100+ members and build a sustainable community business
Define a small, measurable version of this task. Use your own customer evidence and actual costs to decide what to do next.
Target deliverable: Premium tier live with first 10 upgrades
Tool examples: Community Platform, Stripe
Planning allowance: 4 hours
As you approach 100 members, you need help. They handle: daily engagement, welcome messages, flagging issues, and facilitating discussions. This frees you to focus on high-value activities (content, growth, guest experts).
Target deliverable: Moderator hired and trained
Tool examples: Community Platform
Planning allowance: 6 hours
Run a 48-hour "annual plan launch" campaign to existing members.
Target deliverable: Annual plan configured and promotion sent
Tool examples: Stripe, Email
Planning allowance: 3 hours
Your community members are the warmest audience on earth for a course, coaching program, or digital product.
Target deliverable: Upsell product defined and pre-sold to community members
Tool examples: Waymaker Brain, Waymaker Courses, Email
Planning allowance: 8 hours · AI can assist; review the output
05 · Exit 60 days · suggested pace
Prepare your paid community business for sale, acquisition, or hands-off operation
Create comprehensive standard operating procedures covering every repeatable process in your paid community business — client onboarding, delivery workflows, billing, and support. A buyer needs to run this without you.
Target deliverable: Complete SOP handbook with video walkthroughs
Tool examples: Notion, Loom, Google Docs
Planning allowance: 12 hours · AI can assist; review the output
Record the questions this step raises for your business, location, and circumstances. Confirm requirements and assumptions with current official sources and a qualified professional before acting.
Target deliverable: Valuation estimate with supporting financials
Tool examples: Google Sheets, ChatGPT
Planning allowance: 6 hours · AI can assist; review the output
Organize all financial records, contracts, customer data, IP documentation, and legal documents into a virtual data room that a buyer or their advisor can review.
Target deliverable: Organized virtual data room
Tool examples: Google Drive, Google Sheets
Planning allowance: 10 hours
Identify every area where the business depends on you personally. Delegate, automate, or document each one. Test by taking 2 weeks off and measuring impact.
Target deliverable: Owner dependency scorecard (before/after)
Tool examples: Notion, Zapier, Slack
Planning allowance: 20 hours
Create a teaser document (blind profile) for your paid community business and either list on marketplaces (Acquire.com, Flippa, Quiet Light) or reach out directly to 5-10 potential acquirers.
Target deliverable: Teaser document + 5-10 buyer conversations started
Tool examples: Acquire.com, Google Docs, Email
Planning allowance: 8 hours · AI can assist; review the output
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Tools, budget & effort
These are tools named in the original playbook, offered as examples to evaluate. Check current capabilities, pricing, licensing, and data handling with the provider before subscribing. Start with the tools you already have.
- Skool
- Circle
- Discord
- Zoom
- ConvertKit
- Loom
Tools to evaluate
Item
Video call tool for live events/office hours
Make the numbers your own
Include setup, subscriptions, selling, fulfillment, revisions, support, and your time. Use your actual inputs and compare a cautious case with a better case.
Open the experiment calculator →AI roles & prompt templates
Assign a clear job, provide approved inputs, and review the result. These are role and prompt ideas; this page does not run AI or connect your accounts.
Community Manager
Draft this week's daily engagement prompts for the community
Content Writer
Draft an outline for this week's teaching content piece
Use the first task above as your opening prompt. Include your audience, desired output, constraints, and how you will judge quality.
Your first small test
- Choose one customer. Find five people who have the problem described in this guide.
- Show one useful sample. Ask about their current process, priorities, and objections.
- Offer a clearly scoped pilot. Agree on deliverables, a price to test, and what success means.
- Record the evidence. Track responses, costs, hours, and what the buyer actually used. Decide whether to continue, change, or pause.
Explore related ideas
Adapted from Ashley’s Waymaker side-hustle playbooks, imported October 15, 2026. This is a published snapshot, not a live connection to your Waymaker account. Source examples are planning material, not verified customer outcomes. Explore Waymaker.