How to get your first 100 paying members (with 3 playbooks you can copy)
When Justin Moore launched the very first cohort of his brand sponsorship course, only three people signed up.
After weeks of late nights and telling his wife that “This is going to be big,” the results were crushing. But her response stuck with him:
“Big things take time to build.”
And she was right. Justin kept going. Today, he’s taught more than 2,000 students how to land brand deals and monetize their content through his Creator Wizard community.
That fear of starting small? Every creator feels it. You see peers celebrating $100K launches or 1,000-member milestones. But every thriving community begins with a few people willing to believe.
There’s no single path to your first 100 members. But there are proven ones. In this article, you’ll learn from founders like Justin and others who’ve built thriving paid communities in different ways:
- Andrew Petcash, founder of Profluence, a 1,100+ member community for sports business founders, investors, and executives
- Ayodeji Awosika, an author and TEDx speaker, grew The Writers League to 250+ members.
- Anna Tyrie, the YouTuber behind English Like a Native, built The Conversation Club, a 1,000+ member language-learning community.
You’ll also learn how to move from zero to 100+ members using Circle’s three-phase launch system, plus what metrics to track, mistakes to avoid, and benchmarks to guide your next move.
From zero to 100: a three-phase launch system to grow your community
Getting your first community members can feel overwhelming. You’re juggling platform setup, content, pricing, and promotion—all while wondering if anyone will actually join. Breaking your launch into three clear phases helps you stay focused and make steady progress, rather than trying to do everything at once.
Phase 1: Build your pre-launch foundation (0–25 members)
Start small and personal. Invite people who already know and trust your work, like friends, clients, collaborators, or superfans. Use short surveys, landing pages with waitlists, or pre-sell offers to test your idea and gather feedback. Keep outreach one-to-one through DMs, emails, and personal invites. These early conversations will set the tone for everything that follows.
Phase 2: Create your launch moment (25–50 members)
Once you’ve validated interest, it’s time to go public. Host a live kickoff event, send a short launch email sequence, or run a countdown to opening day. Add urgency with founding-member pricing or exclusive bonuses. Share early wins and testimonials to build credibility and show the value of joining now.
Phase 3: Sustain your growth (50–100+ members)
With your core group in place, shift focus to retention and organic member acquisition. Introduce weekly live sessions, themed challenges, or accountability check-ins to keep engagement high. Encourage referrals and make your events easy to share. Finally, refine your pricing with annual plans or premium tiers for your most active members.
Each phase builds on the last, turning early interest into active, paying members. This framework is also flexible. Adapt it to your strengths, goals, and audience.
Next, we’ll look at three founder playbooks that show how this system works in practice.
Build your community launch plan with Circle’s launch guide—in 5 days.
The distribution-first playbook for creators with a social following
Before he launched Profluence, Andrew already had a social media audience of more than 150,000 people. But that didn’t happen overnight.
“I’ve answered every X/Twitter and LinkedIn message I’ve gotten over the last three years,” Andrew says. “So, for me, the community we have now is really the result of four years of work leading up to this point.”
Andrew had also spent years sharing insights and building trust through his weekly newsletter, Profluence Posts, which now reaches more than 33,000 subscribers that he converted from his social channels. So when he invited his readers into a new community space, they already knew and trusted him.
Phase 1: Pre-launch
Profluence began as a free private space for portfolio founders and investors in Andrew’s venture fund.
“We learned so much from that early group,” he says. “They told us what wasn’t working and what they needed more of.”
When the founders’ employees started asking to join, Andrew knew the demand was bigger than his circle. That’s when he decided to open a paid version to the public.
Andrew’s key moves to try:
- Build a newsletter and social following before launch.
- Seed a free, private test space for your closest network.
- Use feedback to shape your paid offer.
Phase 2: Launch
With validation, Andrew launched publicly, charging $50/month or $500/year. To get his first 100 members, he leaned on the credibility he’d built through consistent content and one-on-one relationships.
He promoted the new community through his newsletter and LinkedIn, offering bonuses like a free sports-startup course and a list of 300 investors to add value and entice early sign-ups.
“We wanted to highlight the biggest problems like fundraising, networking, and tools, and show that we had the people and resources to fix them,” he says.
Within about a month and two short email launches, Profluence got its first 100 members.
Andrew’s key moves to try:
- Announce your paid community through channels you already own.
- Offer meaningful incentives that solve real member problems.
- Keep launches short and focused to drive faster conversions.
Phase 3: Growth
Once members were inside, Andrew shifted his focus to retention and connection. He added weekly news recaps, expert guest sessions, and specialized subgroups for fundraising founders and female founders. His team also messages every member personally once a month.
“Daily engagement is key,” he says. “That personal touch makes the space feel alive.”
Over time, Andrew layered in public-facing events like panels and pitch competitions to attract new members and energize the existing community.
Andrew’s key moves to try:
- Create consistent touchpoints like weekly sessions or subgroups.
- Keep outreach personal, even as you grow.
- Introduce public events later to expand reach and visibility.
Andrew’s launch approach is a reminder that every post, reply, and DM adds up. The community you want tomorrow starts with the relationships you build today.
👉🏼 Circle features that help run this playbook:
- Use email hub to share your latest news and insights
- Website builder to build a landing page for a waitlist or event schedule, and
- Host public events to attract new members beyond your core network
The email-led playbook for creators with an engaged list
After becoming one of Medium’s top writers with more than 120,000 followers, Ayodeji (Ayo) kept getting the same question: How do I do what you do?
“People started asking me, ‘How do I write articles and make money on Medium?’” Ayo says. “So I launched a course on making money writing on Medium, and that did really well.”
That success pulled him deeper into the business of writing: audience building, email marketing, launches, and client work. As his career evolved, so did his audience’s needs. This journey led him to create The Writers League, a space for writers to learn about every part of building a creative career.
By then, Ayo had built a 30,000-person email list by adding short CTAs to the bottom of his Medium articles. His subscriber base became the foundation for his launch and one of his most powerful member acquisition strategies.
Phase 1: Pre-launch
Before opening his doors, Ayo primed his list with an email series that followed a simple formula: Problem-Agitate-Solve. Each email introduced a pain point writers faced, dug into the frustration behind it, and hinted that a solution was coming soon.
Phase 2: Launch
When launch week came, Ayo ran a short, focused, week-long promotion with multiple emails on the final day.
Many creators worry about sending too many emails, but he stresses that with a launch, you’re not just promoting your own offer. You’re also in competition with other creators.
“People aren't just sitting at the inbox waiting for your emails,” he says. “They have tons of other things that they're subscribed to, so frequently communicating with that list is the best way to grow your community.”
He built urgency with founding-member pricing, bonuses, and a clear deadline. Within the first couple of months, The Writers League gained its first 100 members.
Ayo’s key moves to try:
- Keep your cart open for about five to seven days.
- Send several emails on the last day to create urgency.
- Use limited-time pricing or bonuses to drive conversions.
Phase 3: Growth
As The Writers League grew, Ayo doubled down on engagement. He now runs five-day challenges (like a newsletter set-up sprint) and virtual summits featuring six- and seven-figure business owners. These live experiences re-engage his community while also creating new content for The Writer’s League’s resource library, adding even more value to his membership.
Ayo has also scrapped month-to-month pricing in favor of annual memberships because he’s found that these members, “tend to stay longer, have a higher lifetime value, and get better results from what I teach.” He’s also introduced a $1,000/month group coaching tier for more advanced members.
Ayo’s key moves to try:
- Host short, outcome-driven challenges to boost engagement.
- Offer annual or high-ticket tiers to stabilize revenue.
- Use community events as engagement tools and member acquisition drivers.
Ayo’s success shows how consistent communication can turn engaged email subscribers into your first 100 members while keeping them invested long after launch.
👉🏼 Circle features that help run this playbook:
- Use email hub to keep your list warm with engaging updates
- Set up automations to simplify onboarding and ongoing communication
The live experience playbook for creators who thrive in real-time
Before launching her community, Anna Tyrie spent years building English Like a Native, a YouTube channel that makes English learning more personal and accessible.
“Learning English opens up so many opportunities for people around the world,” she says. “I felt there was a gap I could fill.”
She’s now grown her channel to over a million subscribers. But even with that success, something still felt incomplete. She kept seeing the same people return to comment and engage.
“They needed a place to connect with each other, not just with me,” Anna explains.
That realization led her to launch The Conversation Club, a private community where learners practice speaking English through live lessons, discussions, and challenges.
Phase 1: Pre-launch
Anna started by inviting her most engaged followers and former students to a private pilot group. This is where she tested her live sessions, refined her teaching format, and gathered testimonials.
“Before launching anything, I try to find out what people actually want and when they’re available,” she says. “What I think they want isn’t always what they actually need.”
She used quick surveys to understand her audience’s availability and needs, then built her events around that feedback. And before inviting anyone new, she made sure there was plenty of content waiting, so no one joined an empty space.
Anna’s key moves to try:
- Start with a small pilot group of engaged followers or clients.
- Ask your audience what they need and when they’re available.
- Prepare at least a month of content and events before launch.
Phase 2: Launch
Once she understood what worked, Anna hosted live workshops that previewed her teaching style and community experience. She recorded short clips from these sessions and shared them on YouTube to spark curiosity.
“I’m very British. I don’t like to sell,” Anna laughs. “So I’ll say something like, “I have a great time with these students, and they’re having a great time too. If you’d like to have fun while learning English, the link’s in the description.”
This gentle invitation worked. New members joined through her videos and newsletters, and engagement grew quickly.
Anna’s key moves to try:
- Host free or low-cost live events to showcase your community experience.
- Repurpose event highlights into social clips to attract new members.
- Share authentic student stories or testimonials. They sell better than any pitch.
Phase 3: Growth
As her community grew, Anna focused on consistency and connection. She introduced weekly live lessons, challenges, and interactive posts. Each day, members saw new idioms or prompts in the announcement banner and were encouraged to respond in the comments.
“Joining a community is a new habit,” she says. “You have to make it part of people’s daily routine.”
To encourage participation, she reached out personally to new members and rewarded every bit of engagement. Over time, these small touches have helped The Conversation Club grow to 1,000+ members.
Anna’s key moves to try:
- Anchor your community around live sessions and interactive challenges.
- Personally follow up with new members to build comfort and connection.
- Keep engagement active with daily or weekly conversation prompts.
Anna’s approach is straightforward but effective: keep showing up live, and your members will keep showing up for each other.
👉🏼 Circle features that help run this playbook:
- Use events to schedule live lessons and workshops that build connections
- Host them in live rooms to make interaction seamless and personal
Common mistakes to avoid on the path to your first 100 members
When you’re building your first paid community, it’s easy to overcomplicate things. Here’s what a few successful community builders wish they’d done sooner:
Start small.
ThinkMedia founder, YouTuber and coach, Sean Cannell, admits he spent too long building a massive “YouTube Academy” before launching. Now, he tells creators to launch one small, focused offer that helps members achieve a clear first result.
Teach less to help more.
Sean also warns against overwhelming new members with too much information. Instead of trying to prove your expertise, start by helping them build one actionable skill or habit that gives people a visible win—like generating topics for your YouTube videos.
Keep everything in one place.
Justin says his biggest mistake was scattering his courses, newsletter, and community across different platforms. Moving everything into Circle made it easy for members to see what else he offered and take the next step.
Price for commitment.
Across the board, founders agreed that underpricing backfires. A low price attracts less-invested members, while higher pricing creates accountability and longer-term commitment.
Key early growth metrics and benchmarks to track
Numbers don’t tell the whole story, but they can show whether your community is headed in the right direction.
Here are a few realistic benchmarks to aim for as your work toward your first 100 members:
- Phase 1 (0–25): Expect a 30–50% conversion rate from personal invitations or direct outreach.
- Phase 2 (25–50): Aim for 5–10% of your email list to convert into paying members.
- Phase 3 (50–100+): Healthy retention looks like 70–80% month-to-month, with 30–40% of members on annual plans.
Putting the launch playbooks into action
Getting your first 100 members takes time and a little trial and error, but you don’t have to figure it all out on your own. Now you have a step-by-step system and three playbooks to help you move from idea to a thriving, engaged community.
Every successful creator started with just a handful of believers and a clear mission to serve.
As Justin Moore reminds us, “Don’t be afraid to put in the work. It hasn’t been a hockey stick — it’s been a grind.”
Start with what feels most natural to you. Maybe that’s sharing your idea with your social audience and inviting them to be part of what you’re building. Or hosting a live session to give people a real taste of your teaching style and what it feels like to learn together. Or putting your email list to work by previewing what’s coming and building excitement before launch week.
Each approach can work because growth in a community isn’t linear; it compounds through connection, consistency, and care. What matters most is choosing the one that plays to your strengths and helps you build genuine relationships from day one. If you keep investing in the small moments — the DMs, the live sessions, the feedback loops — then those 10 early members will soon become 100 strong.
Start your 14-day free trial with Circle today to take the first step toward your first 100.
FAQs about getting paying members
How do I get my first 50 community members?
Start with people who already know, like, and trust you like clients, followers, peers, or subscribers. Personal outreach works best early on. Send direct messages, personalized emails, or invite people from your existing audience. Once you’ve validated interest, create a public launch moment (e.g., email series, live session, social posts) that clearly shows what your community offers and how it helps. Keep your cart open for about a week to build momentum.
Should I start my community free or paid?
If you’re still shaping your idea, starting free with a small pilot group can help you learn fast. Both Andrew and Anna used this approach to test content, gather feedback, and refine the experience. Once you’ve confirmed people find real value, transition to a paid model to attract more committed members and fund continued growth.
What events drive conversions for communities?
Live, interactive experiences consistently convert best. Founders like Anna and Ayo use free workshops, five-day challenges, or live Q&A sessions to give people a real taste of the community before joining. These sessions showcase your value and build trust, excitement, and urgency. Especially when paired with a clear next step, like a limited-time offer or founding-member bonus.
