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Wandering Aimfully Through Running A Business

Setting Up, Running, and Growing a Paid Community

An in-depth guide for what it takes to run a paid online membership community.
Jason ZookJason Zook Jason ZookJason Zook

Written by

Jason Zook

Table of Contents



Our Paid Membership Community Context


Step #1

Solve A Specific Problem


Step #2

What is the Product and Structure?


Step #3

Create an Awesome Onboarding Experience


Step #4

A Warm Welcome for a Paid Community is Important!


Step #5

Drop New Customers into an Automated Email Sequence


Step #6

YOU have to Show Up Consistently


Step #7

A Good Paid Community Should Have Accountability


Step #8

Selling and Marketing Your Paid Community



We LOVE Our Community (and Reasons Communities Fail)

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Setting Up, Running, and Growing a Paid Community


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We’ve been running a paid membership community since 2018, and in this article, we want to share everything we’ve learned (and help you avoid our mistakes!)

The first thing you have to realize about starting a paid community is that your potential customer doesn’t wake up and think, “I wish I could join a paid community today!”

That would make our jobs really easy. But alas, it’s not how life goes. Instead, your potential community customer is thinking, “I have X problem and I need a solution to that problem.”

This is why Step #1 to creating a paid community that keeps people engaged and paying is to define what problem your community solves.

But before we jump into that, some quick background on us and our paid community…

👋 Some (hopefully helpful) context before we move forward:
  • We are Jason and Caroline Zook 👩🏻‍🦰👨🏻‍🦲, a husband and wife team who, together, run our paid community with zero employees and we aren’t trying to grow a humongous business.
  • We started out selling multiple online courses and got tired of always feeling like we were promoting another thing, so moving to a paid community made logical next-step sense.
  • Moving to a paid community helped us build a more predictable revenue model for our business (although it is a bit harder to sell).
  • We sell a $2,000 “membership” (people can pay via 2 payment options: $100/mo or $400/mo). Once they pay $2k they are lifetime members and don’t pay us again.
  • We’ve had over 700 members join since 2015 (our “community” became official and a priority in 2018).
  • Our membership product has evolved multiple times and certainly had its ups and downs as far as sustaining growth and clarifying the problem our community solved.
  • We feel we’ve really hit our stride with offering monthly live coaching calls, a suite of previously-created courses/workshops, a private Slack channel, and some other goodies.
  • We preach an anti-hustle mindset AND admit we aren’t for beginner business owners. We can best help folks who have existing online businesses, focusing on digital products or creative client-services.
  • Current monthly recurring revenue (MRR) as of publishing this article: $21,500
  • Current membership churn rate: 5.4%
  • If you want to view our sales page on how we position and sell our paid community, you can check that out here.


Step #1 to Creating A Great Paid Community: Solve A Specific Problem

Your paid community is only as strong as the specific problem it solves AND the people who join.

If you don’t want to help people start a business from scratch, make that messaging VERY clear on your sales page and promo for the community. “This is NOT the membership if you’re just starting a business.”

The more you can attract the right members for your community, the stronger the community will be because everyone is around for the same purpose/focus.

The more you can attract the right members for your community, the stronger the community will be because everyone is around for the same purpose/focus.

Let’s look at a fictitious example company that wants to transition from selling courses to selling a paid community…

We’ll call this company Rocket Lab 🚀 and right now they have the following things going on in their business:

  1. They have an email list where they send weekly-ish updates with blog posts, videos, and how-tos related to growing online businesses
  2. They post helpful content on Instagram and YouTube around the topic of optimizing your business
  3. They have a handful of online courses around individual online business topics (Productivity, SEO, and website optimization)
  4. Rocket Lab’s 🚀 owner is excited about the idea of a paid community because it will A) help bring more predictable income to the business and B) help this owner feel more connected to their customers

Where many companies (fictitious or not) run into their first problem is assuming their customers simply want to join a paid community because they offer it.

The problem you solve for your community will change over time.

❌  The specific problem you’re solving is not to simply create a community around your website and email list; Your community should be about solving problems you’ve already solved and want to help others solve.

✅  In the example for Rocket Lab 🚀, the specific problem is helping people optimize their online business. Optimization comes in the form of (but not limited to):

The problem you solve for your community will change over time, that’s great. Your goal is not to pick your forever-problem right out of the gates; it’s to pick ONE problem that can get the community going and attract your first paying customers who aren’t just your friends.


Look at your current business and identify the specific problem you are already solving through your content (articles, videos, emails, courses, etc). Offering a solution to that problem is how you position a paid community to your ideal customers. If you have no clue what problem you solve, send out an email or post a question on Instagram asking people what problems you have helped them solve and look for the patterns!


Step #2 for a Paid Community: What is the Paid Community Product and Structure?

Once you’ve clearly identified the problem your paid community will solve, it’s important to create a structure that your customers will understand.

Will you be offering monthly live calls?
Will you be creating monthly worksheets/homework?
Will you be releasing new courses/workshops every quarter?
How will the community interact?
How often will you communicate with the community?

How we structure our Wandering Aimfully paid community

To best illustrate how we think about structuring a paid community, we’re going to share how this has evolved for our own biz.

🔄 Ongoing content: Monthly live coaching calls based around one business topic

From our experience, the best thing you can have with a paid community is a monthly focus and content that supports it. This keeps your members coming back for what’s new, and the more your members actually USE your membership, the lower your churn will be. For us, this means a 2-hour live coaching call we do with our members every month (on Zoom, obviously).

Jason and Caroline Zook Coaching

We aim to do three things on these monthly calls:

  1. Give our members ONE thing to work on in their business
  2. Give our members a time to connect live with us and each other
  3. Give our members a concrete “thing” they know they are paying for and can get value from

One of the biggest lessons we learned when we didn’t have ongoing monthly content early on with our paid community was that people didn’t know why they should stick around.

One of the biggest lessons we learned when we didn’t have ongoing monthly content early on with our paid community was that people didn’t know why they should stick around.

We created a “Coaching Hub” page within our members-only dashboard (more on that next) where we keep all previous monthly calls and have a call out to the next month’s call.

Wandering Aimfully Coaching Hub

🎓 A members-only dashboard: A place where members can find everything they have access to (and other members)

Like everything else in our membership, this has evolved over time. What started as a very simple password-protected page with a few links to click, has turned into a completely custom-built dashboard.

Our custom dashboard’s biggest feature is not just the listing of all the content available to members, but the ability to save that content to their own profile and to add comments to it (for their eyes only). We also have a directory of members that’s searchable, as well as interactive checklists based on different topics. Here’s a walkthrough video we created that shows our members-only dashboard in action:

Note: We would highly recommend NOT going the custom-built route until you outgrow the existing membership dashboard tools out there. We don’t have experience with them, but we’ve heard great things about Mighty Networks, Podia, and Circle for creating member dashboards.

📬 Consistent communication: We like sending monthly emails

This is a really EASY one for us because we always have a monthly coaching call we’re emailing our members about (to register for, get excited about, etc).

From time to time we’ll throw an extra email or two in, especially when we’re working on new products or other announcements for our members. The key is simply to show up and remind your members you are bringing value to them consistently.

Wandering Aimfully Members Only Emails

🤝 A private Slack channel: Where everyone can hang out AND our members can get access to us

We’ll talk more about access and accountability later in this article, but having a dedicated place for conversation and connection is a must-have for a paid community.

We choose Slack because we don’t use Facebook at all. We know people spend their time on FB and Facebook Groups can be a popular place to create community, but it’s simply not for us. We’d rather have a bit less participation in our community knowing that if folks are logged-in to Slack, they are focused on being in our community and not the million things FB wants to throw in their face.

Wandering Aimfully Members Only Slack

To recap, here is the structure of our paid community and what they can expect from us (and what they are paying for each month):

  1. 🔄 A monthly live coaching call
  2. 🎓 A dashboard to access members-only materials
  3. 📬 Consistent communication from us via email
  4. 🤝 A private Slack channel to hang out with us and other members

What is the structure of your paid community? What are the concrete items your customers can expect to get from you and from their membership?


Step #3 for a Paid Community: Create an Awesome Onboarding Experience

Just like anything in life, first impressions matter. If someone buys something from you and you drop them into an overwhelming black hole of content they’re going to get analysis paralysis 😩😩😩.

Instead of dropping your new customer into a black hole, create a set of thoughtful next steps for your new community members and educate them on how to get the most value from your community.

What happens RIGHT after the initial purchase?

Right after your customer pays is the single most engaged moment you’ll ever have with them.

This is the moment your new customer is the MOST engaged they will ever be in your community. Take advantage of this opportunity and lead them where you want them to go.

For us, we do the following:

🤔 Post-purchase page survey

On the “thank you” page after they finish paying, we have an embedded Typeform that asks a bunch of questions so we can get to know them better. Probably the most important question (selfishly) we ask: What was the ONE decision that led you to join today*?

Here are all the questions we ask if you want to steal our survey with pride:

*Our selfish question helps us write better sales copy because it shows us why paying members ARE joining (not just why we think they’ll join).

Wandering Aimfully New Members Survey

➡️ Post-purchase page next step

We have a BIG, BOLD, NEXT STEP item under the embedded survey. For us, this is to go open the Welcome Email they received which actually has five additional next step items. We tested this and found the act of going to their inbox as the next step performed better than overloading them with the additional five tasks on the thank you page.

Wandering Aimfully New Members Next Step

📧 Welcome email

Our welcome email has the aforementioned five tasks in it:

  1. The first is to go through our members-only dashboard walkthrough videos (more below).
  2. The second is a technical thing to give access to all our courses/workshops.
  3. The third is to join Slack and read our mini Slack guide.
  4. The fourth is to start our Getting Started Checklist (more on this next).
  5. The fifth is to reply and give us a virtual high-five (we include a high-five GIF of us in the email for fun and added personality).

Note: If you’re creating any sort of documentation on how to engage in the community itself (Slack for us), make sure to include some “Community Etiquette” and guidelines for people. For us, we like to make it very clear that our community is a safe space for people of all races, colors, gender, amount of money they make, etc.

Wandering Aimfully New Members Welcome Email

☑️ Checklists are wonderful!

We have a 20-item interactive checklist someone gets when they join Wandering Aimfully. 20 items may seem like a lot, but the first 10 are simple things like visiting X page of our dashboard, or creating a profile name, adding a profile photo, or filling out a bio, etc.

Then, as the checklist goes on, you want to help people learn where things are and how to get access to the content that will help them solve their problem. You don’t need to explain EVERYTHING to them, just point them in the right direction.

YOU will always be extremely familiar with how your community and the content within it exist. Your new customers will have no clue.

Wandering Aimfully New Members Checklist

Pro-tip: We have two important checklist items at the end of the list that create momentum… 1️⃣ We tell people to introduce themselves in our #introduce_yourself Slack channel and 2️⃣ We tell them to send me a direct message on Slack to say they’ve completed their “Getting Started” checklist.

You will always be extremely familiar with how your community and the content within it exists. Your new customers will have no clue.

📺 Create walkthrough videos of your community and its parts

Recording videos can be overwhelming but you don’t have to create anything fancy here. Break each part of your community down with short explainer videos and just use a video recording service like Loom.com to show your screen.

Go over these things in individual videos:

Again, you’re going to think all of these things are super easy and straightforward, a new customer is going to be looking for step-by-step guidance.

Don’t skimp on making these videos fun, they should reinforce your personality and how different your community will be going forward!

Wandering Aimfully New Members Dashboard Tour

🗺 Give your customers a roadmap through your products/content

It’s easy to overthink and overcomplicate creating a roadmap through your members-only content (especially early on because you want to over-deliver). But, a roadmap can simply be a Google Doc that walks people through each step of a process (or content/courses) you want them to go through to get the desired outcomes you want for them.

Let your roadmap be fancy later on, in the beginning just have it be a compass to point your new customers in the right direction. Let them know, from your experience, what things they need to do and in what order.

For example, let’s bring Rocket Lab 🚀 back and look at a sample roadmap:

With each step of your simple roadmap, you want your customers to feel like they have a DIRECTION to go in. Otherwise, they’ll see all the content they have access to and go through none of it.

Evolve your roadmap as your community grows, as you add more content to it, and as you find more problems to solve.


Think through and write down what your new customer onboarding experience should look like. What do you want them to do right after purchase? What is the next action to take? Do they have walkthrough videos of the members-only dashboard and a simple roadmap to follow?


Step #4: A Warm Welcome for a Paid Community is Important!

Joining a new community is like being the new kid in school all over again. You feel like you’re clutching your backpack, standing in the corner, nervous to put yourself out there.

Give new members specific steps on how and where to introduce themselves

We give our members the task of introducing themselves in our Slack channel and we give them a set of questions they can answer in their intro if they’re not great at intros:

Then, we encourage them to say hello to another member or two after they’ve introduced themselves. This helps create more introductions and connections!

As the community owner, you should be one of the first people to welcome them and encourage more folks to do the same.

Spark community engagement with your manual effort!

So many business owners are obsessed with automating or scaling right out of the gates, but there’s no substitute for that unscalable human touch. Believe us, members will remember if you go that extra mile to welcome them.

Feel free to direct message existing members and encourage them to say hello to new members that have just introduced themselves. Remind the existing folks how good a warm welcome felt to them and how they can pass those good vibes along.

Pro-tip: We like to do a “Re-Introduce Yourselves!” post every 4-6 months in our introduction Slack channel. This is a great way for everyone to give an update of what’s new, or to say hello for the first time.


How will you create a warm welcome for your new members? What specific steps can you give them to introduce themselves and have a set of questions to write their introduction without feeling overwhelmed?


Step #5: Drop New Customers into an Automated Email Sequence

Even the most engaged new customer is going to lose interest without some sort of nudge to come back.

Your job is to anticipate this drop-off and create ways to bring them back in. Using an automated email sequence is a great way to do this! 🤜💥🤛

Our example automated email sequence for new community members

This is our 7-email automated sequence. We’ve tested a few different emails as well as the timing of emails over the years and this is what we’ve landed on that seems to work the best at keeping new members engaged. Feel free to tweak this to what you think is best for your community!

📬 Email #1: Immediately after purchase [Welcome email]

This is the Welcome Email we described above (with the five tasks). Remember, this is a very exciting moment for your customer so don’t skimp on your excitement for them!

📬 Email #2: 1 day after purchase [Checklist reminder]

In this email, we like to try to create a dialogue and see how our initial onboarding experience went the day before. This email is short, sweet, and simply asks them if they’ve checked out our “Getting Started Checklist” (with a link to it) and if they have any questions.

📬 Email #3: 3 days after purchase [Roadmap and your goals]

Remember that roadmap we talked about in the previous section? That’s what we highlight in this email. We make sure they know about the step-by-step plan we’ve created for them to get the most value out of the community/membership. We also include a question in this email to reply with three goals for the next 6 months (related to money, life, and fun).

📬 Email #4: 1 week after purchase [Money exercise]

We love giving new members our expense and debt organization exercise in our welcome email sequence. This exercise has helped 75% of our members find enough money in their current expenses to cut which will pay for their membership! It’s a huge win for them to feel like we just helped them pay for the community. Also in this email, we ask them to reply if anything has overwhelmed or confused them about the membership after their first week. Think about an exercise or small win you could offer new members to really get that sense of momentum for them and get them used to taking action. Again, remember, the more action steps your members take, the less likely they are to churn out.

📬 Email #5: 2 weeks after purchase [3 articles]

We have 3 “cornerstone” articles that we send to our new members to get a feel for who we are, what we stand for, and what matters most to us that we’ve learned from years of experience. We also ask them to reply in this email with any ah-ha moments so far in the membership.

📬 Email #6: 3 weeks after purchase [Are you stuck?]

We ask them to reply if they’re stuck or feeling overwhelmed. From their replies, we can guide them back into our roadmap, a previous coaching session, a community channel in Slack, or just to help via email.

📬 Email #7: 4 weeks after purchase [What’s next?]

We conclude the welcome email series and let them know what they can look forward to each month moving forward and a reminder of where to find everything (links to the members-only dashboard, Slack channel, etc). We also let them know how often they can expect to hear from us moving forward (weekly on Mondays with our normal newsletter and monthly for members-only coaching sessions).

Pro-tip: In nearly every email in the automated sequence we add a “ps” at the bottom that includes a note to head into our Slack channel and engage in ONE conversation with another member. This does a great job of sparking more discussion and people meeting one another.


Write out your automated welcome email sequence for your new members. If you’re going to use our 7-email series, customize the emails to fit your paid community offerings!


Step #6: YOU have to Show Up Consistently

If you’re trying to build a “passive income” business, a paid community is NOT that.

You are a big part of the reason someone is buying so if you don’t show up, you should expect a pretty high churn rate (aka your members canceling quickly).

Preface to this section: We realize you may not want to run your community 100% of the time and that you may hire someone to do this for you. While that’s a completely reasonable option, from our experience, members are more active and participate more when the person they bought the paid community from is available. If you have a community manager and you aren’t available to your community, know that this might affect the activity and engagement.

What is YOUR bare minimum participation?

Running a community doesn’t have to be a 24/7 job, but it IS important that you define when you will devote time to the community to establish a reasonable expectation from your members. We engage with our community during standard work hours of 9-5, Monday-Friday. Now, your amount of participation is completely up to you and if you want to be less available, the least you can do is communicate that to your members.

For example, maybe you only want to be available from 9a-11am, Monday-Thursday? That’s completely up to you. But, just know, the less you’re around to spark conversation and engage (especially early on!), the less engaged your community will be.

I like to think of being in Slack as my “full-time” job

When I say “full-time” job I don’t mean I spend 40 hours per week monitoring our Slack channel. What I mean is this is the task on my to-do list I spend the majority of my time on (and I enjoy doing it!)

By being available for DMs, new conversations, and answering every question first, I show our community members how much the community means to me. This participation does NOT require 8 hours per day, 5 days a week, it’s just about keeping Slack (for us) open and making sure my schedule isn’t too overloaded that I can’t be available.

This works for us because typically my wife and business partner Caroline is doing the more high-focus, creatively-driven tasks that require deep work. This is what allows me to manage the operational tasks and juggle that with community engagement with no problems.

We can’t count the number of messages we’ve received from our members who are genuinely surprised at how active we are in our Slack community. That, in itself, is a great differentiator for our paid community versus others.

Create a community content calendar to spark engagement

You don’t need us to share how important a content calendar is. But, having one dedicated to engaging with your community is really helpful (especially early on). Your content calendar could be as simple as a weekly post you create within the community around a big question/topic/etc.

This spark of engagement not only encourages people to interact, but it shows that there is a leader in the group who values people’s ideas and thoughts.

Some weekly prompt ideas to get you started on your own community content calendar:

Feel free to go outside your niche with weekly prompts and be okay with engaging in some unique discussions as well. For example, when the Social Dilemma movie took off, a week of conversation naturally happened in our community around it (some folks even had a group watching party!)

IMPORTANT: What is the recurring content that will keep people around each month?

We already talked about this in-depth in Step #2, but felt it was helpful to bring it back around in the context of community engagement.

👉 Are you hosting a live coaching call each month?
👉 Are you doing a group Q&A call each week/month?
👉 Is there a new project you’re working on and you have some sort of group check-in on Fridays?

Whatever you decide, make the recurring content crystal clear for your members. Make sure they know what to expect and this will keep them engaged and paying.

Note here: Don’t back yourself into a recurring corner you can’t keep up with. Also, remember the value you’re offering and the price people are paying. You don’t need to create a new course every month if someone is only paying $20/month.

YOU are going to be intimately familiar with all your plans for your community but you have to remember your community members do not live inside your brain. Be explicit and share exactly what they can expect.


Decide on the amount of community engagement you can offer your members and make that clear to them. Plan content to create conversation and interactions with questions you’ve thought of ahead of time. Make it easy for members to have weekly/monthly prompts to discuss the ongoing content they receive.


Step #7: A Good Paid Community Should Have Accountability

There are many ways to create accountability in a paid community but we’re going to focus on two: Accountability created by you and accountability created by members.

1️⃣ Accountability created by you

One of the BEST things we did for our community was to create a simple accountability system called Momentum Mondays. The way this works is extremely simple:

Some members have done Momentum Monday check-ins with me for over a year and a half, while some only last a few weeks. It’s not about making them feel guilty if they can’t keep up with the check-ins, it’s just about carving out space to be accountable to someone.

⭐️ We’ve heard from the majority of these folks that these direct accountability check-ins are the main reason they continue to pay for their membership.

Pro-tip: I have a Google Sheet where I keep track of people’s weekly check-ins. I color-code it based on if their check-in was more positive, negative, or if they missed their check-in. I also create a highlight color for really good weeks so I can bring those good weeks back up when things naturally dip into a bad week later on (happens to all of us). This sheet is also really helpful as I’ve found 30% of people forget to check-in, so it’s easy for me to remind them.

Wandering Aimfully Momentum Mondays

2️⃣ Accountability created by members

Our members love creating small groups where they can work through a specific course or problem together. These groups tend to be self-facilitated and usually don’t get larger than 3-8 people.

You should encourage folks to create these groups since it probably won’t happen early on.

If we go back to Rocket Lab 🚀’s community, they could do the following to help spark member accountability groups:

Also, feel free to tell members you’d love for them to create these groups on their own. It may happen organically, but a little nudge doesn’t hurt (especially early on)!

Note: I tend to stay out of the small accountability groups as I don’t want them to feel pressure from me at all.

If people don’t get value from your paid community they’ll churn out quickly

This seems like common sense, but if you don’t have a plan to create accountability for your members, they’re going to leave. All the monthly calls, new courses, Q&As, emails, etc, aren’t going to keep members if they aren’t feeling cared about in some way.


How will you make sure you’re setting up a system for accountability early on? What will YOU offer and what will you encourage your members to do to be accountable to one another?


Step #8: Community Growth aka Selling and Marketing Your Paid Community

You are already aware of the length of this article and we could (and have) written other articles just as long as this one about marketing and selling. There is A LOT that goes into marketing and selling any product or service but a paid community has its own unique challenges which we’ll cover here!

💰 Sales: How are you going to sell and grow the community?

For us, we’ve found that open/closed launches work really well and help us reach our enough goals with our business.

If you aren’t familiar with an open/closed launch, it’s very simple. You just open the “cart” for X amount of days, making your membership available for purchase. After those X days have passed, you then close it down and make it unavailable again. We like doing bi-annual open/closed launches that last 14 days each time (Spring and Fall).

Why we like open/closed launches to sell our paid community

There are two factors that work in our favor with open/closed launches:

  1. We get to control the growth of the community on our terms and our schedule (it never feels out of our control 🤪 to have new members coming in all the time).
  2. We don’t have to be in sales and promotion mode all the time! We only have to focus on this twice per year 🙌.

This what our community growth has looked like from the beginning:

You can see the specific spikes in new customers when we did open/closed launches in 2020:

Wandering Aimfully 2020 New Customers Chart

What about creating a “passive” sales funnel to sell a paid membership community?

We’ve tried creating a passive sales funnel on many occasions and in all our time of building online businesses we’ve never found those attempts to be truly passive. It always requires ongoing tweaking, testing, and (a lot of times) money for paid advertising (which we’ve tried in the past with other business ventures and we don’t enjoy doing it).

Knowing that our paid community is a $2,000 lifetime product, it’s a bit harder to sell through a series of emails.

We DO have a passive funnel (free quiz > email series > short sales pitch) and it does sell a handful of membership spots here and there but it’s not something we rely on (we see it as gravy on top).

This is one area where we are happy to admit that we are NOT experts and don’t have secondhand knowledge we’re going to copy and paste to you. Instead, we’d rather be honest and say we haven’t figured this out for our specific paid community.*

*And, our open/closed launches bring us enough new customers to meet our goals so we don’t have to (thankfully) worry about it.

Other “passive” sales tactics we’ve tried have worked in varying degrees

Now that we’ve shared our caveat about passive sales funnels we also want to share a few other experiments we tried over the years to grow our community.

🧪 #1: Test Drive Experience (Best Results) – We created a “Test Drive” of our paid community by building, essentially, an online course that anyone could view. In the course lessons, we had short videos that highlighted different parts of our membership. Then, a “lesson” in the course pitched our membership to the person taking the test drive. We found this experiment worked REALLY WELL for about two months… And then it stopped working. Our hypothesis (and thoughts from fellow community owners) is that the folks who bought were already interested and the Test Drive converted them to paying customers. But, for complete strangers, it didn’t convert well at all.

🧪 #2: 7-Day Trial (Mediocre Results) – Depending on what service you use to house your members-only dashboard, a 7-day trial might be very easy or very complex. We tried it with no credit card required AND a required credit card. Without a credit card we had more trial signups, but overall (credit card required or not), the 7-day trial never converted well/consistently for us to paying members.

🧪 #3: First Month Free (Not Enough Results) – Similar to the 7-Day Trial, we tried a first month free which gave people more time to kick the ole tires. Unfortunately, due to the length of time it took to see if this experiment would work, we abandoned it because it wasn’t converting quickly enough. This experiment is one we could bring back now that we aren’t in need of getting paying customers as quickly as we were in the beginning.

🤝 We share these three experiments with you not to say they will or won’t work but just to give you additional ideas of things you can try!

🗣 Marketing: How are you going to attract people to your community?

If you have an existing audience, your first 100 customers are going to be easier to get than the second 100.

For the majority of paid communities, new memberships, in the beginning, are going to happen because you are the leader of the group and people want to be around you. Early on, this is great and it’s going to be how you get your first ~100 members (or more).

Eventually, you’re going to exhaust your existing audience and you’re going to have to figure out what will bring in new members as time goes on.

What works well for us to organically grow our audience:

The key for YOU is to find the places your ideal customer hangs out and show up for them there.

Want 13 marketing ideas you can try to help grow your paid community? Learn about our Marketing Bridge concept and use our completely free 13 marketing blueprints.

What works to convert our audience to paying customers:

*We offer our affiliates a 40% commission as we want it to be a badass affiliate program for them. This is a no-brainer for us since our members who have seen results from our membership are the best advocates to market it for us. Plus, it’s almost zero effort for us to get these referral customers, so we’re willing to only make 60% of the revenue. For us, that’s $84,000 in lifetime value (LTV) from our affiliates in just one year.

⏳ Where do you want to spend your time and effort?

We don’t spend ANY money on paid advertising to grow our membership community. We don’t spend much time on social media. We don’t do a lot of interviews. We rely heavily on organic growth tactics and being okay with a slow and steady approach to growing our community.

We love sharing our experiences and the realness of what it takes to run online businesses. Case studies, project breakdowns, and being honest about the roller coast ride of entrepreneurship are the things that attract people to us.

Don’t be afraid to go against the “industry norms” and lean into what tactics you feel most drawn to when it comes to marketing and selling your community.


How do you plan to sell your paid community? Are you going to attempt an evergreen (sales funnel) strategy or will you use an open/closed enrollment strategy like us? How will you show up to other places online to attract new members?


Wrap-Up: We LOVE Our Community (and Reasons Communities Fail)

Alrighty, you’ve made it this far 👏👏👏. Let’s wrap this puppy up and send you on your paid community creation ways…

❤️ Our community gives us a sense of fulfillment!

We’ve been slowly removing ourselves from social media since 2016. I, Jason 👨🏻‍🦲, am off FB and Twitter completely and our paid community is where I get all the online social interaction I need. It’s just the right amount of active people each day who share our same values in life and business that I love spending time with.

Because I genuinely enjoy our members and want to participate in their journeys through life, it makes it easy for me to pop open email/Slack each day and connect with them.

If you’ve wanted a deeper connection with your customers but don’t want to devote a ton of hours to social media apps, creating a paid community is a wonderful option.

Running a community IS work, as you’ve learned from the rest of this article, but I’m so glad we made the switch to a paid membership business model in 2018. Our revenue is more predictable, we get more direct feedback and interaction with our audience, and we know we’re making an actual impact with people (instead of them just collecting another online course they never look at).

Community around a bigger problem, not a course, makes it a more rich and diverse place

We’ve heard from so many of our community members over the years that they love the diversity of our community (diversity in content AND the people in it).

The reason this diversity exists is that our paid community isn’t focused on a super-small-specific-niche problem. While that could be a great way to initially get traction for a community, if you’re only solving one small problem the community content and member base will get stale quickly.

Going back to our example company Rocket Lab 🚀, instead of creating a community just around SEO or using Asana, focusing on the problem of optimizing your business creates a much broader set of opportunities for content and people to join. The problem is specific yet flexible, which is the sweet spot.

Don’t forget about being clear on your values and beliefs as the person who runs the community

We didn’t make our values and beliefs CRYSTAL CLEAR on our sales page when we first started selling our community. This led to people joining who had the business problem we were solving BUT who didn’t share our deeper values and beliefs.

Now, this can get very tricky very quickly and we’re certainly not saying you have to create a groupthink mentality; but it is important to draw your lines in the sand and dissuade people who are in harmful opposition to your core values. Things like:

Pro-tip: We put a section directly under our buy buttons that calls-out our core values one more time to make sure new customers are on the same page with us before joining.

Wandering Aimfully Sales Page Social Justice Message

Yes, we run an online business community, but there are real people in the community and we want those people to feel accepted for who they are and surrounded by people who won’t judge them.

Since putting these core values on our paid community sales page we’ve attracted more of our ideal audience who always wants to support, uplift, and cheer on one another.

😬 How can you avoid a failed paid community?

Precursor to this section: Failing is NOT the worst thing in the world. For some people, having a failed community is a good thing because they learned what they don’t want to be doing with their biz!

I’ve watched many friends and peers in the online biz space start communities only to shut them down after a few months. These are the recurring themes I’ve seen and the reasons why I believe these communities weren’t able to thrive:

  1. They built a community of people they don’t actually want to hang out with and help.
  2. They built a community around ONE product which gets really boring over time.
  3. They don’t share their core values early on and end up attracting people who are opposed to their beliefs.
  4. They don’t understand that YOU have to show up for your community a lot for your community to succeed.
  5. They don’t try enough marketing, promotion, and sales ideas to see what actually works (free trials, test drives of the products, in-depth previews, helpful enough sales pages and sales emails). It’s taken us about two years of trial and error to feel confident in our sales/marketing strategy.
  6. They try to pass their community management off to someone they can pay hourly who doesn’t have their experience.
  7. They don’t show up for their community consistently and authentically.

🚨 One final thing I’ll mention about avoiding a failed community: PLAN FOR FAILED PAYMENTS. 😂

We use Restrict Content Pro (aff link) to manage our community memberships which have built-in failed payment email reminders. But, as good as these are, I personally recover 50% of our failed payments each month by sending direct emails/DMs to members.

Early on, I thought our automated failed payment emails would do the trick. They did recover some payments, but not enough.

Get mentally ready to see failed payments each month and to have to help people get them sorted out.

🙌 Final final thought: A paid community has given me the MOST fulfillment I’ve ever had in my near 15 years of running online businesses. Showing up regularly for our members, especially our monthly live coaching sessions, feels so great to me as a business owner and human being. Plus, the recurring (fairly predictable) MRR is pretty damn awesome!

Setting Up, Running, and Growing a Paid Community

(Big Fat Takeaway)

Running a paid community is not a set-it-and-forget-it business. While it does take ongoing effort, it’s also a very rewarding business model if you enjoy managing a group of people around a specific topic.


This article written by

Jason Zook

(he/him) Co-head-hancho of this WAIM thing. I used to wear t-shirts for a living, now I just wear them because I'm not a nudist. You can usually find me baking things, watching JCVD movies, and dreaming of living on an island.

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