Once your membership or subscription starts generating steady revenue, a new question inevitably shows up: should you keep pouring resources into finding fresh leads, or should you focus on nurturing the members you already have?
Memberships aren’t strictly a numbers game. This also becomes a conversation about retention — the often-overlooked lever that can completely change your revenue trajectory. While I’ll frame this primarily through the lens of memberships and subscriptions, the principles apply broadly across business models. Whether you’re running a coaching program, a service-based business, or even a subscription box, the core tension remains the same: do you fuel the top of the funnel, or do you double down on keeping people engaged once they’re inside?
There’s no one-size-fits-all answer. But what I see far too often is a misconception — that the only way to grow revenue is to relentlessly chase new leads. Yes, more leads often equal more sales, but that’s not always the smartest way to grow a business long term.
In this post, I’m going to unpack this question through the story of one founder, Jordan, who recently crossed $350,000 in annual revenue with her subscription-based wellness platform. Her challenge — balancing the drive to scale quickly with the reality of members disappearing after a few months — is one I hear from business owners at every level. And the truth is, the biggest leverage point when scaling is often hiding in plain sight.
What’s inside this episode:
- The counterintuitive reason chasing top-of-funnel can stall profit — even when it spikes sales
- A simple diagnostic to decide if you have a lead gen issue or a delivery bottleneck disguised as churn
- My email tactics that I swear by to increase engagement and retention (this is a hill I will die on!)
- How offboarding works as a growth lever for higher ticket and/or term projects to multiplies referrals, alumni sales, and repeat buyers
- The cost of acquisition vs attention and why this should matter a LOT to you
The Core Question: Leads vs. Retention
This all started with a question from Jordan, who runs a subscription-based wellness platform. Her business just crossed the $350,000 annual revenue mark, largely fueled by growth through social content. On paper, things are working — but behind the scenes, she’s noticing a painful pattern.
I run a subscription-based wellness platform that just passed $350K in annual revenue, and most of that growth came from social content. The thing is it feels like people sign up and then disappear and are gone after a few months. Right now, I’m stuck between pushing harder on acquiring new members (since I know how to do that pretty well) versus really digging in to fix retention and customer experience, which feels slower and a lot less exciting. I want to scale fast and I know I can, but I’m worried I’ll just keep pouring people into a leaky bucket. So my question is: at this stage, should I prioritize fueling leads to keep increasing revenue, or slow down and work on retention even if it means short-term growth plateaus?
Her words capture a dilemma many founders face once their memberships gain traction. On one hand, Jordan knows how to acquire new members — she’s proven that with consistent marketing results. On the other hand, she sees that many people sign up and then vanish after a few months, leaving her worried she’s pouring people into a leaky bucket.
The heart of her question is this: should she keep pushing hard on lead generation to fuel fast growth, or slow down to address retention, even if that means risking a short-term plateau?
Recognizing Bottlenecks in Business Growth
The first thing I told Jordan is that what she’s experiencing is completely normal. Businesses hit bottlenecks at different stages depending on their model, but there are some predictable inflection points — usually around $100,000 a year, again at $300,000, then $1 million, and later around $3 million.
For information-based businesses, that $300,000 mark is a big one. At $350,000 a year, or roughly $30,000 a month, many founders are still running lean operations. That sounds great on the surface, but it’s also the point where things start to feel like they’re breaking. You’re suddenly serving a lot more people than before, and the cracks begin to show. Members don’t feel quite as seen, supported, or valued as they once did, and retention starts slipping.
Service providers hit this type of delivery bottleneck earlier, usually between $80,000 and $150,000 a year. For them, the strain shows up as client load becomes unmanageable without help. By the $300,000 mark, it’s often time to bring in operations support or restructure the way delivery happens.
So Jordan’s frustration — feeling like people join and then disappear — isn’t a sign she’s doing something wrong. It’s a natural stage of growth. The challenge is figuring out whether it’s a delivery issue (members no longer getting enough attention) or an engagement issue (members not being guided to form habits that keep them connected). Either way, the bottleneck is a signal: the business has grown, and the systems that worked at $10K or $15K a month won’t carry you through $30K a month and beyond.
Diagnosing Retention Problems
When retention starts slipping, the knee-jerk reaction is to assume it’s just the nature of memberships — people come, people go. But that mindset leaves a lot of money on the table. The truth is, most drop-off patterns have a clear root cause. The key is asking sharper questions and looking honestly at your delivery.
The first and most important question is this: have members always fallen off after a couple of months, or is this a new development?
- If it’s always been the case: then the problem is baked into your offer or onboarding. Members are joining without fully integrating into the community or building habits that keep them engaged, so naturally they don’t stick.
- If it’s new: then something has shifted in how you deliver. That might mean you’ve outgrown your original systems, or you’ve become stretched too thin to give people the attention they once received.
What Delivery Shifts Look Like in Practice
Retention rarely tanks “out of the blue.” More often, it’s the natural byproduct of growth. When your membership grows quickly, what used to feel personal and high-touch can suddenly feel impersonal. At $10K or $15K a month in revenue, you might have been able to remember people’s names, comment on their posts, or personally welcome them to calls. At $30K a month, with hundreds of members, that level of intimacy isn’t possible without support.
This can show up in several ways:
- Members no longer feel seen or acknowledged in the community.
- Calls feel crowded, and members don’t get a chance to interact directly.
- Questions go unanswered for longer than before.
- The sense of belonging that drew people in starts to fade.
When that happens, the fix often isn’t a massive overhaul — it’s support. Adding a team member whose role is to manage community touchpoints, or putting systems in place to replicate that early “high-touch” feel, can make all the difference.
The Service Provider Parallel
For service providers, the bottleneck shows up differently but the principle is the same. Around the $80K to $150K range, delivery starts to strain capacity. If you’ve noticed that clients who once re-signed for additional packages are no longer doing so, it’s worth asking: what part of the experience changed?
For example, one of the web designers I work with thrives on client conversations — she never wanted to hand those off. But her projects were bottlenecked because she was doing everything. The solution wasn’t to cut her out of client interactions; it was to bring on a junior designer to handle production. That freed her to stay in her zone of genius — maintaining high-touch client relationships — without compromising delivery.
External Factors vs. Internal Responsibility
There are external variables, too. If you serve lower-income families, single parents, or any group deeply impacted by economic shifts, you may see higher churn when the economy wobbles. That’s real, and it’s outside your control.
But in most cases, retention issues are internal. They’re a reflection of whether your systems, your team, and your leadership have scaled alongside your revenue. This doesn’t mean self-blame — it means radical responsibility. Taking the time to ask, Where might I have dropped the ball? What did members use to get that they no longer feel? How can I rebuild that sense of being seen, heard, and valued at scale?
That kind of honest diagnosis is what separates memberships that plateau from memberships that keep compounding.
Why Scaling Too Fast Can Backfire
When Jordan said she wanted to “scale fast,” my immediate reaction was caution. At $350,000 a year, she’s in a strong position — but she’s not yet ready for what I’d call true scale.
Growth vs. Scale: Two Different Games
It’s important to draw a line between growth and scale.
- Growth means adding more members and generating more revenue, but usually with a proportional increase in costs — whether that’s hiring team members, paying for upgraded tech, or taking more of your time.
- Scale means being able to add more members and more revenue without a proportional increase in costs. That’s when your systems are mature enough to absorb new volume without breaking.
At $350K a year, Jordan is still in the growth stage. She can absolutely increase membership count and revenue, but it will come with added expenses — and likely more of her time, too. That’s not a bad thing, but it means she’s not at the leverage point where true scale kicks in.
The reality is that you probably want better clarity before you look for speed. And the real issue IMO is that Jordan doesn’t yet know why members are leaving.
Without that clarity, pouring fuel on the fire will only make the leak bigger. If members are leaving because they’ve gotten the full transformation they came for, then the fix might be introducing an alumni tier, advanced curriculum, or higher-level calls to keep them engaged.
But if members are leaving because they don’t feel supported, because the community feels like a ghost town, or because delivery has become stretched too thin, then adding more people only compounds the problem. Suddenly you’re spending money on ads, driving new leads into a system that’s already struggling to keep people engaged — and retention tanks even faster.
The Better Place to Grow From
The “green light” moment for faster growth is when you can confidently say:
- I know why people join
- I know why they stay
- I know what they want at 3 months, 6 months, 12 months
- I know how to keep them engaged at each stage of the journey
That level of clarity isn’t about perfection — no one has every variable nailed down. But it gives you a strong foundation. It means you’re not just playing a volume game. You’re building a business where each new member is more likely to stick, spend more, and bring others with them.
You also want to be really clear about the downside of speed.
I’ll be blunt: when founders say they want to scale fast, most aren’t ready. Growth at all costs can feel exciting in the short term, but it often creates burnout, financial strain, and reputational risk when members start quietly slipping away. Slowing down long enough to shore up retention isn’t glamorous — but it’s the work that makes scaling sustainable.
The Case for Retention Over Acquisition
When faced with the choice between fueling the top of the funnel or focusing on retention, I almost always point business owners toward retention. Here’s why: it’s not only the more sustainable play, it’s also the one that delivers higher profit margins over time.
Every new member comes at a cost. Sometimes it’s a direct ad spend, sometimes it’s the hours you invest in creating content, sometimes it’s both.
Let’s say it costs you $100 in effort or ad spend to acquire one new member. If your membership is $75 a month and the average member stays three months, you’ve made $225 from that person. After deducting your $100 acquisition cost, you’ve profited $125. That’s a decent 2x return.
But here’s where things get interesting.
Why Retention Wins the Math
Harvard Business Review published research showing that retaining a customer costs 5 to 25 times less than acquiring a new one. Translating that to our example, keeping a member might cost as little as $4–$20. If you spend $12 on average to retain someone for an additional three months, you’ve turned that same member into a $450 customer — while only spending a fraction of what it would’ve cost to acquire a new one.
That extra $225 in revenue, minus just $12 in retention efforts, adds $213 of nearly pure profit. The ROI skyrockets. Instead of doubling your money, you’ve effectively quadrupled it — without needing to replace that member in the funnel.
Profit Margins and Long-Term Value = The Real Wins
This is why I tell people: memberships are a retention game. When you shift your focus to keeping members engaged longer, your profit margins expand naturally. You’re not endlessly hustling for the next lead, you’re compounding the value of the ones you already have.
And here’s the kicker — retention doesn’t just improve your margins. It also makes your business more attractive if you ever want to sell or seek outside investment. Consistent retention numbers signal predictability and stability, which buyers and investors care about far more than flashy top-line growth.
Because of that, retention is probably a smart first lever.
When business owners start thinking about scale, they often obsess over new lead generation strategies. But the very first lever you should pull is retention. It’s cheaper, it’s more effective, and it gives you a healthier foundation to grow from. Without it, scaling fast is just accelerating the churn.
Practical Retention Strategies
Retention doesn’t happen by accident. It’s the result of intentional systems, touchpoints, and experiences that keep members feeling connected and valued long after the excitement of joining wears off. Here are the biggest levers to pull if you want people to stay.
1. Strengthen Onboarding
The first 30–60 days set the tone for how long someone will remain a member. If they don’t feel connected, don’t know where to start, or don’t form the habit of engaging early, the odds of them sticking around plummet.
That’s why onboarding needs to be more than a single welcome email. You need an experience that orients people, builds momentum, and keeps reminding them why they joined.
In my own membership, The Visionaries Collective, we run a three-month onboarding sequence — with the bulk of touchpoints happening in the first two weeks. Members get:
- Day 1: A welcome email with everything they need to get started (links, logins, and community guidelines).
- Day 2: A reminder to download our Mighty Networks app, fill out their onboarding form (where I collect details like birthdays and anniversaries), and introduce themselves.
- Day 3–7: Emails that help them set themselves up for success — identifying what outcome they joined for and how to achieve it, plus specific instructions on engaging in the community.
- Day 10: A personal-feeling “check-in” email that looks like it came straight from my Gmail account. It’s short, sweet, and simply asks, Do you feel like you have everything you need? This one consistently gets the highest response rates.
- Day 14 onward: A mix of reminders, success stories, and an early feedback form. This isn’t just about data — I’ve actually gotten full-length testimonials out of this step.
The result? Members form the habit of logging in, engaging, and showing up. And they tell me, over and over again, that they appreciate the volume of emails because it makes the community feel alive and keeps their goals front and center.
If you’re afraid of “too many emails,” hear me clearly: silence is more dangerous. Frequent, thoughtful communication is one of the strongest retention tools you have.
2. Consider Term Commitments
Cancel-anytime memberships sound attractive because they reduce the barrier to entry. But at a certain revenue level — often $300K to $500K a year — churn becomes a constant drag. That’s when introducing a term commitment (six or twelve months) can stabilize revenue and improve retention.
The key here is timing and context:
- Do it when your community feels engaged and active. Locking people into a quiet or half-dead community will make them feel tricked.
- Frame it as an upgrade. Run one last launch with the promise of “cancel anytime,” and then announce that moving forward, all new members will commit to six or twelve months.
- Support it with strong testimonials. People are more willing to commit when they see evidence of results.
It’s not for everyone — and Jordan, for example, felt strongly that her members wouldn’t respond well to it. But for many founders at her stage, it’s worth serious consideration.
3. Build Re-Engagement Sequences
Not everyone disengages on day one. Some start strong, participate for a few weeks, and then quietly fade out. Others lose steam around the three-month mark. That’s where a re-engagement sequence becomes crucial.
The idea is to identify where people tend to fall off, and then meet them there with reminders, personal stories, or incentives to come back. For example:
- At 45 days, send a “we miss you” email with highlights from the community
- At 60 days, share a vulnerable story about a time you almost gave up and why you stayed the course
- At 90 days, remind them of what they said they wanted when they joined and show them the next step to get there
This is probably going to be wise so you can reignite the spark that made them join in the first place.
4. Celebrate and Personalize
People don’t leave communities where they feel genuinely seen. That’s why personalization is such a powerful retention tool.
In my onboarding form, I collect birthdays, anniversaries, and business anniversaries (aka bizaversaries 😉). Every month, we celebrate those milestones inside the community. It’s simple, but it makes people feel valued and connected in a way that goes beyond the transaction of paying a monthly fee.
You don’t have to do birthdays if that’s not your vibe. But find ways to add personal touches: spotlight members, send handwritten notes, or create rituals that make people feel part of something special.
5. Offboarding for Service Providers
If you’re running a coaching or service-based business, onboarding is important — but offboarding is just as critical.
Most service providers finish a project, send a final invoice, and move on. But an intentional offboarding process can turn one client into multiple streams of revenue. It’s your chance to:
- Ask for feedback (and testimonials).
- Introduce alumni offers or maintenance packages.
- Invite them into a referral program.
- Celebrate their results so they leave feeling amazing — and eager to tell others.
This is what I call the “Bedazzle” stage of visibility — when past clients come back for more or send new business your way. It’s one of the simplest ways to increase lifetime value, but so few people do it well.
Radical Responsibility as a Leader
When retention slips, it’s tempting to blame the market, the members, or even the model. And sure, external factors like the economy or shifting priorities in your audience play a role. But more often than not, the real answers start at the top — with you, the leader.
The hard truth is that communities take on the tone of their leader. If you’re fully engaged, showing up consistently, and modeling the kind of participation you want to see, members feel it. If you’re stretched thin, disengaged, or trying to grow too fast without shoring up systems, they feel that too.
Retention issues are rarely just “member problems.” They’re usually signs that the business has outgrown its original way of operating and the leadership hasn’t adapted yet. That’s not failure — that’s growth. But it does require radical responsibility.
So ask yourself the hard questions. Instead of asking “Why are people leaving?” start with:
- Where have I dropped the ball on delivery or engagement?
- Am I engaging as much as I want my members to?
- Have I built systems that make people feel seen, heard, and valued at scale?
- What steps have I already taken to fix retention, and where am I avoiding uncomfortable changes?
These aren’t easy questions. But they’re the ones that shift you out of blame and into action.
Leadership Sets the Ceiling
There’s a saying I don’t love — “the fish rots from the head” — but the sentiment applies. When things go sideways in a membership, the first place to look is leadership. If members aren’t engaging, chances are the leader isn’t engaging at the level required. If the community feels stale, it’s often because the founder hasn’t invested in systems, support, or innovation to keep it vibrant.
The good news? Just as leadership can be the source of disengagement, it can also be the spark for re-energizing a community. A single shift in how you show up, the systems you put in place, or the way you prioritize retention can ripple through the entire membership.
At the end of the day, your business is leadership game. (Louder for the people in the back!)
Your role isn’t only to bring people in the door; it’s to create an environment where they want to stay. That means leading by example, taking ownership of the experience, and continuously asking how you can make members feel more connected, more valued, and more supported.
To Wrap Up: Why Retention Is the Ultimate Leverage Point
Memberships and subscriptions live or die on retention. You can pour endless energy into top-of-funnel strategies — running ads, posting content, pushing for visibility — but if members leave after a few months, you’re constantly sprinting just to stay in place.
Retention flips that dynamic. When people stay longer, your profit margins expand, your growth compounds, and your business becomes more predictable. You no longer need to chase new leads at the same frantic pace, because each member’s lifetime value is higher. And if you ever want to sell your business or attract investors, strong retention makes you exponentially more attractive.
That’s why I tell founders like Jordan — and anyone running a membership — to treat retention as the first lever, not the last. It’s less expensive, more effective, and far more sustainable than acquisition alone.
Does that mean ignoring new leads? Of course not. You’ll always need fresh people coming in. But scaling with a leaky bucket is a recipe for burnout. Scaling with strong retention is a recipe for longevity.
So the next time you feel pulled toward “more leads, more leads, more leads,” pause and ask: have I really done everything I can to keep the people I already have? Because the biggest leverage point in scaling isn’t always at the top of the funnel. More often than not, it’s hiding in plain sight — in how well you care for the members who’ve already said yes.
