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Hey Reader, Quick question: aren’t launches great? The adrenaline, the dopamine, the rush when someone trusts you enough to buy a brand-new product or offer? Personally, I like them. I’ve spoken before about how often you should launch something new. BUT you can’t run on launches only. If your business only feels “stable” during a launch window, you have built a machine that runs on adrenaline and attention. It works. It also burns you out, because every revenue spike demands another spike, and spikes have a nasty habit of turning into your default operating system. So let’s find the middle ground, shall we? Today, we’re talking about retention, so you don’t have to launch something new just for the sake of launching. Keeping customers tends to cost less than winning new ones, and even small improvements in retention can swing profitability hard in the right direction. Harvard Business Review puts acquisition cost at anywhere from 5 to 25 times the cost of retention, depending on industry and study. A 5% retention lift can lead to profit increases in the 25%–95% range (again, context matters, and the range is wide for a reason). So yes, retention is a “growth channel.” It’s the one that keeps paying you after you stop shouting. We’ll dig into it in a second, after a quick message from today’s partner, whose very generous free offer will help you with both retention and attracting inbound leads. 📣 Brought to you by 📣Jana O.’s Free ‘Capsule Blog’ TrainingWhat if you could sign clients on repeat… with just a small capsule library of blog posts? This issue is all about tactics that feed off each other. Blogging is one of those. Done badly, it’s just another “ultimate guide” feeding Google’s AI. Done smart, it becomes a growth engine you own. There’s a smarter way to use long-form content in 2026 — and it’s waaayyyy better than churning out endless posts or burning out on social media. In this free training, content strategist Jana Osofsky teaches you her proprietary strategy — 12–20 high-converting evergreen blog posts written to give your audience exactly what they need, to feel ready and excited to work with you. Smart blogging is what built my first business from scratch, so I'm stoked to bring you this resource because I KNOW it works. I'm impressed with what Jana was able to put together! You’ll learn:
If you’re a coach, creative, or service provider — and you’ve been wanting to write a blog that gives you real ROI — this is the best method to do it! 👇
Want your name up here? Reserve your slot! (Sold out until April) Why solopreneurs keep launchingA launch has a clean beginning, a clean end, and a scoreboard. That structure is comforting when you are running everything yourself, because it compresses uncertainty into a single month and makes the business feel controllable. Retention refuses to be compressed. It lives in the awkward middle where customers either succeed, stall, or quietly drift away, and you have to build systems that keep working when you are tired, distracted, traveling, or simply over your own content. Yeah, retention can be uncomfortable. But it pays. The repeat-revenue loopIdeally, every core offer should have a post-purchase path that leads to one of these outcomes:
In business, what “ideally should happen” rarely does. Some of your offers will be stand-alones, one-and-dones. That’s OK, as long as it’s not ALL your offers. Let’s look at each of the four 1. Renewal: same type of value, ongoingRenewal works when the buyer’s problem keeps recurring, or when the outcome requires ongoing upkeep (strategy, accountability, iteration, staying current, maintenance). Think: memberships, retainers, advisory, paid communities, ongoing tool access, recurring workshops. Step 1: Define the renewal reason in one sentenceIf you cannot explain why someone should keep paying after month one, renewal rates will drop. Use one of these renewal anchors:
Step 2: Bake in renewal from day 1A renewal ask at the end is too late. You want micro-commitments that make continuing feel normal. Do this:
Note: I used “weeks” as a placeholder here. Depending on how your offer is structured, you can think in terms of days, months, quarters, and so on. Step 3: Make renewal a decision with zero frictionMost churn happens because renewal feels like a new decision with uncertainty. Fix it with:
2. Expansion: bigger/different outcome, deeper supportExpansion works when the buyer hits their first milestone and immediately sees a bigger mountain. It sells best off momentum, because momentum makes buyers ambitious. Step 1: Decide what “bigger” meansExpansion is one of three things:
Scope is often the most ignored type of expansion. Most gurus and their dogs preach extreme niching down. But when you’re hyper-niched (“I help moms over 40 who do Bikram yoga in downtown Tampa with their Instagram strategy”), expansion through scope becomes impossible. So you’re stuck on the get-new-clients-monthly treadmill. Once your client has solved their challenge, they don’t need you anymore. This is why you see different offers for different scopes in my stack. The client who struggles with content creation may buy The Profitable Content Engine. If I only helped them with content, that would be the end of our relationship. But I know that the same client could also need help with strategy, email marketing, audience growth, and so on. It’s easier for them to buy from the same provider they already know and trust. And it’s easier for me to work with the same client again than to acquire a new one. This is why most of my clients have bought more than one product from me — because no business needs help with only one thing. Intermezzo: let me tell you about StacyStacy Eleczko recently wrote this in her newsletter (which, BTW, you should be subscribed to): In case the screenshot is hard to read, she talks about how it took her a long time to buy her first product from me (Inbox to Income). It was a mix of right offer, right time, right trigger, right budget. Since then, Stacy has become a dear friend and a repeat client. All because:
Back to our sheep: Step 2: Choose the expansion triggerCommon triggers:
I told you Stacy’s story to help you understand how important and underrated triggers are. They are not something you can manufacture (at least, not ethically). The buyer needs to be aware of the trigger in their own time. Step 3: Build an “upgrade bridge” that feels like adviceYour expansion message should sound like an advisor speaking to a client, because that’s what it is. This is a loose structure you can use:
That keeps agency with the buyer while guiding the decision. See how it’s not pushy? This is why I said you should act as an advisor, not a salesman. 3. Referral: new buyer introduced by an existing buyerReferrals happen when people feel smart for buying from you and safe recommending you. That safety piece matters more than your referral program. Step 1: Earn referral rightsReferral asks work after a specific moment:
Ask too early and it feels extractive. Ask in the glow and it feels natural. Step 2: Decide on your referral mechanismThere are three clean options:
For services, direct intros are your best bet. For products, shareable assets + affiliate win. Step 3: Remove the social frictionPeople do not refer because they forget and because it’s awkward and cognitively expensive. You fix that by giving them:
4. Reactivation: past buyer returns when timing shiftsReactivation is where you stop treating “past customers” like a graveyard and start treating them like a warm audience with context. People re-buy when:
Yes, we’re talking about triggers again. This time, it’s easier for you to use them because you already know something about your client. I’m convinced that we all leave a lot of money on the table because we ignore past buyers. Step 1: Segment past buyers by success rateNot everyone will be ecstatic about your work together/the product they bought from you. That’s normal. So:
Step 2: Start a human conversationSure, you can automate this process and blast them with an email sequence. But, since you already know them or have some degree of connection to them, it would be a shame to go this route, especially if we’re not talking about hundreds of people. Instead:
The strategic move most people skipPick a primary path and a secondary path for each core offer. Example:
If you only remember one thing from this issue, make it this one: before you chase new clients, consider how you can help your past buyers again. It's easier and more profitable for both you and them. You will still need to do launches, of course. But your business won't depend on them alone. The Council BulletinICYMI, I recently launched The Council, a Strategic AF community, where we meet regularly to get shit done. I built it as a place for solopreneurs and founders who are tired of chasing algorithms and trends and want steady, compounding growth guided by real strategy. We just had our kick-off call and it was amazing! I have the best clients in the world and you can’t convince me otherwise! In the upcoming days, we’ll decide together on our first sprint and a bunch of other things. If you want to join this crew of amazing people and get ongoing strategy advice, hit reply. I’d love to tell you more about The Council and whether it’s a good fit for you or not. 🎙️ My interviews, podcasts, and moreMy friend Brian Ondrako had me back on the Just Get Started podcast to talk about The State of Solopreneurship report. I LOVED geeking out with him over the data and discussing what moves the needle for solopreneurs. Tune in on:
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