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Smarter Solopreneurs · Aug 10, 2026

Retention strategies: stop losing customers

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Maya Say · Smarter Solopreneurs

This is the least talked about marketing strategy among solopreneurs.

Retention.

We’re always talking about getting more people through the door. More subscribers, more buyers.

But if you don’t fix retention, you’re pouring effort into a leaky bucket.

It seems like retention is a growing pain on Substack, too, now that new subscribers aren’t coming in fast enough to cover for it.

A Substacker shares her experience of losing paid subscribers.

Every solopreneurs comes to this realisation sooner or later. When the platform stops attracting new people by the millions (what’s happening with Substack right now); when the algorithm changes; when the marketing budget runs out; when life hits and you can’t put in the same amount of time into getting attention.

And you realise that if acquisition stops, the business stops. That’s not a smart way to run a solo business. Or any business.

That’s why we buy the new course, trust the new guru, jump on the new platform.

It’s not bad to try something new, but to try anything without a strategy is just a silly way to react (instead of adapt intentionally), and it’s mostly a waste of time.

"I've learned you don't need as many tactics as you think you do. Don't do the sexy thing, just do the thing that works.”—Joanna Wiebe

If your solo business isn’t making enough money, don’t look for new sexy things to try. The first two things to work on are:

  • Improving the underlying math of your business.

  • Improving retention.

There’s always a price you pay for getting a new buyer through the door. In marketing, that’s called Customer Acquisition Cost or CAC.

In most businesses, CAC is measured in advertising dollars spent. Solopreneurs think they don’t have to calculate CAC because they don’t spend any money on ads, but this doesn’t mean acquiring a new buyer is free: you pay for it with your time and creative energy.

Sometimes your CAC is even higher than it is for that guy who runs ads on Facebook. If you pay yourself $25 per hour (and you should pay yourself a lot more!) and you spend 10 hours per month on posting notes, writing free articles, sending sales pitches, this means you spend $250 per month on acquiring customers.

If you spent $250 last month on acquiring paid subscribers and you got 4 new paid subscribers (just using Substack as an example) worth $60 per year each (and that’s if they got the yearly option), you made $240.

So you just lost money.

Now, one way to fix it is to improve acquisition. If you can get 8 new paid subscribers by putting in the same 10 hours of work (or even 15), that would fix things. That’s what everybody’s trying to do & talking about.

But there are other smarter, easier ways to fix things.

For example, you can learn more about offer stacking and pricing. If you can upsell and cross-sell, and if you adjust pricing, you can fix your math without more acquisition.

Once the math is fixed, the next thing to look at is improving retention.

There are two specific, easy to implement strategies that could massively improve retention (based on extensive marketing research & testing).

Read the original on smartersolopreneurs.substack.com

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