The Easiest Customer to Win Is One You Already Lost. Count Them Before You Expand.

A CFO once drew a tree on a whiteboard, with three apples hanging at different heights, and asked which one would be easiest to pick. The person he was asking pointed to the lowest. The CFO smiled and drew a fourth apple, lying on the ground.

That story opens a recent piece from Digital Content Next, the trade group for digital publishers, and the apple on the ground is former customers. They already know your product. They've experienced its value, and at some point they decided to stop paying for it. For news publishers, that pool is enormous. INMA's analysis of 136 news brands, published in June 2025, found the median publisher had recorded 1.7 times as many digital subscription cancellations between January 2019 and March 2025 as it had active subscribers that March. That counts cancellations rather than unique people, since one person can cancel twice, but the scale is the point.

The piece is written for publishers, but the lesson I'd draw from it is for a founder whose growth has flattened and whose board wants to talk about a new market. Before anyone sizes that market, someone should count the apples on the ground.

Lapsed customers are evidence, not just a segment

The usual reason to care about former customers is that they're cheap to reacquire, and that's true as far as it goes. But for a company deciding where to grow next, they're more valuable as evidence than as revenue.

Think about what a lapsed customer is. They had the problem you solve, badly enough to pay for it. They chose you over the alternatives. They used the product long enough to form an opinion. And then they left, which means they know something about your product that your happiest customers don't, and that a new market, however carefully you research it, can't tell you yet.

Most expansion plans skip them anyway. A new audience is more exciting than an old one, and "why did they leave?" is an uncomfortable question to put in front of a board. I've written before about how growth usually comes from the core – from serving the customers you have better – before it comes from new markets. Former customers are the part of the core that's easiest to forget, because they've stopped showing up in your dashboards.

Their reasons for leaving are the most specific feedback you'll get

At Adaptavist, documentation was one of the top five reasons customers gave for canceling their licenses. Our docs were scattered across more than 25 apps, six sites, and three platforms, and people were churning over it. The sales team was hearing a version of it, too: documentation had come up as a concern in three deals in a row.

That cancellation reason was the clearest direction we had. Consolidating everything took the better part of three years, alongside my other work, and afterward documentation became one of the top five reasons customers chose to buy Adaptavist products, and to keep them. I wrote up how docs went from a reason to cancel to a reason to buy a few weeks ago. What matters here is where the signal came from. It came from the people who'd left, and from the reasons they gave on the way out.

The research says the reason decides it

Marketing researchers have been making the case for this for a long time. In a 2004 Journal of Marketing Research study, Jacquelyn Thomas, Robert Blattberg, and Edward Fox argued that winning back lapsed customers deserves a place in a company's strategy next to retention. Modeling both the reacquisition and how long reacquired customers stayed, they found the best approach in their case was a low price to bring someone back, followed by higher prices once they'd returned.

More recent work points at why some win-backs stick and others don't. Studying repeat churn at a large telecom, V. Kumar and colleagues found a group of returning customers they called "cured": people who were no longer susceptible to leaving for the same reason they'd left the first time. Whether a former customer comes back and stays depends a great deal on whether the thing that drove them away has actually been fixed.

For a founder weighing a new market, that makes the reason a customer left the variable that matters, both for winning them back and for deciding what to build next.

Sort them before you expand

Before a new-market bet, I'd want the lapsed customers sorted by why they left, because the reasons fall into roughly three groups and each one points somewhere different.

They left over something you can fix. Bad docs, a missing integration, an onboarding that never got them to value. This is the cheapest growth available to you, and it's not in a new market. Fix the core, then go back to them with proof that it's fixed. If Kumar is right about "cured" customers, these are the ones most likely to stay the second time.

Their needs moved. They outgrew you, changed industries, or started needing something adjacent that you don't do. This is the group most worth interviewing before an expansion bet, because they can tell you where demand actually went, from the inside. If a lot of them moved in the same direction, that's an expansion signal with evidence behind it. If they scattered, the new market on your board slide may be a guess.

They were never a good fit. They bought on price, or for a use case you were never built for. These are useful in a different way: they tell you who not to chase, which matters when a new market starts to look a lot like the customers who already churned.

None of this requires a big research project. It requires pulling the list, reading the cancellation reasons you already collected, and talking to a handful of people from each group, which is far cheaper than learning the same things after you've built for a new audience.

The conversations go better when you ask about what happened rather than what they think. Ask about the last stretch of time they used the product, what was going on in their business when they decided to cancel, and what they did instead afterward. That last answer is the one to listen hardest for, because it tells you which alternative won and what it gave them that you didn't. Opinions about your roadmap are easy to give and cheap to ignore, and a question your best customer and your worst prospect would answer the same way won't tell you anything you can act on.

The step before validating a new market

If you're trying to validate a new market before you build for it, this is the step that comes before that question. New markets are sometimes exactly the right bet, and the answer to "should we go there?" is a lot more trustworthy when you already know why your own customers left. And sometimes the most valuable finding is that the right answer is no, because the growth you were looking for has been lying on the ground the whole time.

The highest apples are the most visible from the boardroom. The one on the ground is the one you've already paid to grow.