Should I bundle my software into a paid community to cut churn?

I went back and forth on this for months with my newsletter software. Here's how the thinking went, including where I landed. These were plans, not proven results.

Why bundle software with a community at all?

Churn. Lots of people start a newsletter and stop a month or two later. If I sell a newsletter tool on its own for $49 or $99 a month, I get those people, plus all their tickets.

The money isn't even the main issue. It's the annoyance, the effort and the tickets. People stay a month or two and it just becomes a pain.

The bundle fixes that. Instead of selling the tool alone, you only get it as a member of a community priced somewhere around $200 to $500 a month. Leave the community and you lose the software.

"Well, guess what? If you're used to the software, you're not going to leave the community."

A tool that might sell for $50 to $100 alone is effectively earning $250, because members won't give it up. Once they're using it, going back to doing it by hand would be a huge loss.

What's the downside?

It shrinks your market. Fewer people will join a $250 community than would try a $99 tool. Maybe you make the same money either way, but it's a real risk.

My market, local newsletter operators, is already much smaller than a general creator audience. A friend pointed me to a $97-a-year copywriting community as a model, but that audience is way bigger than mine. A small market has to be higher priced and much higher value.

What would the community need to include?

I don't want one where the owner just facilitates and isn't that helpful. What I sketched for about $500 a month:

• Weekly office hours to ask me anything
• A session where my VAs teach your VAs how we do what we do
• Walkthroughs of everything we're working on
• Meta ads run for you, since we even use the same ad for every location
• The software

The economics come from scale. It makes no sense for one operator to pay for some of what I can do, when one person can help 20 or 40 newsletters. I later leaned toward a mastermind with weekly teaching over a loose community.

Where did I land on pricing?

By December 2025 I flipped it. Price the software on its own page, and make the community a perk of the higher software tiers.

Software tier	Community access
Middle tier	50% off
Top tier	Free

With a community at $79 and the software at about $100, you're effectively getting the software for around $25. The community is great for cash flow. The software is the big exit.

Why does it matter where the revenue shows up?

Investors. If payments run through the community, an investor sees 27 or 46 users and asks why it's all running through a community. If people pay for the software and get the community free, the numbers are software numbers, even if the real reason they pay is to get on calls with me for Meta ads help.

What if a competitor's community is cheaper?

Don't fight on price. One competing community I looked at was about $50 a month, or $500 a year. Charging $100 a month to that same small-operator crowd for calls and shared material would be hard.

The power play is going up-market. He's going down market to entrepreneurs. We go to existing brands. More on that in targeting solopreneurs or real businesses.