What if we built a small native Trello power-up — simple, clean, and entirely dependent on the marketplace? Could it turn into a small business? Could it be a model for side projects?

It took off fast. 30,000+ installs, thousands of daily users, and today—over 500 paying customers.

Sounds good, right? Not really.

On the bright side — Trello is a fair ecosystem. Even small developers get discovered. No downranking, no hidden boost for “big players.” Clean UI guidelines, seamless integration, no middlemen, no 30% commission. Just connect Stripe and go. A perfect playground for a polished mini-product.

But then reality set in.

We priced it simply: $10 per workspace. Flat. Unlimited people, unlimited projects.

Sounds fair? Turns out even $10/month was a huge barrier.

When it was free, growth was fast and constant. Teams used us daily for months, sometimes a year, leaving feedback and spreading love. But the moment billing kicked in, many vanished overnight. Even companies with 30+ users preferred something clunky and unsupported over paying the cost of 2–3 cappuccinos.

Here’s the thing: for us, it’s hard to stay motivated supporting free users—especially if you’re bootstrapped.

Paying customers energize you. Free users don’t.

Today the project have 500 paying customers, and we’re happy to support them. The power-up pays for itself. It was always an experiment. And the gap between expectations and reality is what made it valuable.

My biggest lesson? Charge early.

Once people get used to “free,” that becomes the baseline. Asking for money later feels like betrayal. It’s paradoxically easier to charge upfront (after a short trial) than after a year of free use.

So, can a trello power-up be a real business?

Yes — if by business you mean a side project that sustains itself, serves a few hundred happy customers, and brings in some cash. But not if you expect it to become a standalone SaaS company.

And that’s okay. Sometimes the biggest win isn’t revenue — it’s the lessons.

Have you faced the same wall with free users? How did you handle it? Share your experience—I’d love to compare notes.