What 30k Free Users Taught Me About Charging $10/Month

Two years ago we decided to test an idea.

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.

Did/do you offer annual plans too? In my business, we're put off paying small amounts per month for things because of the bookkeeping work (we have someone who manages our books but we still have to find and create a PDF of every receipt every single month which is boring) so for longer term things we tend to find options with annual plans. It also means we're "locked in" for longer which is good for the seller.

As a consumer, $10/mo is great. As a business, $10/mo is as much headache as $100/mo.

6 hours agoby petercooper

Our service incurs direct per-customer costs from deployment to retirement, and typically requires our time, so we have no free offerings at all. We don’t even do free demos.

We learned these lessons because of an early mistake we made. Undercharging. Do not undercharge early. We did that and it made it more challenging to build a sustainable revenue stream that would actually pay all the bills we wanted/needed to pay. When we started the company we resolved to only need one capital contribution from each cofounder. When we started by undercharging that really held us back for awhile.

On the flip side, we learned that building strong relationships with customers, not being afraid to put things in writing (our customers tend to dislike phone calls as much as we do anyway), and delivering on time, meant that when we asked customers to pay more at their next renewal, they were fine with that.

But it really sucked to have such a small budget. It also taught us a lot about the value of resourcefulness and not just jumping on every trend, SaaS service, and solution that was hot or shiny. That was valuable in its own right because it’s resulted in a service we can run on just about any Linux platform.

3 hours agoby TheNewsIsHere

I have had the same experience. Realistically speaking, the vast majority of people don’t want to pay for anything. And so if you can avoid giving the impression that your product’s value is not worth paying for, do so. In many situations, it’s preferable to have 1,000 paying users than 50,000 free ones.

6 hours agoby keiferski

> My biggest lesson? Charge early.

How do you know that you wouldn't end up with even fewer paying customers if you'd taken that path?

6 hours agoby YcYc10

Did you mean to post this on LinkedIn?

6 hours agoby have_faith

There are two lessons here:

1. When selling software to companies, don't price it like a consumer service.

For a company of any size, paying $10 and paying $100 for a tool require the same amount of work for someone to process and it is essentially the same cost to the company. The money itself is negligible, and a $10 price makes the company assume you either won't stay in business or won't be able to run a secure company. Charge a price that makes them take you seriously.

2. People really, really hate it when you "change the deal."

If you offer a free tier, offer it on a time-limited or user-limited basis up front such that your ideal customer would have to pay to keep using the product. Otherwise, you'll find yourself changing the deal and pulling the rug out from users. Changing the deal ruins your reputation. Charging more upfront can actually give you a reputation for quality.

3 hours agoby ageitgey

Why is this flagged?

51 minutes agoby thunderbong

In my company it is easier to request a purchase of a new hardware for 5000$ than a 10$ software plug-in or extra license. Easier for end-user at least.

4 hours agoby Yizahi

(I'm ignoring how blatantly AI-written the OP is and assuming good faith that the text accurately represents the actual situation.)

> 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.

1 in 60 seems like a pretty good conversion rate to me from other stories I've heard. And who knows if you actually would have reached 500 paying users if you'd charged from the beginning. After all, your free round produced targeted advertising to an audience of 30,000.

6 hours agoby zahlman

I think many people don't want to pay anything, but I think a part of that is that it's still just a big hassle to pay online, and that's doubly true if they have to get corporate approval or whatever.

It seems like a free trial period with clear pricing is the way to get paying customers, and any free plan needs to be monetized with ads or whatever.

3 hours agoby jacknews

Food for thought: Perhaps it wasnt't the money as much as Stripe itself being the barrier? Maybe you would have gotten better turnout with other payment options (especially for a platform like Trello, crypto like BTC/XMR might be more welcome than you'd expect).

> My biggest lesson? Charge early.

Can't argue with that. And even if you go free early, advertise it as "free trial during our early days" or similar. If you already plan on charging in the future, get people used to the idea of having to pay for it from day one even if you give it away for some potentially extended time. Proper free-tiers with expectations and terms can come later down the line when the pricing strategy is clearer.

People emotionally respond very differently to their free trial expiring ("it was nice while it lasted") vs having their previously free service being replaced with a paid one ("f this enshittified rugpull"). The difference is proactive communication and setting of expectations.

7 hours agoby 3np