What 30k Free Users Taught Me About Charging $10/Month | Hacker News Reader

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

25 pointsevermike30 comments

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.

Yes, we do have a yearly plan — and it was a real surprise to see how often people choose it. After so many refused to pay $10 monthly, I assumed the annual plan would barely get any traction. But it turns out that’s not the case at all. That’s a really good point you highlighted!

Especially at larger companies there’s very little difference between $10, $100, $1000, $10,000 from the perspective of the effort put in to pay for it.

You’re putting the same requests and forms, doing the same due diligence, getting the same approvals, etc. All contracts need to go through the same contract review, etc.

Few places I’ve worked have sensible rules to bypass that.

You still need to make sure you’re value for money, but aren’t as constrained as absolute price as much.

Yes, I see what you mean. In our main product, where billing is per seat and we work with somewhat small-med biz, the subscription form after the trial asks how many seats you want to pay for. It’s possible to choose more seats than the number of users at that moment, which means those seats can be filled later without extra charges/invoices.

From time to time, we see cases where a single user signs up but purchases 20–50 seats for a year upfront. That’s still always surprising me in a good sense.

The whole topic of seats could actually be a separate discussion on its own, 'cause there are many nuances, good/bad approached and funny situations we’ve run into along the way ))

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.

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.

And there’s another interesting argument I hear from time to time: people tell me they use Google for free, or for much less, and it gives them way more.

Maybe the big companies are partly to blame for shaping the kind of mindset users have today?

Absolutely. If I remember correctly, until Google came in and started giving everything away for free, there was literally nothing available for free. Even email was capped to 2 MB with everything beyond as chargeable.

Originally, Google have away their workspace suite for free, which now people have to pay for.

The free tier everywhere has now become the ad-riddled tier.

Pricing problem really interests me lately, like where do we draw line? In cloud you may get access to essentially unlimited consumer storage, plus a lot of different paid services all for like 15$/month. Or you may purchase only one service from that pack for more. You may subscribe to some news aggregator for 10$ or to a single private blog for 20$. You may subscribe to a AAA modern 3D game for 15$, or buy a fraction of a fraction of a single character kit in a less advanced and worse looking gacha for the same 15$. You may buy a Netflix sub with years of content for 15$, or a single new movie one time 48h "permission" for about the same.

My point is, humans are unable and unwilling to operate prices less than 1, so everything is priced close to that number, even something incomparable in complexity and features. How do we even solve this?

> 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?

Ha, of course, it could have turned out differently. As of today, most paying customers are those who registered after we removed "free" plan, not long-time users. My reflection is that no matter how much I tried to rationalize it, I was convinced that for people who had been happily using the product for years, paying $10/mo wouldn’t be a problem. And I honestly don’t know if it would have made any difference if the price were $5 or $4 — or if it’s just a kind of protest. Interestingly, we also have an annual plan for $100, and it’s chosen fairly often — again, mostly by new users coming straight from the trial.

Did you mean to post this on LinkedIn?

To be honest I did - https://www.linkedin.com/posts/mikekulakov_two-years-ago-we-...

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.

1) I generally agree with the first argument, but I think context matters a lot. There’s always a market price depending on what the product does and what competitors offer. If your pricing is far below or far above that range, it usually won’t work out well. Our add-on was mostly for 1-3 ppl team.

2) As for the second point that’s definitely a lesson I keep bumping into and somehow never fully learn. No matter how clearly you communicate and give advance notice, users still perceive it negatively. And yet, as a user myself, I regularly get emails from services I pay for about price increases or plan changes. Very few companies offer true grandfathering forever.

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.

In our case there are no big companies involved. And Stripe, which we use, makes the payment as simple as possible for the user. It feels more like plain unwillingness to pay anything at all.

Can't say anything RE advertising. Don't have experience. But I think you’d need an even bigger user base to make ads meaningful. And I’m not even sure Trello would allow it. I’ve never seen any other plugin do that. Do you have an example?

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.

100%. What’s also interesting is that this pattern holds true in many other aspects. I often review our support tickets to see what customers are writing. And often, the bigger the client, the more polite and reasonable they are. Of course, there are exceptions.

For example during down time. AWS might goes down and we’re rushing to fix things. The first ones to complain are usually the smallest customers. They tend to write everywhere, often in a rude tone, sometimes exaggerating “we couldn’t track time for half a day”, while it is only 10 mins. Bigger clients usually more polite, thank us for responding quickly, and sometimes even offer to buy us some coffee 'cause they say we’re under pressure )

Have you tried keeping the free users on for - say 6 months and then start charging them?

We started to monetize the add-on after a fairly long period, definitely more than 6 mo. Those early users didn’t convert well. That’s exactly where my confusion comes from. It probably would have been better to start billing almost right away. Maybe with a lower price at first and then raise it with adding more features, but the idea is to begin charging as early as possible.

(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.

Historically, apps have a 2-4% conversion rate from freeware/shareware to paid. That's pretty much on the mark.

I guess I just wanted too much ))

You mean 2% conversion from free to paid, or from trial to free? In our main project, we usually see around 4–5% conversion from trial to paid. But here it’s different, people have been using the product for a long time, everything works well for them, and the price doesn’t seem high at all.

Why is this flagged?

I honestly have no idea. I don’t know what I could have done wrong by simply deciding to share my experience.

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.

Stripe has payment via crypto methods. Pricing a recurring payment in crypto feels off putting to me as it’s likely the cost will change often due to crypto volatility.

By the way, we’ve only had a single chargeback so far — which was surprising in itself. And our churn rate is around 6.5%, which is actually pretty solid for a product like this and for this kind of audience.

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