> 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.

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

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

> 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.

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.

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.

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.