Does the following apply to you?
If you answered yes to all 3 questions but you're still not charging - take this as your sign to start. I talk to so many founders who afraid to ask for money from their initial users. While there are scenarios where that does make sense, here's the thing...
It's often dangerous to wait too long to ask for money.
Yes, dangerous. You see, ultimately, you need to make money from the product you're building. To do this, you need to make sure you're creating something people find valuable enough to pay for. The only way to know for sure that you've done this is to get people to give you money.
It's incredibly easy to wander down the wrong path with your product, catering to a bunch of users who have no intention of paying you. Eventually, you'll start to charge and discover that no one is willing to pay. Even worse, you may also discover that the people who are willing to pay have a whole different set of needs than the users you were originally building for. That all adds up to a lot of wasted time - which is a high price to pay for most founders.
But... our early users are doing us a favor!
Sure, that's true to some extent - but your product should also be doing them a favor. If you're not currently providing them enough value to pay, figure out what you need to build to get there... and then start charging.
I don't feel comfortable asking users for money!
This is something you'll likely need to get over pretty quickly as you build a business. However, there are spme other options for validating that you're building for the right people before actually asking them for real money.
First, you can simply ask people if they're willing to pay and how much they'd be willing to spend. Unfortunately, this is pretty low signal - it's very easy for someone to hypothetically commit to paying. Plenty of founders have gone down this route only to find out no one was _actually_ willing to put money down when it came time to pay up. Still, by doing this you'll start to get a sense for what kinds of users place a higher value on your product... hypothetically.
Another option is to get users to put it in writing, usually referred to as a Letter of Intent or LOI. This gives a stronger indicator of willingness to pay, but are still nonbinding. LOIs are generally used for larger ticket items, like enterprise software or complex hardware, so don't try to gather a ton of LOIs for your $20/month SaaS product.
I don't have time to integrate a payment solution!
Well, it's likely time to find the time... but if you really can't, then remember this: your users are likely early adopters. This likely have a higher tolerance for cobbled together systems. Ask them to Venmo you, have them mail you a check, set up an out of the box eCommerce store and then manually give them access. The important thing is that they're willing to go through the psychological process of giving you money in exchange for your solution.
I don't want to mess up pricing!
No one gets pricing right the first time. Arguably, some companies never get pricing right. The wonderful thing about being an early company is that you can experiment. Lots of people paying? Raise the price (but grandfather the previous users into the old one). No one paying? Lower the price (and consider lowering it for anyone who did pay as a gesure of good will).
I don't think any of this applies to my business!
That might be true - like with everything else, there's nuance and exceptions. However, if you got through this whole post and you find yourself thinking even a little bit that it's time to start charging... then it likely is!