This is one question I haven't head people asking a lot. If you are running a side project, spending the time and resources to set up and integrate with a payment gateway can be a few weeks of effort.
When do you think is the best time to start charging your customers and invest in that infrastructure?
With https://leadhonestly.com/ we charged users from day one. We offer a 14-day free trial, but even still, we require a credit card for the trial.
It's a bold move and we undoubtedly loose a few folks this way, however, those that do sign-up are relatively committed and their feedback is sincere in how the product performs to the value they're expecting from it. For those with less interest in paying immediately, we have a drip campaign to warm them from passive to active interest in the product as to not lose them altogether.
In terms of setting up a payment gateway, Stripe, Braintree, and others have done wonders to simplify this process. I wouldn't call it turnkey but the resources they offer can get you relatively close.
I added the pricing page that included a 15 day trial period before integrating the gateway. So users would think they were in a trial. When enough people wanted to sign up, I worked on integrating the gateway.
Be sure to keep your pricing very simple at first, both to integrate it faster and to be able to change it later.
This approached helped me to get feedback on the pricing as well, and improved the feedback from the users, you will get different feedback when users think there is money required.
Literally just thinking about doing the same thing. How did that approach go, did you get the gateway integrated within the 15 days or did feedback change how you were planning to bill?
I definitely recommend doing it. Feedback changed from the day I did it. Not only because people expect to pay, I immediately got more serious businesses interested as a side effect. A lot of businesses are hesitant on signing up with a Saas that is in beta mode and can disappear the next month.
I ended up integrating the gateway after a few months. I focused on improving the onboarding first.
The feedback you get as a paid platform is very different to the feedback you get when used by none committed free users. If your business will rely on paid users in the future, then the sooner you can charge the better.
If you're worried that the product doesn't has sufficient features to be charging yet, then you're probably wrong (assuming people are using it).
I think there are two separate questions here:
The answer to 1. is easy IMO - the sooner the better. Preferably, before you finish building the product. How else can you be sure it's even worth building? Being too timid/reticent to ask for money is definitely one of the top five mistakes I see first time founders make.
As for 2. - with tools like Typeform, Paywhirl, Stripe, Chargebee etc (to name just a few) it should only take a few hours of work to be able to provide rudimentary charging features. Supplement with a bit of manual work for invoice generation/account activation. If you suddenly get lots of traction, you can always build your own infrastructure later to save time...
Good luck!
Thanks a lot, everyone! Some great suggestions in there - super helpful.