For the other early-stage founders: When did you actually start charging money? We're scared of scaring away our first users.

We’ve been running free for 3 months now with decent traction but zero revenue.

Keep telling ourselves we need more users first but honestly just terrified of losing the momentum we have. What was your experience switching from free to paid?

Three months is way too long. You’re just training people to expect free stuff and making it harder to monetize later. Skip the sudden switch. Go freemium or offer a short free trial. Grandfather your current users so they don’t revolt but charge new signups immediately. Users who won’t pay weren’t going to be valuable customers anyway. Better to learn that now than waste another three months.

Started charging on day one. Free users rarely convert later.

You have proof people want your product. The traction shows that.

Now, the question is whether they will pay. Don’t wait too long to address this or it will be awkward later.

I suggest reaching out to your most active users and asking them directly what they would pay for premium features.