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

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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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