Tired of Chasing Clients for Late Payments
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I absolutely despise sending follow up reminders it feels needy, awkward, and just a reframing of mental energy.
So, I am thinking...what if an AI tool could send those reminders for me?
Connect to Stripe or PayPal, it predicts who will likely pay late and automatically sends out a reminder email that gets firmer each time.
IM NOT selling anything. Just qualifying if this is a pain point. Would you actually be willing to pay $49/mo for it to manage this whole mess for you? Or is this just a nice idea? And it's not worth cash?
Only be brutally honest please :)
The author is tired of chasing clients for late payments and proposes an AI tool to automate reminders, seeking feedback on whether it's worth $49/mo; the discussion revolves around the tool's potential value and effectiveness.
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Oct 10, 2025 at 8:03 AM EDT
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I wouldn't let AI near it unless you don't care how you are perceived (parking fines?).
2) There was a time in a prior life when I did consulting, and of course I experienced the same issue. I re-wrote my contract to get paid in advance each and every week (seldom every month). If I had no payment in my bank, no work that week. Easy, simple, the client was always in control.
Must watch: https://www.youtube.com/watch?v=oEa6PdOG2ts
It's business, nothing wrong with sending a reminder when the payment deadline is reached. Make it a process to follow: create a template and boom, nothing to think about except filling in the blanks when the date is reached.
You don't need AI to check if a payment has been made by a specific date! And you don't need AI to keep tabs on who has previously paid late and might need an extra early nudge.
You have submitted the same Ask HN twice. Not sure what you are trying to achieve?