Tired of chasing clients for late payments

#1

Post by jesusfchristn » Fri, Oct 10, 2025, 12:03 PM UTC

Each month there is at least one client who does not pay my invoice.

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 :)

Re: Tired of chasing clients for late payments

#2

Post by mytailorisrich » Fri, Oct 10, 2025, 12:08 PM UTC

> I absolutely despise sending follow up reminders it feels needy, awkward, and just a reframing of mental energy.

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.

Re: Tired of chasing clients for late payments

#3

Post by pestatije » Fri, Oct 10, 2025, 12:11 PM UTC

accounts do that...not exactly sure what the role name is

Re: Tired of chasing clients for late payments

#4

Post by SMAAART » Fri, Oct 10, 2025, 12:20 PM UTC

1) There are at least a couple YCcombinator startup that does collections: Domu and Respaid.

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

Re: Tired of chasing clients for late payments

#5

Post by beardyw » Fri, Oct 10, 2025, 12:21 PM UTC

pestatije wrote: post #3

accounts do that...not exactly sure what the role name is

Debt collection.

I wouldn't let AI near it unless you don't care how you are perceived (parking fines?).

Re: Tired of chasing clients for late payments

#6

Post by beardyw » Fri, Oct 10, 2025, 12:40 PM UTC

See https://news.ycombinator.com/item?id=45537958

You have submitted the same Ask HN twice. Not sure what you are trying to achieve?