Invoice #1 is easy, reminder #2 is where the real mess starts

I left a few comments on Indie Hackers tonight and the same pattern kept showing up in very different products.

Sending invoice #1 is usually not the hard part. The messy part starts after a client asks for proof of work, says they need one more approval, or gives a promised date that quietly slips. I kept hitting that with client work, generic reminders went out fine, but reminder 2 still needed context from the whole thread, tbh thats the part that kept eating my time.

That is why I'm building ChaseFlow. Not another invoicing suite, just the followup layer after the invoice already exists and somebody needs the next nudge drafted with the right context.

If that sounds familiar, take a look: https://chaseflow-ten.vercel.app?utm_source=ih&utm_medium=post&utm_campaign=ih-roundup-2026-06-04

Curious what breaks more often for other founders: ownership, timing, or missing proof once an invoice turns overdue?