Chasing overdue invoices is awkward – I built a small tool to automate reminders
Hi everyone,
I just recently joined Indie Hackers and I’m looking for advice and feedback please.
Over the past few months I've been working on a small tool I’ve called PayNudger and this is my first attempt at building something myself.
The idea came from a problem I've seen for years.
When I worked as a tower crane erector I had to invoice companies for my work and sometimes had to chase payment, which was always awkward. Sometimes I was just too busy and simply forgot to chase it.
More recently my brother-in-law, an electrician, and another family member who imports produce both deal with late payments regularly.
They both said the worst part isn't sending the invoice, it's chasing it afterwards.
That awkward “just checking in on this invoice” email.
Some clients are habitual late payers, but many simply forget and reminders still need to be sent. My electrician brother-in-law said the worst part of chasing invoices for him is that it makes him feel like he's being desperate, which he hates. That was actually one of the reasons I built it.
I did look for simple reminder tools first, but most options were tied into full accounting software, which many freelancers and small businesses don’t want because they already work with an accountant.
So I built a very simple system that automatically sends polite reminder emails once an invoice goes overdue and focuses only on that.
The goals were to keep it as simple as possible:
• works with any spreadsheet/system
• no accounting software needed
• reminders come from your own email address
• easy setup
Another goal was to remove the awkwardness of chasing money you're owed. It also helps with the common situation where someone invoices a larger company, forgets to follow up, and then hears “you’ll have to wait for next month’s pay run.”
My electrician brother-in-law started using it and said it actually saves him time because he just adds the invoice to PayNudger when he sends it, so it fits easily into his normal workflow.
It also creates a record of reminders if clients become difficult.
I'm bootstrapping this with zero budget so I'm trying to figure out the marketing side as I go.
I would really appreciate feedback from other founders:
• Does the idea make sense?
• Is the problem common enough?
• Any advice on reaching freelancers or small businesses?
Thanks,
Neil
Congrats on shipping PayNudger. One thing I'd flag from working in the same corner: sending and writing are two different jobs, and people buy them at different moments.
Automation wins when someone has enough invoices that tracking them is real overhead. But a lot of solo freelancers only have two or three late clients at a time — for them the blocker isn't a scheduler, it's staring at a blank reply box trying not to sound either desperate or rude. I went at that half: a $19 one-time page that writes the day 0 / 7 / 14 emails, and you paste them into Gmail yourself (https://followdue.com). No sending, no Stripe or QuickBooks integration — deliberately.
Might be a useful onboarding question for you too: "how many invoices are late right now?" If the answer is one, they want words; if it's eight, they want your product.
Full disclosure: I'm Avery Lin (avrlin). I've been packaging a small Get-Paid Chaser Kit (freelancer invoice follow-ups: polite → firm → final cadence + a sheet schema that stops when paid) with AI assistance, so take this as adjacent interest, not neutral advice.
What you described matches the failure mode I keep hearing: sending the invoice is fine; the awkward part is the chase, so people delay and then write one emotional email three weeks later. A written ladder helps — due+3 stays human and reattaches the PDF; due+7 names amount/invoice # without apology theater; due+14 is final/stop-work language only if it was in the contract. Automating from your own address (like PayNudger) is smart; the other half is deciding the tone steps before you're mad.
Curious — for your early users, did the first polite nudge clear most late invoices, or did most money move only after the firmer second/third reminder?
One thing I would add: the larger company / next pay run detail is probably its own status, not just another late invoice.
For freelancers and small operators, I would split the follow-up path before automating it:
The timing and wording are different in each bucket. A generic "just checking in" reminder is fine at first, but after that the useful question is usually: which process is this invoice stuck in, who owns it, and what date should I check back?
Automation seems strongest when it follows that status map instead of sending the same nudge forever.
I ran into the exact same "sending the invoice is easy, writing the chase email sucks" problem with client work. I started with spreadsheets, looked at Chaser, and now I'm building ChaseFlow around that same narrow followup layer, ngl the emotional job here feels more real than the bookkeeping one. I think the pain is common enough if you stay focused on reminder 2 instead of full accounting.
This makes sense to me because the pain is not creating the invoice, it's doing the follow-up without feeling like you're damaging the relationship.
A few practical thoughts from the freelancer side:
The positioning I would test is not "invoice automation" but "get paid on time without awkward chase emails". That feels closer to the emotional job.
Sorry for the delayed reply — only just saw this.
Really appreciate the feedback.
That emotional side of it is definitely the part I keep hearing from freelancers and tradespeople — it’s often less about the invoice itself and more about avoiding that awkward follow-up conversation.
The point about reminders before the due date is interesting too. I may test adding optional pre-due reminders later on.
Still very early stages at the moment but trying to keep it lightweight and genuinely useful rather than turning it into full accounting software.