i wait a week i send the "hey just checking in email"
i feel like an idiot asking for money i’ve already earned
two weeks later i’m refreshing stripe like a fool
i am sick and tired of having to beg for my money
so i thought of creating a small ai that links to stripe/paypal figures out who is likely to be late on a payment and emails them automatically
it starts off polite gets firmer with time stops me from having to chase payments and even shows how much money $$ it recovered so i can stop guessing who’s ghosting.
not selling anything. not built yet. just trying to see if this pain’s real enough that people (like you) would drop around $49/mo for it. be real would you actually pay for this, or nah?
i just need to know if this is a real pain or if i’m over it.
Do not see clients who do not pay as clients, but as liabilities. The real solution isn't chasing them with smarter reminders, it is changing how you work.
Take partial or full payment upfront, use incremental milestones, and only extend credit to proven partners with a solid track record.
Chasing money after delivery just wastes time and energy. Protect your work, and time, and sanity, not your clients' excuses.
If you demand 100% up front, then they assume all thd risk.
If you do deposits and partial payments and so on then you share the risk.
Naturally you want to take no risk. Your customer wants to take no risk. It sounds like the original poster here is taking all the risk.
So to the OP I say, treat the money lost as an education. I spent 7 months chasing a tiny amount of money early in my career. It taught me the value of risk.
Lots of companies don't pay invoices on receipt. 90 days is really common. So all is not lost. But the important thing is to understand where you went wrong. Work out the value of the risk, and include it in your price.
I usually specify payment terms when quoting. Changing the payment terms changes the quote.
If a payment is late, call them directly that day and be firm. Not mean or harsh, just firm. "Hi, your payment did not come through, please take care of it so I can start working for you again." And then stop working with them until it does.
To answer your question, no. I would never pay for an automated service to email payment reminders. Because emails are ignorable.
Doing lots of slowly escalating "check-ins" and "reminders" means you are owning the problem, not the other party, and you're teaching them that every time they do nothing, they can expect another "reminder" or escalation that is not much firmer than where they are today. They become like the frog that gets boiled in slowly increasing water temperature.
Instead, I've found it much more effective to have only a small number of very clear interactions. Step 1) ask nicely - say what you need, when you need it - "payment is due in 14 days". Send approximately _one_ "first and final friendly reminder". That's it - if it doesn't work, and the 14 days has come and gone, then switch immediately into thermonuclear asshole mode - call them, show up at their office, hand it over to a lawyer/debt collector, etc, etc. It works best to a clear, contrasting, binary distinction between "asking nicely" vs "not nicely", good cop / bad cop, so that the transition is very obvious and gets a reaction.
The question "why would they trust me to deliver?" is a good one. And there are two answers:
1. How you sell will determine their trust level. In my sales deck, I have testimonials, case studies and the outline of our full process. By the end of the presentation, when I tell them the price, they expected $10,000, but it's only $4,000. I ask them to pay the 4k now. Or, pay 2 payments of $2,500.
2. If the prospect asks us to do ALL the work first, then invoice, I say the following: "if we do all the work first, it means that you have no skin in the game. In the past, that hurt my business because people would disappear after my team spent 300 hours working. For that reason, it's not our policy to do all the work first. We have 2 options."
Then, i end off by saying: "if that's a deal breaker, I understand and I will happy send you the plan for what you should do next if you want to go at it without our help"
It's the best way I've found to reduce the risk of clients stealing from me through non-payment. If they've already paid a significant portion, they're more likely to pay the rest. And even if they don't, at least I got something.
And don't be shy about using the small claims courts if the dollar amount is low enough to allow it. You don't even have to hire an attorney to do that (although you should have an attorney as a matter of good business practice anyway).
95% of the time it worked well and the milestones gave an opportunity to review progress with the client, perhaps even a change of direction. On several occasions it lead to extensions (more features) or new projects in the future.
As a self employed contractor (cloud infrastructure), who got badly burned in the past, the key was to have deliverables which were self contained but still required the next chunk of work to be of any use in the bigger picture.
The financial loss for me was only the most recent deliverable should the client decide to ghost me. I did happen unfortunately.
From my perspective, I liked working on multiple sequential deliverables rather than one final one. I appreciate that infrastructure might be more flexible than other areas and often contractors only have one final deliverable.
This “person” can be as angry/obnoxious as needed to get paid. And don’t be afraid to pass debts onto collection agencies - or at least threaten this…
You can preserve your nice relationships with customers - after all, what can you do, finance are a separate department, it’s out of your hands.
You just pay me $500 and tell me country and region the company is, and google debt collection agencies for you.
1. Get half up front so they are taking the engagement seriously. Call it a retainer fee if you need to. Proves you’re in their accounting system and that the actual buyer is motivated enough to get you on-boarded and paid so that they can get going on the project. There is nothing wrong with half up front. You’ve got expenses while the project is ongoing. It’s a good way to improve you’re overall cash flow.
2. Accounting people and the people you’re actually working with are almost never the same humans. Make sure you know the exact submission process to get the invoice into your clients accounting system. The larger the company you’re contracting with, the more complex and exacting their processes are likely to be. Very large companies tend to use systems like Coupa, and there’s a learning curve to interacting with them.
3. Make sure you have a PO, and then reference that PO on the invoice. Most accounting folks will ignore requests for payment that feel “blind”. It’s part of their anti-fraud and due diligence. Lots of automated, AI-driven fraud out there. We see fake invoices all the time. Don’t do business on a handshake. Document that buying process, including a signature on a scope of work, quote, or similar document that can serve as a contract.
4. As a small company or indie contractor, you can put terms of service as Net 15, payable upon receipt, or whatever you want. Yes, you need to put something on there…but generally speaking, it doesn’t matter what terms you set, especially to larger companies. They’ll pay you when they pay you according to their own byzantine policies, and their payment terms will override yours. We’ve noticed that the biggest companies tend to pay 90 days + day of the month the invoice was submitted, but have never experienced anything longer than that unless the buyer is going through their own hardships or other shenanigans are afoot.
5. We generally engage with accounting contacts to track down late payments, but will go back to the actual buyer that contracted us and ask for help if a payment gets stuck or the accounting folks are ghosting us. In our experience, the actual buyer is usually embarrassed that an invoice is unpaid and can shake the money loose.
6. Finally…getting paid is a PITA. 100%. But if you can put up with the nonsense of having to track it down, you’re almost certain to get paid…eventually. In over a decade of small business work, we’ve never not gotten paid for an invoice, because we were persistent. But yeah, late payments suck especially if you’re going through tight cash flow.
Hang in there and good luck. I feel your frustration.
Either way, I have never known clients to pay in advance and now I’m high enough up the food chain to know that every company has trouble from time to time getting clients to pay. But that’s never been a “me problem”. The company I work for has sales, accounting and legal to worry about it. I get paid on time regardless. The trade off in getting paid less per hour is well worth it.
I still wonder if most people doing “independent consulting” wouldn’t be better off taking your bog standard enterprise dev job working 40 hours a week or working full time for consulting company.