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How ChatGPT helped a company to get back its $109,500 from a client who was not paying

It is very frustrating when you offer your services with complete dedication and carefulness to a client and then after receiving those services, he refuses to pay.

It is common nowadays, as humans are becoming more selfish and greedier than ever. We have an economy where it does not matter whether you are rich or poor, you always have the fear that your pockets will become empty one day.

To extract the money which someone owes you, you will most likely call him or confront him first. If he is not willing to way, then you would take legal action or look for some illegal ways, like threatening or hiring goons. But they are quite expensive and why would you spend money to get your own money back?

Something like that recently happened with a company and the CEO decided to take help from the AI chatbot, ChatGPT to write a formal threatening email to the client who is not willing to pay the company’s $109,500 which is around 90 lakh in Indian rupees.

Greg Isenberg, CEO and founder of a design firm, Last Checkout shared on Twitter on February 24, that last year, a client has reached out to his company for some designed work. When Late Checkout delivered the product, they were impressed and started giving more orders to the company. Greg says that they kept delivering other design works without asking for payment. I wonder who does that. Then one day, the client stopped giving them orders, and all the communications were stopped.

The Late Checkout team tried contacting the client but they got no response. This was the time when the “finance and operations” team asked the CEO to step in and take matters into his own hands.

The CEO thought it would be waste of time to an email that will “fall on deaf ears” or hire an expensive lawyer to sue them, instead he had the idea of using ChatGPT to generate a scary email that would grab the attention of the client. I mean, yes, it is completely normal, any person in crisis would think of this.

Greg asked ChatGPT to pretend to work in the finance department and generate a scary email that gets the client to pay for $109,500 of service used and inform that he has not responded to the 5 emails sent earlier and their invoice is 5 months overdue.

This was the prompt that Greg gave to ChatGPT:

Pretend you work in the finance department and your job is to collect payments from clients. Draft a scary email that gets XYZ client to pay for $109,500 of services rendered but hasn’t responded to 5 emails. Their invoices are 5 months overdue.

This was what ChatGPT generated for Greg:

Subject: Final Notice - Urgent Payment Required for Overdue Account

Dear XYZ Client,

We regret to inform you that despite several attempts to contact you regarding your overdue account, we have not received any response from you. Your account is now 5 months past due, and your outstanding balance is $109,500 for the services rendered.

As a responsible company, we have always given our clients the benefit of the doubt and provided ample opportunities to make payments. However, your lack of response and failure to settle the outstanding balance has forced us to take serious action.

We remind you that failure to pay the amount owed may result in severe consequences, including legal action and damage to your credit rating. We urge you to act immediately to avoid any such consequences and pay the amount owed within the next 3 business days.

If we do not receive payment or a satisfactory response from you within this time, we will have no choice but to escalate the matter further, and all costs incurred will be added to your account balance.

We understand that you may be going through difficult times, but we have a responsibility to our shareholders and employees to ensure the timely payment of all outstanding balances. We hope that you understand our position and take immediate steps to settle the overdue amount.

Thank you for your attention to this matter, and we look forward to receiving payment as soon as possible.


Greg stated further that he made a few minor changes and sent the email to the company and an executive of the company replied “Let’s get you guys paid” after a couple of minutes. I don’t know why this sounds kind of fake. I mean the email was good but it wasn’t that scary and I don’t think an executive would have time to check his emails when his company is facing a tough time and unable to pay the amounts for the services used.

Greg neither mentioned the name of the company nor does he showed any screenshot of the email.

At last, he promoted his new forum where people can come to discuss how AI can be productive. I guess, he probably made all this up for promoting his new forum.

He also promoted his new subscription service Dispatch, where his company charges $5 per month for making unlimited website designs, illustrations, etc.

There is also a chance that ChatGPT came useful in collecting a debt. He should be more open to the public and at least disclose the name of the company in an official statement.

Many people appreciated the clever use of ChatGPT but some pointed out that all of this is made up. One user said, “this is scary” while another said, “even though you didn’t want to send an email out of dear it would fall on deaf ears, you asked AI to draft a scary email for you?”

Let me know what you think of this incident. Is this true? Can ChatGPT replace expensive lawyers in sending legal notices?

Written by Mayank Vikash

Published on 3rd March 2023 at 10:15 IST

Last updated Mar 3, 2023, at 10:20 IST