September 4, 2023

How I Used ChatGPT to Get $500 Back from a Sneaky Rental Car Company

By Paul William

September 4, 2023

Disclosure: Some of the links below may be affiliate links which means I receive a commission, at no extra cost to you, if you make a purchase through them.

Alright, let’s get straight to it.

Last month, I found myself caught in the crosshairs of a major international rental car company that apparently had no qualms about charging me ~500 bucks for damage I didn’t cause.

I had undeniable proof of the pre-existing damage, but despite presenting it several times, the company’s incompetent customer service employees kept denying a reversal of charge.

They clearly didn’t know they were messing with a neurotic man armed with next-generation technology and decades of pent up rage, soon to be unleashed on their C-Suite and legal department. Oops.

Here’s how I used ChatGPT to wage war, recover my $500, and snatch victory straight from the jaws of these low-integrity corporate sharks.

The Clash Begins

These predatory clowns had the audacity to claim that I had caused some damage to their vehicle, damage that was there long before I had even laid eyes on that car.

They wanted to snag a cool $500 off me, a plan I was about to annihilate with extreme prejudice.

You see, for years, I’ve taken video walk-arounds of any rental car I pick up before leaving the lot.

I always had a sneaking suspicion that one of these days I’d get unlucky and the rental car company would attempt to charge me for pre-existing damage.

And I was right.

I supposed I could always just pay for the rental car company’s insurance policy and avoid this whole possibility. But I have personal car insurance that covers me in rentals, and never thought it would really be an issue.

And even so, I’m definitely not paying a personal insurance deductible for damage I didn’t cause.

A Hidden Charge and Denials

To underscore my rage, it’s worth noting that I was never actually informed of this charge and only noticed it when reviewing my credit card statement and being faced with confusion.

At that point I reached out to the company, who only after prodding and several days of research were able to tell me it was for damage to the car.

They then proceeded to send me barely visible, blurry pictures in a PDF document as proof.

At this point I presented them with photographic and video evidence containing time stamped and geo-coordinated files with a time, latitude, and longitude placing me at the rental car location mere moments after getting the keys, showing the pre-existing damage.

But apparently that wasn’t enough, and after several weeks of back and forth, with me throwing the evidence in their face, they still refused to return my money.

Gathering Ammo with ChatGPT and Tracking Down Executives

I was pissed off and tired, but wasn’t about to roll over and play dead.

But I also didn’t want to spend thousands of dollars on a lawyer or turn this thing into a legal time dump. I just wanted my money back.

So I turned to ChatGPT.

For those of you living under a rock, ChatGPT is large language model artificial intelligence software that you can talk to like a human, and it can talk back.

It can take on a variety of roles and summarize knowledge from a wide variety of sources to give you relevant information. In tests, it’s passed both medical board exams and the bar exam. I’ve personally used it for travel planning in the past.

It’s not perfect, and it’s definitely not a trustworthy replacement for any real legal or medical advice.

But often it can help explain relevant concepts and get close enough to where it’s quite useful as a starting point in research.

I explained the insane situation and timeline to ChatGPT, then asked it to write an email to the CEO and General Counsel of the rental car company explaining the situation and calling for a solution.

Consider this your explicit disclaimer that you should probably not do this yourself or use any automated technology for legal matters. Even though it worked for me, I’m not a legal professional and I’m sure this could backfire in some cases. I’m just sharing my personal experience.

Email #1 to Executives

Below is the first email I sent to the CEO and General Counsel. This was written 95% by ChatGPT.

I’ve blurred the names of the executives and the company because I’m not looking to get into a public pissing match. I’ll explain how I hunted down their contact info later in this post.

ChatGPT Car rental demand letter

But it still didn’t work!

This first email definitely got someone’s attention, because the next morning I heard back before 8am with the following email:

Unfortunately their email reply this was just another display of ignorance, so I had to bring out the big guns. However this time I felt confident knowing that my emails were reaching the right people.

Law School in 5 Minutes

Unsatisfied with their previous pathetic response, I decided to go nuclear.

I tracked down the contact details of ALL the company’s top dogs, including the CEO, General Counsel, Head of Americas, supeona compliance department, etc. They were about to get it with both barrels.

This next email wasn’t going to be just a complaint; it would be a declaration of war: back down, or face the wrath of a legal hurricane.

To start I used ChatGPT to learn about legal concepts that could be applicable.

After a robust conversation, I told it to “use all of the concepts we discussed to draft another email to these same executives. Be forceful and concise.”

Here’s what it came up with, which I sent to the CEO, General Council, Head of Americas, and a compliance email address I found online.

After that, all that was left was to await their response to my second warning shot.

I giggled as I re-read the perfectly intense email sign off that GPT helped concoct:


Well, that did it folks.

Just an hour later, I received an email confirming all charges would be dropped and they would also reimburse me for fuel expense and some other charges as an apology.

As it turns out, all it took was me threatening to sue them for them to magically “find the evidence” I had previously provided.

The money is now back in my account.

There’s a lesson in here somewhere…

Finding the Executive Email Addresses

Now, you might be curious how I found the email addresses of these high powered executives in the first place.

I was only able to reach a resolution after sidestepping customer service entirely and writing straight to the C-Suite, but this raises the question of how I got their contact info to begin with.

It was simple.

I just trawled googled until I found the company email address of a lower level employee, then applied that format to the executives names.

For example, I found a lower employee whose email address was and then found the executive’s names and sent it to CEOFirstName_CEOLastName@…. you get the idea.

A Battle Cry for All the Mistreated

This wasn’t just a victory for me; it was a powerful message to all those corporate behemoths out there. With the might of technology like ChatGPT at our side, no unjust entity can stand against us.

This was a testament to the indomitable human spirit, assisted by the relentless power of AI technology.

Remember, when faced with injustice, tools like ChatGPT are here to help you fight back, to help you not just stand your ground, but to dominate.

Until the next battle,


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