Win a $2,100 settlement from a tow driver who dented a car, with guidance from ChatGPT and Gemini

Posted

Jul 8, 2025 by Bill Eerdmans (LinkedIn)

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Last checked

Oct 17, 2026

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Method:

How we verify

Evidence: Described by posterThe person describes what happened in words, without screenshots or video.

Outcome

With no pre-tow photo and a dent left by a tow truck driver hired by his apartment, a poster asked ChatGPT o3 and Gemini 2.5 Flash whether to claim on insurance or leave it. Both suggested settling directly with the driver, who also lacked a pre-tow photo. Over five weeks, with o3's guidance, he built an email trail, set deadlines and asked for evidence, and says he won a $2100 settlement in 35 days.

Agent

ChatGPT, Gemini

The source didn't share its exact prompt, so we wrote this from what it describes.

Let's work this out together. I'll tell you what I know, you suggest options and ask what you need, and we'll narrow it down step by step. Nothing gets booked, bought or sent until I say so.

Goal: Decide how to recover the cost of damage to my car and run the process step by step.

What I'll share as we go:
- What happened, when, and who was involved
- Photos and repair estimates
- Messages so far
- My insurance details and deductible

Rules:
- Compare options: insurance claim, direct settlement, small claims, with pros and cons.
- Help me write calm, dated emails with clear requests and deadlines.
- Keep a log of every contact and missed deadline.
- Explain small claims steps in my area using official court sites.
- If a site asks for a login, a CAPTCHA or payment details, stop and hand control back to me.
- Ask for my OK before you pay, book, send, submit or cancel anything.
- Check facts that can change (prices, opening hours, dates, availability, rules) against the official source, and tell me anything you couldn't verify.

Output: A recommended route, email drafts, and a running case log.

You'll know it worked when: I get paid for the repair or am ready to file in small claims.

Let's work this out together. I'll tell you what I know, you suggest options and ask what you need, and we'll narrow it down step by step. Nothing gets booked, bought or sent until I say so.

Goal: Decide how to recover the cost of damage to my car and run the process step by step.

What I'll share as we go:
- What happened, when, and who was involved
- Photos and repair estimates
- Messages so far
- My insurance details and deductible

Rules:
- Compare options: insurance claim, direct settlement, small claims, with pros and cons.
- Help me write calm, dated emails with clear requests and deadlines.
- Keep a log of every contact and missed deadline.
- Explain small claims steps in my area using official court sites.
- If a site asks for a login, a CAPTCHA or payment details, stop and hand control back to me.
- Ask for my OK before you pay, book, send, submit or cancel anything.
- Check facts that can change (prices, opening hours, dates, availability, rules) against the official source, and tell me anything you couldn't verify.
- Get a written repair estimate before naming a settlement figure.

Output: A recommended route, email drafts, and a running case log.

You'll know it worked when: I get paid for the repair or am ready to file in small claims.

Before you finish: re-read my goal and constraints, check your answer against each one, and list anything you assumed or couldn't confirm.

Source

https://www.linkedin.com/posts/williameerdmans_genai-chatgpt-o3-activity-7348421812793262080-FX2c