How I Used ChatGPT and Chris Voss Style Negotiation to Save a Land Deal Today

I want to walk you through something that happened today in my land business, start to finish, because it shows how much money can be won or lost based on the exact words you send in one email.

This was not theory. This was a real transaction that was about to fall apart.

The situation

I have a deal in escrow where a former member of an LLC needed to sign a release so my son Moses and I could close on a piece of land on November 26th.

He is an attorney.

He had already agreed verbally to sign the release.

We agreed I would pay him $1,500 for his time.

On November 7th, I sent him the documents to sign.

After that, nothing.

No email.

No questions.

No pushback.

Just silence.

Time kept moving, and this is not a huge deal, but if it did not close, we were walking away from $15,000. My 20-year-old son, Moses, found this one virtually driving for dollars, and he has been proud of it, so watching it stall out was frustrating.

Most investors at that point would shrug, say the guy ghosted, and move on, but that ain't me.

Where ChatGPT and Chris Voss come in

Instead, I opened ChatGPT.

I typed out the entire situation in plain language. Who this guy was, what he agreed to, the date I sent the documents, how long it had been, and what was at stake for me and Moses.

Then I told ChatGPT something like this:

Help me write to him in a Chris Voss style. calm, respectful, no pressure. I want to bring him back to the table if possible.

Chris Voss wrote “Never Split the Difference” and was an FBI negotiator. His approach is built on tactical empathy, asking calibrated questions, and staying calm so people feel safe enough to respond.

ChatGPT and I went back and forth until the email sounded like something I would actually send in real life, not a robotic legal letter.

Here is the email I sent. The email ChatGPT helped me write

Good morning Patrick,

I want to check in with you because I am trying to make sense of where things stand. I may be completely off, but it feels like you have stepped away from helping with this. You might feel like this has become more complicated than you expected, or that getting involved again with the old LLC is something you would rather avoid altogether. If that is how this feels to you, I understand, and I do not want to make assumptions without giving you the chance to tell me directly.

When we talked a few weeks ago, you were very clear about being willing to sign the release so the LLC issue could be resolved, and I agreed to compensate you for taking the time to do it. I appreciated how straightforward you were on that call because it helped me understand exactly what was needed to get this cleaned up.

Since I sent the documents on November 7th, everything has gone quiet. At this point, it looks like the transaction may not survive, and I am trying to understand what changed on your side. I run this business with my twenty‑year‑old son Moses. He is the one who found this opportunity, researched it, and brought it to the table. He has been fully invested in getting this across the finish line, and right now we are both trying to figure out what happened after our conversation with you.

Did something shift that made signing the release a problem for you?

What is the real obstacle you are facing with this?

Is there any circumstance where helping us close this still makes sense for you?

If you have decided you do not want to be involved, I can respect that. I am not here to pressure you. I only need clarity so Moses and I know where we stand and what direction to take from here.

Thank you for letting me know.

Best,

David DeSilva

His response 10 minutes later

This guy had been silent since November 7th.

Here is what he wrote back today, right after that email:

“Sorry, my PC died. Just bought a new one yesterday. Two things.

Please confirm by email that if I do not receive the $1,500 dollars then my acceptance of the offer is automatically revoked. Please also confirm that you understand that I am making no representations or warranties of any kind and that I will be held harmless regarding any claims associated with the transaction contemplated by the documents.

Once you confirm by email I will sign the docs.

Sincerely,

Patrick”

In other words, he is back in with clear, reasonable conditions. One confirmation email from me, and he will sign in DocuSign.

Transaction saved.

Why this worked

I am not sharing this to say I am smart. I am sharing this because the tools are sitting in front of us, and most people never use them this way.

That email did a few simple but powerful things.

It acknowledged how he might feel, including that this might seem like a headache he does not want.

It reminded him of his verbal commitment without accusing him or attacking his character.

It asked clear questions, making it easy for him to respond.

It stayed calm, even with a lot of money on the line.

It made it human by mentioning that I run this business with my son Moses, who found the opportunity.

That is straight out of the Chris Voss playbook. Tactical empathy. Calibrated questions. No emotional spikes.

ChatGPT did not replace my brain. It slowed me down and helped me get the words right.

How this applies to other land investors

Here is the part that matters for anyone who invests in land.

You can do this too.

The process is simple.

Tell ChatGPT the full situation like you would tell a friend.

Tell it you want to sound calm and respectful, similar to Chris Voss.

Tell it your goal, for example, to bring someone back to the table, clear up confusion, or get a straight answer.

Then work the draft with it until it sounds like something you would actually say.

Today, one email like that kept a fifteen‑thousand‑dollar deal alive for me and my son.

For land investors, this is the part most people ignore. We spend hours doing due diligence, running comps, checking zoning and topo, and then we fire off sloppy emails or texts in thirty seconds.

The right words, in the right tone, can save months of work. I hope this helps at least one person today!

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