This episode reveals how Claude prevented legal escalation on the messy Texas title deal when the seller ghosted right before closing after 8 months of cooperation and $5K in hard costs. The AI-assisted approach combined Chris Voss negotiation tactics with Brené Brown empathy to craft emails and voicemails that subtly indicated persistence without explicit legal threats—though the seller ultimately returned due to hospitalization rather than the prepared outreach, validating the strategic framework for future similar situations.
Key Takeaways:
- Too Legal Too Early Destroys Rapport Initial email drafts skewed heavily toward legal language which would have eliminated friendly resolution options—Claude identified this immediately and redirected toward empathy-first positioning that maintained relationship capital.
- Clarifying Questions Unlock Better Prompts Claude requested specifics about the seller’s motivation ($110K for mom’s house facing tax foreclosure plus dialysis costs), sister relationship dynamics, and 8-month timeline frustration—details that enabled emotionally resonant messaging impossible from generic templates.
- Subtle Persistence Over Explicit Threats The final message stated “we’re not going anywhere” and “we’re a team here” without mentioning legal options, creating firm positioning while preserving the collaborative tone built over months of title work.
Listen to the full episode for the complete AI-assisted negotiation framework and specific Claude prompt engineering techniques that produced relationship-preserving legal pressure.
(Podcast transcript below)
Welcome to Get Serious. Excited to be diving into this one today here because it’s pretty much a U-turn from some of those brewing legal situations that were kind of hitting back to back last week that you heard me talk about here. in pretty much an hour of each other, we were able to find
paths forward one more cleanly than the other here. So I want to update accordingly as well as some of the lessons learned as we were, you know, trying to pursue next steps. So, you know, one of those key ones was related to that messy title deal that, you know, we’ve been working on for eight months. I know I mentioned it roughly 38 acres in Texas and
crazy airship situation and it seemed like last week that the seller who had been working with us every step of the way collecting his family members that he was the one who suddenly got emotional and cold feet after a difficult conversation with his sister, of estranged relationship, potentially about airship issues, just went cold.
ghosted us for a couple of days and so then we were really considering, how can we try to loop him back into the fold here? Is there way to sort this out in a more friendly manner before do we consider going after this property in a legal direction? We were already really tight on committing any extra funds.
And it would have been a tough call to determine how much more we would have been willing to commit. And we were already, you know, 5K deep, roughly on the property. Plus all that time involved in the deal. And so as we were.
You know, trying to figure out this situation based on a suggestion from the title attorney who’s working with us. like, Hey, you know, try reaching out in more friendly manner email, maybe a voicemail, give them a few days and then you can try to start accelerating. our land investor partner on the deal prepped a draft of an email. I had asked, Hey, can I review it too? Cause yeah, really we were going to feed this into Claude and try to reorient.
That’s just, you know, standard procedure really for any difficult conversation at this point. And the initial draft, you know, even myself personally, felt, and again, I’m not really involved with the seller, so I’m not sure the exact relationship that might’ve had, but it just, seemed too legal heavy. And this was similar to another property we were working on. know I talked about a few weeks ago that it had a neighbor encroaching on a property that we were about to sell.
And they were very friendly. were able to work it out. But like the initial draft that our broker prepped was just too legal heavy. Like, it, it just bears worth mentioning, like, unless you’re really going to go all in and try to, you know, and, be willing to commit the resources necessary from a legal side, like, and even then, even if you do have that, like it’s just better for everybody involved and less costly if you can sort it out without having to do that. So.
You know me plugging this into Claude. It was like, okay, can we use a combination of I forget the exact phrasing but like, know using the Chris Voss Never split the difference mixed with kind of the Friendliness and empathy of a Brené Brown for instance. She’s really a famous social worker How can we reorient this? Email to the seller to try to loop them back and fold in like the
you know, critical element here is like, yeah, if we don’t get it to work with this route, like having the email or a voicemail work, it’s like a real crap shoot if we’re going to commit any resources to go legally. So like this kind of like really has to work. So, you know, Claude, I need you to do your best here. And then that type of phrasing works. And so they came back with similar feedback, like, this is just too legal heavy.
And they were also asking some clarifying questions because they were you know, again me not dealing with the seller But I had heard from our land investor. Hey, this seller was emotional crying with him on the on the last phone call So Claude was like Okay. Yeah, we we really want to back off the legal piece here Like what problem were you trying to solve and some of this is like, you know kind of standard?
you know, empathy driven problem solving type directions of speaking with sellers. know like Ajay and some of the other, better sales folk within the industry. We’ll talk about this, like, okay, meeting the seller where they’re at, you know, what problem are you trying to solve? Reiterate that. and so that was what some of the clarifying questions were. Okay. Going back, what was the seller going to use this money for? you know, can you dive further into the relationship with his sister? Like what?
what really seemed to be the crux of the problem there. And again, they didn’t know how much we were buying the property for like 110K roughly. You know, he was asking, okay, what’s the amount, how life changing is this? Like any other concerns that could have been brought up? Like what type of relationship did you have with the seller through this? Was it more transactional? Was it more, you know, friendly and rapport driven? And again, we weren’t having, you know, direct combos with the sellers. So I had to send all these back to the land investor. Hey, can you…
answer these the best of your ability so we can feed this back into our model. And he got back to us right away. He’s been excellent to work with, very communicative. And yeah, I mean, there were some, you know, problems within the seller’s life that was outside of just like looking to make some money on the land deal. You he had his
Mom’s house that was facing a tax foreclosure and needed money to pay off that plus he’s been dealing with Or the ongoing dialysis treatments that’s just been a huge headache huge, you know burn from a money perspective to so he’s been needing these funds plus like been waiting eight months they is taking forever to do this close and You know some of the question so we’d like we had that motivation there and then we had
Info about his relationship with his sister, which again was just a strange You know difficult they haven’t had the best relationship his sister was cut out of any inheritance from Their mom when she died and so like this was I think the first time they had been in touch when the seller needed to get her as like a affidavit of airship
Signing done and it was difficult conversation because who knows she might have You know been trying to convey. Hey, I should have a part of this too and so forth. I don’t know But you know family situation could be tricky. So it’s like, okay, do we need a remark on that? And again like targeting hey, this is kind of like life-changing money here and so we fed all that back into quad and it gave you know much more
emotional, connective response really, you know, tying into like, we’ve been a team from the start here. You know, I’ve been with you every step of the way, like, remember, you’re going to use these funds to pay off your, your your mom’s it really your family’s house that’s facing tax foreclosure. And by the way, like, I mean,
can’t really comment, I don’t know what your relationship with your sister is, but hey, if you have this money, you can have the choice on doing what you will with it. If you want to be able to help her out, your choice, just, you know, potentially presenting it that way while remaining sensitive to the issue. Also reiterating, hey, you know, these title company docs, like, you know, can be, you know, scary to sign all these, like I’m gonna be on the phone with you, walk you through during the…
during the process here. And really not mentioning anything from the legal side, just like a check in more empathetic, hey, how are you doing? We’ve been in touch before. Can you just try to reach out? You know, just send me a text like you’re that that you’re doing okay there. But you know, also mentioning, hey, we’re not going anywhere. We’re a team here. We’re going to be with you through through this process. So like that was
really the more firm point in terms of like, we’re going to be pursuing this, but that was just the lightest touch that like we will pursue this property, but otherwise nothing mentioned from a legal side here. Because again, we wanted to maintain a lot of friendliness and orienting around the rapport that our land investor had built with the seller to this point.
And then we also asked Claude, OK, draft another potential voicemail, assuming the email doesn’t get answered to or, you know, we have to try calling. And we’re also going to, you know, we’re going to send this email on Friday, give them the weekend to respond, try calling again on Monday. And here’s the voicemail. And that just like, you know, slightly upped the the pressure here. Actually, let me pull up. Let me pull up the copy because
Where was this? Okay, negotiation strategies, sister angle, yeah.
Yeah, so the voicemail, we oriented it. And again, this is why you have to always go back with AI because like the first voicemail it was saying, you know, I’m still here to help you do that, you know, trying to save your mom’s house, like no pressure, just when you’re ready to talk, I’m here to carry yourself. But I had to go back and I’m like, well, that’s not accurate. Like we can’t say there’s no pressure, like when you’re ready to talk, we have to have some type of timeline here.
so you, so you got to reorient it back and, and, you know, ask it to fix. And so, and with that in mind, you know, the revised voicemail script was like, okay, I understand you need some time to process everything, but I also need to be honest. Like we can’t leave this hanging indefinitely. So, you know, when you’re ready to talk about how, we move forward together, I’m here. Please give me a call back when you get this, take care. so can see it’s slightly.
It’s much easier for me to correct AI and how I sound, or if I know the relationship I’ve had with somebody, but if I haven’t been privy to any communications and I don’t know how to land investor, our partner in this deal was talking with the seller. So I had to say, okay, look over this, but you you might have to adjust some of this to your voice here. If it sounds too unrealistic, like I just don’t have that information to determine one way or another.
and my scheduling wise, do it make sense to call on a Monday is usually available then not sure what this guy’s situation is. So, like we might have to make some adjustments, based on, on the underlying mechanics of. They’re kind of ongoing communication. but we sent all that over and again, like I paid a lot of like really, really focused on trying to get this right because like, yeah, we want to nail this a hundred percent.
again if we screw this up or the seller doesn’t come back here, there’s a very good chance that we won’t be able to pursue this or it’s already going to be a borderline deal. Probably the amount of extra cost we had involved in this anyway. So it was just tricky from that perspective but pretty much
Right as I sent that email and spent all that time on that, I got an update from the land investor that the seller had called back and he was apologetic and was saying, I’m sorry for the previous call, not answering. I was in the hospital for a couple of days, like low blood sugar or whatever. And we have to take that at face value. Either way, he came back in the fold and was like, okay, yeah, let’s schedule the title company. I’m ready to sign on, on Monday.
and let’s get this done. And so like, obviously that’s a a huge sigh of relief that we didn’t have to go through this, this whole rigmarole that we had just prepped for. And, but you know, who knows it could not have worked out that way. But we, you know, really lucked out from that perspective again. Luck is not a strategy, but you know, we’re coming up with how are we going to deal with this.
process and so we have the steps in place on how to handle this in case it doesn’t work out in our favor in the future because sometimes we have had to put some more pressure on sellers before. Then I have a couple other tidbits about the actual closing process with the seller. I’ll save that for the next podcast actually. It’ll be a little bit shorter but some really key info. So I will catch you on tomorrow’s pod.
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