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3 contributions to Leadership in Land
Everyone has that deal… what’s yours?
What’s one land deal that changed the way you think about business or life? Not the biggest profit. Not the cleanest flip. But the deal that taught you something you didn’t expect---about people, patience, risk, or yourself. Sometimes one property… one seller conversation… or one mistake… can completely shift how you operate. Curious to hear your story.
2 likes • 27d
For me, it was my very first infill lot deal. I got it under contract and was fired up because I thought I had finally found my lane. Then a few weeks later it fell apart. The seller had bought his house and the vacant lot next to it together, so even though the lot looked separate, it was still tied into the mortgage on the house. He hadn’t paid the loan down enough for the bank to release the lot, and that killed the deal. That one stung. I felt like an idiot, but it ended up being the deal that changed the way I do business. From that point on, I quit taking anything at face value. I got deep into deed history, county records, mortgages, liens, code enforcement issues, tax ledgers, all of it. I started verifying everything for myself instead of assuming the paper trail was right. Since that deal fell apart in October 2023, I’ve only had one other deal fall out, and that one was because I moved too fast and didn’t trace the deed history back far enough. Fast forward to today, and that same lesson is the reason I just picked up a 50 x 150 buildable infill lot for $2,000. The owners bought the property in 2000 for $30,000 on seller financing, so that deed of trust was in first position. Then in 2004 they got two city sponsored rehab loans that were meant to help them make repairs and updates to the home. Those city loans were in second position behind that original seller financed deed of trust, which turned out to matter a lot. Then the house was torn down in 2013. Once that happened, the value was gone. So in June 2014, the city released one of those rehab liens because there really wasn’t any value left there for them to chase while sitting in second position. But the first rehab loan from January 2004 was still sitting there. I cleared that up within the past couple weeks. I sent the city the supporting records and releases, and within a couple of days they released that first rehab lien too. Then I sent the original seller financed deed of trust to my title company and found out it was no longer enforceable.
0 likes • 23d
@Dave Denniston yeah the way those balloon so much and sometimes so fast is why a lot of infill lots go to auction.
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.
0 likes • Nov '25
@Dave Denniston you're welcome!
0 likes • Nov '25
@Mary Ann Danielson that's awesome, and I couldn’t agree more.
Need Your Vote!
What module should I put out next for the Leadership in Land course? Have another suggestion? Let me know in the comments!
Poll
18 members have voted
1 like • Sep '25
@Dave Denniston done
1-3 of 3
David DeSilva
2
14points to level up
@david-desilva-1339
Arizona Realtor/Virtual Land Flipper

Active 23h ago
Joined Aug 12, 2025
Gilbert AZ
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