I’m Steven Jack Butala.

I’m Jill DeWit and this the Land Academy Show. For ten years and counting, Land Academy has been the place to go for the education tools and support you need to start or grow your land investment business. There is no more experienced or seasoned land investment group out there.

How AI Is Transforming Land Investing—& What It Means For Your Future

Our topic is one I spent a bunch of research time on. It’s called What Your Land Investment Business Looks Like with AI. It’s Your Survival. Did I get an education during the process for this. I’d love to share all of this with you.

Did you use AI to ask about AI?

Yes.

There we go. How did that go? What did AI say?

It seemed to be, which is very strange, more happy than usual to tell me about how my life’s going to go. I say this positively because AI seems to have a personality. It strangely matches my personality. It’s scary.

That makes me worry a little bit. When you said how AI is going to tell me how my life’s going to go. What if I’m talking to AI about my health? Is it going to come and say, “Jill, you are five years’ away from falling apart.”

That probably thinks that.

“Jill, if you keep acting like fill in the blank or you keep up with this habit you have of fill in the blank.”

It sounds like your mom. “Your behavior is not acceptable.”

Is AI going to be like my mom?

Probably, if you let it. It responds to you. I told it to stop being so positive. I’ve been saying that since I’ve been using it all throughout 2026. I feel a little bit late to the party. I don’t think we are. Certainly, not with land, but as a regular user.

I don’t think we are.

I agree.

The only people I know that are ahead of it are at a university. They’ve been helping design it.

In Palo Alto. I broke the whole topic down. We’ll get to it in a minute in four sections. 1) How to find property. You know how we do it by sending out blind mailers. 2) How to do the intake, do the due diligence, qualify the deal whether or not you want to buy it, and reprice it if it needs to be. 3) Get the title going. Get the deal purchased. 4) Get it sold. Every single one of those four points, the concepts are all the same stuff we had been doing since the real late ‘80s, early ‘90s. We’ve been saying this for decades. The tools and how to implement this stuff are totally going to change. They have changed already. This is a fun episode.

How many times have they changed even since you’ve been doing this? It’s not like it’s any surprise.

Real Deals, Hard Lessons, & How The Game Is Changing

We didn’t have Google Earth when I started this. We couldn’t get plat maps. Is it a big massive challenge for us? No, but we’re going to share it with you. Before we get into it, though, we’ve got a bunch of questions.

Actually, some wins. I love this. These are just wonderful nuggets of what’s going on in our world and with our Land Academy community. Matt wrote, “Biggest deal yet. Purchase price $54,000. No improvements.” Which is our rule, anyway. “Listed with an agent, sold for $185,000.” I love this closing statement to closing statement on the buy side and the sell side. It was $123,000, $869.98. Closed on the buy side in September 2025 and then just sold it in March 2026. Whole time was around 60 days. By the time we went under contract, I guess it closed.” That’s so great. I love it. Carl wrote, “I tried owner financing on a $25,000 deal and the first payment just hit my account.” Passive income.

Could be the last, Carl, but I’m happy for you.

I just had a talk with that about somebody who’s working on that. It’s like, “Please tell me you agree with me that you’re not going to get rich on $2.50 a month.” She goes, “I know that.” I said, “It’s fun when it’s all automated and everybody pays. Six months from now, when who-knows-what happens to their job, you know that food’s going to come first. Not this.” She’s like, “I’m ready for it.” I’m like, “It’s not my jam anymore.”

Mikey said, “I just successfully double-closed my first property. I learned a lot and I’m never going to do it again. I did it because I couldn’t talk the seller down from 60% of retail. I couldn’t get the deal funded. No kidding. There was still a good profit. It all worked out, but it was significantly more complicated and time consuming than my regular deals.”

As you’ll find out a little later in the episode, everybody, this is not going to happen anymore. Entire municipalities all over the country seemingly simultaneously are cracking down on dual closings and a bunch of other stuff. We’re getting regulated. We haven’t been regulated. This industry has been relatively unregulated forever.

Claudia wrote, “Completely overpriced mailer, but I got a seller drop their price by half over the phone.”

You found a real seller.

That’s the thing. I was talking recently, too, about this. I just had a great conversation for an hour with a Land Academy member for several years who keeps doubling and then some every year as it goes. We were talking about, “You’re going to make a mistake.” People come into this and they’re afraid to send the mail out.

Sometimes, they’re afraid they’re going to make a mistake on pricing. Sometimes, just answering the phone, whatever it is. She’s like, “Prepare yourself. You’re going to make mistakes and that’s okay. You just plan for it.” The happy mistake is when you overprice a mailer. I don’t recommend this as a model because your phone blows up. You often will get more feedback. You got to weed through them all. Pick the ones you want, come back with them, and talk them down. That is harder to do, but it can be done.

That changes with AI.

That’s the thing. It’s maybe how you set up your pricing and the tools. The tools you use for pricing will improve and change, no problem. The person on the phone, that will never change.

Urgency Of AI In Land Investing

Spoiler alert. There’s no more pricing. Our topic, “What Your Land Investment Business Looks Like With AI. It’s Your Survival.” I broke this down in, as I said earlier, four categories. I’m going to call the first one, which is locating property. By the way, in no way is this our old model obsolete. I’m just trying to force this issue so that we stay on top of it like I have for decades.

You want us to think about this and be ahead of it?

Yes. This is free thinking.

This is what’s probably coming.

AI Evolution: From Tools to Agentic Automation

Most of it’s here. It’s not in a format that’s so incredibly usable that you can just sit. We’re all used to using a large language model generative ID. We type in. It gives us an answer. We say, “That’s amazing. I got a real direct answer. I know what to go do myself out on the internet.” What we’re talking about is, for the large part, a genic AI.

AI Replacing Manual Work (Automation Shift)

The second part of that, instead of me going out on the internet and doing all this stuff and calling people, it does it for you. It’s shocking. Most of it is here. You have to piece it all together all over the internet, everything in the beginning. In the next couple of months, or maybe let’s just say six months. It will be much more user-friendly.

Instead of you going out on the internet, doing all this stuff, and calling people, AI does it for you. Share on X

Stage 1: Data Scout (Finding Opportunities Through Triggers)

The first of the four breakdowns in how you buy and then resell a piece of land is as follows. I called it the Data Scout. You can write an application. Not even that, just request or create a bot that continually monitors whatever you tell it to monitor. It could be somebody stopped paying their water bill if you buy and sell houses.

It could be somebody passed away and a probate got filed that day. They went into foreclosure. There’s a tax lien that got paid onto it. They stop paying their mortgage. There’s all kinds of triggers all over the internet that may make sense to you, as what Jill was talking about earlier. There’s art to this. You set the triggers.

You can’t just say, “AI, go find me a great piece of seller that really wants to sell their property under price today.” You can try that. It may get that to that at some point. This very first actionable AI, you have to tell it what to do. You can set it up to do that. You’re only getting the properties that have these triggers. Maybe they listed it, the listing expired for a certain price that is acceptable to you. You have to get real creative and figure out what you want your data scout to do.

I see this as a benefit too. I’m not worried about this because it only knows I’m the pro here. It’s not the pro. It’s going to take a while. I still think there’s so much art to this. I never doubt this more, that it can’t do. That’s great for me.

Don’t stop what you’re doing, but set aside some serious time on your calendar to prepare for a huge change. AI is going to make your life easier. Share on X

That still drops deals in your lap. It’s the same net effect. It is sort of a genic. In Jill’s case, she would say, just like what she does. “What should I do?” Sally Smith wants to sell her property across town. It fits all the categories just like if we sent the mailer out. Sally Smith called Jill back. Jill is going to figure out how to contact her. Drop all this news on her and say, “We can solve this problem for you on Thursday.” It’s just a different way to get there.

Am I still mailing offers?

Don’t stop mailing offers. You just got off the phone that somebody doubles their money every year. I’m not saying this is obsolete. I thought two or three times to myself, “Should we be talking about this?” I don’t want you to stop what you’re doing. I want you to put some serious time in your calendar, like you have because you’re reading this, to get ready for a huge change. It’s going to make your life easier. We’ll be there. Land Academy will be with you every step of the way, Jill and I will.

Stage 2: Intake Officer (AI Handling Leads & Due Diligence)

Stage two, the Intake Officer. You’ve probably already heard about this. AI talks to you on the phone like a regular person. When these lead calls come back in or if you’ve got your genic thing to somehow get a note out, which I don’t understand how that’s going to work with spam rules yet. You get lead calls or emails back in, or you just do an outreach. In Jill’s case, we would do an outreach. There’s all kinds of things that can be collected through the data scout once you do that outreach. Is the property landlocked? Can I get an ALTA survey or a plat map?

All kinds of, let’s call it, preliminary phase one due diligence. That’s what we call it in Land Academy to see if you want to do the deal. It’s not, “Is this an amazing deal? Let’s price it.” It’s the eight-hour, eight A’s. You can get the intake officer to smoke a bunch of that stuff out soon. If it’s a verbal transaction, it’ll be able to analyze the seller’s tone, the willingness for that person to sell, and on and on. I’m saying I put this episode together because I want this to get you thinking.

I don’t want to just blow apart all your beautiful work here.

That’s your job, Jill. That’s our lives together.

There’s still so much of an art to this. I can’t train AI to have a female gut intuition. You females reading this know exactly what I’m talking about, especially if you’re a mom. Your kid’s in the other room and you’re on the phone. It’s quiet. You know something bad is happening. That’s a fact. Everybody else would be saying, “This is great. I get some time to talk on the phone. No one even notices.” There’s a fire being lit. There’s something going on in the other room that you have to pay attention to. I don’t think I can train that to AI.

I talked to, again, this seasoned person, this gal, about picking up the phone. Especially as a woman and that intuition. I had a boat broker. When you’re a boat owner, you’re obviously always shopping for a boat. Maybe that’s how it goes. Anyway, we’re talking to this broker about another boat. We may or may not have put an offer on the boat. While we’re waiting for the sellers to come, here’s the funny thing that I picked up on that he didn’t pick up on. We put an offer on this boat.

The broker has been doing this for 40 years. He comes back to me and goes, “Jill, I’ll tell you this. This is the craziest thing. I got to the seller. They reviewed your offer. They’re trying to figure out what to do. They just told me to change the offer price and add $25,000.” I said, “I don’t think they want to sell, John.” I’m sure he just dismissed me, didn’t even hear what I said. To me, when you’re changing your offer price and you’re having second thoughts about selling something.

I’m like, “I don’t think they want to sell.” He’s like, “Let me get with them. I’ll get with you. They’re going to be back in town. We promise we’re going to have a longer conversation.” I went and looked. Sure enough, he changed the offer price online. I waited till the next day. He called me back and goes, “Jill, I can’t believe it. This has never happened to me since I’ve been a boat broker. They changed their mind. They don’t want to sell.” I picked up on that.

Savvy real estate agents are already using bots to scan LinkedIn for layoff signals—because job loss is the #1 trigger for people to move from one home to another. Share on X

I know what’s going on with Jill. This is the reason that Jill and I are very successful business partners together among other things. What excites me about the topic is that the more tech and the more STEM-type stuff that is involved in our industry, there’s less of a chance of human interaction for me on all parts. That drives Jill crazy.

Jill wants to feel her way through a transaction, adjust in real time to people’s sentiments, the way that they’re talking. The whole human, what I would call it, female intuition part of these transactions. We’ve made crazy amounts of money because Jill’s got this acute talent. I’ve kept her, at the pipeline, completely jammed full with my tech stuff.

All of this excites me because hopefully, I don’t have to do these things anymore. We just don’t have to. We don’t have to spend all this time in the distant future. Pricing and putting these mailers together, dealing with sellers on the phone all day on a Saturday. What Jill does talk to real estate agents and title agents. The older you get, you know what I’m talking about. If you have gray hair, there’s a lot less chance of being let down by a human.

You’re just going for volume.

I want to not talk to anybody. Dream with me for a second, you and the readers. I would like to, theoretically, write on a whiteboard what I want. I want to know the top five people in 85251 Old Town Scottsdale that are thinking about selling their piece of property, but they don’t know it yet. I would like them to magically be reached out to. Hopefully, by a bot or something like that.

This is all fantasy. It says, “We know that X, Y, and Z just happened. If you are interested in selling your property for X, please call me.” Whatever the call to action is. I don’t know what that is yet. “We will walk you through the process on how to get cash out of the property on Thursday, if that’s what you like.”

I just thought of something interesting. I know this is coming. Think of a bank. If there’s a bank that closes or some company closes, we all know who works for them. Do you know how we all know when it’s public knowledge? LinkedIn. There’s your people.

That’s a tiny little data store.

Right there off the top of my head. I know everybody who works there who’s on LinkedIn that puts it on there. That’s what they do. I’m going to reach out to them.”

I read a huge thing that savvy real estate agents scour LinkedIn for keywords and use bots to scour LinkedIn to see who’s losing their job. That’s the number one reason people move. Move out of their house and move into another one. It’s two transactions. By the way, what’s going to happen to real estate agents? I thought they were unnecessary in 1994. They’re still unnecessary, but I don’t know if they can legislate their way in and out of this effectively anymore.

Stage 3: Transaction Tech (Automating Closing Processes)

Number two, the intake officer, we talked about that, the inbound calls. Let’s just assume we want to do the deal. Number three is the transaction tech. These are my silly little names for the stuff. Once the deal is under contract and an agent can do that for you. It starts to go down the path of closing the transaction and all that’s involved with that.

There might be an insurance play if you’re buying a house. You’re certainly going to need lien reports. It automates what the title agent does pretty dramatically. You could, in the short term, serve this up on a silver platter right to the agent. Say, “There’s no liens.” You do this anyway, manually. “There’s no liens on it. It’s a cash deal. We don’t need any of this stuff that you typically are used to doing. No inspection, any of that stuff. We’re just ready to close. Let me know.” It could probably pull a title report for you. I’m sure it could. That’s huge. That’ll get all automated, too.

Stage 4: AI-Driven Sales & Outreach (Disposition)

Finally, once you own it, this is my favorite part of this entire thing. “Hello AI, please contact everyone that’s within a mile radius. Specifically people who have purchased or sold a purchased property. If it’s a house, you purchase a house. If it’s a piece of land or farmland specifically. Let them know that this property is for sale and what to do with the call to action. If they paid less per acre or paid less for the property that I’m buying, please let them know that right up front and tell them how to.”

That is crazy exciting to me. We implement at Land Academy a concept called Neighbor Letters. We carpet bomb everybody who owns real estate. When we buy a piece of property, we carpet bomb usually a mile radius, depending on the density. Everybody gets a letter from us saying exactly what I just said.

“We got this property. We probably paid less for it or it’s for sale for less than you paid your property. Give us a call.” It works 50% of the time. We sell 50% of our property that way. This is what’s coming. A lot of this capability is here. Please just make this part of your thought process, especially if you’re already buying and selling land. Stuff’s going to change, like with everything.

I’m not afraid of it. Are you afraid of it?

No.

Good. I’m excited.

I’ll tell you a real quick story. I started in commercial real estate in late 1989, and my Hoopla stint went from then to about 1995-1996. I was the only person with a computer on my desk. Everybody in the industry and my office, all my friends said, “Why do you need that? All you’re doing all day is sitting on that computer.”

What I was doing, what I did, and what turned out to be very successful is creating a data set of all potential buyers to the product that I was hocking and a way to contact all the potential sellers. I created a Coke bottle bottleneck between the sellers and the buyers. They had to go through me, crazy successful.

There’s a lot of time that it took to develop this thing. We could probably develop it in less than five minutes. Ultimately, I decided that those healthcare-type transactions for long-term care facilities were very difficult to complete. I applied that to rural vacant land. Here we are, a lot of decades later. The concepts were great. They still are great. It was what is now an archaic tool.

Workflow Transformation & Future Simplicity

This is all that is just changing again. One more point, this will change your workflow. What I described is the basic steps to get a property purchased and then resold for profit. Your workflow will entirely and completely change in the tools that you’re using to complete these tasks. It should become easier and easier.

I love that. It does. It has already.

My big picture philosophical question is, there’s a point where it’s going to become too easy.

Your workflow—and the tools you use to complete these tasks—will change entirely. It should become easier and easier. Share on X

It comes down to who can afford to do it. That’s fine. Who can handle it? Who can stomach it? Not everybody can write a check for $50,000 to buy property. That’s fine, too.

I’ll tell you something about Jill. Jill is an eternal optimist. I am not. She’s also fearless. “Whatever it is, I’m going to handle it. I don’t know when it happens. We’ll deal with it.” I love that about you.

Thank you.

Market Shifts, AI, & Real-World Answers From The Community

Let’s wrap up the episode with a few questions from our Land Academy community.

We have four questions. This is a lot. Question number one, Param asks, “Steven, aka Jack, with inventory levels rising 20% over 2025, I’m seeing my rural desert listings sit for 90 plus days. Is it time to lower my offer percentages on the next mailer or should I be looking at different asset classes entirely?”

I wouldn’t lower your percentages. You should always consider pricing your mailer and mailing out offers that are cheaper. Not more expensive always, so yes. Number two, you should always be looking for new asset classes, meaning info lots, large rural vacant acreage, possibly, ranches.

Non-desert, rural listing. Get out of the desert.

This is a business that I obsess on, obviously. I spent a lot of downtime. It’s not downtime. It’s just quiet time, researching all this stuff. The cream always rises to the top, especially with AI. You can ask it anything. Yes, do both of those things. I implore you to add houses wherever you are to your next mailer.

McKay wrote, “I’m hearing a lot about agentic AI, replacing VAs for lead intake and data scrubbing.”

We just talked about this.

“For a solo investor, is this something I can implement with tools like Gemini or is it still only for the big shops?”

That’s for you to decide after this. I asked some people that are in the tech industry, real old friends of ours. We were all laughing and having drinks and talking about the things that they asked AI to do then were pleased with. We also happened to be with another two people that are not in that industry in any way.

Their eyes were popping out of their head because they didn’t know it was possible. I hope there’s a lot of people reading this, that your eyes are popping out of your head because this stuff’s all here. It makes your life easier. I asked this question, “Give me a circumstance when you’re unsatisfied with the response that you got from any AI scenario.” Nobody can answer it. I include myself in that. Have you ever had one?

No, because if you didn’t give me the answer I wanted, I didn’t ask it right. I have to go back and go, “What did I miss?”

It’s just like marriage.

It’s like that. Is that the end? Question three, Jimmy wrote, “How are the new 2026 state privacy laws like those in Colorado and Oregon affecting how we buy and use our mailing lists? Are we going to see a squeeze on the data? Are we squeezed on the data providers like whoever’s out there?”

If a property owner’s top priority is maximizing price, they’re not your ideal seller. Most deals happen because of a recent life event—people simply want to sell quickly and without complications. Share on X

This is the latest tech attempt. Colorado, Oregon, and certainly parts of Northern California are very tech savvy, specifically Colorado. When they passed this really techie legislation, which apparently, I checked into it before we did this episode. Data can no longer be collected in these two states. That’s geolocation-oriented. Meaning, every time you turn on Google Earth and go down to the parcel level, which they stopped. Google Earth stopped that parcel level thing a long time ago, but you certainly can do it in Zillow.

This is their sophisticated way of stopping you from knowing about who owns what in this country, which has gone on this entire world. This country has always been special about open-source information, about who owns what and all the statistics on it. That opportunity is closing. This is the beginning of locking up data about who owns what.

Is AI going to change that for you? What I read, and this is key, is that you can’t sell the data. You can’t buy it. If you go on Google Earth, everything’s free. Once again, open-source rules. If you really think about open source philosophically, it’s just the greatest thing there ever was. All this stuff’s free. Of course, they’re keeping our data. They’re trying to sell us a Volvo or whatever we’re interested in looking at. I can deal with that. It just makes everything a limitless possibility.

Last question. Kirkland asks, “Jill, you always say the deal is one on the phone in a market where buyers finally have more leverage and less rush.” I don’t know about that. “How has your negotiation script changed to handle sellers who are still stuck on 2024 prices?” You know what Kirkland? They’re not real sellers.

My sellers, it’s not about the price. Something’s going on in their world. They need the dough. They lost their jobs. Kids going to college, inherited it, don’t want it. Nobody wants it. Tax bills show up. There’s all kinds of reasons that trigger people to pick up the phone and to call us. It’s not because they’re like, “I’m going to maximize the price. I can just feel it.” That’s not the reason. You will find that out too fast on the phone.

If they say, “I know you offered me whatever it is, but my sales price is $1 million.” We all know that’s not a real seller. They’re not in dire need. There’s nothing I can do. We’ll talk them into that. It’s not worth my time. It’s not worth it to me. I figured out they don’t need the money. This, to them, was just a fun exercise to see how their property is doing in the market. Whatever they think they’re trying to do, I don’t know. For me to just say, “Please save my letter well because someday you might be in need. We’ll talk then.” That does happen, and then answer the next call.

If you’re talking to a property owner whose number one concern is maximizing price, you can just stop talking to them. The reason that we buy and sell real estate, and we’ve done it almost 16,000 times, is because people had a recent life event. They just want to sell their property quickly without any complications.

I am so excited to announce this. I brought on another Land Academy coach. I have a handful of personally tested, been in our system, and trained. My arm material, our program, my version for coaching is out there. If you are thinking about doing this, and you want to do it right, you want to get in. That was the conversation we just had as I’m doing the last interview with this awesome gal who has been on a career path. Every year, she keeps doubling her money or more.

She’s like, “When I came into this, Jill, I wanted to do it. I went all in.” I said, “That’s great.” That’s what coaching is. You come into Land Academy and you’re all in. This is going to either fast track you or just help you navigate all the little steps along the way, because there’s a lot of them. We do have a self-study program if you just want to do that too. If you want to knock it out of the park, she said to me, “Time is money.” I said, “I get that.” Consider Land Academy coaching. Where do you find out more? Go to LandAcademy.com or send a note to Support@LandAcademy.com.

If you liked the episode, please drop us a comment. If you share a win or a question, we might use it next week. Join us next week where we discuss more interesting land topics. You are not alone in your real estate ambition.