The First 3 Questions To Ask A Land Seller On The Phone

The First 3 Questions To Ask A Land Seller On The Phone

Land Academy Show | Questions For Land Sellers

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The First 3 Questions To Ask A Land Seller On The Phone

Land Academy Show | Questions For Land Sellers

Never Miss an Episode!

Subscribe to the Land Academy podcast

This week, we’re diving deep into how to talk to sellers in 2025—because let’s face it, things have changed. There’s a perfect storm in real estate right now, and smart investors are adjusting fast. Today on The Land Academy Show, Steven Jack Butala and Jill DeWit break down the first three questions you should ask a land seller when they call—and trust us, these can make or break your deal. Forget wasting time on tire-kickers. With seller motivation higher than ever, it’s all about getting to the truth—why are they selling, what price do they really need, and how fast do they want to close? Plus, Jack and Jill check in with their Land Academy community where real partnerships are forming and deals are getting done. Tune in because in 2025, it’s not about doing more deals. It’s about doing the right ones.

Listen to the podcast here

The First 3 Questions To Ask A Land Seller On The Phone

This is episode number 2196. In this episode, Jill is going to talk about the first three questions to ask a land seller on the phone. All week, this week, Jill and I are talking about speaking with sellers in 2025. There’s a perfect storm of real estate and it’s great time. Don’t take my word for it. Go out on the internet and see what Grant Cardone is saying and see what everybody else is saying. We’re all saying the same thing because this isn’t our first rodeo.

On Monday, we talked about what the land and house seller profile looks in the mid to 2025. On Tuesday, we talked about how to target land sellers who are most likely to sell market value or below market value. Now, Jill’s going to talk about these three questions. Before that, each day on the show, we answer a question from our Land Academy Member Discord forum. Take a deep dive in land related topics by popular request.

Chip wrote, “Hello, Land Academy members. I have been an investor and a licensed broker in Florida for a long time. I have my own brokerage in Florida but for the past twelve years or so, I’ve been the broker of record for another investor in Florida in which he basically just pays me a flat couple hundred bucks per transaction and covers the cost of licensing to set up their brokerage here. For my land business, my primary niche is large tracks like 100 plus acres in Florida and Texas, then I resell them to a network of buyers that I’ve worked with for years.”

It sounds like a great setup.

“I’m looking for someone who’s a licensed broker in Texas that could be my broker of record in Texas so I can open a virtual office there, too. I run into situations where the numbers didn’t quite work out on a deal and I’ve had to refer it to another broker in Texas. I would just prefer to list properties that I didn’t purchase because they’re usually a of significant value. I can reach out to others but I like to work with someone just within our Land Academy community. Let me know if this completely hands off opportunity my work for you. Thanks in advance.” Super cool. Partnerships being made and informed and people helping each other in Land Academy.

There’s no question here. It’s just a typical exchange between Land Academy members. I’m trying to more accurately communicate what goes on in our Land Academy community to other light kind thinking people so that you can get on odd too. That’s what this is all about. Our topic, the first three questions to ask a land seller when you get them on the phone.

Why These 3 Questions Matter In 2025

Let me explain what’s happening. I’m changing the script not because it’s 2025, we do land deals different, or something I just felt like it. It was stale. I’m changing the script because of the times. It’s a unique situation that we’re in now. We talked about it. That’s the whole theme. It’s what’s going on in 2025, how do we pivot and get the right deals and make sure we’re not wasting time? This is what’s going on.

This this came to me because of the phone conversations I’m having. I didn’t even realize I was doing it. He just started doing it then I was coaching someone on a call and I went, “You need to stop and this needs to be your number one question.” I thought I need to be sharing this with everyone. You need to know this. People who are calling you now are calling you because they need the dough. Especially if you’re on Land Academy and you’ve been reading for a while, you know how we price things and how we pricing things even more aggressively.

You’re not sending things at retail. That’s not where this is going. It’s going down and not up, so our offers are going down too. It just makes sense because we’re buying for less and selling for less but we’re still making our same dough in the middle there. The people that are calling you back is not like, “The ship has arrived, baby. This is it.” No, they are calling you because they need you. Instead of wasting this time, too. I want you to cut to the chase because for me, especially with the volume that Jackson’s out. My phone volume can be busy especially, by the way, with the decades of mail that we have sent.

We are getting calls from 10-20 years ago. Not kidding. People put our letters in their file and then on a rainy day like now, they’re going into that file and calling and relieved that our phone number hasn’t changed and because of that, my volume is even higher than what Jack has mailed out. I’ve got old sell owners that were reached out to. It used to be like, “Let’s get the landscape.”

The 3 Questions To Ask A Seller

My call flow used to be, “Tell me about the property. Tell me about this. Tell me about that,” so I can get to know the area a little bit and get to know where they’re coming from. I did into the price and we make a deal. With a volume I’ve got and what’s going on, I don’t want anybody wasting any time. I’m talking about me and you as full-time land investors. Your number one question should be this, what’s going on? Why are you selling? Why are you selling the property now?

As full-time land investors, your number one question should be: What's going on? Why are you selling? Why are you selling the property now? Share on X

What’s an acceptable answer or an unacceptable answer?

An acceptable answer is my wife lost her job. My car broke down. My house cost just went up one third and I’m trying to keep food on the table. Those are all acceptable answers. An unacceptable answer is, It’s Tuesday. I’m bored. I don’t need the money. I need something to do. That’s why I’m trying to save you from because those still exist. You’re still going to get people that call you and they don’t need to sell. I don’t want you to spend even 5-10 minutes on the phone with him and find out they’re not a real seller.

I want you to identify that right away. Now, it sets the tone for how you’re going to move forward and how you’re going to work with these people. By asking them why they’re selling and what’s going on their life, they might answer question number two for you in that in question one. Question number two is, let’s talk about the money. I mailed you to this property for $13,682 or they’re going to tell you that they’re staring at the offer. They’re going to go, “Is this real? Will you pay me that?” That’s for question two. You’re going to talk about the money. Figure it out what’s going on.

Remember you mailed for $13,000 but they told you in question number one, they need $15,000 to pay off, fill in the blank, to survive. Now you already know where they’re coming from and you might be able to adjust that price. When you ask them and you’re talking about money, “I know you told me you need $15,000. I offered you $13,000. Do you have enough to cover the rest to take care of your car that broke down, or pay off the mortgage or pay off the college tuition for your kid?” Whatever it is. That’s question number two.

Question number three, again, it might come up in number one depending on how good you are but you need to have this in here. That’s why it’s an important in question number three, if you haven’t covered it yet. How fast do they need it? What is the timeliness here? What’s the speed that they need you to close? A lot of things will change in number two, which is price because you can do number three, which is fast. They might say, “If I can get $10,000 from you now, that’s going to tide me over and you said I can do it by the end of the month. I’ll take it, Jill. Let’s go.” I’ll make that happen.

The Evolution Of Seller Behavior & Property Pricing

Let me put this in perspective about what’s going on in 2025. When I started this in the ‘90s, we would send out offers for property for $500 in certain select markets. We’d like to buy your vacant property in the middle of nowhere for $500 because I’m sure you’re tired of paying the taxes. We just got flooded with signed offers back. No one was doing it before but what was going on, is there was no effective way for a regular person like you and me or Jill or any of us to go out on the internet and find out what the value of that asset was.

Five acres in the middle of New Mexico, $500 sounds pretty good to somebody who’s inherited it and they’re tired of paying taxes or for whatever reason. However, they own it or ended up owning it, they just don’t care. They don’t know what it’s worth. All they know is that they probably call a broker years ago and the broker said, “Your property is probably worth $2,000. I’m not going to list it because my commission’s too low. I wish you the best.”

They paid two more years of property taxes and they call me. They say, “I don’t care what it takes. $500 sounds great. What do I do next?” In that we won because we caught the data crest of the wave. We knew what it was worth and what we could sell it for. We had access to that information because I created a lot of it, a lot of data. That’s not the situation now. You can type in your address or look at your piece of property very quickly and easily on the internet, meaning the vast majority, if not all sellers know what their properties worth.

When they get a letter from me that says, “We like to buy your property for $13,000,” like Jill said and they’re aware of the fact that it’s probably worth $60,000 if they had six months to put it all together, get the real estate agent and go through all this other stuff. They’re aware of that or they don’t care to even look it up.

Those are the people that Jill buys property from. They do not care about what the prices. We just bought a house for $135,000 and I happen to be able to meet the seller, which almost never happens. He’s having a life of event and he’s like, “I wish you guys the best on this deal. I don’t care what happens.” Jill, the whole point of this topic is to get the answers to these three questions and then you’re going to decide whether or not you can move forward.

The people we buy property from should be those who don't care about the price. Share on X

Exactly, then you find out more once you’re on the same page within, you’re like, “Great. What do I do? I know why they’re selling. The price is great on how fast it is.” Now you’ve qualified this seller and that’s what you need to do. You guys are on the same page. You’re in the ballpark. They need the dough and now you go back. It’s much easier to buy the way. You go, “There’s someone I could sit down and do my due diligence. I’ll call you back Mr. Smith. Is the same time work for you?” You go down your regular path from there.

Ten years from now, it’s going to be something else.

It will change.

They’re all be based on data. It’ll be erased to the first people because we have amazing data on life events as they happen. I expect that some point AI will be telling us when divorce papers are signed, when people stop paying their water bill, or when the HOA is starting on a legal proceeding to collect past due HOA fees. The life of events, we’re not tracking that yet.

It sounds like maybe you are.

I am. Join us on the next episode where we discuss how long does it takes to flip a property in mid-2025? You are not alone in your real estate ambition. We’re Jack and Jill. Information and inspiration to buy undervalued property.

Important Links

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The Land Academy Show | Follow Up

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https://youtu.be/h4KVKfXebwM?list=PLExWT63zCvfuY0wFZtlIXbTQuQ_bdHVgQ Think a “no” means the deal is dead? Think again. In this episode of The Land Academy Show, Steven Jack Butala and Jill DeWit dive deep into one of the most overlooked — but incredibly powerful — tools in your land investing arsenal: follow-up.

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Each level comes with a preset amount of included data, Concierge Mail service, and postage. For example, the Green level includes 6,000 units of completed-for-you mail completely out the door at no extra cost to you.

All levels include a PatLive introduction and preset script (we will set up your phone answering for you), use of Land Academy’s personal Transaction Team to manage your deal flow, an AirTable (CRM) base setup managed by our (and your!) Transaction Coordinator, personal consulting, regular office hours, and includes your Land Academy subscription cost.

If you’re making this a business, Land Academy PRO takes the work off of your plate so you can focus on the things that matter – like running your business.

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$26,015

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Black

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Concierge Data+ (with data) Included mailers each month (data + concierge + mailer + postage). Our team will do your data for it and get it out the door.
6,000 mailers 9,000 mailers 12,000 mailers 15,000 mailers 18,000 mailers
PatLive introduction at no cost We will help you establish your first script and get PatLive set up on your behalf to answer your phones.
$500 value $500 value $500 value $500 value $500 value
Transaction Coordinator Use of our personal Transaction Coordinator team to manage your deals. Trained and ready to go!
$7,500 value $7,500 value $7,500 value $7,500 value $7,500 value
AirTable Ready-for-you CRM managed by your personal Land Academy Pro Transaction Coordinator
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Personal Consulting 1 on 1 personal consulting with our Transaction Coordinator each week.
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Regular Office Hours Regular office hours with Jack and Jill + our staff. Private for LA Pro Members Only. (Think Career Path Office Hours)
$2,500 value $2,500 value $2,500 value $2,500 value $2,500 value
ParcelFact ParcelFact is included in your LA Pro membership with unlimited pulls.
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Land Academy No more separate charges - Land Academy is included with LA Pro Membership. This includes all education, tools, support, and future releases.
$300 value $300 value $300 value $300 value $300 value
Subtotal: $8,550 value $8,550 value $9,550 value $12,050 value $12,050 value
Mail Value: $7,500 value $11,250 value $15,000 value $18,750 value $22,500 value
Total Value: $39,050 $42,800 $47,550 $53,800 $57,550
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Green

$10,060

per Month

Concierge Data+ (with data) Included mailers each month (data + concierge + mailer + postage). Our team will do your data for it and get it out the door.
6,000 mailers
PatLive introduction at no cost We will help you establish your first script and get PatLive set up on your behalf to answer your phones.
$500 value
Transaction Coordinator Use of our personal Transaction Coordinator team to manage your deals. Trained and ready to go!
$7,500 value
AirTable Ready-for-you CRM managed by your personal Land Academy Pro Transaction Coordinator
$100 value
Personal Consulting 1 on 1 personal consulting with our Transaction Coordinator each week.
-
Regular Office Hours Regular office hours with Jack and Jill + our staff. Private for LA Pro Members Only. (Think Career Path Office Hours)
$2,500 value
ParcelFact ParcelFact is included in your LA Pro membership with unlimited pulls.
$150 value
FREE Career Path Access
$23,000 value
Land Academy No more separate charges - Land Academy is included with LA Pro Membership. This includes all education, tools, support, and future releases.
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Subtotal: $8,550 value
Mail Value: $7,500 value
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Concierge Data+ (with data) Included mailers each month (data + concierge + mailer + postage). Our team will do your data for it and get it out the door.
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PatLive introduction at no cost We will help you establish your first script and get PatLive set up on your behalf to answer your phones.
$500 value
Transaction Coordinator Use of our personal Transaction Coordinator team to manage your deals. Trained and ready to go!
$7,500 value
AirTable Ready-for-you CRM managed by your personal Land Academy Pro Transaction Coordinator
$100 value
Personal Consulting 1 on 1 personal consulting with our Transaction Coordinator each week.
-
Regular Office Hours Regular office hours with Jack and Jill + our staff. Private for LA Pro Members Only. (Think Career Path Office Hours)
$2,500 value
ParcelFact ParcelFact is included in your LA Pro membership with unlimited pulls.
$150 value
FREE Career Path Access
$23,000 value
Land Academy No more separate charges - Land Academy is included with LA Pro Membership. This includes all education, tools, support, and future releases.
$300 value
Subtotal: $8,550 value
Mail Value: $11,250 value
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12,000 mailers
PatLive introduction at no cost We will help you establish your first script and get PatLive set up on your behalf to answer your phones.
$500 value
Transaction Coordinator Use of our personal Transaction Coordinator team to manage your deals. Trained and ready to go!
$7,500 value
AirTable Ready-for-you CRM managed by your personal Land Academy Pro Transaction Coordinator
$100 value
Personal Consulting 1 on 1 personal consulting with our Transaction Coordinator each week.
$1,000 value
Regular Office Hours Regular office hours with Jack and Jill + our staff. Private for LA Pro Members Only. (Think Career Path Office Hours)
$2,500 value
ParcelFact ParcelFact is included in your LA Pro membership with unlimited pulls.
$150 value
FREE Career Path Access
$23,000 value
Land Academy No more separate charges - Land Academy is included with LA Pro Membership. This includes all education, tools, support, and future releases.
$300 value
Subtotal: $9,550 value
Mail Value: $15,000 value
Total Value: $47,550
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Platinum

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Concierge Data+ (with data) Included mailers each month (data + concierge + mailer + postage). Our team will do your data for it and get it out the door.
15,000 mailers
PatLive introduction at no cost We will help you establish your first script and get PatLive set up on your behalf to answer your phones.
$500 value
Transaction Coordinator Use of our personal Transaction Coordinator team to manage your deals. Trained and ready to go!
$7,500 value
AirTable Ready-for-you CRM managed by your personal Land Academy Pro Transaction Coordinator
$100 value
Personal Consulting 1 on 1 personal consulting with our Transaction Coordinator each week.
$1,000 value
Regular Office Hours Regular office hours with Jack and Jill + our staff. Private for LA Pro Members Only. (Think Career Path Office Hours)
$2,500 value
ParcelFact ParcelFact is included in your LA Pro membership with unlimited pulls.
$150 value
FREE Career Path Access
$23,000 value
Land Academy No more separate charges - Land Academy is included with LA Pro Membership. This includes all education, tools, support, and future releases.
$300 value
Subtotal: $12,050 value
Mail Value: $18,750 value
Total Value: $53,800
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Concierge Data+ (with data) Included mailers each month (data + concierge + mailer + postage). Our team will do your data for it and get it out the door.
18,000 mailers
PatLive introduction at no cost We will help you establish your first script and get PatLive set up on your behalf to answer your phones.
$500 value
Transaction Coordinator Use of our personal Transaction Coordinator team to manage your deals. Trained and ready to go!
$7,500 value
AirTable Ready-for-you CRM managed by your personal Land Academy Pro Transaction Coordinator
$100 value
Personal Consulting 1 on 1 personal consulting with our Transaction Coordinator each week.
$1,000 value
Regular Office Hours Regular office hours with Jack and Jill + our staff. Private for LA Pro Members Only. (Think Career Path Office Hours)
$2,500 value
ParcelFact ParcelFact is included in your LA Pro membership with unlimited pulls.
$150 value
FREE Career Path Access
$23,000 value
Land Academy No more separate charges - Land Academy is included with LA Pro Membership. This includes all education, tools, support, and future releases.
$300 value
Subtotal: $12,050 value
Mail Value: $22,500 value
Total Value: $57,550
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