This is episode number 2227. In this episode, Jill and I are talking about Mailing Smarter, Thinking Bigger: The 2025 Investor Reset You Didn’t Know You Needed. I didn’t come up with that title, but I like it.

The Current Market “Dip” & Opportunity

Thank you. I did, but I had help. That’s good. Mailing smarter, thinking bigger. I think a lot of people are looking for a reset. They’re not sure what to do. I see it a lot on social media, and I’m hearing it in our community, and it’s been going on. There are always ebbs and flows in every business. Sometimes when there’s a dip, people are like, “It’s over. The sky is falling.” No, it’s not. I promise.

We’ve been through it before, and you brought it up beautifully on our member call. Jack said some version of, “You think this is bad. You should have been around in ’08, ‘09 and ‘10. That sucked,” but we got through it and we did it. We pivoted and made a bunch of changes. That’s what we’re doing right now. I almost think this is a baby dip. This is a baby hiccup. This is a hiccup. This isn’t a dip.

You guys know how to adjust this. You’re learning it all right now. Who knows? Ten years from now, when there’s something major, you’re going to be like, “I got this.” I made a point with this, but think about investors. Think about stock markets and things like that. Everyone knows when there are changes and upset, and people aren’t clear. They don’t know what’s happening. That’s when fortunes are made.

Buy low, sell high is the middle name of the business we’re in. Right now, it’s much easier than it has been in the past to buy property inexpensively. It’s way harder to resell it.

Unless it’s low.

If it’s super low and you want to resell it now, you’re still not going to get what you would get five years from now. I’m not advocating that. I’m just saying that’s what it is. Some people buy a stock, and this is a great example, and resell it the next day or the same day. Day traders. Some people have a long-haul view. I have a ton of friends, because of my age, who have $1 million worth of Apple stock because they bought an Apple computer 15 or 20 years ago, because they liked the product. They bought the stock, and now they have tons of money.

There are a lot of different ways to do this. However, what the point of this is, however you’ve been doing it, and it’s probably changed, you’re probably not happy about it, make some changes. This episode is all about thinking bigger. This entire week is about markets, mailers, and a mindset. These are things that you have to rethink in 2025. We’ll enjoy this. Whatever you’re rethinking, you’ll enjoy it for a while until it changes again. Each day on the show, we answer a question from our Land Academy Member Discord Forum. We’ll take a deep dive into land-related topics by popular request.

Kelly wrote, “Can anyone answer what percentage of deals that come through your mailers meet all of the requirements for the money borrowing? Do they come as a lower percentage or in waves or fairly consistently?” I see what you’re saying. To get a funder. Is that how you read that?

Do you want me to answer?

Hold on a moment. Not yet. I didn’t ask that question.

I’d choose the titles and the questions. I know the whole thing, so I know what’s happening before we start. All you see, all day, every day, with Jill is getting blindsided.

That’s exactly right. Thank you for that. That’s so true, like, “Jill, are you not prepared?” No. I wing it, so I have to read it again. She’s just saying, “I want every deal to be perfect, so someone else is going to fund it. How is it going to happen?” I don’t think there’s any rhyme or reason to it. What do you think?

I saw an interview with Barry Manilow one time. This is a long time ago. The guy asked this question. “There must be songs that everybody wants to hear at every concert that you play that you feel like you’re probably going to vomit if you have to sing that song even one more time.” He reeled them off, starting with Mandy. As a listener, I feel like vomiting when I hear Mandy. This question, which is an offshoot of how many mailers does it take to get a deal, that’s this question. That’s how I feel.

This is like how many licks does it take to get to the center of a Tootsie Roll Pop?

This is my Mandy. I don’t know. It depends on you, Kelly. It depends on your business partner. If you’re great at pricing, if you can answer the phone in some version of how Jill does it. There’s a little bit of luck whether you’re mailing Alaska, Hawaii, or Michigan. I don’t know.

There’s no rhyme or reason to it because you might have ten going, “Holy moly, what just happened?” That could happen. I’ve had that. I’ve had signed things come back. I’m like, “Holy cow. What just happened? We’re buying them all.”

I probably have 50 examples of us sending mail out and having somebody call us and say, whether it’s the heir or the actual 90-year-old man who’s been collecting land his entire life, saying, “You know what? I liked you guys. I saw you on the internet, and I’m going to sell all my property before I die so my kids don’t have to deal with it. Why don’t you give me an offer, and we’ll put something together?” On a 2,000-unit mailer, I bought 48 properties from Old Man X. You can’t do the math on that.

Remember the guy who called because his dad had passed on and bought many properties from you? He’s like, “My dad loved you. He bought these properties from you. I have no use for them now. Can I sell them back to you? Let’s work out a deal.” That was lovely.

I’m not picking on you at all, but if a new fisherman came to an old fisherman and said, “How many times do I have to drop my line in the water before I catch a fish?” The old fisherman might say, “Are you ocean fishing or lake fishing? Are you on a boat or a dock? Are you 20 miles out, or did you wade out? Are you fly fishing? Are you saltwater fishing? Are you using lures or live bait?” On and on. That’s how I answer this question.

It comes back to, “Did you do everything perfectly like the fishermen did yesterday, and they’re just not biting today?” That could happen.

You have to, to some extent, enjoy the process of all this to reap the reward. If you do a 2,000-unit mailer, and you just want to know when you’re going to get your $1,000 back and when you’re going to get your Ferrari, this is not the business model for you.

Buy low, sell high is the middle name of the business we're in. Share on X

Enjoy the process.

Nothing personal, Kelly. I’m glad you asked the question, I truly did, but if this is not more for you, it’s more for everybody else. There is no way to quantify this, even though we’re going to answer it next week.

Do you still enjoy the process?

We just talked about this. There are certain parts of all of this, just like probably Barry Manilow, that I enjoy. There are some parts that I don’t enjoy. However, we’ve been doing this long enough and have made enough money that we can now have people do the parts we don’t like. I hope you feel that way. Do you?

I do.

Is there anything you don’t like to do? What’s your Mandy?

I was hoping you would ask. My Mandy at work is please don’t think I’m your tech support.

Is it like, “My mouse doesn’t work,” or “The website is down?”

I have to do that sometimes. People look at me like, whether or not I know, you shouldn’t be asking me. It is not Tech Support Jill. That’s not my name.

I’m going to want you to answer the next question, but I saw an interview a million years ago with Bill Gates. He said, “I just got off the phone with somebody who is not enjoying their experience with Windows 3.1. Do you think I should be doing that?”

At home, I hate anything surrounding meals and food. Meals and food are my Mandy. It’s like, “Here we go again. Another meal.”

You mean making it, not eating it?

I like eating it. It depends on what it is, though. I’m a foodie.

I’m not. I ate beans out of a can.

You go to the garage and have sardines sometimes.

Yes, because Jill can’t stand the smell.

Thank you. I appreciate that.

This is what she said to me recently. “You know how you like the garage. You go out there and eat food and stuff and have a beer? That’s not normal. I like to go outside in the backyard.”

Mine is the backyard.

Look at bunnies and stuff.

I do, and he just sits in the garage. Granted, it’s a pretty garage with stackers.

Our garage is my favorite room in the house. What are we talking about? Our topic is called Mail Smarter, Think Bigger: 2025 Investor Reset You Didn’t Know You Needed. That’s how we got on this. You don’t know what you’d need, Jill.

I don’t know what I need? Is that what you just said?

I’m joking. She’s been married for a long time. Your wife has said these things to you. “You don’t know what you want. I know what you want.” This happens.

Mailing smarter means digging a little deeper in the data. The data always tells you what to do. Share on X

Yeah, I’ve heard that. “This is what I think you need today.”

The Importance Of “Thinking Bigger” With Deal Size

The topic is, I want you to think bigger. We’ve covered this all week. You’ve got to send out more mail. You have to rethink your markets and microscopically look at them based on your past performance there, based on what the market indicators are selling you. There are way more houses selling over here at this price than there are over here. Let’s focus on this little mini market.

To justify this extra work and extra expense, you need to buy and resell larger properties dollar-wise, not size-wise. There is all the research that’s associated with it. Jill has been calling it, for as long as I can remember, adding a zero. If you’re buying properties for $2,000 and selling them for $5,000, I want you to consider buying them for $20,000 and selling them for $50,000.

Can I talk about that for just a few minutes? That was fun when that topic came up. There were a lot of people who were like, “You get comfortable, you get in your zone. I can buy for $2,000 and sell for $5,000. I can do it again and again.” I’m like, “This is great. Now, do you want to do $20,000 of those this month? Let’s think about this. What if you do the same amount of work?” “Jill, you got my attention.” “You just add a zero. Instead of doing ten more deals, you do the same number of deals, but with a zero.” “What?” “Yeah. You’re buying for $20,000, selling for $50,000.” “Does that work?” “Yes.”

It’s scary at first. I remember this was a couple of years ago. I remember there was a group of them doing it together at the same time, making that transition. When they did, I said, “By the way, it’s even easier.” “What are you talking about?” This is true. “Those buyers who are coming to you to buy a $5,000 property are very different than the buyers for $50,000 properties.” “What?” “Yes.”

It just makes sense. The $5,000 buyers are the ones who have a lot of questions. They need to budget the taxes. Even though it’s $70 a month, they have to budget that. They’re scraping together the $5,000 and having a big yard sale or who knows what because that’s all that they have to afford this property, versus the $50,000 person. They’re ready for it. They’re professional. They don’t have those questions.

Let me run this by you. Think about the $500,000 buyers. It’s even easier. They are professional. The only call they’re calling to ask is, “Before I move this money around and move it out of this account into this account so I can wire you and close this deal, is it still available? Can you answer this one question?” That’s it. It’s so much easier and way more fun.

Let me paint a picture for you, Jill. I completely agree. You send out a house mailer in a hot market. It’s hot, meaning it passes the Red, Green, Yellow test with flying colors. Every property that gets listed under a certain amount under the break point in the market gets sold within a week. Every single one, regardless of quality. It’s the logical stuff. Three bed, more than one bathroom. It’s on a rational sized lot. The data will tell you.

The data tells you that the breakpoint in the market is $400,000. Everything below that sells quickly. The further you get away north of $400,000, the longer it takes. If you get past $500,000, all bets are off. We’re not sure. Now you know, in a micro market, like we were talking about in the last episode, that if you buy a house, what the statistics Jill just said, 1,800 square feet or more, and you list it for more than $400,000, you know exactly what’s going to happen. You will sell that property within a week. Your job in life becomes to buy properties there for $300,000 or $320,000 or maybe, if you’re crazy, $340,000. They’re out there.

It happens so fast, and it’s predictable.

They’re in your data sets on your desktop. They’re in there. They need to be contacted, reached by mail, and they need to be talked to by you in a manner that Jill communicates with sellers. Now you’re making $80,000 or $40,000 or $60,000 or whatever you decide. Does that sound easy? It’s very realistic.

Totally. Very.

Now, you’re taking all the guesswork. You have a crystal ball, and you know it’s going to happen if you do that.

Mailing Smarter & The New Volume Requirement

That’s the key. I have just two little points to make to wrap it up for me, which is that mailing smarter means digging a little deeper into the data. The data always tells you what to do. The data always tells you what people are buying. The data always tells you where to send mail and what size and what attributes that fly off the shelf, whether it’s a house or just land. It’s in there.

Number two is because it’s 2025, you’ve got to think bigger. Think bigger with numbers. Remember, you’re thinking bigger with these sale prices because you’re going bigger with your mail prices. That’s the end goal. Jack, we’ve talked about a lot this week. The volume he used to get with a real little amount of mail is very different now. You need to make the prices count to justify sending out that volume of mail. I still talk to people right now, halfway through 2025, who are sending out 1,000 units to one area to test it. A thousand is not going to do it.

You’ll be disappointed.

You’re not going to get the volume

First of all, I wouldn’t even call it a test. It’s not a test.

It’s sprinkling feelers.

You’re dropping your line in the water one time with a vacant hook on it, no bait, and expecting to have a career in fishing based on that one shot.

You need to do 3,000 to 5,000. That’s a test.

Maybe multiple markets.

Multiple markets of 3,000 to 5,000. Don’t say 5,000 and go one by one. If you’re new and you’re starting out like, “I don’t have the dough,” you’re going to build up to it. Save up until you have enough to do a good mailer. Don’t waste anybody’s time like yours. Have 3,000 to 5,000 units going out, and then it’s going to grow and build and get into a system.

“Jack, I’m not putting up any money up front. I’m starting a business. I’m not going to put up any money up front. I want to get money back.” Think about that. That’s not how it works. Join us next time, where we discuss the mindset shift of 2025, and why the old ways of land investing won’t work anymore. We’ve been talking about that all week. We’re going to recap it. You are not alone in your real estate ambition. We are Jack and Jill. Information and inspiration to buy undervalued property.