Working With Your Spouse: Lessons From Completing 16,000 Real Estate Deals

Working With Your Spouse: Lessons From Completing 16,000 Real Estate Deals

Land Academy Show | Working With Spouse

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Working With Your Spouse: Lessons From Completing 16,000 Real Estate Deals

Land Academy Show | Working With Spouse

Never Miss an Episode!

Subscribe to the Land Academy podcast

Today on The Land Academy Show, join Steven Jack Butala and Jill DeWit as they share what it’s really like working with your spouse while completing over 16,000 real estate deals. They talk candidly about what makes it work (and what nearly broke it), how they divide roles, and why mutual respect is more important than matching skill sets. Whether you’re considering going into business with your partner or already navigating that dynamic, this episode is packed with practical insight, personal stories, and real advice from two people who’ve done it successfully for years.

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Working With Your Spouse: Lessons From Completing 16,000 Real Estate Deals

Working With Your Spouse: Lessons From 16,000 Real Estate Deals

This is episode number 2248. Jill has a fun topic, fun for us. Anyway, we’re going to talk about why working with your spouse and the lessons that we’ve learned from completing 16,000 real estate deals.

I say more than that.

More than 16,000?

No. Something even harder to do than that, I’m going to say harder, is 2,000 episodes. That is way harder than 16,000 real estate deals.

Every once in a while, somebody sends me a note and says, “I’ve listened to all your shows,” and I say to myself, “If you add that up.”

I don’t think it’s possible anymore. They used to be in the beginning.

That’s 2,200 shows.

Yeah. I don’t think it’s possible because it’s years. It’s like, “I’ve listened to all your shows. I went into a hole for a year and a half.” Go ahead.

Working with your spouse is not easy. It takes a lot of rules. The thing is, just make sure it’s worth it. Make sure whatever you’re doing or trying to accomplish, buying a bunch of land, making a bunch of money, retiring it together, that it’s all going to be worth it because it’s tough.

I’ve got stuff to say because we covered this in the ladies call, so I can help with this topic in a minute.

Jack’s Land Academy Regrets: What He’d Change

Each day on the show, we answer a question from our Land Academy Member Discord Forum and take a deep dive into land-related topics by popular request.

This looks like a throwing me under the bus question.

Working with your spouse is not easy. It takes a lot of rules. Share on X

No. Why would I do that? I would never do that on the show. I wouldn’t do it on the show anyway.

You’re doing it right now. Let’s Jack read the question and then you decide if he’s throwing me under the bus here, because I think he is.

I think this is an open-ended objective question.

Let me ask you the question, then. Jack, if you could do Land Academy all over again, what would you keep, delete, change, or improve on?

From a content standpoint, there’s not much I would change because the concepts of this are the same. The tools that you use to buy and sell real estate change all the time. I would’ve worked a little bit harder from the beginning on creating tools that keep up with the times and Jill and I are making up for that.

Our own tools, yeah.

We’re creating a software. We call it a CRM Pizza Tracker around the office. We’re about 40% of the way finishing an easy button type that walks you all through the steps of the process and allows you to, in most cases, click on a button to help to ask us our staff to complete the task for you. Will you price our mailer? Yes. Will you close the escrow deal? Yes. The same stuff that we do for ourselves, but in a very organized way.

That’ll be released or at least we think we’re going to release it late summer, early fall. I think we’re going to release it in late summer. We’ll see. I would change that. One of my mantras or my leadership directives since we started Land Academy was that we’re not going to market them hard. If people want to find us, then they can find us. I would’ve changed that because it’s turned out to be a little bit harder on our staff and harder on Jill from a sales standpoint.

If we were better internet marketers, which were not, even to this day, it would’ve made it a lot easier. The reason we started Land Academy in the first place was to find people that we could be financial partners with that are like-minded. Back in the day, it was real hard. If you went and tried to get any type of money from anyone and you said you buy and sell land, they just laughed at you, laughed straight in your face. Land Academy was really effective in utilizing the internet to find people that were already doing well in land and were throwing money at us. The initial reason we started Land Academy that was crazy, super successful, I would not change that at all. I’ll keep that.

Jill’s Land Academy Journey & Community Rewards

My reason for starting Land Academy was because they begged us. That was the only reason for me.

To stop the questions.

No. Just like, “Okay, what are you doing?” We can’t answer one by one how we’re doing this because we were that open in sharing our model.

You could create the greatest new whatever part in your sink and someone's going to copy it out of wherever it's being made. Share on X

Learning curve is huge for Land Academy. We could have just gone on, I don’t know, I still go back and forth in my head. If we just would’ve bought and sold land the entire time, I don’t know where we’d be.

I have an idea. It’d be a lot less competition.

There’d be just a lot less everything. A lot less working. We probably spend 80% of our time on Land Academy and 20% buying and selling real estate. It would’ve been a little bit different. It, but the show’s about Jill and I and spouses. That’s the topic. We’re moving into that. I would not change anything when it comes to working with you.

Thank you. Same here. That’s very sweet of you.

How’s the thrown under the bus thing?

The question was a little bit like, I’m like, “If I do it all over again, what would I,” whatever.

If I were to throw her under the bus or throw myself under the bus, here’s the question.

Let’s go back. I thought of something too. You go first. Go ahead.

If you could do it all over again with me, would you do it?

I don’t have enough time for that one. No, of course I would. Me too. If I could do it like all over again, I would’ve replaced myself with a really good website designer faster. I would’ve skipped eating for a week so I could afford somebody else to fix websites. That’s something I would’ve done back in the day. Let’s see if I could do it all over again. We would’ve got it online quicker. Remember we had DVDs back then? That was a crack up. The whole program and how it all evolved, I wouldn’t change. Our online community and how that all evolved. I wouldn’t change. It’s really great. We have people with us for many years. The whole time in the ‘90s was so great.

There were two people, me being one of them, really doing this on any workable level. The other guy never went into this business at all. Everything that everyone teaches in every corner of the internet was some offshoot of Land Academy. My real disappointment is the willingness for people to just copy what we’ve done and then basically plagiarize it, copy it and then regurgitate it as their own. That’s really sad. That’s been the single biggest disappointment in all of this.

People do it all the time. You could create the greatest new whatever part in your sink and someone’s going to copy it out of wherever it’s being made.

Try to learn to work together and come at things in a healthy, constructive way. Share on X

Outside of that, here’s the positive. Here’s actually the truth of it all. It’s been crazy rewarding to watch people. This happens probably once a week, maybe once every two weeks. I get a note or Jill gets a note. Maybe we both do that says, “I just want to thank you guys. You changed our lives. We both got to quit our jobs.” There’s a long list of people. It makes you cry when you think about it. “We got to raise our children.”

“Be home with our kids.”

“We raised our kids. We picked them up from school and on and on.” I didn’t expect that, and I never anticipated anything like that. That’s a huge reward. Jill says once in a while, “I’m sure we’re going to heaven now. We’re helping some people,” to the point where we shouldn’t be doing it.

Working With Your Spouse: Key Pros And Cons

To wrap up that working with your spouse, I did a whole talk on that with the Land Academy Ladies Group and what we talked about was working with your spouse has pros and cons, obviously. One is trust. It’s not like I’m bringing an out unrelated third party as a business partner. The trust is there. Number two, hopefully, I know what their strengths and weaknesses are. Before we worked together, I knew you were a data nut. How did I know that? That’s because when we were first dating, you would send me love letters as an Excel attachment. You didn’t know anything but Excel. That’s how I knew that. It gave me a little indication of how you are and what you’re doing. That’s good. Working with your spouse.

The second part of working with your spouse that we’ve learned, and we always had, and I want to share, is to make sure your goals are the same. Be specific about some goals. How much do we want to make this year? How hard do we want to work? Who’s going to be in charge of the kids and the house? Divide up stuff like that. Have a lot of partner’s meetings. Try to limit things for partner’s meetings because if you’re having a partner’s meeting in bed in the morning and in bed at night, and then at the dinner table, not only going to drive your family and your friends nuts, but you’re going to drive yourself nuts. You need to have an escape. You have to try to keep it into that.

Try to learn to work together and come at things in a healthy, constructive way. Not like, “Put down the phone, you suck at it. You just screwed up my deal,” kind of thing. That can happen. Speaking from experience. I didn’t say it like that, I’m sure. I might have said that actually. I’m sorry now. I’m telling you I’m sorry.

A lot of years ago. Enough though. She remembers.

I do remember that. The dividing up the role responsibilities and stay out of each other’s lanes. There are things you want to do, things you like to do, things you’re good at, things you suck at and things you hate. You’ve got to mix it up a little bit. We did a good job of, “All right, I’ll do these two things if you do that one because it’s easier for you and I just despise it.” “Okay, fine, because you’re taking those, I’ll do this.” There’s a good way that you can divide up the stuff. That makes it a little more fair, especially when you’re starting out.

A, you need to have control of it all and learn it all. B, you don’t have the money to outsource this stuff. That’s what you got to do. Moving forward into the groove. You just further own your roles and let the person run with them and trust their decisions. Even if you don’t agree with them, that’s okay. Let them run. They’re ahead of that department. That’s their thing. Stay out of it.

The last thing you need to do is get involved because now you’ve got two of you doing the work and you’re going to piss them off. It doesn’t make any sense. Coming to the end of it where you have your groove and everything, celebrate together. Have at least monthly partner’s meetings. If you get from weekly to biweekly, then to monthly, partner’s meetings should be good and fun where you’re looking at the numbers.

Are we on track this month? Are we on track this year? It’s probably going to be more than monthly meetings, but have those and celebrate and make sure everybody’s getting what they want out of it. “I really want this. I think I’ve earned it.” The other person is going to go, “Yeah, you have. Yeah, you do. Knock yourself out. Instead of one spa day, you want a spa week? Whatever it is. How can I help?”

Essential Rules For A Successful Business Partnership With Your Spouse

Here are a few key points to working with your spouse that you need to ask yourself before you make that decision together or if you’re already in it, I want you to do both to sit and think, “I wonder if what this guy’s talking about pertains to us.” Number one, do you want to go to the same place when you’re all done and it’s 8 years or 10 years from now, or 20 years from now? Do you have that same goal together? Do you want to go to the same place?

Separate everything and trust that the other person's going to do it better than you can. Share on X

I got in a lot of trouble personally and professionally in relationships prior to Jill because I assumed everybody wanted to become wealthy and do well and enjoy life. All the times, professionally and socially, that just wasn’t the case at all. If you’re in a situation like that, you’ve got to get out of it because you’re reading this because you’re an entrepreneur. You want to go someplace. If the people in your life don’t, they don’t.

Number two, it’s a version of what Jill said, but a way scaled, more simple version. You have to keep a calendar. When the other person’s saying, “You really screwed this all up,” you can say this. “We have a meeting about it at 3:00 and we’re going to talk about that and the ten other things that are in there, and I understand your point. Let’s talk about it then.” Otherwise, the entire day is just emotional reactions and terrible crap. You have to have a calendar and stick to it. This business of having a business meeting at 8:00 in the morning when everybody’s rolling out of bed, that happens. It wrecks stuff really fast.

People right now are going, “You roll out of bed at 8:00 in the morning?” It’s actually earlier than that.

It’s 4:30 now. When we started this, it was 8:00, now it’s 4:00 and all this gray hair, I didn’t have any of that. I lost my thought. When you get older, you have to laugh at the other person who loses their thought.

It’s okay. Cover for each other. That’s it. That’s the last thought. That’s the last point.

It’s just that I forgot. It’s just awful.

The Toughest Yet Most Rewarding Journey

It’s okay. This has been an awesome journey. It’s interesting because you have to go into this expecting it’s going to be hard. It’s one thing to have a roommate, figure out a roommate, and then you have kids and then you throw a business in there. This is probably the hardest thing that we’ve ever done, but also the most rewarding.

I remember it. Separate everything. There’s no chance on this planet that I would get done with doing all the financial stuff that does goes on and prep it all for the accountant to do our tax return. Jill’s questioned that. There’s no chance that she would review it or take a look at it. Some people are such control freaks that they have to control everything. That’s never going to work.

I do the financial stuff. She does all the negotiation. It’s the same thing with me. “Really? You only got that piece of property for $16,000? I think it’s only worth $10,000.” I would never question Jill like that. In the beginning, we looked at stuff together, but now, that’s her lane. Separate everything and trust that the other person’s going to do it better than you can. That’s it. Join us next time in your real estate ambition.

Sorry. I was going to do the other topic thing here. Do join us next time.

We’re doing exactly what we told everyone not to do. Trust the person who wrote the scripts, can execute it at the end, even though the whole thing got a little discombobulated. We are Jack and Jill. Information and inspiration to buy undervalued property.

Important Links

Land Academy Show | Land-Buying Script

Jill’s Updated Land-Buying Script For 2025 – Why Are You Selling?

https://youtu.be/vPeOrmhUszE?list=PLExWT63zCvfuY0wFZtlIXbTQuQ_bdHVgQ Today on The Land Academy Show, join Steven Jack Butala and Jill DeWit as Jill shares her updated land-buying script for 2025 and the one powerful question that drives every great deal: “Why are you selling?” They walk through the psychology behind that question,

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Land Academy Show | Negotiate Land

Why We Don’t Negotiate Land And House Deals

https://www.youtube.com/watch?v=JDl55C1rWtE&list=PLExWT63zCvfuY0wFZtlIXbTQuQ_bdHVgQ Today on The Land Academy Show, Steven Jack Butala and Jill DeWit explain why they do not negotiate land or house deals, as well as why this approach actually leads to faster, cleaner closings. They share how setting the price upfront filters out the

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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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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.
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Transaction Coordinator Use of our personal Transaction Coordinator team to manage your deals. Trained and ready to go!
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ParcelFact ParcelFact is included in your LA Pro membership with unlimited pulls.
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$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
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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.
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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.
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Subtotal: $8,550 value
Mail Value: $11,250 value
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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.
$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
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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)
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ParcelFact ParcelFact is included in your LA Pro membership with unlimited pulls.
$150 value
FREE Career Path Access
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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
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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.
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