Off-Script Friday: What’s It For

This is episode number 2238. We’re trying something new. We are going off-script with Jack and Jill. We’re calling it Off-Script Friday with Jack and Jill. If it catches on, we’ll continue to do it every Friday or every other Friday. This was a suggestion by our staff because they looked at our numbers very closely. They speak with our current members and would-be members. Our members have a lot to say about us horsing around with each other.

Was the conversation, “No one reads anyway, so just talk about what you want to talk about?”

It wasn’t even Friday. The whole Friday business was me. I said, “We wrap land. We put land in the middle of the crazy stuff that Jill and I do anyway. Why not talk about crazy stuff and see if real estate enters it? We’ll see.” 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.

Is this a Jack question?

Yes. What’s it like working with your spouse all those years?

I have to think about it. Is that for me? I thought it was for you.

I took out the topic. We’ll go straight into the Off-Script Friday.

We’re going to call this whole thing Off-Script. How long have we been working together? Is it sixteen roughly years? It is lovely and challenging.

All of our friends ask us, or ask me anyway.

It is weird.

The Dynamics & Longevity Of Working Together As A Couple

“You’ve been traveling around in an RV for the entire summer for the last four years?” Yes. “I could never do that with my husband or my wife.” I’ve been saying, “What do you mean? Why? Do you guys go out to dinner?” “Yes.” “Do you guys have fun?” “Everything is great. The kids are out of the house. We’re happy, but there’s no way I can live with my husband in an RV for six months in 300 square feet.” They can’t answer why, but we do it.

I know. I can’t answer why.

We work together. They don’t work together.

I know. I guess it’s just who we are. I feel very fortunate. For me, it didn’t get too old for us. I don’t think. There was a thing like we didn’t want to talk about work. There were times in the beginning when it was just too much. It was too much for us. It was too much for anybody around us. We were like, “Guys, knock it off.” It would be all we would talk about. It would just be consuming.

Land is also a hobby for us. We both love it. What do we do? We get in an RV and go look at the land. Just enjoy the land. If we go look at something, and we have a falling-down, uninhabitable mobile home in Idaho, we’re like, “This is the greatest thing ever.” We saw it. It’s sitting there waiting for us. I don’t know what we’re going to do with it. We can’t sell it because we love it. It’s great. What do you want to add?

I think that when you start something, whatever it is, if you’re starting it under duress, then it’s no fun. There’s going to be a lot of problems. Jill and I are going through two separate startups. It’s a blast. We have the right people in place. We have the right capital.

When you start something—whatever it is—under duress, it's no fun. Share on X

We’ve done it before.

We’ve done it successfully before. We know what not to do. We have the luxury of having worked with each other for fifteen years, so I know she’s good at it. I know where to stay out of the way. Jill came in right when my company needed to be entirely and completely turned around. This transition that we’re going through in real estate, where houses are probably better or need to be added to your land operation, needed to happen. We did it.

We found out pretty quickly that I’m not the best person to negotiate the deal. She is. She’s better on the phone. I’m better with the data. I can jam her pipeline full and on and on. When you’re going through those things and trying to figure out what that’s all about, it’s no fun. It’s so hard unless you need to do it. We did at the time. It was around 2009-ish. We needed to succeed at this, or we would have to go back to work.

I hadn’t had a real job at that point for ten-plus years. Nobody wanted that, so we made it work. That’s what it’s like. That’s why I can spend an entire summer in 400 square feet with Jill. It is because we’ve been through that. We’ve been to hell and back in situations. There’s a lot of history there. When people come to me and say, “There’s no way I can do that with my husband,” we get this all the time in Land Academy. Within Land Academy, we get people come to us saying, “We’re trying to work together, and we can’t do it.”

It is hard. There’s give and take on both. What we did early on, and even that was hard, was divide up the sheet. Dividing up the sheet and responsibilities was easy. Staying in your lane is hard. It’s very easy to trip over to the other person’s side. You have to go, “There’s a wall here.” I know it’s funny. We have years of consistent proof of knowing what each person is good at. I don’t have to prove to Jack anymore that “I got this. Please leave the room. Let me have the phone call kind of thing.”

It’s good because it went from land negotiations to pretty much everything, even primary residence. “I’m going to negotiate the deal.” With the sailboat, “I’m going to negotiate the deal.” I do it and then come to him when it’s done. Do you know what I still do? It’s so funny. Like the sailboat, “Tell me how you want this to go. What do you want the end result to be? I will do my best to make that happen,” or I’ll get as darn close as I can to that happening. That’s how we roll.

In the beginning, I’m a huge fan of sitting down with the calendar, setting up rules, and setting up procedures for everything. It is not just for that week, but the procedure for when a property comes in or whatever ends up happening between Jill and me. There are rules, a procedure, and a calendar event. We don’t have to do that anymore. It’s a huge luxury. We bought this boat. I don’t know when we closed on it. Both of us just kicked in to do with the stuff that we’re used to doing. I knew what she was going to handle. She knew what I was going to handle.

It was on autopilot.

Some of it crosses over a little bit, and it goes out of a lane a little. We both know what to do. That doesn’t happen overnight. It takes years. The thing about Jill and me is that we both wanted to accomplish the same thing. You can see it. As far out there as you look, you can see that success. We just went about it really differently. Jill is a social person. I’m not. I’m a technical, spreadsheet, data person. We both know that. I don’t ask her to do that, and she doesn’t ask me to do her stuff.

That’s what’s great, too. I don’t bug you.

I’ll tell you what changed with you in a great way. When something goes wrong, it’s very human to start blaming people. If you’re in a marriage or a business partnership, something goes wrong, and you’re blaming somebody, I don’t know why. Who knows why you’re doing that? It’s going to end fast.

Who cares? Fix it. That’s it. Move on. Who cares? It doesn’t matter how we got here. Here we are. How can we best get out of this jam together?

Why is that funny?

I don’t know.

You don’t like this.

No, I’m not good at this off-script thing.

You don’t like off script.

No, I don’t know what to talk about. We talk all day.

What do you want to talk about, Jill?

Optimistic Outlook For The 2025 Real Estate Market & Preparation Advice

I don’t have anything to talk about. How about this? I’m excited for 2025. I’m excited for the second half of 2025 because there’s some great stuff in Land Academy going on behind the scenes. I signed an NDA. I can’t talk about it, but I’m excited.

You signed your own NDA.

I did sign my own NDA.

We’re releasing some amazing products. Interest rates are going to go down here. Most of us are going to wake up, and the feds are going to reduce interest rates. It’s going to have a massive overnight, immediate impact in a positive way on what’s happened, the stagnation of real estate. I’m super excited about that, too.

I know because of the longevity, how long I’ve been into this, plus you doing this. Every time I’m bored, I think, “The sky is falling. It’s not going to happen.” Just stop it. Enjoy the boredom for a few minutes because with interest rates, something is going to happen. It’s all going to kick back up again. We’re going to be running around like crazy people. Give it a minute. Some of it’s summertime. So what?

Relax, enjoy it, be ready, fine-tune your business, and get better at something that you’ve been meaning to spend some time on. Maybe it’s trolling. Maybe it’s pricing. Maybe it’s answering the phones or fixing your website. I don’t know. Work on all that other stuff and be ready for when things start to go crazy and things kick back up. It will happen because it always does. You’re always going to wish you had ten more of whatever it was you sold.

That is great advice. Join us in the next episode for more land and house flipping investment contacts. You are not alone in your real estate ambition. We are Jack and Jill, information and inspiration to buy undervalued property.