Defining Business Freedom

Jill and I are talking about how to build a land business that gives you freedom. I love this topic. Here’s why. You’ve all heard of people buying companies, little ones and then they bought themselves a job for the rest of their lives. The whole point here is to get complete control of your time and, hopefully, a bunch of dough to go with it.

I took freedom a little bit differently.

How else could you define freedom?

There are other ways to define freedom. Not only financially and time wise, but I thought about just being anywhere you want and creating your own schedule thing. We’ll get to that. I have more than three things. I have notes I will happily share.

How do you like not being in the middle of the Pacific Ocean, Jill?

It’s a little weird. For months, we spent most of it floating and now, we’re back at our base.

I had to ask because that’s freedom.

It is and we’ll get to that in just a moment. If you’ve ever done a live aboard situation, you know what I’m talking about. In the beginning, you feel like everything’s moving. In the grocery store, it’s not moving but you think it’s moving.

Jill and I bought a sailboat months ago. We got it all provisioned out, so we’ve been using it.

Now, we’re on land and I don’t feel like I’m moving. I’m okay with it. I finally got my land legs. You have to get your land legs back.

Thanks to Starlink. We didn’t miss a beat.

We’ll talk about that.

The Land Academy Model As A Working Example

Let’s get into it now then. How to build a land business that gives you freedom?

I have three main points and then I’ll tell you my points, then I’m going to go into detail on all of them. Number one, we did that. You have two working examples that did it and like we talked about with the boat. We’ll share a little bit more about what got us here and how long we’ve been doing it. Number two, I’m going to talk about goals if you want to do that. Whatever it is. You have to have goals. Number three, you have to create a plan to achieve those goals.

It’s one thing to have goals, but you need to have a plan to show, “If I do this, this and this.” Pretty much time wise, that’s a lot of it then you can do that. Let’s talk a little bit more about number one, having a land business that gives you freedom. When I say we did that, that’s us whether we’re here or floating or driving around the country in an RV or traveling to another part of the world. We’ve done all these things in the 30-something years that you’ve been full-time at this and the over 16 years I’ve been doing it with you. We have proven that.

Having goals is one thing, but you need a plan to map out, ‘If I do this and that, time-wise that’s most of it.’ Then you can make it happen. Share on X

We have been in other countries, logged in. We’ve been in Paris. That was how many years? Over ten years ago, I distinctly remember logging in from Paris, looking at our listings posted by our staff being just as mad as if I was at home in the office because they still looked poopy and reporting back to them, “Please update these photos. Please fix this. Move that” Whatever. I’m joking about being mad, but I could do it all.

We could sell things just like we did. Freedom, for you and I, or at least for me. I’m going to say, I was not tied to an office. That was huge for me. It goes into the plan part of it and I’ll cover it more. Being able to work from anywhere, whether it’s a boat or an RV or another country or another state, is because you helped set us up to be able to do deals. We picked the deals. You started us out with that, which is our goal is to do deals that are not around the corner that don’t require attention. I don’t have to show up and let anybody in. I don’t have to oversee a contractor. That, to me, has been freedom.

The Challenge Of Self-Discipline & Willpower

Step one in all this is to ask yourself very sincerely if this is what you want. We’ve all met people who think they want it. They start down that path and they get it. The fact is, they don’t want that. They can’t manage effectively controlling their own time. They need to go to work to be productive.

Some people do that. That’s true.

Most people are like that. They just don’t think that. They don’t know until they’re in a situation where it’s like, “Here’s a blank slate. This is your calendar. For the next four months, you’re going to learn how to buy and sell land.” That four month period is over and you’ve designed this. You’ve designed when you’re going to work on certain segments of building out your career.

At the end of the four month period, you’re going to have a mailer in the mail and getting ready to take phone calls on people that want to sell their land or don’t want to sell it and create real estate deals for yourself. In the course of that, creating some serious equity. Everybody says, “That’s what I want.” When you sit down and stare at that blank calendar and then you get up the first few mornings. You got complete and total control over your time as if every day were Saturday. It’s a different story.

They don’t have the self-control or the discipline.

We’re sheer well like this is my spot. I’ve known this about myself since I started working cutting lawns at 13 or 14 years old. I wanted to control my time. I had a job at a restaurant at the time. I’m just using myself as an example. I couldn’t stand it. It was a good job. For my age, I was making a ton of money. I love the people I was working with, even my boss. I still didn’t want to go back there.

We have a kid that says they control their time but they suck at it and they can’t do anything with that. If they have a shift, they have to be there at this time and then they’re done at this time, and someone’s telling them what to do the whole time. They are awesome at it.

You’re describing probably 90% of the people in the world.

They say they want it, but they don’t know how to do it. They don’t have the energy to do it.

If you ask them, they probably would say, “I don’t know where to start.” This is where to start, a show like this. The place to start is right in the mirror. I don’t know, Jill. You got a hardcore corporate job.

I hated it. I had a time card. Back in the day that was like a punch. It was awful. I remember I had a job and if you were late more than three times and you’re fired. Don’t talk about it. It was not flexible at all.

I would have to test it the first week.

You would have fired me so fast. Here’s what happened when Jill started working with Jack. Jill’s like, “Happy?” He’s like, “What are you doing? We have this to do and this to do.” “I’ll get to it. Give me some time,” and you’re like, “No.”

I like this but the truth is you’re going to be working 10-12 hour days until your pipeline is full. Your bank balance is on its way to being where you want it to be. It’s a lot more work but I wouldn’t trade it for anything even now. If I had to go back and start all over again, I would do the same thing. I just get back in 10-12 hours a day, rebuild a system, hire some people, raise some capital and get right back into it.

I feel like there’s a business owner learning curve, and I felt that too. I don’t remember how at what point I felt it. I’m going to say maybe a year or so in. It took a little time. After the in, you’re like, “I got in.” Now I understand what you’re saying better because I had that business owner say, “I got this.” A wave of comfort came over me. I was never afraid of employees and stuff like that but I know a lot of people that are deathly afraid of being a business owner.

They’re afraid of taxes, liabilities, and even just having an employee whose livelihood is dependent upon them. That is crippling to them. I never had that. I always figure that we’re going to figure this out. Our whole team, if this doesn’t work, we’ll come up with another plan. Don’t you worry. We’re all going to move over here and do this.

The Business Owner Learning Curve & Confidence

That’s it. Along those lines, Jill and I bought a 50-foot sailboat. It’s very large. I have a little bit of experience sailing. I grew up sailing around in Michigan, and Jill has none. We bought a sailboat that’s way out of our comfort zone. The reason it works is because the second we leave the dock, we don’t know what’s going to happen. You just start dealing with it. No matter what it is, you start dealing with it. Unfortunately, for us, we haven’t had any real tragedy happen, but a lot of little things have happened and you have to deal with them.

Little by little, spoonful by spoonful, establish some confidence in yourself that you’re going to know how to deal with stuff as it comes up. That’s exactly what being an entrepreneur or a startup person requires. Some confidence in yourself. How do you get confidence if you came off of a W-2 job or got out of the military or got out of a bad relationship? It just didn’t work for you. You have to just have some faith in yourself.

A lot of little things happen that you have to deal with. Little by little—spoonful by spoonful—you build confidence in yourself, knowing you’ll be able to handle things as they come up. Share on X

This is super key. You need to allow yourself and cut yourself some slack when you screw a bunch of stuff up. If you’re going to hold yourself to the standard that you’re supposed to do it right the first time. You’re going to be a very sad and disappointed person your entire life. I smash that boat into our dock on a regular basis. I don’t mean smash-smash, but I mean bang around the dock like it’s a pinball situation, probably 30% of the time that we go in. Do I like it? No.

If I don’t do that, I will never learn the right way. You only can watch so many videos and talk to so many captains before we have to go out there and screw it up. Being an entrepreneur is if you have to have that mentality until you have some confidence until you’re parking the boat right or docking the boat correctly. What helps me is to not concentrate on, “Maybe I’m going to screw this up.” Concentrate on what it looks like. A hundred times, I’ve docked the boat and 99 of them went way that I felt like I had some control.

Where are you now?

I’m probably 40% confident in docking that boat when there’s weather. When there’s no weather, I’m 98% confident. There’s always weather. There’s always something. There’s always going to be something and you’re always going to be disappointed if you expect to handle that perfectly or even well. You have to laugh at yourself a lot through this whole entire process but it helps me.

You laugh, I cry.

There’s a different thing that goes on with Jill, but she’s still in the same place, too. What helps me and it would help you, reader, is to focus on the freedom part of this. The episode is called how to build on the land business that gives you freedom. Put the structure together for yourself. We teach all this stuff in Land Academy.

Put the structure together and follow the program. As you’re going through it, don’t get upset about how it’s being taught to the details or any of that. Focus on the freedom part. After a couple of years of applying yourself, doing a bunch of deals, and taking things as they come, focus on what’s going to happen after that. Where you got X or whatever your budgeted numbers are, $10,000, or $20,000 or $30,000 or more or in some cases, a lot more, coming in a month where you can enjoy that freedom.

Goal Setting & The Plan to Achieve Them

You’re talking about financial freedom and I understand that. For me, it’s freedom like life, freedom like being my own boss. I can do whatever I want whenever I want within reason. You have us as examples and not you have us as examples because we’ve done it. We’ve done it, but you have hundreds of other people in Land Academy every day that are doing it, too. There’s going to be something within Land Academy.

You’re going to find someone to align with. For sure there’s enough people in here that you’re going to go, “Jack and Jill, I got it. You guys are a little weird but I learned a lot from you. Now, I’m going to partner but this person because I like the way they do deals. They have done this and taken it over here.” It’s great. My number two thing is setting goals. There’s financial goals and then there’s, maybe I want to pay off my whatever goals. It’s still financial.

A lot of it is just financial, that’s true. When you hit these financial goals that afford you to do, fill in the blank. “My wife can quit her job. My husband could quit his job. We can retire early. We can do such and such.” Whatever it is to you. When you sat down into the regular green test, not the red, yellow, green test. The equity planner. Within Land Academy, we have what’s called an equity planner that Jack created years ago.

When you reach those financial goals, you can do whatever matters most—maybe your spouse can quit their job, you can retire early, or pursue something new—whatever that looks like for you. Share on X

We share it with everybody in our group and it’s sitting down and doing these goals. It’s not just annual, monthly, weekly, or quarterly. It’s like, how much money do you want to make? This is something that we do in our real high level Mastermind to career path. Let’s talk about how much you want to make in your lifetime or have in the bank and you’re going to mic drop it thing, then you work it backwards. For me, I guess because I have you. Do you think that’s why?

I don’t put a lot of pressure on myself personally for specific financial goals because you do that. You set good, healthy and aggressive. I got a win. I’m a little bit competitive. I got to win things, but here’s what you do. You set these goals for us as a unit, as a unified front to which I’m like, “I’m going to make his goal and then some.” That’s always been my mindset. Did you know that?

You said that to me in the past a few times.

I love that. I’m going to finish my last point here on this and hand the mic over to you again. Which is to set the goals, you got to create a plan to achieve them, to achieve those goals. For me, when we first got together, you said, “I want to have a life and a career or whatever we do that we can do from the back of a boat. I want to be able to do this from anywhere.” I said okay. That was it. By your design, I know this. As I alluded to earlier, we set out to do deals that met those goals. For example, land deals from other states.

It doesn’t matter if I’m in Arizona or in Texas. I might be buying land in Tennessee. Whatever. It works out great. The other thing is, deal funding. I fund other people’s deals. It doesn’t matter where I’m sitting. They’re watching it. Their babysitting deal. I’m just the bank. That’s another. I’m just going to use three examples that we’ve done so you can think about it when you’re doing this for yourself.

The third one is if we’re doing a flip or anything that needs somebody’s attention to be there and do it. It’s not us. We have boots on the ground doing it for us. We will have trusted people that work side by side with us. They’re going to be right there with the property handling whatever it takes and we’re going to be again on the back of the boat available if they need us and to hand over bank water instructions when the money is coming in.

Which is where we are now and have been for quite some time. You have to sit down with yourself and think to yourself what freedom means to you. I’ll give you a few examples. I’ll use myself first. For as long as I can remember, freedom to me is all tied to money because I can do with filling my time and other projects once the money is there. As long as I can remember, I’ve accumulated a ton of cash-cash or real estate. Anything that’s generating money.

Freedom is all tied to money. You can focus on filling your time with other projects once the money’s there. Share on X

Make enough to live on. The interest income or dividend and interest income on the cash or the rental income, if there’s any leftover on the real estate, then you are truly free. You’re free to start another company. You’re free to tell everybody around you. You don’t want to start another company because you don’t care. You’re free to buy a sailboat. You get a girl or whatever it is. You’re free. That’s true freedom for me.

Think about a guy like Elon Musk. Nobody understands why he still goes to work with his equity. He has not achieved whatever that version of freedom is for him. There’s all kinds of examples that you can use. There’s a guy I know who owns a successful bar restaurant. It’s small but it’s very successful and he’s doing another restaurant. He asked my advice several times, what should I do here? How should I deal with this? He knows that Jill and I are very money oriented. He knows we’re successful. He’s certainly not to our level but he wants to open this new place.

I said, “Great. That’s easy. Don’t serve any food. Make sure you just get a liquor license because it’s a lot more profitable. People come in, they get drunk and order more drinks. It’s going to be way more profitable. There’s no real staff.” He looked at me and this has happened four or five times in 2024. He looks at me shocked that I’m saying that. The reason I found out later is because he needs to express himself as a culinary person, as a designer of dishes and the way a restaurant looks.

That’s freedom for him. If he goes to work in that new restaurant if it works and some version of it will because he’s so into it. That’s his ticket to freedom. That seems to me like a life sentence of working in a restaurant. I don’t care if you own it or not. Everybody’s got a different sense of whatever. As far as financial freedom goes, I don’t know what’s more free than having tens of millions of dollars in the bank that’s generating interest income, dividend and interest income that’s completely secure and FDIC-insured, then you can go do whatever you want. Open a restaurant. Watch it fail. Laugh about it. Sink the boat.

We have changed roles a little bit. You laugh, I cry. It used to be the opposite of, “That’s funny.” You’d be crying. Now, it’s changed. I don’t know how that happened.

Sink the boat. Buy another one. Who cares? That’s true freedom. That’s just me.

If our insurance company could only see us now.

The Psychological Version Of Freedom

We have a sitting on the boat. If our insurance company could see us now. What’s freedom to you? At this age and everything you know and all of it. Without thinking about it too much. We’re complicating this topic. This is what the whole topic should be. You, reader, figure out what freedom is for you. I’m serious. Take a whole day. Take a day off and figure it out on its own because it will happen.

Freedom, to me, is getting up and saying, “I don’t feel like doing this. I’d rather go to Milan.”

Jill, you’ve been free for a long time.

I know. I don’t know what’s taking me so long.

Let’s see what you and Land Academy are working on.

We have an awesome win to share. I believe we’ve talked about this before, but I’m bringing it up again because it never gets old. Long time member Michelle has a win. She bought a property from a college that was listed for sale for dumb years with 24 beautiful acres just outside of a town next to a golf course. It was listed for $228,000. She’s like, “I’m offering $85,000 and they said yes.” She owned it for a whopping four months. She sold it for $189,000. Can you believe that? The fireside on Facebook Marketplace and there was no realtor commission on the sell side.

I wonder what Michelle’s version of freedom is because she doesn’t need to work at all. She gets a kick out of doing these deals.

I’m going to talk about this for a moment. She had a big goal. There was a seven-digit goal for 2024 and she hit it. I don’t know what her digit goals are in 2025.

I worked with that woman.

I’m guessing it’s probably doubled that.

This just crossed my mind. I worked in a health care institution. I’m pretty high up in healthcare. We’re hiring people in the finance area. Not in the care area at all. We are hiring people constantly from all walks of life and we hired this woman. I think I told the story one time in the distant past on the show. We hired this woman and for whatever reason, of all the people we hired, I still remember her. There’s just something unique about her.

She demanded that she can have a corporate apartment. We wanted to hire her. She had a great experience and the whole thing turned out great. She needed a corporate apartment, which we had a bunch of. She wanted access to a corporate car, which after some finagling we did. It was a small amount or token amount compared to how much money she was making from a salary standpoint. We did it and she would show up. She never wore any makeup.

She worked like eight hours to the second. She was that person that when it clicked at 5:00, she packed your stuff up and left. About eight months later, she was gone. She turned in her resignation and that was it. She did a good job. I asked another person that worked close to her, “What the hell was that?” She said, “She had a very specific financial goal. She makes enough money for a certain amount of money. She goes and takes five years off, travels around the world and then comes back and does it again.” That’s freedom for her.

I get it.

She had some accumulated balance and then I’m sure how she traveled around was not like how we do it. I don’t think she went and bought Chanel after that.

Did she dress well?

No. This is long-term care. There’s brilliant people that don’t care what they look like. We have a few questions from you in our online Land Academy Discord community.

Community Q&A: Handling The “Spouse” Objection

We have three questions. Number one, Stefano asked, “How do you handle sellers who keep saying, ‘I need to talk to my spouse’ but then they never move forward?”

You need to talk to your spouse. We could do a whole show on this. Why do you need to talk to your spouse about this stuff?

It’s because they want to still have a spouse. Here’s my thing.

Why would you go talk to your spouse about it? I would put the whole deal together and this is what you would want me to do. Put the whole deal together, come to you and say, “Jill, I got this whole thing altogether. You don’t have to lift the finger. That property in X, Y, and Z, we’re going to get $55,000 for it. Does that work for you?” You’re going to say no way or yes.

I have ruined you.

That’s for sure.

Most couples aren’t like that. I know a whole lot of my friends that want to be involved every step of the way. They don’t want you to go behind their back. They would say that. I’m not kidding. “Why didn’t you involve me? Why don’t you tell me? I want to know what you were spending your time on. You should have brought this to me sooner.” Seriously, that would happen.

I know how that would end.

I know. Again, I’ve ruined you.

Wouldn’t you do the same thing for me, put the whole thing together and say, “It’s $55,000?”

We’re not normal people, I don’t think. Follow me on this one. I want to help Stefano. There’s one or two things going on. One is, that’s his way of kicking the can down the road. That person doesn’t want to sell and that’s their way of saying, “I haven’t got to go.” They don’t want to sell. That’s just pushing you off until you stop calling them. Number two is, they are afraid of their spouse. Which I have dealt with. I’ve dealt with both. In situation number one, you have to get to the bottom and find out. What is it? Is it the price? Do you guys still think you’re going to build your dream cabin there? What’s going on?

Pick up a different excuse, by the way. All sellers who are reading, make up a different excuse than that.

That’s number one and when you uncover that, it’s either going to happen or you move on. Now, in situation number two, which is they do need to talk to their spouse. There’s something going on there to which it’s probably easier for me as a woman. If it’s a man’s spouse, bring it on. I would love to talk to them. Number two, if it’s a female spouse, I can talk to them. I can go either way. It’s hard if it’s a man trying to buy from another man and the me buyer, who says, “Put your wife on the phone, please.” That’s not going to fly. “Honey, this strange man named Jack wants to talk to you.” That’s awesome.

Take your time.

I’ll be in the garage. That won’t fly, but this is again why with women, it’s easier sometimes. I can go, “What’s going on? Let me talk to her. Hi Mrs. Smith, my name is Jill. I’ve been the crazy woman calling your wife or calling your husband five nights in a row. Apparently, he’s been afraid to ask you this question. He wants to sell the property. I want to buy the property. Does it work for you? Here’s where we are.” That’s how you do it and now you get to the bottom of that. Probably, it’s like, “This sounds great. I do have some questions, Jill, because I don’t know much about you. Can you tell me about your company? Can you tell me about your plans? Can you tell me about how the transaction would go?”

That’s what will most likely happen and has happened based on experience here. You answer those questions and then everybody’s happy. You need to do this, too. I am going to bring this up. If you don’t, Stefano, when you’re talking to a seller and there’s two people listed. Even if there’s not two people listed, but you discover that they’re married or they have a partner or a husband or something like that. You need to make sure and ask that question, is everybody on the same page here? It could come back to bite you because you don’t want to be three weeks into escrow and then they go, “My wife found out and said I can’t sell it.” That’s on you, Bud.

When you’re talking to a seller and there are two people listed—or even if there aren’t, but you find out they’re married or have a partner—you need to make sure to ask, ‘Is everyone on the same page?’ because it could come back to bite you. Share on X

That’s a real common problem with real estate agents. Put a whole entire residential deal together and find out their spouse had no intentions of moving at all. Let’s take another question, Jill.

Community Q&A: Scaling Up Deal Size

Number two, Corina wrote, “When do you recommend switching from smaller deals like $5,000 to $10,000 profit to bigger ones?”

Now.

I was going to say that as soon as you can.

Immediately.

I love this. I came up with this couple years ago, add a zero. If you’re comfortable, like buying for $5,000 and selling for $10,000. I know it sounds crazy, but try it. Buy for $50,000. Add one zero and sell for $100,000 and watch how comfortable you get fast number one and number two. It’s shocking and awesome how much easier those deals are. When someone is scraping together $10,000 because that’s all they have and they want that property.

They need three weeks to sell this and come up with that and make sure this clears and get that one more paycheck in. That’s a different buyer. There’s a lot going on there and a lot that could fall apart, versus when you’re selling something for $100,000. All they’re doing is, “I just need to move this money into this bank account and then I’ll be able to get the wire done.” How does that sound on the third thing? You’re like, “What just happened?”

Bigger deals are a lot easier almost always.

Their profession. They typically do their homework way ahead of time. It’s $100,000. By the time they’re picking up the phone and calling you, they’ve done all their leg work. They just may have one or two last questions for you and then it’s go time.

Community Q&A: Access Without A Full Title Search

Kidding aside, just get there. The more money you make, the more you’re going to be good at freedom. Final question from our Facebook group.

Tyler asked, “Is there a quick way to double check legal access without worrying about a full title search?”

The pro tip/way that I do it or we do it, is to pull up a plat map. This works in more developed states, versus very rural counties or rural states. In fact, I’ve never run into a county where it hasn’t worked. If the plat map shows dotted lines, which is where the easement has been platted for the roads. You may not be physically there but the roads have been platted in, then you’re 99.9% sure it’s got legal access. It all has to do with getting the plat map. If it’s a real urban county, you can go online and get it. They’re going to have it posted.

Pull it up and see it.

In some counties, you have to call them and they’ll send you one.

The other thing is to ask the county. Pick up the phone and call them and ask them.

The truth is that’s what a title agent that’s doing the title policy is doing. Sometimes, they’re physically in the county pulling those maps and checking. That’s what they’re looking for. It’s that plat map. If you see a plat map with just a square on it, somebody literally rewrote the legal description that that property does not have legal access. It’s just a square. If the property is truly square, whatever the shape of it is. You pull a plat map and you’ll see a square on a piece of paper or the outline of the lot line.

That’s a good question and I like that. Fellow investors, there’s a big announcement. We’re so excited. Deal Complete has officially launched. It. All numbers are open, are in, using it and loving it. I can’t believe it. The feedback that we’ve got has been like little teeny, little tweaks. It is amazing. Our team is awesome. It is open to the public and available to you. It explains more about who we are, what we do, and how Deal Complete can help you.

It doesn’t matter what land deal or real estate deal. It could be land, houses, or commercial stuff. Deal Complete will work and help you and save so much time. The eBook is called The Land Investors Easy Button: How to Automate Your Deals From Offer to Close. Inside, you’re going to get exactly how to pull data, how price offers what we do now using AI to make them even better and to get a full mailer out the door. Not having to learn Excel and spreadsheets.

Not doing your own scrubbing and also that takes away a lot of the headaches for many of us. Head over to DealComplete.com/ebook and grab your copy now. If you like this episode, please drop us a comment. By the way, if you share a win or a question just like the ones that we answered here. Yours might just be featured on the next episode.

Join us for another interesting episode. You are not alone in your real estate ambition. We are Jack and Jill, information and inspiration to buy undervalued property.