The Journey From Side Hustle To Full-Time Investing

This is episode number 2,148. Jill and I are talking about how to transition from side hustle to full-time land investing. We ended our natural transition from the topic in the last episode to the topic now. We were talking about staying motivated when you’re not seeing results. I ended on this younger generation who was born with the internet in their mouth. They have a lot of undue pressure. It comes from a very positive place. There’s a lot that’s expected of this generation that was not expected of generations before it. Information is at everyone’s fingertips. They’re expected to process all this information at a very young age and make it a positive situation for themselves. I don’t think kids at a young age are supposed to do that.

They’re expected to know how to dig through, sift through it, and extrapolate the good stuff. I don’t think it’s possible.

Every single figurative page you turn on the internet is a constant reminder of, “There’s someone else more successful than me. Somebody’s got more views, clicks, likes, and money. They have a faster car, cooler girl, and all of it.” You have to process that into starting your own business, being an amazing person, and ultimately owning your own company before you’re 30, and grossly succeeding when.

In fact, it’s probably way less than two-tenths of 1% of the people that do that. They just happen to be the loudest. Ask your kids, if you have young kids, who they follow on the internet. Some of that is giving away a car because a million more people liked their YouTube channel. They feel like that’s the standard. How many basketball players make it to the NBA?

How many basketball players or people who hang on to their money and make good decisions? That’s a whole other thing.

Six.

That’s good.

This week all week, Jill and I are talking about motivation and confidence. 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.

Jordan T. wrote, “Hello, from Illinois. I’m super excited to join this community and begin a career in land investing. I have a human resources background and have been reading to the Land Academy for months. I finally decided to jump into it by purchasing the content. I’m going into this business with my father, and we should have our LLC set up in a week or two, then the first mailer will go out not long after. Anyways, I look forward to learning from the rest of you guys and securing my first deal.” Awesome. Welcome, Jordan T.

Our topic is called How to Transition from Side Hustle to Full-Time Land Investing. Before we get to the actual topic, I want to continue what we talked about. Should you be doing a side hustle in the first place? Jill and I long before we met each other, we’re hardwired to own our own companies. This is the most successful company that we’ve had buying and selling land. Why? It’s because we failed at tons of these.

We failed at tons of companies together. Both of us are wired to look at that as a positive experience, move on, and find something where it meets our subconscious Zen. We are living our Zen. I can tell you with personal experience that my Zen is somebody else’s nightmare. This world is packed full of people who want to live in a one-bedroom apartment and have a pretty good job.

Have a pension.

Failure isn’t the end—it’s part of the process. We’ve failed at tons of businesses before we found the right one. Share on X

Not a lot of responsibility, or maybe seven children in a little house in the woods. That’s not what we’re wired for. For some reason, in the world that we live in, especially online, no matter who you are and what you truly want, you should have your own company. I don’t believe that. Have a constant self-assessment, be honest with yourself about who you are, and what you want with the people around you.

Making the hard decisions to change things so that you keep peace with yourself is a huge challenge. It’s probably been a challenge for a long time. If you were born into a family that had a farm in Nebraska, you’re kind of wired into that. It takes all the pressure off. “I’m going to be a farmer my whole life. I’m going to get the back 40 like my dad keeps telling me when I get married.”

Hello, Wayne Dyer. Where have you been all week?

That’s not a compliment.

That was very sweet. You’re like, “Have a personal assessment. Be okay and live with that. Come to peace.”

Live it.

Partnering With Others To Overcome Business Weaknesses

I’m joking, but I mean it. I appreciate all that. It’s true. If you’re not hardwired to do it, you’ll die trying, and I don’t want that. I don’t want someone to be miserable. It happens now and then. There are people who get all excited, like, “I can do this. I want to do this.” They get it, and they’re like, “I’m not cut out for this.” Our answer is, before you throw it all away, maybe get a partner.

Maybe there’s a way that you can align yourself with someone who is that owner person. You’ve got the dough. Maybe you’re the money guy and the phone person, or whatever it is and they are the ones who will drive the whole bus and make it great. That does work out sometimes, but you do have to know, understand, and accept your strengths and weaknesses.

Maybe there’s a way that you can align yourself with someone who is that owner person. You’ve got the dough. Maybe you’re the money guy, the phone person, or whatever it is. They are the ones who will drive the whole bus and make it great. That does work out sometimes, but you do have to know, understand, and accept your strengths and weaknesses.

Jill and I love acquisitions. We love getting the money at the end. All the stuff in between, we don’t like it. What do we do? We put people in place to do that. We have a person who runs all of Land Academy, for better or worse. It’s usually for the better. If we were left to the operations of Land Academy and Offers 2 Owners, it would have been gone a long time ago. We would just be two people sitting in offices adjacent to each other where we can’t hear or see each other buying and selling land. We probably would have more money if we just did that.

That’s why we still do that.

We’re not operations people. I’ve said this to people who are much more successful than I ever will be, and they’ve looked at me cross-eyed. “What do you do then?” “I buy stuff.” “That’s it?” “Yes. I don’t operate. I don’t do all the deals or the details. I did one time. I learned I don’t like it.” I was honest with myself and said, “If I continue to do this, I will be burned out in six months and probably never do it again.” You got to be self-assessed on all that. We’re very lucky because Jill and I have gotten each other out of jams before.

We have a lot of people in Land Academy that are born to do this. They have come from other entrepreneurial, successful entities. This is just their next one. That is best when they have that. They’re like, “Bring it. I know how to overcome these obstacles.” The thing is, it’s never a side hustle. It’s just the next thing or something they’re doing in addition to. I don’t think they even word it like that. I’ve never worded it, even though I could probably say that.

The mailer didn’t fail—you failed the mailer. Take responsibility, fix what went wrong, and move forward. Share on X

When I first started, I had a full-time day job, if you will. This was on the side with you, but you were doing it full-time. For me, it was on the side. I never called it a side hustle. It was just the next thing that was going to take over my life. I knew I wanted to make it my life and my career, and then I did it. I was able to do it, finally. When you transition, you want to be so secure and confident and have a lot of the details worked out so that you don’t worry. We used to say this saying, “When you quit your job, you should be saying, ‘I wish I would’ve done that a year ago.’” That’s when you know you’re ready.

It’s year number ten in 2025 that we’ve had Land Academy. A lot of people have come and gone, and a lot of people have stayed forever, so 99.9% of the people that are still around has worked for them very well. It’s not because we provide amazing information or any like that. It’s because they took personal responsibility to make it work. I’ve said this one every once in a while, “I sent a bunch of mail on it, and it didn’t work. I didn’t buy anything.” That’s not because the mail was wrong or the pricing was wrong or any of that. It’s because of what we’re talking about. The mailer didn’t fail. You failed at the mailer. That’s what happened.

You couldn’t write the check.

This has happened to me many times in my career. Not once have I said this doesn’t work or this thing failed. What I’ve said and still say is, “I screwed something up. I’m not going to quit. I’m going to go back and review it. I’m going to figure out what I did wrong. I go back through the steps, and deconstruct everything.” Take it all apart like we do in the RV, and find out what’s wrong with no emotion. Fix it, and then move forward. If you question yourself and have lack confidence, or you don’t stick to whatever you’re trying to do for long enough to gain some experience and confidence to move forward, you probably didn’t want it in the first place. It’s like playing the guitar.

You brought this all right back. That was beautiful. Thank you.

It was like, “Thank God it’s over.”

Do you have another story you want to share?

I could. You know if you want to buy and sell land or you want to be rich.

You know what your motivation is.

You know if you just want to make $80,000 and live your life. That’s fine. The problems are when you’re forcing yourself to do something that you don’t want to do. Join us next time for more fun episodes, hopefully. You are not alone in your real estate ambition. We’re Jack and Jill. Information and inspiration to buy undervalued property.