I’m about to share something that might upset some of my investor friends in the country, so prepare yourselves.
If investing in land is the best thing you’ve ever done, it could also be what’s holding you back.
I know how that sounds. Believe me, I have struggled with this idea for a long time. But after a few years of watching myself and many other investors go down this path, I’ve come to believe something that most people in this space wouldn’t say out loud: just because something works doesn’t mean you should do it forever.
Investing in land is one of the best businesses I know. I don’t say this to be dramatic or to go back on anything I’ve ever taught. I sincerely believe in it. But I also don’t think land investing has ever been my goal, and I don’t think it should be yours either.
When victory becomes the wall
Maybe you’ve already discovered it for yourself. You’ve made some deals, you’ve made some money, maybe more money than you ever thought you’d see in your life. If that’s where you are now, I’m really happy for you. You should be proud, because most people never get there.
But after things go well for a while, there’s one question that almost no one bothers to ask.
Is this it?
Is this the final version of your life or is it just the first step?
I’ll make you a bet right now. If you are competent enough to succeed in real estate, you are grossly underestimating what you are capable of. And I don’t say that lightly, because this pattern shows up over and over again with people who win big at one thing.
The pattern of people who do not conform
Take Arnold Schwarzenegger for example. The guy wins the Mr. Olympia seven times, which in itself is a lifetime achievement. Most people would stop right there and be aimless for the rest of their lives, and no one would have blamed them. But Arnold didn’t do that. He went to Hollywood and became one of the biggest actors in the world. He then ran for governor of California and won. Twice.
Imagine for a second if Arnold had stopped after his bodybuilding career. Nobody would have judged him. But look at all you would have missed.
The thing is, he’s not the only one. This pattern appears again and again with people who reach a high level.
- Oprah Winfrey: She took a local news anchor job and turned it into the most successful daytime talk show in television history, then built a media empire with her own production company (Harpo), magazine (O) and cable network (OWN). The interview chair was just her launching pad to billionaire status.
- Dwayne “The Rock” Johnson: He dominated professional wrestling as one of the biggest WWE stars of all time, then jumped to Hollywood and became one of the highest-paid actors in the world. He also created a tequila brand (Teremana), a production company and a stake in the XFL.
- George Foreman: He won an Olympic gold medal, became a two-time world heavyweight champion and then turned a cooking grill into a more than $200 million payday by licensing his name. Not a bad second act for a guy most people wrote off after losing to Ali.
- Magic Johnson: He won five NBA championships and three MVP awards, and then quietly built one of the most impressive post-career sports business portfolios. His holdings include stakes in the Dodgers, Lakers, Sparks and a long list of franchises and real estate companies.
- JK Rowling: She went from being a single mother on welfare to writing the best-selling book series of all time with Harry Potter. He then expanded that idea to movies, theme parks, plays, and a digital universe that continues to generate huge amounts of revenue decades later.
- Cuban Marks: He sold Broadcast.com to Yahoo for $5.7 billion in 1999, bought the Dallas Mavericks and won an NBA championship as owner, and now uses Shark Tank as a launching pad for a portfolio of consumer brands and his low-cost pharmaceutical company, Cost Plus Drugs.
- Jessica Alba: She built a successful acting career with major roles in film and television, then co-founded The Honest Company as a side project focused on safer baby products. The company went public in 2021, briefly making it a billionaire.
- Gwyneth Paltrow: He won an Oscar at age 26 for Shakespeare in Love, then founded Goop as a weekly email newsletter and grew it into a lifestyle brand worth hundreds of millions. She is now also a published cookbook author and CEO of a public welfare empire.
- Dr. Dre: He pioneered West Coast hip-hop with NWA and Death Row Records, then launched Aftermath Entertainment, which signed Eminem and 50 Cent. After that, he co-founded Beats Electronics and sold it to Apple for $3 billion in 2014.
- Tony Hawk: He became the most recognized skateboarder in history with 73 competition victories, then launched a video game franchise (Tony Hawk’s Pro Skater) that has sold more than 30 million copies. He also runs his own skateboard company (Birdhouse) and a foundation that builds public skate parks for underserved children.
- Robert Downey Jr.: He returned from a career-ending addiction to anchor the Marvel Cinematic Universe as Iron Man, becoming one of the highest-paid actors in Hollywood. Since then, he launched FootPrint Coalition, an investment firm focused on environmental technology, as well as his own production company.
- Reese Witherspoon: She won an Oscar for Walk the Line and then founded Hello Sunshine to produce female-led stories like Big Little Lies, Little Fires Everywhere and The Morning Show. He sold the company for around $900 million in 2021 and also runs one of the most influential book clubs in the country.
Each of them won once, and instead of treating that victory as a goal, they used it as proof that they could win again at a higher level.
So let’s bring this to you again. Maybe you are a land investor. Maybe you’ll move house. Maybe you own rental properties. Excellent. But what if that’s not your final destination? What if it’s just your launching pad?
The well-paid hamster wheel
This is where it gets awkward, and I’ll be completely honest with you because I’ve experienced this myself.
Many people find the land investment business and fall in love with it. Works. Generate money. They leave the job they hated, pay off their debts, and feel free for the first time in their adult lives. Then something subtle happens. They stop thinking. They stop evolving. They settle into the routine and before they know it, they’re back on a hamster wheel.
It’s a well-paid hamster wheel, sure, but it’s still a hamster wheel.
Because if your income depends on you constantly landing new deals – and let’s be honest, that’s exactly how the land investment business works – the race is never over. You’re always a slow month away from anxiety. Every quarter starts at zero. Each victory must be repeated the next month, and the month after that, and the month after that.
At some point, the goal has to change. It has to evolve from just making money to building something that keeps paying you even when you stop showing up.
From active income to real wealth
That “something” could be rental properties. It could be self storage. They could be apartments or commercial agreements. It could be a business completely unrelated to the real estate sector. It could be investing in other people’s deals, creating something digital, or delving into something you really care about.
The vehicle isn’t really the point. Making the change is the point.
Land investing is amazing at one thing in particular: generating large amounts of cash quickly without taking on large risks. That’s the real advantage of this business, and it’s huge. But it was never designed to be the goal. Unless your dream in life is spreadsheets, ringless voicemails, and talking to motivated salespeople until you’re 80, you probably don’t want to do this forever.
That’s why I’m going to say something that very few people in this industry will admit out loud.
Every land investor should get out of their real estate business. The same goes for fins and wholesalers. Not because the business is bad, because it is not. But because you can do it better and the skills you have developed in this business are worth more than you think.
Skills are bigger than business
Think about what it really takes to be successful in land investing.
Lonely. Discipline. Problem solving. Relentless follow-up. Negotiation. Emotional control.
The ability to move forward when a deal falls through at the closing table. The willingness to take calculated risks while everyone around you plays it safe.
Most people don’t have those skills. You do. And those skills are worth MUCH more than littering.
For me, investing in land was the starting point. It gave me freedom and a financial foundation I never thought I would have. But it was the launching pad, not the destination. Finally, I built REtipster.com. Then I got into the self-storage business. Then I co-founded a software company (Stride CRM, if you’re curious). And there’s probably something else I haven’t gotten into yet.
The point is not to brag about any of that. The point is that I intentionally built income streams that don’t depend on me being present every day, and I stopped putting all my eggs in one basket. And I can tell you from experience that making that change changes your entire life.
The pressure decreases. It stops being a question of survival. Offers become optional. I do them because I want to, not because I have to. And believe me, that’s a completely different life than the one I had when each month started with a blank tube and a knot in my stomach.
So what’s your next step?
This is the question I want to leave you with, and I want you to sit with it for a minute before we continue.
What is your next step? It’s not your next deal. Your next level.
Because if you’ve come this far, you’re not stuck. You arrive early. Don’t treat your first big victory as the finish line. Treat it as proof that you can do hard things and then do another one.
The world desperately needs more people who actually keep going. If you’ve already proven you can do it once, there’s no reason you can’t do it again. Only this time, build something that will pay you whether you show up or not.
That’s the real game. Not the next deal. The next level.
Leave a comment below and tell me what you’re building next. Not what you’re doing. What you are building. I want to know what your next chapter will be like!
