A Parable: The Investor Who Wouldn’t Let Go

[Grant Shipman]

The Investor Who Wouldn’t Let Go

Once upon a time, in the bustling city of Crestwood, there was a real estate investor named Michael Carter. Michael had built his portfolio from the ground up, starting with a single rental property. Over the years, he acquired more homes, duplexes, and even a small apartment complex.

But despite his growing success, Michael had one fatal flaw—he couldn’t let go.

The Burden of Control

Michael was everywhere. He personally screened every tenant, handled every maintenance request, and even showed up to mow the lawn at his properties when the landscapers were running late.

His phone rang constantly—contractors, tenants, vendors—all needing his immediate attention. He prided himself on being hands-on, convinced that no one else could do the job as well as he could.

One evening, exhausted from another 14-hour day, Michael met with his friend James, a seasoned real estate investor.

"You look terrible," James said, sipping his coffee. "When’s the last time you took a day off?"

Michael chuckled. "I can’t afford to take a day off. If I don’t handle things, everything falls apart."

James shook his head. "That’s your problem. You think working harder equals making more money. But let me tell you a story."

The Farmer and the Seeds

"Imagine two farmers," James began. "Both have fields of fertile land. The first farmer tries to plant, water, and harvest everything himself. He spends every waking moment in the field, making sure every seed is placed perfectly. But no matter how hard he works, he can only plant so much before exhaustion sets in."

"The second farmer?" James continued. "He hires workers. He teaches them his method, lets them handle the planting, and trusts the process. While the first farmer struggles to keep up, the second farmer’s fields are growing ten times faster because he let go and focused on the bigger picture."

Michael leaned back in his chair, considering the lesson.

"So, you're saying I should be the second farmer?" he asked.

James nodded. "Exactly. Real estate isn’t about doing everything—it’s about building systems and trusting others to help you grow."

The Turning Point

That night, Michael went home and made a list of everything he was doing that someone else could handle.

📌 Tenant Calls & Leasing? → A property manager could do that.
📌 Maintenance Issues? → A trusted handyman could handle repairs.
📌 Accounting & Rent Collection? → Automated property management software could streamline it.

Over the next few months, Michael slowly started letting go. At first, it was terrifying. What if the property manager made mistakes? What if the contractor overcharged him?

But then, something incredible happened—his business started thriving.

With fewer daily distractions, Michael had time to find new investment deals, build relationships with private lenders, and even take a vacation.

His portfolio doubled in size within two years.

And for the first time in a decade, he wasn’t stressed.

The Lesson: Let Go to Grow

Michael realized the secret of successful investors: You don’t build wealth by working harder—you build wealth by working smarter.

By letting go, he gained more than just free time—he gained a scalable, sustainable business that could grow without burning him out.

Are You Like Michael?

🤔 Are you still handling everything in your real estate business?
🤔 Are you afraid to delegate because no one else can do it “as well as you”?
🤔 Are you working yourself into exhaustion instead of growing your investments?

It’s time to let go and build a real business—one that thrives without consuming your entire life.

Discussion:

1️⃣ What’s one thing in your real estate business you need to let go of?
2️⃣ What’s stopping you from delegating or automating more of your tasks?
3️⃣ Have you had an “aha” moment like Michael? Share your story!

Let’s talk below! 🚀👇