Why Owning Hundreds of Rental Properties Doesn't Automatically Make You Rich
When people hear that I've owned hundreds of rental properties, they usually assume I've made millions and never have to worry about money again. I get asked all the time what it's like to own a massive rental portfolio, and one question comes up more than any other:
"Did owning hundreds of rental properties make you rich?"
My answer surprises most people.
No—it didn't.
In fact, building a portfolio of more than 600 rental units taught me one of the hardest lessons of my investing career: owning more properties doesn't automatically create wealth. If your cash flow is weak, your expenses are rising, or your debt is working against you, a large portfolio can become a financial burden instead of a financial blessing.
I didn't learn that lesson from reading books or watching YouTube videos. I learned it by living through it.
If you're investing in real estate—or thinking about scaling your portfolio—I want to share what happened to me so you can avoid making the same mistakes.
Quick Takeaways
How I Started Building My Rental Portfolio
Like many investors, I got into real estate with a simple plan.
I would buy properties, renovate them, rent them out, and let my tenants pay down the mortgages. Over time, I expected rents to increase, my equity to grow, and my portfolio to become more profitable every year.
At first, everything seemed to be working exactly as I imagined.
When I started buying properties in 2018, interest rates were incredibly favorable. Most of my loans were around 4%, and some were even lower. That made the numbers work beautifully.
If a property brought in $1,000 a month in rent and only a few hundred dollars went toward the mortgage, I still had enough room to cover insurance, taxes, maintenance, and other operating costs while generating positive cash flow.
The more deals I completed, the more confident I became that scaling was the fastest path to wealth.
Looking back, that's where I made one of my biggest assumptions.
When Everything Changed
Real estate markets don't stay the same forever.
Between 2022 and 2023, interest rates climbed much faster than I expected. Loans that once came with low interest rates suddenly became far more expensive. At one point, I even took out financing at 10% simply to stabilize my business while navigating the changing market.
At the same time, property values began falling in many markets.
I watched values decline while borrowing costs increased, creating pressure from both directions.
That combination completely changed the economics of many investment properties.
What looked like a strong portfolio during a rising market became much harder to manage when financing costs increased and values softened.
I Mistook Growing Equity for Real Wealth
One of the biggest mistakes I made was believing that my growing net worth on paper meant I was becoming wealthier.
Every few months, I'd update my spreadsheets and watch the numbers climb. Because I was buying so many properties and adding value through renovations, it looked like I was creating millions of dollars in equity.
I thought I was winning.
But when the market shifted, I realized something important.
Paper equity doesn't pay your bills.
Cash flow does.
When property values declined and financing became more expensive, those impressive numbers on my spreadsheets didn't help cover monthly expenses.
That's when I realized I'd been measuring success the wrong way.
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About Johnoson Crutchfield
Johnoson Crutchfield is a real estate investor, coach, and host of the Grab the Map podcast. He helps aspiring and active investors move beyond analysis paralysis and take the consistent actions required to close real estate deals.
Drawing from years of hands-on experience, Johnoson teaches practical, real-world strategies focused on finding opportunities, building relationships, securing funding, and making offers. His approach emphasizes weekly execution over endless education, helping investors create momentum through simple, repeatable actions.
As the leader of the Wealth and Real Estate community, Johnoson shares lessons from real transactions and real conversations with lenders, sellers, and investors. He is a strong advocate for local banking relationships, seller financing, and private lending as powerful tools for growing a real estate business.
Through coaching, content, and community, Johnoson has helped investors gain clarity, build confidence, and take meaningful steps toward closing their first—or next—deal.
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