Borrowing Money Is the Strategy: Why I Pick Real Estate Over Stocks
Most people think I’m crazy when I say I love borrowing money. But I do. I borrow it on purpose—to buy assets that pay me every month.
Not liabilities. Not dreams. Real, cash-flowing real estate.
I’ve invested in stocks too. Click a button, sell fast. No tenants, no roofs. But also… no control. You can’t walk into a stock and fix it. You can’t negotiate its terms.
With real estate, you can. I’ve controlled million-dollar properties with around $100,000 down. I’ve raised values by improving curb appeal, strengthening income, and choosing the right zip code. I’ve worked with partners to acquire properties I could never have touched alone. Real estate lets me shape outcomes—stocks don’t.
That’s why I’m sharing this with you: to show you how I think about the real estate vs stocks debate, and why I keep choosing real estate.
This isn’t a theory. I’ve borrowed money to buy rental properties, apartments, and even hands-off businesses. I’ve used partnerships and lending tools to scale. I’ve watched appreciation over decades and used the tax code to keep more of what I earn.
I’ll break down the contrast in five key areas:
- Control: Why real estate gives you levers that stocks never will
- Leverage: How to buy more than you “should” be able to
- Taxes: Why the IRS treats real estate differently (in a good way)
- Team: How partnerships make big deals possible
- Simplicity vs volatility: What stocks offer, and what they cost
You’ll also hear why I believe real estate is the better long-term play, even if the barrier to entry feels higher. I’ll explain the problem with checking your portfolio daily. I’ll walk you through the power of buying at a discount—just like we do in our investor group. And I’ll challenge you to stop waiting for perfect timing.
This isn’t just about investing. It’s about direction. Focus. Ownership. Not just of property—but of the results you’re trying to create.
Real estate lets you do that.
Stocks are fine. But they’re not the map.
Real estate is. Let me show you why.
Real Estate Buys You Control
With stocks, you’re just along for the ride.
You buy a share and hope the company performs. Hope the market reacts well. Hope some macroeconomic event doesn’t tank everything overnight. But there’s no fixing a stock. No walking into an index fund and changing its value.
Real estate is different. “You can influence the value by location, repairs, and income.” That one sentence explains why I keep choosing it over and over again.
I’ve stood on the sidewalk of properties I’ve bought, thinking: this block is improving. This unit needs upgrades. This tenant wants to renew. Every one of those elements plays a role in the property’s valuation. I’m not just hoping—I’m operating.
“You can drive by real estate. You can see it. You can touch it.”
That’s not just comforting. It’s actionable. I can move the needle. I can impact performance.
The value of real estate is something I can influence.
Here’s what that actually looks like:
- I choose location intentionally, buying in areas with job growth, strong schools, or upcoming development.
- I renovate units to improve curb appeal and raise rents without overpricing.
- I monitor tenant quality and lease terms to protect income consistency.
- I adjust expenses and operations to improve net operating income.
- I raise value by increasing income, not just waiting for the market.
- I make capital improvements that add measurable value, not just cosmetic fluff.
- I buy at a discount so I start with built-in equity, not inflated pricing.
Every one of those is a control point. It’s a lever I can pull. You don’t get that with the S&P 500.
I’m not guessing. I’m guiding. When you treat real estate like a business—not a bet—you stop reacting and start directing.
There’s a reason my properties don’t whipsaw up and down when the headlines change. I’ve built them to withstand noise. To produce. To last.
That’s the kind of control I want in my wealth plan. And that’s why real estate isn’t just “an investment” to me.
It’s a platform I can shape.
Leverage Is a Wealth Multiplier
One of the biggest reasons I choose real estate over stocks is simple: leverage.
“You can buy a million-dollar asset with around $100,000.” That’s not theory. That’s what I’ve done—and continue to do. The system is built to support it. Lenders want to back good real estate deals. Partners want in. You don’t need all the money to buy the deal. You need a good plan and the right structure.
“I love borrowing money—to buy cash-flowing assets.” I don’t borrow to consume. I borrow to own. If you understand the numbers, you’re not overextending. You’re expanding.
Here’s the check I run every time I use leverage:
- Does the asset cash flow from day one? If it doesn’t pay me now, I’m not betting on future appreciation.
- Am I bringing at least 10% equity? That’s usually the minimum to get lenders interested. It also gives me enough skin in the game.
- Is the financing smart? I look for fixed-rate options, creative terms, or seller financing that won’t reset or balloon unpredictably.
- Does the deal withstand stress tests? I run the numbers assuming lower rent and higher expenses. If it still works, I move forward.
- Can I add value after purchase? That might mean cosmetic upgrades, rent increases, or operational efficiencies.
- Am I buying at a discount? I aim to create equity from the start, not wait for it to happen.
- Is this a one-man play or a team move? Bigger deals need partners. I decide upfront whether to fly solo or bring others in.
Here’s a quick story to show you what I mean.
A few years back, I came across a small apartment complex listed at $1.1 million. Most folks would have scrolled right past it. But I saw the potential. I brought $115,000 to the table—part my own money, part from a trusted partner. The bank financed the rest. I knew the rents were under market, the units needed light rehab, and the location was in the path of development.
We raised rents by 20%, upgraded the exterior, and boosted net income. Less than 18 months later, that property appraised at $1.45 million. That’s what leverage does when you use it right.
“You can get control of something worth so much more than the capital you actually have.” That’s the game. Stocks can’t match it.
The Tax Code Likes Real Estate
One thing that confused me early on was why real estate investors seemed to pay less in taxes—even while earning more.
It didn’t make sense until I got my first rental property and filed my taxes that year. I expected to owe. But instead, depreciation had wiped out most of my taxable income from the property. That’s when it clicked: real estate isn’t just profitable. It’s protected.
Let me give you an example.
I had a duplex in a mid-sized town—nothing fancy, just steady rent. I made around $12,000 in net income that year. But when I added up mortgage interest, property taxes, repairs, and depreciation, my taxable income was nearly zero. Not only that, but I could carry forward depreciation into future years. Meanwhile, friends of mine who sold stocks had to cough up capital gains tax—no shelter, no flexibility.
That’s when I realized: the tax code is written to reward ownership of physical, income-generating assets.
“You can sell that home, and in a lot of cases, up to a certain profit, you don’t pay taxes on those gains.” That’s not a loophole. It’s a policy.
Real estate lets you build wealth without letting the IRS take a bite out of every win.
Here are the checkpoints I follow to keep my tax strategy tight:
- Use depreciation fully: Every year, I apply allowable depreciation to reduce taxable income on investment properties.
- Understand the primary residence exemption: Living in a home for 2 years opens the door to tax-free capital gains when you sell.
- Leverage 1031 exchanges: I reinvest profits into larger deals without triggering taxes, deferring gains legally.
- Track improvements, not just expenses: Some upgrades increase basis, which lowers taxable gain on exit.
- Talk to a real estate-savvy CPA: Not every accountant knows how to work the tax code for investors.
Stocks might feel simpler. But every dollar taxed is a dollar not reinvested.
With real estate, I’m not just building income. I’m keeping more of it—legally, ethically, and consistently.
Real Estate Is a Team Sport
People think real estate is lonely. It’s not.
You don’t have to do it all yourself. In fact, you shouldn’t.
“You don’t have to go at it alone. Real estate is a team sport.” That’s one of the biggest mindset shifts that helped me go from single-family homes to bigger, better deals. The moment I stopped trying to be the hero, things changed.
I remember eyeing a 36-unit building that felt way out of reach. I didn’t have the full down payment, didn’t know how I’d manage that many tenants, and the rehab budget alone was intimidating. Old me would’ve passed. But instead, I called a partner who was looking for a passive investment and connected with a property manager who’d handled buildings twice that size.
We closed. We held. We cash flowed. I didn’t do it solo, and I didn’t need to.
Here are the rules I follow when building my real estate team:
- I bring something to the table—whether it’s hustle, deal flow, or management skill.
- I don’t chase money partners who don’t align with my values.
- I stay transparent with numbers, timelines, and risks—no smoke and mirrors.
- I only work with people who’ve done what they say they can do.
- I clarify roles before the paperwork—so there’s no drama after the deal closes.
“Deals come from trust and communication.” Not from shiny brochures or promises. From showing up consistently, saying what you’ll do, and doing what you say.
The cost of staying the same? You’ll keep missing the buildings you think are “too big.” You’ll scroll past opportunities because you assume you need to have it all figured out on your own.
But when you build a team, you multiply your chances. You don’t just grab the map—you walk further with it.
Stocks Are Simple—But That’s the Problem
I own stocks. I’m not here to bash them.
But I don’t depend on them. I don’t build my plan around them. As easy as they are to buy, they’re just as easy to lose sleep over.
“I have no control over any stock I invest in.” That line says it all. I’ve tried guessing market trends. Tried picking the right time to enter or exit. It always felt like gambling in a room where someone else makes the rules.
One week I bought into a company that had been solid for months. No debt. Growing revenue. Two days later, a headline sent it diving. Nothing changed in the business—but everything changed in the price.
That’s the problem. You can do everything right and still feel like you’re just along for the ride.
Real estate isn’t like that. When I buy a property, I’m not guessing. I’m working the plan. Managing the asset. Influencing the outcome.
Here are a few truths I’ve learned the hard way:
- Stocks are liquid—but that also makes it easy to panic and sell.
- You can’t fix a stock. You can’t improve it. You can only hope.
- The market doesn’t care about your plans, timelines, or stress.
- A good real estate deal makes money even when no one’s watching.
- Daily volatility is noise. Ownership should feel stable.
Stocks are convenient. But convenience has a cost. If you’re tired of reacting and ready to take charge, it might be time to stop clicking and start closing.
Don’t Just Watch—Grab the Map
I started this by telling you something most people find hard to believe: I love borrowing money.
But now you know why. I don’t borrow to consume—I borrow to build. To control assets. To shape outcomes. That’s what real estate gives me, and that’s what I want you to consider.
If you’re still checking your stock portfolio every morning, still guessing when to buy or sell, ask yourself: what are you actually building? I’ve been there. Real control feels different. You’re not waiting on the market. You’re working the plan.
Real estate lets you borrow money, team up, use the tax code, and improve something tangible. “Deals come from trust and communication.” Not noise. Not charts. Not crossed fingers.
If you remember one thing, remember this: stocks are fine for liquidity—but if you want leverage, control, and long-term wealth, real estate wins.
Start by shifting your lens. Don’t just look at whether something might go up. Look at what you can touch, improve, and own. Find the people already doing deals. Find the next asset you can influence.
You don’t have to be rich. You don’t have to be ready. You just have to be willing to grab the map—and start walking.
About Johnoson Crutchfield
Johnoson Crutchfield is a real estate investor and coach who helps others close their first or next deal using leverage, control, and repeatable systems. He addresses the gap between wanting to invest and actually getting under contract by showing a clear, numbers-driven path to take action.
Through the Grab the Map podcast and YouTube channel, Johnoson shares real-world strategies focused on rental property acquisition, offer structuring, and long-term wealth building. He buys houses, apartments, and hands-off businesses, and offers lending connections when deals meet high standards.
Johnoson’s approach shifted when he stopped trying to do everything alone. Partnering on a 36-unit building showed him the power of team-based investing and strategic lending. Tax advantages and value-driven renovations further reinforced his belief that real estate isn’t just profitable—it’s structured for ownership.
He teaches from experience, not theory, helping others build assets they can see, improve, and grow.
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