You’re Leaving Money on the Table: Why CRE Investors Should Start Buying Businesses

If you're already investing in commercial real estate, you're ahead of the curve. You understand asset valuation, cash flow, tax advantages, and the power of leverage. But what if I told you there’s another asset class—just as profitable, often overlooked—that pairs perfectly with the skills you already have?

I’m talking about small business acquisitions.

And if you're a CRE investor who's only thinking in terms of leases, you might be missing out on the ledgers—the financial upside that comes with owning the operation inside the property, not just the property itself.

The Overlap is Closer Than You Think

Commercial real estate and small business ownership might seem like two different worlds. One deals with buildings and tenants. The other with products, services, and customers.

But in reality, the two are deeply connected:

• The success of most commercial tenants depends on the health of the business occupying the space.

• As a CRE owner, your NOI is tied to your tenant’s ability to generate revenue and pay rent.

• The principles of valuation, leverage, tax mitigation, and operations apply in both spaces.

In fact, many of the best-performing CRE investors I know either own operating businesses inside their buildings—or wish they did.

Why CRE Investors Are Uniquely Positioned to Buy Businesses

If you're experienced in real estate, you're likely already good at:

• Analyzing financials (P&L, rent rolls, operating statements)

• Understanding fixed and variable expenses

• Negotiating deal structures and financing

• Managing teams, timelines, and vendors

• Thinking long-term about equity and yield

Those are the same skills needed to evaluate and grow a small business.

The leap isn’t as big as you think. In fact, it might be easier to manage a local service company with 5 employees than a 30,000 SF building with 10 tenants and unpredictable CapEx.

A Few Strategic Plays You Might Be Overlooking

1. Buy the Business, Keep the Real Estate
Let’s say a seller owns both the building and the business. You acquire both—but spin off the business with a lease to a new operator, locking in a long-term tenant with strong cash flow and built-in performance incentives. Or vice versa—keep the business and sell or lease the building.

2. Vertical Integration
Own a building maintenance company that services your own (and other) CRE assets. Snow removal, HVAC service, property management, janitorial services—these can all be cash-flowing businesses that support your CRE portfolio while building income.

3. Add Value Where Others Don’t See It
Many business owners are too close to their operations. As an investor, you might see opportunities to relocate, expand, restructure leases, or even franchise a proven model. You already think in terms of highest and best use—now apply that mindset to operations.

Why Business Buyers Should Think Like Real Estate Investors

The reverse is also true: If you're buying small businesses, you should be thinking about real estate.

• Does the business own the building? That’s negotiable value.

• Is there an opportunity to control the lease or lock in favorable terms? That affects your cash flow.

• Could you eventually buy the property from the landlord, creating vertical stability?

Too many buyers ignore the asset beneath the operation—and that’s where some of the biggest returns can live.

Risk Mitigation, Cash Flow, and Control

Owning real estate gives you long-term appreciation and security. Owning a business gives you immediate cash flow and operational control.

When you own both? You’ve created a stacked model:

• You can move quickly to protect your asset.

• You control both the revenue and the rent.

• You can sell one and keep the other—or scale both in tandem.

This hybrid approach is a wealth strategy more investors should be using—but few are even considering.

Final Thoughts

If you’re comfortable buying buildings, you’re closer than you think to buying businesses. You’ve already developed the mindset, the risk tolerance, and the analytical skills. What you may be missing is just the framework—and the exposure.

And if you're already buying businesses? Start paying attention to the real estate involved. Because the real power comes when you stop choosing between leases and ledgers—and learn how to leverage both.

Want to explore a deal that includes both the business and the building? Let’s talk. I specialize in helping investors structure smart, creative acquisitions that maximize both income and long-term value.