If you’ve spent any time thinking about buying or selling a business, you already know—it’s not just a transaction. It’s one of the biggest financial and personal decisions you’ll ever make.
I’ve been in this space a long time, and I can tell you this: what most people think matters in a deal usually isn’t what actually drives the outcome.
Let’s walk through a few realities that don’t always get talked about—but should.
The Timing Mistake Almost Every Owner Makes
Most business owners wait too long to sell. It’s that simple.
They tell themselves they’ll exit when they’re “ready,” when things slow down, or when they’ve squeezed out just a little more profit. The problem is buyers don’t pay for what was—they pay for what’s next.
Momentum is what drives value.
If your business is performing well right now, that’s not a reason to hold—it’s a reason to start planning. The best exits happen when buyers can clearly see growth ahead of them, not behind them.
And here’s the part many miss: if you think you might want to sell in the next couple of years, the work starts now. Preparation isn’t optional if you want a strong outcome.
Why Buying a Business Is Often the Smarter Move
There’s a reason more experienced entrepreneurs look to acquisition instead of starting from scratch.
Starting a business sounds appealing—until you factor in the failure rate. A large percentage of new businesses don’t make it past the first few years. That’s not pessimism, it’s reality.
When you buy an existing business, you’re stepping into something that already works:
- Revenue is already coming in
- Customers are already there
- Systems are already in place
You’re not guessing—you’re building on a foundation.
What I see often is new owners bringing fresh energy and ideas into a business that’s already stable. That combination can unlock growth much faster than starting from zero.
The 10-Year Seller Note Trap
This is one of the biggest risks sellers walk into without fully understanding it.
In many deals—especially those involving SBA financing—there’s a seller note involved. That means the seller is effectively financing part of the purchase price.
Sounds reasonable, right?
Here’s where it gets complicated.
If that note is used as part of the buyer’s down payment, SBA rules can require what’s called a full standby. In plain terms, that means the seller doesn’t receive payments—principal or interest—for the entire life of the loan. That can be 10 years.
Ten years without seeing a dollar.
Even in cases where the note isn’t part of the down payment, lenders can still impose standby requirements depending on how the deal is structured and whether the business can support the debt.
And then there’s subordination—where the bank gets paid first if anything goes wrong. The seller is last in line.
This is why deal structure matters just as much as price. If you’re not careful, you can “sell” your business and still be financially tied to it for a decade with significant risk.
Why a Small Seller Note Can Actually Help
Now, that doesn’t mean seller notes are bad across the board.
In fact, a small seller note—typically around 10%—can be a powerful tool when used correctly.
It shows the buyer that you believe in the business. That confidence goes a long way.
More importantly, it keeps you engaged during the transition. Deals don’t succeed or fail on paper—they succeed or fail in the handoff. Customer relationships, employee trust, operational knowledge… those don’t transfer automatically.
When you have a small stake in the outcome, you’re more likely to stay involved and help the buyer succeed. That benefits everyone.
Bridging the Gap: When Price Expectations Don’t Align
One of the most common challenges in a deal is the gap between what a seller wants and what a buyer is willing to pay.
This is where creative structuring comes into play.
A performance-based component—sometimes called a forgivable note or earn-out—can bridge that gap.
For example:
- Part of the purchase price is tied to hitting revenue targets
- Or tied to retaining key employees
- Or tied to performance in the first year or two
If the business performs as expected, the seller gets the full value. If it doesn’t, the buyer is protected.
It’s a practical way to align expectations without killing the deal.
There Are No Do-Overs
This is the part I always come back to.
You only get one chance to structure this correctly.
Once the deal is done, the terms are set. If there are gaps, risks, or missed opportunities—they don’t get fixed later.
Whether you’re buying or selling, the goal isn’t just to get to the closing table. The goal is to get there with a structure that protects you, supports the transition, and sets both sides up for success.
Because at the end of the day, the question isn’t just:
“Did you get the deal done?”
It’s:
“Did you get the deal done right?”