Why Price Is The Wrong Metric When Selling Your Business.

When business owners think about selling, the first question is almost always the same:

“What’s my business worth?”

That’s the right starting point, but it’s not the whole story.

Because in a sale, headline price is not the same as what you keep. A “great price” can turn into a disappointing outcome if the deal structure and tax plan are treated as an afterthought.

Price vs. Proceeds: The Most Common Exit Mistake

Two deals can offer the same purchase price and deliver very different outcomes because of:

• How the deal is structured (asset sale vs. stock sale, recap vs. full exit)
• What you receive (cash now vs. rollover equity vs. earnout)
• When you receive it (upfront vs. over time)
• What gets taxed and how (capital gains vs. ordinary income)
• What risks you keep (escrows, holdbacks, reps & warranties, working capital)

Owners don’t lose value only because of the multiple.

They lose value because the process focuses on price and ignores proceeds until it’s too late.

Why This Happens

Most owners only sell once. The process is unfamiliar. And it’s easy to assume:

“We’ll figure taxes out at the end.”

But by the time you sign an LOI, you’ve usually already made choices that drive your after-tax outcome, including:

• transaction form
• consideration mix (cash vs. equity vs. earnout)
• timing of payments
• purchase price allocation mechanics
• working capital and holdback structures

At that point, changing structure can be hard, and costly.

Our Philosophy: Plan Early, Negotiate From Strength

At C&A Dealmakers, we integrate tax-aware planning early so owners can make informed decisions before the process locks them in.

Here’s what that looks like in practice.

1) Evaluate Entity and Deal Structure Implications Early

Different entity types and ownership structures can lead to very different outcomes in a sale.

When we plan early, we can help you understand:

• what structures are feasible
• what buyers are likely to push for
• what decisions should be made before going to market
• what “clean up” work can reduce friction during diligence

This isn't about “tax tricks”, it's about avoiding unforced errors and staying in control of the process.

And, let's not forget, the One Big Beautiful Bill has changed the game. With planning and patience, it is possible to sell your business and pay ZERO capital gains.

2) Reduce Avoidable “Exit Tax Rate” Leakage

The sale price is only one part of your outcome.

Your real outcome is: After-tax proceeds = price – taxes – fees – value lost through structure and terms.

Owners often experience “leakage” when:

• diligence issues change the structure late in the process
• earnouts/holdbacks shift timing and risk back to the seller
• allocations create more ordinary-income treatment than expected
• decisions are made under deadline pressure instead of planning

Preparation reduces surprises. Fewer surprises means less re-trading and better terms.

3) Coordinate Wealth and Estate Planning in Parallel

Owners often decide mid-process that they want to:

• align the exit with estate goals
• plan for family, philanthropy, or legacy
• structure proceeds for long-term wealth strategy

Those moves can be powerful, but they require time and clean execution.

When planning happens in parallel with the transaction timeline, you’re not forced into last-minute decisions.

What This Means for You as an Owner

If you’re thinking about a sale, the goal isn’t just to “get a great offer.”

The goal is to create an outcome that protects:

• value
• terms
• certainty of close
• after-tax proceeds

That’s what sell-side advisory is designed to do.

The Best First Step: Know Your Value (and What Drives It)

Before you decide whether or how to sell, you need clarity on:

• what your business is worth today
• what buyers will pressure-test
• what you can do now to improve value and reduce risk
• what deal structures could impact your after-tax proceeds

That’s why we offer a no-cost, no-obligation estimate of business value.

It’s confidential, practical, and designed to help you get oriented, without pressure.