Build It Like You'll Sell It Tomorrow

By Brian Eder

Business owners don't want advice from someone who has only ever advised. They want it from someone who has been in the room when payroll was tight, when a buyer went cold, when the number came in lower than expected.

It's like taking business advice from a professor who has only ever taught. The theory is sound, but the scar tissue is missing.

That gap matters more than most advisors acknowledge.

The business owners most likely to leave money on the table are not the ones with bad companies. They are the ones whose advisors got involved too late or could not speak to the owner's experience from the inside.

Here is what that costs them.

Private markets are not efficient. Maximizing price often means being opportunistic, moving when the timing, the buyer and the terms align. Owners who command the strongest exits are not always the ones who planned to sell. They are the ones who built a business that could sell at any moment. That kind of readiness does not happen by accident, and it does not happen without an advisor who understands what it actually takes to build something.

Once a serious buyer calls, preparation becomes visible fast. Financial reporting may not be organized the way institutional buyers expect. The company may depend too heavily on the founder. In many cases, the owner has not considered what happens after the sale, financially or personally.

That lack of preparation is expensive, not just at the closing table, but in the years preceding it.

Roughly 80% to 90% of a business owner's net worth is tied up in the business itself, yet many owners approach a sale without a formal transition strategy. Additional research suggests many privately held businesses that go to market never actually sell. Often it is not because the company lacks value, but because the owner was not ready for the scrutiny that comes with a serious transaction.

The most productive planning conversations happen 12 to 18 months before a sale, not after the letter of intent is signed. Tax strategies involving trusts, charitable giving, ownership structure and estate planning need to be in place long before a transaction begins. Once the process is underway, many of those opportunities are gone. Being generous at a restaurant is one thing. Tipping the IRS is another. Tax mitigation is not an afterthought in a well-planned exit. It's the difference between a good outcome and a great one.

Then there's the personal side, which advisors consistently underestimate. Most owners spend more time preparing the company for sale than preparing themselves for what comes next.

Selling a business is not just a financial transaction; for many founders, it represents a significant shift in identity, purpose and daily routine. The most effective advisors recognize that transition planning extends beyond taxes, valuations and deal structures. Questions about legacy, family dynamics, philanthropy and life after ownership often prove just as important as the sale itself.

The hardest question is rarely, “What is the business worth?” It is, “Who am I after the business is gone?”

Owners who start planning earlier have more options, more leverage and more control over the outcome. That preparation is what separates a decent exit from a successful one.