Common Mistakes Business Owners Make Before Selling

Selling a business is a huge milestone. For many owners, it’s the biggest financial event of their lifetime. But here’s the hard truth: most owners aren’t as prepared as they think they are, and the mistakes they make in the months or years before a sale can end up costing them far more than they realize.

We’ve seen it firsthand. The business is successful, the buyer is interested, the terms are decent… and then the wheels come off because something was overlooked, delayed, or misunderstood.

The good news? Most of those problems are avoidable with the right planning and advice.

Here are a few of the most common mistakes we see—and how you can sidestep them before they derail your deal or dilute your outcome.

Mistake #1: Waiting until you’re ready to sell before planning the sale

This one is so common, it almost feels baked into the process. The owner decides they’re ready—emotionally, financially, or just from sheer burnout—and then starts looking at what it would take to sell.

But by the time you're emotionally ready to exit, it's often too late to do the most meaningful tax and structural planning.

We met with a business owner just a few months before a deal was set to close. The terms were fair, the buyer was reputable, and he was excited to move on. But no planning had been done ahead of time. No trusts. No gifting. No asset segregation. No charitable strategies. The result? A much bigger tax bill than he was expecting and fewer options to manage it.

By contrast, when we work with a business owner one to three years before a sale, we can help restructure the business, separate real estate or intellectual property, clean up the books, review ownership, and implement strategies that legally reduce taxes and increase deal flexibility. Those moves don’t happen overnight, but they make a major difference when the buyer shows up.

Mistake #2: Not understanding what your business is actually worth or why

Plenty of business owners have a number in their head. Sometimes it’s grounded in industry comps. Sometimes it’s wishful thinking. And sometimes it’s based on what they need to fund the next chapter of their life.

But your business’s value isn’t just about revenue and profit. It’s about structure, systems, customer concentration, growth potential, recurring revenue, and risk mitigation.

We’ve seen businesses with similar top-line revenue sell at vastly different multiples because one had built systems, processes, and a strong team while the other was still dependent on the owner being in the room.

Getting a valuation* done early—even if you’re not selling yet—helps you identify what’s driving or dragging down your value. That knowledge gives you leverage to make smart changes while there’s still time to fix them.

Mistake #3: Ignoring your personal financial picture in the process

Selling your business isn’t just a business decision. It’s a personal one. You’re trading a familiar, cash-flowing asset for a lump sum that has to last. Yet many owners spend all their energy negotiating the deal and none thinking about what happens after it closes.

What’s your income plan post-sale? How are you investing the proceeds? What taxes will be triggered, and how much of the check will you actually keep? What’s your strategy for healthcare, lifestyle, retirement, legacy?

If you don’t know those answers, it’s time to hit pause and run the numbers.

We've seen owners realize mid-negotiation that they could’ve been investing in a defined benefit plan for years, or that a simple ownership shift to a spouse or trust could have saved substantial amounts in capital gains. But without coordination between your business team and your personal financial advisors, those strategies never get implemented.

You don’t need to have your full retirement life mapped out. But you do need a clear financial plan that works once the business isn’t paying you anymore.

Mistake #4: Assuming your CPA or attorney is handling everything

This is where deals can quietly fall apart. The CPA thinks the attorney is managing the tax angle. The attorney thinks the financial advisor is reviewing your post-sale cash flow. Everyone’s in their silo, and no one is looking at the full picture.

It’s not that your current team isn’t competent. It’s that exit planning requires coordination. Everyone needs to be at the table, asking the same questions, with a clear understanding of the outcome you’re working toward.

We’ve sat in on deal team meetings where just one good question—"What’s the plan for the real estate held inside the entity?”—led to a structural shift that improved tax treatment, reduced liability, and gave the owner more negotiating power.

When your team is working together, those opportunities show up early. When they’re not, you often find out after it’s too late.

If you’re thinking about selling, start preparing now

You don’t need to rush into a sale. But you should start preparing for one long before the offer comes in. That preparation gives you options. It gives you leverage. And it gives you peace of mind that the next chapter of your life isn’t built on last-minute decisions.

We help business owners get clear on where they stand today and where they want to be when the deal is done. That includes your business, your finances, your family, and your future.

If you're starting to think about selling or just want to understand what’s possible, let’s talk.

*Veritas Financial Partners does not provide qualified business valuations. For a qualified or certified business valuation, consult a properly credentialed appraiser.

Any discussion of taxes is for general information purposes only, does not purport to be complete or cover every situation, and should not be construed as legal, tax or accounting advice. Clients should confer with their qualified legal, tax and accounting advisors as appropriate.

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