The Top 10 Mistakes Business Owners Make When Selling Their Business (and How to Avoid Them)
- Mark Hartmann
- 4 days ago
- 7 min read
If you’re like most business owners I work with, you’ve spent years—maybe decades—building your company. You’ve sacrificed weekends, reinvested profits, and stayed up countless nights thinking about how to grow, solve problems, and support your team.
So when it comes time to sell, you want to make sure you do it right. After all, you only get one chance to sell your business—and what’s likely your biggest asset.
But here’s the thing: most owners don’t know what they don’t know.
As an M&A advisor—and as someone who’s been through my own business sale—I’ve seen firsthand the mistakes that can cost owners time, money, and peace of mind. And the worst part? Most of them are completely avoidable with the right planning and guidance.
In this post, I’ll walk you through the top 10 mistakes business owners make when selling their companies—and how you can steer clear of them so you exit on your terms, with confidence and the best possible outcome.
1. Waiting Too Long to Start Planning
This is hands down the biggest—and most common—mistake I see.
Many owners wait until they’re burned out, facing health issues, or simply “done” to start thinking about a sale. The problem? By then, they may not have the time (or energy) to prepare the business to attract the best buyers or maximize value.
What to do instead:
Start exit planning 2–3 years before you want to sell. That gives you time to clean up your financials, reduce owner dependence, increase value, and line up the right team. Even if you’re not sure when you’ll sell, having a plan in place gives you options.
2. Not Knowing What Their Business Is Really Worth
It’s amazing how many owners go into a sale with no clear idea of what their business is worth. Some rely on hearsay, industry rules of thumb, or inflated expectations. Others severely undervalue what they’ve built.
Why it matters:
If your expectations are too high, you’ll scare off good buyers. If they’re too low, you could leave millions on the table.
What to do instead:
Get a professional, market-based valuation from someone who understands your industry and the current M&A landscape. A good advisor will help you understand how buyers think and what’s driving (or hurting) value.
3. Going It Alone Without Professional Help
I get it—business owners are independent. You’ve solved problems your whole life. But selling a company isn’t like running one. It’s a complex process with major legal, financial, tax, and emotional implications.
Trying to handle it yourself—or just relying on your accountant or attorney—can lead to costly mistakes, missed opportunities, and failed deals.
What to do instead:
Build a strong advisory team:
• An M&A advisor or business broker
• An experienced transaction attorney (No, this is not your divorce lawyer Cousin!)
• A tax-savvy CPA or financial advisor
You want people who’ve done this before—and who will advocate for your best interests.
4. Failing to Prepare the Business for Sale
Would you sell your house without fixing the roof or staging the interior? Of course not. Yet many business owners try to sell with messy financials, unclear processes, or an overreliance on the owner.
Buyers notice—and it shows up in lower offers or more difficult negotiations.
What to do instead:
• Clean up your books (ideally with reviewed financials)
• Document your processes
• Build a strong management team
• Reduce owner dependence wherever possible
• Diversify your customer base and revenue streams
A well-prepared business not only commands a higher price—it makes buyers feel more confident in the future.
5. Letting Emotions Drive the Process
Selling a business is emotional. You’re not just parting with a company—you’re closing a major chapter of your life. But if emotions drive your decisions, you can end up hurting the deal.
I’ve seen owners walk away from great offers over small issues—or cling to unrealistic expectations because they’re not emotionally ready to let go.
What to do instead:
Acknowledge the emotions—but stay grounded in your goals. Having an advisor as a buffer helps. We’re here to keep the process moving forward, even when things get tough.
Also, work on defining what comes after the sale—so you’re not just stepping away from something, but stepping into something meaningful.
6. Focusing Only on the Price (and Ignoring the Terms)
The sale price gets all the attention—but the terms of the deal are just as important.
For example:
• Is it an all-cash deal, or is there an earn-out?
• Are you financing part of the deal yourself?
• What happens to working capital?
• How is the deal structured for taxes?
A $10 million offer with a 3-year earn-out and a personal guarantee might be less valuable than a $9 million all-cash deal at close.
What to do instead:
Understand the full deal structure—not just the top-line number. Work with your advisor to model out your net proceeds and evaluate the deal as a whole.
7. Not Being Honest About Risks or Weaknesses
Some owners try to “hide the bad stuff” from buyers—thinking it’ll protect the deal. But the truth is, buyers will find out during due diligence. And if they discover something you didn’t disclose, it can kill the deal—or lead to legal exposure down the road.
What to do instead:
Be transparent. It builds trust and allows you to get ahead of issues. If there’s a customer concentration problem, or a pending lawsuit, or a systems gap—let’s address it early. In many cases, we can mitigate it or adjust the deal accordingly.
8. Underestimating the Time and Energy It Takes
Selling a business takes time—often 6 to 12 months from start to finish. It also requires your involvement: providing documents, answering questions, attending meetings, and helping with the transition.
Some owners think they can sell the business in a few weeks and keep running things as usual. But deals take focus—and distractions can hurt performance, which in turn hurts value.
What to do instead:
Plan for the sale process to take real time and effort. Lean on your advisor to manage the details, but stay engaged where needed. And if possible, delegate more of your day-to-day work to your team so you’re not pulled in every direction.
9. Ignoring the Tax Implications
The sale of a business is one of the most significant financial events of your life. But too many owners go through the process without fully understanding the tax consequences—only to be shocked by their final tax bill.
What to do instead:
Get proactive tax planning before you go to market. Your tax advisor can help you:
• Understand capital gains vs. ordinary income treatment
• Structure the deal to minimize tax burden
• Use strategies like trusts, rollovers, or charitable giving to preserve wealth
A well-structured deal can save you hundreds of thousands—or even millions—in taxes.
10. Failing to Define What's Next
One of the saddest things I see is when a business owner finally closes the deal… and then feels lost.
They didn’t think through what came next—so they struggle with identity, purpose, and direction. It’s especially common with owners who built their business from scratch and were deeply involved for decades.
What to do instead:
Spend time defining your post-sale vision. That might include:
• Traveling or spending time with family
• Starting a new business, nonprofit, or investment venture
• Mentoring other entrepreneurs
• Pursuing hobbies, volunteering, or teaching
A clear “next chapter” gives meaning to your exit—and makes the whole journey more rewarding.
Final Thoughts: Avoiding These Mistakes Starts with the Right Guide
Look, selling a business isn’t something you do every day. For most owners, it’s a once-in-a-lifetime event. And the stakes are high.
That’s why you don’t need to know everything—but you do need someone in your corner who does.
At HartmannRhodes, I work with business owners just like you—especially those 60 and older who are preparing for retirement and want to exit their business the right way. I’ve walked this path myself, and I bring that firsthand experience to every client relationship.
Whether you’re thinking about selling in the next few months or a few years down the road, I’d be happy to help you get prepared—and avoid these common mistakes.
Because you spent decades building your business. Now it’s time to transition on your terms, with expert guidance, a clear plan, and the best possible outcome.
Thinking about selling your business? Let’s have a confidential conversation.
👉 Contact me today and let’s talk about your goals, your timeline, and how to avoid the pitfalls so you can exit with confidence.
Blog: The Top 10 Mistakes Business Owners Make When Selling Their Business (and How to Avoid Them)
Mark Hartmann is a former business owner turned M&A advisor who knows firsthand what it takes to build, grow, and sell a successful company. A three-time Inc. 5000 CEO, Mark did just that before navigating its eight-figure sale—giving him a rare perspective that sets him apart from most brokers. Today, he helps owners of companies valued between $1M and $25M plan and execute smooth, profitable exits.
Mark understands that selling a business isn’t just a financial decision—it’s personal. That’s why he works closely with owners to protect their legacy, maximize value, and make the transition on their terms. He holds an MBA from Eastern University, a Master’s Degree in Organizational Change Management from St. Elizabeth University, and a Graduate Certificate in Executive Coaching from Columbia University. Some of his professional credentials include Certified Mergers & Acquisitions Professional (CM&AP), Certified Business Intermediary (CBI), Certified Exit Planning Advisor (CEPA), and Certified Value Builder (CVB).
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Morristown, NJ 07960
Partner with HartmannRhodes, expert business brokers and M&A advisors, to navigate your business sale with precision—maximizing value and ensuring a smooth transition. Reach out for tailored business sale strategies. Contact us today!
