Introduction
When a business owner asked, “When should I expect the unexpected?” Keith Dee of Osage Advisors paused, then smiled. After 25 years in M&A, his answer was simple: at every single stage.
In a recent episode of The Ins and Outs of Selling a Business, Keith Dee broke down the surprises owners face before, during, and even after the sale of their business and why preparation is the key to staying calm when the unexpected hits.
The First Hurdle: Family Expectations
Many sellers assume their children will want to take over the business. But one of the most emotional (and common) surprises is learning they don’t.
Some family members may love working in the business but have no desire to lead it. Others don’t want the risk, the stress, or the responsibility.
This realization can be hard, but it often leads owners to consider selling to an outside buyer, which opens a new set of decisions including how to structure the deal to meet both personal and financial goals.
Understanding Value Expectations
Another early surprise is discovering what your company is actually worth. Many owners come in with a number in mind, often influenced by what a peer sold for, but without understanding how the market truly values their business.
Keith explains that Osage always starts with a current market valuation assessment. It’s not a certified appraisal, but a real-world view based on market trends, buyer behavior, and deal comps.
“You may think your business is worth $20 million,” Keith says, “but the market might value it at $12–15 million based on your industry, growth, and margins.”
Get Your House in Order
The first stage of the sale is full of surprises, but many are preventable with the right prep.
Key areas that cause unexpected issues:
- Incomplete or inaccurate inventory records
- Missing or outdated corporate documents
- Lingering liens from old loans
- Weak financial systems or non-audited books
A pre-sale financial and legal review by your CPA/Attorney can save time, stress, and money later in the process.
The Curveballs During the Sale
Even when a deal is in motion, surprises still surface.
Supply chain issues, tariff changes, delayed customer orders, all of these can cause buyers to pause or restructure the deal. Keith shares one story where a major customer delayed an order by six months right before closing. The team had to get creative and introduce an earnout structure to bridge the gap.
Another common issue: buyers who go quiet. Whether it’s due to financing, internal uncertainty, or partner backing out, sellers should be prepared for things to stall and definitely have contingency plans in place.
Final Thoughts
The sale of a business is complex and emotional, and no matter how prepared you are, something unexpected will come up.
But with the right advisors, the right preparation, and the right mindset, you can navigate those moments without derailing the deal.
“We always say it’s about patience,” Keith says. “If the deal’s right, it will get done. And if it’s not, the right one is still out there.”
Certain Members of Osage Advisors are Registered Representatives of and conduct securities transactions through StillPoint Capital, LLC, Tampa, FL. Osage and StillPoint are not affiliated.
Osage Advisors provides a lot of guidance in the M&A market here on our blog and on our YouTube channel and Podcast.
