INTRODUCTION

Selling a business is rarely a straight line. Even with the best planning, surprises come up, often at the worst possible moments. In a recent episode of The Ins and Outs of Selling a Business, Keith Dee, President of Osage Advisors, continues the conversation about the unexpected events that can unfold at every stage of an M&A deal.

From shifting emotions to legal hurdles, environmental issues, or team changes, Keith outlines what sellers should be aware of and how to prepare for the unexpected.

UNEXPECTED MOMENTS CAN HAPPEN ANYTIME
Buyers, sellers, and advisors all bring different personalities and emotions to the table. We break the process into four distinct phases—each with its own potential curveballs:

• Before the Sale: You may discover your business isn’t worth what you expected, or a family member decides they do want to be involved after all.
• During the Sale: A buyer who looked great on paper might give off red flags in person.
• Due Diligence and Closing: Environmental issues, document delays, or leadership concerns can slow things down—or derail a deal entirely.
• Post-Closing: You might face working capital adjustments, rework costs, or earnout issues that catch you off guard.

COMMON SCENARIOS THAT CATCH SELLERS OFF GUARD

• You meet a high-bidding buyer who just doesn’t feel right.
• A partner or family member changes their mind about selling—after you’ve signed a letter of intent.
• A successor you’ve trained for years doesn’t instill confidence in the buyer.
• Due diligence uncovers old environmental issues or unexpected financial red flags.
• You thought you’d be out of the business in six months—but the buyer asks you to stay for two years.

All of these can throw a wrench in your plans and require careful, level-headed decision-making.

THE BEST WAY TO HANDLE THE UNEXPECTED

The good news is, you don’t have to go it alone. Having the right team (think investment banker, M&A attorney and accountant) is critical. So is being mentally prepared for the emotional side of the sale. Doubts, cold feet, and last-minute surprises are all normal. Your team is also there to help you manage these emotions and potential surprises.

At Osage, we work shoulder-to-shoulder with clients through every stage of the deal, helping them navigate complexity, mitigate risk, and make informed decisions.

FINAL THOUGHTS

Unexpected issues will arise. What matters most is how you handle them. With the right mindset and experienced advisors at your side, you can work through challenges and complete a successful transaction—on your terms and for the benefit of your family and your future.

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.