A Costly Mistake: I Can Sell My Business on My Own
Over the course of my career, I have worked with businesses of all sizes—small, medium, and large—at various stages of growth, profitability, and readiness for transition.
When it comes time to sell a business, I typically see one of three situations:
1. The business isn't ready.
2. The owner isn't ready.
3. The business is successful, attractive, and buyers are already expressing interest.
Today, I'd like to focus on the third scenario where some owners in this position believe:
• I can sell my business myself.
• I already have buyers interested.
• Why would I pay an advisor when the buyer is already at the door?
It's an understandable perspective. After all, having interested buyers is a great problem to have. However, having buyers and achieving the best outcome are not necessarily the same thing.
A Costly Lesson
A good friend was ready to sell a successful 30-year-old company. What followed became a valuable and frustrating lesson about selling a company.
I knew the business well – it was profitable year over year, established an excellent brand, carried no debt, owned real estate, had a strong management team, and attracted interest from a strategic buyer.
At the same time, the second generation of the family wanted to purchase the company. They knew the business well, had worked in it for years, lived in the community, and had secured financing to complete the transaction. Surprisingly, the owner would not consider the family option. Knowing the second generation myself, I thought they would be a good fit, and what a wonderful way to continue the legacy.
In addition, my friend chose not to engage an M&A advisor or retain specialized M&A legal counsel. He relied on a trusted lawyer and local accounting firm who were capable professionals but did not regularly work on business transactions of this complexity.
I’m not an M&A advisor myself, but I’ve worked alongside them for years to understand the value they bring to the table. As both a friend and advisor, I found myself in a difficult position. I raised my concerns and suggested M&A professionals to help.
But there is a fine line between providing advice and creating friction. At some point, owners have the right to make their own decisions, even when we disagree with them. Because he was a friend, I didn't want to damage the relationship by repeatedly pushing an issue he had clearly made up his mind about.
So, I stepped back and unfortunately, the concerns I had at the outset gradually became reality.
The buyer's CFO came from a private equity background and was highly experienced in acquisitions. Negotiations stretched on for more than a year. Discussions around normalized EBITDA, working capital adjustments, and deal structure became increasingly complex. What should have been an exciting transition became exhausting.
Watching from the sidelines was difficult. Not because I wanted to be right, but because I could see the toll the process was taking and knew that experienced transaction advisors could have helped level the playing field.
Eventually, fatigue set in. After more than a year of negotiations, endless requests, and constant discussions around financial adjustments, my friend simply wanted the process to end. The company sold for approximately 3x EBITDA, despite transactions in the sector often occurring at significantly higher multiples. To put this into perspective, on a business generating $5 million of EBITDA, a difference of just one turn of EBITDA can represent $5 million of value. Whether the gap was one turn, two turns, or something else, the dollars involved could be significant.
Would an M&A advisor have guaranteed a better outcome? There’s no guarantee, but experienced advisors bring market knowledge, transaction expertise, negotiating leverage, and process discipline. They help owners avoid learning transaction lessons in real time while with money at stake.
Looking back, the experience reinforced something I have seen repeatedly: selling a business is not just about finding a buyer. It is about having the right people around the table when one of the most important financial decisions of your life is being made.
What Owners Often Underestimate
Many owners believe the hardest part of selling a business is finding a buyer. Partly true, but in reality the hardest part is often:
• Determining the true market value of the business
• Creating competitive tension among buyers
• Managing due diligence
• Structuring the deal
• Negotiating terms beyond price
• Protecting confidential information
• Managing tax implications
• Maintaining business performance during the sale process
• Keeping emotions from influencing decisions
• Successfully getting the transaction across the finish line
Benefits of an M&A Advisor
• Establish a realistic valuation range
• Identify and approach additional qualified buyers
• Create competitive bidding tension
• Prepare marketing materials and financial presentations
• Manage the sale process and timelines
• Coordinate lawyers, accountants, tax advisors, and lenders
• Negotiate key deal terms
• Help defend value during due diligence
• Reduce deal fatigue
• Allow the owner to focus on running the business
Risks of Going It Alone
• Lower valuation
• Fewer buyer options
• Weak negotiating position
• Excessive concessions during due diligence
• Poor deal structure
• Unexpected tax consequences
• Confidentiality breaches
• Longer timelines
• Deal fatigue
• Increased likelihood of a failed transaction
Final Thought
If your business is successful and buyers are already knocking on the door, congratulations—you've built something valuable. But do not confuse having a buyer with having a competitive sale process.
For most owners, selling their business is the largest financial transaction of their lifetime. The question isn't whether you can sell the business yourself. The question is whether you can achieve the best outcome for yourself, your family, your employees, and your legacy.