Selling a Business: One Man’s Journey
17 November 2025: Selling a Business: One Man’s Journey
The following story is true, though names have been changed.
I had input from others in writing this post. I do not personally know the individual described but have known of him and his business – the subject of this story – for many years. His story captures a great deal of what any business owner goes through but, unlike many such owners, this man understood and prepared for many of the aspects of selling a business that often trip up so many sellers.
This seller, an entrepreneur who I’ve given the pseudonym “Wilson”, started his business about 20 years ago. He deliberately built his business with an exit in mind.
As happened to me at about that same time, he was approached by a buyer that had a relationship with his business. How he decided to proceed once discussions started is a text book example of how to prepare for his exit and structure what ultimately became a successful
From Owner to Seller: The Abridged Version
In the fast-paced world of entrepreneurship, staying vigilant and adaptable is crucial for success. This lesson was not lost on Wilson, who, over the years, learned to navigate both the triumphs and challenges of building and selling a business. His story serves as a valuable guide for entrepreneurs looking to recognize when to pivot toward an exit, and manage the emotional and financial complexities that come with selling their business.
__________________________________________________________________________________
Check out our new YouTube channel on how to value, price and sell a business.
Business owners, buyers, brokers, consultants and even real estate agents…resources – including courses, coaching and all the talents needed for selling a business – are available in The Brokers Roundtable℠
___________________________________________________________________________________
Knowing When to Exit
Wilson had always prided himself on staying attuned to the market. He recognized the importance of keeping a pulse on industry trends and consumer behavior. Over time, however, he began to sense that his company was starting to coast. There were no new challenges, no exciting growth opportunities—only routine. This feeling of stagnation raised a red flag for Wilson. In fast-evolving industries, complacency can quickly lead to decline. Whether it’s the market or the owner’s engagement, if business growth is plateauing, it may be time to reassess.
The key lesson here, he believed, is to regularly assess both the company’s trajectory and the owner’s passion. If either of these begins to wane, it might be time to consider exiting the business.
Wilson’s decision to sell his company wasn’t driven by the hope of finding a “perfect” offer. Instead, he acted on a timely, solid opportunity that aligned with his business’s current growth potential. He advises other founders to not reject good offers while waiting for an elusive, better one that may never materialize. Timing is everything, and knowing when to move on is critical to ensuring that the business doesn’t enter a period of irreversible decline.
The Emotional and Practical Challenges of Selling
Selling a business is often described as both a financial and an emotional process. Wilson’s experience in navigating the sale of his company highlighted just how difficult this transition can be.
The due diligence phase was one of the most challenging aspects of the process for Wilson. It often felt like the company he had worked so hard to build was being scrutinized too deeply. Founders can take the due diligence process personally, but Wilson emphasized that the scrutiny is not about you as a person—it’s about ensuring that the business is in good shape for the new owners.
Wilson stressed the importance of trusting legal and financial advisors during this phase. Rather than micromanaging every detail, owners should focus on the big picture – running the business – and let their experts handle the intricacies of deal structure. Having a trusted team in place helps the process move more smoothly and ensures that the owner’s interests are well protected.
An important aspect of Wilson’s sale was the structure of the earn-out. He carefully negotiated terms based on measurable metrics like revenue, customer growth, and continuity of service. By making sure that progress was easy to track, Wilson could clearly understand how well the business was performing post-sale. The earn-out agreement allowed him to stay involved in a limited capacity, ensuring that the transition to new ownership was as seamless as possible.
This Post is Sponsored By Deal Memo, a provider of Confidential Information Memoranda For Business Brokers and M&A Specialists
The hardest part of the sale, however, was coming to terms with the reality that the business was no longer his. Letting go of something he had poured so much energy into was difficult, but Wilson knew that this was a natural part of the process. He advises founders to prepare emotionally for this shift just as carefully as they would prepare financially. Having a plan for what’s next—whether that’s a new venture, a sabbatical, or pursuing a personal passion—helps provide direction after the sale and ensures that the founder doesn’t feel lost once the deal is done.
Seller Involvement and Buyer Control
When selling a company, one of the key concerns is often whether the business can continue to thrive without the seller – often its founder – at the helm. Buyers typically look for businesses that can function independently, but at the same time, seller or founder involvement is often crucial for maintaining the company’s vision, quality, and culture. Wilson found a balance between staying involved and giving the company the space it needed to grow under new ownership.
He advocated for building systems and teams that could operate autonomously, while still allowing him to nurture and protect the brand. This can be critical, especially if the company carries the founder’s name. This balance between oversight and autonomy was key to ensuring the company’s future success while also making the transition easier for both him and the buyer. Even if it was only a few hours a day of involvement, Wilson found that staying engaged allowed him to maintain the company’s standards while allowing the new owners to implement their vision.
Another important lesson Wilson shares is that business owners must know when to step back. If a owner is unable to emotionally detach from the business, it may not be the right time to sell. Preparing for a reduced role, documenting systems thoroughly, and gradually delegating daily responsibilities can help ensure a smooth transition. This also reassures potential buyers, who are more likely to invest in a business that operates efficiently without the owner’s constant oversight.
Life After the Business
One of the major challenges many entrepreneurs face when selling their business is the sense of loss they feel when their identity is closely tied to the company. Wilson avoided this trap by cultivating an independent personal “brand” that extended far beyond his business. He was active in sharing his personal interests—skydiving, travel, public speaking, and more—outside the business which allowed him to create a strong personal identity that was not solely tied to his company.
_____________________________________________________________________________________
REALTORS! Our course, “Learn How to Value and SUCCESSFULLY Sell Businesses“, teaches you how to accurately value and successfully sell businesses.
Don’t Miss Out on the “Silver Tsunami”!
By involving himself in outside interests long before the sale of his business, Wilson set himself up for success in the next phase of his career. His personal interests opened doors to new opportunities in consulting, speaking engagements, and other ventures that aligned with his passions and expertise. The key takeaway from Wilson’s experience is that owners should begin building on their outside interests early, long before they decide to sell their company. This way, they are already known for their broader contributions and not just for their business.
What Owners Can Learn
Wilson’s journey provides valuable insights for owners considering the sale of their business. Some key takeaways include:
- Regularly assess your engagement and market position: Recognize when your passion or the business’s potential is beginning to fade.
- Don’t hold out for a perfect offer: “Perfect” offers don’t exist. Take advantage of great opportunities when they arise.
- Prepare emotionally for due diligence and post-sale transition: Letting go is tough, but preparing for the emotional shift is just as important as the financial aspects.
- Systematize your business: Build teams, processes, and systems that can run the business independently while maintaining your oversight.
- Build a personal brand that transcends your business: Cultivate a strong, visible personal brand that will open doors to new opportunities after your business exit.
The Bottom Line
Wilson’s experience offers a comprehensive roadmap for business owner who are looking to sell their business. His story emphasizes the importance of awareness, preparation, and emotional resilience, as well as the value of maintaining a broader identity beyond the company. Selling a business is not just a financial transaction—it’s a personal journey that requires careful thought and planning for both the business and the owner’s future.
Interested in learning what a business is worth? Check out our video series, “How Much is My Business Worth“on our YouTube channel.
“Success is not the key to happiness. Happiness is the key to success. If you love what you are doing, you will be successful.“
– Albert Schweitzer
If you have any questions or comments on this topic – or any topic related to business – I’d like to hear from you. Put them in the comments box below. Start the conversation and I’ll get back to you with answers or my own comments. If I get enough on one topic, I’ll address them in a future post or podcast.
I’ll be back with you again next Monday. In the meantime, I hope you have a safe and profitable week.
Joe
Searching For…
A NOTE TO READERS: Our “Searching For…” feature has been moved to our online support platform, The Brokers Roundtable℠. It will appear there exclusively.
#business #businessacquisition #sellabusiness #becomeabusinessbroker #businessbrokering #businessvaluation #MergersandAcquisitions #buyabusiness #sellabusiness #realtor #realestateagents #Worldwide Business Brokers,
The author is the founder, in 2001, of Worldwide Business Brokers and holds a certification from the International Business Brokers Association (IBBA) as a Certified Business Intermediary (CBI) of which there are fewer than 1,000 in the world. He can be reached at jo*@*******************og.com