Pass the Tissues: The Emotional Side of Selling Your Small Business

I love when a good movie or novel takes me to a place where I’ve never been or puts me in a situation which I’ve never experienced – like jumping from cliffs, or leaping off buildings – and hopefully, never will! But I still want to know: What’s it like? What happens next?

The latest episode of “Sunny’s Silver Linings” podcast does just that. It features Jamison West, an author, serial entrepreneur, strategic coach at ConnectStrat, and a former MSP owner who built a successful business and then sold it. He documented it in a self-published book, “The Emotional Side of Selling a Small Business”. So his story isn’t just about the “nuts and bolts” of the selling process; rather, it focuses on the emotional rollercoaster that he went through during this first-time journey.

Now that’s a compelling angle on a story that could’ve been a bland textbook on selling a business!

Before he sold his MSP, Jamison had gone through a tumultuous set of four acquisitions which exhausted him and made him realize that he needed a career change. He decided to sell his MSP, but when he went to do some homework, he found a lot of literature, books, and resources around financial metrics, valuations, Mergers & Acquisitions advisories, etc. But nothing prepared him for the emotional turmoil, the ups-and-downs.

“It was very challenging for me,” Jamison said. “After the sale, I started asking others who had been through the same experience and found that my journey was not unique. They struggled through the same experiences without resources.”

In the podcast, he candidly talks about how by putting 20 to 30 years of your life into a business it becomes your identity. Then, when you sell it, you’re selling off your identity as well as the business itself. This could be a drastic change for some who might not be emotionally ready for it.

Thus, the idea for the book. It takes readers on the complete journey – from the moment Jamison realized that he could sell the business and make money to the final transaction. It includes all of the struggles that it took to get his business sold. For instance, he recounts the emotional side of having to proceed with the sales process but he couldn’t tell his team – some of whom he was very close to.

“Once you start walking down this [sales] path, there’s a high level of confidentiality and non-disclosure. So you can’t tell your entire team that you’re thinking about selling the business but it might not happen. But once you sign that letter of intent, you stop making decisions that could cost the business money,” Jamison said.

His open door policy changed when his office door was closed for confidential phone conversations. He would have to ask some of his team members to handle some tasks or prepare paperwork but couldn’t tell them why.

“So from an integrity perspective, it was extremely challenging. I cared for my team – some were my close friends,” he noted. “There was no intention to lie, but I was withholding truths. And that’s not a habit of mine.”

Eventually he had to decide – and some said it was a poor decision – to begin informing key members of his approximately 25-member team and then the entire team before the transaction was complete.

“That’s a dangerous point to be because now you’re completely committed,” he said. “Not just emotionally but now I put my entire business at risk because, if the transaction doesn’t go through, I’ve exposed my willingness to sell and could garner a tremendous backlash should the sale not go through.”

According to Jamison, the response from the team depended on the individual and individuals’ longevity at the company. Some who had some equity in the business were excited, while others thought their jobs were at risk and were extraordinarily fearful. He did lose some key members around the transaction time, for which he takes the blame.

But once that hurdle passed, he said it was such a relief “that the burden of secrecy was no longer on my shoulders.”

He offered three pieces of advice to MSP owners who are about to sell their businesses:

• Read his book because he created it when he found that there were very limited helpful resources available to prepare him for the emotional aspects when he began his journey.
• Be very clear on what your non-negotiables are. With this, you won’t emotionally commit and allow a prospective buyer to chip away at your non-negotiables until you’ve found yourself in a financial position that’s vastly less than what you’d expected or hoped for when you first began the journey.
• Consult articles on Harvard Business Review that cover the pre-sale aspects of selling your MSP and some that address the post-sale aspect with an entrepreneurial mindset.

He warns that those who believe that they can sell a small business and then just retire might be in for a big surprise because that financial number may not be the number they need.

The book, “The Emotional Side of Selling a Small Business”, is available on Amazon or visit his website at jamisonwest.com and includes the experiences of others – six case studies – who took the same journey.

Click here to listen to the entire podcast.