Selling Your Business: What Nobody Tells You About Letting Go

Episode 224 

Released January 8, 2026

This week I’m joined by James Gardner, a fellow Vistage member who’s been on quite a journey – from building a manufacturing business with his brother over nearly two decades, through its sale, to running a funeral director businesses in Kent. James now mentors business owners through acquisitions, post-acquisition challenges, and the transition out of businesses.

What struck me most was James’s honesty about the emotional reality of selling a business. We hear the success stories – the champagne corks, the celebration – but rarely what comes next.

James opens up about what he describes as the worst 18 months of his life, despite having more money in the bank than ever before.

From Dressing Table to International Business

James’s story begins around 2000, when his brother spotted a gap in the market. His first few days in business were spent at his sister-in-law’s dressing table with a laptop and a fax machine. From there, they moved to a leaky farm building, then a garden shed they’d insulated themselves.

They grew internationally, with James flying to their US operation 13 times in one year. These things sound glamorous but really aren’t, he reflects – time away from family, friends, and other opportunities. But they worked hard, treated people well, and delivered on every promise.

The Sale – and What Came After

When the right buyer came along – one who could preserve jobs and accelerate their plans – the brothers took the leap. They were lucky to be on the same page; family partnerships often break down.

James stayed on after the sale through a gentleman’s agreement. Senior positions were promised. The reality didn’t match the brochure.

The first 6 to 18 months were the unhappiest of his life. He had more money than ever, yet felt imprisoned. The golden handcuffs, as he calls them – yes, they’re gold, but you’re still handcuffed.

What resonated with me was his reflection on control. When you’ve built something, oversight and strategy flow through you. Then suddenly, that stops. You may be mentally ready to hand over, but are you emotionally prepared? As James put it: ‘You’re literally handing your baby over to somebody else to raise, whilst you’re still in the room.’

Rolling the Dice Again

Things eventually improved, and James went on to run the larger UK department. But he asked himself: do I want to do this for another 25 years, or roll the dice?

In 2019, he chose to move on. Wanting something recession-proof, he remembered working as a trainee funeral director years earlier and approached that same business owner. Ten days after signing in March 2020, the country went into lockdown. He now runs four funeral directors in Kent.

Key Insights

It’s people, people, people.

Treat your team well first. Then your customers. Then – and this often gets forgotten – your suppliers. When something goes wrong, you want to be at the top of their list.

Plan your exit properly.

A short handover works better than staying on indefinitely. And if you don’t have a plan for life after the sale, the sudden absence of purpose can be devastating.

Communication is everything.

The root cause of most relationship breakdowns is communication. Having someone in your corner to sound-check decisions is invaluable.

Connect with James

James now mentors business owners through acquisitions, post-acquisition challenges, and the transition out of businesses.

• Website: amazing3dgoals.com (that’s the number 3)

• LinkedIn: James Gardner

• Youtube: Amazing Leaders

   

James’s story reminds us that business people are not immune. We have highbrow ideas about building something, but we’re not always ready to let it go. The sale can look like the ultimate success, but the emotional journey is far more complex than the financial transaction.

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