It’s easy to get caught up in the ideal version of selling a business. You find the perfect buyer, complete a smooth handover, then walk away with a healthy payout before retiring to the Bahamas.
Real life doesn’t always unfold that neatly. Selling a business takes time: there’s due diligence to work through, accountants to hire, and contracts to carefully review. None of those things are particularly glamorous, but they’re important. Selling at the wrong time, for the wrong price, or to the wrong buyer can end up being an expensive mistake.
That’s exactly what happened to Rachel Jesson, a South African entrepreneur who sold a family business through BusinessesForSale.com. In this candid story, she explains what went wrong during the sale – and shares some practical advice for other business owners preparing to sell. She also reveals how she eventually rebuilt the business and achieved a much better outcome the second time around.
Tip: If you're thinking about selling your business, you can create a listing on BusinessesForSale.com and test the market for free.
Selling the Business from Overseas
Rachel inherited an events and catering business called Kate’s Party Rentals from her late mother, who founded the company in 1989. It was a long-established business with loyal clients, and Rachel operated it for more than twenty years. But after she and her partner started a family, they decided to relocate from South Africa to the UK. Selling the business became the next logical step.
Rachel wasn’t able to secure a buyer before the move date, meaning much of the sales process had to be managed remotely. That made due diligence far more challenging and meant she never had the opportunity to meet the buyer face-to-face before the deal was completed.
She chose to structure the deal using seller financing, where part of the purchase price would be paid through the future profits of the business. Seller financing can appeal to buyers because it often reduces the amount of third-party funding needed upfront – but it also carries risk for sellers. The business still needs to remain profitable enough to cover the agreed payments, despite no longer being under your control.
Tip: For more information about financing a business purchase, read our article How to Finance Buying a Business – Everything You Need to Know
The Wrong Buyer?
Once the new owner took over, the business began to struggle. Rachel recalls logging into the company email inbox several months later. “I could see unanswered complaints, from a business that never had any issues before…it was horrible, absolutely horrible. Everything [the new owner] did was not what she said she would do, and it was against the contract.”
The buyer came from a marketing background, with limited experience in sales or customer service – both essential skills in the events industry. Soon after purchasing the business, she installed her son in a management role, but Rachel believes it wasn’t the best fit. “He was an introvert managing lots of front of house enquiries, which might not have been the best fit. He set up his office right at the back of the building, instead of at the front where you can greet your clients.”
There’s an important lesson here for anyone considering buying a business: choose one that genuinely suits your interests and skillset. Running a business requires a major investment of time and energy, and that commitment becomes much easier if you actually enjoy the work. The same applies to sellers – take the time to understand your buyer, and make sure they know exactly what the business demands.
SportySkirts.net - Kate’s Party Rentals wasn’t Rachel’s only entrepreneurial venture. Encouraged by the success of the business, she later launched a company inspired by her background in sports science and sports psychology. SportySkirts.net was designed to provide comfortable, flattering sportswear for women, with “details that men and big clothing industries don’t often think of.” Rachel personally designed and tested all the products herself, and the flexible e-commerce business is still listed for sale on BusinessesForSale.com. You can visit the listing page here.
Turning Things Around
Rachel stayed in regular contact with her team of five staff members and continued hearing stories about problems within the business. “The staff were the most important thing for me,” she says. “In the end it wasn't about the money, it wasn't about my reputation, it wasn't about any of that. It was just about making sure those people had food on their plates, that they had income and support.”
Watching her former staff struggle was difficult, especially while she was also trying to build a new life in the UK. One lesson Rachel now shares with other entrepreneurs is to be cautious about absentee ownership. Buying a business is a hands-on commitment – not a passive investment that makes money while you sit back. “The minute you step away from your business, you should expect some hardship,” says Rachel. “When the cat’s away, the mice play.”
Eventually, the contract terms were breached badly enough that Rachel terminated the agreement and regained control of Kate’s Party Rentals. “I had to spend a whole lot of money buying more equipment, freshening up the business, getting someone really good in front of house to push up sales,” she says.
That renewed investment of both time and money helped restore the business, and Rachel listed it again on BusinessesForSale.com several years later. This time, she found a buyer who already worked in the catering industry. “He was a perfect bridge for the business,” says Rachel.
Letting Go of a Family Business
Finally finding the right buyer for her mother’s business was a bittersweet moment. Letting go of any business after two decades is difficult, but especially so when there’s a close family connection attached to it. Looking back on the experience, Rachel found comfort in a letter from her mother that was discovered after her passing.
“My mum had written me a letter. It was hidden, and we only found it after she'd passed,” says Rachel. “In the letter she said that I was to release the business - but I was brought up with it, I remember wrapping plates as my pocket money. So I decided to take it on.
“Now that I’ve sold it, I always go back to that letter, and remember that it’s okay to release the business. It was difficult to cut that cord, because it was the most direct link I had with my mum, the last bit of her I could hold on to and make her proud. But there had to be a separation somewhere in the sale where I said to myself - her spirit is with me, not with the business, and I'm okay to let that go.”
