It’s easy to get swept up in the dream 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 is usually more complicated. Selling a business doesn’t happen overnight: there’s due diligence to complete, accountants to hire, and contracts to review carefully. None of those things are especially glamorous, but they matter. Selling at the wrong time, for the wrong price, or to the wrong buyer can become a costly 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 with the sale – and shares practical advice for other business owners preparing to sell. She also reveals how she eventually turned the business around and found the right buyer the second time.
Selling the Business from Overseas
Rachel inherited an events and catering company called Kate’s Party Rentals from her late mother, who founded the business in 1989. It was a long-running company with established clients, and Rachel operated it for more than twenty years. But after she and her partner started a family, they decided to move from South Africa to the UK. Selling the business became the next step.
Rachel couldn’t find a buyer before the planned move date, which meant much of the transaction had to be managed remotely. That made due diligence far more difficult and meant she never had the chance to meet the buyer face-to-face before the sale closed.
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 be attractive for buyers because it often reduces the amount of outside financing required upfront – but it also creates risk for the seller. The business still needs to remain profitable enough to cover those 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?
After the new owner took over, business performance started slipping. Rachel remembers logging into the company email account 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 little experience in sales or customer service – both essential skills in the events industry. Shortly after taking over, she gave her son a management role, but Rachel believes it wasn’t the right 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 matches your interests and skillset. Running a business takes a huge investment of time and energy, and that commitment is much easier if you enjoy the work itself. The same lesson applies to sellers – take time to understand your buyer, and make sure they fully understand what the business requires.
SportySkirts.net - Kate’s Party Rentals wasn’t Rachel’s only entrepreneurial project. Inspired by the success of the business, she later launched a company connected to her background in sports science and sports psychology. SportySkirts.net was created 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 apparel herself, and the flexible e-commerce business is still listed for sale on BusinessesForSale.com. You can visit the listing page here.
Turning the Business Around
Rachel stayed in close contact with her team of five employees and continued hearing stories about problems inside the company. “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 employees struggle was especially difficult 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 generates income 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 buyer breached the contract 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 time and money helped revive the company, 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 company after two decades is difficult, but especially so when there’s a strong family connection involved. Reflecting on the experience, Rachel found comfort in a letter from her mother that surfaced 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.”