It’s easy to get caught up in the idealised version of selling a business. You find the right buyer, complete a smooth handover, then walk away with a healthy payout before heading off to retirement in the Bahamas.
In reality, it rarely happens quite so neatly. Selling a business is a process that takes time: there’s due diligence to complete, accountants to consult, and contracts to review in detail. None of those things are especially glamorous, but they matter. A sale at the wrong time, for the wrong price, or to the wrong buyer can become a very 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 account, she explains what went wrong during the sale process – and shares some honest advice for other business owners preparing to sell. She also reveals how she eventually managed to rebuild the business and secure a far more successful 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 Abroad
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-established operation with a loyal customer base, and Rachel ran it for more than twenty years. But after starting a family with her partner, the couple decided to relocate from South Africa to the UK. Selling the business became the obvious next step.
Rachel wasn’t able to secure a buyer before the move date, which meant much of the sales process had to be handled remotely. That made due diligence considerably more difficult and meant she never had the opportunity to meet the buyer face to face before the transaction completed.
She decided to use seller financing, where part of the purchase price is paid through the future profits of the business. Seller financing can be attractive for buyers because it reduces the amount of third-party funding needed upfront – but it also introduces risk for the seller. The business still needs to perform well enough to cover the agreed payments, despite no longer being under your control.
Tip: For more information about funding 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, the business quickly started to struggle. 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 limited experience in sales or customer service – both crucial skills in the events industry. Soon after taking ownership, she appointed her son to a management role, but Rachel believes the fit wasn’t right. “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 something that genuinely suits your interests and skillset. Running a business requires a huge investment of time and energy, and that becomes much easier if you actually enjoy the work. The same applies to sellers – take time to understand your buyer, and make sure they fully appreciate what the role demands.
SportySkirts.net - Kate’s Party Rentals wasn’t Rachel’s only business venture. Encouraged by the success of the company, she later launched a business inspired by her background in sports science and sports psychology. SportySkirts.net was created to offer comfortable and flattering sportswear for women, featuring “details that men and big clothing industries don’t often think of.” Rachel personally designed and tested the products herself, and the flexible e-commerce business is still listed for sale on BusinessesForSale.com. You can visit the listing page here.
Rebuilding the Business
Rachel remained in regular contact with her team of five employees and continued hearing stories about problems inside 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 employees struggle was especially difficult while trying to establish a new life in the UK. One key 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 runs itself. “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 ownership 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 explains.
That renewed investment of both time and money helped revive the company, and several years later Rachel listed the business again on BusinessesForSale.com. This time, she found a buyer with direct experience 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 an emotional moment. Letting go of any company after two decades is difficult, but even more so when there’s such a strong family connection attached to it. Looking back on the experience, Rachel found reassurance 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.”