Business

The man who was fired from Checkers, broke the law, and built a R20 billion retail empire

Kirsten Minnaar • 13 October 2025

After being fired from Checkers, Raymond Ackerman founded one of the biggest retail empires in South Africa, Pick n Pay.

Today, Pick n Pay is one of South Africa’s most well-known stores, but Ackerman took a very unconventional approach and even broke the law to build the business giant.

Ackerman was born in Cape Town in 1931 as the son of prominent businessman Gus Ackerman, who founded the Ackermans clothing group.

He attended Bishops Diocesan College, an independent Anglican boys’ school in Cape Town. As the only Jewish boy, he quickly learned how it felt to be discriminated against.

Ackerman decided to start a night school where he taught young black adults how to read and write, despite South Africa’s growing anti-black sentiment.

After graduating from school, he continued this training while attending the University of Cape Town, where he enrolled as a Bachelor of Commerce (BCom) student.

It was in one of his classes, taught by Professor WH Hutt, that his entire outlook on the business world would be shaped.

“Right, why have you guys come to my class?” Hutt asked the class. “I’ll answer the question – and I want you to put your hands up if I’m right – you want to make money quickly.”

Naturally, everyone in the lecture raised their hands. “I’m going to fail you all in three years’ time if you think that that is the aim of business and that’s the way to run a business,” the professor said.

This approach was not what Ackerman or his BCom classmates were expecting. Hutt taught them about the dangers of monopolistic practices and cartels, and the primacy of the customer in economic relations.

“He taught me that if you care for customers, they will care for you,” Ackerman said. “At a time when cosy agreements between business and governments were the norm, his exhortations to fight monopolies and cartels struck a chord with me.”

These ideas resonated with Ackerman, who had been struggling to decide whether to go into business or become a doctor, since he knew he wanted to do more than simply maximise profits.

Not everyone felt the same way, though. When Ackerman’s father learned of these lectures, he was not pleased.

“I’m going to take you out of university, this guy is talking absolute rubbish,” his father told him. “He’s a university professor and we’re in the hard world of business, and maximising profit is exactly what businesses’ goal is.”

Founding Checkers

Despite his father’s distaste, Hutt’s ideas were firmly implanted in Ackerman when, at age 20, he joined Ackermans as a trainee manager in 1951.

When the Ackermans group was bought by competitor Greatermans, Ackerman accepted a position in Johannesburg and persuaded the company to invest in modern supermarkets.

The idea came from a supermarket convention Ackerman had attended in the United States. In 1955, he was put in charge of launching the Checkers supermarkets.

Ackerman applied the supermarket principle he had learnt about overseas – giving consumers low prices. The concept took off, but the Greatermans board remained sceptical and heavily opposed Ackerman’s pricing strategy.

“They were very conservative, and they only understood clothing and high margins,” Ackerman explained.

“They didn’t understand the thrust of a supermarket – low prices, fighting like mad for the consumer, how food prices affect every household, particularly poor people.”

Eventually, he managed to grow Checkers to an 85-store chain. However, the tension with management never ceased.

“Business is tough, we want to maximise profit,” the Greatermans board told him. “Your prices are too low, and unless you agree to fix prices with the other chains, you won’t keep your job.”

Ackerman refused, and just like that, he was pushed out of the Checkers business. He was worried about how his wife, Wendy, would react, since she was ill and pregnant with their fourth child at the time.

To his surprise, however, Wendy was thrilled. She called it the “best day” of his life and encouraged him to found his own supermarket chain.

Pick n Pay

With the financial backing of 50 friends and family, Ackerman and Wendy purchased four small stores in Cape Town, called Pick n Pay, in 1967.

The retailer’s strategy was built on four legs – administration, merchandise, PR and social responsibility, and people.

At the time, apartheid and the growing global anti-South African sentiment made it very difficult to grow a business. However, Ackerman was determined to do business the right way, fighting for the principles he learned in university.

One key part of this was keeping prices – and profits – low, the very strategy he had just been fired for using at Checkers.

Ackerman kept Pick n Pay’s net profit at 3% to 5% of turnover, compared to other large chains, like Woolworths, OK Bazaars and Checkers, which operated at a 7% to 10% profit margin.

Fortunately, this worked in his favour and gave him a competitive advantage over more established chain retailers.

Controversially, Ackerman also promoted black employees to managerial positions, even though this was not permitted under the Group Areas Act.

Eventually, former president BJ Vorster called him to his office and reprimanded him for breaking the law. Ackerman presented the president with a folder full of letters sent by the wives of Vorster’s cabinet ministers praising the managerial staff at Pick n Pay.

Ackerman was able to escape arrest when Vorster ultimately agreed to turn a blind eye, and he continued running the business as he had been doing.

Other initiatives, such as building homes for his black employees who were not allowed to own property, quickly endeared him to the community.

At the same time, he was also constantly fighting the government over price control and pushing to bring prices down on items like bread and petrol.

Ackerman’s innovative concepts and strong business sense made Pick n Pay one of the country’s biggest retail giants.

In its first trading year, Pick n Pay made a profit of R310,000 on a turnover of R5 million. By 1983, turnover topped R1 billion and doubled three years later.

Ackerman and Pick n Pay were also responsible for numerous pioneering concepts in South African retailing, including hypermarkets, generic “no-name” brands and in-store banking.

Unfortunately, Ackerman passed away in September 2023. He is still widely regarded as one of South Africa’s best and most influential business leaders.

The Ackerman family remained in control of the business for 57 years before giving up control of the retailer in 2024.

Today, Pick n Pay is a household name, with a market cap of R20 billion, over 1,700 stores across the country and 90,000 people across its company-owned and franchise operations.