Jim Cregan’s Strategies For Success

One day, while driving across the country in a 4x4 truck, he found himself dehydrated and hankering after a caffeinated drink that wasn’t one of the usual suspects. He pulled into a petrol station, where he came across a carton of ready-to-drink iced coffee—something he had never seen before. “I had a few swigs of it,” Cregan told the audience at HSBC’s Strategies For Success event. “And I was immediately hooked.”

By the time Cregan returned to the UK, his taste for iced coffee had developed into an obsession. He decided to set about creating his own brand, and co-founded Jimmy’s Iced Coffee in Dorset in 2010 with his sister Suzie. Packaged more smartly than competitors, and carried by premium stockists, it launched just as a UK iced coffee boomlet was getting underway.

The business grew quickly, and a Jimmy’s carton is now sold every two and a half seconds from one of more than 10,000 outlets around the country. In 2022, Cregan sold Jimmy’s to Britvic, just as annual sales hit £17 million.

Today, Cregan is considered one of the UK’s entrepreneurial success stories. So how did he do it? At the HSBC event, he shared his strategies for success…

In the early days, Cregan was driven by the fact he had spotted a gap in the UK iced coffee market. “We knew there was something there,” he said, “and I had bundles of energy to go and pursue it further.” He was convinced that, as long as he could stay the course, Jimmy’s would be a success.

That motivation was vital for putting in the hard yards that the early days of the business demanded. For the first ever batch of iced coffee, for instance, Cregan and his sister had to stick 3,000 labels onto cartons in a walk-in fridge because printed cartons were too expensive to source. “It took 25 hours,” he recalled. The pair then went out and personally handed out hundreds of samples to consumers to gather feedback and spread the word about Jimmy’s. The next day, they drove up from Dorset to London to pitch to stockists—and the pace never really let up from there.

His conviction that it would all be worthwhile was what kept him going.

Even after Jimmy’s was established and selling well, Cregan was constantly comparing his product to competitors’ and looking for ways to differentiate and innovate.

He found the hands-on approach essential. “We didn’t buy any data,” he said. “The research involved going to supermarkets and coffee shops and seeing what was there on the shelves.”

One fruit of this was Jimmy’s distinctive packaging. “I felt that we had the ingredients and we had the branding, but the packaging wasn’t working in the carton format we had,” he said. After an employee went to Hong Kong and brought back a bottle made of recycled aluminium (a “BottleCan”) as an example of how iced coffee was sold in the city, Cregan tracked down a manufacturer in Japan who could make the same for Jimmy’s. The unique design became a brand signature.

Cregan’s approach when it came to retailers was to shoot for the moon. “It was like: ‘Right. Where do we want to list our product?’ And we thought, well, the coolest place to get your product is Selfridges on Oxford Street. You start with the premium retailers, and then you filter down.”

So in April 2011, Cregan called Selfridges and, having ensured it met their standards, pitched the product. To his delight, they said yes. If he had assumed it was a non-starter that would never have happened, and it ended up being pivotal.

He spent a month sleeping on a friend’s sofa in London, going into the store every day to give shoppers samples of the product, gradually increasing the rate of sale. That success in turn convinced more stockists to take it on. “It allowed us to get into the likes of Whole Foods.”

Cregan has a business mantra: “Hurry slowly”. It means being deliberate about how fast you act, by always balancing pace with prudence.

Sometimes it’s appropriate to sprint. In one instance, Cregan and his team owed money to a packaging manufacturer. The manufacturer had allowed Jimmy’s to sell their product before paying for the packaging—“payment was set for much, much later”, said Cregan—but eventually the debt was called in. Speed was essential or the manufacturer would stop production but Cregan didn’t have the cash to pay on the spot. He came up with a workaround: he asked a stockist to pay the manufacturer, rather than Jimmy’s, for goods supplied, so the debt could be settled fast.

Other times, it’s right to take a little time. Cregan recalled a moment when the four company directors had all assessed a colleague and decided to keep them on, but wanted 24 hours to sleep on it. The next day, all four of them had separately changed their minds.

The takeaway here? Before acting, ask yourself: 'Is this a moment to move immediately, or a moment to pause and think?'

“I think the toughest part of running a business was my urgency to make it grow faster, and being like ‘Why is this taking so long?’” he said. “But that's my own urgency; these things do take time, and they are organic.”

Take securing stockists. Buyers rarely feel the same sense of urgency as founders, so Cregan remembers many meetings getting postponed or cancelled at the eleventh hour. It took ten years of lobbying, for example, to get Jimmy’s stocked in one particular supermarket.

See every conversation as a long-term play, and view consistent effort, day in and day out, as the key to lasting success.