Ocean Holidays co-founders

How We Made It: Our world fell apart, but now we’re flying high again

We’re proud to share this Sunday Times article, featuring our very own Co-CEOs and co-founders, about the trials and triumphs of Ocean Holidays.


The last Friday of October 2012 is forever etched in the memories of Harry Hastings and Daniel Ox, co chief executives of Essex-based Ocean Holidays. That’s not only because it was Ox’s son’s first birthday; it was also the day they discovered that the travel firm they had built up from scratch over the previous eight years was at risk of imminent collapse.

“We got the call that Friday to say the business had run out of cash,” said Hastings, now 39. “We spent the next 72 hours trying to figure out what on earth had happened. We discovered a hole of about £1.8 million in the end.”

It was a do-or-die moment, every entrepreneur’s worst nightmare. The four founders – Hastings and his brother George and Ox and his brother David – decided to try and save their floundering firm. With an emergency, insurance-backed loan from industry bonding body the Travel Trust Association, Ocean Holidays was able to continue trading while the two pairs of brothers feverishly worked on the rescue effort.

“We had seven days to write a business plan to show we could get out of where we were — to cut costs, sell assets, rebuild the business and pay off that special arrangement over a number of years,” says Ox, now 42. “Harry and I had a few very late nights doing that.”

The grim news didn’t quite come out of a clear blue sky — at the time, the firm’s finances were managed by an experienced older shareholder (who subsequently left the business) and the brothers had been concerned over a lack of financial information for a while. But the discovery of the extent of the cash shortfall was a huge shock. “We were very young when we started the business and none of us had really had proper jobs before that,” said Hastings. “Dan and I were university drop-outs. We were completely and utterly self-taught. We thought we were doing well — we didn’t know any better.”

In the end, 28 staff out of a total at the time of 85 had to be made redundant, and one of the company’s crown jewels — a successful online booking platform for travel agents called Beatthebrochure, which Ox had built himself — was hastily sold to a competitor to liberate some cash.

“It was so painful. We were in total chaos for about 12 weeks,” said Hastings. But it bought the founders time to get back on an even keel — and to realise the potential of a restructured Ocean Holidays based on two key markets. One was mid to long-haul holidays to destinations such as Florida and Dubai, and the other a bespoke travel agent, called Winged Boots, aimed at high-net-worth individuals.

“People ask why we didn’t just pack it in and start again,” said Hastings. “We had invested eight years in the business. We had thousands of customers who trusted our brands, and an incredible team working with us. Once we had built the business plan, we could see there was a tremendous opportunity right there, and we were really, really hungry for it.”

Another crisis hit in March 2020, of course, but one that was industry-wide rather than specific to Ocean Holidays – the pandemic. The company made a pre-tax loss in 2020 of £1.25 million as the world went into lockdown and travel ground to a halt. It did keep its call centres open, however, talking customers through their options and resulting in 85 per cent of them rebooking rather than claiming a refund.

After a couple of weeks, Ocean also bucked the trend by turning its online advertising back on and looking for business. “In April 2020, we started to sell holidays for beyond Easter 2021 up to 2024,” said Hastings. Few other companies were doing so, resulting in a flock of locked-down customers easing their frustrated wanderlust by booking a holiday a year or two hence. “In 2020, we ended up selling £40 million worth of holidays,” he adds.

Fast forward and the company is going strong. Ocean Holidays said its revenues were £78 million last year, when it was named the fastest-growing travel business in the UK by ATOL, the holiday protection scheme. It now has 200 staff and claims to be on track to generate revenues of almost £100 million this year, with earnings before debt interest, tax and non-cash items of “between £6 million and £7 million”, said Hastings.

The business has its roots in the 1990s, when the Ox brothers set up a business selling holidays to Dubai on Teletext, the TV-based forerunner of the internet whose pages looked like they had been drawn with Lego bricks. Daniel Ox was 19 at the time, enjoying life as a sometime DJ in Spain but not really going anywhere career-wise. “I had just dropped out of university and was messing around,” he said. “My dad was a bit of an entrepreneur — the family had fruit and veg stalls on Romford market for generations — and he said to me and my brother, ‘Why not start a travel company?’ ”

So with £30,000 from their parents, the pair set off, selling holidays to Dubai. When they decided to start doing US packages as well, they met the Hastings boys — then sales agents for a Florida villa specialist — and went into business together. “Somehow, my brother and I cobbled together 20 grand,” said Harry Hastings. “They sold the holidays and we processed the bookings, and we all got a cut.”

How does a company run by not one but two pairs of brothers manage to avoid a double dose of family squabbling in the boardroom? Each of the four owns an equal 25 per cent stake, and the business is structured so that they don’t tread on each other’s toes, Hastings explains. “We all have our own, very well-defined areas of responsibility. David is managing director of Winged Boots and George is managing director of [subsidiary company] Ocean Flights – on long-haul holidays, the vast majority of the cost is the flights. I’m the co-CEO who works closest with the finance director and head of people on product and commercial stuff, while Dan is the co-CEO of technology, operations, process and strategy.”

Now a few years older and hopefully wiser than back in 2012, when the money almost ran out, what tips would the founders give to others about to embark on their own entrepreneurial journey? “For me, I’d say double down on your strengths and accept your weaknesses,” said Ox. “Things move faster if you quickly accept what you can and can’t do.”

“Try to think long-term, even in a crisis,” added Hastings. “Making decisions based on fear is a really bad idea. One thing we discovered is that, when the thing you are most scared of happens, it can actually end up being the best thing for you. So be optimistic, but with rigour.”

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