Last week the latest chapter in the Simon Nixon success story saw the multi- millionaire pick up the Business Person of the Year Award at the 2009 Cheshire Business Awards. This week Chronicle reporter David Holmes talks to the entrepreneur about his remarkable life

Multi-millionaire entrepreneur Simon Nixon is relaxed about losing almost £100,000 a month on his new internet business.

The Chester-based founder of Moneysupermarket.com, who is worth hundreds of millions, is confident he will recoup losses on simonseeks.com within four years.

He hopes TV advertising will transform the travel website, which employs 18 people in Shipgate Street, into a web phenomenon once the site has been fine- tuned.

Simon, 42, who recently scooped the Cheshire Business Person of the Year award, said: “If you chase the money too early on, you cut too many corners and it’s short- sighted – that’s one of the best business tips, I think.”

Simon’s latest enterprise is Simon Escapes, which involves letting luxury holiday homes in some of the most stunning parts of the UK, combining his love of travel and property.

The rental fee is intended to cover costs only but he hopes the capital appreciation will be significant given the unrivalled locations, including the Lln Peninsula in North Wales, the Cotswolds and Cornwall.

“I will also get to go myself on two or three weekends for free because the maintenance is paid for,” he said. “It’s more a fun thing but a serious investment.”

With the looks, the charm and the business pedigree, it’s no surprise the producers of Dragons’ Den approached Simon to do a screen test.

But the quietly spoken businessman couldn’t afford to take the six weeks out for filming and wouldn’t like the trappings of fame.

Of course, he could just retire to a Caribbean island with his only dilemma whether to go jet skiing or snorkelling in the afternoon.

“I’d be depressed in about three weeks probably,” said Simon, who adds that money was only ever a byproduct of his success and never a motivating factor.

“Fear of failure is the biggest pressure, even though for me I’ve made it and got total financial independence. The pressure of failing in a business is one of the things that drives me on.”

Simon’s drive in the boardroom is replicated in his desire for self- improvement in the time he has on the planet.

He loves travel and sampling new cultures and is currently having cooking lessons and studying antique collecting and wine tasting – he is investing in fine wines and antique watches as ‘a bit of fun’.

And while he does not expect any sympathy, the card-carrying, super- rich club member admits having the infinite choices over ‘what to do’ and ‘where to go’ can be ‘stressful’.

Helping him to keep his feet on the ground is his ‘level-headed’ girlfriend Caroline Sadler, a ‘nearly divorced’ housewife with two children, who he has known for about 14 years.

“Because I’ve known Caroline for a long time, I trust her,” he said. “I’d known her before I had money.”

What would his friends say about him?

“They’d describe me as an honest, down-to-earth control freak!” he said.

Simon’s weekly routine involves a rigorous health regime, hard work and plenty of playtime.

He wakes up at 7.30am each day.

“I’m not one of those people who gets up at 5am,” he said. “I’m not an early morning person.”

A creature of habit, he switches on Radio 1 in a bid, he says, to cling on to his youth, makes the same vegetable juice every day and eats his wheat-free muesli (wheat causes bloating, apparently).

Then he reads the Financial Times, looking out for internet, travel and property-related articles.

“It’s important to know what’s going on in the world – what’s going to impact on you – before you get into work,” said Simon, who does yoga three times a week.

Leaving his Ferrari 599 behind, he takes a brisk 15-minute walk into work, which helps clear his head and makes sure his brain receives some sunlight to ward off the winter blues.

Simon is now ‘ready to fire away’ for a day that will inevitably involve a series of meetings focused on product improvement.

One day a week he will spend in London, often giving media interviews. He is just about to do a piece with Conde Naste Traveller, whose readership, he says, are the ideal target market for his travel- based businesses.

Simon has relinquished day-to- day control of Moneysupermarket but remains the majority shareholder and still spends one day a week at the Ewloe-based business which made him his millions.

Most Friday afternoons Simon will jet away to some foreign clime. He has just returned from Rome, from where he Tweeted about his experiences.

For European trips he uses ‘no frills’ airlines – but does pay more for extra leg room and priority boarding. Occasionally he will hire a private jet if the times don’t suit.

These days he some very rich friends, one of whom will sometimes pick him up in their helicopter and take him out to lunch in the Costwolds or the Lake District.