As the man who went from selling phones from a flat off Marylebone Road to the upper ranks of the young, buccaneering super-rich, David Ross could claim an astute understanding of reward and risk. But if the luck that helped him to an £800million fortune was finally on the wane in recent months, few of his glamorous associates would have been able to guess it.

When Mr Ross took his latest girlfriend, Emma Pilkington, to a party hosted by Prince William on Mustique in the summer, it was on Talitha G, the super-yacht owned by the Getty family and hired to others for somewhere north of £100,000 a week.

The Caribbean cruise, along with the mansions, cars, parties and beautiful women, epitomised a career that soared with the telecoms boom for almost two decades.

From the moment he walked out of a junior accounting job at Arthur Andersen to help his friend Charles Dunstone to sell mobile phones, Mr Dunstone doing the marketing, Mr Ross the accounting and legal side, the partnership brought dividends. By the 1990s the pair and the fledgling Carphone Warehouse had 20 stores; now it has 2,400 in nine countries.

Mr Ross, known to friends as “Rosso”, came from a wealthy Grimsby fishing family - his grandfather John Ross turned a small company into one of Britain's biggest suppliers - but did not want to join the family business. He dates his go-it-alone drive to holiday work experience on an Algerian building site, arranged by his father, when he was 16. He describes it as a defining moment, when “I knew I had to be able to control my own destiny”.

With Mr Dunstone he found himself in the right place, with the right friend, and the right idea. The pair turned Carphone Warehouse into the largest independent mobile phone retailer. When they floated the business in 2000, it had been so successful that the partners had not needed to borrow or involve outsiders: Mr Dunstone owned half, Mr Ross a third, and another partner, Guy Johnson, most of the rest. While Mr Dunstone stayed with the business (he still runs it today) Mr Ross drifted away, giving up his executive position in 2003 and periodically selling some shares.

His love life began to reach the newspapers: at this time he was dating Ali Cockayne, the former lover of the ex-England rugby captain Will Carling, but the relationship, like many, faded. Other loves have included Saffron Aldridge, the society journalist and model, and Shelley Ross, a trained ballerina who worked as a pole dancer at Stringfellows to make ends meet.

He met Miss Ross when she was struggling with her luggage at Heathrow and their relationship was unconventional. They had a son but lived separately and did not marry (the surnames are a coincidence). At one point Shelley was ordered to do 120 hours of community service after claming benefits while working as a model.

After the Carphone flotation, Mr Ross broadened both his portfolio and his lifestyle. He cultivated links in the Conservative Party, helping to organise the summer fundraising ball in 2006, when eyebrows were raised because Shelley sent out the invitations, and was even considered as a possible candidate for London Mayor. Instead, a job as Boris Johnson's representative on the 2012 organising committee followed.

His wealth allowed him to buy estates in Leicestershire, including the 2,000-acre Nevill Holt, home to the Grange Park Opera, and Brampton Ash, once owned by the family of Diana, Princess of Wales. Shooting became a passion both in Leicestershire and Yorkshire, where Mr Ross bought grouse moors costing £22 million. For tax reasons, however, he spends much of his time in Switzerland.

Brampton Ash was put up for sale for £7.75 million last month, reportedly because Mr Ross's stepsister was stabbed to death by her former husband in a bungalow on the estate in 2006.

A contradictory character with the occasional air of the barrowboy, despite his Uppingham upbringing, Mr Ross has been a generous supporter of a wide range of interests. Besides the Tories, he backed sporting ventures such as Leicester City Football Club, was a former board member of Wembley Stadium and is on the board of Sport England's council, and a trustee of the National Portrait Gallery.

He also became a prolific property investor, including high street shopping developments through a company called Kandahar. Yesterday, as it emerged that Mr Ross may have flown too close to the sun, friends attributed his untimely and unexpected fall in part to these investments.

As he fights to keep his fortune intact, the man often dubbed Britain's most eligible bachelor is, at the very least, likely to find the title pass elsewhere.

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