Over 40 years, he cornered the UK fast-fashion market, supplying 70% of the clothes sold by his pal Philip Green and other retailers. In a late change of tack, he built a portfolio of blue-chip clubs and iconic restaurants. Now, recession or not, he's taking these brands abroad.
At the 11th hole on Wentworth's West Course, my golf ball is heading for the green. Instead of bouncing straight, it goes left, clips the edge of a bunker and ends up in the sand. 'Who put that bunker there?' I shout. From across the fairway, Richard Caring responds, laughing: 'I did!' He flashes a dazzling smile. I swear I've never seen anyone with whiter, more perfect teeth than Caring.
Golf has a reputation for stuffiness, and as one of the most prestigious clubs in England, Surrey's Wentworth should be right up there in terms of petty rules and stifling atmosphere. But it's not like that. Despite a joining fee of pounds 15,000 and an annual hit of pounds 7,000, it offers rooms that are relatively contemporary and a casual ambience. The service is warm and personal, the bar staff know how to make cocktails, and the menu in the main Grill restaurant name-checks dishes from London's Le Caprice and The Ivy.
Overseeing it all is Caring - at 61, a multi- millionaire Londoner who started out in the rag trade and now commands a global empire that takes in fashion, property and some of the world's most famous names in restaurants and clubs: Wentworth, Annabel's, The Ivy, Le Caprice, Cecconi's, J Sheekey, Rivington, Daphne's, Bam-Bou, Soho House, Mark's Club, George, Scott's, Electric House, Pasha, High Road House, Harry's Bar, Cote, the Bath & Racquets Club.
A large slice of Camden Market is also his, and the old US Navy building in Grosvenor Square (he plans to turn it into luxury flats) - as is Babington House, Somerset, the country arm of Soho House. That's just in the UK. Soho House club has gone overseas, to New York (it opens shortly in Berlin, Hollywood, Miami and Chicago) and Caring has just launched Cecconi's in Los Angeles. There's a Rivington in Dubai and soon there'll be a Caprice in New York.
Much of this has been accomplished at breakneck speed. While others such as Robbie Tchenguiz are paying the price for massive over-leverage, Caring is spending hard-earned money. In 2005, he was a relative unknown. He still is. He likes to keep a low public profile.
If he was known at all, it was as the man who supplied clothing to stores owned by his best pal, Sir Philip Green. Most of his time was spent in Hong Kong, where he had his home and main base. Then he embarked on a spending spree that has left the restaurant world gasping. And he shows no sign of stopping - his name is constantly linked with possible further purchases, the latest being Italian chain Carluccio's.
Caring likes to remain in the background, but there is no mistaking him. At 61, he may qualify for a free bus pass, but he looks remarkably well preserved - the result of running every day on Hampstead Heath with his German Shepherd dogs. With his thick, swept-back hair and lean frame, he looks more like a snake-hipped, ageing ballet dancer than a business tycoon.
In London, his home is a vast mansion near Kenwood House that he shares with his wife, Jacqui, a former model (they have two sons, Jamie and Ben, who both work for Soho House). It has a 55ft ballroom, cinema, a dining room that seats 30 and a two-acre garden with a lake.
His office is an anonymous modern building between Fitzroy Square and Euston Road. Caring's own lair is on the top floor. It's a huge room, with a fully equipped bar and a roof terrace that faces south across the West End. As well as the spectacular, sweeping view, it's the art that catches the eye. There are Degas drawings, a Matisse painting and, in the middle of the floor, a Henry Moore bronze of a mother and child. The sculpture had to be lifted in by crane, he explains. …