IF OLEG ZHEREBTSOV reads the wind in the sails with the same accuracy as he once read the shifting breeze of Russia’s postcommunist economy, the winner of the next Volvo Ocean Race is already a foregone conclusion. Sadly, as the 39-year-old multi-millionaire is finding out, the secrets of the sea are harder to master than the principles of business.

On a recent visit to England, Zherebtsov wrote “sailor”, not “businessman”, on his entry visa and felt absurdly proud of his new profession. Mildly bored by his business success, he has bought himself a boat, a racing team and an entry into the 2008-9 Volvo Ocean Race, which, it was announced recently, will finish after 12 legs, nine months and almost 40,000 nautical miles in his home port of St Petersburg.

Despite his £10m input, simply being a wealthy figurehead and benefactor is not Zherebtsov’s way. He wants to be a proper member of the crew, not just the owner who bought his berth. So, for the past three years, sailing has become his way of life, and he has dedicated himself to the task.

“I grew up in a very simple family,” he says. “We were products of the cutting grass system – you know, everything the same height, a very basic family, so why change now? I could have bought a private jet, a house in the south of France, fast cars, maybe even a football club, but I like action.”

The story of the coalminer’s son from the Caucasus who began by selling shoes on the streets of St Petersburg and now owns the largest hypermarket chain in Russia is part modern Russian fairy tale, part Tolstoy.

As a child, brought up in the mountainous Kabardino-Balkar region of the Caucasus, Zherebtsov loved geography, putting names to rivers and towns. He listened intently to tales of the friend of a friend who once visited Paris. He learnt to ski and box as a boy and pursued any glimpse of adventure, serving with the intelligence forces in Uzbekistan when the Soviet army was fighting an unwinnable war in Afghanistan.

After national service, like a character in War And Peace, he headed for the glittering court city of St Petersburg, where he attended the mining university and sensed the changing economic climate. Renting a 500sq m warehouse, he started off with a workforce of six, selling biscuits, chocolate, sweets, sparkling wine and anything else that he could buy off the streets.

Fourteen years on, his company owns 27 Lenta hypermarkets, each one bigger than the largest supermarket in England, and has a total of 12,000 employees. He set up the first St Petersburg radio station and after 3½ years sold it to News Corporation. “I stepped out of my other life because it had become routine for me,” he says. “Everyone should take a break. I’ve got some funds that allowed me to do something else.”

A chance meeting with Andreas Hanakamp, an Austrian Olympic sailor, showed him the way. “I went on a sailing holiday in Croatia and that was it,” Zherebtsov says. “I like the freedom, the freedom of sailing, the travel, seeing wild nature. Having lived in the Soviet time, I think freedom is the most important thing in life.

“Then everything happened so quick. Two years ago I had never heard of the Volvo Ocean Race; now Russia is competing and the finish of the race is in St Petersburg. But I don’t want to be the passenger. That would not be honest. I want to play a role.”

So, part of the deal with Michael Woods, a former race director of the Volvo who is managing the Russian campaign, and Hanakamp, a 6ft 6in double Olympian, is that they coach their owner in the arts of offshore sailing. On a recent family holiday in Sardinia, Zherebtsov spent most of his time on the water, sailing a Laser with his personal trainer.

His first taste of life at sea came in the summer as a pitman on a Volvo 60, hauling wet, heavy sails in and out of the foredeck hatch in a Force 8 storm, never seeing the sky. Woods and Hanakamp thought the adventure might end there and then. Zherebtsov not only survived, he was one of the few crew members who did not suffer from seasickness. He thrived in the conditions and relished the experience.

He was in Lymington recently to check on the progress of his Rob Humphreys-designed Volvo 70, which is being built in the yacht haven. It is due to be launched in April, with a hectic bout of testing and racing scheduled for the summer in preparation for the October start from Alicante in southern Spain.

In the meantime, the search is on for a core of Russian sailors to crew one of the most volatile racers in the world. Zherebtsov wants at least three or four of his countrymen in the 10-man crew. “It’s important to me that we are representing Russia and that we are able to show what is possible,” he says.