Sam Waley-Cohen: Mountaineer, businessman, pilot, skier... oh, and jockey

The Southern Cranes & Access Services Ltd Open Maiden Race at Tweseldown point-to-point in Hampshire bears scant resemblance to the Cheltenham Gold Cup, except that both in their different ways shed light on the extraordinary life of 28-year-old Sam Waley-Cohen, the amateur jockey who is due, a week today, in the chocolate-and-orange colours of his father Robert, to ride second-favourite Long Run in the Cheltenham Festival's blue riband event.

Waley-Cohen won twice at Sunday's point-to-point, having helicoptered himself to Tweseldown. He has been piloting helicopters since he was 21, and aeroplanes since he was 18. He is a mountaineer, too, but likes to set himself a challenge getting down as well as up, so when he recently climbed Mont Blanc, he did so carrying skis, then skied down from the summit. Last year he ran the London Marathon, but not, of course, the easy way. He was roped up to 35 others, in an assault on the world record for the most people to run a marathon tied together.

His is a rich, privileged and fun-loving young man's lifestyle, that could be dismissed as self-indulgent, decadent even, were it not for three things. One, he raises a great deal of money for charity, not least towards the running of Tom's Ward, a children's unit at Oxford's John Radcliffe Hospital named after his younger brother, Thomas, whose death from cancer in 2004, aged 20, is one of the reasons Waley-Cohen tackles life with such buccaneering verve.

Two, he has, with singular drive and vision, built up a string of dental practices. He's not a dentist; just an entrepreneur whose "light-bulb moment" occurred, coincidentally, in the weighing room at Tweseldown some years ago. Where Clare Balding saw a jockey with bad teeth (Liam Treadwell) and cracked an uncomfortably public joke, Waley-Cohen spotted a business opportunity. Why, he wondered, looking around, were people's teeth so bad? Partly, he decided, because so many dental practices were poorly run. Portman Healthcare, with 170 employees and growing, represents his dynamic and doubtless lucrative solution to the problem.

And three, while he plainly wouldn't be partnering such a fancied horse in next week's Gold Cup were his father not the owner (as well as Cheltenham's chairman-elect), he has more than earned his spurs as a horseman. It is less than two months since he faultlessly steered Long Run to victory by 12 lengths in the delayed King George VI Chase at Kempton Park. It was trainer Nicky Henderson's inaugural success in the King George, A P McCoy on Kauto Star finished a distant third, and Waley-Cohen, with a fifth place in the Grand National and two wins over the Aintree fences already on his CV, banked himself yet more credibility as a big-race contender.

To meet him, I travel on a glorious March morning to Upton Viva, the handsome stud farm between Stratford and Banbury owned by his parents. The Waley-Cohens are an illustrious lot. Immaculately clipped topiary racehorses on either side of the front door indicate their principal interest nowadays, but Sir Bernard Waley-Cohen, Sam's grandfather, was Lord Mayor of London, and Sir Bernard's father, Sir Robert, was a leading light in Anglo-Jewry and a founder of the Palestine Corporation, created in 1922 to promote the economic development of what was then the British mandate of Palestine.

Inside the house, the high-achieving scion of a high-achieving family is visibly taken unawares. He had clean forgotten I was coming, which is perhaps understandable, given the constant juggling of commitments that becomes even more frantic in the run-up to Cheltenham. Short and wiry, with dancing brown eyes and the public schoolboy's accent you would expect of a fellow who counts Prince William and Kate Middleton as old friends (and indeed is said to have brokered their 2007 reconciliation), he asks me to wait while he fires off a few business emails, and then we settle in the spacious Upton Viva kitchen, to consider, first of all, Long Run's chances of landing Henderson a first Gold Cup.

"It's a time of high tension," he says of these pre-Festival days, "when people find fault with the slightest things. You know, the lie of a horse's hair is not quite sitting right, what does that mean? Yet everyone seems incredibly happy with him, which is rare in the racing world. He's in good shape. Nicky is a bit like Gordon Ramsay this week, adding the final bits of garnish to a great raw product."

But is the significant word there "great", or is it "raw"? The French-bred Long Run has not prospered in his outings at Cheltenham so far, and there are suspicions that the track doesn't suit him. Waley-Cohen rejects this, and besides, the horse has since been put through his paces by the jumping guru Yogi Breisner.

"He's a horse with great self-belief, but that cocksuredness meant he didn't always respect the fence. In France, where the fences are a bit softer, you can get away with that. If you don't meet them quite right you can take the top six inches off, but if you do that here you're in a whole world of trouble. So we've had to address that. Physically, there's no problem with his jumping. The challenge next week will be to get into a nice even rhythm round the undulations. But I wouldn't want to be on any other horse. If you gave me a list and said pick one, I'd pick Long Run."

This is predictably assertive stuff, but Waley-Cohen hardly needs reminding that there are three previous Gold Cup winners in a formidable field, and that their names happen to be Imperial Commander, Denman and Kauto Star. Whether the latter two in particular have now peaked is, he says, "the million-dollar question. The stats guys will tell you that an 11-year-old hasn't won since 1958 or whatever, but that a six-year-old hasn't won for 40 years either. There's a big sense of the unknown about this Gold Cup."

He was not at all miffed, he adds, when the media pounced less on his and Long Run's success in the King George, than on the eclipsing of Kauto Star. "He's been a worthy champion for so long, I quite understood why he was the focus of racing's attention. Long Run announced his arrival on the scene that day, but he hasn't staked a place in racing history in the way that Kauto has. It was legitimate for us even to ask ourselves whether we were as good as we appeared to be."

And the answer? "Yes. In the past five years there's been only one faster King George, and [runner-up] Riverside Theatre has since won very well. I have every confidence in the horse, and in the way I'm riding, which is probably the best I've ever ridden."

I wonder, though, whether he feels entirely embraced by his peers. His obvious talents notwithstanding, does the weighing-room camaraderie extend in full to a wealthy young man riding his dad's horse?

"I think I'm a bit of a novelty to them, but when they've seen you boiling like a lobster in the sauna, and nursing a few bruises, then you do get respect," he says equably. "I try to find a balance. It's their day at the office, so it's no place for joking, but at the same time it costs me a fortune to be there, it's not like I'm going to make a fortune, so it's got to be a bit of fun, otherwise what the hell are you doing?"

Fair enough, and since he is a manifestly likeable fellow I am sure he's popular in the weighing room. But it seems worth probing again; has he ever overheard the whispered charge of nepotism? He smiles. "Racing is a brotherhood, and it extends across a full range of emotions. There's goodwill, competitiveness, envy, outright animosity. I know I'm lucky, but everyone there is on a good horse through some break of good fortune. I don't sit in a corner thinking I shouldn't be there. On the contrary, my amateur status is a huge motivation, to show them that I deserve to be there, and the truth is that once you're legged up on to the horse, it doesn't matter what helping hand you've been given. Also, while I know I'm at a disadvantage because I don't ride as much as the professionals, I try to turn that into a strength. I can do the homework, study the videos, that they don't have time for."

I don't suppose that any amount of preparation, though, can eradicate the self-doubt that must surely creep into his mind if he glances across in the final furlongs to find himself neck-and-neck with McCoy's mount, or Ruby Walsh's? A short laugh. "Well, you think, 'Blimey, that's McCoy, or Ruby, or Dickie Johnson,' but not in the sense that you can't beat them. What you know is that your horse has to be better than their horse. But very few races are won in the last furlong. Most are won, by jumping and strategy, a long way out."

It is an analysis that applies a hundredfold to the Grand National, the race that 20 years ago kindled Waley-Cohen's interest in the Turf. In this year's National on 9 April he hopes to ride one of the ante-post favourites, only part-owned by his father, Oscar Time. "He's awesome, a brilliant jumper. And the National is probably my favourite race, ahead of the Gold Cup. Obviously the Gold Cup is level weights, top horses, on the biggest stage for the biggest prize, yet for me the lure of the Grand National is what it represents. There's ego, greed, envy, danger, death, blood. It's life distilled into a few minutes, with glory and wealth at one end, disappointment and devastation at the other, and a lot of mediocrity in between."

It is eloquently put, as is his answer to my question about his mental priorities. Does he ever find his mind wandering, while racing, to Portman Healthcare? Or, when at his desk studying spreadsheets, to Cleeve Hill or Becher's Brook? "Actually, no. When those goggles go down, your whole world is between those two furry ears in front of you. That's what's so great about it. And I don't think about racing when I'm working, either. You can't when you have 170 people working for you, all with families, all needing to live."

As for his own domestic arrangements, they are set to change in June, when he gets married. It is not quite, though, the society wedding of the year. So is it true that we can thank (or perhaps blame) him for the increasing royal wedding hoopla?

For the first time in an hour, he looks ever so slightly uncomfortable. "Supposedly. I'm not sure I was the Cupid's arrow... they probably would have worked it out on their own account. But they've both been friends for a long time." And the invitation is on his mantelpiece? "Yes, although I keep teasing my fiancée, Bella, that if there's racing that day we'll be going racing." He chuckles. "But I don't think she's having any of that."

Latest in a long line of successful Waley-Cohens

Sam is just the most recent member of the Waley-Cohens to hit the headlines as his ancestors have a history of attracting both wealth and status.

* In starting Portman Healthcare, it seems Sam has inherited some entrepeneurial blood. His father, Robert, founded Alliance Medical in 1989 and sold it in 2007 for £600m.

* His grandfather, Sir Bernard, was a businessman connected with investment banking, real estate development and farming. In 1960 he was elected Mayor of London. His one-year term is best remembered for the parties he gave at his official Mansion House residence. He was given the title of Baronet of Honeymead, a title passed on to his son, Stephen, who is Sam's uncle.

* As well as being a leading light of Anglo-Jewry, Sam's great-grandfather, Sir Robert, was an early oil pioneer. Joining the Shell Oil Company in 1901, he negotiated its merger with the Royal Dutch Oil Company, becoming director of the company.

Michael Butler