(CNN) -- Would you go to work for nothing? More to the point, would you do so risking life and limb riding a horse in one of the world's toughest races?
These days amateurs competing in professional sport are almost an extinct breed, but Sam Waley-Cohen is a throwback to a bygone era -- the archetypal "gentleman jockey."
By day he runs a multimillion-dollar series of dental practices; at the weekend he rides over some of the world's toughest fences, unpaid and purely for the love of it.
A modern-day jack of all trades, he boasts helicopter and plane licenses, is a keen mountaineer and is even credited as the man that got Britain's Prince William and Kate Middleton back together after a pre-wedding separation.
The highlight of his weekend job is looming on Saturday: the Grand National, the world's toughest steeplechase with a prize fund of £1 million ($1.66 million).
"The Grand National for a jockey is a bit like a fighter pilot in his plane in a series of dog fights," says the 31-year-old, who will saddle up on one of the favorites, Long Run.
"It's a very unusual challenge of very intense periods and occasional moments of reflection. It's a race that's impossible to replicate. Every single fence is a big challenge, it's twice as long as your average race.
"It's the one and only race in the world where you can say it's the best experience of your life even if you don't win."
Waley-Cohen has come close -- he was second on Oscar Time in 2011 and fourth on the same mount a year ago. Long Run, meanwhile, is a winner of the prestigious Cheltenham Gold Cup and the King George VI Chase, two other jewels in jump-jockey circles.
"One of my first memories is riding a rocking horse at home in which I acted out riding the Grand National," he recalls. "It's a race I love, that gives me butterflies. If you don't get that with the National, you should probably think about doing something else."
Virtually every jockey in Saturday's field will be a paid-up professional, but Waley-Cohen -- who has about 30-40 rides a year -- is just happy to be competing with them.
"Sometimes I watch the pros in the races and wonder how I can compete with them," he admits.
"They're the best in the world, the best people that have ever ridden. It's such a buzz to line up alongside them.
"And I'm very lucky to have been able to do that because of my Dad."
Robert Waley-Cohen, son of the former Lord Mayor of London, owns the horses that Sam rides, and has enabled his son to pursue this hobby with, it has to be said, remarkable success.
"An amateur in horse racing, in fact in all sport, is quite rare now," says Waley-Cohen Jr. "As sport is more and more professional, it's harder to compete.
"Can someone that doesn't dedicate themselves to it day-to-day do it? It's a good question. I hope I've proved it's possible and I wouldn't say it's the end of an era exactly, but it's becoming more rare. Over the last 40 years there's been less and less amateur jockeys."
National Hunt racing is a dangerous business. At last year's Cheltenham Festival, JT McNamara was paralyzed after fracturing two vertebrae in a fall, while last month fellow Irishman Jason Maguire, the 2011 Grand National winner, was put into a medically induced coma after a fall.
Those are a mere snapshot of the sport's dangers, which makes the decision by an amateur, and one who became a parent for the first time last year, all the more surprising.
"I don't go to the races thinking I'm going to get hurt or that I'm not going to come back," Waley-Cohen says.
"If I felt like that I wouldn't do it. As for having a family, I think that makes it easier. It's not the be-all and end-all anymore as you have a family to go back to afterwards.
"But there are tough days when you fall off and are trampled over and you wonder, 'What am I doing?'"
The reason for this adrenalin junky's desire to continue racing is often attributed to his brother Thomas, who died aged 20 in 2005 from Ewing's sarcoma, a type of cancer.
"That's not quite right. It wasn't so much his death that drove me on but more the way that he lived his life," explains Waley-Cohen, who still rides with his brother's initials on his saddle.
"I think he'd be surprised how I've got on in the saddle, but he'd love it as the rest of my family do."
Thomas would be rather more surprised with the business empire his brother has since built up. He is chief executive of Portman Healthcare, which has 20 dental practices across the UK.
He employs 300 staff and has 200,000 patients in all. He is hoping to double those numbers in the next two years.
It had been rumored on the circuit that the business began after he looked around the weighing room one race day and saw the battered teeth of his peers, but he dispels this as another myth.
"Actually, there's a dentist's surgery on the way to one of the racecourses and I remember thinking, 'Why is it only individual practices, why aren't there chains?' and it went from there," he says.
"But it's very similar to horse racing. In racing, I surround myself with the right horses; in business I've surrounded myself with the right people."
Portman, he says, takes up 99% of his work time while his "second job" is usually just for weekends except for events such as Cheltenham Festival and the current Grand National week at Aintree.
Should he win in the chocolate and orange colors of his father, he will be the first amateur jockey to do so since 1990, when journalist Marcus Armytage rode Mr. Frisk to victory.
"I believe I can win but that's the beauty of the National as there will be 40 jockeys on the start line thinking the same thing," Waley-Cohen says.
"You always need a bit of luck to get over those fences as there's so many things that can happen. But I'd say I have a great chance."
If victory is his, it will almost certainly come with a royal seal of approval. It was at his family's 17th-century mansion that the Duke and Duchess of Cambridge were reunited during a party that he organized, having split in 2007.
Waley-Cohen attended their wedding in 2011 -- although he downplays the significance of his role in getting them back together -- and the Duchess was present when he was married later that year.
"Well, my comments on that have been taken out of context in the past so I'll leave my role on that one there," he says modestly.
Whatever his role, Waley-Cohen is clearly a modern-day maverick, a man for all seasons.