If you woke up tomorrow and discovered you had all the money in the world, what would you do? Would you still go sailing, or would you get a powerboat? The appeal of a powerboat is pretty obvious. A bit like a car, it will get you from A to B in fast and predictable fashion. So why not get one of those? But, if you’re already a sailor when you strike the imaginary jackpot, I suspect that you wouldn’t give up on sailing. I’d wager that you’d probably do more. And you’d be in good company. For an inefficient form of transport that is rarely capable of delivering you from A to B in a straight line, and almost never delivers you to your destination ahead of time, it’s a remarkably addictive way to waste time. And yet it has led to a lifelong addiction for some of the wealthiest individuals on the planet. Ernesto Bertarelli inherited his father’s pharmaceutical business and, as well as continuing to grow the business very successfully, the Swiss billionaire also found time to win the America’s Cup twice as the founder of Swiss team Alinghi.

His arch rival for the Cup, Larry Ellison, built up the Oracle software empire from scratch to the point where he is regularly inside the top ten richest people in the world and for a brief moment a few years back even toppled his other arch rival, Microsoft’s Bill Gates, from the top spot. Ellison is a larger than life character - owner of ex-Soviet fighter jets and various other billionaire toys - and it’s even said that Tony Stark, the Marvel superhero Iron Man’s alter ego - is modelled on the San Franciscan. The rumour was given further credence when Ellison actually appeared as himself in Iron Man 2.

Ellison has been a long-time sailor, a winner of big offshore epics like the Rolex Sydney Hobart Race and these days best known as the owner of Oracle Team USA, current holders of the America’s Cup. Founder of another software giant, SAP, is Hasso Plattner who has enjoyed his fair share of multimillion dollar superyacht cruising and racing but in his sixties discovered the joys of the 505 dinghy, retail price, around $30,000. Ask Plattner about what he’d do differently if he was given his time again, and he’ll tell you that he wished he’d discovered the 505 sooner in his career.

I don’t think Plattner’s experience of small boats is that unique. It’s just that he’s had the privilege of trying all kinds of sailboats, and powerboats for that matter. The formula that he discovered is that, for many of us, the fun that you have on a boat is inversely proportional to its waterline length. So, before you trade up from your Laser to a TP52, think about it a while longer. Just because a boat is more expensive doesn’t mean it’s going to be more fun. And just because a powerboat can get you from A to B without having to zig-zag your way there and making you late, don’t necessarily expect it to bring more joy to your life. If you’re already sailing, and you already own a boat that’s only worth a few hundred or thousand pounds, just take a moment to remind yourself that for some of the wealthiest people in the world, life doesn’t really get much better than pootling along in a simple sailing dinghy.

- Andy Rice

Andy Rice is a successful sailor who started his career in journalism in 1992. He writes write regular columns for Seahorse, ShowBoats International, Yachts & Yachting and Boat International.