Wayne,
That expression seems to get a good run around the different high-risk activities these days (or at least those perceived as high risk).
I believe it started out as a mountaineering expression, talking about climbers, and I heard it on TV just the other week talking about pilots (of light aircraft).
I have to say though, it is quite a catchy expression, and in the case of climbing (I did some rockclimbing for a number of years), it's certainly something that helps temper the urge to go for that risky move when you're not well protected.
Quite coincidentally, a guy I occasionally climbed with who was very experienced but used to really worry me with his tendency to flout the laws of gravity, eventually killed himself while out climbing (fortunately not while I was there), and another guy who used to be my accountant and was an amateur pilot also killed himself some years ago while flying (although in his case I have no idea whether he was a "bold" pilot or not, or exactly what caused the crash).
And even your trading version might be close to home for me. An ex-work colleague (by "ex" I mean he left, not died
) who, like me, managed to get quite a bit of cash through employee shares that shot up in value after a merger, public float, and later buy-out, I recently heard that he'd lost most or all of it somehow. I haven't heard exactly how, but I do remember him saying just before he left that he was playing around trading options on the US market. From my short discussion with him at the time, I got the impression he had little idea about what he was doing, and I have a suspicion that this may be where the money went (although I could well be wrong).
Cheers,
GP