So with Apple's stock flying so high these days, are there any investors who are actually stinging because of it? Well, sure-- anyone who bailed out way back at $25 or so is probably mourning the loss of What Might Have Been had they just stuck it out and had faith. Of course, their pain isn't anything compared to that of any investors who had the lack of foresight and the sheer, unmitigated gall to have shorted AAPL in hopes of profiting when the stock price declined; they may have lost their shirts, but hey, that might turn out to be a plus, since we hear it's mighty hot where they're eventually going.

But one guy who might be looking at the stock price with a tinge of bittersweet ruefulness may surprise you: Steve Jobs. It's ironic on at least two levels, because he's arguably the single person most responsible for AAPL's current $64 price tag, and he's also a fairly heavy shareholder himself, so when the stock price goes up, he makes money (at least on paper). So he's done his job well and made a pile of cash, too, so why the expression of wistful regret?

It all comes down to timing, basically. Remember when all the pundits were whining about how Steve made too much money, and as proof they pointed to the freakishly huge number of stock options he'd been granted by Apple's board of directors back in early 2000? Remember how Apple's stock tanked a few months later, making his options totally worthless? (Oh boy, the chance to pay $27 per share for 27.5 million shares trading on the open market for $16 apiece! Where do we sign?) Eventually the board felt guilty about Steve's actual payment being a mere $1 a year-- well, plus that jet-- and last year it offered to let Steve trade in his 27.5 million underwater options for a straight 5 million free shares of stock. He took them up on the offer, which means that he's made a whole pile of money in recent months as Apple's stock price just kept rising and rising.

But Graef Crystal over at Bloomberg did a little math; he figures that while Steve's free 5 million shares are now worth about a third of a billion dollars. That kind of cash buys a whole lotta Fig Newmans. However, had Steve held onto the options instead and exercised them, right now he'd be able to liquidate his holdings and cash out for a profit of over twice that much. D'oh! As Graef says, "Bad move, Steve. Some people may perceive you as arrogant, but based on your decision, you really underestimated yourself."

Man, way to kick a guy when he's, er, up. So why did Steve trade in those options? After all, he knew better than anyone where Apple might be in a year; maybe he just didn't want to bet on the long-term popularity of the iPod, since he'd seen the public at large pass over insanely great products before.

Either that or he was really craving Fig Newmans.