Tech Millionaires Plagued By Very Difficult Rich-People DecisionsS

It is rough out there for tech executives. Positively awful, and the better off a plutocrat is, the worse things get. Or at least that's what I gather from some recent headlines in the wealthy business man's newspaper of choice, the Wall Street Journal.

"Potential Windfalls Loom for Some Top Executives," the paper reported yesterday. Windfalls "loom?" How dreadfully ominous. And then today, "Yahoo Puzzles Over $4 Billion Tax Break." Why, a nine-figure jackpot does sound like quite a conundrum.

So, here's what it's like to be a very geeky one percenter in 2012: First you must deal with the (apparently) frightening prospect of getting some of the $780 million in stock bonuses vesting in the first quarter of this year. Apple's Tim Cook, who oversaw the company's increasingly embarrassing child factories in China, is expected to take home $96 million worth of equity, if he can bear it.

Then there are bewildering choices like the one confronting new Yahoo CEO Scott Thompson, who must decide whether to push forward with a $4 billion tax dodge, joining the ranks of techy tax avoiders like Google, Apple, Microsoft and Cisco. If he does, the IRS might say "no" (they have prescreening process for tax cheats, apparently), and if he doesn't, Yahoo will have to pay its taxes like a commoner. What a "puzzle."

"Although tax experts say that the IRS has generally greenlighted such transactions," the Journal reported, "this situation could draw scrutiny because of the deal's size and the multiple parties involved." Oh, those Yahoo guys are surely sweating bullets. Real tough pinch they're in. Sounds like they have a lot of hard thinking to do, about whether to have their accountants mount a multi-billion-dollar tax avoidance scheme, and whether or not the IRS will pre-approve it. Keep them in your prayers, everyone.

[Image via Roman Sigaev/Shutterstock]