You could? There's no reason you couldn't do $50,000 with bets of $10,000. The point is you get 5 guesses before you lose. The bet sizes don't really matter.
They matter. I could play a game with negative expected value just for fun, if this negative expected value is not too negative. Or not for a fun, but to let Ballmer win to make him feel himself winner, to make him feel superior, hopefully it will help me to get what I want from him. To lose a game gracefully is a manipulation device, especially if the winner doesn't suspect, that you lose on purpose. And, the stories I heard about MS suggest that Gates, Ballmer and all those gray beards of MS were very competitive, so they are probably much more susceptible for this particular bait. $1 is a very small price for such a tactic. But $10,000... it depends on what I'm hoping to win, and on my detailed understanding of my further steps and probabilities of their success.
Life is more difficult than math abstractions of life. No one yet managed to mathematically describe any social situation to such level of details, so you could blindly believe your equations, like you do with physics.
The bet sizes here do really matter, because they are selected to ensure that there is no risk of ruin. Ballmer asks about playing the game once at a bet amount that anyone doing the job interview can cover.
