This sort of misses the forest for the trees, although neat application. Ballmer's argument is essentially about tail risk. Expected value is absolutely not a good way to make bets if you value survival, because you only get one shot. Same reason you wouldn't go all in every time you get a poker hand that's "expected" to win. Because you'll (very probably) be bankrupt in a few hands. Sure the mean is +$0.07 or whatev…
Betting more than the Kelly fraction increases the risk of ruin, especially in the long run.
https://en.m.wikipedia.org/wiki/Kelly_criterion
Note: Not saying that this is applicable in the original post's situation. It's relevant to the parent comment though, and very useful in many situations, such as investing.