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I'm sure this is referring to the expected value in something like say, a dice throw. If the chances of winning when picking a certain number are 1/6 and the payoff is 6x the investment then the expected returns after a large mount of attempts are known and would be zero. I'm sure this is widely applicable in gambling.

Exactly the right term to use: Expected Value. If we have 1/6 chance of winning and each win gives us 6x, we have an EV of 0.

Poker is a great game to learn to understand EV/variance.

I wonder what the expected value of entrepreneurship is?

I rather suspect it is significantly negative, because most new businesses fail and the venture capital system means gambling with someone else's money.

Not to mention the rules are known in gambling, such as required minimum bets. Business has no such courtesy. The criterion is worthless if your small bets always result in failures because you need capital to get going.

If the preconditions arent met but you are sure they are, yes.