People who work in the start-up industry have to be over the top optimistic and always lean toward the positive possibility rather than the negative probability. You are a founder. You believe and you must make plans and act on this optimism or you never get anywhere.

EXCEPT WHEN FUNDRAISING.

Of the 1 million and one problems a founder faces, some have dependencies and some do not. If there are no external dependencies, taking the optimistic approach is the only way to go. However, if there are external dependencies largely out of your control, like getting a VC to a yes, you are best served by being pessimistic. This is not natural for people used to changing the world against all odds, it can be painful, but it is the best approach.

Basically you can assume going into a meeting that the answer is no, since more than 99% of the time the answer will be no.

Exactly. The balance of optimism and pragmatism is a fascinating one in startups and entrepreneurship.

I think investors regularly use the entrepreneur's optimism against her or him.

How so?

Not giving you an answer until someone else does.