It is costly and only works a few times. Investors will also be (rightfully) nervous of any possibility that you may not be able to stay in the country.
However as you say, if you are looking for funding then it might be a problem, they don't say it but you can perceive it.
I'm wondering if getting the investor money helps to get your visa.
Does anyone know cases like that?
I think that if you get too complicated with your stories that's when you can get into troubles in customs.
EDIT:
I never stayed longer than stated on the I-95 btw
So it's the requirements + strong proof that you will create jobs in the US or your are a great scientist, artist, etc... or you have a lot of money to invest.