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All else equal, which impresses a VC more, a founder who was a middle?

A founder who is well prepared to answer all the question and his own due diligence and the hustle that has led up this day. When a VC looks to invest his or her money, it is based on the product and most likely he has made his decision before he puts a qualitative angle on the background of founder. So it dosent matter you are a c-level executive or middle manager or out of school graduate.

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