Everybody views money differently, in large part based on the way they grew up. Some people are comfortable talking about it. Most aren't. Some are comfortable only in certain situations.
I once heard the CEO of Authentec speak, when he received an Entrepreneur of the Year award. Someone asked him the best way to raise money for a startup. His response? Beg.
I've had several people discuss startup opportunities with me lately, and they always want to know how to raise money. It got me thinking. Do entrepreneurs sometimes fail because of the way they view money? What if you are comfortable asking friends and family, but feel uncomfortable pitching to angels and VCs later? I'm actually the reverse. I'll pitch to strangers way before I would ask for money from my family. It just struck me today how strange that is. It's backwards of the way most people do it. (Although some people will say not to ever go to family because of the risk of straining those relationships if you fail). I wonder if any entrepreneurial research had looked at how a person's psychological views of money related to their effectiveness at raising it.
Another thought – why is it that wealthy people that would give 10s of thousands to charities would never invest in a startup because it is too risky? It seems like it could be considered economic philanthropy.