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When to take money from Friends for business?

I was on the phone today with a buddy of mine that did pretty good during the .com bubble, and we were talking about somethings including my frustration in the pace of some things that have been happening lately. This is one of the few times in my life that I wish I had a lawyer in the family. I mentioned jokingly what we could do if we had enough bankroll to quit the day job and hire some people.

He shocked me, and said sounds good let me write you a check. Over the past 3-4 months I have had some good friends tell me the same thing, but I am that stage in my life where good friends are hard to come by, and I really get this queasy feeling in the bottom of my stomach when someone is potentially holding out a check with a significant amount of their savings attached to it. I am quite confident in what we are doing but getting money from bank is one thing and getting money from friends is another.

I think I would have nightmares worrying about their investment. If something happened I would feel guilty forever. I am sure some of you have been down that road. How have you handled it?

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