Your question is too vague to apply the rule. Let me give a concrete example: I had a business relationship (he was an investor in my company) with Henry Burk

Your question is too vague to apply the rule. Let me give a concrete example: I had a business relationship (he was an investor in my company) with Henry Burkhardt III [1]. He was, by anyone's definition, a serial entrepreneur. Very rich. Very successful. The following example comes from watching him. The setup: you and other shareholders control the board. Do you: 1) use your position to dramatically dilute less powerful founders and employees, or 2) be fair and keep their relative percentages commensurate with their contribution and value? Henry famously did #2 repeatedly. I don't have the stomach for it, so I've chosen #2. If my company is acquired, it will mean quite a lot less for me (and some other people). Is that stupid? Henry would've said yes. To give you an idea of his ethics, see [2]. And, let me be clear: the people that Henry diluted were key to his success, it's just that he didn't need them anymore. Once the invention was made or code was written, their importance could be minimized without doing harm to the business. [1] http://en.wikipedia.org/wiki/Henry_Burkhardt_III http://en.wikipedia.org/wiki/Henry_Burkhardt_III [2] https://www.sec.gov/litigation/litreleases/lr14895.txt https://www.sec.gov/litigation/litreleases/lr14895.txt