:And what happens if your VP finance runs off with the mail boy and all your bank accounts? This scheme works only to the extent that I trust you will not lose my initial stake, and evidence of that would be that you would have to have much more money in it than I do.  As for the "option", it would have to be at my discretion, and thus I would only exercise it if the shares were worth less than my option price, or you are my son-in-law (which is the only time I have handled a buy-out this way). I do this kind of investing often enough that I know there is little appeal in your plan.