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You might want to talk to your company attorney about the possibility of the company buying back his shares by executing a note for the balance, rather than all cash. Maybe talk about the possibility of having the note come due upon some particular event, such as replacing the investor with another investor of equal or greater value. If the investor is hesitant to go for that option, you could talk to your attorney about the possibility of having the company make payments towards the note balance on some other future event as laid out on a timetable.

If you look in the Attorney engagement letter it probably has language about their duty is to represent the interests of the company only, and not the founders, shareholders, officers or other individuals or entities associated with the Company.

It seems like he wants to willingly pull out as employee and investor/board member, as long as he gets his investment back. So working out a solution for the payment for the shares (with the help of the company Attorney) might get the ball rolling on a solution for you guys.

Good luck with this.

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