@Ben Cook - I don't know who the board members are but my hope is that it wouldn't be anyone employed by Automattic to keep the separation their. However, I guess Matt would most likely be a board member or founder of the foundation where in the points of separation would disappear again.

Matt’s job is to provide as large of a return for his investors as possible. If he can do something on WordPress.org that improves Automattic’s revenue he SHOULD do so or he’s doing his investors a dis-service.

If that is the case and this indeed has happened before or continues to happen, then I have a problem with it. As I see it, the investors have put their money into Automattic the company which operates paid services such as TalkPress and WordPress.com. The investors should not have any say or give a damn about WordPress.org. WordPress.org should not be their concern because WordPress.org is not meant to be a money making machine, WordPress.com is. I will agree that no matter what Matt says, him being the founder of Automattic and him being the founder of a non profit entity in WordPress.org presents an inherit conflict of interest. The only way to solve that would be to choose one over the other and not do both. I don't see that happening so the next best thing is to hope that Matt doesn't grow devil horns and turn evil on us.