I had a company offer to arrange a purchase of some of my (non-public) stock as I was leaving. They knew of an investor that wanted to own more shares and brok

I had a company offer to arrange a purchase of some of my (non-public) stock as I was leaving. They knew of an investor that wanted to own more shares and brokered a price that was well above the most recent 409a, so I was able to exercise everything and sell off exactly enough to cover the tax consequences of my "gain." Not only did it let me exercise options to get stock without having to come up with a bunch of cash, but it gave me more confidence that I actually wanted the stock. Very cool move on the company's part, in my opinion. I have no idea how common this is.