How much cash does Github have to keep the last 50 or the next 150 feeling special? This is where managing the business starts to get really hard.
I'd assume that the GH founders and first tier employees have probably each banked about $1M so far. A Google acquisition valued at $30-50M would set all of them up nicely and let them move on to other endeavors.
In my opinion, only a very generous profit sharing program or a planned acquisition strategy explains the complete lack of rogue employees blogging their gripes. Keep in mind all the drama at Twitter when it was small.
I don't disagree with that at all, but the cynic in me feels like even with such an amazing team the org stuff gets harder (cash aside) as the company grows.
However, GH has always exceeded all of my expectations in every possible way, so good luck to you guys whatever path you choose.
Remember: "optimizing for happiness".