[tptacek]

This is a great comment (note that while I'm a total cynic about the prospects of holding private company common stock as a non-employee, I did just lose out on a high-multiple investment opportunity by walking away from my last employer's options).

I just want to add though, presaging some people's thoughts that "they really trust the founders" and whatnot, that oftentimes the founders have little say in the outcome for non-employee stock holders. The VCs are usually calling the plays with regards to exits and valuations.

It's also worth noting that at some point during the life of many successful companies, the founders incentives are going to begin radically mismatching those of the employees; their outcome on a modest-but-successful exit will be life-changing, and the utility of the extra money they make on an exit large enough to change early employee lives won't be worth the risk. They'll want to exit as soon as they can.