TLDR: Your exec team and investors (the board) can monkey around with any non-IPO acquisition to make sure they get paid before you as a regular employee. 1)

TLDR: Your exec team and investors (the board) can monkey around with any non-IPO acquisition to make sure they get paid before you as a regular employee. 1) They can put a "deemed liquidation" clause in the company's legal docs so that sales are treated as liquidations. Therefore the preferred stock gets paid before the common stock, making investors whole. 2) Management will negotiate a retention agreement despite the fact that the common is worth 0 to get themselves paid.