Nobody would give you preferred stock, which is why you need to demand an absolutely absurd premium on the amount of common stock that they offer.

Also, it generally doesn't need a new class of shares, just a vote by the board.

Edit: Just to clarify, if you want to hire a mercenary, you can't do it expecting that they will take the same value of your stock that your true believer investors took without any of the guarantees that your investors got. They are investing time into your company and you need to make it worth it.

This just doesn’t make sense though. A company is going to have some standard bands of compensation, and if you demand something way outside of the bands based on your own feelings of stock value, they aren’t going to hire you no matter how great you are. Part of the reason companies can give generous stock grants are precisely because they are the lowest tier of stock.

This also is a stupid thing to bargain: if the company keeps growing, preferred and common will be worth the exact same thing. So instead of trying to extract better preferences on the stock (which you won’t), join a fast growing company and leave if it stops growing fast.

> A company is going to have some standard bands of compensation, and if you demand something way outside of the bands...

If you're joining early enough to get enough equity to matter, you're early enough that they don't have standard bands. You can absolutely negotiate.

> if the company keeps growing, preferred and common will be worth the exact same thing.

Only if it ends in an IPO. An acquisition, even a "successful" one, can easily end up with the preferences kicking in.