Regarding, liquidation preferences…

Employees (not just founders) can also benefit from having a basic understanding of how the ‘preference stack’ may affect them in the long term. If you’re joining a high-growth, VC-funded business then your options may well end up being worth considerably less than you thought they might do when you originally started. This is important if those options are a big part of your overall compensation negotiation.

As Scott argues in this great post, “If your company has raised a lot of money with high liquidation preferences, you could argue that your salary and/or grant should be larger to account for the increased risk of your shares being worthless.”