The most dangerous mechanism to watch for is
Participating Preferred stock. In a standard "Non-Participating" deal, the investor has a choice: take their money back OR convert to common stock and take their percentage. They cannot do both.
"Participating" stock allows them to "Double Dip": they take their money back off the top, and then legally turn around and claim their 20% share of what is left. This dramatically lowers the payout for everyone else, especially in early-stage deals. See our
pre-seed specifics guide to see how this impacts early rounds.
Liquidation preferences are a "success tax". They only matter if you have an exit. You can have a perfect 1x Non-Participating term sheet, but if you fail to build a product people want—if you fail to generate revenue — this entire checklist is a moot point. You will simply liquidate with $0 regardless of the multiplier. Secure the revenue first; protect the exit second.