1. Underestimating Liquidation Preferences
A participating preference or multiple preference stacks debt-like liabilities senior to common equity. In typical exits, common receives $0 because preferred terms devour the entire price tag.
2. Raising Excess Capital
Oversized rounds increase the minimum exit threshold required for founders to see any return. Valuation optics should never override cap table efficiency.
3. Casual Debt Layering
Venture debt resides at the top of the priority stack. When growth stalls, senior debt drains liquidity first, shutting out all classes below.
4. Loss of Exit Control
Governance and drag-along rights can allow board majorities to force mediocre sale actions against founder alignment thresholds.
5. Failure to Model Cascades
Founders fail to explicitly run exit waterfalls at lower values ($50M, $100M) before signing financing term sheets.
6. Rejecting Early Secondary
Taking modest secondary de-risks founders, reduces board friction, and avoids full personal illiquidity wipeouts.