You've raised three SAFEs over the past 18 months — a pre-seed, a bridge, and a quick top-up to extend the runway. The terms felt straightforward at the time. Now your Series A is closing in six weeks, and your attorney just sent over a cap table model that left your co-founder staring at the screen in silence.
The math isn't wrong. It's just the math you didn't do when you signed the SAFEs.
Founders increasingly use Simple Agreements for Future Equity (SAFEs) to raise early capital without immediately negotiating a valuation. This flexibility is genuinely useful. But multiple SAFEs accumulated over time — often called a SAFE stack — can create significant, sometimes shocking, dilution when they all convert at once. The good news: with advance planning, much of this dilution is manageable.
