I invest $100 for 20% of your venture, implicitly valuing the company at $500 . You sell for $200.
- Standard preference: I get $100 or 20% of the company ($40)
- 2x preference: I get $200 or 20% ($40)
- Participating preferred: I get $100 and 20% of the company ($140)
IMO, 1x preference, non-preferred is entirely fair. In the event the company sells for lower than the valuation, the investors get their money back first. The vulnerability it protects against is that I found a company for $0, you invest $100 for 20%, then I immediately turn around and sell for $101. You get $20.25 and I get $79.75.
Participating preferred and >1x preference are unconscionable.