ESOPs and equity: pricing paper money
Startup equity can be life-changing or worth exactly nothing. A few questions separate the two.
Fintech offers increasingly include equity, and candidates systematically misprice it in both directions - dismissing valuable grants and treasuring worthless ones. You cannot value private equity precisely, but you can stop valuing it naively.
The questions that price the grant
- What is the current 409A / fair market value per share, and the latest round price?
- What is the total share count - what percentage does my grant represent?
- What is the vesting schedule, and what happens on acquisition or termination?
- What is the exercise window if I leave - 90 days or years?
- How much cash does the company have, and what is the burn?
The discount rules of thumb
Seed-stage options: treat as zero in your decision math. Series B-C with real revenue: worth perhaps 20-40% of paper value as risk-adjusted expectation. Pre-IPO with secondary markets: can be priced fairly precisely. Anyone who tells you a more precise answer for early stage is selling something.
The exercise-cost trap
In India, exercising options triggers tax on the spread as salary - on illiquid shares you cannot sell. Before accepting equity-heavy offers, understand the perquisite tax at exercise, not just the headline grant. This single misunderstanding has cost candidates more than any down round.