Startup equity at seed, Series A, and Series B: what to ask before you sign

Cash is easy to compare; we publish what startups pay straight from their own postings. Equity is where offers are won and lost, and where companies count on you not asking. You do not need a finance degree. You need eight questions and the nerve to ask them. One note before the list: this is general education, not financial or tax advice, and the tax pieces are worth an hour with a professional before you exercise anything.

The eight questions

1. 01How many fully diluted shares are outstanding? Your grant means nothing as a share count and everything as a percentage. If they will not give the denominator, that silence is the answer.
2. 02What is the strike price, and when was the last 409A? You profit on the spread above the strike. A 409A older than a year, or one straddling a new round, changes your math.
3. 03What was the preferred price last round? Preferred minus strike is the paper spread today. It is also the cleanest way to sanity-check the company's own optimism.
4. 04What is the vesting schedule, and is there a cliff? Four years with a one-year cliff is standard. Anything backloaded (10/20/30/40) is a retention trick priced against you.
5. 05What happens when I leave? The post-termination exercise window is the single most engineer-hostile term in standard paperwork: 90 days to find the cash or lose the options. Companies offering 7 to 10 year windows are telling you something good about themselves.
6. 06What is the liquidation preference stack? At 1x non-participating, investors take their money back before common sees anything. Above 1x, or participating, your equity is worth less than it looks in every outcome short of a blowout.
7. 07Can I early-exercise, and does an 83(b) election apply? Early exercise plus a timely 83(b) filing can dramatically change tax outcomes. The filing deadline is 30 days and unforgiving; this is the question that most needs a professional.
8. 08Is there any refresh or evergreen policy? Your initial grant decays in percentage terms with every round. Companies serious about keeping senior people have an answer.

How the answer changes by stage

Seed: the grant should be measured in tenths of a percent, the strike is pennies, and the whole bet is the team. Negotiate percentage, not share count. Series A: the company has a 409A history and a real preference stack; ask questions five and six hardest here. Series B and later: grants shrink, cash rises toward the posted bands, and the equity conversation becomes about refreshes and secondary opportunities rather than the initial grant.

Red flags that end the conversation

• Refusing to share the fully diluted count after an offer. You cannot value what they will not denominate.
• A 90-day exercise window they describe as non-negotiable while calling you a future owner.
• Vesting schedules that backload, or cliffs longer than a year.
• Equity pitched at an internal valuation with no 409A or round price to anchor it.