Ask HN: Best Stock Options Guide

1) Set aside an option pool (e.g. 10% of issued equity) so you don't need to go back to investors to approve each new grant.

2) Think about how employees value equity. If someone values equity at zero, or much lower than how you value it, then maybe pay them x more cash instead of equity (where x>0).

3) For senior hires or others who you expect to contribute materially to the success of the business, make sure the equity is meaningful.

4) Everyone's equity (even some of yours) should vest over time (e.g. 4 years). Exception: equity which is paid for with cash money, like external funds.

5) Think about what you will do if someone underperforms, but isn't terrible. If an employee is doing their job well enough that you don't want to fire them, but much less well than when you decided how much equity to grant them, what will you do? (Distinguish this from the case when the equity rises in value significantly, so everyone's vesting looks generous. That's great, and fair compensation they took on as early employees.)

6) Get proper advice about the tax stuff in your country/state. Google stuff like 'qualifying options', '409a valuation', and the different tax implications of granting options vs. restricted stock vs. stock with a repurchase agreement.

Those are the general things to consider. Contact details are in my profile if there's additional info you can share, which you can't post here.