Given the huge information asymmetry problems between employees and employers introduced by options, (see the comment by 'babababa for a good list of things to

Given the huge information asymmetry problems between employees and employers introduced by options, (see the comment by 'babababa for a good list of things to ask, that not all companies will want to share) - would it just be easier to have an agreement like "if the company raises $X million, employee gets a bonus of $Y"? (you could have different X's and Y's for different tiers of round e.g. 20K bonus if we raise 10-50 million, 100K bonus if we raise 50 million+, etc, and maybe a different one for "company goes public"). You lose the tax benefit of cap gains vs income tax, and you miss out on some upside if you're an early employee at the next Dropbox (but you're probably not one of those); on the other hand the downsides are at least quantifiable, as compared to receiving an unknown percentage of the company at an unknown valuation with unknown liquidity preferences and having unknown tax issues (83b, AMT, etc). This is literally something I just thought of now so I expect it to be full of holes. What do people think?