Information assymmetry, agency in impacting equity value, difficulty in valuing options, endowment effect and cognitive biases all come into play here. Early stage options are different than RSUs. Usually better to look at scenario analysis of outcomes to value them. The value is often lower than the RSUs you would get in a public company but the outcome can be much better if the company 10xes.
I would move to a smaller company to 1) get greater responsibilities and experience in new areas that my current job doesn’t allow, or 2) work with an excellent new team in a promising new industry, or 3) get better work life balance by reducing commute/travel/hours etc. If none of the previous things are true, then don’t leave your current job just for the potential of startup equity turning into something substantial. You might not stay there long enough...
Expect paper equity from startup to be from 20x (early stages) to 2x (pre-IPO) bigger to compensate for risk that it's not going fly. There are 6 months+ cooldown period even if you join 1 week before IPO. Stock can easily can go down during it.
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There are 6 months+ cooldown period even if you join 1 week before IPO. Stock can easily can go down during it.