[jefftk]

> Most startups only give you 90 days to buy your options once you leave. After that, they expire and revert back to the company.

This is the real problem here. While this used to be standard, many startups have started offering employees the maximum ten years allowed by the IRS. This is something to consider when joining a company: if they're not willing to give you the full ten years, why not? More: https://triplebyte.com/blog/extending-stock-option-exercise-... https://zachholman.com/posts/fuck-your-90-day-exercise-windo...

[jrdngonen]

Worth noting, even if you have an extended exercise window (i.e 10 years), your ISOs will turn into NSOs after 90 days since your departure (and thus have a different tax treatment!).

[monitorman]

In addition, the spread can potentially get larger and larger with time, increasing the tax that you must pay to exercise.