The market solution here seems to be the companies poaching those employees giving them, as a hiring bonus, enough cash to exercise their shares. Not sure what would make that workable, or if it's even a big enough problem to demand such a solution.
It's not just the exercise price, it's the tax bill at the end of the year...
If you exercise upon getting hired, there is no tax bill, because there is no spread between FMV and your exercise price. There's only a tax bill later, upon liquidation.
Many (if not most) early stage companies won't allow you to do this. They claim that the "legal costs" are too high. When asked how much it is and offered to cover them, I've been met with blank stares.
I've been met with "but if you quit without having vested all your shares, we'll have to pay you back at FMV!" - and this was a CEO that said this. Staggering ignorance w.r.t. equity.
Is that a thing? I didn't know options can expire, what kind of an expiration date do they have?
Yes; options often expire 10 years after issuance.
It's common for companies to have a 90-day window to exercise your options after leaving the company. There are some friendlier companies with longer exercise windows. See: https://github.com/holman/extended-exercise-windows