Why not? Options are usually "in the money" so if you don't exercise them you are throwing away money which you already earned.

This is true for liquid options. Startup options are not liquid, there is a chance they’re illiquid until the company folds or is bought- and in an acquisition of a struggling company they’re likely to prioritize higher share classes before common stock gets to see a piece of the price.

They’re extending the exercise window to 5 (or more years) for laid off employees. There’s no reason not to at least hold on to the options until IPO.

Perhaps I’ve had bad luck but I’ve never had options that would have been worth anything.

That's regular luck, or at least not bad. Options worth > $0 is an occasion of very, very good luck.

> Options worth > $0 is an occasion of very, very good luck.

Why do you think that?

It doesn’t require ‘very, very good luck’ for most companies shares to not collapse.

If you work for a big company like Oracle or IBM your options have cash value no luck needed.

> Oracle or IBM

What? These are public companies; short-dated OTM options have > $0 value only in volatile markets. But these companies don't pay employees in options.

Options as tech startup employee compensation vs. Options in general

That's expected. Most startups never recoup the funding they raised.

Patreon is not publicy traded, so your ability to sell any RSUs is very limited.