If they don't have the money they can take a loan (maybe hard without a job) or try to raise it (lots of people will be happy to invest). Let's not forget that many of these individuals have been making top dollar. Airbnb is known to be very competitive, even with FANNG level salaries.

I don't see it as a tough choice. Airbnb will IPO, it's just a question of when. It's a safe investment to make. This is a company operating all over the world that had $4.3B in revenue last year. If not COVID-19 they would've probably IPO'd very soon. They will get through it.

Their 2020 revenue will likely be less than a quarter of that. And 2021 might not be much better. They have a struggle ahead.

It would be nice if you could just hand over a percentage of the options to the government as a tax, instead of having to pay in dollars at a guess of the value.

I am surprised that isn't an option it certainly is in the UK

I'd expect the options might be under water based on recent funding announcements. Probably still expensive to exercise, but I can't see how there would be a tax liability if they are under water.

i’m not super in the know here, but why would corporate financials be relevant to the tax obligations of individuals?

It's pretty much impossible for us to say in this case since the terms weren't disclosed that I know of. They've been described as debt and equity. It's reasonable to assume the equity component would imply a certain valuation, and that valuation could be down from previous valuations.

If you received options at a strike price at the peak valuation, then the current valuation may be below that level.

Yeah it's going to be a hard decision to make for a lot of these people, especially given some of the bad press that these kind of gig factories have been enduring.