[zamfi]

You probably know this, but commonly you can exercise options and keep the underlying shares past the original option expiry date. (Of course, you need the cash—and confidence in the business—to do this!)

[S201]

The problem is that after paying the strike price to exercise and the subsequent taxes I'd be underwater based on their current FMV so it doesn't make sense to exercise them. Plus I have very little confidence left in the business.

[hackernewds]

So then why would Carta acquire underwater equity?

[S201]

It was a joke.

[zamfi]

But wait, taxes are only on the difference between strike price and FMV, so if it’s underwater you could take it as a capital loss and net out ahead!

/s