Buy now, sell immediately, eat the short-term capital gains tax in exchange for certainty.

westwind

There are tons of stories of people who in the last internet "bubble" excercised their options to earn long term tax rates only to see their stock go underwater--they had big tax liabilities. I would sell a portion now, and hold a portion to sell later. But i wouldn't exercise to hold for a year!

jesse

You've got more options for the long-term.

RedHotWings

If it keeps you up at night... let it go.

merlin

Getting stuck with AMT and tax complications for years to come is a major pain in the ass. I know this from experience.

hanopycanopy

If property value goes down, you'll be in trouble

dzm

Your stock is IMHO quite overpriced.

eisenbud

Are the ISOs? For NSOs if you want to wait a year, waiting a year and flipping is probably even better, but I assume you wouldn't be asking this if they were.

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