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At the very least, wait till Jan 1. That gives you an entire year for the stock to become liquid / sell.

More than a year - the tax won't be due until April 15th of the following year. This will give you time to hold the stock for a year (getting long term capital gains rates when you sell).

Really though, talk to a CPA.

That's actually not the case, estimated tax is due quarterly (ex. for income in Q1 of 2016 for which your employer doesn't withhold taxes, you have to pay estimated tax by April 15, 2016).

But yeah, definitely talk to a CPA.

It looks like if you have at least 110% your previous year's tax withheld and don't have self employment income you do not need to pay quarterly taxes.

https://turbotax.intuit.com/tax-tools/tax-tips/Small-Busines...

I can't find the actual IRS publication that says this, though.

Uh, that's a terrible idea. Don't exercise any options you don't have a plan right now for covering the taxes, especially if we're talking about millions as the OP says.

It's a much better idea than exercising the options on December 31, then having the tax bill come due April 15.

There's no way in which "exercise millions of dollars of stock options and hope that I'll be able to cover it" is a good idea. Merely increasing the runway doesn't fix the problem.

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