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What often happens is you hold it for a while to reduce the tax burden. Then when you sell it, say you want $100k, you actually sell $115k to cover the extra 15% in taxes. (You'll end up needing a little more to cover the extra 15k, but that's easier than covering the 100k.)

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Two problems:

1) Typically shares are treated as ordinary income when they vest, so you owe tax on that no matter what you do (but the vest price becomes your cost basis).

2) Wash sale rules apply to grant vesting events, so if your grants vest monthly every sale is a wash sale.

This is a recipe to pay massive taxes though. If you have the cash you'd prefer to do an 83b election and pay the taxes when the stock is very cheap.

It's also important to note that the clock for long term capital gains tax starts at the date of exercise, so you'd still need to exercise the options, which will cost money.

That's not how a stock grant works now if they're just straight up giving you the shares, not via options. It gets taxed as ordinary income as soon as it vests, nothing you can do about it.

Okay, but direct grants are a somewhat rare condition, no? Most folks here would be dealing with ISOs.

No, ISO are terrible. Most folks would be dealing in RSU, and if they don't they are being taken advantage of.

Wow, you really have no idea what you're talking about.

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