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baq • yesterday at 3:31 PM • 1 reply • view on HN

Why? Whatever's vested is yours.


Replies

manquer • today at 12:28 AM

Not exactly? Options vested is yours to exercise within typically a 60 day[1] window or they expire if you are no longer in the employ of the company.

Exercising your vested options is a taxable event[2] and requires you to upfront some cash to buy the stock depending on what price(and rounds) your options were issued at- this price usually is considerably less than enterprise value of the same share lets say it is $1 and FMV of $100 at the time of issue, however even just $1 for vested 500,000 options is still $500,000 now.

For this simple[4] scenario you need $500,000 immediately to exercise the options into stock before they expire and about ~$13.86M by April to own[5]all stock if ends up say trading at $200 you are worth $100M then.

There are all kinds of funds who would loan you the money or buy the stock off you now on the secondary market, but vested options does not mean owned stock, and selling quickly after exercise is much higher tax under some scenarios.

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[1]Some companies have generous(relatively) terms ex-employees to exercise up-to 5-10years later; but it not default in the industry.

[2] This close to IPO that should be relatively small risk; i.e. if the company pulls IPO you still have to pay tax end of the year; if you exercise them.

[3] NSO/ISOs work quite differently, and options vest monthly in most corps and there are lot of creative structures out there; so cannot say how it would be for ANT employee specifically.

[4] Simple - because there usually more than singe 409A valuation and more than single set of options plan issued and plenty of other complex calculus only a finance expert would advise on.

[5] You could sell the shares to pay the ~14M-ish in tax but that could be disqualifying sale(2 year after grant, 1 year after exercise) for ISO meaning you will need to pay effectively 40M tax on your 100M holdings versus only ~$27M otherwise, so you would a take loan against the shares rather than sell to pay the tax.