

Ask HN: My options are about to fully vest, should I purchase the shares now? - TheBiv

Howdy!<p>I&#x27;ve been with this company now just close to 4 years, we have raised double digit millions and are not immediately going to sell the company; and I am not planning on leaving.<p>I am wondering if there is any reason that I would purchase the shares now or just wait until we either sell or I leave?
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bluejekyll
This is a hard questions to answer. If you exercise now you can convert that
stock into shares that after a year will change from short term to long term
investments and thus lower your tax liability on the difference of the option
price and the market price.

But, you will be risking the money that you use to exercise those options, ie
if the company doesn't exit, or exits where only the preferred stock is payed
out, then you will lose all of that.

IMO, this risk is not worth the tax savings, unless you have a ton of money to
spare, in which case why even care about the taxes. Hold the options until
there is a real market for them, it's the least risky option.

~~~
bluejekyll
And then I just read this which contradicts my above statements a bit:
[https://gigaom.com/2011/06/05/5-mistakes-you-cant-afford-
to-...](https://gigaom.com/2011/06/05/5-mistakes-you-cant-afford-to-make-with-
stock-options/)

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mtmail
bluejekyll is right that long-term you move the tax burden from income tax to
capital gains tax which has a benefit (in my opinion not benefit enough).

As a shareholder of the company you can't sell whenever you want, e.g. there
might be restrictions that if you find a buyer all other shareholder have
equal right to sell to that buyer. You can't assess the value because private
companies rarely assess themselves (tax reasons, strategic reasons) and who
you're selling to can also be limited, e.g. by requiring full board approval.

If the company is in trouble at some point then investors and shareholder
watch each other (in the negative sense) and it's get political who can sell
and how much. In worst case you have to deal with power play in the board, an
in-transparent situation where you might not even know all the players.

As you can see the risk increases. Only worth it if you want to their get more
control (board seat or get your voice heard) or if you want to keep stock
rather than stock options in case you ever get fired or similar event (because
you'd loose the options usually).

