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Comment by chollida1 | Hacker News Reader

Founded in 2007. I think its fair to say that dropbox is one of the more successful starups around. So when you join a startup, I think its reasonable to ask them for either:

- long option exercise periods after they leave the company, like the 10 years that has been thrown around before.

- or written authorization to sell vested options on a secondary market at the market price

- or plan to stay with the company for 10+ years, remembering that you probably can't sell for the first 6 months of going public.

Because ifyou join a startup where some of your comp is in the form of options, this is what you are signing up for.

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Or you could just exercise your options within the 90-day window. Me personally I'd much rather lose a fixed sum of money, then realize I missed out on being a millionaire.

Why exactly would you prefer that over a longer exercise window? What are the odds that the startup you joined 2 years in will successfully exit (even 8 years later in the case of Dropbox)?

Wouldn't exercising your options be a taxable event? Without a way to liquidate them you are stuck with a big tax bill and still potentially worthless share.

Then you might owe an absurd amount of money to the tax man. As far as the IRS is concerned, you need to pay the AMT on the difference between the price per share of Dropbox at exercise time, and your strike price. If you joined before Dropbox went through a couple rounds of funding, this tax bill could easily be in the hundreds of thousands, or even millions of dollars. You need to get that money from somewhere, but you can't sell on the secondary market, so what do you do?

Unless you do an 83b election.

Can you do that for ISO?

yes, possible to early exercise an ISO and then elect 83(b).

however, if you definitely want to early exercise, NSO is preferable since an NSO has more favorable tax treatment wrt to timing: for NSO, long-term capital gain treatment starts one year after exercise, whereas for an ISO you need to wait both one year after exercise AND two years after the option grant date.

so, specifically: if you early exercise an ISO on the day it is granted, you have to wait 2 years for LTCG treatment vs. with an NSO, you only have to wait one year after you exercise, even if it's on the date of grant.

Yep, you're basically rolling the dice.

It gets worse if you're at a unicorn startup that doesn't exit well, because then you may have paid thousands in taxes on stock that is essentially worth pennies:

http://www.nytimes.com/2015/12/27/technology/when-a-unicorn-...

Any tax paid only for exercising options is AMT. It is refundable as AMT credits in future tax years where your conventional tax liability is less than your AMT liability. It's still bad news, and an unfortunate result for the fairly well off "little guy" in this story, but it's not as bad as it was in the dotcom bust in an era before the AMT credit existed.

Yep this matches my experience with unicorn stock options. It was a pain to come up with the exercise price & AMT upfront in the first place but the AMT was refunded in full the next year.

I'm aware. I've already paid taxes on options that are underwater. I just use my paycheck to purchase the options.

The tax liabilities on the 'paper gain' could easily go into the six figures. Not sure if many people would be able to do that, let alone want to.

Giving a pile of money to the company you just decided to leave and another pile of money to the IRS gets old after a couple of times. How many lotto tickets do you buy every week?

I believe the places I work are going to be successful, otherwise I wouldn't work there. Yes there's a lot of luck involved, but it's not just picking numbers at random.

What about when you join a company that is promising, but then starts going downhill and you want to leave. That's the time you'll need to write the check, and it's hard to feel good gambling on a company you are leaving

Just have money bro! So obvious!

If you've been there for 10 years, then the taxes on those options will murder you if you choose to exercise now. I think ideally, that you incrementally exercise over the period of time of your stay. Bigger risk since you won't be sure of the future of the company as you do now but the difference in the strike price and the value that you exercise would be smaller which would hopefully mean less tax. I think the idea is to exercise your options when the current value of the stock is not too far from the strike price granted.*

* I am not a tax adviser.

The question I wonder is this:

Of the first 10 non-founding engineers—i.e. those who almost certainly took a salary cut in exchange for equity—how many will be able to retire off of an upcoming multi-billion dollar IPO?

Retirement is a very hazy metric, so let's say How many have at least 1/3 of a 1% stake? Remember these are the people were with the company at its most fragile time and this is a massive success.

I have no insider information, but based on what I know of other YC companies thus far, I'd say that the founders almost certainly have double digit percentages and that less than half of the first 10 engineering hires have even a third of one percent.

On a related note, I wish Andrew Mason a roaring success with his post-Groupon endeavors.

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