> The CEO of Keurig just sold a bunch of shares last week to pay the taxes on his options. Not being able to wait a week cost him close to $1,000,000.

I highly doubt he's crying.

You should look into put options. They're how you short a stock without a massive downside. If the stock goes down you win, if the stock goes up you lose nothing, and all it costs is a small up front premium.

To say you "lose nothing" seems a strange way to describe an option you have to pay for and which has no value without clearing the contract cost.

> To say you "lose nothing" seems a strange way to describe an option you have to pay for and which has no value without clearing the contract cost.

Well you can only lose what you put in and the option itself costs a fraction of the share price. Put option owners were certainly feeling a lot better today than short sellers (though call option owners were feeling best--some lucky owners of the Dec 11 65 calls are up 239900%!).

Can you please provide some examples with real numbers on puts... I do not understand them. Thanks -- and Apologies for not turning to google, as opposed to asking you to ELI5

Puts are, simply put, insurance (pardon the pun). You pay a premium for the option to sell the stock to someone at $X at a future date. Let's say you think that AAPL is going to go down in price. You could for example buy a put option to have the option to sell AAPL stock at $118.28, in 6 months, to the person who sold you that option. If the stock goes up, you don't exercise the option. If it does, the option writer (guy who sold it to you) pays you the difference between the stock price at that time, and $118.28. The only cost to a put option is the premium (maybe a few dollars, depending on the forecasted price of the stock and forecasted interest rates) that you paid at time 0. So if you paid $10 for the option, and the stock goes down to $105, your total cashflow is +$3.28. If the stock went up to $200, your total cashflow is -$10.

This is essentially true, though the pricing is quite a bit more complex (implied volatility is important in pricing and that can swing wildly).

The tl;dr is it's a way to be short a stock with more limited risk, but with the added variable of having to be right on timing.

> Also, the timing is only applicable to European options which expire on a specific date. American options have no expiration date!

Umm, American options still have an expiry date. They can be called earlier than their expiration date, though unless there is a dividend to be paid, its never advantageous to do so.

But American options absolutely have an expiration date. They wouldn't make sense otherwise.

I mean at price would you sell someone a put or a call if they could wait forever to exercise it?

No matter what implied vol you put on the underlying, you would still have to price it at infinity wouldn't you?

My bad! Sorry about that, my brain wasn't working well yesterday... :)

If he sold immediately after the announcement he'd be in big trouble. Likely there's a lockup for a while and he wanted to sell before the end of the year.