If you have Non Qualified Stock Options that you are considering exercising here are some things to keep in mind.
There are several ways to go about doing the exercise.
The easiest and most expensive way would be to sell some of your UPS shares to cover the exercise.
The problem with this is in addition to the taxes due on the exercise you would create a Capital gain on the sale of your UPS.
In effect creating two tax hits needlessly.
Another option would be to exercise and sell enough shares ( from the option grant ) to cover the taxes and the cost of the exercise.
Ex. Grant 2000 shares at $15.00
Cost of exercising = 24,000
Taxes = $20,000
Sell 800 shares proceeds $44,000
( these numbers are fictional )
Since you would be taxed at your ordinary income rate upon exercise any way the additional sale does not incur any additional tax.
The result would be a partial sale and you would be left with 1100 shares from the original 2000.
Now if you would like to hold all of the shares from the option grant you still have an option that will avoid the need to sell UPS and generate a Capital gain, you could borrow against your UPS holdings to pay for the exercise.
You would then have 2000 additional shares but your cost basis would be much higher and one year and one day form the date of yur exercise you could sell the shares needed to pay off the loan and pay long term capital gains of 20%.
Either way you are looking to avoid generating a large capital gain and holding all of the stock if that is what you would prefer.
You dont have to pay of the loan until you decide to.
Net, Net No capital gains tax, hold all UPS pay only ordinary income tax.
You can sell when you want if at all.
Some things to remember.
The exercise is taxed at your ordinary income tax rate. ( there is no way to avoid this )
Any stock sold on the same day to from the grant incurs no added tax.
Stock held 1yr and 1 day subject to cap gains tax of 20% ( only obviously if the stock goes higher than the price you exercised at )
If any one has any question, please post em here.
By the way this only applies to Non Qualified Options not Incentive Optons the tax treatment differs for ISO.
John