1. The day you exercise, the IRS will tax you income tax on the value between the stock's current value and your strike price. This is true even though you haven't made money from selling the stock yet.
2. If the company is still private, the stock's value is determined by the last 409(A) valuation for Common stock that the company performed, assuming that your options are for Common stock (which is very likely). The company must perform one of these valuations a year and should provide you with that amount upon your request.
3. Exercising the stock starts the clock for long term capital gains treatement. That is, if you sell the stock a year after exercising it, you will pay capital gains tax on the value difference between the sell price and the value at exercise.
Math wise:
* TP = strike price (the price in your option contract at which you buy the shares)
* EV = value of a share at exercise time, as determined by the latest 409A valuation
* SP = sale price of a share when you sell the stock eventually
* #S = the number of shares you have
* IT% = Your income tax rate
* CT% = Your long term capital gains rate
At exercise:
- You pay to exercise the shares: #S * TP
- You owe in taxes: #S * (EV - TP) * IT%
At sale
- You make: #S * (SP - TP)
- You owe in taxes, assuming you waited a year to sell: #S * (SP - EV) * CT%
Not a bad idea though lynx doesn't do a great job parsing HTML emails either, unfortunately. Turns out it's an annoying problem irrespective of the email "client"
Spoofing the phone number is not very hard. That said, you'd still need the PIN to gain access to the email. A 4 digit pin is not the most secure thing around, but the combo of the phone number and the PIN seems reasonably safe. Thoughts?
The reason I went with a phone number is that phone calls generally play well with cars (in-car bluetooth headsets, etc...) whereas audio for apps usually has a harder time connecting to in-car devices.
I wanted to elaborate on Matt & Rama's points and go a bit further:
GeoAPI
+ Got us an API key within 5 minutes of requesting it
+ Comes with a comprehensive list of points of interest, from place data (restaurants, bars, ...) to other (parks, cities, etc...) for the US. This was the single most important factor as it enabled us to build a place-aware application without worrying about places too much
+ Has an API that scales and easily handled our bump in traffic due to being TechCrunched
+ Has extremely supportive and fast technical support and issue resolution. The engineers, despite being at Twitter, still react in "startup-time" which is critical to our success
SimpleGeo
- Took 2 months to get us an API key
- Still has no POI data. This is apparently coming in their marketplace but will cost an extra fee and there's no way to test the quality of the data to-date
Basically, it was no contest. I have no doubts that the SimpleGeo guys have built a great way to index & search for data spacially, but without a comprehensive POI database, the effort required to build a geo app is much greater. With GeoAPI, we not only got fast geospatial search but also a well organized list of POI to go with it.
2. If the company is still private, the stock's value is determined by the last 409(A) valuation for Common stock that the company performed, assuming that your options are for Common stock (which is very likely). The company must perform one of these valuations a year and should provide you with that amount upon your request.
3. Exercising the stock starts the clock for long term capital gains treatement. That is, if you sell the stock a year after exercising it, you will pay capital gains tax on the value difference between the sell price and the value at exercise.
Math wise:
* TP = strike price (the price in your option contract at which you buy the shares)
* EV = value of a share at exercise time, as determined by the latest 409A valuation
* SP = sale price of a share when you sell the stock eventually
* #S = the number of shares you have
* IT% = Your income tax rate
* CT% = Your long term capital gains rate
At exercise:
- You pay to exercise the shares: #S * TP
- You owe in taxes: #S * (EV - TP) * IT%
At sale
- You make: #S * (SP - TP)
- You owe in taxes, assuming you waited a year to sell: #S * (SP - EV) * CT%