Investment & Investing

Some other things to consider:

• Are they public? In other words, if you wanted to exercise the options and sell some shares are you able to do so (within the enforced trading windows that may also apply)? Companies that haven't IPO'd may only offer occasional internal options sales at periodic times and with other restrictions that mean you can't pick and choose when to do so.
  
• Tax is tricky. If you have an option at price A given to you when the company had a fair market value (FMV) of B per share, then you exercise at C and a bit later sell for D. There are different areas of tax (Capital Gains, Income Tax) that apply on the differences between B and C, and C and D. The capital gains aspect is also time limited.
  
• Because of the above it is sometimes advantageous (also depends on the types of options) to exercise the options early and then hold on to the shares to dispose of at a later date. However, this requires planning, funds to exercise the options and then luck that the shares don't fall between exercise and sale, and a bit of bottle.
  
• NI is also tricky. Even more considerations here. I remember quoting "Mansworth vs Jelley" at HMRC for share options at previous employer...
  
• 99% of the time share options are a case of making sure you've got a W8-BEN on file with whichever company (eTrade, Morgan Stanley, Carta, etc) is holding the options (so they don't withhold US tax upon exercise/sale), and then exercising and selling in one go (so you don't have to front the funds to exercise) and then deal with any residual tax nonsense yourself rather than splashing the moneygun.gif and then finding you have a large tax bill you don't have the funds for.
  
• Pay attention to vesting schedules and options expiries, especially if the company isn't public.