Common mistakes and misconceptions about stock options.
Adam Rifkin stashed this in 106 Miles
If you're new to the world of stock options, it helps to ask questions.
David Weekly's article points to his excellent Introduction to Stock Options for the Tech Entrepreneur or Startup Employee.
There are at least two good reasons not to "forward-exercise 100 percent of your options the week you join a startup and file an 83(b) election immediately" as recommended by David Weekly's article: first, there's no guarantee that the options will be worth anything, so waiting gives you better information about whether exercising the options will be worth your while; second, most startups do not allow employees to forward-exercise options because of the administrative hassle associated with doing so.
Along those lines read A Newbie's Guide to Startup Compensation.
In any case, David's article is well-written and has a lot of useful information in it, and at 106 Miles we highly encourage people to learn as much as they can so we can make better informed decisions.
We've recently heard about how Skype rendered some employee stock options worthless.
Behind the real story lies an important lesson about the dramatic ways compensation is changing in the Valley. Employees should never assume each employment contract is the same as the one they had before. That’s especially true now, as companies take longer to go public and new forms of liquidity like secondary markets emerge, compensation models are changing dramatically in the Valley. The importance of actually reading whatever it is you are signing is paramount.
So that's a common theme: Actually read what you are signing.