I don't expect this would be a company, but rather more of an open source project. I have been thinking about this for a while, so I'll throw it up to see if there is any interest. I would really like someone to create a website full of information and resources for first time startup employees regarding stock options.

It would be great if there was a calculator which would allow you to experiment with different liquidity outcomes given your existing/proposed stock options.

For example, you would be asked to enter the total number of outstanding shares, the number of shares you have now, the number of shares you are entitled to, your vesting schedule, if you have any acceleration upon change of control or other scenarios and if so how much, whether you have preferred vs common shares, liquidation preferences (if any), etc.

Once you enter all of the information that you have, the calculator can estimate how much you stand to make in certain scenarios. You could answer "How much does the company need to be bought for in order for my options to be worth $X?" or "If the company sold for $Y amount, how much would my options be worth?".

If certain pieces of information were not entered into the calculator, then it could show error messages and link to additional resources explaining why that particular number is so important.

I realize that the calculator would likely not be exact because of missing information and the complexities of each particular company's structure. However, I think in many cases it could be surprisingly accurate. The most important thing is that it be used as a tool to introduce important concepts and terms which new startup employees should research and understand.