Your answer here is completely unclear to me. I understand you don't want to give out legal/money advice, but can you at least explain the capital gains thing you were talking about.
I am neither a lawyer nor an accountant, so I don't know what the tax/legal issues are with cashing out and/or capital gains, nor it's "clock". But I do have stock options that are vesting and I do have to decide if I want to exercise them early, or not. When this issue first came up, no one knew or seemed to think there was any difference between exercising the options and not exercising the options. I did it because everyone else did it. Probably a bad idea, huh?
Here's the deal: you want the gain in stock value to be taxed as "long term capital gains", which is a much lower tax rate (~15%) than as income tax (~30%).
To do this, you need to sell the stock that you purchased with the options at least 2 years after you received the options and at least one year after you exercised the option.
What many people do is purchase options to 'start the clock' on that one year window.
A much more complex way of doing this, which I've been on the receiving end of, is to grant your employees their options immediately upon them joining and have an agreement where the company can repurchase them (at no cost to the company). The amount that the company can repurchase is reduced each month.
Your answer here is completely unclear to me. I understand you don't want to give out legal/money advice, but can you at least explain the capital gains thing you were talking about.
I am neither a lawyer nor an accountant, so I don't know what the tax/legal issues are with cashing out and/or capital gains, nor it's "clock". But I do have stock options that are vesting and I do have to decide if I want to exercise them early, or not. When this issue first came up, no one knew or seemed to think there was any difference between exercising the options and not exercising the options. I did it because everyone else did it. Probably a bad idea, huh?