Quora was definitely not the first startup to do 10 year exercise period, not by some margin. My Lime Wire stock options from 2000 had a 10 year exercise with a 6 year vesting schedule, no cliff and vesting every 3 months. Here's the proof: http://imgur.com/6eTUyui
Adam's on the right track though. I just had to write a 6 figure check today to exercise my vested options at my current employer because of the 90 day clause. It makes me angry because the company's official stance is that the board wants to use stock options as an employee retention tool. I was fortunate enough to have had the cash but a lot of other people are not and there is no secondary market. So if you get fired or have to quit during a bad market you are basically screwed.
Adam's on the right track though. I just had to write a 6 figure check today to exercise my vested options at my current employer because of the 90 day clause. It makes me angry because the company's official stance is that the board wants to use stock options as an employee retention tool. I was fortunate enough to have had the cash but a lot of other people are not and there is no secondary market. So if you get fired or have to quit during a bad market you are basically screwed.