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To emphasis the risk aspect.

I worked at Yahoo for 3 years. I joined at a very fortunate time, and left at a very fortunate time that let me basically double my options. It wasn't a fortune, but it was a nice extra chunk.

But when I left, one of the guys reporting to me was still under water on the far larger chunk of options he had been granted prior to the dot-com bubble bursting. As far as I know they wouldn't have gotten over water at any point before they expired.

At the time I joined, Yahoo seemed like it was on a solid upwards trajectory. By the time I left you might have started seeing signs but things were still going the right way for a while, and had I not been offered a very interesting job I'd likely have stayed and lost a significant proportion of the value of my options.



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