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Re:I took the $300K by defen on Sunday May 26, 2013 @03:59PM (#5772228)
According to linkedin, he worked at powerset for 3 years at "well below market rate". He got 240K in bonus money from the acquisition. So the question is, how far below market rate? If he was making 60-80K as you suggest, that's about 60-80K below market rate. Which would mean that he took a huge risk for very little actual gain, especially since the bonus was probably taxed as regular income rather than capital gains.
Re:I took the $300K by kevinpet on Sunday May 26, 2013 @10:52PM (#5773221)
Part of that was sunk costs. Presumably he was gambling on Powerset being a much higher exit. This store and the "I left $300k for github" are two sides to the question of what do you do when you are facing a soft landing rather than launching into orbit.

If the bonus had come in the form of a more lucrative cash buyout, it likely would have ended up being short term capital gains as options were cashed out, so there isn't even a tax difference.