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.
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.
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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.
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.