>Most assholes don't have that level of reflection so I'm not going to be too harsh
I think that's what differentiates your run-of-the-mill asshole from a sociopath.
While the author doesn't do a great job at eliciting sympathy (if that was even his goal?), I can imagine the weeks/months/years after an exit can be tough on someone who has invested so much of their personal worth in a single entity. I think certain personality traits thrive in the start-up founder world, but the things that make those people succeed also leave them susceptible to massive emotional lows once the story is over and the dream is realized.
I think that's what differentiates your run-of-the-mill asshole from a sociopath.
While the author doesn't do a great job at eliciting sympathy (if that was even his goal?), I can imagine the weeks/months/years after an exit can be tough on someone who has invested so much of their personal worth in a single entity. I think certain personality traits thrive in the start-up founder world, but the things that make those people succeed also leave them susceptible to massive emotional lows once the story is over and the dream is realized.