And I continually hurt those around me — just by being myself-and it’s beyond heartbreaking. Somewhere along the way, money truly changed me for the worst.
Most assholes don't have that level of reflection so I'm not going to be too harsh
Don't be so sure about that. I'm most certainly an asshole and I am extremely self aware. These two things are not mutually exclusive. Many of my closest friends are also assholes and they damn sure know it. Quite frankly that is in part why we are friends.
I agree the author is reflecting however most of his reflection is denial. If he wants to get anywhere then he needs to accept that he is an asshole. Only then can he either decide he wants to change or decide that he is ok with it.
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.