I had a horrible horrible, nightmare boss a long time ago. 22 year old CEO in Silicon Valley. After working a 10 hour day, I would go home, he would call me and would have me listen to his recorded phone calls with ultra wealthy clients and then have me transcribe them by hand. Pretty sure that was illegal, but my main beef was that I was a fundraiser and this was not at all my job description, and I couldn't handle staying up till 2 in the morning every night. Plus I knew it was wasted work because he never once checked the transcripts. Together he and I raised about a quarter million in capital in a very short period of time, which also irritated me because I knew it was a dysfunctional company on the inside. He thought it was funny to embarrass me. So he'd do things like tell me to sing in front of the office or I'd be fired.

One week, we had a business trip Texas, where I'm from. I introduced him to some people I knew, and afterwards he snickered about how he was going to get bags of money out of them. I was super pissed because these were my friends, and because I'd hated this douche CEO already. We got into a heated argument at lunch, which extended into a heated argument at the hotel, which extended to a heated argument on the drive to the airport. And when we got to the airport, I just told him I'm not going back to California with him. I just drove to the gate instead of the rental car place and told him I'd take care of the car but I'm not going back.

I had a several hour long conversation with the COO, while the CEO was on the plane, and I found out a few days later that the COO himself had quit!