I was working for a guy who co-founded a certain frozen desert business sometime back and he was always an "ideas" guy. Anyways he really liked how I managed and my personality and stuff and asked me to be his top operator for his new venture he was pitching to his dozen or so VC friends/associates. So I'd have to go in the city constantly to accompany him when we'd pitch the business. Eventually I told him I've spent at least $150 on traveling and ofc a lot of time and it was starting to actually be rather detrimental since no one was biting and I actually couldn't keep spending half a day in the city not working or being paid. He just could not understand how this was an issue because he had so much passive income. He also commented that I only had like two (deeply discounted) suits and maybe 4 dress shirts. He didn't like I was always wearing a variation of the same stuff. Just straight up didn't realize him paying me the $11hr (a bit above min wage at the time) while I kept having to not work and no compensation while doing all that was legit no longer possible for me. So he "found someone who is more comitted."

There is more to it all but he legit pleaded with me when I found a better job with more hours and actual benefits. So I made a simple demand of matching the same pay because that job I was doing was solid and close to where I lived. He couldn't even give me a dollar more and hour and didn't understand paying $400/mo through his healthcare plan would in fact be much worse for me. Just completely clueless or just stupidly greedy