Some people are stupid :-) He would have learned much working for you for four hours, and he would have a rare collectible jersey!

But I disagree with this "I find such people manipulative. They have money, so they try to twist the rest of the world to play by their rules."

Sometimes it is as you say, a sense of entitlement, however sometimes it was an opportunity they didn't have.

Let me share two anecdotes to illustrate, first we have old VAX parts. You know that architecture that Digital Equipment made around the turn of the century. During the big Y2K scare a lot of perfectly good VAX computers were dumped for scrap, I bought too many of those. But in putting together working examples for my collection I would have extra parts. Sometimes I'd sell those parts. I asked a guy who was buying a part from me for more money than I had paid for the entire system why he didn't do what I do and just pick up scrapped machines? His response was surprising. He related that he spent his time shipping stuff around the country, he made good money doing it. He used VAXes running his custom software to make that work. He spent his time doing what he was good at, and then using the extra money he made to occasionally go out and buy a VAX part. The money was fungible he could translate it into VAX hardware easily. If he subtracted off the money he would lose by spending his time buying up old machines and testing them instead of shipping stuff, and added back the money he saved by getting parts this way, he still came out behind just shipping stuff . So while I might think he was 'paying a lot' for a part, he was, in fact, saving money!

A more personal story, early in my marriage my wife and I would occasionally get into arguments about chores. (I'm sure this was unique to my marriage :-)) She wanted me to do a variety of chores, and I wanted to hire someone to do those same chores. My reasoning was that at the time I had a number of people who were willing to pay me $75/hr for consulting on various technical projects. This was work that I enjoyed doing. Further there were lots of people who would do any number of household type chores for $10 an hour. So I could spend the weekend doing a consulting project, make $750, and then hire someone to come out three times a week, four hours a day, and do chores for the whole month!

In neither case, my VAX parts buyer, or myself, was trying to 'twist the world to play by their rules' rather, there are rule equivalences that are arbitrated by their monetary value. My 10 hrs of consulting was 'equal' to a month of housework, but it is absolutely true that I wasn't following the 'rule' of 'husband does housework too.' [1]

The life lesson I took away is that, like the concept of 'enterprise' value, strict monetary exchanges don't include the emotional cost as well. The emotional cost can and does change the sales price significantly at times. It can be useful to know when someone is so emotionally invested that the total cost is outside the market. As with raganwald's shirt, the replicas can be bought elsewhere for much less than the total cost. When the startup founder's emotional investment prices the startup outside of market norms it can be leading indicator of trouble.

[1] For future and current husbands out there I do not recommend you try reasoning to this by explaining you could spend your time building a robot and then it would do the housework. Rather than impress your spouse with your robotic skillz they get rather insulted that you think their work can be replaced by a robot!