Following second-generation wealthy employers tends to breed complacency, while working for first-generation entrepreneurs often feels harsh and demanding.

This really comes down to experience. When someone has lived in comfort for too long, they treat it as the baseline. When someone has lived in harsh conditions for too long, they treat cruelty as the baseline. The former thinks it's fine to let you take time off—it's only right. The latter thinks it's fine to make you work overtime—it's only right.

Whether he treats you well or abuses you, you're still a puppet.