Analogous to someone using the company car to make some extra money as a uber/lift driver. Do you still not see the problem?

For most of us yes. The decent amount of money that allows us to live comfortably gets real limited when we stretch out further with stuff like a boat and a horse. But for those that got lucky in life to comfortably afford it, a boat and a horse arent seen the money drains since they have more to give. This lets them enjoy the activities that comes with a boat and horse more.