I think this story is about not giving up on hard/impossible tasks. Most people would not have even tried to attempt to contact Michael Jackson because to them it would be an "impossible" task. Just like most people will tell you why a new business or product idea should not be made.
Agreed, he has already achieved financial freedom so it is a lot easier to experiment with throw away companies and projects. Others have to find that balance between working on fun activities and those that earn you income.