Earlier quoted context omitted.
I think its the power dynamic. Not everyone can just leave jobs. If people don't trust their CTOs, bosses, CEOs, that is mostly the bosses fault and on them to fix. Requiring the person who can be at-will fired to also manage upwards is pretty much a fail state.
Not managing upwards is how you wind up in a fail state. Business, teamwork and employment isn't a zero sum game. Everyone is working together to achieve something. Helping your boss understand why something shouldn't be done/prioritized/cancelled is paramount to being efficient. If you think you can never tell your boss no because you'll be fired, you're not going to have a good employment story.
If you give it away for free, theyre not going to voluntarily pay you.