Makes sense.
However, there are also people that have been trying to make it in their field for several years. They've exhausted every possible option, but they also can't walk away.
Though, reading your post again, I guess the key words here are "intelligently" and "early".
The key thing is having a plan in mind. Broadcasting has more protection than say doing Art does because the work product being put out is directly tied to you (ie: vocals, face, etc).
I think a key thing is if you were doing artwork, music, etc for some form of startup (but had faith in the idea), you'd want to secure some portion of ownership in lieu of payment if there weren't funds available. It's not so much working for free as much as making sure that if things do well that you have an asset you can fall back on so that your work wasn't for nothing.