[mblevin]

In my experience it's neither greed nor obfuscation, but rather along the spectrum of ignorance, cash conservation paranoia, and and/or a misplaced sense of justice.

Ignorance in the case of not knowing it can be done - many "startup" lawyers are operating with a playbook written in 1996.

Cash conservation in the sense of "holy schmoly I'd have to pay $X,XXX upfront in taxes to cover their option purchases???"

And "justice" in the sense of "well I'm taking a personal risk as a founder, so if you're not all in with me then suck it and your options will just go back in the pool when you quit."