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> There's 0% chance someone who left early on would be able to hold on to 45%. They'd need some very heavy duty protections, and even then. The CEO, given their actions, would find a way to recover that stock later, probably at the behest of other investors.

Yeah. If nothing more subtle is possible, they can always take a round that dilutes the heck out of everyone's stake and have an agreement in place to 'make whole' some of the current team with extra stock grants or options.

I agree, there is no way to raise a new round with an ex-employee owning 45%. At best, new investors will convert the equity to a note that limits the upside in dollars.

They might negotiate something like 10-15% for just walking away though.

Yes, they should, but the issue is how they maintain that and not be diluted in a tricky/sneaky way.