The bulk of my litigation work over the years has come from partnership disputes, often where one partner believes they should have received more equity than they actually did or that the company shouldn't have sold so soon, etc.

It long ago ceased surprising me when I'd see that the very first employees in a company would have 10%+ of the company, had left some years before, and likely wouldn't see much or anything out of the company after the dispute was resolved.

If OP is effectively taking a 15-30% paycut to continue to double down on equity, it could really pay off big time or it could be a terrible misfire. If it were me, I'd try to ensure that my eggs weren't all dependent on my employer.