Last year I left a company after ~26 months and some great work due in large part to the below-market-pay and shitty options situation. Founders were super secretive about how stock and options had been handed out, and even worse, very opaque about things like "how much money do we have left"?

If asked to bump salary (paying their technical lead, me, $60K sans benefits), they'd say "we have no money to do so". If asked to provide more equity (because that's how companies have traditionally handled having little cash-on-hand), they'd say "we can't issue more options".

That continued inflexibility, plus other things, meant it was time to leave.