The worst thing that can happen at an early company is that it sort of works.

I like the deal where I roll the dice and don't have to work again if I win. I'm fine with the deal where I take a barely-passable salary and do something wacky for a year.

The worst deal I can imagine is that the startup slowly grinds its way to profitability over 3 years, can't raise, and grows 15% / year.

Every company I've seen do that never fixes the salary issue. Everybody's still making their seed-stage base, or maybe +25%, which is still a 30% pay cut from the last job they had. Their equity is worth nothing. There's no career advancement, because there's 2 staff jobs and 3 EM jobs and 1 VP job.

There's lots of ink spilled about how founders expect early employees to work hard, perhaps too hard for what they're paid. It goes the other direction, too: early employees should expect founders to succeed, because there's always another startup to join.