Startups are risky and even though you work at one, I don't think they're for you. There's plenty of other union labor jobs with pensions out there that seem to be more your speed. Your position isn't a reasonable one.
You want to have your cake and eat it to. All the rewards of being an early stage startup employee without any of the risk or skin in the game.
The risk to an employee at a company that got $250 million should only be accepting options that could be worthless in lieu of a portion of salary. There absolutely does not need to be any risk of losing healthcare, lacking severance, or any other loss of benefits. Founders want you to believe this but it doesn't have to be true.
This is constantly looming over your head and used to be something understood by startup employees before the era of zero interest free money and "startups are kewl".
Any money raised got spent, otherwise they didn't need to raise it.
The trade off to take on the risk of being underpaid and possibly soon-to-be-unemployed by a startup are the potential equity payoff, the work environment and the human-networking. And it's usually worth it because you're buoyed by the local startup community and the high chance you get another job with people you know tomorrow if things don't work out.
The problem here is that our industry is flooded with the types of people who would otherwise have become lawyers or finance people because they chase comfort and status as opposed to a desire to work on cool shit with cool people. It kind of makes me hope these conditions extend for a while to weed out the people who don't belong and we can get things back to relatively-normal.
"why it is a requirement" has nothing to do with the law, the whims of "the founders", etc.
why it is a requirement is an economic truth - if there are enough players that believe that a gamble on working for an early stage startup is worth taking on some substantial, but perhaps not ruinous, risk, then that sets the bar.
> Founders want you to believe this but it doesn't have to be true.
Whether that is true, or "has to be true" depends only on the market. It certainly seems that it was true very true and probably still is. But neither you, the law, nor the founders have any control over whether it is worth it at the moment in your situation.
Fortunately, there are many startups whose leadership is prosocial enough to try to offset some of the risk to its employees.
Since you seem like a Chicago School kinda guy, I'll put it in terms I think you can understand: employment is a market, and I am fortunate enough to have a optionality. It's bizarre that you fail to recognize that; it's pretty critical to your own analysis.
They're shitty coworkers too.
