Earlier quoted context omitted.
Why is it a requirement to have "skin in the game"? What does that even mean? 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.
The risk of joining a venture backed startup is that no new money comes in and there is no exit and you are out of business in a matter of weeks, like what happened here. 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…
The only people who insist this must be true are founders that want to unload as much of the risk on their investors and employees as possible so that they themselves carry little to "skin in the game"