Often the dice are loaded, you can find many stories on here on about some financial trickery whereby the options become low value or worthless as the founders and VC's cash out. I personally evaluate them at $0 because of this. It's a shame too because that sounds like my ideal work setup.

Pretty sure this article was posted on HN, which is why I remembered it: https://marker.medium.com/my-company-sold-for-100-million-an...