But then this analogy doesn’t hold… Has there ever been a startup in history where it’s break even everywhere? Investors don’t get their money back, customers (hopefully!) are made whole, and the founders and employees are now out of a job and _perhaps_ didn’t get their final pay check depending on how bad it is.
Yeah, you're missing my point. Given most startups fail, the question isn't "at the end of the day do you still get a paycheck for your failed startup", it's "how much of your life did you burn on that failed startup".
Since we're talking about a specific startup whose founders are participants here, I think we can do without the ghoulish stuff about them not making payroll or whatever; "winding down" implies they're failing in an orderly way.
I have no clue what you’re trying to convey with this analogy? “Free Parking” is different in virtually every household.