[PopAlongKid]

>given there is a market value for common stock in private companies, even early ones

I don't understand what you are talking about. I exercised stock options in a dot com startup within its first year and at no time in the ensuing eight years was there ever a market where I could sell my stock, which eventually became demonstrably worthless. As someone who knew more about it than me later explained, he didn't exercise his options because he knew there would always be millions of dollars in line ahead of him, because of the "board meetings", as stated.

And why wouldn't someone pay face value for a valid lottery ticket from a private party, if more convenient than going to an official seller?

[JumpCrisscross]

> he didn't exercise his options because he knew there would always be millions of dollars in line ahead of him, because of the "board meetings"

You’re describing standard liquidation preference. There are shenanigans Boards can get up to, but assuming you’re incorporated in Delaware, there are limits.