I'm not really sure how you know my friend, or even which friend I'm speaking about, so I don't know how you'd know her situation. She's handcuffed because she

I'm not really sure how you know my friend, or even which friend I'm speaking about, so I don't know how you'd know her situation. She's handcuffed because she's put in years of effort and hoping for a liquidity event before she leaves, lest she leave with little or nothing. She's miserable for entirely different reasons -- due to treatment she receives at work from what she tells me. Not sure why this would be surprising -- this situation is very common across startups. I am a co-founder also, and I have equity vesting agreements, understandably, as I want retention; I don't want employees constantly leaving with the next wind that blows. At the same time, I'd hate to keep a miserable employee who isn't fully productive. I'd like to think I set a good enough workplace culture that there wouldn't be harassment/bullying, but who knows... What is more wicked, and beyond me as a business owner, is US tax treatment on illiquid equity. That really needs to change.