[BaseballPhysics]

No disrespect intended, but with respect to this charge of "hypocrisy": you knew what you were doing when you exercised those options.

You had vested options in a privately held company. I assume you chose to leave, forcing you to exercise those options or give them up. When exercising those options you had to know full well you were taking a gamble that you wouldn't be able to exit from your position. That's a choice you made.

So no, there's nothing unfair or hypocritical about this in the slightest. That's the risk of choosing to buy stock in a private entity, and it's a risk you take when joining a startup: the possibility that you might not get an exit, or the timing might be wrong for you personally.

[edmundsauto]

That line of thought also means the employee should take every legal avenue to execute the letter of the contract. It might be legal but it’s a difficult situation - nobody wants to feel like they are in a contentious relationship with their employer.

[BaseballPhysics]

> That line of thought also means the employee should take every legal avenue to execute the letter of the contract.

Yes. They should.

Exercising a large number of options is rarely a cheap financial decision. It is absolutely necessary to go into it clear-eyed with a complete understanding of what you're getting into because in doing so you are locking up potentially significant capital.

And this isn't some weird edge case situation. This is something anyone exercising options in a private company needs to deal with.

[dragonwriter]

> nobody wants to feel like they are in a contentious relationship with their employer.

Being in a contentious relation with your employer is the normal state under capitalism (and it being an ex-employer doesn’t necessarily cure that); no one wants to feel mortal, either, but not wanting to feel something doesn’t make it less true.

[stock-throwaway]

I think you're assuming that all of this legalese is well-understood beforehand. I was pretty young and new to the startup scene when I joined this company. I didn't know what a 83b election is or a 409a valuation, let alone the terms of limited transferability.

By the time the company was a success, I could either leave the stock on the table or purchase it since it's worth a lot more money than I'm paying for it.

I agree that I'm on the shitty-end of this contract. Chris Voss says people only appeal to fairness when they've got nothing else. lol. And I'm there. I signed up for this and I wasn't knowledgable enough to negotiate my options agreement contract when I joined.

But the fact is, lots of people are probably in this same position. I'm told lots of people execute forward sales and companies don't care because they don't have to report it to the SEC and get another 409a. CEOs also like having a grip on their employees, holding a carrot in front of them to keep performing.

I suspect that at some point, there will be an interesting legal case here. Suppose I were to file for bankruptcy - what happens to these shares? How can I be bankrupt if I still own millions of dollars in company shares?

I'm not expert here, but I'm really curious what this landscape looks like.

[BaseballPhysics]

Honestly, I do feel for you, if only because I was fortunate enough, when I was young and in a similar position, to have a mentor I could talk to who took me through some of the important concepts. As a result, I understood the gamble I was taking and could make the decision with reasonably complete information.

One thing I will say: if you get the chance, be that mentor to someone else in the future. You may be stuck learning an expensive lesson, but hopefully you can prevent someone else from doing the same some day.

[stock-throwaway]

A different topic entirely but: how did you find a mentor / someone to mentor? That relationship has always been curious and elusive to me

[BaseballPhysics]

Alas, I wish I had good advice here, but honestly, I just got extremely lucky.

When I first got hired (at a very small startup) the hiring manager was an utterly brilliant former Bell Labs guy who'd made his way through a couple of prior startups, and he served as a mentor of mine for many many years after.