[bogomipz]

Why not? I feel like this is a dirty secret and double standard at high profile tech startups - management and those with preferred stock regularly sell to the secondary market while the common workers are supposed to be wait for some distant pay day that may or may not arrive. Why shouldn't you be able to take money off the table? If the company is really that solid and the IPO is such a "sure" thing as you are lead to believe then it shouldn't matter. What I learned when I sold my options was that I was not the first and in fact the secondary market companies told they sold employee options before so it can and is being done. I don't think its a red flag at all. It means your savvy. I think that most employees aren't aware that this is even an option for them.

[p4wnc6]

Most people probably agree with you, but it doesn't mean founders or start-up execs will see it that way. And there's no way to know why they might cause a problem over it. It could be that they've seen a lot of people selling and view it as a bad signal and they just take it out on you ... or it could be that they are just psycho and see their company like a cult and suddenly you're "not a team player" if you want to sell shares.

People are far from rational about this stuff.

[bogomipz]

I get what you are saying but remember founders and execs need quality people to build and maintain a successful company. Its unlikely that you will be fired for this. I think if you went and told everyone within earshot that you did this it might problematic but if you kept it to yourself and did it discretely I think its unlikely to cause problems. Also like I mentioned ask these companies(and theres on a couple) if they sold options for your company before.

As far as psychos and/or the cult mentality, my view is that I wouldn't want to work there anyway but thats me.

[Silhouette]

If you have management that think like that, you might well be better off taking the money and looking elsewhere anyway.