How did things work out from a tax perspective if you don't mind my asking? Also, what sort of communication did you have with your company before/during this transaction regarding it?
Is this the kind of thing employers might freak out about if they are blindsided by the request?
> How did things work out from a tax perspective if you don't mind my asking?
The proceeds I got from the sale were treated as long-term capital gains. I got a 1099-B from SharesPost.
> Also, what sort of communication did you have with your company before/during this transaction regarding it?
I mentioned my desire to sell some of my stock to my manager. I was directed to speak to the head of legal department. Here is what I learned that person. The company could not provide me with a buyer, or advice me to sell/hold etc. But once I found a buyer, the company was bound to agree to that sale or direct me to another buyer who was offering at least the same price.
Is this the kind of thing employers might freak out about if they are blindsided by the request?