Earlier quoted context omitted.
I have participated as a seller. I offered some of my exercised options for sale on SharesPost [1]. The SharesPost representative contacted me; she said that she had a potential buyer interested, but the bid was slightly lower than my initial ask and the volume they wanted to buy was a little lower than what I had offered to sell initially. We agreed on the deal. I filled out some paperwork and sent proof that I was…
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?
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.