Has any HNer participated in such a secondary sale? I think it could be informative to describe the experience, whom you dealt with, how a price was agreed upon, how your company discussed secondary sales, etc.
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 a legitimate seller. SharesPost representative got in touch with my employer. My employer had the right to first refusal which they waived. The process took few weeks with escrow etc, but was smooth.
SharesPost charged me a %ge fee. I also had to pay for the escrow service.
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.
When secondary brokers have more buyers than sellers of a particular private stock, they come looking for you - and that's the time when you want to do your selling, not when people are freaking out and you're competing with others actively looking to unload their holdings.
Just to spell it out - that's the perfectly clear indication, not 'oh hi I have 125,000 shares of X to sell'.