[throw2192015]

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 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.

[1]: http://sharespost.com/

[shostack]

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?

[throw2192015]

> 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.

[kbenson]

Offtopic: Assuming your account is a throwaway you just created so as not to reveal your selling history, and you based the name on some variation of "throwaway", the month, the date and the year.... then you used the wrong year. ;)

[dpflan]

Thanks for sharing this. The process does sound straight forward. It seems that you still retained some shares. Did you exercise with the intention of selling a portion on the secondary market?

[throw2192015]

I used some of my savings and a cash bonus I got at work to exercise some of my options. I held on to that stock for a year. The next year I sold a portion of that stock in the transaction described above. I used the proceeds from the sale to replenish my savings, which had taken a small hit due to the AMT from the previous tax year.