as a holder of some employee stock now actually worth six figures (bc company raised a round and is offering to buy back my shares) I have been confronted w the opposite question: do I want to sell it? I did not. reason being that I didn't need it right this second and it wasn't a life changing amount yet and it could be. I think the illiquidity helps in that I'm not tempted to reevaluate this decision every trading day and likely make a bad decision at the first negative data point.
at some point a company is clearly on the "will probably exit for non zero amount" track and the standard "its probably worth 0" advice does not apply. I'm not sure HN agrees with this.
I was recently in the same or similar position (partial buy-back) and opted to sell.
Tax concerns aside, your essentially betting that the stock will do better than an alternative investment. That might be the case, but taking the money and then reinvesting it is also a valid “I don’t need this money right now” option.
There’s also the factor that you’re more “eggs in one basket” if you keep the stock.
I personally pulled mine out to donate it, as it is potentially life-changing money in other people’s hands.
yes, i do think this stock has potential to at least 2-4x in 2 years from where it is today, and if things go south will at least be acquired for current valuation. so its probably better than any alternative investment i can do.
at some point a company is clearly on the "will probably exit for non zero amount" track and the standard "its probably worth 0" advice does not apply. I'm not sure HN agrees with this.