Our company has these employee stock purchase offers every so often. This is when investors will purchase employee stock. Since we're a private company (not traded on a stock exchange), this is basically the only way employees can cash in their stock options and restricted stock units. Since my experience with stock at the previous company wasn't that great (stock went from $142/share to $275 to $9), I have been selling some shares during each purchase offer. It locks in any gains you have accrued on your stock holdings but if the price continues to increase, you lose out on potential gain. It's a game to see how much risk you can tolerate.
Anyway, we had a purchase offer in March of this year for $220/share. Thinking that's pretty good, I sold off a bunch of shares. Well, four months later, we managed to negotiate another offer, but now at $270/share. I just "lost" $50/share. At the time, I didn't think we would get that much more in four months. In hindsight, I should have held off but there's always risk that the stock price may go down. Oh well. I'm still glad that I was able to make some money off the stock.
I did lose out on the equivalent of a very nice new car though. :(
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