Stock Markets Exposed

Should I flip my ESPP stock?

I got a new job six months ago at a large company with an employee stock purchase plan. Since then, I have been setting 15% of my income aside to purchase stock. The plan has both a look-back provision and a 15% discount. The stock is currently trading about 10% higher than it was when I enrolled, so I will use the look-back provision to purchase stock at 85% of the trading price last November. Are there any clever CPAs out there who can give me advice on whether I should flip the stock or hold it until November 2008 so that it will only be subject to long-term capital gains tax? I was planning to flip the stock, but I just found out last week about the difference in taxation. Thanks for your help!

Public Comments

  1. yes, elmo! flip it like there aint no tommorrow! i'm just amazed that sessame street characters can buy stock
  2. My company offers the same thing. When I first started almost 3 yrs ago, I found out that they would do a 50% match after 18 months...great. As it turned out, not only did they match it after 18 mo's, but the stock has grown to roughly 2.5x what I paid. I took it out and put it into a Roth IRA in a good, stable fund. I still put 2% of my pay into the ESIP, but I move it over to the Roth every 6 months when it comes time to redeem.
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