Message Font: Serif | Sans-Serif
No. of Recommendations: 0
In your case, again assuming I've read your notes accurately, you sold before holding for a year and a day, meaning you are paying regular income taxes on that set of ISOs, rather than the long term capital gains rate. While your objective of diversification is a valid one, your method of getting there sounds (if I've read you accurately) unBuffetlike (i.e., rash). This is particularly so if you are quite confident that the company is going to continue to improve its price.

Yes, you've read correctly. Well, my original plan was to hold the whole thing more than a year, treating, as you said, like the whole thing was a gift. But several friends of mine urged me to treat it like it's my money, since I do own them now. Then as the stock price has gone up much faster than I expected (it's at now where I thought it would be a year from now), pushing up its percentage of my net worth, I did get a bit nervous, which was why I wanted to see if shorting would avoid the problem.

Oh well. Anyway, thanks for the advice. I'll try to keep from doing anything rash again if the stock jumps up again.
Print the post  


In accordance with IRS Circular 230, you cannot use the contents of any post on The Motley Fool's message boards to avoid tax-related penalties under the Internal Revenue Code or applicable state or local tax law provisions.
Live Video Event Monday!
The GP team is hosting a live video event on Monday at 4 p.m. ET. Don't worry if you can't make it — we'll have a replay and a transcript. Click for more!
When Life Gives You Lemons
We all have had hardships and made poor decisions. The important thing is how we respond and grow. Read the story of a Fool who started from nothing, and looks to gain everything.
Contact Us
Contact Customer Service and other Fool departments here.
Work for Fools?
Winner of the Washingtonian great places to work, and Glassdoor #1 Company to Work For 2015! Have access to all of TMF's online and email products for FREE, and be paid for your contributions to TMF! Click the link and start your Fool career.