Message Font: Serif | Sans-Serif
No. of Recommendations: 0
I exercised and held a good deal of my former company's ISO's, and the stock's gone up quite a bit. I haven't yet fulfilled the 1-year holding requirement, and my income for this year is abnormally high due to ISO's I exercised and sold cashlessly, so I'd like to avoid selling them if I could.

I heard about shorting stocks, and wondered if that's a viable option. What are the tax implications for shorting a stock?

If I short it, and it continues to go up, can I use some of the exercised ISO's to cover the short? (I imagine I can ask my broker, but figured I'd ask here too, while I'm at it) If so, what are the tax implications of that?

Mucho thanks!
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.
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.