Thread: Side Hustle
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Old 12-30-2020 | 09:31 AM
  #545  
Seneca Pilot
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Originally Posted by Gunfighter
-How much are you leveraging your $20,000?
-How do much time does it take reporting 1,700 trades on your tax return?

$75 per week comes out to $3,900 per year, which is a respectable 19.5%. A few days of being the windshield vs the bug can take that down to the mid teens very quickly. An 80% success rate at the often touted 2% monthly returns is 19.2%. You seem to be in the ballpark with the research I've done. I'm still uncertain about the time commitment, bookkeeping requirements and the tax liability of trading outside of a retirement account.




In the past, I've just rolled the covered calls out to the next expiration cycle. You could also buy back the shares after exercise, which creates a CG problem in a taxable account. An exercised ITM option isn't the end of the world. I recently sold FEB 725 CC on a portion of my TSLA position. I'm planning on rolling out to March in about a month.

Thanks for all the TW pointers. There are lots of similarities between thinkorswim and tastyworks. I just figured out that Tom Sosnoff is the connection between the two.

Futures and options are 1256 contracts. There is no single trade reporting like there is with individual stocks. You just get a 1099. 60% long term capital gains rate, 40% regular income rate. Get your tax advice from an expert but that is the treatment for options and futures.
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