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Any legal way to avoid short term capital gains?

Posted on 9/9/20 at 10:43 pm
Posted by pensacola
pensacola
Member since Sep 2005
4627 posts
Posted on 9/9/20 at 10:43 pm
I have significant tech gains from 01/20 (including ? and TSLA). If the tech sector comes back even a little I'd like to cash alot out. I already have retirement accounts and can't switch it into any of those. Is there any good strategy to avoid the extra 20% hit from realizing the short term capital gains. I expect these stocks will be down near the end of the year, especially with the uncertainty following the election which seems inevitable.
Posted by Spirit of Dunson
Member since Mar 2007
23111 posts
Posted on 9/9/20 at 10:47 pm to
quote:

I expect these stocks will be down near the end of the year
Serious question - didn't that factor into your decision to buy them?
Posted by whitefoot
Franklin, TN
Member since Aug 2006
11181 posts
Posted on 9/9/20 at 11:05 pm to
In January, he was supposed to know Tesla was going to quadruple and he'd have substantial gains he needed to protect?
Posted by go ta hell ole miss
Member since Jan 2007
13615 posts
Posted on 9/10/20 at 12:20 am to
Well, if you expect them to lose less than the 20% in excess taxes you would pay by selling you could just hold for a long term capital gain.
Posted by jangalang
Member since Dec 2014
36280 posts
Posted on 9/10/20 at 4:21 am to
quote:

Serious question - didn't that factor into your decision to buy them?
Why even go to work if you have to pay all them taxes?
Posted by Weagle25
THE Football State.
Member since Oct 2011
46182 posts
Posted on 9/10/20 at 5:22 am to
Have any other stocks with losses that you’re willing to sell?
Posted by MSTiger33
Member since Oct 2007
20361 posts
Posted on 9/10/20 at 5:51 am to
Give it all to charity
Posted by jmcwhrter
Member since Nov 2012
6553 posts
Posted on 9/10/20 at 6:27 am to
Pay them

If biden wins he'll probably raise the short term cap gain to 47%
Posted by Spirit of Dunson
Member since Mar 2007
23111 posts
Posted on 9/10/20 at 6:50 am to
quote:

In January, he was supposed to know Tesla was going to quadruple and he'd have substantial gains he needed to protect?
well, if he only thought they would increase a marginal amount, then the tax on the windfall shouldn't be a big deal. If I buy something for the long term, and it goes up a ton, I either cash out to capture the gains and see the tax as part of that calculation, or I hold for the long term.
Posted by whitefoot
Franklin, TN
Member since Aug 2006
11181 posts
Posted on 9/10/20 at 9:19 am to
quote:

If I buy something for the long term, and it goes up a ton, I either cash out to capture the gains and see the tax as part of that calculation, or I hold for the long term.


Right. And that's what he's asking about. Are there any tricks to lessen the taxes on short term gains. I'm pretty sure the answer is no, but there are people on this board way more knowledgeable in tax law than me.

I don't think in January anyone could have predicted this level of volatility and uncertainty in the market. If he should have expected volatility because it's an election year, then just look at 2016. The vix was around 12 in January of 2016, and never got above 20 except for election day, when it went up to 22. This year, the vix hasn't been below 22 since March.

You might think it was a dumb question, but you're acting like he should have planned for his stocks to increase 4x in 9 months and that there would be unprecedented market volatility.

Changing course and protecting gains after an incredible run seems prudent. Asking the Money Board for tax advice doesn't seem like something that should open a person up for ridicule.
Posted by Spirit of Dunson
Member since Mar 2007
23111 posts
Posted on 9/10/20 at 9:25 am to
Those are all fair points. And I am honestly sorry for coming off as rude, but my question was sincere... I was genuinely curious if the OP thought about short term cap gains taxes before he bought them.
Posted by Douglas Quaid
Mars
Member since Mar 2010
4097 posts
Posted on 9/10/20 at 9:29 am to
You don't actually pay the taxes until you write the check to the IRS.

If you want to avoid paying taxes you can do the following:

1. Sell your stock.
2. Convert the proceeds to another currency (a cryptocurrency would make sense in this application).
3. Renounce your US citizenship.
4. Move to a country without extradition agreement with the US.
5. Enjoy.

Note: you may want to routinely monitor the the status of extradition b/w the US and the country to which you abscond.

Posted by LSUFanHouston
NOLA
Member since Jul 2009
37031 posts
Posted on 9/10/20 at 10:27 am to
1) Wait until you hit a year, and then sell them the next day, which makes them long term gains, at a lower rate.

2) Sell losers in your portfolio (doesn't matter if they are short term or long term losses)

3) Instead of selling them, donate the shares to charity and get a charitable deduction for their fair market value.

Also, short term gains aren't taxed at 20%, they are taxed at whatever your marginal rate is. If you are subject to net investment income tax, it's an extra 3.8% tax as well.
Posted by arcalades
USA
Member since Feb 2014
19276 posts
Posted on 9/10/20 at 11:26 am to
quote:

If biden wins he'll probably raise the short term cap gain to 47%
dems do seem to think they are dictators. He probably wouldn't remember there's a congress.
Posted by KamaCausey_LSU
Member since Apr 2013
14482 posts
Posted on 9/10/20 at 11:29 am to
If you have any stocks that are down, sell them for a loss to balance.

Or on a not serious note, go to r/WSB on reddit and make some lotto options purchases. That looks to be a great way to lose gains.
This post was edited on 9/10/20 at 11:34 am
Posted by whitefoot
Franklin, TN
Member since Aug 2006
11181 posts
Posted on 9/10/20 at 11:51 am to
quote:

If you have any stocks that are down, sell them for a loss to balance.

This is what I would do. Use the opportunity to flush some losers and start new positions in stocks you might have liked long term at a lower cost basis.

Posted by pensacola
pensacola
Member since Sep 2005
4627 posts
Posted on 9/10/20 at 1:37 pm to
Thanks for the input, guys. I have already sold the losers to offset some of the short term gains. I will be paying about 20% more on short term vs long and was looking for any good ideas.
Posted by jangalang
Member since Dec 2014
36280 posts
Posted on 9/10/20 at 2:06 pm to
Just don’t sell too many losers. You can only claim up to 3000 in losses assuming you don’t rebuy the stock within the next 30 days.
Posted by pensacola
pensacola
Member since Sep 2005
4627 posts
Posted on 9/11/20 at 2:16 pm to
If one had a 10k short term loss on ABC and 10k Short term gain on XYZ wouldn’t that even out to zero gain?

I thought 3k was the annual loss carry over if ones losses exceeded gains.
Posted by Weagle25
THE Football State.
Member since Oct 2011
46182 posts
Posted on 9/11/20 at 5:44 pm to
quote:

Just don’t sell too many losers. You can only claim up to 3000 in losses assuming you don’t rebuy the stock within the next 30 days.

Carries over indefinitely so not a big deal if you go over.


And that’s an overall 3,000 loss. So if you had a 10,000 gain, you could take a 13,000 loss.
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