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When to sell?

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  • Marko-ER
    replied
    Syndicated real estate in an opportunity zone (OZ) fund?

    Leave a comment:


  • Ozarka
    replied
    Short and most likely unhelpful answer = it depends. Do you need the cash? Would you be upset if SQ had a 50% drawdown?

    It depends on your risk tolerance and situation. I have SQ from the $60s and have sold some on the way up. Sure I missed more upside by not holding my full position but I've realized some gains and it allows me to sleep better at night...and that fits my desired risk profile. I still have some left over and will continue to ride it out but, for me personally, it feels pretty good to lock some in along the way.

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  • fatlittlepig
    replied
    answer depends on how much you have, there's a difference if it's 20K (let it ride), or 2 million (take some off table)

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  • Tangler
    replied
    When to sell? Immediately.

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  • Tangler
    replied
    Sell.

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  • Panscan
    replied
    Isn't the whole point of buying it to make money, sell it at some point and then pay taxes on it? A good strategy to lock in your gains? Sell it. Would you rather it tanked in value and you didn't have to pay any taxes? Or sell enough to cover your cost basis + taxes on the gain and let it roll

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  • jfoxcpacfp
    replied
    Originally posted by molar roller View Post
    I don't think appreciation alone is a reason to sell, or avoiding LTCG tax is a reason to keep it.
    If it's risen to the point where it makes your portfolio too risky, sell it. If it's a part of a well balanced portfolio, keep it. But its current price should have no bearing on your decision*.

    *Coming from a guy who never sells anything, so keep that in mind.
    Couldn’t agree more. And don’t contribute it to a DAF unless charity is one of your GOALS and the donation fits within the parameters you have already set (which includes good tax planning).

    Never give away assets, choose to earn less, or spend money just to save taxes.

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  • molar roller
    replied
    I don't think appreciation alone is a reason to sell, or avoiding LTCG tax is a reason to keep it.
    If it's risen to the point where it makes your portfolio too risky, sell it. If it's a part of a well balanced portfolio, keep it. But its current price should have no bearing on your decision*.

    *Coming from a guy who never sells anything, so keep that in mind.

    Leave a comment:


  • jfoxcpacfp
    replied
    Originally posted by CordMcNally View Post
    but if I were really, really old (like over 40 old)
    WTH?!?
    I would call you a whippersnapper but that would only cement my oldness.

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  • CordMcNally
    replied
    In my current position I would donate it but if I were really, really old (like over 40 old), I'd probably just hang on to it since I'd be living on borrowed time anyway.

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  • Hatton
    replied
    Try to balance the sale with a tax loss harvest if one occurs. Also a DAF contribution. Otherwise sell part of it and pay the gain.

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  • Random1
    replied
    Selling and paying taxes is always preferable to riding back down and not paying taxes.
    P/E ratio 591.88
    It can always keep going up , but it has a lot of downside risk.

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  • ENT Doc
    replied
    Options:
    1. Die
    2. Lie
    3. Donate
    4. Quit working, sell, and have 0% cap gains rate

    Or:
    1. Sell and diversify immediately
    2. Sell LT lots, turn off div reinvesting (if applicable), sell more LT lots as they reach the 1 year mark

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  • Peds
    replied
    donate it

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  • DCAflyer
    started a topic When to sell?

    When to sell?

    I have a taxable brokerage account and I bought SQ about 4 years ago and it has absolutely taken off over the past two years to the point I have no idea of its true value. What is a good strategy to lock-in gains, but also not wanting to liquidate the entire stock due to the large capital gains tax hit?
    Last edited by DCAflyer; 02-16-2021, 09:03 AM.
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