Which lot to sell

Oracle
vWc3aj

Go to company page Oracle

vWc3aj
Jul 25, 2021 12 Comments

Let’s say I have some Oracle stock vested over time. Some are long some short. Which lot should I sell?

Assume current stock price is $80. My goal is to minimize tax. I just need to cash some stock.

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TOP 12 Comments
  • Google / Eng
    dogfoodie

    Go to company page Google Eng

    dogfoodie
    It really depends on your outlook for the stock. If you want to minimize the taxes and retain the most stock, selling short will actually have a better yield in your example. If you are wanting to slowly divest yourself of Oracle stock then sell long.
    Jul 25, 2021 5
    • Google / Eng
      dogfoodie

      Go to company page Google Eng

      dogfoodie
      Let's say you want to retain the most stock you can because you are bullish, but want to make a one-time purchase. You pick the lots with the minimal tax liability first since your proceeds after taxes are higher. Your example highlights this is not about long or short exclusively.
      Jul 25, 2021
    • Oracle
      vWc3aj

      Go to company page Oracle

      vWc3aj
      OP
      I am not diversifying. I just need some cash. So lowering tax is my main goal.
      Jul 25, 2021
  • LinkedIn / IT
    Zxzw

    Go to company page LinkedIn IT

    Zxzw
    Why would you sell short vested at all??
    Jul 25, 2021 0
  • I would sell all Oracle stocks
    Jul 25, 2021 1
  • Amazon
    boyoboy

    Go to company page Amazon

    PRE
    Microsoft, Oracle
    boyoboy
    keep taxes low. Let’s say if you sell 100 you got at 50, the profit is 40, you need to pay 800 in taxes in long-term taxes. The same 100 at 70, the taxable amount is 2000, could pay max of 740. I wonder how this many people got tricked for this and gave wrong answer😜

    I assumed 90 😀.
    Jul 25, 2021 1
    • Oracle
      vWc3aj

      Go to company page Oracle

      vWc3aj
      OP
      It’s close to 90 these days. So are you suggesting to sell the short ones? My goal is to minimize tax. I just need some cash. Bought my wife some expensive gifts.
      Jul 25, 2021
  • Short vested so you pay less tax
    Jul 25, 2021 0