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Investment Q&A

Not investment advice or solicitation to buy/sell securities. Do your own due diligence and/or consult an advisor.

Q: I have two questions re: tax loss selling. I have a three year old gain that I can offset by selling the above holdings.

1. First please help me with the math. If I buy a stock for $100, sell it for $90, I have a loss of $10 which would mean I can expect a $2.50 tax loss at a 25% rate. Does this mean that if I wanted to buy the stock back after 30 days, I would only be better off if I buy it back at less than 92.50 per share? Do you have a threshold whereby you must be down by a certain amount to justify a tax loss sale? e.g. 20%? Unless of course you are walking away from a company.

2. Which of the companies listed would you consider buying back after 30 days? I have too many holdings as it is so may just let them all go unless something is particularly interesting. I am overweight technology, underweight everything else but otherwise have a broad mix of funds and stocks.
Read Answer Asked by Dale on December 20, 2024
Q: I would like to do some tax loss selling and was wondering if you might be able to rank RBLX, SQ, TOY, GH, OVV, and COW in order from those with the least potential to recover over the next year, to the most potential. I appreciated your help last year on the same topic. If I were to sell them all, are there any you would consider buying back after 30 days? Thanks.
Read Answer Asked by Kim on August 14, 2024
Q: What is your opinion of Money Lion? How do its prospects compare to, for example, SQ, STNE, PYPL or PAGS?
Thanxx!
Read Answer Asked by David on March 25, 2024
Q: HI folks
Sadly, I am down on all of these somewhere between 60 to 95%!!! They mostly but not all started out as somewhat small positions 2 to 4 years ago! I have time to wait longer but: 1)are there any that are absolute failures and therefore should be sold. 2) Would you please rate the selIs from 1 to 10 ..10 being the absolute SELL. 3)How many years should I give these? (tough to answer but just a guess). I will not get much at all for any of them! Please take as many credits as you see fit.
Much Thanks and happy Family weekend
Read Answer Asked by El-ann on February 21, 2024
Q: I was wondering if you knew much about FedNow. Online it says it will not replace apps like Venmo or Cash App, as it will depend on if your bank and the bank you are sending to opt in. But why would a bank not opt in? It sounds like many banks are already gearing up to implement it this summer. Once fully implemented at US banks, will it be similar to Canadian e-transfers? Why would customers not use it for P2P payments, such as splitting a tab, if it is free, just we we do here in Canada? Thanks.
Read Answer Asked by Kim on February 07, 2024
Q: I am looking at some of my struggling stocks- any comments on whether greener pastures are better found elsewhere and where to go?
Read Answer Asked by Peter on January 17, 2024
Q: Hello, I am down 25%+ on all of these companies and looking to do some tax loss selling prior to yearend. Can you order these companies in terms of what you would sell first? Would you rank these companies as Sells or Holds (or even Buys)? I am a long term investor, not a trader, so I'm hesitant to sell only to rebuy later, or to average down. I have some ability to do a tax loss carry back to recoup some of my losses from prior years (plus minimize my 2023 taxes).
Read Answer Asked by Dale on December 21, 2023
Q: Hello Peter,
Would the fintech stocks be classified under technology stocks similar to Amazon, Google, etc or are they seen as more financial ? if there is a rotation out of tech, would the fintechs be hit accordingly? Thanks very much
Read Answer Asked by umedali on December 11, 2023
Q: I would like to do some tax loss selling and was wondering if you might be able to rank ILLM, UPST, OVV, TOY, SQ, GH, FLGT, and COW in order from those with the least potential to recover over the next year, to the most potential. If I were to sell them all, are there any you would consider buying back after 30 days? Thanks.
Read Answer Asked by Kim on November 22, 2023
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