Q: Hi 5i team,
I’ve recently sold some of my SHOP position in a taxable account (the share price has risen ~15-fold since purchase about 2-1/2 years ago, and even after this partial disposition, SHOP remains my biggest overall position—thank you for this excellent recommendation!). Now, I want to reduce the tax hit, and so I am planning to sell positions in BMO, BNS, and SU, with aim to rebuy after 31 days (to avoid superficial loss), as these 3 securities are core holdings in my portfolio. In general, when I do tax loss selling, I try to maintain an economic position in the types of companies I am selling, because I’m always anxious the shares will rise during the 30-day waiting period (indeed, frustrating increases in stock prices during the 30-day waiting period seem to happen quite often, at least in my experience). So, my question is: Can you recommend a security (or securities) to maintain economic exposure to BMO/BNS, as well as to SU, for the 30-day waiting period? (For perspective, I’m planning to sell ~$185,000 worth of BMO/BNS, as well as ~$72,000 worth of SU; when I rebuy BMO/BNS/SU, I would then sell the temporary holdings I bought to maintain the economic position.). Would you buy a Canadian bank ETF and Canadian oil sector ETF, to maintain these economic positions (and please recommend some appropriate securities), or rather other individual Canadian banks or individual oil companies (and please recommend some appropriate securities)? Also interested in your philosophical thoughts about how to handle the situation of tax loss selling, which arises every so often, especially now during pandemic, when there is wide variety of individual security performance (some big winners, but also some high-quality stocks that are—hopefully temporarily—depressed in price) as well as higher-than-usual volatility.
Ted
I’ve recently sold some of my SHOP position in a taxable account (the share price has risen ~15-fold since purchase about 2-1/2 years ago, and even after this partial disposition, SHOP remains my biggest overall position—thank you for this excellent recommendation!). Now, I want to reduce the tax hit, and so I am planning to sell positions in BMO, BNS, and SU, with aim to rebuy after 31 days (to avoid superficial loss), as these 3 securities are core holdings in my portfolio. In general, when I do tax loss selling, I try to maintain an economic position in the types of companies I am selling, because I’m always anxious the shares will rise during the 30-day waiting period (indeed, frustrating increases in stock prices during the 30-day waiting period seem to happen quite often, at least in my experience). So, my question is: Can you recommend a security (or securities) to maintain economic exposure to BMO/BNS, as well as to SU, for the 30-day waiting period? (For perspective, I’m planning to sell ~$185,000 worth of BMO/BNS, as well as ~$72,000 worth of SU; when I rebuy BMO/BNS/SU, I would then sell the temporary holdings I bought to maintain the economic position.). Would you buy a Canadian bank ETF and Canadian oil sector ETF, to maintain these economic positions (and please recommend some appropriate securities), or rather other individual Canadian banks or individual oil companies (and please recommend some appropriate securities)? Also interested in your philosophical thoughts about how to handle the situation of tax loss selling, which arises every so often, especially now during pandemic, when there is wide variety of individual security performance (some big winners, but also some high-quality stocks that are—hopefully temporarily—depressed in price) as well as higher-than-usual volatility.
Ted
