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Doug, a 69-year-old retiree residing on the West Coast, has applied an “instinctual” momentum approach to grow his tax-free savings account to $500,000. His TFSA was opened in 2009 and annual contributions were maxed out (totalling $109,000).
Doug graduated from law school in the 1980s and went to work in the financial sector, mainly at brokerage houses on Bay Street. He also took the Canadian Securities Course that advisers need to pass in order to analyze securities and recommend investments.
This career path gave him the acumen to manage his own portfolio. It also delivered a tidy windfall: He was a shareholder in one brokerage, which proved to be “a very good investment” when his firm was acquired by another brokerage.
He semi-retired in his mid-40s and follows his investments daily. “It’s a passion and a hobby,” Doug declares. His portfolio is in the “high seven figures” – or “low eight figures,” if family assets are included. It is allocated 100 per cent to stocks.
Doug has about 30 stocks inside registered retirement savings plans and another 30 or so stocks in non-registered accounts. They are typically solid companies such as Royal Bank of Canada (RY-T), Enbridge Inc. (ENB-T) and Exchange Income Corp. (EIF-T).
This septuagenarian’s TFSA has gone off the rails
For these “serious investments,” he looks at company fundamentals to assess long-term potential. Dividend yields are important: They are needed for covering living expenses because he “does not have a pension other than CPP.”
Then there are his “fun” (speculative) investments, currently consisting of seven stocks in his TFSA. In this account, which is “a very small part” of his total portfolio, Doug is more of a momentum investor, looking for stocks in uptrends.
“In my TFSA, I like to ride companies that are doing well,” Doug says. They usually are promising businesses that are growing rapidly. Cyclical stocks are avoided. He has a watch list of more than 50 stocks on Yahoo Finance.
In his TFSA, he tries “to sell quickly when an investment isn’t performing.” Sometimes, the Sell button is smashed too fast, and he misses out on a big upswing. But overall, he believes cutting weak stocks quickly keeps his portfolio out of trouble.
He learned early about trouble. Shortly after entering the financial industry, he had a front-row seat for the market crash on Oct. 19, 1987, when the Dow Jones Industrial Average plunged 22 per cent. “I’ve survived several ‘crashes’ since; they can be sobering, but also good lessons.”
Retired 82-year-old lawyer builds $600,000 TFSA with a ‘buy what you know’ strategy
Doug acknowledges that his approach to picking TFSA stocks “is not very scientific.” Having spent years working in the financial industry and managing his own portfolio, he relies on intuition a fair amount. “To say it’s instinct sounds a bit absurd, but I do think it’s an element.”
Here are some of his past TFSA trades:
Doug bought shares in Lightspeed Commerce Inc. (LSPD-T), a point-of-sale and e-commerce software firm, between 2019 and 2021 at an average cost near $56, and sold them in September, 2021, at $151.
He bought shares in Nuvei Corp. (NVEI-T) in December, 2020, at $73 and sold them in September, 2021, at $163.50. Nuvei is a provider of payment technology solutions (and was taken private in late 2024).
He also bought shares in an online retailer of contact lenses and eyeglasses, Kits Eyewear Ltd. (KITS-T), at $9.50 in January, 2025, and sold them in August, 2025, at just over $16.50.
He currently holds:
Brookfield Corp. (BN-T) with an unrealized gain of $45,250. The alternative-asset investor and manager has “done very well over time” through long-term wealth building, despite periods of slower growth.
E-commerce platform Shopify Inc. (SHOP-T) is another position. Doug does not intend to sell it even though it recently lost some momentum. “I still think it’s a great company and I’m willing to be patient,” he explains.
Kraken Robotics Inc. (PNG-X), with an unrealized gain of $45,630. The company supplies sonar and optical sensors, batteries and underwater robotics equipment for military and commercial applications. It is a play on the defence space, which the federal government is now building up.
What an expert says
Providing his thoughts on Doug’s TFSA is Ross McShane, an advice-only financial planner, educator and coach in the Ottawa area who holds several professional designations.
Doug has experience in the investment industry on his side and some education in the form of the Canadian Securities Course. Many DIY investors do not have his background, or they do not invest the time to do the necessary research.
Instead, they buy companies that they know or hear about, or even on recommendations from a friend. They struggle with when to trim overvalued positions or buy into undervalued companies.
Many do not have the ability to do the fundamental analysis to determine company valuations and lean toward ETFs. Doug, on the other hand, is doing his due diligence to assess company valuations and make better decisions.
A 100-per-cent equity allocation is fine if the cash flow is sufficient to cover his expenses, as it does in his case. He has built himself his own healthy pension that is indexed, as long as his portfolio is holding companies that have sustainable and growing dividends.
Many investors, like Doug, will put their more speculative or “high flyers” in their TFSAs, seeking maximum tax-free growth. However, a downside is that capital losses cannot be used in a TFSA, whereas they can be used in a non-registered account. I do suggest that he rely less on “instinct” and focus more on the fundamentals. The key is to remain disciplined in his approach.
Larry MacDonald is author of The Shopify Story and blogs at Shopify’s Journey