The Canadian Investor The 7 Best Investment Decisions We’ve Ever Made
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Nov 3, 2025 Simon and Dan reveal their best investment decisions, featuring early Bitcoin investments and strategic gold buys. They share tips on capitalizing on US tech amidst market pessimism and recount the profitable acquisition of Terraform Power. Dan's approach to Aritzia during its downturn led to significant gains, while Simon’s timing during the COVID crash with firms like Visa and Microsoft paid off handsomely. The duo also dives into the psychology of investing, exploring why losses stick in our minds more than wins.
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Early Bitcoin Conviction
- Simon bought Bitcoin first in 2018 and again in April 2020 and rode a volatile multi-year roller coaster.
- He endured ~40% drawdowns in 2022 but held conviction and kept accumulating over time.
Late Bitcoin Buyer, Small High-Conviction Bets
- Dan bought Bitcoin in 2021 after initially dismissing it and used a small position as a high-upside bet.
- He scaled positions up and down, admitting regret for trimming at highs but stayed comfortable with limited downside risk.
Allocate Small Amounts To Asymmetric Bets
- Consider placing a small allocation (0.5–2%) to asymmetric bets you don't fully understand but have huge upside.
- The worst-case is total loss while the upside can be orders of magnitude higher, making the math attractive.