The Canadian Investor · Braden Dennis & Simon Belanger

The 7 Biggest Investment Mistakes We’ve Made

October 30, 2025·48 min·4 clips
Braden lost 40% of his portfolio by betting too heavily on Bitcoin and tech stocks during the 2022 crash.
Hosts Braden and Simon candidly discuss their biggest investment mistakes, including overconcentration in high-growth stocks, valuation errors, home bias, and poor crypto bets. They share personal stories to highlight lessons on diversification, risk management, and emotional discipline for investors.

As heard by us

A blunt look at investing mistakes, home bias, and the habits that quietly drag on returns.

The episode looks at the investing mistakes people like to smooth over, then does the less comfortable work of naming them. The hosts revisit their own blind spots and bad calls, including a long stretch of heavy Canadian exposure and an income first approach that lagged the…

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Why you'd press play

If home bias has been your default, this one pushes back with a very personal, clear-eyed case against it.

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