7 Stocks We Sold Too Early… And Still Regret

Simon Belanger and Dan Kent of The Canadian Investor Podcast reflect on seven stocks they sold too early—each decision now a source of regret, yet also a lesson in long-term investing. From Apple to Alphabet, Shopify, Fairfax Financial, NuVista Energy, Brookfield Corporation, and even a near-purchase of Qantas Services, the hosts reveal how emotional reactions, overconfidence, and complexity led to missed opportunities. Simon sold Apple in 2013 to fund a home purchase that turned into a financial black hole, losing over 40% on the property while Apple soared 1700% since. Dan sold Apple in 2012 after a four-year stagnation, missing a 1200% gain. Their regrets aren’t just about money—they’re about mindset: the danger of selling too soon due to boredom, fear, or overconfidence in a thesis. The episode becomes a masterclass in patience, conviction, and the psychological traps of investing. Even when logic seemed sound—like doubting Google’s AI resilience or fearing oil’s collapse during the pandemic—the market proved them wrong. Yet, they emphasize that regret is inevitable, and the real win is learning from it. The final segment on Lululemon’s new CEO, Heidi O'Neil, adds a timely twist: sometimes, the market overreacts to headlines, creating potential buying opportunities in overlooked companies. The key takeaway isn’t just about which stocks to hold—it’s about building a process that survives emotional storms.