Motley Fool Money Our Biggest Regret
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Sep 8, 2025 The hosts dive into their biggest investment regrets, sharing haunting stories of stock sales they wish they could take back. They explore potential growth in stocks like Starbucks and how market pressures might influence future performance. The conversation also highlights small-cap companies and real estate opportunities as rates shift. To keep things lively, they play an engaging game analyzing winners and losers, making financial discussions both informative and entertaining.
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Regret From Boredom-Led Sales
- Lou Whiteman sold Axos Financial and Lowe's after getting bored and now regrets those sales.
- He warns that selling on a whim for something shinier is the worst reason to exit a position.
Missed Windfalls From Early Sales
- Jason Hall sold Tesla and part of his NVIDIA stake before huge run-ups and also sold Microsoft before Satya Nadella's turnaround.
- He notes some sells were due to impatience or position-size concerns rather than business thesis changes.
Netflix Stake Whittled Down Over Time
- Rick Munarriz bought Netflix in 2002 and gradually sold 99% of his position over 23 years.
- He calls this his biggest regret because the remaining stake would be worth millions today.