Wealthsimple Canadian money guru Jonathan Chevreau has made his share of good investments. He said the smartest investment he ever made was buying Apple stock right after the iPod was launched. But that was quickly followed by his dumbest move: selling the shares one year later. I guess I'm sort of the poster child for saving. I’m a writer, and writing involves taking the sacred oath of poverty—it's not really the most lucrative profession.