He went from working in a factory to being rich enough to retire at 32—but 3 decades later, this millionaire still works and takes public transport

Bill Holland achieved what many people spend their entire careers chasing: by age 32, he had made enough money to retire for good. But over three decades later, the now-67-year-old still hasn’t hung up his hat.

The former CEO of CI Financial, one of Canada’s largest investment management firms, didn’t take a conventional path to the top. Despite graduating from Toronto’s York University, Holland drifted through a string of self-described “crappy jobs,” like delivering 7Up, working in a factory, and serving as a doorman at a Toronto bar before finding his footing in finance.

At 27, he landed a customer service representative position at Mackenzie Financial Corp.—a demanding job that required fielding roughly 120 customer calls a day, according to a recent profile in Canadian business publication Financial Post.

“People would complain about how hard the job was, but unless you are doing something that involves lifting something heavy, it is not hard,” Holland said.

Within five years, he had capitalized on the booming mutual fund industry and had accumulated enough wealth to retire—a success he attributed to timing as much as talent. 

“A lot of people who have disproportionate success, for the most part, are normal people and if they are being honest with you, they will tell you that they got really lucky,” he said. “I got really lucky.”

But instead of walking away, Holland doubled down. He joined a small investment firm with about $50........

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