Prem Watsa was rushing down Bloor Street in downtown Toronto one morning in 1974 to get to a job interview at an insurance company called Confederation Life. He was fresh from earning his MBA and looking for his first job in finance in his adopted country. The street was filled with police officers searching for suspects in a bank robbery that had just occurred, and one of them grabbed Watsa, a 23-year-old Indian immigrant, and pinned him against a police cruiser. He protested his innocence, explaining that he was hurrying because he didn’t want to be late for an important meeting. A few minutes later, the cops let him go.
Watsa ultimately got the job and, after 10 years working as an analyst and a money manager at Confederation Life, began building a company that would become Fairfax Financial Holdings, now a C$9 billion ($8.8 billion) conglomerate. It invests in everything from insurance to restaurants to sporting goods; the company owns insurers Crum & Forster and OdysseyRe in the U.S., as well as a stake in the Bank of Ireland. “Prem was this value-based investment manager, and the company was going to be—and a lot of people said they were going to do this—Berkshire Hathaway No. 2,” says Robert Grundleger, founder of Groundlayer Capital in Toronto. “To a degree, he’s succeeded in doing it.”