After graduating, Watsa worked for the insurance company Confederation Life. In 1984, he started an investment firm with his former boss Tony Hamblin, called Hamblin Watsa Investment Counsel.[12] In 1985, Watsa took over Markel Financial, a small Canadian trucking insurance company that was verging on bankruptcy,[13] and renamed it Fairfax Financial Holdings.[12] He helped grow the company, where it reached annual revenues of $8 billion a year in 2012.[12] Despite his success, he largely stayed out of the public eye, only beginning to hold investor conference calls in 2001.[12][13]
On 22 January 2012, it was reported he was to be appointed to the board of directors of Research In Motion (RIM) in the company's largest ever corporate shakeup. Watsa resigned in August 2013, but kept his investment in the company. On 23 September 2013, BlackBerry announced that it had signed a letter of intent to be acquired by Fairfax Financial Holdings in a $4.7 billion deal.[14] Fairfax Financial Holdings is "the largest insurer of the for-profit bail industry in the U.S."[15]
In April 2017, Watsa brought attention to concerns of a real estate bubble in Toronto. He asserts that most Canadian banks cannot survive a 50% drop in the value of real estate. "It's going to come down, and a lot of people are going to get hurt" said Watsa during Fairfax's annual general meeting.[16]
Volunteering
He is a member of the Board of Trustees of The Hospital for Sick Children, a member of the Advisory Board for the Richard Ivey School of Business, a member of the Board of Directors of the Royal Ontario Museum Foundation, and Chairman of the Investment Committee of St. Paul's Anglican Church.
