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Or sign-in if you have an account.“Philanthropy gives you a purpose,” says Bill Holland. "There is no better way to spend your time." Photo by Photo by Peter J Thompson/National PostWe independently select everything we recommend. 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He had no idea what he wanted to do when he grew up, beyond knowing he didn’t want to live as lean as his parents had while raising six kids in Toronto in the 1960s and 1970s on his father’s salary as a university professor.Holland’s lack of academic direction saw him cycle through a series of “crappy” jobs — delivering pop, working in a factory, working as a doorman at a midtown bar — until 1985, when he became a customer service representative at Mackenzie Financial Corp.Get the latest headlines, breaking news and columns.By signing up you consent to receive the above newsletter from Postmedia Network Inc.A welcome email is on its way. If you don't see it, please check your junk folder.The next issue of Top Stories will soon be in your inbox.We encountered an issue signing you up. Please try again“You would get 120 calls a day and people would complain about how hard the job was, but unless you are doing something that involves lifting something heavy, it is not hard,” he said.At 27, Holland was a virtual greybeard among his younger colleagues, but he was also possessed with a gift for the gab and was unafraid of clocking long hours, attributes that allowed him to shift to sales just as the mutual fund industry in Canada was exploding.“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.”By his arithmetic, he had made enough money to retire at age 32, but instead he joined a small fund company with $50 million in assets under management that grew into CI Financial Corp. and climbed the ladder to become chief executive and then executive board chair. Philanthropist and Former CI Financial Group CEO Bill Holland at his Toronto office, Monday June 29, 2026. Photo by Photo by Peter J Thompson/National PostCI had about $140 billion in assets under management when it was taken private by the United Arab Emirates sovereign wealth fund last year in a deal that valued its publicly traded shares at $32 apiece. Holland still owned a healthy number of shares at the time, but he has since divested himself of them.Accumulating a ton of money has allowed him to give a lot of it away. For example, Toronto’s Sunnybrook Holland Orthopaedic and Arthritic Centre and the Holland Bloorview Kids Rehabilitation Hospital are not named after a region in the Netherlands, but a finance guy who got “lucky.”Holland is a bit shy discussing the actual numbers, but Sandra Hawken, chief executive of Holland Bloorview’s foundation, said the 67-year-old has donated close to $40 million to the hospital.But even more incredible, she said, have been his efforts as a board member with an uncanny talent for twisting arms and wringing donations out of others. On that front, his running total of funds raised stands at $50 million while, in aggregate, his personal donations, chiefly to the two institutions bearing his name, ring in at well over $100 million.“Bill is the most formidable fundraiser I have ever met. It’s impossible to say no to him,” Hawken said. “It is not just because he’s persuasive, but he truly cares about the kids and families and it shows.”Holland has been involved with the facility that cares for children with complex health challenges — from muscular dystrophy to serious brain injuries — for more than 20 years and rarely leaves the place without tears.“These kids are dealing with profound challenges; it is unbelievable,” he said.After one such visit, he asked his daughter, who was six at the time, how much money he should donate. She paused, then said, “You should give them half your money.” Holland laughs at the memory. Accumulating a ton of money has allowed Bill Holland to give a lot of it away. Photo by Photo by Peter J Thompson/National Post“Smart kid,” he said.Holland does not need to work, but he keeps an office in downtown Toronto anyway and takes public transit to get to it from his home in the city’s north end five days a week. He walks a lot and keeps his fingers in several investment pies, including Florida and Georgia real estate.In the aftermath of the 2008 financial crisis, he went on a real estate buying binge in the southern U.S., mostly in the Fort Lauderdale, Fla., area, where some properties were selling at a 90 per cent discount.He also snapped up 500 houses in Atlanta and bought a lot of land, operating on the premise it would go up in price someday and somebody would want to buy it. Hotel and condo developers have since been among the somebodies.“By a mile, real estate would be my biggest investment,” he said.His investment philosophy is to “bet the jockey.” Translation: find the right person with drive and smarts and you might just hit a home run. In Florida, he found Dev Motwani, who is managing partner of the real estate enterprise and is “all jockey.”Holland can size up a strip of beachfront property in a sunny clime and wrap his imagination around why it might go up in value, but he simply does not understand the stratospheric, multitrillion-dollar valuations of companies such as Space Exploration Technologies Corp. and Nvidia Corp.“Can a business be worth more than Canada?” he said. “I don’t get it. We can live without those chips, but we can’t live without water, oil, natural gas and mineral resources.” Bill Holland’s uncanny talent for twisting arms and wringing donations out of others has raised millions for medical care. Photo by Photo by Peter J Thompson/National PostPhilanthropy is another societal necessity, he said, and Canadians are generally “terrible” at it. Most assume the taxes we pay fund our hospitals and take care of things, but Holland said if you have ever spent time in a hospital, it is pretty clear there is an abundance of need that public funding does not account for. Hence, his side hustle as an arm-twister in the service of raising money.Holland also keeps an office in Florida, where all the Canadian billionaires could fit on one floor while the other 15 would be full of American billionaires. In other words, there is a lot more money in the U.S. and a lot more people who are willing to part with it for charity.“If you are rich in the U.S., you give money away, but I could name you 100 very rich Canadians who give no money away,” he said, without naming names.If he has another beef, it is golf. Some of his buddies are into it, but he hates the game, a dislike matched, perhaps, only by his dislike for the Justin Trudeau Liberal era. Some of the rich people he knows who are generous have grown so fed up with Canada that they moved elsewhere. At times, he admits to being so fed up that he has contemplated doing the same.“The hard thing in Canada is that we would rather live worse and stick it to the rich guy, and our politicians get that and they play to that,” he said.For now, Holland is staying put. Unlike many rich Torontonians, he eschews cottage country life for his life in the big city, where there is always more work to be done.“Philanthropy gives you a purpose,” he said. “Sure, you can give a ton of money away and not have to think about it and be happy as a lark, but if you get involved, and you think about the issues — the use and the need — there is no better way to spend your time.” Join the Conversation This website uses cookies to personalize your content (including ads), and allows us to analyze our traffic. Read more about cookies here. 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