Mr. Lucky: Bay Street legend Bill Holland has donated tens of millions and raised tens more to help kids

Article content

“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.”

Article content

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.

Article content

“These kids are dealing with profound challenges; it is unbelievable,” he said.

Article content

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.

Article content

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

Article content

“Smart kid,” he said.

Article content

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.

Article content

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.

Article content

Article content

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.

Article content

“By a mile, real estate would be my biggest investment,” he said.

Article content

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.”

Article content

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.

Article content

“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.”

Article content

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 Post

Article content

Philanthropy 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.

Article content

Article content

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.

Article content

“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.

Article content

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.

Article content

“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.

Article content

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.

Article content

“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.”

Article content

Article content

Article content