For Roy Thomson, it all started with a $500 investment in a northern Ontario radio station during the Great Depression. For Fred DeGasperis, it was a truck he purchased with his brother to do construction jobs around Toronto in the 1950s. For Terry Matthews, it was an ill-fated plan to build hotel fire alarms. The creation myth for each member of the Rich 100 usually begins in the same humble, unassuming manner and ends with the same result: wealth, and a lot of it. And because these people have been at it for decades, they keep getting fabulously, obscenely, gloriously richer.

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Collectively, the individuals on the Rich 100 are worth $230 billion, more than the total gross domestic product of many countries in the world, including New Zealand, Ireland and Portugal. And this year has been one of their best ever. Their combined net worth surged by more than 15%, the biggest increase since 2000. The reward for the wealthy is partly a result of a worldwide market rally—the S&P 500 Index rose more than 16%, while the Nasdaq increased 17%. The S&P/TSX composite, which is more heavily skewed toward commodities, is up just over 6%. While the actual economies of Canada and the U.S. aren’t faring particularly well, so long as the U.S. Federal Reserve maintains its stimulus program, stock markets will tick higher.

They may not always look like titans of industry (Onex CEO Gerry Schwartz and Indigo CEO Heather Reisman were spotted at one of her stores one recent weekend in decidedly non-business attire—he wore track pants, her hair was pulled back with a red scrunchie), but the individuals on this list are particularly good at ensuring they come out on top.

The retail and grocery sectors in Canada have been under siege from Target and Walmart, and yet retailers and grocers typically enjoyed double-digit increases in their fortunes. The Westons and the Sobeys, for example, took aggressive defensive measures to stay competitive. Loblaw snagged Shoppers Drug Mart, and Sobeys bought Safeway Canada. Investors are loving the strategy and sent shares in both companies soaring higher.

As for the Westons and the Sobeys themselves, their net worths shot up by $2.1 billion and $598 million, respectively—gains of roughly 25%. Dollarama founder Larry Rossy has found himself growing richer ever since the recession, when cashstrapped Canadians flocked to his stores in search of cheap goods. Rossy’s net worth bumped up $143 million—an 11% surge. Convenience-store magnate Alain Bouchard, meanwhile, looked beyond Canada and scooped up a European chain last year, combining it with his company, Alimentation Couche-Tard. Investors rewarded the stock. As a major shareholder, Bouchard’s net worth skyrocketed by 48%—almost $500 million.

Few members actually decreased in net worth. Anyone tied to mining, which is undergoing a global rout, suffered badly, however. Gold bug Eric Sprott was dealt a huge blow, falling 17% (more than $200 million). Silver-tongued mining promoter Robert Friedland dropped 14% ($42 million). Rob McEwen’s mining company is struggling so badly he tumbled off the Rich List entirely.

But overall, it’s been a banner year for the super rich. The cutoff for making the list in 2013 was $728 million, compared to $309.6 million in 1999. In a few years the Rich List will likely consist entirely of billionaires. Increasingly the Rich 100 is becoming a class of its own—sailing farther away not only from most of us, but from most multimillionaires, too. Newcomers don’t appear very often, and when they do, it’s often simply because they have managed to dodge the spotlight until now. That’s the case with this year’s new addition, Vancouver’s Aquilini family, which had consistently flown under the radar until an acrimonious divorce proceeding revealed massive wealth and diverse holdings, spanning real estate and agriculture.

More than a quarter of the list is made up of families like the Aquilinis, and while it may be hard to feel sympathy for the pecadilloes of the rich, it’s worth pointing out that being a member of a dynasty comes with its own set of burdens. Roy Thomson, who built a multi-billion-dollar conglomerate, noted in his autobiography that his son, Ken, and his grandsons would have no choice but to manage the family business. “These Thomson boys …are not going to be able to, even if they want to, shrug off these responsibilities,” he wrote. Grandson David, a chairman of the family holding company today, felt the full weight of the Thomson name growing up. “I learned at a very early age that people did not give a shit about me, and when they did, they wanted something,” he said in a 1993 oral history of the private school he attended in Toronto. “Now I am extremely self-sufficient and rather overly aggressive, I suppose.”

Such an insightful comment by David Thomson, or any of the nation’s ultra rich, is rare. They tend to be private individuals. The topic they’re particularly loath to discuss, as any researcher on this project can tell you, is their net worth. We, on the other hand, just can’t get enough.

Rankings

Top 25 richest people in Canada 2014 Canadian Business magazine’s Rich 100 list is now in its fifteenth year, but those on our roster have been getting wealthy for much longer.

Canadians who gained the most wealth in 2013 These five Canadians saw the biggest percentage gain in their wealth this past year.

Canadians who lost the most wealth in 2013 These five Canadians saw the biggest percentage loss in their wealth this past year.

Top 5 richest people in Ontario Canada’s biggest province has its fair share of wealthy residents. Here are the top five.

Top 5 richest people in Quebec While much of Canada’s wealth has moved West, French Canada still has a number of billionaires.

Top 5 richest people in Alberta Not surprisingly, Canada’s oil capital is home to a lot of rich people too.

Insight

INFOGRAPHIC: If you invested like Canada’s billionaires, would you be rich too? We put together a virtual portfolio of the publicly traded equities held by members of Canadian Business’s Rich 100.

5 ridiculously expensive yachts owned by Canadian billionaires Nothing says you made it like owning your own superyacht. And these billionaires, pulled from Canadian Business’s Rich 100 list, get to enjoy the privilege.

POLL: Most of us overestimate how rich the richest Canadians really are In surveys, Americans tend to underestimate their society’s wealth inequality, but the opposite seems to be true in Canada.

Inside Canada’s most luxurious homes These multimillion-dollar homes are more than a place to hang your hat. Come inside—and please wipe your feet at the front door.

As inequality grows, what should we do with Canada’s rich?: Duncan Hood In a global market, if you’re already near the top in terms of education and skills, you can command a higher wage.

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