Jim Pattison roars through rural Saskatchewan in his silver pickup truck, barreling down the prairie road that runs arrow-straight to the horizon. Tossed into the back seat is a sleeping bag and crimson pillow—the unlikely berth for Canada’s self-made billionaire when he can’t find a motel.

Observing the speed limit appears optional, using the turn signal an afterthought. Not that there’s much in the way of obstacles—only shimmering fields of wheat stretching across a terrain so flat that if you lost your dog, as the saying goes, you could watch it run away for three days.

It’s here in Canada’s vast breadbasket that Pattison was born and where, at age 90, he’s overseeing one of the newest arms of his C$10 billion ($7.4 billion) empire: Pattison Agriculture, a string of John Deere equipment dealerships serving 21 million acres of farmland.

“We’re seeing more opportunities than we ever have,” says Pattison, steering confidently, his diminutive frame overwhelmed by the cavernous, black leather seats of his Ram 1500 Laramie truck. “There are still lots of opportunities with all the changes going on in the world.”

The road trip offers a rare glimpse of the intensely private Pattison, Canada’s third-richest man, who created his iconic business group in seeming defiance of modern empire-building. He eschews emails, carries a cell phone but barely checks it, and can count on one hand the number of times his group has used an investment bank in recent memory.

Pattison is often dubbed Canada’s Warren Buffett—a trope that underscores how relatively unknown he remains outside Canada despite a conglomerate that operates in 85 countries across a dizzying array of industries: supermarkets, lumber, fisheries, disposable packaging for KFC, billboards across Canada and ownership of the No. 1 copyrighted best-seller of all time, the “Guinness World Records.” Believe it or not, he even owns the Ripley Entertainment Inc. empire.

“Back in Omaha, I’m known as the Jim Pattison of the United States,” Buffett quipped in December 2018 when he surprised Pattison onstage in Toronto as the Canadian billionaire was inducted into the country’s Walk of Fame. Pattison dismisses the comparison. “Warren Buffett is in a class all by himself,” he insists.

Pattison has driven 1,700 kilometers (1,000 miles) from the Jim Pattison Group Inc. headquarters in Vancouver, across the towering Canadian Rockies to the prairies where he’s acquired four farm equipment companies to create Pattison Agriculture. He likes to drop in unannounced on his holdings, including his supermarkets and dealerships, but word quickly gets around.

“You’re the man we’ve all been waiting for,” says the receptionist at the dealership in Moosomin, Saskatchewan (population 3,100). “You got a call, did ya?” he says with a grin as he shuffles into the shop, helping himself to popcorn as he quizzes employees.

He listens intently as they share their pain points—the dearth of mechanics, narrowing margins on new equipment sales, and the intolerable noise in the cab of a new tractor that has farmers complaining. He occasionally pulls out a pad and an array of colored pens but mostly relies on his still razor-sharp memory.

***

Pattison’s rags-to-riches story recalls a different era. Born in Luseland during the Great Depression, he wore clothes stitched together from the castoffs of other children because money was so tight. The family moved out west when he was 6, settling in Vancouver’s gritty east side. In the summers he’d return to the family homestead in Saskatchewan, where the land was still plowed by horses. A natural salesman, he was touting seeds door-to-door at age 7 and within a few years was trouncing grown men in a competition to sell the most subscriptions of the Saturday Evening Post.

His path to a fortune now worth about $6.3 billion began with a Pontiac Buick dealership in 1961. He bought it with a C$40,000 Royal Bank of Canada loan after persuading the local manager to exceed the branch’s lending limit fivefold. He keeps the yellowing, handwritten financial statements from that first year in a clear plastic folder.

Pattison says his favorite job is still being a used-car salesman. “If I had to, I could always go back.” He parlayed that into a global business empire over the next five decades, completing hundreds of acquisitions to create the nation’s second-largest private company.

Pattison’s folksy approach belies the tectonic shifts facing some of his businesses. Magazines in their heyday were his best business of all, he says, but people aren’t reading print anymore—the group agreed to sell its U.S. magazine distribution business in late 2018. His car dealerships have seen ride-sharing and autonomous driving threaten to accelerate the potential demise of vehicle ownership.

One of his biggest stakes in an outside company is Westshore Terminals Investment Corp., North America’s biggest coal export facility, in Vancouver—a cash cow with a shrinking life span in an era of tightening emission standards. His biggest public holding is a controlling stake in Canfor Corp., the lumber company that has plunged about 35 percent in 2018 as the U.S. housing market slows.

“Some businesses—we’re exposed like heck,” he says. “But we make the best of what we got. This is part of why I’ve got a job.”

Behind that stodgy image are businesses navigating technological disruption.

The Pattison Agriculture dealership in Yorkton is a newly renovated hub in a region of 60,000-acre farms, some bigger than Lichtenstein. Most of the equipment inside costs half a million dollars each; some customers will drop as much as C$40 million a year in purchases.

“See what it costs to be a farmer these days?” Pattison asks as he walks around the warehouse, his 5-foot-6-inch frame dwarfed by the tires on some of the machines. “They’ll be less and less small farms. What’s happening is consolidation, consolidation, consolidation.”

Pattison’s low profile is occasionally punctuated by a well-calculated spectacle. When the provocative, flesh-colored gown worn by Marilyn Monroe in 1962 to sing “Happy Birthday” to then-President John F. Kennedy came up for auction, Pattison rang his son, Jim Jr., who runs the Ripley Entertainment business.

“I almost had a heart attack when I saw what they thought the dress would go for,” Jim Jr. says in a phone interview from Orlando, Florida. “We have to get a return on everything we invest. I didn’t want it.” His father bid for it anyway, paying more than $5 million, making it the most expensive dress in the world.

The company has reaped dividends in publicity from the purchase, Jim Jr. says. News of Ripley’s purchase in 2016 set off a global tweet storm. The dress has drawn crowds to Ripley’s venues across North America, and the garment will soon embark on a world tour, where visitors will be able to try on a true-to-hourglass-size replica of it.

The dress was a rare splurge for a man who started off with so little.

“Most of the time, I didn’t have the money to buy anything that was any good, so I had to buy stuff that nobody wanted,” Pattison explains. “I didn’t know what goodwill was for a long time,” he says of the premium paid in acquisitions for intangible assets like a brand.

Historically, he’s kept the existing management in place after takeovers, and he gives his deputies a long leash. “He trusts people to do their job,” says his son. The organizational hierarchy is as flat as the surrounding prairies.

“My responsibility is to help you be the most competitive in this area,” Pattison Sr. often tells his employees, instructing them to take down his number in case they hit a wall. “But we can’t fix it if we don’t know what the problem is.”

In return, he demands results. In his early years running a car dealership, Pattison would fire the lowest-performing salesman on the lot every month. In practice, he says he was more flexible and intuitive.

“The best salesman I ever had didn’t sell a car for two months, but I stuck with him,” says Pattison. “It just took me a while to decide what he needed to help him.”

***

For a company with 45,000 employees, it’s still run a bit like a startup. To this day, the corporate headquarters on the 18th floor overlooking Vancouver Harbour and Stanley Park doesn’t have a human resources department. The most important hiring decisions over the years have been made by Pattison and Maureen Chant, his executive assistant of more than 50 years.

Chant may have the most understated job title in corporate Canada. With her shock of snow-white hair and round face, she looks more like a kindly grandmother than the invisible hand that’s kept Pattison and his incongruous empire running.

Chant advises the group’s nearly 30 business divisions and has influenced who runs them. She oversees Pattison’s $25 million, 150-foot yacht, the “Nova Spirit,” which has hosted everyone from Princess Diana to Oprah Winfrey. She also looks after his private jets, his Vancouver office condo and a Palm Springs property (previously owned by Frank Sinatra) where Pattison gathers his top lieutenants once a year. For most of her career, Chant has worked seven days a week.

She first came to his notice as the night switchboard operator when she’d listen to him practicing his speeches and tell him he was “no good.” In the late 1970s, when Pattison made a disastrous foray into commodities trading, Chant was fielding the margin calls from brokers as a $78 million paper profit evaporated.

Realizing Pattison wouldn’t cut his losses, she told him he was out of cash. “In the meantime, without telling me, she tucked away $6 million that I didn’t know I had—otherwise I’d have just spent it,” Pattison recounts.

Asked if he’d ever considered giving Chant, 79, a more prominent title, Pattison seems surprised—it’s never occurred to him, he says. “She’s been a major influence,” he says. “She can retire anytime she wants, but she works because hopefully she likes it.”

***

While he loves to regale visitors about his company’s past, Pattison is firmly focused on a disruptive future.

“One thing is for sure, things are going to be significantly different 25 years from now,” he says, back in the truck. “You saw those big tractors—who would ever have dreamed that that kind of equipment would be seeding the land or harvesting it?”

On this trip, Pattison has picked up an old pal on the way—Bill Stinson, 83, head of the Westshore coal business and a former chairman of Canadian Pacific Railway Ltd. The two business titans at times struggle with Google Maps and fumble to see if there’s a paper map on board. But soon they’re back on their way, resuming their conversation about the world’s inexorable churn. Drones could deliver groceries. Autonomous trucks could overhaul distribution. Companies are getting bigger; dogs are definitely getting smaller.

“You see them, Bill, in downtown Vancouver? They got dogs now the size of cats,” Pattison marvels.

The afternoon’s wearing on, and Pattison is impatient to cram in a couple more dealerships before finding a motel for the night. Neither he nor Stinson has eaten since their 6 a.m. breakfast at the Days Inn that morning in Yorkton. When they finish their loop of Saskatchewan and Manitoba in a few days, they’ll drive home in one straight shot, taking turns at the wheel for the 22-hour drive.

Does he ever take a vacation? “Well, I get 365 days,” he quips. “If you like your work, it’s not work.”