Recruiting expats souring on the American Dream could give Canada an economic edge in duel with Trump
Billy Berg can’t quite put a finger on what it was about New York, but while growing up in Toronto, he always imagined he would live there for a few years before heading back to Canada to get on with his life.
Life had other ideas. He applied to two business schools, both in New York, and within hours of arriving at Columbia University, his plan to turn around 18 months later with a degree in hand went out the window.
New York had an indescribable energy to it, a brash, pulsing, work-hard-and-reap-the-spoils spirit that was intoxicating, so leaving town after barely getting a taste of it was unthinkable. The city didn’t care who you were or where you were from, Berg said. All it asked was for your commitment, so he and his Canadian spouse fully committed at work — and at play.
“New York is an incredible place,” he said. “The hustle culture, the ability to just make something out of nothing, if you’re willing to put your shoulder to it and push, that is a purely American trait. It exists elsewhere to some degree, but it is in its crystalline form here.”
Now in their 50s, the Canadian expats are emblematic of an American Dream come true, with high-powered jobs, American-born kids and an American beach house to show for it.
But it is a dream that Berg, who is a senior executive with a consumer technology company and requested a pseudonym for the purposes of this article since popping one’s head above the parapet to speak candidly during Donald Trump’s reign may carry some attendant risks, is finding increasingly difficult to reconcile with his Canadian self.
After all, he is still just a guy from Toronto who supports the Maple Leafs, kicks off his stump speeches at tech conferences by introducing himself as Canadian despite being a dual citizen now, and views universal health care as a human right and the American belief in the right to bear arms as unfathomably bonkers.
But what he finds most troubling today, apart from Trump’s anti-Canadian rhetoric , trade war sabre-rattling, deportations without due process, mass firings of civil servants, defunding of universities, social media trolling and stock-market-roiling economic policy, is that a majority of Americans voted for an encore performance.
“What Trump has brought with him is this wave of mean-spirited, divisive rhetoric, and it gets support from across the country because the Trumpy officials who behave like him are the ones who are winning, and it is incredibly disheartening to see,” he said. “At some point, you have to say to yourself, ‘Look, this is what the country wants because, at some level, it is who they are,’ and once you accept that, then you need to ask yourself, ‘Do I want to continue to live here?’”
Berg does not have an answer to that question, at least not yet, but leaving New York for Toronto or somewhere in Europe is one conversation he and his wife keep circling back to, and they are not the only expats wrestling with the sick feeling that the United States they thought they knew has changed.
Repatriating go-getters from what is perceived as hostile territory and perhaps encouraging some of their disillusioned American pals to come along to help rebuild Canada could be just what the country needs to get an edge, not to mention the economic boost that bringing their capital could provide.
More than 800,000 Canadians live in the U.S. Some moved for higher wages and lower taxes, others went for the weather and others in the recent past just didn’t like Justin Trudeau so much. On the flip side, some Americans have moved the other way, and Canada has benefited from their presence.
According to the U.S. Census Bureau, 126,340 Canadians made the leap south in 2022, with Florida and Texas the most popular destinations. Three years later, Canada is teetering on the brink of a Trump-triggered recession , while Prime Minister Mark Carney has said the country needs to build “big,” build “bold” and build “now.”
Berg, for his part, has been on a roll in tech. But Canadian expats have been winning, creating wealth and making breakthroughs throughout the U.S. economy for decades, in health care, research and development, academics, banking, law, artificial intelligence wizardry, startups and good, old-fashioned, get-stuff-built trades.
“There are some domestic challenges we face in Canada, which makes it a bit more difficult to be competitive with other jurisdictions in terms of attracting talent, but it’s a good problem to have to be able to benefit from somebody else’s problem,” Mahmood Nanji, a policy fellow at the Lawrence National Centre for Policy and Management at Ivey Business School, said. “Right now, in the United States, theirs is a self-inflicted problem.”
But a big, unspoken challenge north of the border in terms of exploiting the situation to Canada’s benefit, in addition to overcoming all the bells and whistles that tend to lure Canucks south in the first place, is that the simple facts of an American life are still appealing to many.
He shoots, he scores
If a young up-and-comer asks Toronto native John Hockin how he came to be cofounder and chief investment officer at Sea Cliff Partners LP, a San Francisco-based public-equity fund, he tells them that working hard, both in and out of the classroom, gives you options.
“I always tell people I went to Yale for the education, which I did because I was a good student, but I really went to Yale because I desperately wanted to play American college hockey; I was super-passionate for the game,” he said.
The former Yale Bulldog goaltender doesn’t get between the pipes too often these days, but, not unlike most old goalies, he has an informed opinion as to how the games he watches on television are played and, despite having lived in the U.S. for much of his life, he still firmly identifies as Canadian.
His wife is also Canadian. They have a cottage in Canada and Hockin flies back and forth between his desk in California and a dock by the lake.
In San Francisco, he said he doesn’t run across too many fire-breathing MAGA types, and there is not a single person in his professional and personal spheres who has not approached him to apologize for Trump’s talk “about the 51st state” and his trade tactics that have put the health of the Canadian economy at risk.
Hockin’s firm invests in American businesses with market values of between US$1 billion and US$10 billion and works with those companies’ management teams and boards. Prior to founding Sea Cliff Partners, he worked at Morgan Stanley and he was once head of public investing at KKR & Co. Inc., a private-equity behemoth with an investment portfolio worth more than US$600 billion.
At each stop along the way, he has added American businesspeople and financiers to his professional network, and despite his love for his native country and many friendships there, moving back to Canada is not a consideration.
“The U.S. is just a bigger market,” he said. “ In terms of access to capital, size and breadth of the equity markets, it is a larger market to invest in.”
That’s not to say Canada hasn’t been on his mind. His uncle, Tom Hockin, was a cabinet minister during the Brian Mulroney era. Post-politics, he worked in the mutual fund industry. His last stop before riding off into the sunset was as Canada’s representative to the International Monetary Fund , a gig that coincided with the great financial crisis of 2008-09.
“I have always admired my uncle, and the one thing I have always thought about longer term for myself because I do have a lot of relationships in the U.S. is how that could be helpful from a Canadian perspective, and could I ever find a role that helps Canada in relation to the U.S.,” he said. “But I have no idea what that role is.”
The other thing is his belief in the inherent goodness of Americans. Even with all the “uncertainty” going on today, he said Americans “ultimately do the right thing” in his experience.
A referendum on whether Trump has been doing the right things will come with the 2026 midterm Congressional elections, but until then, business leaders are going to need to figure out what to do and what not to do amid the uncertainty the president has created, all the while knowing he is always one tweet away from creating even more chaos.
Made in Canada
Brian Scudamore, who holds the somewhat uncommon distinction of being an American-born founder of a Canadian success story, is not one to panic no matter what. The chief executive of O2E Brands Inc., the Vancouver-based holding company behind the 1-800-GOT-JUNK, WOW 1 Day Painting and Shack Shine franchises, has lived the American Dream, only with a Canadian twist.
His earliest, entrepreneur-stirring memories were seeded at his grandparents’ army surplus store in San Francisco. The place was piled high with foam mattresses, a wall of bomber jackets and an old-fashioned cash register with big buttons, as well as a valuable lesson Scudamore absorbed by watching his grandparents work the floor: you have to know how to talk to people to get ahead.
His mother eventually married a Canadian doctor and young Brian moved to Vancouver, which is where the middle-aged Scudamore still lives. At some point in his early 20s, he formally became a Canadian citizen, although he said he felt Canadian long before he did the paperwork. It was around this time that he saw a future career path after spotting a guy at a McDonald’s drive-thru in a pickup truck filled with junk.
“The American Dream was always in my brain as something that mattered to me, having been inspired by my grandparents in San Francisco,” he said. “I can’t help but identify with that American startup mentality of being gung-ho, being high energy and believing that I can do anything, having lived that dream of starting my own business, but I am still a Canadian.”
In Canada, he moved around as a kid, and always being the new kid in class meant making new friends and not being shy. He also happened to be the kid who couldn’t sit still. Hustling was simply part of his American-born, Canadian-raised DNA when he started his business later on.
But he understands that being a Canadian entrepreneur means you probably need to expand beyond the border in order to maximize market scale. At the current count, nearly 90 per cent of O2E Brand’s franchisees are in the U.S. To truly make it big, he had to make it in America.
Among the unwritten rules of working with his U.S. franchisees is to avoid any mention of politics. At a time when people are worried about paying their bills and recession fears are in the air, Scudamore’s advice to his owners is to focus on the things they can control: get out there, knock on some doors, recruit good people and don’t pull back on marketing because people will always need to get rid of their junk even if the market retreats.
On one late April morning in Vancouver, he had just arrived home from an annual gathering of CEOs at the Massachusetts Institute of Technology the previous day, where most of the attendees were Americans hailing from all corners of the economy — health care, real estate, technology and more.
Scudamore and the group went for a walk through the campus and the nearby streets. As both a talker and a good listener, he asks a lot of questions, and what he wanted to know was how his American friends imagined things playing out under Trump.
“There was 100 per cent consensus — believe it or not — on this one idea and it was, ‘I have no idea what’s going to happen,’” he said. “I’m not trying to be funny or anything, but I would ask that one question, ‘How does this whole thing play out?’ And everybody, the smartest people I know, all said, ‘I have no idea.’”
Trumping Trump
What is clear to Canadian immigration lawyer Benjamin Green, who specializes in workforce planning, employee transfers and navigating the U.S. and its labour market , is that Trump is keeping him busy.
His office has been getting calls from individuals with family connections to Canada who are looking to explore their options. Then there are high-net-worth, non-Canadian families who, either in the present or in past generations, have faced persecution in their country of origin and are gazing around an American landscape in which Trump is looking to end birthright citizenship. As a result, they’re thinking a move north might not be such a bad idea.
LGBTQ2S+ families are likewise experiencing unease, though where Canada could really score big in terms of bringing talented folks north is among the techie and research crowd.
Young geniuses, who once came from abroad to study at U.S. universities and are now newly graduated and employed by an American company, understand the clock is winding down on their post-grad work permit and know they are out when it reaches zero.
“In the United States, you run out of time,” Green said. “And that’s one place where Canada already does a really good job, actually, of getting these talented kids, who have gone to university in the United States and have worked for U.S.-based companies for a couple of years, to come here.”
Nanji at Ivey points to health care as one area desperately in need of recruits. Canada is about 23,000 family physicians short of being able to meet the country’s needs, according to a Health Canada study in 2025.
On the other side of the border, American family doctors annually earn about US$239,000 on average, which is about $330,000, or about $100,000 more than the median salary of a general practitioner here, according to Canadian government wage statistics.
In other words, leaving the U.S. means being willing to take a hefty pay cut, but Nanji said the government could create a program of incentives that might, for example, pay for a doctor’s relocation costs, guarantee them annual trips back to the U.S. and perhaps even look at finessing tax policies to mitigate the financial blow.
Opportunities to poach American talent and bring home Canadian expats and all-stars from a wide range of sectors don’t arise every day — if ever — but Trump, with his cuts to research funding and regressive social policies, has emerged as a legitimate reason to leave.
“Canada needs to take a stab at this unique opportunity, because if we just sit idle and do nothing, it will be an opportunity lost,” Nanji said.
Back in New York, Billy Berg knows a thing or two about those talented tech kids since his company employs a lot of them. The business is already experiencing the impact of Trump’s ways, given its exposure to the tourism sector . People who are nervous about the economy travel less, and travelling to the U.S. is becoming increasingly undesirable for Canadians , which hurts the bottom line.
If there is a saving grace, he said it is that his company does not manufacture anything, so it isn’t hostage to external supply chains, which would be a “total nightmare.”
The business is approaching US$1 billion in revenues and employs more than 800 people, many of whom are software engineers from India. What happens with those employees — and where they decide to go next — once their work permits expire is already putting a strain on his ability to hire new people.
“It is not like these are cataclysmic impacts, but they are already being felt and we’re probably one of the luckier ones,” he said.
Away from the office, Berg has learned a few things about life with Trump back in the White House, and that includes knowing who to nix from the dinner party guest list.
“If anybody is pro-Trump in a social setting and you mix in alcohol, it’ll get ugly quickly, and it sometimes does,” he said. “You either learn that I’m not going to talk politics around that guy because I know where he stands, or else I don’t know where he stands and so I need to be careful.”
Berg’s youngest child has another year left of high school, so uprooting her now would be unthinkable. But once she exits the nest, the “tether” will be gone, and the conversations with his spouse around the possibility of leaving could take on a more urgent tone. What he does know for certain, he said, is that he would not have been able to achieve all that he has without New York.
He did not know it at the time, but moving to the city was his big break, and the energy of the place that was evident in the beginning is still there, as are the professional networks he has built and the friendships he has made.
Leaving that behind would not be easy, and neither would finding a comparable, intellectually stimulating, good-paying senior executive echelon position in Canada, or anywhere else for that matter. But the fact that Berg is even thinking about it represents a significant shift in mindset.
“There is a reason I chose to stay and build a life here,” he said. “But it is funny, even though I am a dual citizen now, I don’t feel American.”
• Email: joconnor@postmedia.com
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