Two Countries, One Stark Reality: Where Did Canada’s Entrepreneurial Fire Go?

Spend time with entrepreneurs on both sides of the border and the difference in energy is striking. Walk into a room of entrepreneurs in the U.S. and you feel it immediately. There’s a forward lean, an appetite, a buzz. People are talking about what they’re building and chasing, not what they’re waiting on. Risk is the price of admission.

Now walk into a comparable room in Canada.

I want to be careful here, because I love this country and I believe deeply in the talent we have. But I’d be doing you a disservice if I didn’t let you know what I’m observing. Too often, the energy is cautious, measured, almost tentative. The default setting is “wait and see” rather than “let’s go”. That gap worries me.

The Youth Problem

Here’s a number that stopped me cold: only 4% of wealthy Canadians are under the age of 40. In the United States, that figure is 24%. Six times more. Let that sit for a moment.

It’s not that Canada doesn’t produce self-made wealth. A BMO Harris Private Banking study found that roughly two-thirds of Canada’s affluent individuals are self-made, but we are building it slowly, cautiously, and late. The U.S. is minting young builders at a pace we simply aren’t matching. And it’s not a talent gap; it’s a structural one.

What’s Underrepresented at the Table

Take a look at the Business Council of Canada, 170+ of the country’s most influential business leaders. It’s a who’s-who of Canadian enterprise, filled with accomplished executives and stewards of remarkable institutions. But what’s underrepresented is the first-generation builder; someone who started with nothing and created something valuable. That archetype, the founder who bet everything on an idea, is far less visible in our national business conversation than they should be.

Compare that to equivalent rooms in the U.S., where founder-CEOs who began with a laptop and a credit card are the norm, not the exception. Canada produces them too: Tobi Lütke at Shopify, Chip Wilson at Lululemon, Garrett Camp co-founding Uber, but they remain outliers in our national story, and more often than not, their most audacious chapters were written from south of the border. Globally, 39% of Canadian billionaire wealth is inherited, above the world average of 33%. We are concentrating at the top rather than creating at the base.

The Tax Conversation We Keep Avoiding

David Rosenberg, one of Canada’s well-known economists, has been direct about this. Writing in The Globe and Mail, he called for slashing top marginal tax rates across the board – personal, corporate, and capital gains. His logic is straightforward and hard to argue with. Reducing tax incentives for risk-taking means less risk-taking, and with it, less capital formation, less productivity, and fewer jobs.

Canada’s combined personal marginal tax rates push past 50% in most major provinces. Our capital gains treatment has been a political football, with Ottawa’s recent attempt to raise the inclusion rate triggering a backlash that forced a deferral. The message this sends to a founder betting their savings, their time, and their livelihood on an idea is not an encouraging one. If we want a culture of risk-taking and first-generation wealth creation, the structure has to facilitate it. Right now, it doesn’t.

This isn’t about politics; it’s about competitiveness. Incentives influence behaviour. When the upside narrows, risk-taking adjusts. The entrepreneurs I spend time with on both sides of the border – the builders, the ones grinding every day – they don’t talk politics. They talk about what they’re building, what’s in their control, and what’s in their way. Right now, in Canada, the structure is in their way.

The Urgency No One Wants to Say Out Loud

Here’s what keeps me up at night. The job market is changing faster than at any point in our lifetimes. AI is not a future disruption; it’s happening now, and it is going to fundamentally reshape what work looks like for the next generation of Canadians. Entire categories of employment that young people are training for today will not exist in the form they expect by the time they enter the workforce.

In that environment, entrepreneurship isn’t just an economic preference, it’s a survival strategy. If we don’t build a culture and structure that encourages young Canadians to create rather than simply compete for shrinking pools of traditional employment, we are setting up a generation to struggle in ways we can barely anticipate.

We don’t have the luxury of a slow, cautious, wait-and-see approach. Not anymore.

What We Need to Change

Canada has extraordinary assets, including talent, multiculturalism, natural resources, rule of law, and proximity to the largest market in the world. But assets don’t build companies. Culture and incentives do.

The conversation starts with meaningful tax reform, not tinkering, but genuine structural change that says unambiguously: Canada wants you to take the risk. It continues with regulatory modernization that treats founders as constituents rather than compliance problems. And it requires a cultural shift that celebrates the people who swing, fail, get back up, and swing again.

That’s what groups at PEO Leadership | Innovators Alliance exist to build, one conversation at a time.

Questions for Us as Leaders

Three questions worth sitting with:

1. Are we building businesses that can scale globally or simply operate locally?
2. Are we designing incentives inside our companies that reward ownership thinking?
3. If a 26-year-old founder were deciding where to build today, would they choose Canada?

The U.S. has never stopped believing you can start with nothing and create something extraordinary. It’s time Canada started believing it too. With the rapid rise of AI and the profound changes coming to the labour market, we can’t afford to wait.

— Leon Goren CEO, PEO Leadership | Innovators Alliance