🇨🇦 Canada · 🇸🇬 Singapore
By Priya Mehta, The Global Office
Canada is ranked the fourth-best startup ecosystem in the world, a fact its startup community finds simultaneously gratifying and infuriating — because the country is quietly losing its best founders to the United States while domestic investors wait for those founders to succeed before committing capital. Singapore, meanwhile, has no domestic market of note — a city-state of six million people — and has responded to this constraint by building one of the most aggressively supportive entrepreneurial environments on earth, driven partly by government strategy, partly by cultural terror of falling behind, and partly by a concept called kiasu that makes even a successful company feel like it is perpetually one product cycle from irrelevance.
Canada's startup reputation is built on genuine strengths: world-class universities producing AI and biotech research, significant immigration of skilled technical talent, a legal and regulatory environment that is coherent by global standards, and a cost base that was, until recently, competitive with American cities. Toronto-Waterloo has produced legitimate global technology companies. The ecosystem exists.
The critique, which is also well-established, is that it exists somewhat despite the culture surrounding it. Canadian investors are, by the assessment of their own industry, disproportionately risk-averse — waiting for proof of traction that their American counterparts would provide funding to generate. Early-stage funding has been declining relative to the US, with Canada's three leading startup cities pulling in less than 5% of the venture capital that flows to their American equivalents. In 2024, only 32.4% of startups founded by Canadians that raised more than $1 million were actually based in Canada, down from over 67% between 2015 and 2019. The inevitable result is that founders who want to build at scale leave: TD Economics has documented a persistent "silent brain drain" in which Canada-educated talent exits for San Francisco, New York, and increasingly, Singapore. Y Combinator quietly dropped Canada from the list of countries in which it invests, a development that the Canadian startup community discussed in tones ranging from indignation to resignation.
The cultural dimension is harder to quantify but widely discussed. Canada scores 48 on Hofstede's Uncertainty Avoidance — moderate, suggesting reasonable tolerance for risk in the abstract. But the gravitational pull of stable, well-compensated corporate employment — in banks, in government, in large resource companies — remains very strong, particularly as the cost of living in Toronto and Vancouver has risen to levels that make financial survival without a stable salary a more acute calculation. A generation of Canadian graduates that might, in a different cost environment, have taken startup risk tends to look at downtown Toronto rents and select a Bay Street salary instead.
Singapore's relationship with risk is shaped by the existential logic of its geography. A city-state without natural resources, surrounded by larger neighbours, that achieved one of the world's highest living standards through manufacturing, trade, and financial services is not inclined toward complacency. Kiasu — the Hokkien term for "fear of losing" — is simultaneously a cultural self-critique and a description of how Singapore's economy actually works. It is the fear of being left behind translated into a national competitive posture.
The government has been an unusually active ecosystem architect. Singapore hosts over 4,500 technology startups, 220+ incubators and accelerators, and more than 500 venture capital firms. Enterprise Singapore runs grant programs, co-investment schemes, and international market development programs that function as a government-subsidized risk buffer for early-stage companies. The 2025 Global Startup Ecosystem rankings placed Singapore in the top five globally, with first-place rankings in financial services and among the world's top two in fintech. Singapore also scores only 8 on Hofstede's Uncertainty Avoidance — among the lowest in the world — suggesting an actual appetite for ambiguity that matches the startup environment.
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The tradeoff is visible in the workforce data. Singapore's average workweek runs to 45 hours, with 23% of workers regularly exceeding 48. Gallup's 2025 State of the Workplace report ranks Singapore second-lowest for employee engagement in Southeast Asia, and surveys find 61–73% of Singaporean employees reporting burnout or active unhappiness. About 50% work up to ten hours of unpaid overtime per week. The meritocratic ideal — that performance is rewarded and results matter more than seniority — produces motivation but also acute performance anxiety. The same kiasu mindset that drives founders to build global companies from a standing start also drives employees to answer emails at midnight and treat a lateral move as personal failure. Hierarchy persists even in startups; face-saving indirect communication defines meetings; and the stated ambition to improve work-life balance has not yet resolved the tension with the underlying culture that makes 6 p.m. departures feel like a political act.
Both countries are grappling with the same fundamental tension: the corporate path is safer, better compensated in the short term, and increasingly incompatible with the ambitions of economies that want to compete in technology and innovation. Canada has more natural talent than it can retain. Singapore has more institutional support than any comparable jurisdiction and a burnout rate that suggests the support is not painless.
The optimal answer — which several founders in both countries have arrived at independently — is probably to incorporate in Singapore, raise money in Singapore, and live in Canada. This has not been empirically tested at scale, and it does require two sets of accountants, but it speaks to something real: neither country, taken alone, provides the full package. One gives you the ecosystem. The other gives you enough sleep to use it.
Quora — On whether Singapore startup culture is genuinely embraced by NUS and NTU graduates: "Conservatively, 50% of grad startups are 'me too' products. There is a general aversion towards supporting entrepreneurship, especially in the high-tech sector. The grade-driven culture at NUS is not conducive to risk-taking." — Quora respondent, 'Is it really true that startup culture in Singapore is thriving and is embraced by local grads?'
Hacker News — On Canadian startup dynamics: "Canada is a country filled with risk-averse people. Canadian VCs drag out the process, emphasize the ways a company will fail, and wait until the company is obviously successful before committing. One in four STEM graduates from U of T, Waterloo, and UBC work outside Canada. Software engineering leads at 66% working abroad." — HN thread on Canadian brain drain
Expat Life Singapore — On navigating the Singapore workplace as a foreign professional: "Due to the emphasis on harmony, communication can be indirect. A non-committal response might signal disagreement, while a lack of questions in a meeting could indicate confusion rather than consensus. Physical contact is kept to a minimum. Learning to read what is left unsaid is not optional — it is the job." — expatlifesingapore.com, September 2025
Reddit r/canada — On the startup-versus-corporate pull: "Great opportunities are available south of the border and the story hasn't changed since 2018. With Toronto rents where they are, the runway calculation just doesn't work for most people. Bay Street doesn't feel like selling out anymore — it feels like survival." — r/canada discussion on tech brain drain
Quora — On choosing between Canada and Singapore to incorporate: "Singapore is a magnet for talent, business-friendly, and a paradise for growth. The main disadvantage for foreigners is that you won't benefit from government co-investment schemes unless you have a Singaporean co-founder. Which is fine — until it isn't." — Quora, 'Between Switzerland, Australia, Canada, and Singapore, which is the best place to create a startup?'
Canada has the talent and loses it. Singapore has the infrastructure and extracts a toll for using it. If you want to build a company that might become significant, Singapore offers a more aggressive support system, a more globally connected market, and a culture that treats entrepreneurship as the sensible choice rather than the eccentric one. If you want to build a company while maintaining something resembling a functioning personal life, Canada — with its imperfections and polite risk aversion — may be the more humane operating environment.
The uncomfortable truth is that "best place to start a company" and "best place to live while starting a company" are two different questions that, for most founders, eventually collapse into one. Canada keeps asking you to wait. Singapore keeps asking you to sprint. The founders who thrive in either place are the ones who figured out, early, which question they were actually answering.
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Priya Mehta
Staff writer covering financial markets and corporate strategy. Has strong opinions about spreadsheets.