Ali Khan

I got some questions for Garry Tan & the team at Y Combinator. A few days ago, I learned that Y Combinator is no longer investing in Canadian startups. Canadian founders are now required to incorporate their company elsewhere to get a spot into YC. I’ve been building startups for over a decade. I understand the structural and investor advantages of incorporating outside Canada. That’s not the issue. What’s strange is the timing. This decision comes during a tense political moment between Canada and the U.S., and at a time when many of us are actively encouraging founders to build and stay in Canada. This move does the opposite in my opinion. It pushes more founders to relocate to the U.S., and many of them will never come back. Yes, the Canadian government has work to do in retaining top talent. But singling out Canadian incorporation, especially from an organization that claims to support founders globally just feels wrong. This isn’t just a brain drain. It’s a financial and economic drain. I’d really like to hear YC explain where this decision came from and why now. P.S. YC might not be supporting Canadian incorporated businesses but Boardy still is 😉

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Google Canada just announced a $13M AI Opportunity Fund to strengthen Canada's AI workforce. I'm genuinely excited about the potential social impact this will create for underserved communities. What stands out to me is how intentional this approach is - targeting Indigenous communities through the First Nations Technology Council, reaching high-unemployment areas via Skills for Change, and ensuring broad access through Toronto Public Library's city-wide initiative. A thoughtful way to democratize transformational technology. It's encouraging to see major tech companies recognize that inclusive AI development isn't just good social policy - it's essential for building a sustainable innovation ecosystem. https://lnkd.in/e_mKMiUA #AIforAll #AIforGood

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For episode 30 (!!) of #SeeingAroundCorners, Peyman and I recently had the pleasure of interviewing Zain Manji, Co-CEO and Co-Founder at Lazer Technologies, a Toronto-based engineering and design agency specializing in Shopify. Zain shared invaluable insights into the future of commerce, emphasizing the unification of web, retail, and international experiences. Lazer's unique approach, rooted in being "builders at heart" allows them to understand and address the pain points brands face. Having scaled their own multi-million dollar brand on Shopify, they bring a business-first perspective to their work with top brands like SKIMS, October's Very Own, Mattel, Inc., and AG1. We also delved into the role of AI in commerce. Zain highlighted two key applications enhancing the customer journey through chatbots and discovery tools, and boosting internal business efficiency with engineering tools like Copilot and Sidekick. It's all about strategically applying AI to solve the biggest pain points. This discussion is a must-watch for anyone looking to stay ahead in the dynamic world of e-commerce. #Ecommerce #Shopify #AI #RetailTech #DigitalCommerce #FutureOfCommerce #Innovation #BrandBuilding #Engineering #Design #podcast

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2025 was the worst year for Canadian VC funding since 2016. At the same time, 80% of our founders burn through early-stage capital rebuilding broken MVPs. Scope creep still kills half of all software projects. Non-tech founders get quoted $50k to $400k for the same application with no way to validate what's real. And when they do build? Half of the IP generated here gets assigned to foreign companies. We don't have an innovation problem. We have a translation problem. Brilliant ideas die in the gap between vision and technical execution because founders can't speak developer, and developers can't read minds. The concept-to-PRD process still costs $50k to $400k in senior engineering time. Most early-stage companies can't afford that, so they hire junior talent, get locked into vendors, or burn runway on throwaway code. The Vision-to-Execution gap isn't capital. It's the $400k scoping barrier that keeps ideas trapped inside founders' heads. Until we fix the process, more funding won't solve anything.

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Why doesn’t Canada produce more scaled tech companies? I asked 20 of Canada’s leading founders, investors, and ecosystem builders this question. Their responses were fascinating — and at times contradictory. Some argue we still have a startup creation problem. There simply aren’t enough early-stage founders taking bold swings. Too many play it safe because failure in Canada carries a permanent scar, not a learning badge. Without enough early experiments, we naturally have fewer companies that can “graduate” to scale-up stage. Others say it’s clearly a scale-up problem. Early-stage funding has improved, but growth capital and experience lag far behind. Canada’s pool of executives who have scaled a company from $10M to $100M is still thin — and that experience gap compounds over time. As one investor put it, “In the Valley, you can hire five people who’ve done it before; here, you might find one.” Capital density came up repeatedly. U.S. investors simply have more funds, deploy larger checks, and back riskier bets. A U.S. founder can raise $10M on an idea; a Canadian founder often needs traction before raising $1M. The math alone makes it harder for our companies to scale at the same speed. Several also pointed to ecosystem density and risk appetite. We lack the concentrated mix of capital, customers, and talent that accelerates growth. Corporate Canada and governments often admire innovation but hesitate to buy from it, forcing startups to seek U.S. customers just to validate at home. And then there’s the brain drain: many of our most ambitious founders still incorporate in Delaware and scale from the U.S., not from here. When success stories leave, the mentorship cycle weakens. I’d love to hear your view: what’s the real bottleneck — capital, culture, or something deeper? #CanadianTech #ScaleUp #InnovationEcosystem #VentureCapital #Entrepreneurship

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Shopify CEO Tobi Lütke made a bold policy change: teams must demonstrate why AI can’t perform a job before they’re permitted to ask for more headcount and resources. this will happen across industry soon... https://lnkd.in/gET7hzsY

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When I took over Google Canada, I thought I was doing the right thing by setting a big, audacious goal. I told the team: “We’re going to be a billion-dollar business in two years.” The math made sense. The market was there. But the team looked at me like I was out of touch — or worse, delusional. What I didn’t understand at the time is that people don’t get motivated by financial goals. They want to be part of something that matters. So we reframed the mission: We’re going to make the web work for Canadians. And our strategy was to be first or best at everything we did. That landed. Suddenly, people saw how their work fit into something bigger than a revenue target. There was a certain pride in place — in Canada’s unique role at Google. It wasn’t just a goal of hitting an arbitrary number — it became a goal about making an impact on people’s daily lives. That lesson has stayed with me. The teams that perform best aren’t just chasing KPIs. They’re chasing purpose: wanting to dedicate their days to work that really matters. If you’re a leader, ask yourself: Have you made the mission clear? Not just the “what,” but the “why”? Because if you haven’t, people will make up their own stories about what matters (or what doesn’t). And those stories won’t always align with where you’re trying to go.

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Y Combinator is no longer investing in Canadian startups. Canadian startups must now incorporate in the U.S., Cayman Islands, or Singapore to be eligible. Let that sink in. This is the same YC whose partners were in Toronto and Waterloo last September, meeting founders and sourcing talent. So what changed? This is not a ban on Canadian founders. You can still be funded, but the burden now increases to incorporate elsewhere. If you want access to the most influential early stage capital, Canada is no longer the default place to build from. Let’s be honest, most Canadian YC founders already incorporated in the U.S. to get in. But institutionalizing this preference on YC’s main eligibility page signals something deeper about where capital flows. As a Canadian, I feel, we need more pathways that let founders stay and scale here. Investing in Canadian startups shouldn’t require abandoning Canada. If you’re building here, scaling here, hiring here, your potential doesn’t diminish just because you are incorporated in Canada. Curious how other Canadian founders are reading this? Is this just reality… or a policy failure we’ve normalized? https://lnkd.in/dcuuth7J

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