Two cities building the future. Not quite the same future.
When I visited SF, I expected to feel the energy everyone talks about. What I didn’t expect was how constant it was. Tech and startups were just the background noise everywhere - coffee shops, parks, wherever. Nobody was making a thing of it. That was just the conversation.
Toronto isn’t like that. And I’ve been trying to figure out whether that’s a problem.
There’s a version of this observation that turns into a complaint - not enough capital, not enough ambition, founders who think too small. I’ve heard it plenty. Some of it is fair. The funding gap is real, rounds are smaller, the pool of investors is narrower. Canadian founders often have to justify themselves more carefully and wait longer for things that would move faster elsewhere.
But sitting across from founders here over a few years, I’ve noticed something the complaint usually misses. The constraint shapes the work.
There’s also something quietly useful about not being inside the echo chamber. In SF, the proximity to capital and other founders creates a kind of ambient pressure to look and sound like the thing investors are currently pattern-matching on. The decks start to converge. The narratives rhyme. Everyone is running a slightly different version of the same playbook because that’s what the room rewards. Toronto founders aren’t immune to this, but there’s a bit more distance from it. Enough to occasionally do something that doesn’t look like anything else.
What Toronto hasn’t figured out yet is failure. In the Valley, a startup that didn’t work is mostly a data point. You tried something, you learned, you’re more useful the next time. Here it still carries more weight than it should. That makes founders more conservative than the moment calls for - slower to hire, slower to commit, slower to go after something that feels like a real swing. The ecosystem is better than it was, but this part is still catching up.
I don’t think Toronto needs to become SF. What I do think is that the founders here are better than the reputation, and the reputation is mostly set by people who haven’t actually paid attention.