You should be more interesting.
Above all else, that’s what Montreal tells us. Toronto, by contrast, says we should be more important, and Vancouver that we should live better.
In his 2008 essay, Cities and Ambition, Paul Graham describes New York as a place that tells you to be richer, Cambridge smarter and Silicon Valley more powerful. By power, he means the ability to affect the world, which is why he points to Google: its founders commanded respect for the company’s influence, beyond the wealth that came with it.
At one point in his essay, Graham mentions a friend who moved to Silicon Valley and complained about the quality of the eavesdropping. I laughed, remembering a conversation I overheard at Saint Frank on Folsom Street in San Francisco. Two people beside me were talking passionately about the cost of AI inference, and I honestly couldn’t tell whether they were on a date or one was pitching the other a business idea. Maybe it was both.
Whatever it was, I’m rooting for them.
While AI would be my first guess for the conversation at the next table in San Francisco these days, I never knew where a conversation would go when I was at university in Montreal. I met people with such different interests, and loved how many ways there were to be someone you’d want to get to know. Perhaps what we had in common was an interest in what made each other different.
Toronto, meanwhile, expects the world to pay attention. On September 14 and 15, global investors will be at its doorstep for the Canada Investment Summit. I like that confidence, and the expectation that Toronto should be a place the world comes to do business.
Vancouver likes to remind you how out of shape you are. “You really should be going for that 5 a.m. run,” it seems to say. I’ve only visited a handful of times, but knowing I could ski in the morning and paddleboard in the afternoon makes me less inclined to brag about my Saturday triathlon: coffee, a breakfast burrito and a sweet treat.
These are my impressions as a proud Canadian who has spent time in Toronto and Montreal and now lives in Silicon Valley. You may hear something different. And no, Edmonton, Winnipeg, St. John’s and everywhere else, I haven’t forgotten about you.
Imagine telling people across Canada to “be more ambitious.” Okay, sure. About what? Each person could take the request seriously and, depending on where they live, have something quite different in mind.
The ambitions we associate with a given city reflect its culture, including what its residents admire and what they’re willing to support. If the approval of our friends or colleagues holds weight, which it often does, we have strong reason to pursue work they admire. Even when we have the resolve to go against the grain, it helps to have a few people who take our work seriously and celebrate our success.
In turn, the work we attempt gives our friends and colleagues examples of what they might try, while the help we offer shows which efforts we think deserve encouragement.
I suspect we underestimate our ability to shape culture because we encounter it after other people have done so much of the shaping. To me, exercising agency means taking responsibility for something we want to happen and acting on the part we can influence.
If a place matters to you, what would you like to help make possible there?
Canada’s trade dispute with the United States has given questions about our economic future a new urgency, with new counter-tariffs effective today, September 8. I’ve been encouraged by the people putting their energy into what Canada can build, and I want that effort to last well beyond this moment.
My own interest is in technology and entrepreneurship. I want more Canadians helping decide which technologies get built and how people use them. Just as importantly, I want the companies behind those technologies to grow from Canada, creating good jobs here as they reach customers around the world.
Graham argues that economic power can produce wealth, and puts ideas “one step upstream from economic power.” It’s one reason I’m encouraged by Canada’s effort to attract leading researchers, even if some of the benefits take decades to emerge.
I often read calls for Canada to be more like Silicon Valley. Though I appreciate the ambition, there’s a fair bit of Canada to fit into one valley. Before deciding what we could recreate here, we need to understand how the Valley became a place where so many people wanted to build technology and helped each other do it.
At the beginning of the twentieth century, much of the Santa Clara Valley was covered in fruit orchards, and families and friends were introducing local children to radio. At eleven, Charles Litton had a small shed he called his “Wireless House.” He later attended a high school that offered a free education in mechanical trades, where he learned to work with materials and tools.
By the 1920s, a local radio club brought together farm boys, Stanford students, technicians and retired executives. Members competed to reach distant stations, so a clever transmitter could earn its maker a reputation among people who understood why it was clever. But after mastering a technique, members also showed others how to do it.
Litton and his radio friends William Eitel and Jack McCullough went on to work in local radio companies, which needed transmitting tubes to generate and amplify signals. RCA and its East Coast partners controlled key patents and refused to sell the components to certain manufacturers, so friends working at different companies helped each other develop alternative designs and manufacturing methods.
When Eitel and McCullough founded Eimac in 1934, local investors put up money while Litton helped his friends save on equipment by supplying plans and parts for their machinery.
Eimac’s early customers included radio amateurs, but by 1939 it was supplying tubes for Navy radar tests. As wartime demand grew, the company could serve a much larger market using skills it had developed making tubes for radio.
As the region grew, military research and funding were crucial, and Stanford connected students and researchers with local firms. Semiconductor companies also drew on skills developed in radio-tube manufacturing.
When a group of scientists and engineers wanted to leave William Shockley’s semiconductor laboratory in 1957, they initially hoped to find another employer who would hire them together. Investment banker Arthur Rock and a colleague suggested starting a company and helped secure the backing. The eight employees who left to establish Fairchild Semiconductor became known as the “Traitorous Eight.”
They went looking for a better boss and ended up becoming their own.
People kept leaving Fairchild to start companies—Intel among them—and some went on to finance new ventures, as Eugene Kleiner did at Kleiner Perkins and Don Valentine at Sequoia. So many businesses trace their origins to Fairchild that there’s an actual family tree.
By 1975, inexpensive microprocessors were allowing hobbyists to build their own computers, and the organizers of the Homebrew Computer Club invited enthusiasts to meet in a garage. At later meetings, members explained what they were making, what they needed and what they had to share, then gathered around card tables to exchange designs and advice.
In 1976, Steve Wozniak showed his Apple I at a club meeting. Fellow member Len Shustek recalls that engineers admired its design, though few could have predicted that this machine, rather than the one on the next table, would become the basis of a major company.
The club’s organizers didn’t have to know which project would become a business to give people somewhere to show their work and ask for help.
So what does this all suggest for Canada?
Before deciding how to contribute, I’d look at the work already happening in our cities. The opportunities will look different in Montreal, Toronto or Vancouver because each city has its own mix of institutions, businesses and interests.
In Montreal, Mila’s internship and job fair led to a placement at the music company LANDR, where a student developed tools to detect streaming fraud. The company’s team could keep using the tools after the internship ended.
In Waterloo, student volunteers built Socratica, a community where people work on projects ranging from engineering to art and poetry, then show each other what they’ve made. To develop a shared workspace, the group partnered with Velocity, the University of Waterloo’s entrepreneurship program.
What work in your city would you like to be part of? If you find a group already doing it, ask how to get involved and where they need help. You can also invite a few people with overlapping interests to get together and talk about their work, especially if they don’t yet know one another. The whole city needn’t share your interest, and the people you invite don’t all have to live there.
At C100, I serve on a dedicated board led by co-chairs Michael Garrity and Mike Wessinger. We believe some of the tech companies that shape the world in the decades ahead will start, scale and win from Canada.
Our Fellows and Growth programs connect founders building companies in Canada with experienced operators and fellow founders, including those in Silicon Valley, for advice and introductions.
We’re looking for sponsors and funding partners to help us offer these programs to more founders. If you work in government or represent an organisation that shares this ambition, get in touch.
If you have experience to offer founders, talk to us about becoming a trusted advisor.
Not Sorry exists because I want to know more people who care about Canada’s future and want a hand in charting its course. I don’t yet know what we’ll do together, but I figure I can help us find each other.
If Not Sorry were a city, I’d want its message to be: you should exercise more agency.
If you’d like to join me, subscribe and invite someone you’d like to have in the conversation.
What might we accomplish together?