I was out for dinner last night on Ossington (here in Toronto). Afterwards, my business partner Rick and I walked the street for a bit. It was a beautiful evening. Every restaurant had their doors and windows open. All of the patios were full, many with the kind of awnings that I love from Paris. And in between these patios were endless options for beautiful window shopping. So during our walk, we couldn't help but say to each other, "man, what an awesome street."

Our line of thinking then went here: How did this ~600-meter stretch of street between Queen and Dundas become one of the coolest retail streets in the city? As you might expect, it follows the typical urban trajectory. It was a seedy street with cheap(er) rents. Then the artists and creatives started moving in, along with OG dive bars like Sweaty Betty's. And then the city implemented a brief moratorium on bars and restaurants because things were getting a bit too fun.

I also think it's fair to call Ossington's rise as being a spillover from Queen Street West. As rents rose on Queen, Ossington became a natural outlet. It was in the right location, and it already had a commercially-oriented and fine-grained ground plane, meaning the buildings could be easily repurposed for galleries, bars, restaurants, and whatever else. This is also why the strip just dies north of Dundas — there are no more suitable buildings.

To show you just how entrenched this built form was and is, here are a few archival photos from the 1920s and 1940s:

Beyond this, there's nothing particularly special about Ossington as a street. It has a 20-meter width, which is typical of most of Toronto's central main streets, and it's filled with a bunch of 2 to 3 storey buildings. So another thing it does is make you wonder: How many more Ossington Avenues could Toronto have if only we created the right preconditions for new businesses and ideas to flourish?

Of course, not every street can be an Ossington. What I'm talking about is simply creating more walkable, mixed-use streets. That's a lot harder to do when you don't have the bones that Ossington had, and you have primarily large lots and/or residential uses. But that doesn't mean it's impossible. As Toronto works to intensify its major streets, it's crucial that we also consider what the ground plane might one day want to become.

More on this in future posts.

I was just reading about Simple Ventures. They are a Toronto-based venture builder that has raised $15 million to help create 25 high-growth companies headquartered in Canada by 2030. Some of their investors include TD Innovation Partners, Sun Life, Sobeys, and Harley Finkelstein (President of Shopify).

Now, I'm not a venture capital expert, but this seems to me like a relatively small amount. (They plan to raise another $5 million by the end of the year.) So I would encourage more institutions and rich people to step up with their wallets, because you have to applaud their mission:

“We are coming together to issue a call to action - bring Canadian talent home,” said Rachel Zimmer, exited founder and Co-Founder and CEO of Simple Ventures. “This funding will allow us to build great Canadian Headquartered companies. Now is a crucial time to join our mission to put fire in the Canadian engine.”

Canada still has 100,000 fewer entrepreneurs than it did 20 years ago, despite the population increasing by over 10 million during the same period. At the same time, nearly one-third of Canadian immigrant entrepreneurs move to the U.S., citing limited support for scaling businesses at home. Simple Ventures tackles this problem by sourcing new company ideas, validating them, and pairing them with Canadian leaders to co-create ventures.

There's absolutely no shortage of smart, ambitious, and entrepreneurial Canadians. Where we need to improve is in commercializing and scaling our ideas. And it's crucial we do this as quickly as possible because there are powerful compounding benefits to entrepreneurship.

When a new company scales, it creates jobs, wealth, and knowledge. These ingredients can, and usually are, used to start a growing subset of even bigger companies. Venture capitalist Fred Wilson once referred to this as The Darwinian Evolution of Startup Hubs.

If you study Silicon Valley, what you see is something that looks like a forest where trees grow tall, produce seeds that drop and start new trees, and eventually the older trees mature and stop growing or worse, die of disease and rot, but the new trees grow up even taller and stronger.

If you drill down a bit deeper, you see that the founders, investors and early employees generate a tremendous amount of wealth from these big successes. The later employees don't make as much wealth but they do learn a ton and make enough money that they don't need to work for someone else and so they strike out on their own and are often funded by the folks who made the big money in the prior startup. That's how the seed drops from the tree and starts a new tree growing. This continues on and on and on.

When you think of startups and entrepreneurship in this way, you start to see just how important it is for us to keep growing our forests, instead of chopping down our trees and shipping them to the US. This is an exercise in city and nation building. And so I wish the team at Simple Ventures nothing but success.

LFG, Canada. If you're working on something and would like to pitch SV, click here.

I was out for dinner last night on Ossington (here in Toronto). Afterwards, my business partner Rick and I walked the street for a bit. It was a beautiful evening. Every restaurant had their doors and windows open. All of the patios were full, many with the kind of awnings that I love from Paris. And in between these patios were endless options for beautiful window shopping. So during our walk, we couldn't help but say to each other, "man, what an awesome street."

Our line of thinking then went here: How did this ~600-meter stretch of street between Queen and Dundas become one of the coolest retail streets in the city? As you might expect, it follows the typical urban trajectory. It was a seedy street with cheap(er) rents. Then the artists and creatives started moving in, along with OG dive bars like Sweaty Betty's. And then the city implemented a brief moratorium on bars and restaurants because things were getting a bit too fun.

I also think it's fair to call Ossington's rise as being a spillover from Queen Street West. As rents rose on Queen, Ossington became a natural outlet. It was in the right location, and it already had a commercially-oriented and fine-grained ground plane, meaning the buildings could be easily repurposed for galleries, bars, restaurants, and whatever else. This is also why the strip just dies north of Dundas — there are no more suitable buildings.

To show you just how entrenched this built form was and is, here are a few archival photos from the 1920s and 1940s:

Beyond this, there's nothing particularly special about Ossington as a street. It has a 20-meter width, which is typical of most of Toronto's central main streets, and it's filled with a bunch of 2 to 3 storey buildings. So another thing it does is make you wonder: How many more Ossington Avenues could Toronto have if only we created the right preconditions for new businesses and ideas to flourish?

Of course, not every street can be an Ossington. What I'm talking about is simply creating more walkable, mixed-use streets. That's a lot harder to do when you don't have the bones that Ossington had, and you have primarily large lots and/or residential uses. But that doesn't mean it's impossible. As Toronto works to intensify its major streets, it's crucial that we also consider what the ground plane might one day want to become.

More on this in future posts.

I was just reading about Simple Ventures. They are a Toronto-based venture builder that has raised $15 million to help create 25 high-growth companies headquartered in Canada by 2030. Some of their investors include TD Innovation Partners, Sun Life, Sobeys, and Harley Finkelstein (President of Shopify).

Now, I'm not a venture capital expert, but this seems to me like a relatively small amount. (They plan to raise another $5 million by the end of the year.) So I would encourage more institutions and rich people to step up with their wallets, because you have to applaud their mission:

“We are coming together to issue a call to action - bring Canadian talent home,” said Rachel Zimmer, exited founder and Co-Founder and CEO of Simple Ventures. “This funding will allow us to build great Canadian Headquartered companies. Now is a crucial time to join our mission to put fire in the Canadian engine.”

Canada still has 100,000 fewer entrepreneurs than it did 20 years ago, despite the population increasing by over 10 million during the same period. At the same time, nearly one-third of Canadian immigrant entrepreneurs move to the U.S., citing limited support for scaling businesses at home. Simple Ventures tackles this problem by sourcing new company ideas, validating them, and pairing them with Canadian leaders to co-create ventures.

There's absolutely no shortage of smart, ambitious, and entrepreneurial Canadians. Where we need to improve is in commercializing and scaling our ideas. And it's crucial we do this as quickly as possible because there are powerful compounding benefits to entrepreneurship.

When a new company scales, it creates jobs, wealth, and knowledge. These ingredients can, and usually are, used to start a growing subset of even bigger companies. Venture capitalist Fred Wilson once referred to this as The Darwinian Evolution of Startup Hubs.

If you study Silicon Valley, what you see is something that looks like a forest where trees grow tall, produce seeds that drop and start new trees, and eventually the older trees mature and stop growing or worse, die of disease and rot, but the new trees grow up even taller and stronger.

If you drill down a bit deeper, you see that the founders, investors and early employees generate a tremendous amount of wealth from these big successes. The later employees don't make as much wealth but they do learn a ton and make enough money that they don't need to work for someone else and so they strike out on their own and are often funded by the folks who made the big money in the prior startup. That's how the seed drops from the tree and starts a new tree growing. This continues on and on and on.

When you think of startups and entrepreneurship in this way, you start to see just how important it is for us to keep growing our forests, instead of chopping down our trees and shipping them to the US. This is an exercise in city and nation building. And so I wish the team at Simple Ventures nothing but success.

LFG, Canada. If you're working on something and would like to pitch SV, click here.