I’m late in writing this blog post because I was up in Collingwood for the day snowboarding. I’m exhausted, but I do have something to say.

One of the things I always find interesting when I’m driving north of the city is how far Toronto’s major north-south streets extend. Go out to Aurora or Newmarket and you’ll still come across many familiar faces such as Jane, Keele, Dufferin, Bathurst and Yonge Street. And the distance between each of them is exactly the same as it is in the city: 2 kilometres.

This may not seem like much of a big deal, but have you ever wondered how this street grid was established?

These streets are actually concession roads. And they were used to subdivide undeveloped land in Upper and Lower Canada into a grid that could then be further subdivided into farming lots. Each square of the grid is 2 km x 2 km, or 1,000 acres.

Look at a map of the Greater Toronto Area and you’ll see it:

But what I find most intriguing about this grid system is that it was designed around farming—not our current use case. The intent was to further subdivide each 1,000 acre lot into smaller 100 acre farming lots. And these concession roads were for access—they weren’t city blocks.

By comparison, there’s another city that’s famously run off a regular street grid. You may have heard of it. It’s called New York. And its street grid was established in the Commissioner’s Plan of 1811. Some even go so far as to say that it’s “the single most important document in New York’s development." 

But New York’s grid is much different than the one I’m talking about. Because of its smaller scale (20 blocks a mile going north-south), New York’s was decidedly urban. It was meant for city building.

Now, in the case of Toronto, concession roads obviously never stopped us from developing a thriving city. We filled in each square to make them as urban as we needed them to be. But as planning ideals changed, so did the infilling of those squares. Our grid was flexible enough to accommodate everything from farm land to suburban subdivisions.

But I can’t help but wonder how the Greater Toronto Area would have turned out had we, quite simply, chosen a different size of square. What if instead of 2 km x 2 km, we had made them 1 km x 1 km? Or what if we made them even smaller? What would the Toronto region look like today?

Sometimes it may seem like a simple decision, but in reality the implications are huge.

A friend of mine posted this article on my Facebook wall yesterday: “A Snowier Silicon Valley in BlackBerry’s Backyard.”

It essentially talks about the fact that despite the rapid decline of BlackBerry (it just reported $4.4 billion in losses), the Kitchener-Waterloo region is thriving. Many companies—both local and international, such as Google and Motorola, Square, Desire2Learn, Kik and others—have all hung their shingle in the area. 

Part of this certainly has to do with the University of Waterloo, but much of it also has to do with the legacy of BlackBerry. In fact, you could argue that BlackBerry (formerly Research in Motion) is what started at all.

In reading the New York Times article I was reminded of a post that Fred Wilson wrote last year called, “The Darwinian Evolution of Startup Hubs." It’s a great post. In it he talks about how he looks for the company that gave birth to the hub. In Silicon Valley he argues that it was Fairchild Semiconductor and in New York it was Doubleclick.

Once started, he likens the hub to a growing forest. The big trees (mature companies) start dropping seeds and new trees then start to grow (more startup companies). This is important, because it kick-starts a non-linear cycle of entrepreneurial growth.

Here’s how he maps out Silicon Valley:

"In my mental model of Silicon Valley, the first "tree" was Fairchild Semiconductor (founded in 1957) which begat Intel (founded 1968) which begat Apple (1976) and Oracle (1977), which begat Sun (1982), Silicon Graphics (1981), and Cisco (1984) which begat Siebel (1993) and Netscape (1994), which begat Yahoo! (1995) and eBay (1995), which begat Google (1998) and PayPal (1998), which begat YouTube (2005), Facebook (2004), and LinkedIn (2003) which begat Twitter (2006) and Zynga (2007), which begat Square (2010), Dropbox (2008), and many more."

Using this logic, Fred Wilson argues that Silicon Valley is about 10 cycles in and New York is at about 2. So what about Kitchener-Waterloo? Well if you buy into the argument that BlackBerry is what started it all, we’re really only into our first cycle. BlackBerry created a lot of wealth and talent, and now it’s being deployed into local startups. Our forest has begun.

Part of me worries, though, if Kitchener-Waterloo is the right place for a startup hub over the long term. Sure it has the University of Waterloo, but does young talent want to be there? At about 320,000 people, it’s no San Francisco, New York or Toronto. And we’re already seeing a significant pull towards urban centers.

But let’s look at it from the perspective of Southern Ontario as a whole. We’re at a critical moment in our evolution. The mother tree has caught a disease and it’s starting to take its toll. It may be able to fight it off, but right now it’s not looking promising. Thankfully, there are many young trees sprouting up to replace it. But we’re going to need to take special care of them, because they’re probably our best shot at creating our own thriving forest.

Marketer Seth Godin just wrote a typically short blog post called, “Am I supposed to like this?”

In it he talks about the fact that we are, for example, more likely to enjoy the food at a fancy restaurant. And we’re also more likely to enjoy a bottle of wine if it’s expensive or if we believe it comes from some desirable wine region and it’s supposed to be good (you can even just switch the bottle).

He then sums up this idea in one line that I really like: "Judgments happen long before we think they do."

Now, I’ve thought about this same idea with respect to cities. Take New York, for example. New York is famous. If I had to pick a capital for the world, it would probably be New York.

You watch it in movies and shows (even if it’s actually filmed in Toronto, Chicago or some other stand in). We read about it. We hear about it. We generally form judgments without the actual experiences. That builds brand equity. We’re supposed to like New York. Sex and the City told us so. And that makes it all that much better when we eventually get there.

Of course, it’s a bit of a catch-22. You have to be an awesome city for people to want to make movies and songs about you. But in this era of global connectedness, I think everyone, from citizens to economic development agencies, can fake it until that city makes it by investing in “supposed to." Am I supposed to like this city?