Yesterday it was announced (here, here, and here) that Toronto-based Top Hat has raised $22.5 million (USD) in Series-C funding. The round was led by New York-based Union Square Ventures.

I am always excited to see Toronto-based startups doing well and I am particularly excited by this remark in USV’s blog announcement:

“Also worth noting is that Toronto continues to impress us with its quality and diversity of companies. We now have five investments there, placing Toronto third as a location in the USV portfolio after New York and San Francisco.”

Here is another quote from Fred Wilson’s blog:

“Toronto is a great place for startups. In addition to five investments of ours that are HQ’d there, I know of at least one other USV portfolio company that has much of their engineering team in Toronto. The talent, mindset, and quality of the people in the Toronto/Waterloo tech/startup community is really top notch and we love investing there.”

Go Toronto. 

(Of course, Toronto really means Toronto-Waterloo. That’s the geography of the ecosystem.)

When I was 18 years old, I moved from the suburbs of Toronto to Waterloo, Ontario, which is about an hour west of the city.

I largely did this for two reasons.

Firstly, I had started visiting friends at both Wilfrid Laurier University and the University of Waterloo while I was in high school, and I thought that I wanted that kind of University town experience.

Secondly, I started University as a Computer Science student and I figured that Waterloo was a pretty good place to study that. Research In Motion (later renamed to Blackberry) was an important company at the time and interesting things were happening.

Though to be clear, I was a student at Laurier and not at the University of Waterloo – the better of the two schools for Computer Science – because I didn’t have the grades for the latter.

But a funny thing ended up happening. I hated living in Waterloo. I felt so out of place. So much so that I spent every weekend back in Toronto visiting my friends who had instead decided to go to the University of Toronto.

And I remember vividly how I felt during those weekends. I would stand in my friend’s apartments – most of which had dens and solariums that were hacked into bedrooms so that they could afford to live there – and I would look across the skyline and think to myself: why the hell do I not live here?

So I transferred to the University of Toronto. And that solved that.

The reason I bring up this story today is that I was reminded of it while reading a recent CityLab article by Richard Florida called, The Self-Confident City.

The three main arguments in the article are:

(1) Where we choose to live has a massive impact on our life outcomes.

(2) Self-confident people – according to a recent study – seem to be drawn to big cities.

(3) Self-confidence can also be a self-fulfilling prophecy for people in big cities.

Now, I don’t know if it was really self-confidence and youthful hubris that told me I needed to live in a bigger city than Waterloo. (It was probably part of it.) All I know is that I wanted to live in a super dynamic place that felt bigger than me. I wanted to feel like I was a small fish in a big pond trying to make some sort of meaningful dent.

That was true for me when I was 18. And it remains true for me today at 32.

Yesterday it was announced (here, here, and here) that Toronto-based Top Hat has raised $22.5 million (USD) in Series-C funding. The round was led by New York-based Union Square Ventures.

I am always excited to see Toronto-based startups doing well and I am particularly excited by this remark in USV’s blog announcement:

“Also worth noting is that Toronto continues to impress us with its quality and diversity of companies. We now have five investments there, placing Toronto third as a location in the USV portfolio after New York and San Francisco.”

Here is another quote from Fred Wilson’s blog:

“Toronto is a great place for startups. In addition to five investments of ours that are HQ’d there, I know of at least one other USV portfolio company that has much of their engineering team in Toronto. The talent, mindset, and quality of the people in the Toronto/Waterloo tech/startup community is really top notch and we love investing there.”

Go Toronto. 

(Of course, Toronto really means Toronto-Waterloo. That’s the geography of the ecosystem.)

When I was 18 years old, I moved from the suburbs of Toronto to Waterloo, Ontario, which is about an hour west of the city.

I largely did this for two reasons.

Firstly, I had started visiting friends at both Wilfrid Laurier University and the University of Waterloo while I was in high school, and I thought that I wanted that kind of University town experience.

Secondly, I started University as a Computer Science student and I figured that Waterloo was a pretty good place to study that. Research In Motion (later renamed to Blackberry) was an important company at the time and interesting things were happening.

Though to be clear, I was a student at Laurier and not at the University of Waterloo – the better of the two schools for Computer Science – because I didn’t have the grades for the latter.

But a funny thing ended up happening. I hated living in Waterloo. I felt so out of place. So much so that I spent every weekend back in Toronto visiting my friends who had instead decided to go to the University of Toronto.

And I remember vividly how I felt during those weekends. I would stand in my friend’s apartments – most of which had dens and solariums that were hacked into bedrooms so that they could afford to live there – and I would look across the skyline and think to myself: why the hell do I not live here?

So I transferred to the University of Toronto. And that solved that.

The reason I bring up this story today is that I was reminded of it while reading a recent CityLab article by Richard Florida called, The Self-Confident City.

The three main arguments in the article are:

(1) Where we choose to live has a massive impact on our life outcomes.

(2) Self-confident people – according to a recent study – seem to be drawn to big cities.

(3) Self-confidence can also be a self-fulfilling prophecy for people in big cities.

Now, I don’t know if it was really self-confidence and youthful hubris that told me I needed to live in a bigger city than Waterloo. (It was probably part of it.) All I know is that I wanted to live in a super dynamic place that felt bigger than me. I wanted to feel like I was a small fish in a big pond trying to make some sort of meaningful dent.

That was true for me when I was 18. And it remains true for me today at 32.