Over the last few months, I’ve been writing a lot, and I hope you’ll subscribe to see what I’ve been working on.

People have always asked me how blogTO came to be. How it started, what it was like at different points along the way, and what the hardest decisions were. This Substack will be my attempt to answer all of that, or as much as I can recall.

They are my recollections, told from my point of view. They won’t be comprehensive. There are things I’ve forgotten, details I’ll likely get wrong, and stories that belong to other people that I’m not in a position to tell. But I’ll do my best.

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The blogTO story needs to be told. At its peak, blogTO generated more than 350 million page views annually and had more than 3 million social media followers. If you wanted to know what was happening in Toronto, you needed to read or follow blogTO. Despite all that, not enough has been written about how it was built and evolved. Most of what I share on Substack will be the first time the story has been told publicly.

There was no blueprint for what we were doing. Nobody had written a guide to building something like blogTO. We had to figure it out as we went along, through a lot of trial and error.

We were still in the early days of digital media. New tools and technologies kept arriving, including smartphones, apps and social media. Each one changed how people consumed and engaged with our content, as well as what they expected from us. We had to adapt and evolve constantly, often on the fly.

A lot of people worked incredibly hard to make it happen. Late nights, weekends, and years of grinding when there was no guarantee any of it would amount to much.

I sold blogTO to ZoomerMedia in 2022. Selling something you’ve built over nearly two decades means accepting that someone else will be responsible for its future and may make decisions very different from the ones you would have made. It’s been a year now since I left, and I’ve had enough time and distance to sit down and tell this story properly. If I don’t, I’m not sure anyone else will.

My Substack starts with a summer at CNN in New York, where an unpaid internship gave me my first real taste of the media industry. It then moves to San Francisco, where I arrived just in time to watch the dot-com bubble burst, and returns to Toronto for a failed side project called Navigate the Streets before arriving at blogTO itself.

Along the way, I’ll write about the evolution of the brand Freshdaily, the publications Midnight Poutine and Beyond Robson in Montreal and Vancouver, and our first acquisition. Each had its own story, its own team, and its own challenges.

I grew up in Brampton, Ontario. Our house was full of magazines and newspapers, and the CBC was always on the radio. I had a Toronto Star paper route as a kid, but I didn’t know anyone who actually worked in media. There was no obvious path from where I was to where I ended up.

In high school, I was good enough at math but bad enough at English that nobody would have predicted I’d end up founding something like blogTO.

I studied business at McGill University in Montreal. It was a great time to be in the city. Rents were cheap. Quebec was still debating whether to leave Canada. I wasn’t the most gifted student, but I was curious and worked hard.

Throughout my telling of the blogTO story, I will do my best to recognize the many talented people who made meaningful contributions over the years. These posts are as much a celebration of what they accomplished as they are a record of what happened. Building a digital media brand from nothing is hard. Most of our competitors didn’t make it. The fact that blogTO did is something worth recognizing.

I apologize in advance if your name isn’t mentioned. It’s not intentional. The full list of people who were part of this story would run well into the hundreds. Probably thousands.

I hope you enjoy these reflections as much as I’ve enjoyed writing them. I’ll be sharing a new one each week. Subscribe to get each new post as it comes out.

New stories will be released weekly over the coming months. Subscribe for free to get full access to the newsletter and publication archives.

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