The daily round-up of Toronto news links had been a mainstay of blogTO since the early years. It had a devoted readership, but it really only served a small, loyal segment of our audience. Page views had been flat for years. Its audience wasn’t growing. The broader readership wasn’t looking for curated summaries of news links from us. They were engaging with individual stories, often finding them first through search or on a social media feed.

The Morning Brew wasn’t built for search. It wasn’t conceived for the era when social shares played a critical role in content distribution. The data was clear. People didn’t share round-up posts the way they did individual articles, with clear, strong headlines. It also had very little shelf life. Whatever page views and engagement it received would come within the first 48 hours. After that, its long-term value to the site dropped to zero.

The Morning Brew readers let us know they weren’t happy with our decision. In its place, we dedicated more resources to breaking news. We had realized we could compete with legacy media on these stories because of the digital tools we used to quickly identify the most compelling ones, and because our social media reach was already larger than most of our competitors.

The decision was the right one. The analytics didn’t lie. The website kept growing. We were doubling our traffic every two years.

After we stopped publishing the Morning Brew, we noticed other Toronto websites copying the format. They must have figured our pivot was their opportunity. We weren’t surprised. This was a pattern we saw repeatedly over the years: we would try something, study the data, and if it wasn’t performing, we’d move on. Then we’d watch other publications copy the content we had just abandoned, only to eventually reach the same conclusion we had.

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The end of the Morning Brew was part of a much larger shift in how digital media worked during this era, and it had everything to do with Facebook.

In 2013, Facebook redesigned the News Feed. They were increasingly prioritizing content that generated engagement and shares. Within a short time, Facebook had become the single most important distribution channel for many digital publishers. It became the place where a growing number of Canadians discovered, shared and consumed news.

U.S. digital publishers like Buzzfeed and Upworthy had figured out how to exploit this new reality. They crafted headlines that sparked curiosity or elicited a strong emotional response. We studied what these publishers were doing and adopted tactics that made sense for us. We became more deliberate about how we wrote headlines, which images we selected, and how we packaged stories to perform in the News Feed.

We also invested in tools that gave us an edge.

Chartbeat was a real-time analytics platform built for digital publishers. It tracked how many readers were on the website at any given moment, which articles they were reading, where they had come from and how long they were staying. It could show us, second by second, whether a post was gaining momentum or falling flat. We always had it open in our browsers and soon mounted flat-screen TVs on the office wall so we could simply look up and see what was happening. If a post wasn’t performing well, we’d often go back in and change the headline or swap the lead image.

Google Trends was another critical tool, as it helped us understand what people were searching for. We used it constantly to plan content. Before writing a listicle, we’d check whether there was enough search interest in the topic to justify it. For breaking news, we’d see how people were actually searching for a developing story and then optimize our posts to match.

We also used Spike, a social media monitoring tool from NewsWhip. Spike tracked which stories were gaining traction across the web in real time by keyword, topic or geography. It also showed us how content from competitive publications was performing. We could see which content was resonating at publications like the Toronto Star and the CBC, and, equally important, what wasn’t, which helped us identify which stories to avoid. The tool was critical to our breaking news coverage, helping us decide what to cover and how to frame it.

Seasonal guides also became a bigger priority for us around this time. We would publish a set of guides on what to do in Toronto each spring, summer, fall and winter. The content was popular with readers, and advertisers loved it too, so they generally bought up all the ads next to the articles, which more than justified the extra time and resources it took to create.

Our listicle output had expanded well beyond the Best of Toronto posts we had become known for. The potential topics were practically endless. One of the fun listicles in 2014 was a series by Liora Ipsum that mapped the best cheap eats, coffee shops, bars, and restaurants in Toronto by TTC subway stop. For each post, we recreated the subway map, replacing the station names with the businesses we had selected for each stop.

Real estate was also emerging as a growing content area. Readers especially loved our House of the Week and Condo of the Week posts, where our team of writers, including Leslie Bank, Amy Michelle Smith, Isabel Ritchie, Alana Charles, and Meghan Jeffery, profiled interesting properties currently for sale in Toronto. The posts featured photos, details about the listing and the writer’s personal thoughts on the property.

In 2014, Bosley Real Estate signed on as the exclusive sponsor for what would become a five-year commitment. Some readers wondered whether Bosley was choosing the properties. They weren’t. We never discussed the posts with them. We kept a strict separation between editorial and advertising. At the bottom of each article, we included a disclosure noting that all editorial selection and writing was done by blogTO.

The sponsorship revenue more than covered the cost of the content. We put the surplus right back into our editorial operations, growing the real estate section, which would, in the years to come, become one of the website’s highest-traffic topics.

All the algorithm optimization in the world wouldn’t have mattered without writers who could produce content worth reading and sharing. While some of our staff writers now handled breaking news, the majority of the team continued to produce original content that distinguished blogTO from our competitors.

Ed Conroy was a cultural historian and archivist who had spent years collecting old VHS and Betamax tapes of Ontario television, digitizing recordings of commercials, public service announcements, local TV shows, and other material recorded in the 70s, 80s, and 90s. That personal archive, combined with his own memories of growing up in Toronto, gave him a well of material that he turned into posts unlike anything else we published.

One of his most popular pieces was a nostalgic look at how Scarborough was once home to the world's largest McDonald’s, a sprawling restaurant at the Toronto Zoo that operated from 1974 to 1990. His article on Adventure Playground, a free-form play space on Toronto’s waterfront where kids could build things with real tools and materials, captured something that could never exist today and triggered a flood of memories from readers who had been there as children. And his piece on the birth of late-night TV in Toronto, exploring a time when local broadcasters still signed off for the night, and the city didn’t have 24-hour television, was the kind of deep cut that drew directly from his archival work.

Ed’s nostalgia lists, like “30 signs you grew up in Toronto in the 1980s,” were also guaranteed to drive traffic thanks to the engagement they’d spark on Facebook. We would resurface Ed’s posts years later for a new generation of readers, and they would perform just as well. After his time with us, Ed wrote a book titled ImagiNation: The Golden Age of Toronto Kids’ TV and mounted an exhibit in Toronto on the same theme. His archives live on at his excellent website, Retrontario.

Martha Stortz brought a background in comedy and improv to the team. She was the kind of writer who would sign up for Toronto’s first mermaid school and come back with a piece that perfectly captured the absurdity of the experience. Martha covered nightlife, bars, parties and events with a voice that never took the subject too seriously. Reviewing the newly opened The Addisons Residence, she described trying a cocktail and going “from Grace Kelly to Gary Busey in the course of ten minutes,” and closed the piece by noting she was “personally grateful [the bar] exists because I legitimately don’t know anyone in real life with a house this nice that would invite me over.”

Some other notable team members during this period included staff writer Sarah Ratchford, who later became This Magazine’s Editor. Benjamin Boles was someone whose writing for Now Magazine I had long admired. When he started covering Toronto’s nightlife scene for us, it brought depth and authority we hadn’t had before. Josh Chong and Christina Cheung were valued members of our food team. And James C Lee helped cover retail stores as a member of our freelance photography team.

As was common throughout blogTO’s history, the competitive landscape kept shifting.

Narcity expanded to Toronto in 2014. It was from the same team behind MTL Blog, a Montreal website that had drawn criticism for its editorial practices. Their content didn’t impress us. A lot of it seemed to come from young writers who didn’t know the city very well, and factual errors were common. But they clearly understood how to package content for Facebook. Their posts were generating an impressive volume of engagement, particularly articles about things to do and day trips from Toronto, which were inherently shareable.

Zomato, the restaurant discovery platform originally based in India, also entered Toronto in 2014. The Toronto Star asked me what I thought about them. I said that Toronto was “spoiled for choice” when it came to restaurant apps, and that global platforms often struggled in local markets where they faced established competition like us. After the article went live, Zomato’s Canadian manager reached out to me to explore a partnership. I declined. Zomato would acquire Urbanspoon the following year, but never gained a strong foothold in Toronto. They shut down their Canadian operations in 2022.

In 2015, Buzzfeed arrived. They had been hinting at a Canadian expansion for months, and that June they officially opened a Toronto office in the same building where The Toronto Standard had set up shop years before. Craig Silverman, who had been the Editorial Director for short-lived OpenFile, was brought in to lead their team. BuzzFeed hired some talented staff and competed with us for ad buys from the big agencies, so I watched it closely.

Meanwhile, Torstar continued to demonstrate that it had its head in the sand when it came to digital, investing $33 million in Star Touch, a tablet app modelled on Montreal’s La Presse+. It was fundamentally flawed. In an era when Facebook was the dominant platform for discovering and sharing news, Star Touch was a closed ecosystem that lacked social sharing functionality. You couldn’t share a story from the app to Facebook or any other platform. It was a deeply misguided and expensive bet on a distribution model that ignored how people were actually consuming content. Star Touch was shut down in 2017.

While we were navigating all the competitive threats, we were also spending more time dealing with content theft.

Sites were taking our articles and republishing them without permission, and chasing them down felt like a never-ending game of whack-a-mole. We would send formal takedown requests or file complaints to have sites removed from search results, but within weeks, a new offender would inevitably appear.

The most brazen case involved yorkbbs.ca, which had been translating large volumes of our content into Mandarin and presenting it as original work. We likely never would have noticed if it weren’t for a reader who tipped us off. When we confronted the site’s operator, they tried to negotiate a licensing deal rather than take the content down. We said no.

Over the years, Yahoo, MSN, Vice and others had all approached us about licensing or syndication deals. My position was consistent: if people wanted blogTO content, they had to come to us directly.

Around the same time, the Huffington Post, which had been operating in Canada since 2011, plagiarized one of our articles. The irony was difficult to ignore. The article they copied was about Peace Collective, the Toronto brand behind “Toronto vs Everybody,” being accused of plagiarism by the designer who created “Detroit vs Everybody”. The editor of the Huffington Post never apologized but agreed to take down the article.

By 2015, annual revenue had reached $1.1 million, with expenses at about $850,000. It had taken us roughly a decade to breach the million mark, but we finally got there. For a small, independent digital publication competing with much larger, better-funded organizations, it felt like a meaningful milestone.

We were profitable and self-sustaining. We weren’t reliant on government grants or subsidies. Every dollar came from advertising, as well as a couple of modest new revenue streams we had been building.

One of these revenue streams came from a partnership with a Toronto-based company, Universe, which processed ticket sales for an increasing number of local events. We integrated Universe into our event listings, which gave us a small cut of each ticket sale we sent their way. It wasn’t a lot of money, but it also required very little effort on our part once we had set up the proper integration and tracking mechanisms.

We also started getting requests from international magazines, marketing and design agencies, and local businesses to license some of the original photos we had invested in to accompany our articles. It was an unexpected revenue source that grew over time. We split the licensing revenue in half with our photographers.

One thing that wasn’t generating any revenue for us was branded content. It was growing in popularity, and requests from advertisers and PR companies would only increase in the years to come. Suite 66 was fielding these requests all the time, but they knew my position on this.

No reader had ever asked for branded content. Selling it meant putting advertiser interests ahead of the audience we had spent years building into a readership that trusted and loved what we did. I was willing to forgo the revenue to protect the relationship we had with our community.

It cost us. Suite 66 did their best to redirect those conversations to other ad formats, and they sometimes succeeded. But, usually, we lost the business. When an advertiser only wanted branded content, they would turn to competitors like Narcity or Toronto Life, which were happy to sell it. The decision was something I could live with, even if it meant propping up our competition.

One of the more consequential changes we made in 2015 was overhauling how readers commented on our articles. Comments had always been a core part of the blogTO experience. The discussions could be heated, funny, insightful and occasionally unhinged. But the system had been difficult to manage for years. Comment spam, impersonations, and other forms of bad behaviour that clearly violated our guidelines remained a constant issue.

We finally decided to make the switch to Facebook Comments, a plugin that had been extensively updated and released that year. It was built specifically for publishers like us and required readers to log in with their Facebook accounts to leave comments on articles. It wasn’t a perfect solution, but I felt it was the best option available. The biggest downside was significant: every comment from the site's previous 10 years was wiped out. The old system wasn’t compatible with the new one, and there was no way to migrate the old comments.

The reaction to this change was immediate. “I’ve been reading your website a few times daily for as long as I can remember,” one reader wrote. “I’m officially pulling the plug and removing your website from my fav and daily reading list.” Another was frustrated that participation had been restricted: “Commenting used to be open to all. Now with the narrow option to participate, my desire to follow this has waned.”

But not everyone was upset. “I think it’s fantastic that you flipped over to FB comments,” one reader wrote. “The shift in comment culture was noticeable from the moment you changed it.”

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The change to reader comments was just one of the many significant updates coming to the website. In the next post, I’ll cover the period when we finally migrated away from the Movable Type CMS, launched a responsive website, and moved to a new site infrastructure that would propel us to record growth in the years to come.

Derek read the article and immediately messaged Chris Bateman. “Chris, please be able to write this right now,” he thought. Chris was available. Within the hour, an article was live on blogTO under the headline “Gawker says it’s seen video of Rob Ford smoking crack.”

The comments came fast. “Somehow, the madness that has been the Rob Ford saga has all felt like it was boiling down to this moment,” one reader wrote. Within a couple of hours, another noticed something striking: “It’s interesting to note who is NOT yet carrying the story: City, CP24, CTV, and National Post... Oh...and CBC.” A few minutes later, someone else posted simply: “Twitter is on fire.”

The Toronto Star, whose own reporters had viewed the same video weeks earlier, didn’t publish its own story until close to midnight. By that point, our post had been live for more than two hours. That night, thousands of people in Toronto heard the news from us first.

Chris updated the post throughout the night and into the next morning, tracking Ford’s movements, the emergence of Gawker’s “Crackstarter” crowdfunding campaign and the mounting calls for the mayor to resign. The article quickly accumulated nearly 100 comments, with readers debating, speculating, trolling and, in a few memorable exchanges, trying to explain to each other the difference between a crack pipe and a marijuana pipe.

The crack video story was the biggest of 2013, and our coverage of the ongoing Ford saga remained one of the site’s most significant drivers of traffic and engagement for the rest of his tenure. Over the months that followed, the story kept escalating. There were photos of Ford with the Hells Angels, and a video of him drunk and rambling in Jamaican Patois. There were allegations from former staffers about his behaviour at City Hall. Chris covered it all, often updating stories in real time as developments unfolded. Ford wouldn’t admit to smoking crack until November, when he told reporters it had probably happened “in one of my drunken stupors.” A second video would surface the following year.

But that Thursday night in May established something important: blogTO could compete with legacy media on breaking news. Not by producing original investigative reporting, which we didn’t have the resources for, but by being fast, being first to reach our audience, and leveraging the social media following we had built over the years to distribute the story further and faster than outlets with far more people and far bigger budgets.

It became a complement to the original reporting and service journalism that remained the foundation of what we did. When a major story broke, and we felt it was relevant to our audience, we made sure they heard about it from us.

But let me rewind. The year had actually started with a move to a new office.

I had been keeping my eye on the restoration of the Dineen Building at Yonge and Temperance, one of the most interesting building projects in the city. The heritage building, which had originally been home to a hatmaker in the late 1800s, was being brought back to life with a mix of tenants that felt perfectly suited to the Toronto we covered. The ground floor would house the first Dineen Coffee Co. A rooftop seafood restaurant called The Chase was on the way. And the building’s main tenant would be IQ Offices, which was about to open its first coworking space.

I had never expected to have an office in the Financial District, but the opportunity was there, and I took the same approach that had worked at Workplace One. I pitched a barter deal: advertising on blogTO in exchange for office space. IQ Offices agreed. On January 1, 2013, we picked up the key cards to our new home.

The team had grown considerably. By 2013, we had the largest roster of writers, photographers and editors in blogTO’s history.

Our core group of staff was anchored by Derek, Chris, our Culture and Events Editor, Aubrey Jax, staff writers Erinn Beth Langille, Jen Hunter, Liora Ipsum, Rick McGinnis and Natalia Manzocco, Staff Photographer Jesse Milns and Style Photographer Mauricio Calero.

Around them was a deep bench of freelancers covering nearly every corner of the city’s culture.

Ben Johnson was chronicling the local beer scene at a time when new breweries were opening across the city, and Toronto’s craft beer culture was beginning to come into its own. Darren Susilo was writing about restaurants in Scarborough, Markham, and Richmond Hill, covering these dining destinations well before other publications recognized them as places worth paying attention to. His piece on the hidden gems at New Kennedy Square, an unremarkable-looking mall that happened to house some outstanding food, was exactly the kind of story that set blogTO apart. Nobody else was writing about it.

Erin Scholtz pulled double duty as both a food and music writer, discovering new places to eat in one post and curating monthly concert guides in the next, from her pick for the best bowl of soon tofu in Koreatown to a rundown of every show worth seeing that month. Anders Whist, Josh Wise, Laura Adams, Tara MacInnis and Amanda Cupido rounded out the food team, covering restaurant openings and closings, writing up new spots as soon as they appeared, and producing our recurring DineSafe round-ups that readers loved and restaurant owners dreaded.

The music team was one of our largest verticals. Ryan Bolton, Adam Kamin, Eric Boshart, Jesse Ship, Julia Stead, Markit and Lori Steuart covered the local scene with genuine enthusiasm. The size of the team and their willingness to go to shows most nights of the week allowed us to provide extensive live music coverage that shone a light on Toronto’s vibrant music community, particularly up-and-coming artists and bands at smaller venues like Handlebar, The Garrison, Double Double Land, Wrongbar and Sneaky Dee’s.

Our photography team was nearly as large as the writing team. Alejandro Santiago, Brian Morton, Matt Forsythe, Hannah Jor, Matt Kozovski, and Irina No focused primarily on concerts and festivals, filling the site and our social feeds with photos from shows every week. Morris Lum, Jimmy Lu, Christian Bobak, Denise McMullin, Emily Baillie and Andrew Williamson shot everything else: the arts scene, local businesses, food, people, news and events. Together, they documented parts of the city that mainstream media rarely covered, from a Star Wars fan fiction comedy night to a shop that combined handmade art with salvaged industrial materials.

Blake Williams was our film writer. In a world before streaming services, he wrote a recurring feature called This Week in Film, picking what was worth seeing in cinemas that week and covering local festivals like Hot Docs and TIFF. Kate Fane was our window into the local arts scene, writing about everything from the city’s artist collectives to the ongoing displacement of galleries as rising rents pushed creative spaces to new parts of the city. Keith Bennie covered the theatre community, including festivals like SummerWorks, in a recurring column called This Week in Theatre. Michael Jagdeo highlighted the comedy scene in a weekly column called This Week in Comedy.

Ana Starats and Jonathon Muzychka profiled local tech startups. Erica Berman covered fitness, writing about gyms, yoga studios and new ways to work out in the city. Dylan Giuliano tracked new real estate developments.

The breadth of the team meant that when we published something about film, theatre, comedy, the arts, live music, food, beer, fashion, technology, or any of the other subjects we covered, the work came from writers who were genuinely immersed in those worlds. They knew the scenes they wrote about because they participated in them.

2013 felt like the year we were hitting our stride. The content mix was strong: breaking news sat alongside food coverage, lifestyle writing and deep cultural reporting. We had unique, originally reported stories that readers encountered on blogTO first, often days before another publication wrote their own version. We had recurring weekly, monthly and seasonal content that kept people informed about what was happening in Toronto. And we had a team with the knowledge and curiosity to make it all credible.

The Rob Ford coverage had demonstrated that we could compete on speed when something broke. But the foundation of what made blogTO work was still the daily grind: the restaurant openings, the neighbourhood profiles, the live music and arts coverage, the DineSafe round-ups, the lists that people loved to argue about in the comments. It was service journalism and cultural coverage, produced by people who cared about the city, and it was what kept readers coming back day after day.

I had more ideas for where to take the brand than we had resources to pursue. I briefly considered launching a blogTO Kids brand extension to produce content aimed at parents. With two young children of my own, the concept was appealing, but it would have been a significant departure from our existing audience and editorial focus. With multiple projects already in progress, some of which were struggling, I had to be disciplined about what to prioritize. I shelved the kids’ idea. We were never short on ideas for how to grow and expand. The constraint was always our ability to fund and execute them.

On the competition front, 2013 brought a couple of American entrants to the Toronto market.

Eater, the food blog that had started in New York in 2005 and expanded nationally four years later, launched in Toronto on October 2. I had always figured it was only a matter of time before they came north. I had been studying their content strategy for years and made sure there were no gaps in our food coverage that would give them an opening. A few days before their Toronto launch, their newly hired local editor emailed us to ask if blogTO would like to do an exclusive interview with Eater’s owner, Lockhart Steele, about the expansion. They offered early access to the Eater Toronto website before it went live. We laughed. We weren’t about to introduce our readers to a competitor. We had our sights set on doing whatever we could to prevent Eater from gaining a foothold in Toronto. Sure enough, they didn’t. They didn’t have anything to offer the city that blogTO wasn’t already doing. Eater shut down its Toronto operation less than a year later.

Thrillist, which covered food, travel and events, also started publishing Toronto content that year. Their local output consisted mostly of event round-ups and restaurant listicles, none of which added any value to what we were already doing. Several of their articles also featured photos taken by our photography team without permission. I emailed them repeatedly asking them to stop. Their editor eventually apologized and removed the images. Thrillist never gained meaningful momentum in Toronto and appears to have published its last local article in 2018.

I was also keeping an eye on Shopcastr, a Toronto-born startup that had been around since 2011. Founded by Matt O’Leary and backed by Mantella Venture Partners, the company had raised $1 million and built a local e-commerce platform that connected shoppers with independent retailers. Matt had reached out the previous year about a cross-promotion, but as the much larger brand, the trade didn’t make sense to me.

If I were being honest, I admired what they had built and wished we had the technology to complement our editorial coverage of local shops and retail. We didn’t have the capacity to do what they were doing, so I watched them cautiously. You could never predict how a startup might evolve, and it wasn’t out of the question that they could expand beyond their initial offering and start competing on our turf. By 2013, they had a new CEO and were gaining momentum, but they never expanded in the direction I feared. Shopcastr was acquired by Symbility Solutions before the end of the year.

As if the competitive landscape wasn’t enough to manage, Google added to the pressure.

On July 10, I got a call from Google’s enterprise team informing me that we would now need to pay for Google Maps. Since the site’s early days, every map element on blogTO had been powered by Google: restaurant pages and other business listings, events, and listicles. We were generating roughly 65,000 map loads per day, nearly 24 million a year, well beyond the limits of Google’s free tier. The annual cost to continue: approximately $100,000.

I flagged the situation to Abraham and Taylan immediately. Taylan had seen this happen to two other clients. In both cases, Google had doubled the price within six months. His recommendation was clear: switch to Mapbox, which Foursquare had already migrated to earlier that year, at a fraction of the cost.

The decision was easy. The execution required some deception. If Google realized we were planning to leave, they might cut our access before the migration was complete, breaking every map on the site. So I wrote back and told them we were looking into things, buying time while Abraham and Taylan worked on the switch behind the scenes. I kept stalling. By mid-August, Google told me that if I didn’t agree to the new terms by September 20, our domain would be blacklisted, we’d receive a terms-of-service violation letter from their legal team, and maps would stop loading across the site.

With days to spare before the deadline, the team finished the Mapbox migration. I wrote to Google and let them know we wouldn’t be continuing with their product.

Meanwhile, two of the major projects we had initiated the previous year were not going according to plan.

The redesign of the blogTO website by Playground was months behind schedule. By the time we moved into our new office, the bulk of the work was still incomplete. I’d show up for creative review meetings at their office near King and Spadina, only to find that the templates I was expecting weren’t ready or didn’t meet the requirements I had provided.

Playground was also now asking for more money, arguing the project was more complicated than they had anticipated. I pushed back. They hadn’t followed their own processes, and the work felt uninspired, not the calibre I expected from the agency behind The Toronto Standard’s award-winning website.

In hindsight, I had been overly ambitious with the scope. Beyond a visual overhaul, I had layered in features meant to compete with much larger, better-funded platforms: a user profile system with the ability to save articles, rate businesses, and check-in to places; a photo-sharing module where users could upload and organize images by theme; an enhanced events section; and the ability for readers to create and share their own versions of our listicles.

Around the time the Rob Ford crack video broke, Playground finally completed its scope of work, but the deliverables had issues. The few templates we did implement created a disjointed experience for readers. The street-style module from the previous year had one visual language, the new contests section had another, and the mobile version of the site looked different again. The blogTO website had no coherent identity. And by that point, the approach to web design had continued to evolve, making it clear we should have been building a responsive site rather than separate desktop and mobile templates.

I decided to salvage what we could and move on. I asked Dondy, who had done strong work on the Patio Guide and Toronto Food Trucks, to revise some of Playground’s designs into a usable state. We managed to implement a handful of templates, including the events, streams and contests sections. But we scrapped the rest. The majority of the site still looked the same as it had before the project began.

It was one of the most expensive mistakes I made while running blogTO.

The Android app was its own saga.

The smaller apps shipped first. Bars, Pubs and Late Night Eats launched in February 2013 and was designed to help people find places to drink and eat late at night. You could search by neighbourhood or subway stop, browse photos and details for each spot, and filter for places that were still open, a feature that came in handy after last call.

My favourite touch was a feature that let you shake your phone to get a random suggestion. Couldn’t decide where to go? Just shake again.

The trade publication Media in Canada covered the launch. To support the app, we ramped up our editorial coverage of late-night dining.

The Patio Guide for Android followed in May, timed perfectly to the start of patio season. Nothing marks the shift to warmer weather in Toronto quite like patio openings, and interest in patio content is always highest at the beginning of summer. Suite 66 had sold advertising to a beer sponsor across all our patio content and apps, so there was revenue at stake with the deadline. We made it.

But the main blogTO Android app remained stuck. We had gone through multiple builds and rounds of revisions, yet the app remained buggy and lacked key features. Halogen Mobile had tried to replicate the iPhone app’s design but had made changes to accommodate Android-specific conventions that I wasn’t happy with. I wasn’t willing to release anything until the Android version matched the iPhone app in both functionality and design quality.

Meanwhile, readers kept emailing to ask when the Android app would be available. Some of them had been waiting since the previous summer, when we had announced it was on the way. I responded to as many as I could, apologizing and promising we were still working on it.

By summer, we had exhausted the project’s budget. Halogen asked for more money to finish. I started looking for someone else.

My search led me to Sleeklabs, a small app development shop run by Satraj Bambra and his wife Megha. They had built the apps at Wave Financial and were fans of blogTO. When I asked them to audit the existing code, their assessment was blunt: the code base wasn’t worth building on. They recommended starting over.

There would be no blogTO Android app before the end of the year. All those readers who had been emailing us would have to keep waiting.

2013 was busy. Our audience was growing. Some of the projects we had set in motion were working. Some were not. But blogTO was on a roll.

In the next post, I'll write about what happened when the Facebook algorithm started becoming more powerful, and the difficult decisions we made to adapt to it.

Up until that point, renting office space hadn’t been a priority. The math didn’t work, and even when it started to, the terms didn’t. Commercial landlords expected multi-year commitments, and I wasn’t willing to saddle blogTO with that kind of obligation. But a new category of office space was emerging in Toronto. WeWork was still years away from opening its first location in the city, but a handful of local coworking spaces had begun to appear, including Workplace One, which had just opened near Queen and Bathurst.

I liked the space. It was modern and well-designed. And I saw an opportunity for a trade. Workplace One needed tenants. We had advertising that we could offer them. A barter deal was far more attractive to us than paying cash, so I pitched an arrangement: a small office in exchange for about $10,000 worth of advertising on blogTO. They went for it. We signed a six-month deal and moved in on October 24, 2011.

At that point, the “we” who occupied the office consisted essentially of me, Derek Flack, and Alexandra Grigorescu, who had come on board as an Associate Editor. Derek had joined at the end of 2008, starting out by covering art galleries and bike stores and, more significantly, a wide range of historical content featuring photographs from the Toronto Archives. It was the type of content blogTO became known for over the years. It was so popular that the Toronto Star once interviewed Derek about his work.

Derek had grown up in Toronto and had a deep, wide-ranging knowledge of the city that touched nearly every subject we covered. He hadn’t trained as a journalist, but he was a strong writer and photographer, and his instincts for what made a good story were sharp enough that he was constantly generating ideas, both for his own work and for the team he oversaw. Derek became not just blogTO’s third Managing Editor but also its first full-time employee.

At blogTO, our editors were expected to create content while also managing the team. Derek assigned stories, reviewed pitches and edited submissions, but he also wrote prolifically. The dual role made for long days, but I felt strongly that editors who weren’t also producing work lost touch with what the site needed. I didn’t think we could afford to have anyone in a purely supervisory position, and I also didn’t think it was a good idea.

All of our editorial planning ran through what we called the content schedule, a Google spreadsheet organized by date where we plotted the posts we planned to publish each day, along with notes, related links and status updates. Internal communication happened almost entirely over email. Slack didn’t exist yet, though we would eventually migrate to it years later. We also maintained a wiki where all of our internal documentation lived: style guidelines, best practices, CMS instructions and other resources.

We had an informal work culture. There were no set office hours, nobody was required to work from the office, and we didn’t provide equipment. Everyone supplied their own laptop, phone, camera and software. The office was there if and when our team needed it. What mattered was that the work got done and done well.

What I wanted was for our team to spend their time in the city, not glued to a desk. I wanted them to walk through neighbourhoods, duck into new shops, attend events, and talk to people. The office existed for the moments when we needed to write something up, edit a photo, or meet with colleagues. If I noticed someone spending too many hours in the office, it made me uneasy.

Over the years, readers sometimes asked me how we always seemed to break stories first. There was no secret to it. We were out in the city, talking to people, paying attention. We didn’t wait for press releases or rely too heavily on trawling social media for leads. We found the stories ourselves.

I practiced what I preached. I’d regularly explore parts of Toronto I didn’t know well, seeking out neighbourhoods like Thorncliffe Park or Keelesdale that other publications overlooked. When I went out to eat or drink, I rarely went to the same place twice, so I had more first-hand knowledge to draw on when curating lists or directing coverage.

As the site grew and revenue increased, we had resources to bring on more people and pay them more competitive wages. Our reach and reputation also meant we continued to be flooded with applicants eager to join the team.

My approach to evaluating and hiring new team members was particular.

Knowledge of Toronto was critical. I valued applicants who were actively engaged in some corner of the city’s culture and whose interests went deeper than the mainstream. That sensibility, one we had established in the site's early years, mattered as much as, if not more than, a journalism degree or industry experience.

When I interviewed prospective writers, I’d ask them questions to test their knowledge of Toronto and sensibility. There weren’t necessarily right or wrong answers, but if someone said their favourite coffee shop was Starbucks or that they liked to hang out in Yorkville, it suggested they probably wouldn’t be a good fit.

I’d ask them to name a bar on Dundas West, a cafe in Leslieville, the approximate boundaries of Parkdale or some of Toronto’s notable live music venues. I needed to hear smaller venues like The Dakota Tavern, Lee’s Palace or The Danforth Music Hall, not just the ACC (now Scotiabank Arena) or the Molson Amphitheatre (now the RBC Amphitheatre).

Turning away talented writers who simply hadn’t spent enough time in Toronto was always difficult. We’d often get applicants who had recently moved from Vancouver or another city. It was tough to find suitable roles for them unless the role didn’t rely as much on local knowledge and context. I favoured applicants who had grown up in Toronto or spent considerable time living here.

I also actively sought out writers who wanted to cover parts of the city that other publications overlooked. There was a widespread perception that Toronto media had a downtown-west bias, and I thought that was both true and a real opportunity. If we wanted to grow our readership, we had to cover the neighbourhoods where people actually lived. Former suburbs like Scarborough or North York had massive pockets of underserved readers.

In 2012, the majority of our team had not worked in media before, but Rick McGinnis was a notable exception. He was the most seasoned journalist we had, with years at Now Magazine and Metro under his belt. Rick brought a high level of reporting rigour that added depth to our coverage.

Rick was also the primary byline on our branded page in Tonight Newspaper. Tonight was a free afternoon daily, targeted at Toronto commuters heading home from work. It was a publication we had been working with since its launch in September 2009.

Back then, Tonight’s co-founders, John Cameron and Tom Hyde, asked if blogTO would be a content partner. I was skeptical about the paper’s prospects. The competition among free dailies in Toronto was fierce, with Metro and 24 Hours already well established. Dose had already discontinued its print edition, and it was clear that more people were turning to their phones for news and local information. I wasn’t convinced that a print publication whose key differentiator was an afternoon publishing time had a bright future.

But I said yes to the partnership almost without hesitation. The reasons were straightforward. A blogTO-branded page in a publication with over 100,000 daily circulation represented an enormous amount of free marketing at a time when we still needed cheap, effective ways to build brand awareness. I also knew that if we didn’t partner with Tonight, we’d be leaving the door open for a competitor to take the spot. The costs and downsides for us were minimal since we’d already be producing the content for the blogTO website anyway. I just had one condition. Tonight wasn’t allowed to syndicate our content on their website. It could only run in print.

Each issue of Tonight featured a blogTO-branded page with a feature article, usually written by Rick, alongside two shorter pieces about a local business, neighbourhood or event. The idea was to tie some of the content to a subway stop, since the paper was aimed at transit riders. Tonight would sell advertisements on the page and keep all the money. Revenue sharing wasn’t part of our agreement.

Unfortunately, Tonight didn’t succeed as its founders had envisioned. It was acquired by Annex Business Media in 2013 and folded about a year later.

Another key member of the team during this period was Chris Bateman. Chris had inherited the Morning Brew from Jerrold and created a weekly column called the Sunday Supplement, in which he unpacked a few topical stories in depth. Working under Derek’s direction, he also carved out a niche for himself by writing meticulously researched pieces about Toronto’s history.

While Derek’s history posts tended to be photo-driven, like his popular piece on what Toronto looked like from the 1860s to the 1990s, Chris’ work leaned more toward long-form research and writing, covering subjects ranging from the demolition of Chorley Park to the S.S. Noronic disaster. In 2014, Chris won a Heritage Toronto Award of Excellence for his blogTO article “That Time a Giant Gas Balloon Dazzled Toronto.”

For a few years, Chris was also one of our main news reporters, covering City Hall and the ongoing shenanigans of Rob Ford. I’ll have more to say about his coverage of the infamous crack video scandal in my next post.

Other notable writers on the team at this time included Sabrina Maddeaux, who covered fashion and later became a widely published freelance journalist for the National Post, the Globe and Mail, and the Toronto Star. Libby Roach wrote about food, restaurants and hotels, and later co-founded Auburn Lane, a women-focused Toronto publication. Dayna Winter was writing best-of lists and covering fashion and design before she left to take a content role at Shopify.

Despite all the new additions to the team, we still struggled with turnover. A number of freelancers who had done strong work for the site had since moved on. Erin Bury had pioneered our Toronto tech and startup content before becoming the Managing Editor of BetaKit and later co-founding Willful. Travis Caine had been one of our main music writers. Chandra Menard had written about local film festivals. Meaghan Binstock, Frank Kocis, Joshua Tusin, Emily Thomas and Alyssa Bistonath had all contributed to our food and restaurant sections.

In 2012, I was still working with The Office of Gilbert Li, the studio I had commissioned to design the final version of our neighbourhood maps. As that project wrapped up, we started talking about what to do next. Their specialty was magazine design, and I had always been a voracious magazine reader. I asked them to develop conceptual designs and layouts for a blogTO magazine.

The idea was to distribute it for free, subsidized by advertising, available at coffee shops and local stores, not unlike the model for our maps or the one Vice had used in its early years. The concepts they brought back loosely resembled Monocle’s look, which had already established itself as one of the best-designed magazines in the world.

Alongside the magazine concepts, The Office of Gilbert Li also developed new ideas for the blogTO logo and visual identity that could be extended across both digital and print channels, including our branded page in Tonight Newspaper, business cards, and the printed reviews and Best of Toronto decals we distributed to local businesses.

The design work was strong, and I was excited to move forward. But I hadn’t yet fully costed out the viability of publishing a magazine. Plus, the design project’s timelines kept slipping, and as time passed, the business case for me to devote constrained time and resources to a print product grew harder to make.

If blogTO was going to succeed, it wouldn’t be because of a magazine. I knew this was more of a vanity product than something that made strategic sense. We needed to win at digital media. That was the opportunity, and that was where we needed to focus.

One of the things we invested in on the digital side that year was expanding our street-style content. We’d been posting photos showing how people dressed in Toronto for a couple of years by then, and they were getting high engagement. Our readers loved looking at how different people in Toronto dressed and commenting on their outfits. Along with the photos, we would typically include details such as the subject’s first name, occupation, and how they described their style.

Some of the style was great, and some was questionable or just objectively unique. We decided to stop running the posts as regular articles and instead create an entirely new module or section of the site to house the content. The challenge with the project was that we were still struggling to migrate away from the Movable Type CMS and had built a separate Django system that we decided would serve as the foundational platform for our websites and apps in the future. We also knew we needed a new responsive site design, and I wanted to extend this module to the blogTO apps as well.

To execute the design of the new street-style module, I hired Brian Pullen, who was co-founder of Playground, the agency that designed the award-winning website for The Toronto Standard. Brian would complete the work as a freelance side project, and I was really happy with what he came up with. But, as expected, the module’s look was completely different from the rest of the site. Nevertheless, Abraham and Taylan took his design templates and integrated them into the site without much complication.

In June, the new module went live, and I posted an announcement about the changes. The main thing was that each street-style photo now stood on its own. Rather than engaging in a comment thread about a collection of photos, readers could comment on specific photos and rate outfits as “Hit” or “Miss.” We also made the content more sortable by adding tags like “leather” or “hat” so people could browse by theme.

The response to the section was positive, but I later realized that the module wasn’t built for the era of digital media to come, which largely relied on distributing content through Google and Facebook.

Various writers and photographers contributed to the street-style coverage over the years, most notably Jesse Milns, Jonathan Loek, Mona Chammas, Jessica Blaine Smith, Natalia Manzocco and Mauricio Calero.

The project with Brian was such a positive experience that I asked him if Playground would be willing to redesign the entire blogTO website. I was convinced we needed a major overhaul, one that would introduce new functionality to better position us against well-funded U.S. competitors.

Brian sent a quote for the redesign based on the brief and requirements I drafted. There would be an extensive number of templates and a significant amount of new functionality. The cost he quoted was $100,000, significantly more than we had ever spent on any one thing. But we had cash in the bank since blogTO had been growing and generating profits, so I bit the bullet and signed an agreement to move forward with the project.

The website redesign wouldn’t be the last major digital initiative we started that year. We had previously built the blogTO iPhone and iPad apps, which had a growing user base and a five-star rating on the App Store. We needed an Android app, so I found a Toronto-based development shop called Halogen Mobile that I thought would be a good fit for the job.

I wanted to keep the project streamlined. We’d replicate the iPhone app’s look and feel as closely as possible, making changes only when necessary to accommodate Android-specific conventions. Halogen’s rate was $5,000 a month. They wanted a 10-month retainer. They estimated the app would take 2 to 3 months to complete. It was the only time I ever agreed to a project with a monthly rate rather than a fixed fee. It was a mistake I would not make again.

That June, we announced on the site that an Android app was on its way. Readers were excited. We told them to expect it by the end of summer.

Shortly after the Android project started, Halogen came back to me with a proposal: they wanted to build another app, and it wouldn’t cost us a thing. They had secured $15,000 from Questrade to serve as the launch sponsor of an iPhone app about Toronto bars and pubs. The advertising revenue would offset the development costs.

So, in the fall of that year, we started a project for blogTO’s Bars, Pubs and Late Night Eats app. It would include a directory of bars, pubs, and restaurants where you could find something to eat after midnight. It would be available only to iPhone users.

Another digital project worth mentioning was launched that summer. I had observed over the years that Now Magazine seemed to generate substantial advertising revenue from its special Summer Patio Guide issue. This content vertical was a natural fit for blogTO, but I wanted to do more than just publish a series of articles rounding up bar and restaurant patios in the city.

So we created what I believe was the world’s first dedicated Patio Guide microsite for any city, as well as a Patio Guide iPhone app. An Android version would come the following year. Dondy, who also worked with us on the Toronto Food Trucks website and apps, did the design. Abraham and Taylan did the development.

The Patio Guide went live that summer, featuring a curated selection of hundreds of local patios, including photos, descriptions, and useful information such as hours of operation and whether the patio was covered, heated, or took reservations. For a while, we also included details about which beers were on tap, until we realized that gathering and maintaining that information was more trouble than it was worth.

Like the blogTO iPhone app, the Patio Guide was well-received and earned five-star ratings on the App Store. We regularly maintained the database that powered it, sending out writers and photographers to gather the information needed to add patios to the guide and remove patios that no longer existed.

While the Patio Guide still exists today, it no longer appears to be maintained. The microsite is still up, but the link to it from the website’s primary navigation has been broken for a while. The database no longer appears to be actively updated. The iPhone app hasn’t been updated since 2017. The Android version appears to have been removed from Google Play.

While we were busy spending time and money on the website and apps, we weren’t taking our eye off what was happening on social media. The previous year, we had started an Instagram account when few other Canadian media organizations seemed to be paying attention to the platform. We saw immediate traction and high engagement with our posts, which at that time were all photos since Instagram had yet to support video.

The content we posted was mainly photos that mirrored our editorial coverage, regrams of content posted by fellow users, and random shots our team captured while out and about in the city. We weren’t concerned about the platform's lack of monetization or that it drove no traffic to the website. What mattered was that we could see Instagram usage exploding, and that many users in Toronto were following us and engaging with our content.

Twitter and Facebook remained important platforms for us that year, but we also turned our attention to a newer one. Pinterest launched in 2010 and was gaining traction as a place where people could find inspiration and share photos and links to web content. Since we were always looking for ways to extend our audience through emerging platforms, Pinterest seemed worth exploring.

We hired an active Pinterest user, Melanie Dudek, and paid her to see what she could do for us. For several months, she created Pinterest boards on themes we thought people would want to share and pin, including Coffee, Date Night Ideas, and Historical Photos of Toronto. We gained some traction but ultimately concluded that Pinterest wasn’t one of the platforms where it made sense to invest our limited resources. We deprioritized the platform and moved on. Today, blogTO’s Pinterest account sits at just under 50,000 followers, though it hasn’t been active for years.

When our six-month lease at Workplace One expired in April, the arrangement had paid off for both sides. Our advertising helped them fill their Queen and Bathurst location. Their success meant they were opening a second space near King and Parliament. They were no longer willing to give us our rent for free, but offered a deal in which part of the cost would be offset by another advertising trade. We took it and stayed through the end of the year.

As we settled into our second office, blogTO had more shape and momentum than ever. A website redesign was underway that would cost more than any project we’d ever undertaken. We had multiple apps in development. Our brand was in front of thousands of transit commuters every day. And we were building an audience on every major social platform.

In the next post, I’ll get into what happened with these projects we had set in motion, including the ones that didn’t go according to plan, as well as our move into a new office space inside one of Toronto’s most exciting building restoration projects.

The team I assembled was small but enthusiastic. Ariadna Peretz, the site’s first Managing Editor, brought a group of contributors: Degan Beley, Fainne Martin, Leann Prain, Richard Murray, Rowan Lipkovits, Sean Orr, and statusq. Together, they wrote a site description that captured its spirit: “Beyond Robson is about the obscure and obvious of Vancouver. You’ll find information on everything that affects the citizens of this city, be it the next demonstration, the latest fashion event or the least comfortable park bench.”

Statusq posted first, recounting his experience at a beginner-friendly triathlon. Other early posts included a sushi restaurant roundup, a Pearl Jam concert review, a guide to running in Stanley Park, coverage of SWARM (Vancouver’s annual gallery hop), and an update on safe injection sites.

One early contribution to the music section opened with the words “Hot Loins” repeated more than 80 times, followed by a link to a MySpace page.

Like the other Freshdaily sites, we curated a sidebar full of links we called “Useful Stuff,” pointing readers to everything from the Anti-Poverty Committee and BC Ferries to the David Suzuki Foundation. We linked out to local media outlets such as The Province, Vancouver Magazine, The Westender, and Adbusters, and listed arts and culture organizations, including the Playhouse Theatre Company and the Vancouver Folk Festival. There was a blogroll linking to dozens of the city’s most popular blogs, including Darren Barefoot, Kris Krug, and Van Ramblings. The site’s sections were leaner than those on blogTO or Midnight Poutine: Arts & Film, Eat & Drink, Fashion & Style, Music, City, and Weather.

From the start, Beyond Robson had the same features and functionality as the other Freshdaily sites and quickly developed a lively community of commenters, Flickr pool participants and readers who regularly sent in tips, suggestions and feedback. The local blog community noticed right away. One person called Beyond Robson a “halfway decent looking Vancouver blog” with a layout that left “almost everything to be desired.” We took what we could get.

The opportunity in Vancouver was the same as it was in every other Canadian city at the time. The local digital media space was wide open. The incumbents, primarily The Georgia Straight, weren’t paying much attention to the internet. And readers were actively seeking out blogs and websites for local news, culture and information.

Unlike Toronto, there wasn’t any meaningful digital competition when we launched. The most popular local blog was likely Miss 604, a one-woman operation run by Rebecca Bollwitt. The site is still around today, and in 2025, Bollwitt received a well-deserved Award of Excellence from the City of Vancouver for her contribution to the city’s arts and culture. There was also The Tyee, a website founded by former Vancouver Sun journalist David Beers that had pioneered a non-traditional funding model years before non-profit-funded digital journalism became more commonplace. We didn’t view The Tyee as competition. Its scope was broader, its tone drier and more traditional, and its focus was on longer-form investigative reporting.

It wasn’t until 2008, three years after our launch, that Beyond Robson got any real digital media competition when Bob Kronbauer founded Vancouver is Awesome.

Ariadna did an admirable job running the site day-to-day with the tools and resources available to her. She recruited new contributors, managed the team, ran meetings and was my primary point of contact for everything from editorial feedback and traffic stats to design updates and technical issues. She stepped down at the end of 2006, and Sean Orr and Peter Pimental took over as co-editors.

By that point, Beyond Robson was pulling in about 40,000 page views a month, roughly a third of blogTO’s numbers. Revenue was negligible, mostly from Google AdSense, though Beyond Robson would soon be included in the largest Freshdaily network advertising deal to date, a campaign for the launch of the Mini R56. Like Midnight Poutine, the fundamental problem was audience size. We simply didn’t have enough readers to attract advertisers. I told the team we needed to reach at least 100,000 monthly page views in the near term, and well past a million within a few years, if we were going to generate meaningful revenue.

Before the end of 2006, we refreshed the website with a new logo and design, mirroring the same template updates we’d rolled out on blogTO and Midnight Poutine. A year after that, we updated it again, leveraging the Web 2.0 design and development being pushed out from Toronto to all the Freshdaily sites.

The previously generic Beyond Robson logo was replaced with one featuring a darker green, bolder typography, and a mark that combined a bird with the letter B.

We expanded the Filmmakers section, sponsored by Sony, added movie showtimes and trailers for a short time, rolled out a more robust events section and launched new directory sections for restaurants, bars and local businesses.

In 2007, we surveyed our readers. The response was encouraging in some ways and sobering in others. People genuinely liked what Beyond Robson was doing, but they wanted more of it, more frequently, across a wider range of topics.

Contributors evolved over the years. Ami Sanyal, Duran Cheung, Kristin Cheung, Jon Hilderman, Jenn Perutka, Steve Louie, Ryan Weal, Amanda Henry, Jake Tobin Garrett, Chelsea Johnston, Jenn Laidlaw, Melody Fury, Skot Nelson and J.Z. Garrod were some of those involved. I’m grateful to everyone who gave their time to Beyond Robson.

The compensation model mirrored the other sites. We used the same points system, which eventually evolved into a flat rate of $10 per post with bonuses based on page views. If a post hit 5,000 views, the writer earned $50. If it hit 10,000, it was $100.

Despite the low pay and the fact that every contributor had a full-time job or studies in addition to Beyond Robson, we ran into an unexpected problem: some people were writing too much. We were getting almost magazine-style submissions running thousands of words. I introduced a 500-word limit and asked the editors to enforce it, with exceptions for restaurant and store reviews, listicles, event previews, concert round-ups we called “Hot Ticket” posts and the Morning Brew.

Like blogTO, we gradually introduced more structure, tracked analytics more closely and leaned into SEO. Over time, we figured out what worked: listicles, coverage of major festivals and events, local news, posts about development and gentrification, and food content. The strategy I pushed was straightforward. We needed two types of posts: ones that would spark conversation and drive traffic the day they went up, and ones with staying power, like restaurant coverage and listicles, that would keep pulling in readers for months. I asked the team to stop spending time on topics that our data showed weren’t connecting with readers.

The data also made clear that a small number of star performers were carrying the site. These were the writers who posted consistently, whose work was well-formatted and whose posts routinely met or exceeded traffic targets. The majority of contributors struggled with consistency, had recurring issues with formatting or photos, or both.

Of all the contributors, Sean Orr stood out. He was getting a wide following for the Morning Brew, Beyond Robson’s equivalent of the recurring news round-up that had become a staple on blogTO. Alongside his curated links to local news stories, Sean added sharp, sometimes blistering, commentary. In a July 2008 post, next to a link from the newspaper 24 Hours with the headline “Tattoos aren’t just for bikers, inmates and rock stars anymore,” Sean wrote: “You’ve got to be kidding me. How many times has this article been written? SARAH ROWLAND YOU ARE THE WORST FUCKING WRITER EVER.”

This kind of thing did not go unnoticed. The Georgia Straight once took aim at Sean in a blog post, after he’d been openly critical of their coverage of Vancouver in his Morning Brew round-ups. Their response was to call him bitter and extend an invitation to join their “now defunct Bitter Lactose-Intolerant Asian Youth Group,” despite the fact that Sean wasn’t Asian and they weren’t sure if he was lactose intolerant.

Sean’s career took an interesting turn after Beyond Robson. In April 2025, he was elected to the Vancouver City Council. Earlier this year, he filed a defamation suit against Vancouver Mayor Ken Sim after Sim publicly accused him of distributing illegal drugs on Christmas Day. The guy who used to write all-caps takedowns of local journalists in the Morning Brew now sits at the table where Vancouver’s civic policy gets made.

By 2008, the Beyond Robson team had begun hosting concerts featuring local indie bands. A show that November featured The Bicycles, Hot Panda, The Clips and Gang Violence at DiMetric Studios on East Pender. Tickets were $10. These events were a bright spot. They connected the brand to the community in a tangible way and reminded everyone involved that there was something real behind the website.

In early 2009, I flew to Vancouver to meet with the team in person. We gathered at Salt, a restaurant in Gastown. It was an energizing meeting. The team felt that we’d built a strong foundation over the previous years and that there was still a massive opportunity for Beyond Robson to become Vancouver’s go-to destination for local news and culture. The alt-weeklies still hadn’t made any serious moves in the digital space, and there were no dominant digital-native competitors.

The optimism was real, but so were the cracks forming behind the scenes.

At some point, Kat Braybrooke took over as Managing Editor and held the role until the summer of 2010. Kat was enthusiastic, capable and effective. Traffic doubled while she was running things. But the volume of work was more than any one person could handle, given the compensation we were offering. She repeatedly asked for detailed style and formatting guides for each type of post we published, and I didn’t provide anything adequate. Instead, I sent emails to the team with formatting corrections and SEO tips, when what they needed was comprehensive documentation, structured onboarding, and real training.

The fact that we were on opposite sides of the country didn’t help. If we’d been working together in an office, things would have been far simpler. But we weren’t, and the communication gap was real.

When Kat left, she went back to school to continue her studies. Jordan Petryk, who had been Associate Editor under her, stayed on briefly but was also stretched thin, holding down a part-time job and taking seven courses in his final year of university. At one point, he wrote to tell me it had been “hell” trying to balance his duties at Beyond Robson with everything else.

We tried reorganizing around section editors rather than a single Managing Editor, but the budget wasn’t there to pay them what the work warranted. The events section alone was becoming unmanageable, with hundreds of submissions pouring in every week and not enough people to moderate them. The traffic numbers were encouraging but insufficient. Monthly page views had finally surpassed 100,000. It was real growth, but still nowhere near enough to sustain the site financially.

And then there were the technical headaches. Beyond Robson was plagued by the same problems we had on blogTO, nearly all of them rooted in the aging Movable Type CMS. At one point, the photo upload function broke entirely, forcing us to run posts without images. Comment moderation remained an unsolved problem. After Kat left, I took over recruiting new writers myself.

I also finally put together the proper onboarding materials. New contributors now had access to a wiki with resources and background on the site, along with editorial guidelines, SEO best practices, photo standards, instructions for navigating our CMS and advice on writing headlines. It was years overdue.

But the structural problems were getting worse.

The entire model behind Beyond Robson and Midnight Poutine was built on a simple premise: develop something in Toronto, then push it out to the other cities. New designs, features and tools would flow from blogTO to Vancouver and Montreal. In theory, this was efficient and scalable. In practice, the technical problems piling up in Toronto turned this approach from an advantage into a burden. Designs sat finished but never went live. Features were built, but couldn’t be deployed. The pipeline that was supposed to accelerate the other sites ended up starving them.

Meanwhile, blogTO was consuming nearly all of my attention. It was the largest of the three sites by a wide margin, with the most traction among both readers and advertisers. With limited time and resources, I felt I had no real choice but to prioritize what blogTO needed, even if that meant sacrificing the vision I’d had for the Freshdaily network and the potential of Beyond Robson.

I wasn’t able to give Beyond Robson the attention and resources it needed and deserved. The execution of the Freshdaily strategy wasn’t good enough. That’s on me.

In 2011, I decided to put Beyond Robson on hold while we worked through the technical issues in Toronto. The plan was to come back with better tools, a stronger infrastructure and the time to do it right. I replaced the website with a splash page that invited readers to leave their email addresses so we could notify them when Beyond Robson relaunched. I reached out to our contributors, thanked them and told them I’d be in touch within a month or two.

I believed it at the time.

It never happened.

In July 2011, someone wrote to ask if we actually had plans to bring the site back. If not, they said, they’d be interested in acquiring it. I didn’t respond to their email.

The failure in Vancouver stayed with me. The opportunity had been real. The demand for a site like Beyond Robson was there. And the fact that we hadn’t been able to capitalize on it was entirely on me. I had let the team down. I had let the readers and the community down.

After Beyond Robson went dark, other Vancouver sites stepped in and captured the audience we had been trying to build. The biggest winner was VanCity Buzz, which had launched in 2008 alongside Vancouver is Awesome. VanCity Buzz grew rapidly, particularly in 2010 when the Winter Olympics created a surge of local enthusiasm that their team rode to a major spike in traffic. They later rebranded as Daily Hive, expanded into other Canadian cities and were acquired by ZoomerMedia in September 2022 for $16.4 million. That was eight months after ZoomerMedia had bought blogTO.

We held onto the beyondrobson.com domain for years. When ZoomerMedia acquired blogTO, the domain transferred along with the other assets under the parent company, Freshdaily Inc. At some point, ZoomerMedia appears to have let the registration lapse. If you visit beyondrobson.com today, you’ll find something called the Beyond Vancouver travel guide.

In 2013, Scout Magazine included Beyond Robson in its Vancouver Lexicon, defining it as “a now defunct Vancouver website (run from Toronto) that tried to tackle life in Vancouver through the prism of twenty-somethings. Also, an expression of irony calling out bourgeois, juvenile enthusiasms.” They included a usage example: “That gallery opening was so Beyond Robson...”

I can think of worse ways to be remembered.

In the next post, I will circle back to blogTO in Toronto. It was the fall of 2011, and we were about to move into our first real office space.

Food and restaurant coverage had become a central part of blogTO’s editorial identity, and I didn’t want us to be an afterthought when it came to where people went to find out about Toronto’s growing food truck scene. Other publications had started covering the trend, and when they did, they kept referencing the same source: a website called Toronto Food Trucks, run by a guy named Marc MacDonald.

Marc had built something smart. He’d secured a URL that dominated search results whenever anyone searched for “Toronto food trucks” on Google. He’d filled the site with useful information, both for people curious about what trucks were out there and what they served, and for aspiring food truck owners trying to understand the city’s confusing and evolving rules and regulations. He had created a food truck infographic that had been widely picked up and referenced by local media outlets.

But Toronto Food Trucks wasn’t much of a business yet. Marc had been offered a full-time job at Shopify and was looking to sell to someone with the motivation and resources to keep it going. I was a willing buyer. We agreed on a price of $5,000, which included the website, an email list, a Twitter handle, an Instagram account and a Facebook page. If food trucks were going to be the next big thing in Toronto’s food scene, we now had a brand and a platform positioned to be at the centre of it.

We moved quickly. The site was updated to indicate its affiliation with blogTO. Whenever we published food truck content on blogTO, we’d link to the Toronto Food Trucks site, and links would flow the other way too. The content remained separate, but the two brands reinforced each other. Some of our blogTO writers, like Amy Grief and Liora Ipsum, contributed content to the food truck site. Jesse Milns shot photos.

On Marc’s recommendation, I hired Casper Yue part-time to establish relationships with local food truck operators, write about food trucks and events and manage the site’s social media accounts. Traffic wasn’t anywhere near blogTO’s numbers, but it was climbing. Social media followers were growing. Things were moving in the right direction.

The business was inherently seasonal. Traffic usage peaked in the spring and summer, when people wanted to eat outdoors, and dropped sharply in the winter, when most trucks went dormant. During the six warmest months of 2015, the site generated nearly one million page views and attracted 300,000 unique users. For a niche food-truck publication, those were encouraging numbers.

There still seemed to be more upside. I was ready to invest more heavily. Dondy Razon, a colleague from my Ogilvy days, designed an updated website and iPhone and Android apps.

Abraham handled the development of the website, building on a WordPress CMS that, unlike the one we’d struggled with for blogTO, worked smoothly. We later added push notifications so users could opt in to be alerted when one of their favourite trucks was nearby.

The site wasn’t just editorial. We built a feature that let users find food trucks on a map, and a companion tool that made it easy for truck owners to update their real-time location and upcoming schedule. The catch was that this depended on the owners actually remembering to log in and enter accurate data, which proved to be a persistent challenge. By 2015, it was clear we needed someone to be more involved in managing the relationships with truck owners, promoting locations through our social channels, and keeping the data clean.

That someone was Jaclyn Skrobacky, who would also take on responsibility for managing blogTO’s social media accounts. Jaclyn turned out to be one of the most important hires I ever made. She became the connective tissue in our operations, touching almost every piece of web, video and social media content we produced over the next decade. After the ZoomerMedia acquisition, she transitioned to a new role and remains with the company today.

We also expanded the platform beyond Toronto. We launched separate food truck websites for Vancouver, Montreal, Calgary and Winnipeg, each with its own URL, built on the same CMS and design templates. For Montreal, we invested in making the site fully bilingual.

I hired freelance writers and photographers in each city to produce local content. The iPhone and Android apps were rebranded simply as “Food Trucks,” with a city selector that let users choose which market to make their default.

One of the most valuable features of the site was the “book a truck” form. Event organizers, corporate offices, wedding planners and anyone else looking to hire a food truck could submit a request through the site. I received a copy of every submission, so I could see firsthand how heavily it was used. Hundreds of inquiries came through over the years. Truck owners told us it was an incredibly important source of leads for the events and functions they catered. I was glad we could provide tangible value to the food truck community.

Some of the inquiries were more interesting than others. In 2014, someone from Lorne Michaels’ office at Saturday Night Live reached out through the form. They wanted to send a food truck on the first day of production for one of his shows shooting in Toronto, something “locally famous, delicious and hot” for a cast and crew of about 80 to 100 people.

We also heard regularly from people in other cities. The NYC Food Truck Association once proposed a partnership to help them launch something similar in New York. The United States was never part of my strategy, so I declined.

Competition eventually arrived in the form of a site and app called Streetfoodapp, focused exclusively on reporting real-time food truck locations across every city we’d expanded into, including Toronto. They didn’t have an editorial operation; there were no articles and no event coverage, but their location data was consistently more comprehensive than ours, so Jaclyn spent time cross-referencing their listings to fill gaps in ours.

For a few years, the food truck scene in Toronto had real momentum. Festivals like AwesTRUCK and the Toronto Food Truck Festival drew enthusiastic crowds. They complemented a broader street food movement that included events like CraveTO and the Toronto Underground Market. It felt like food trucks were becoming a permanent part of the city’s culinary landscape.

They weren’t. The growth of food trucks in Toronto, and across much of Canada, was ultimately strangled by municipal regulations that made it nearly impossible for trucks to park in the most desirable locations on city streets. They were pushed to the margins, relegated mostly to festivals, private events and corporate catering. The number of active trucks declined. Prices went up. Consumer excitement faded.

Web traffic and app usage flattened. Revenue, which had always been modest, never reached a level that could sustain the operation independently. The food truck sites were subsidized by blogTO, and as the market contracted, the case for continued investment weakened.

By the time the pandemic was over, I had already decided to wind down the operation and stop investing in the brand. Toronto Food Trucks had been a $5,000 bet on a trend that seemed, for a few years, like it might reshape how a city eats. The bet didn’t pay off the way I’d hoped. But for the truck owners who booked hundreds of gigs through our platform, and for the readers who discovered their new favourite meal through the site, it wasn’t nothing.

In my next post, I’ll circle back to a story I’ve been meaning to tell for a while: what happened with Beyond Robson, our site in Vancouver.

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It was also the era of Groupon, a chapter of internet history that’s been mostly forgotten. Daily deal sites were popping up everywhere, and for a brief window, it seemed like every media company was scrambling to launch some kind of coupon offering. We flirted with the idea. A local site called TeamBuy wanted us to white-label their platform. Another company offered us an equity stake if we partnered with them. I considered all these options carefully but turned them down. My instinct was that the daily deals would be a fad and that the smarter move was to keep investing in what we were already building.

That same year, Bronwyn and I welcomed our second child. The demands at home had multiplied, and blogTO was only becoming more consuming. There wasn’t a day that went by without something requiring my attention. Nights, weekends, holidays, vacations, it didn’t matter. And that wasn’t counting whatever time and energy I could spare for the Freshdaily sites in Montreal and Vancouver. Something had to give.

Help came first on the advertising side. A handful of companies had been approaching me about representing blogTO for ad sales. One was Olive Media, which I dismissed immediately because of its affiliation with Torstar. Another was Suite 66, a firm led by the affable Marc Thomas. I’d already booked a few campaigns through them, and the relationship had been productive.

I decided to give Suite 66 the exclusive right to sell blogTO and the other Freshdaily sites. I’d continue handling our existing clients, but they would now be out in front of the agencies and media buyers I’d spent years working alongside in my previous career. Every campaign they brought in still required my sign-off. If the advertiser wasn’t right for the brand, or if they were asking for something that would compromise the reader experience, I’d kill the deal. Suite 66 never pushed back on this. They understood that I’d rather walk away from revenue than erode the trust we’d built with our community.

Suite 66 also wasn’t going to take on any local ad sales. With the exception of our printed neighbourhood maps, we had never solicited advertising from local restaurants, shops or other small businesses. If they reached out to us, we’d happily sell them something. But I’d learned early on that closing a $500 sale from a neighbourhood cafe required as much effort as landing a $10,000 campaign from a national brand. I’d also learned, from years of going door-to-door with the maps, that small business owners were relentlessly targeted by salespeople, and I didn’t want blogTO lumped in with that crowd. I wanted the relationship to flow the other way: large advertisers would fund our operations, and we’d use that revenue to produce the editorial coverage of local businesses, culture and events that our readers valued. blogTO would be something that supported local businesses and asked for nothing in return.

Which is why it always stung to see, over the years, comments on Reddit accusing us of shaking down small businesses for money in exchange for coverage. It was completely false. I corrected it every time I encountered it.

The Suite 66 relationship would endure for more than a decade, lasting through the acquisition of blogTO by ZoomerMedia.

On the editorial side, the team kept evolving in interesting directions. Chandler Levack came on to cover arts, film and culture. I’d become an admirer of her writing after reading her hot take on King West for Toronto Life. She wrote for us briefly before going to film school and becoming a celebrated director, known for films such as I Like Movies and Mile End Kicks.

Rooftopping had become a minor obsession in Toronto. A small community of photographers was scaling restricted vantage points on skyscrapers and half-finished condo towers to capture vertigo-inducing images of the city from angles nobody had seen before. It followed in the tradition of Jeff Chapman’s Access All Areas: A User’s Guide to the Art of Urban Exploration, an influential book that came out around the time I started blogTO. Tom Ryaboi, one of the most recognized names in the rooftopping scene, joined us as Photo Editor and launched a series called “Through the Lens Of” that profiled some of the city’s most talented photographers.

Jesse Milns also came aboard, gradually taking over the bulk of our photography assignments from the rotating cast of contributors who’d been handling them, such as Dennis Marciniak, Ryan Bolton and Roger Cullman. He became our first official Staff Photographer and would remain a key member of the team for years. Like other photographers who shot for us, he caught the attention of the wider industry with his work for blogTO and eventually landed higher-paying commissions from magazines and other clients.

Jesse’s arrival coincided with a significant shift in how we covered restaurants. In the early days, we’d done it the old-fashioned way: show up anonymously, order a meal, pay the bill, write a review. The approach had integrity, but it had two problems. First, restaurant criticism was democratized by platforms like Yelp, making the traditional model feel increasingly outdated. Second, it was expensive and limiting. We couldn’t photograph interiors or dishes the way we wanted, and we couldn’t afford to cover the volume and variety of restaurants we needed, particularly the more expensive ones.

So we evolved. We stopped calling them reviews and started calling them profiles, because the emphasis shifted from judgment to documentation. We’d reach out to a restaurant in advance and ask permission to visit. Nearly all of them agreed. During the visit, we’d sample a range of dishes, photograph the food, the space, sometimes the kitchen and the staff. The restaurant typically covered the meal, though on rare occasions when they presented a bill, we paid it. We instructed our writers to avoid commenting on service, since a pre-arranged visit wouldn’t reflect what an ordinary customer would experience.

The new model had obvious advantages in scale and visual quality. But it came at a cost I didn’t fully appreciate at the time. Looking back, our restaurant coverage lost something with this change. I came to miss the old reviews, the ones where a writer would note that the menu was nonsensical, that the table smelled like bleach, or that the fries likely came out of a freezer bag. Those pieces had a candour that the polished profiles, for all their usefulness, could never quite match.

The technical failures of 2010, such as the abandoned Talk! forum and the unsolved comment-moderation problem hadn’t broken our momentum. Bronwyn introduced me to a developer named Taylan Pince, a former colleague of hers. Taylan would prove transformative, rebuilding our technical infrastructure in ways that would underpin the site for years to come. He later founded his own company, which helped build Robinhood, the popular commission-free stock trading app. He’s now an SVP at a crypto company called Polygon Labs.

Taylan’s first major contribution was the blogTO iPhone app, followed by an iPad version later in the year. The iPad was still new, but many media companies were betting that it would become a widely adopted device for consuming content. Those bets turned out to be wrong, but at the time, it wasn’t unusual for publishers to develop an app specifically tailored to this device. We hired Lee Dale and Matt Rintoul at Say Yeah! for the design. The iPad version landed so well that we immediately circled back to redesign the iPhone app to match some of what users liked most about it.

Say Yeah! also completed designs for an ambitious, re-imagined user profile system: a feature set that would have allowed users to connect with friends, check in to places, rate businesses, build to-do lists and track favourites, with a friends feed showing activity across the site and apps. The whole thing was aimed at keeping pace with well-funded U.S. companies like Foursquare, which I considered more serious competitive threats than any of the local digital or legacy media brands. We weren’t able to release a full version of it until many years later due to ongoing technical challenges, but the thinking behind it reflected how broadly I was defining the competitive landscape and the need for great functionality and technology, not just great content, to compete.

Taylan also built a custom data system outside of Movable Type, using Django, to house all the structured information for our business directories: addresses, phone numbers, neighbourhoods, and categories. The website and apps drew on an increasingly complex web of APIs and third-party integrations. We were still maintaining the Facebook apps we’d built years earlier with the help of a local tech company called Shiny. The technical surface area of blogTO had expanded well beyond what our original infrastructure could support.

The editorial workflow, everything from drafting to editing to publishing, still ran through Movable Type. Replacing it had been a priority for years. WordPress was the obvious candidate, the industry standard by that point. Abraham managed to replicate our entire setup in WordPress, migrate all the content, and get it up and running in a development environment. But by year’s end, integrating WordPress with everything Taylan had built in Django remained stubbornly problematic. After investing substantial time and money in the migration, we were confronting an uncomfortable possibility: WordPress might not be the answer. We might need to build a CMS entirely from scratch.

In the meantime, the site was suffering. blogTO was crashing regularly, sometimes several times a day. Pages loaded slowly for readers and even slower for writers working in the back end. Internal server errors were a daily occurrence.

We moved our hosting to Amazon Web Services (AWS) at a cost of roughly $1,000 a month, a figure that would only climb. And we brought on Kevin Kutzko on a retainer to manage server monitoring, security, maintenance and emergency support around the clock. Kevin would remain part of the operation for years. He outlasted me, in fact. ZoomerMedia ended his contract shortly after they let me go in 2025.

The competitive landscape in Toronto continued to shift in 2011.

The Toronto Standard arrived with a design that turned heads across the industry. This was the dawn of responsive web design, and most publishers still maintained separate desktop and mobile layouts. Seeing the Toronto Standard’s site fluidly adapt to any browser window felt like a glimpse of the future. The operation behind it appeared well-funded. Lee Polydor, the founder, ran Queen Street Capital Partners, a real estate firm that owned the Burroughes Building on Queen West, where the Toronto Standard would have their offices. They hired a strong team, anchored by editorial director Chris Frey, who also served as the Toronto correspondent for Monocle Magazine, and assembled a roster of established writers at rates competitive with legacy media. I admired the editorial quality, but the cost structure looked precarious from the start. I had doubts it could hold.

On May 5, Eye Weekly published its last print issue. For decades, it had been one of Toronto’s two dominant alt-weeklies and one of the publications blogTO had set out to replace from the very beginning. Its disappearance felt inevitable, though I was personally a fan of the publication. I still consider the weekly columns by Denise Benson a treasure, a historic document of Toronto’s nightlife scene from a certain era.

The following week, Torstar unveiled its successor, The Grid, a redesigned alt-weekly on heavier stock in full colour that almost looked like a magazine. Like the Toronto Standard, it would collect design awards. But it was clearly a print-first venture, seemingly as invested in staging recurring events like Burger Week as in producing journalism tailored for a digital audience. Launching an expensive new print product while the print advertising market was contracting struck me as a characteristically Torstar miscalculation.

OpenFile, barely a year old, was already faltering. Its model, in which readers propose stories, journalists develop them, had attracted admiration and plenty of media coverage when it launched. The site had expanded to six Canadian cities and paid freelancers competitive rates. But the audience was not materializing. Traffic was low. The community hadn’t produced enough compelling story ideas to break out beyond its niche audience. And the economics depended on continued support from benefactors whose patience had limits. David Topping, the former Torontoist editor who’d been briefly running OpenFile’s Toronto operation, was already exploring other options. Derek and I approached him about joining blogTO. We spoke for several months, but he ended up taking a job at The Grid.

OpenFile shut down in 2012. The Grid ceased operations in 2014. The Toronto Standard published its final story in 2015.

That year also introduced me to something that would shape the business for the next decade: the value of maintaining a direct relationship with Google.

They contacted us to participate in a search initiative aimed at “improving local search results for users in the GTA.” Google had expanded rich snippets to include local events and wanted to ensure that the listings in our events directory were surfaced prominently. We implemented the markup and watched referral traffic to our events section climb noticeably. It was significant because event listings would become one of the most competitive content categories in the years ahead.

It also foreshadowed a pattern. Over the following decade, Google, Facebook, Twitter, TikTok and Snap would all cultivate relationships with handpicked Canadian publishers, offering access to exclusive events, training and revenue-generating partnerships. Sometimes blogTO made the list. Sometimes we didn’t. There was never transparency about who was included or what we might be missing. You’d only find out you’d been excluded when someone else mentioned it.

I had always been focused on digital, but 2011 was the year I formally stepped away from some of the offline initiatives that had defined blogTO’s early brand-building efforts.

The neighbourhood maps, a fixture since 2007, ended. I’d started delegating parts of the process, sales calls to local businesses, distribution runs, but the people I hired didn’t execute the way I needed them to, and the economics deteriorated. Revenue dropped. Costs rose. And the case for printed maps was weakening by the month. Google Maps was now on every smartphone. Yelp, Foursquare, and now our own iPhone app were doing, at least in part, what the maps had done on paper. By fall, I decided not to produce another edition.

We also retired our annual photography exhibitions with the Contact Photography Festival. The openings were well attended and offered a rare opportunity to bring our online community together in person. But they consumed time and energy I could no longer spare. In their place, we expanded our media sponsorships. Rather than producing our own events, we’d increasingly lend our promotional reach to other people’s. Film festivals like Inside Out, Hot Docs and the Images Festival became recurring partners, alongside events spanning food, music, fashion and culture, such as Wavelength, Fashion Art Toronto (FAT), and Night It Up!, to name a few.

By year’s end, annual revenue had surpassed $500,000. We turned a slight profit. The majority of our spending went to editorial production and the mounting investment in technology, design and development for the website and apps. Everyone was still on contract. A few contributors were approaching full-time hours, but blogTO officially had zero employees. The traffic kept climbing. The infrastructure kept straining. The competition kept arriving.

The following year, we’d make our first acquisition.

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Abraham, our longtime developer, spent every available hour trying to trace the breach. A hacker had planted a backdoor script that granted them access to the server, and malicious code was being injected into our JavaScript files, triggering the warnings readers saw.

We needed more help. My friend’s younger brother, Deniz Okten, who specialized in security, stepped in. Together, they worked to determine whether the vulnerability was in our CMS or with our hosting provider, Media Temple. For weeks, we didn’t know. When they finally traced it to the hosting environment, we started over: new server, new code, every administrative access point locked down.

The whole episode consumed about a month. A month of wondering how much trust we’d lost with the audience we’d spent five years building. It confirmed something I’d been worrying about for a while: our technical foundation was overdue for a serious overhaul. Movable Type, the CMS we’d been running on since the very beginning, had fallen out of favour with the developer community. Finding people who could work with it was becoming genuinely difficult.

Despite the malware incident, we kept growing and soon boasted that we had reached 375,000 unique users and generated 1.5 million page views per month. Our media kit described blogTO as the number one website for Toronto news and culture. The Toronto Blue Jays, Ford, Nike, Mirvish, OCAD and Bud Light were all buying campaigns. The City of Toronto had become a regular advertiser, and we ran reader-submitted photo contests with them for events like Nuit Blanche and Summerlicious.

It was a year of significant changes on the editorial team. Tanja had left to join Yonge Street magazine, a newly launched website. By the end of the year, Jerrold would scale back his role to take a full-time job at Loblaw Digital. Derek Flack, who had been a contributor to the site, stepped up to replace him as Managing Editor.

These departures reflected a pattern. blogTO had become a launching pad. Many of our contributors had come to us as aspiring writers, photographers, and journalists seeking their first opportunity in media. They got bylines, built portfolios, covered real stories, and then moved on to established publications and companies where they could earn more money. It was something I was proud of, even as it created a constant challenge of replacing talent we couldn’t afford to keep.

Some of the newer contributors included future Globe & Mail columnist Robyn Urback, who mostly wrote about food, fashion and something we called “Get to know a street.” Ben Spurr was crafting curated weekly event roundups in a column we called Radar. Luke Champion, who now owns the excellent Good Cheese on Gerrard East, was eating a lot of fries, curds and gravy as he completed The Great Toronto Poutine Challenge. Lauren Wilson was writing a series called Fridge Files that photographed and documented the contents of people’s fridges. A similar recurring feature quickly surfaced on Toronto Life.

That year, we also started receiving unsolicited emails from people asking about internships, the beginning of what would become a long pipeline of writing, photography, and, later, video and social media interns, many of whom eventually became full-time staff or regular freelancers.

Other publications were paying attention to what we were doing. Sometimes too closely. We’d regularly see our stories turn up on other sites the day after we published them, almost always without credit. I once reached out to the Toronto Star to complain. The writer apologized and told me they had actually included a mention that blogTO had reported the story first, but their editor had removed it. On CBC Radio, we’d hear our stories discussed on air. Instead of crediting blogTO, they’d simply attribute it to “a Toronto blog.”

The competitive landscape kept shifting. A new publication called The Mark launched with considerable funding and fanfare, positioning itself as a platform for long-form essays on politics, economics and culture. I didn’t think the model would work, and it didn’t, but while it lasted, they were actively recruiting our writers, offering rates we couldn’t match. The Mark paid $450 a week for a full-time contributor. Our rates were lower. They succeeded in luring Ben Spurr away, and I knew they’d approached others.

Yahoo! was also making a big push into local coverage. They asked if they could syndicate our content. They weren’t offering to pay for it. I said no.

We continued to build out sponsored editorial sections, extending the model that had started with the Zune-backed Artist Gallery. A Filmmaker’s section backed by Sony featured profiles of emerging local directors. A section called Movers, Shakers and Jet-setters, sponsored by Virgin Atlantic, profiled people like Kevin O’Leary and Amanda Lang.

A Toronto Fashion Week section, sponsored by Stylesense, featured runway coverage from our regular contributors Kevin Naulls and Briony Smith. We hired James Kachan to take photos. Istoica filmed all the collections. We uploaded their videos to Vimeo, which was the popular video platform of the day.

Fashion Week, held twice a year, was an event we devoted significant resources to because the sponsorship covered the costs. The sponsor had no say over the editorial, but they were the exclusive advertiser alongside the content. That distinction always mattered to me.

We partnered with the Contact Photography Festival again, this time for an exhibit called 99 Cents. The theme explored the psychology of 99-cent pricing and invited readers to submit photographs that captured the idea. The top five photos were chosen by popular vote, and five more were selected by a jury. The exhibit was at Show & Tell Gallery on Dundas West, and we got Sony to sponsor it. At the opening night party, beer and wine were priced at 99 cents. We served custom blogTO cupcakes again. DJs played. The gallery was packed despite a downpour.

In the spring, we released another edition of our neighbourhood maps, expanding to Ossington, The Junction and Baldwin Village.

In June, the G20 Summit came to Toronto, marking a pivotal moment for the site.

There were barricades across the downtown core and protests in the streets. Heavily armed police were on every corner. It felt like the first major international news event in Toronto, where blogTO could demonstrate what it meant to have a community behind it. Photos poured in from readers through email and our Flickr pool. Twitter erupted. Our writers and photographers threw themselves into covering something that felt important and historic, and none of it required press credentials.

Jerrold coordinated the team’s coverage while doing a significant amount of the reporting, crowdsourcing, and tweeting himself. I was in the thick of it too, visiting the detention centres on Eastern Avenue to document what was happening. The photos I took there were later sought out by academics, authors and documentary filmmakers revisiting the events of that week.

In the wake of the G20, Twitter became an even more central platform for us. We were one of the biggest accounts in Toronto. Jerrold developed a comprehensive strategy with guidelines for tweet timing, frequency, hashtags, and community engagement. Sharing links to our own articles was a small fraction of what we were doing. The real value was in the conversation.

We also started writing regularly about business closings after our analytics showed that readers were drawn to it. We coined a term for it, Deadpool, borrowed from the blog TechCrunch. When a place closed, it entered the Deadpool.

The City of Toronto had launched its Open Data initiative at the end of 2009, marking the beginning of the city’s open data movement. We were among the first to take advantage of it, integrating DineSafe health inspection records into the site so readers could easily look up whether their favourite restaurant had passed its last inspection. We’d soon start publishing weekly roundups of restaurants that received infractions. Readers loved it. Restaurant owners were considerably less enthusiastic. Inspection information that had previously gone almost entirely unnoticed by city residents was suddenly getting a major spotlight.

Behind the scenes, we were investing in technology to keep pace with the site’s growth. We launched a redesigned homepage that moved decisively away from the original blog layout and gave greater visibility to the wide range of content we now offered, while also highlighting slightly older content that still had value.

We were also paying close attention to how Google was evolving. The introduction of rich snippets in 2009 meant that search engines could now surface more detailed information from websites that structured their content properly. We began rebuilding how our content was organized under the hood, ensuring that everything from restaurant listings to best-of posts was formatted in a way Google could read and reward. At the same time, we were building APIs for our core content so that our directories, best-of lists, events and articles could power products beyond the website itself, starting with the iPhone app we’d been working on all year.

There was constant maintenance work: CMS upgrades, bug fixes, design tweaks, and browser compatibility issues. We invested in a better backup system to guard against another malware incident. And we began seriously discussing migrating away from Movable Type to WordPress across all three Freshdaily sites.

The comment situation remained a major headache, but we were now also fielding a new category of complaints: businesses objecting not to what readers said about them in the comments, but to how we covered them editorially. Ubisoft’s communications team took issue with an article about their new Toronto office that touched on gentrification. Extreme Fitness was unhappy with a piece we’d headlined “Extreme Fitness, Extreme Ripoff?”

The CMS problems had real consequences beyond comments. We spent about half the year working with a small web company in San Francisco on an ambitious project: a user profile system and a discussion forum we planned to call Talk! that we hoped would also address our challenges with comment moderation and make the website stickier.

The San Francisco team had built something similar for a food site called Serious Eats and had developers experienced with Movable Type, which is why we thought they were a fit. After six months, the project was still too buggy to ship. I pulled the plug. It was an expensive lesson in the limits of trying to build features on out-of-date infrastructure.

Our team gatherings had evolved, too. The basement meetings where we’d reviewed stats and run tutorials had given way to what we called blogTO Socials: get-togethers three or four times a year at a bar or restaurant. I’d try to pick somewhere newly opened each time, in a different neighbourhood, so people could experience a place they hadn’t been before.

In November, a legacy Toronto media company approached me about buying blogTO. The owner was shrewd enough to recognize that digital was going to reshape the media business and that they didn’t have a digital property of any substance. blogTO, they believed, could fill that gap.

I’d never started blogTO with the intention of selling it. I’d never had an exit strategy. But I figured there was no harm in hearing what they thought the site was worth.

Their initial offer valued blogTO at $1 million: $250,000 upfront for a 25% stake, with an option to acquire an additional 24% over the following two years for another $250,000, bringing their total ownership to 49%. They eventually raised their valuation to $1.5 million. There were conditions. The initial $250,000 would need to be reinvested in hiring sales staff and improving the site. Any expense over $10,000 would require their approval. Earnings would be paid out as dividends, 49% to them. And they wanted the first right of refusal on the remaining 51% if I chose to sell.

I didn’t think it was a great offer. But more than that, I didn’t want a partner. I was happy where I was. I wanted to see how far I could take this on my own.

I said no.

It was the right decision. blogTO was growing faster than ever. The brand had become part of the fabric of life in Toronto. In the years ahead, we’d finally hire our first full-time employee. We’d get a real office. We’d release four different iPhone apps. We’d embark on a six-figure website redesign. And we’d make our first acquisition.

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blogTO had grown into a site that did a lot of different things. We published local news and culture coverage, which put us up against established local media and newer digital rivals like Torontoist. We had restaurant reviews and business directories, which meant we were now competing in a space alongside platforms built specifically for that purpose. We had event listings, which increasingly meant competing with Facebook itself. My view of who we were up against had become very broad.

So who were the new competitors?

Torstar Digital had launched OurFaves the previous year, an online city guide built on user-generated reviews and staffed largely by unpaid interns.

Dose, the Canwest Media publication that had launched as a free daily newspaper in 2005, had dropped its print edition and gone entirely digital. It had more writers and resources than we did, and its website looked good. Dose was more entertainment and celebrity-focused and didn’t go nearly as deep into the city-centric reporting blogTO had become known for, but it was close enough to our space that I paid attention.

She Does the City was launched the previous year by Jen McNeely. It had started to build a small but loyal following. Its coverage deliberately skewed female and tended to revolve around the downtown west scene. I didn’t view it as a direct competitor, but it was another publication going after a piece of the Toronto audience.

Vice Media had opened a Toronto office. They were still primarily a print magazine at the time, but they were beginning to invest in digital, and there was some concern that they’d start stepping on our turf. One of their editors even got in touch with us to propose sharing content between the two sites. I wasn’t interested.

Then there were the well-funded American platforms expanding into Canada. Yelp launched in Toronto in 2008, one of its first international markets outside the United States. Urbanspoon, another major player, was also competing in the restaurant review and discovery space. I felt we needed a strong competitive offering in place to defend our position before these platforms gained too much traction in the Canadian market.

The answer, as far as I could see, was to keep doing what we were doing but do more of it, faster, and with better tools.

blogTO had always been a community-driven site. By 2008, we’d created a wide range of ways for people to participate beyond just reading and commenting. You could submit different types of content, such as articles, reviews or event listings, send us news tips, or even submit photos that we would rotate next to the logo at the top of the site. In a pre-Instagram world, our Flickr group was a popular place to share photos, and we regularly featured Flickr submissions in our articles.

Jerrold kept our Twitter account active and interesting. He was always coming up with fun ways to engage followers. And when someone in Toronto joined Twitter, blogTO was often among the first accounts they were recommended to follow, which helped our following grow quickly.

Early that year, I gave a presentation called “Website Marketing in Facebook” at a Toronto unconference called Facebook Camp. Facebook had launched its developer platform the year before, and we were among the first Canadian media companies to build something on it. Our Facebook application was called Toronto Faves, and it let users create a list of their favourite Toronto restaurants, bars and other places and display it on their Facebook profile.

On the blogTO website, we added an “Add to Faves” button next to some of our content. We built a leaderboard so you could view the most popular faves by category or neighbourhood. Within months of its launch, we had nearly 1,000 users, and Facebook had become our second-largest source of traffic after Google.

We followed it with a second app for events. By this time, most people in Toronto had started using Facebook to promote their events. Our app let them push those events directly into blogTO’s event listings with a couple of clicks. We also built an internal tool for our team to do the same. What had been a tedious process of manually adding events one by one suddenly became something we could do at scale. Hundreds of events could be added with a few clicks.

Apple launched the App Store that summer. We’d already built a basic mobile site from our RSS feed, but it wasn’t a great experience and using it on your phone likely meant watching your data bill go up.

The App Store changed things. We immediately started working on an iPhone app that would feature our latest articles, a Best of Toronto section, the ability to look up restaurants and other businesses, and our event listings.

The content on the site kept getting better, and page views were going up. Many of the team members from the early years had moved on, but a new crop of writers had joined with fresh ideas and perspectives.

Robin Sharp was writing a popular series called Toronto Portraits that profiled up-and-coming creatives in the city. His subjects included people like Anthony Furey, who would years later run for mayor of Toronto.

Jonathan Castellino had a regular column called Toronto’s Forgotten Landmarks, in which he’d photograph and write about buildings the city had abandoned, or people had stopped noticing, such as the Canada Malting Company plant on the waterfront.

Chris Reynolds was exploring the fringes of Toronto in a series called GTA Tripping, turning up places most of us had no idea existed, like a gun range in Stouffville where anyone could walk in off the street and fire a shotgun.

Carlos Weisz posted weekly sketches with a Toronto theme under the name noteTOself.

We also launched a new section on the site, the Artist Gallery, and had Microsoft Zune pay for it. The Zune advertising dollars allowed us to hire a team of popular photobloggers (Sam Javanrouh, Rannie Turingan and Istoica, the collaborative team of Chris Altorf and Jessica Hayes), to curate the section and take photos of all the artists. The deal mattered beyond the immediate revenue because it gave us proof of concept for something we could sell to other advertisers.

We partnered with the Contact Photography Festival again, this time staging an exhibit called 50 Artists 50 Photos at Barbershop Gallery in Parkdale. It was an extension of the Artist Gallery, featuring the same photographs of the 50 emerging Toronto artists taken by the photobloggers. Opening night was packed. We served custom blogTO cupcakes and handed out swag.

We launched a new podcast called DiverCity, produced and hosted by Nana Aba Duncan, who has since had a distinguished career as an award-winning journalist at the CBC and is an Associate Professor at Carleton University’s School of Journalism.

We also leaned harder into bar and nightlife coverage, launching a redesigned bar section and an ongoing series that counted down the 50 most essential bars in the city. We hired freelance photographer Eugen Sakhnenko to take the bar photos. Jessica McCann did most of the writing.

We focused a lot on arts and culture coverage during this period. I wanted to amplify what the city’s creative community was doing and shine a spotlight on emerging artists because I felt no other local media was doing so. But the analytics were clear. A thoughtful gallery profile or artist interview got a fraction of the traffic that news about a rat infestation at a local restaurant generated.

Traffic was growing regardless. We’d been the first site in the city to aggressively optimize content for search engines, and Best of Toronto posts had become our most reliable growth engine. If you searched for “best brunch in Toronto” or “best bike stores in Toronto,” there was a good chance you’d end up on blogTO. We started handing out window decals to Best of Toronto poll winners, a tactic I’d borrowed from Now Magazine and Eye Weekly.

That summer, we hit 663,000 page views in a single month. It was a new record. By December, we’d reach one million monthly page views. It was a cause for celebration, even if hitting this target was a year behind schedule.

But the editorial operation was straining. Our target was six to ten posts a day, and we were regularly falling short, particularly on weekends. The team was large on paper, but many writers were only posting once or twice a month. Revenue and traffic were both climbing, but the editorial model needed rethinking.

I was handling all of the advertising sales myself. Banner rates ranged from $5 to $10 CPM, with a special rate for local businesses starting at $50 a month. All sales were based on inbound leads. I wasn’t cold-calling or proactively selling to anyone. We were selling out most of our inventory, which meant the real constraint was traffic: we needed more of it to generate more impressions to sell. I didn’t want to create more inventory by adding more ad units to the site. I knew that would piss off readers.

My sales approach was borrowed from my years on the agency side: be easy to work with, deliver on your promises, and throw in bonus impressions when you can. I’d watched publishers lose repeat business by under-delivering, and I wasn’t going to make that mistake.

That fall, Bronwyn and I had our first child. We’d moved from our apartment at Ossington and Argyle to a semi in Leslieville to make room. The night before he was born, we ordered Indian takeout from Bombay Palace because someone had told us spicy food might help induce labour. Bronwyn still reminds me that while she was having contractions later that evening, I was writing up a review of the meal.

We expanded our printed neighbourhood maps to new areas and produced a custom edition of our King West and Queen West map for the EF International Language School, which helped us reach international students in the city.

We also started printing copies of our restaurant reviews and giving them to local businesses to post on their walls, another low-cost, highly contextual way to get our brand in front of people in Toronto.

On December 12, 2008, Torontoist editor David Topping posted an announcement that seemed to catch everyone off guard. The site was shutting down. Gothamist, its New York-based parent company, had decided to close Torontoist and redirect resources to its more profitable American properties. Topping told the press that the site couldn’t be sustained under its current structure and that the worsening economy made its future even more uncertain. Of all the sites in the Gothamist network, Torontoist was the only one losing money.

I wasn’t surprised. I don’t think Gothamist fully appreciated, when they launched Torontoist, that the Canadian advertising market was a completely separate ecosystem from the one that funded their American sites. They would have needed to build relationships with Canadian agencies and brands from scratch. They also likely hadn’t anticipated the level of competition they’d face from blogTO.

After the closure was announced, several parties entered discussions with Gothamist about acquiring the brand. The financials weren’t encouraging. Total revenue for 2008 was just under $14,000. The site had no liabilities and no writers under contract, so an acquisition would have been straightforward. The one complication was that Gothamist initially wanted to license the brand rather than sell it outright, with an annual fee plus a percentage of future revenue.

In April 2009, Torontoist was sold to Ink Truck Media. The site would continue under the new ownership.

The competitive pressure continued to mount in 2009. Foursquare launched in early spring and expanded to Toronto within months. It leveraged the same Facebook developer platform as our Toronto Faves app but was far more sophisticated, changing how users interacted with local businesses in real time.

Between Foursquare, Yelp and Urbanspoon, the restaurant review and discovery space was now filled with well-funded American platforms. We couldn’t compete with their engineering, capital, or scale, but I felt we needed to be in the game and to defend our position in Toronto and the other cities where Freshdaily operated. Significantly increasing our investment in technology became one of my top priorities.

One notable misstep that year was my decision to add movie listings and trailers to the site. It required us to sign our first content licensing agreement to get showtime data from all the Toronto cinemas. We spent money to license the data. We spent money on redesigning the site to accommodate it. But it never gained much traction, and we dropped it a couple of years later. People came to blogTO for original content. Years later, when people suggested adding crosswords and other features readily available elsewhere to the site, I would think back to this experience.

The single biggest headache around this timeframe was comment moderation.

Comments had always been one of blogTO’s most popular features. People would often tell me they visited the site just to read the comments. They could be harsh, funny and surprisingly informative. But the system allowed anyone to post anonymously without logging in, and as the site grew, the volume became impossible to manage. We were getting hundreds of comments a day and didn’t have the people or the tools to keep up.

The problems went beyond article threads. Across our site, on pages for restaurants, bars, gyms and clothing stores, people had started leaving reviews, similar to what you’d see on Google today. Some were fair and useful. Many were not. Commenters accused business owners of being dishonest or complained about rude staff. If you can picture the worst Google reviews you’ve ever read, that’s essentially what we were dealing with, except we were the ones getting the angry emails from the business owners.

It was almost a daily occurrence. A business owner would contact us to demand that the comments be removed. We’d take them down if they could show us a clear violation of our comment policy. People who’d posted something impulsive would email us days later asking us to delete what they’d written. The Toronto Police would sometimes reach out requesting any identifying information we had about commenters who had threatened violence. Lawyers sent emails on behalf of businesses. And more than once, a commenter wrote to let us know they were being sued by a business over something they’d posted on our site.

That year, we received our first formal legal threat. A lawyer representing a local hair salon demanded we pay $100,000 in damages. The salon’s owner had gotten into a back-and-forth with people who had left negative comments on a page that reviewed her salon, and it hadn’t gone well. She was blaming us. I believed we’d done nothing wrong and decided to fight it. I looked up the lawyer who represented The Globe & Mail, a media law specialist named Peter Jacobsen, and hired him. It cost us money I hadn’t planned on spending, but he got the matter dismissed.

We tried to address the moderation problem by adding Facebook Connect, a login system Facebook had recently rolled out, which gave users the option to sign in with their Facebook account before commenting. Some people used it, but anonymous commenting remained far more popular, and the underlying problem didn’t go away. There was no immediate technical fix available to us while we were running on what had become an outdated and increasingly problematic Movable Type CMS. On the worst threads, we’d just shut comments down entirely. It was a blunt solution, but sometimes it was the only one we had.

Despite the headaches, by the end of 2009, blogTO was in the strongest position it had ever been. Traffic was growing. Revenue was climbing. The brand had become a fixture of daily life in Toronto. I had no idea that in less than a year, someone would offer to buy it.

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Montreal was always part of the plan. I’d spent four years there as a student at McGill, my father had grown up in the city, and a lot of his family still lived there. I had a connection to Montreal that went beyond opportunity.

In August 2005, the same day we launched Beyond Robson in Vancouver, I reached out to two friends from university who were still in Montreal. John MacFarlane and Hannah Hoag had both gone into journalism after McGill. They were both immediately interested and brought along a mutual friend, Sara Falconer, to round out the founding editorial team.

A few name options were floated, but Midnight Poutine stuck. Sara’s reasoning was simple: it was “something we all eat way too much of.”

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To connect the publications, I created a brand called Freshdaily. The sites would be sold together as a bundle to national advertisers looking to reach audiences in Toronto, Montreal and Vancouver simultaneously. The sites would share a CMS, design and development teams, meaning certain functions would be centralized, which would, in theory, create efficiencies. Documents such as media kits and guidelines would be created once for blogTO and then adapted for the other cities. New features could be tested in one market before rolling out to the others.

The only thing that wouldn’t be centralized was editorial. Each site would have its own team of editors and contributors, all of whom lived in the city they were covering. I understood even then that you couldn’t build a credible local publication with writers based elsewhere. This seems like an obvious point, but in the years that followed, plenty of sites tried exactly that. It never worked.

Midnight Poutine launched on September 28, 2005, timed to coincide with that year’s POP Montreal festival. Coverage of the indie music scene would become a defining part of the site’s identity over the coming years.

Aside from John, Hannah and Sara, the initial team consisted of Andrea Allen, Ange-Aimee Woods, Anna Lambton, Cat Macpherson, Omer Rashid, Dave Hill, Drew Daniels, Francois-Xavier Tremblay, Josh Dobbs, Kate Irvine, Mike Irvine, Matt Silver, Mog Hewings, Robyn Fadden, Roxanne Arseneault, and Shawn Petsche.

Petar Stoilov, who had designed the blogTO logo, created the original look for the Montreal website: dark blue text on a yellow background. The CMS gave us the flexibility to define unique content sections, so Midnight Poutine launched with categories such as Celebrity, Sex, Chips, and Science & Health, alongside the usual Music, Arts, Film, Fashion, and Food.

John knew many young English-speaking writers in Montreal, many of them aspiring journalists looking for a place to publish. He attracted a roster of hungry, talented people eager to get their names on bylines. Getting published in the city’s established media outlets, such as the Montreal Gazette, The Mirror, and Hour Magazine, was difficult. Midnight Poutine offered something those publications couldn’t: you could write something and see it online immediately, with your name on it.

What struck me about the early writing was how much personality it had. One contributor reviewed a cafe located above a funeral home on Saint-Laurent, reporting that the coffee had “an eerily toasty roast” and was served at a temperature she described as “a wee bit post-mortem.” She was charmed by the place despite the watery lattes.

The site’s sex column was introduced by a writer whose only self-described credential was that he knew roughly a hundred people he cheerfully described as “slutty”, and because he stayed out of the fray himself, they all told him their stories.

A recurring series called First Dates reviewed Montreal restaurants through the lens of whether you’d want to take a date there, combining practical food criticism with the anxiety of first impressions.

And then there was Metro Roulette, the site’s most popular recurring feature, where contributors picked a metro station at random and spent the day exploring the surrounding neighbourhood.

John once visited the Préfontaine station in Hochelaga-Maisonneuve, discovering breast-shaped ashtrays in a head shop, a storefront for a certified clown service, and what he was confident was a top-five all-time poutine at a greasy spoon called Davidson Lunch that had been serving the neighbourhood since 1954. The series was an excuse to wander, eat, and pay attention, and it captured something essential about Montreal: a city of wildly distinct neighbourhoods that rewarded curiosity.

This was the kind of writing that made people love Midnight Poutine. It was funny, specific, and unmistakably Montreal.

Like blogTO, the Midnight Poutine editors organized team meetings and social gatherings. They’d send me an invoice for the food and drinks, which I’d cover, along with meeting notes, questions and action items.

Some of the early contributors went on to notable careers. Asmaa Malik is now head of the Journalism Program at Toronto Metropolitan University. Susan Krashinsky Robertson is a reporter at The Globe & Mail. Hannah became a prominent science journalist and now holds a senior role at the CBC. John also worked at the CBC, served as editor at MTL Blog, and is now a Senior Reporter at Yahoo Finance.

John started the site’s podcast, and when Jeremy Morris took it over, he transformed it into the music show it became: the Midnight Poutine Weekend Playlist. Jeremy was a PhD student in communications at McGill who had been contributing written roundups of upcoming shows. He started stringing together songs from bands playing small Montreal venues, added his own voice between the tracks, and a format was born. About an hour of music each week, with Jeremy talking about the artists and where to see them live.

Jeremy eventually became the site’s Music Editor and then Managing Editor. Sara left at the end of 2006. Hannah and John departed the following year. Jeremy kept the podcast going, often by himself, eventually bringing in co-hosts. The show ran for over 300 episodes. He later wrote a book about podcasting and is now a professor of Media and Cultural Studies at the University of Wisconsin-Madison. I loved listening to the podcast from my apartment in Toronto. It made me feel connected to a city I cared about but no longer lived in.

The podcast was a passion project. It never generated much revenue, and its audience, while devoted, never grew beyond a niche. But for the people who listened, it was a window into Montreal’s music scene that didn’t exist anywhere else.

About a year after launch, Midnight Poutine got a redesign from Jay Delmarr. He came up with a few logo concepts for us to choose from. One laid out the name horizontally in a dreamy, organic style.

Another stacked the words vertically. We went with a third option: the site’s name in lowercase script alongside a blue tree, which, as best I recall, was a nod to the greenery that covered the city, particularly the trees on Mont Royal.

Despite the quality of the writing and the strength of the podcast, the numbers were a persistent challenge.

Midnight Poutine consistently generated the lowest traffic among the three Freshdaily sites. Posting frequency was inconsistent. Contributors would go quiet for stretches, pulled away by day jobs, personal issues, or the simple reality that there was no meaningful pay to keep them motivated over the long term. The incentives that seemed to mobilize the blogTO team in Toronto didn’t carry the same weight in Montreal. And unlike Toronto, I couldn’t fill gaps by producing content myself. I was in another city.

I wasn’t involved in Midnight Poutine’s editorial decisions. I left that to the team but read the site every day, reviewed stats weekly, and occasionally sent notes with feedback and insights. The team was receptive, but the fundamental problem was structural: everyone had a day job or was looking for one, their available time was limited, and the initial excitement that had drawn people to the project gradually wore off, especially as we introduced more guidelines and structure.

Montreal was also a challenging market for a reason unrelated to effort. Midnight Poutine was an English-language publication, and the English-speaking audience in Montreal was considerably smaller than in Toronto or Vancouver.

In November 2006, I laid out the situation plainly in an email to the editors. October traffic had been roughly 16,000 page views. November was tracking even lower. Daily visitors were fewer than 250. For context, blogTO was approaching 117,000 page views that same month. I told them our goal for blogTO was 1,000,000 page views per month by the end of 2007. Midnight Poutine was on a completely different trajectory.

The compensation model mirrored blogTO’s: revenue was shared with contributors. But with traffic this low, there was almost nothing to share. At one point, I calculated that even if we sold all our ad inventory for the entire year, we’d bring in only $6,000. The issue wasn’t finding advertisers willing to spend. It was that not many advertisers saw value in a site that got so few page views every month.

Despite the discouraging numbers, there were some early signs that the Freshdaily network model could work from an advertising perspective. I was starting to sell campaigns across all three sites as a bundle. American Apparel was one of the first bigger brands to buy in, though as I later discovered, they didn’t always pay their bills on time. I eventually had to write off some of the receivables when they filed for bankruptcy years later.

But the reality was that very little of this revenue trickled down to Midnight Poutine’s contributors because the site delivered so few of a national campaign’s overall impressions.

People genuinely liked the Midnight Poutine brand. They liked Metro Roulette, the music and arts coverage, and the Weekend Playlist podcast. But they wanted more from us. More frequent posts. Broader coverage. We still didn’t have enough of the content that was starting to drive traffic on blogTO, such as restaurant reviews and best-of posts. Indie music coverage served a niche audience and wasn’t an effective growth engine.

By the end of 2007, most of the initial team had moved on. The original content categories had been trimmed down. A smaller, younger crew was covering mostly music, arts, film and food. The challenges were compounding: audience growth, the limited English-language readership, the struggle to shift the content model toward something that could generate real traffic, retention problems as motivation waned, and ongoing technical headaches with the CMS. And my own time and resources were increasingly consumed by blogTO, which was setting new growth records every month.

Despite all of this, Midnight Poutine had something that numbers alone couldn’t capture. People in Montreal genuinely loved the site. The content was fun, interesting, and clearly a labour of love. The community understood what we were trying to do and appreciated it. As John told me recently, he thinks about the contrast between Midnight Poutine’s positive reputation and what eventually replaced it in the Montreal market. MTL Blog, which became the dominant English-language blog in the city a decade later, was, in his words, “despised for lots of good reasons” by the people who lived there.

I think about the people who built Midnight Poutine more than I think about the site itself. They gave their time to something they believed in, in a market that made success challenging. I wasn’t able to support them the way I wanted to or the way they deserved.

I’ll come back to what happened next with Midnight Poutine in a future post. But before I do that, I want to circle back to Toronto, where blogTO was about to go head-to-head against some well-funded competition.

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We were starting to feel the constraints of our original site design. It was a bit too dark, and we needed new functionality. I hired designer Jay Delmarr to develop a new brand identity and website design. I put together the brief, information architecture, wireframes and functional specs. Jay sent back a few concepts; we refined the one I chose and handed off the final templates to a web developer named Abraham Lopez in Monterrey, Mexico.

It’s fun to look back at some of the logos and design concepts we didn’t choose and wonder what blogTO would look like today if we’d chosen a different direction.

The new design went live in June 2006. It was the first to use the red-and-white colour palette that blogTO would come to be known for. The TO in the logo was shaped like a comment bubble because we wanted to communicate that this was a community site, a place where anyone could show up, read something, and jump into the conversation. This was still a desktop-only experience, years before responsive websites existed. The header featured a rotating selection of photos of the city, enough of them in constant rotation that you’d usually see something new whenever you visited.

The redesign also introduced some features people had been asking for. You could now look up posts by author. You could sort posts by comment count, which made it easy to find whatever was generating the most discussion. And the site now supported slightly larger photos, which mattered as more people got broadband and could actually load a photo-heavy page without waiting thirty seconds.

The new design also introduced visitors to something we’d been building: blogTO was now part of Freshdaily, a national blog network with sister sites in Montreal and Vancouver that we’d launched the previous year.

In the spring of 2006, I left MacLaren McCann for Ogilvy, another advertising agency with a digital division. The work was similar, overseeing digital campaigns, but with a different client: Yahoo! Canada. blogTO was still very much a side project.

Around the same time, I’d moved in with my girlfriend, Bronwyn, into an apartment across from Venezia Bakery on Ossington. Bronwyn was a graphic designer at another ad agency during the day. In her spare time, she helped me with all sorts of miscellaneous design work for blogTO: business cards, buttons, stickers, media kits, whatever we needed on short turnaround and didn’t have the budget to pay someone else to make.

Bronwyn’s help was constant, unglamorous, and essential. blogTO was generating enough work for several full-time people, but it was still years away from hiring even one.

The team of contributors kept evolving. Some of the original members from the first year had moved on. New writers came in and took on key roles. One notable new team member was Jerrold Litwinenko, who would eventually become our second Managing Editor. It’s hard to convey how impactful his contributions were to the site during this period. Jerrold pushed us to think about community building beyond the website itself, which in 2006 and 2007 meant being active on Twitter, Facebook and Flickr. Along with popular and prolific contributor Sameer Vasta, he wrote the Morning Brew, a daily roundup of news from around the web. The format was simple: a curated selection of links and brief summaries of what was happening in the city. Other sites started emulating it. I’ve sometimes wondered whether it even inspired the Morning Brew newsletter, founded in 2015 and later sold for $75 million.

I was a big contributor to the site myself during this period. I was writing posts, taking photos, shooting video, and hosting podcasts. Without any full-time employees and little money to pay anyone, I had to wear many hats and get comfortable doing a little bit of everything. I always knew that as the site grew, I’d need to step back from the editorial side and focus more on running the business, but that was still a way off.

In the fall of 2005, we launched our first Best of Toronto poll with 50 categories. I borrowed the idea from the alt-weeklies but decided to do things differently. When I posted the first poll, I specifically called out Now Magazine for what I thought were questionable selections in their most recent poll, noting my disapproval that The Mandarin had been recognized as the Best Chinese Restaurant and Blockbuster Video had won Best DVD/Video Store.

We would do things our way. We called it “Best of Independent Toronto” to reflect that we wouldn’t recognize chains. It was a controlled poll where we put up nominations for people to vote on, and we also asked readers for their suggestions. That way, only places we thought were worthy of being recognized would be eligible to win. The Mandarin would not be among the nominees for Best Chinese Restaurant. McDonald’s would not win Best Burger. And rather than just recognizing a winner and a runner-up, we’d publish a ranked list of the top nine or ten places in each category.

We ran the polls every year, and the Best of Toronto articles became some of our most popular content. In 2009, we eventually dropped “Independent” from the name, not because we changed the focus, but because “Best of Toronto” was simpler and better for search engine optimization (SEO).

The range of what our contributors were producing kept expanding. Matt Brown was doing great work with the moviesTO podcast, our most listened-to show, where he’d talk about upcoming Toronto film events and festivals and review recently released movies. Beth Hamill, Garry Tsaconas, Mike Rotenberg, Gary Peter and others were writing concert reviews and interviewing local musicians. Megan Mooney was covering the live theatre scene. Anita Clarke was our window into local fashion. Lily Dustbin was interviewing other bloggers as part of a recurring series called The Blogerati Files. Panthea Lee connected with well-known Toronto personalities like Susur Lee in a series called Toronto Through the Eyes Of. Jay Moonah and then Rajiv Thavanathan hosted the Toronto Independent Music Podcast, a show that introduced listeners to songs from local bands. Elle Cooper and Amil Niazi teamed up on the Arts Now Podcast, where they’d interview local artists and talk about upcoming shows. Zach Slootsky, who later opened the popular Toronto restaurants The Federal and Gold Standard, was taking photos for us at concerts and parties.

The podcasts were getting up to 1,500 listens per episode. People liked the content, but we couldn’t grow the podcast audience as quickly as we were growing everything else, and there wasn’t enough podcast-specific revenue to support it. It was one area of the operation that never quite took off the way we hoped.

Then there were the sex columns. We had two contributors writing regular pieces about sex and dating, including future bartender Japhet Bower, whose posts included a guide to where to have public sex in the city and a straight man’s account of visiting a bathhouse for the first time. The articles were so popular, and we were running so many of them that we created a dedicated category called TnO to house them. We published them on Saturdays because we deemed them not safe for work.

One of our earliest viral articles was written by Ryan Couldrey, now an award-winning filmmaker. It was a first-person account of an incident at Toronto Pride where the performer Jeffree Star punched an audience member after being pelted with objects on stage, leading to Star being banned by Pride officials. Perez Hilton linked to it, sending a wave of traffic our way. The post got about 35,000 page views, which at the time felt enormous.

I’m not naming everyone who contributed during this period; there were many more than I can mention here. The team was large and growing, and I’m grateful to every person who gave their time and energy to blogTO in those early years.

Compensation for contributors was transparent but modest. I implemented a new compensation model inspired by something I’d read about Nick Denton paying Gawker Media writers based on traffic performance. Eighty percent of the site’s revenue would be paid out to contributors. The remaining twenty percent, plus whatever I was putting in from my Ogilvy paycheque, covered overhead and other costs.

We developed a point system in which each post earned a base of 3 to 5 points, with bonus points awarded based on page views. At the end of each month, total revenue was divided by total eligible points to determine a point value. One month, the site brought in $632.92 across 544 eligible points. A writer who collected 50 points that month earned $58.17.

It wasn’t much. But it was transparent, tied to performance, and ensured that everyone who contributed received something in return. The truth is, compensation was never the main reason people wrote for blogTO. The real perks were elsewhere. Contributors got media passes to concerts, film screenings and other events around the city. They got to be part of a growing community of people who genuinely cared about Toronto. They had a platform where their work was being read and discussed. And sometimes the opportunities were ones nobody saw coming.

Prior to the 2006 Toronto International Film Festival, Variety reached out to ask whether our contributors could put together a spread in their special TIFF issue highlighting favourite spots in the city for shopping, food, culture, and nightlife. I still remember some of the writers being amazed to see their photos and names appear in Variety. It was the kind of thing they were proud to show their parents, and something none of them could have imagined blogTO would have provided the opportunity to do.

Our traffic had doubled from the previous year. By the end of 2006, we had reached 50,000 unique visitors and 110,000 page views per month. But the numbers only told part of the story. I started hearing from people I’d never met at parties and events who told me blogTO was their favourite site. That they’d made it the homepage on their browser, the first thing they checked in the morning and the last thing they looked at before bed. People were tweeting that blogTO was the best thing to happen to Toronto media in years. We’d get emails from readers telling us how much they loved what we were doing.

This kind of feedback meant more to me than the traffic stats. The stats told me the audience was growing. The feedback told me we were building something people actually cared about.

By 2007, we were more organized behind the scenes. We finally had a proper set of editorial guidelines, two pages of formatting rules, and something resembling a content schedule. Film reviews went up on Tuesdays and Fridays. Concert reviews on Mondays and Thursdays.

The editorial guidelines tried to establish some standards without killing the energy that made the site work. Contributors still edited and published their own posts. The Managing Editor had the right to pull something back to draft status or modify a post, but that was generally reserved for things that violated the guidelines, duplicated something already published, or contained obvious errors.

We were clear about what we didn’t want: press releases repackaged as posts, content ripped from other sites without attribution, self-promotional hype, anything obscene or defamatory. We encouraged hyperlinking to other sites and publications. Every post needed a photo or image, original photography preferred. We asked contributors to acknowledge their sources.

We also asked writers to keep posts to around 250 words. Our logic was that shorter posts were easier to read on the web and faster to write, which meant more posts overall. We allowed exceptions for longer pieces, but brevity was the default.

My most important rule had nothing to do with word count. Everything in the city is local. Don’t write in a way that makes it sound like you had to travel somewhere to cover it. For example, never write that you “trekked” to an event on the Danforth, because you’ll lose credibility with the readers who actually live there. As far as the audience was concerned, the writer lived everywhere in the city. You only wrote about “travelling” somewhere when you were heading out of town.

We reviewed web stats regularly and identified the top-performing posts for each day of the week. About 40% of our traffic came from site referrals. Another 40% came from search engines. We paid close attention to the keywords that were driving traffic.

We had regular team meetings down the street from my apartment on Ossington, in the basement of a gallery called Interaccess that we got to use for free because I was a member. I’d get pizza from Magic Oven and beer from Amsterdam Brewery.

These meetings had become important. The team was growing fast, sometimes adding more than 10 new contributors between meetings. We needed a way to keep everyone aligned and make people feel like they were part of something, not just publishing into a void.

At each meeting, we’d introduce new team members. We’d review the latest traffic stats, and every time we met, there was a new record to report. We’d go over formatting reminders, discuss strategy, and hand out swag like t-shirts, buttons, stickers, and personalized business cards. Sometimes we’d run workshops on topics like SEO to ensure everyone understood how to write to rank higher in organic search results.

At some point we came up with a list of the types of content that we felt created value for the site: posts that sparked conversation and got linked to from other sites; regular columns that provided editorial consistency; timely news that kept the community informed; business, event listings and reviews that functioned as a long-term resource and drove search traffic; posts that built community; and contests.

Revenue was growing, slowly but steadily. We now had advertisers such as the Canadian Film Centre, Harbourfront, Arts & Crafts, the ROM, and Sony BMG, each spending between $300 and $800 on small campaigns. The National Post spent $1,000. Zipcar and Virgin Mobile each spent $2,000. The City of Toronto became a recurring advertiser. Some advertisers, like The Drake Hotel, would only do deals on a barter basis, offering us credit for food and drinks instead of paying cash. I used the credit for lunches and drinks with team members or for taking Bronwyn out to dinner.

Then we had our biggest ad buy to date: $4,500 across all three Freshdaily sites for the Mini R56 launch campaign.

In 2007, we also began a partnership with the National Post that lasted a few years. They ran blogTO content in their print edition, including Best of Toronto features, restaurant reviews and a weekly news roundup that Jerrold would write, similar to the Morning Brew. For the National Post, it was free content. For us, it was free marketing with prominent callouts to the website, introducing blogTO to a wider Toronto audience. The amount of space our content occupied in the newspaper would have cost a fortune if we’d had to pay for it as advertising.

By the end of 2007, total annual revenue across the three Freshdaily sites was just over $65,000. It had taken three years to get there. blogTO was real and growing, but it was still a long way from sustaining itself.

In the summer of 2007, we launched our printed neighbourhood maps. The idea came from similar guides I’d encountered while travelling in Buenos Aires and Mexico City. Ours initially covered four areas: West Queen West and Liberty Village, Parkdale and Roncesvalles, Leslieville and Riverside, and Little Italy and Dundas West.

The maps were highly curated guides to each neighbourhood, printed on recycled paper. We distributed them for free at local cafes, restaurants and shops. We didn’t charge businesses to be included, but we offered them the opportunity to pay for more prominence. Hotels put them in guest rooms. Realtors requested copies for open houses. For a modest shipping fee, people could order a complete set online. We got orders from across Canada, the U.S., Mexico and overseas from people planning trips to Toronto.

This was the same summer that the first iPhone was released. Google Maps was still a few years away from being something everyone used on their phone. A well-designed printed map of a neighbourhood, with curated recommendations from a trusted site, was genuinely useful.

Creating, distributing and replenishing the maps was hard work. I did all the door-to-door sales and distribution myself. Bronwyn put up with the extra boxes we kept in our apartment so I could do second and third waves of distribution when cafes and shops ran out. The maps were mostly a breakeven proposition, with modest profits in good years. But their real value was as a marketing tool. They built brand awareness, connected us with local businesses, and reinforced blogTO as a brand that helped people discover new places and get to know their city better.

In 2007, we held our first IRL event during the Contact Photography Festival. For the Constructed Image, we partnered with Toronto photobloggers and asked 15 of them to submit one image depicting their vision of the city. We printed them out and held an opening party at Brassaii on King West. We were also sponsoring other local events to get our brand in front of people in the real world.

Around the same time, we were getting recognition. Backbone Magazine named blogTO one of the “Top 20 Web 2.0 Pioneers in Canada.” Forbes included us in their Best of the Web list.

Before the end of 2007, we embarked on our third logo and website redesign in three years. This one was done by Mark Holden, a colleague of mine from Ogilvy. We removed the comment bubble from the logo and leaned into the Web 2.0 design aesthetic that was popular at the time. The site got a more detailed directory section for places like bars and restaurants, making it easier for users to search by category, cuisine and neighbourhood, with Google Maps integration. The event listings section became more robust, with a date picker.

In June 2007, I presented at Casecamp, part of a wave of “unconferences” that were taking place across Toronto’s tech community, alongside events like DemoCamp, PodCamp and TransitCamp. I introduced the audience to the Freshdaily Network, describing it as “hyper-local arts, music, film, fashion, food and news, in Vancouver, Toronto and Montreal.” I talked about what we’d built: over 18,000 podcast downloads a month, 23,000 reader comments and more than 1,000 Flickr group members.

I presented a theory that was getting traction at the time: that we were entering a “blog 2.0” era defined by more sophisticated websites that would make the first generation of blogs look dated. We’d just completed our third redesign and introduced features not typically associated with blogs: a restaurant directory and robust event listings. blogTO had started as a blog, and the name said as much. But it was becoming something else. Something closer to what I’d imagined when I’d worried the name might be too limiting.

And then Ogilvy let me go. My boss had changed, business was slow, and I suspected they knew I was distracted by blogTO. It turned out to be the best thing that could have happened. blogTO was consuming more and more of my time, and I reached a point where it was unsustainable to keep working full-time at an agency while also doing what I needed to keep growing the site. I got one month’s severance. That night, Bronwyn and I went out for drinks at The Embassy in Kensington Market to celebrate.

The next morning, for the first time in three years, blogTO wasn't a side project. It was the whole thing.

It wasn’t glamorous. But every month the numbers went up. Every month, the team got bigger. Every month, there were more advertisers, more readers, more comments, more evidence that this thing was turning into something the city actually needed.

The next chapter of the story is about what happened when we tried to replicate it in Montreal and Vancouver. That’s for the next post.

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I was assigned to a single client, one of the agency’s biggest: Microsoft. This was three years before the iPhone, and Microsoft owned the PC and office productivity software spaces. Apple was gaining momentum with the iPod and had launched retail stores, but was still tiny in comparison. But Apple was turning into a brand that resonated with consumers in ways Microsoft didn’t. We all told our client they should watch out for them. They laughed it off, dismissing them as a niche competitor.

Having decided not to continue with Navigate the Streets, I was looking for my next entrepreneurial thing. I knew I didn’t want to live the corporate life in the advertising world forever. Blogs had started to become big in the digital space. A lot of people used Blogger or LiveJournal for personal musings, but there was also a growing collection of professional blogs, part of a new wave of digital media companies.

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I was inspired and influenced by what was happening in New York. Nick Denton had launched Gawker in 2002 and was building Gawker Media, a network of blogs covering gossip, technology, sports, and politics. Lockhart Steele had started Curbed, a real estate blog. Jason Calacanis was assembling Weblogs Inc., a portfolio of niche blogs he’d later sell to AOL. Jake Dobkin and Jen Chung launched Gothamist, a New York City blog, and had already started building a network of local sites with the same template and tone.

Blogs were becoming a significant part of my media diet. They were fun to read and less constrained than magazines and newspapers. The economics were different, too. You didn’t need printing presses or distribution trucks. You needed a blogging platform, a point of view, and enough passion and perseverance to keep going.

Toronto didn’t have anything like what was happening in New York. There were some smaller Toronto blogs that touched on the city. Marc Weisblott, a local journalist, had a blog called Better Living Centre. Rannie Turingan was a popular photoblogger who ran GTA Bloggers. But there was nothing with the scope or ambition to cover the city the way it deserved to be covered.

At the same time, traditional media in Toronto was pulling back from exactly the kind of coverage that made a city feel like a city. Both the Toronto Star and Globe & Mail had recently scaled back on Toronto lifestyle and culture coverage. They also weren’t doing much of anything online. And there was an obsession across news media with leading on negative stories: crime, murder, hard news. The Toronto I read about in newspapers didn’t reflect my day-to-day experience of actually living here, or what I felt most people around me cared about.

The alt-weeklies were a different story. Now Magazine and Eye Weekly were still the go-to publications for anyone who wanted to know what was happening in Toronto. They had event listings, restaurant reviews, arts coverage, film and music roundups, and nightlife. If you were a certain age and lived in Toronto, you picked up one or both of them every week. They were free, they were everywhere, and they had the audience and the advertisers that came with being the default source for local culture.

But they were also complacent. Both publications were making serious money from their print editions, which included thick classified sections and pages of personal and sex ads at the back. Their websites were afterthoughts. They published once a week. The internet was reshaping how people found and consumed local information, and Now and Eye didn’t seem to be paying attention.

I looked at all of this, and the opportunity seemed obvious. The blogs coming out of New York were proving the model. There was a gap in Toronto’s digital landscape. The alt-weeklies were sitting on their hands. More and more people were consuming content online. The blogging platforms had eliminated the barriers to entry. Someone was going to start a digital publication for Toronto.

I decided that someone would be me.

I chose Movable Type as our blogging platform because many of the most popular professional blogs were using it at the time. It turned out to be one of my first mistakes, and we’d eventually rip it out and replace it with a custom CMS, but in the fall of 2004, it seemed like the right call.

I needed a name and a team. I started reaching out to people in Toronto I respected who were doing interesting work at the intersection of culture and media. I invited them to the party room on the top floor of my condo building on Charlotte Street, in what was then known as Toronto’s Club District. The pitch was straightforward: there’s an obvious gap in Toronto’s digital media landscape, here’s what’s happening in New York, we should build something like this here.

Everyone at the meeting recognized the opportunity. The problem was that most of them wanted to do their own thing. Matt Blackett and Shawn Micallef of the recently launched Spacing Magazine were there. I wanted them to join me, but they were committed to Spacing. I had some notoriety among this group for having won the best local blog award from Eye Weekly for Navigate the Streets, which was sort of a joke since it wasn’t really a blog about Toronto. But I worked in digital advertising and understood how the business model would need to function. That was my real credential.

We discussed names at the meeting. People liked blogTO, though I had reservations. Not because I thought blogs were a passing fad, but because I could see this growing into a larger media company and didn’t want the name to pigeonhole us as just a blog. But everyone liked the “TO” element. Toronto didn’t yet have the habit of appending TO to everything, as it does now, so it felt fresh. I think we can claim some credit for starting that trend.

Many talented web designers worked with me on the Microsoft account at MacLaren McCann. I asked two of them, Chris Halminen and Petar Stoilov, to help me with the design. Petar created the logo. Chris did the web design.

I don’t remember exactly what I paid them, but it wasn’t much. The first version of the site featured a white logo on a black-and-grey background. There were rotating taglines: “Cuz we don’t live in Tokyo or LA” and “Cuz we don’t live in Geneva or Jerusalem.” They were simple statements of intent. We wrote about Toronto because that’s what we knew and where we lived. We discontinued the taglines a year later.

Then, about a month before we were set to launch, I found out that Gothamist had expanded to Toronto with a site called Torontoist. Plans for blogTO were already well underway, so nothing changed. But it meant we’d have competition from day one.

I pressed ahead.

blogTO launched on December 13, 2004. The first post was written by Timothy Comeau and titled “Vs. at the Latvian House.” It was a review of a local film screening at 491 College Street. Not exactly the kind of thing that screams future media company, but it was a post, it was live, and the site was real.

Aside from Timothy and me, the initial team consisted of Christine Miguel, Darius Byrne, Deirdre Swain, Jennn Fusion, Justyna Lorenc, Lars Paronen, Matt Alexander, Paul Fler and Catherine Farquharson.

We had an RSS feed, because RSS readers were how serious internet users kept up with their favourite blogs in 2004. And we had a comment section on every article, which would turn out to be one of the biggest reasons people kept coming back.

The site was organized like the sections of an alt-weekly. Food, Arts, Music, Film, Fashion, Sports. We also had a section for Podcasts. In our first year, we launched a film podcast, an indie music podcast, and an arts podcast. There was a video section too, though it was rarely populated, just the occasional clip we’d shot at a local event on whatever camcorder model was popular at the time.

Our original crew was 10 contributors, each with their own beat, each doing this almost entirely as a passion project. There was no set posting frequency, no comprehensive style guidelines, no editorial standards document and no copy editing. Everyone had their own CMS login and published whenever they felt like it. Nobody, including me, ever knew what was going up on a given day. A post might appear at 9 a.m., 11 p.m., or not at all. It was chaotic in a way that would horrify anyone who’s ever run a real newsroom, but it also gave the site an energy that felt spontaneous and authentic. You never knew what you’d find when you visited blogTO, and neither did we.

It wasn’t until June 14th, six months after launch, that I posted something formally introducing our team and what we were doing. The description was deliberately loose: “blogTO is a blog about Toronto. We cover music, film, the arts, bars, restaurants, people, places and an assortment of random but hopefully interesting things happening in the city we call TO. This is a blog. We invite you to post comments, disagree with us, flatter us and otherwise tell us what you think.”

That last part was important. The comment sections became communities. People argued about restaurants, bands, and neighbourhoods. They had opinions about everything, wanted to share them, and argued with other people’s opinions. The comments gave the site a sense of life that the posts alone wouldn’t have.

Growing the team wasn’t difficult, which surprised me. We offered minimal to no pay at the beginning, and people still wanted in. The appeal was a combination of things. People wanted to belong to a community. They liked having a platform where they could write about whatever interested them without someone editing the personality out of their work. The site was growing fast enough that contributors could see their work being read and discussed. For some, blogTO was a stepping stone, a place to build a portfolio and a byline that might lead to better-paying work somewhere else. For others, it was just fun to be part of something that felt new and different, something the city hadn’t had before.

By the end of the first year, we were pulling in 28,000 unique users and 300,000 page views a month. We’d grown from 10 contributors to 18 and had added an event listings section. The roster included some people who’d go on to do unexpected things. Stephen Amell was one of our contributors. At the time, he was an aspiring actor living in Toronto. He later moved to Los Angeles and became well known for his role as Oliver Queen in the superhero series Arrow. Jenny Yuen was another early contributor who went on to become a respected reporter at the Toronto Sun. Tanja-Tiziana Burdi came on board as our first Managing Editor, giving the operation the structure it desperately needed.

Meanwhile, I was still at MacLaren McCann during the day, overseeing digital advertising campaigns for Microsoft, then came home to work on blogTO at night and on weekends. The site had a traditional media monetization strategy from launch. We ran advertising, aiming to grow the audience large enough to attract advertisers and deliver enough page views and impressions to make the model work. I understood this well because I was living it professionally. I spent my days managing digital campaigns for one of the world’s largest companies and working closely with the media-buying team on ad placements for clients that an agency like MacLaren McCann represented. In the evenings, I was trying to build the kind of site those same types of clients might eventually want to advertise on.

The challenge was that we needed scale, and scale takes time. You can’t sell meaningful advertising against a site that gets a few hundred visits a day.

In the early days, we used Google AdSense to backfill our unsold ad inventory. I still remember the day our first revenue cheque from Google arrived in the mail for $75.36. It wasn’t life-changing money, but it was proof the model could work. I took Bronwyn out for dinner to celebrate.

We still needed to grow. We needed more content, more contributors, and more reasons for people to come back every day instead of once a week. The alt-weeklies had spent decades building their audiences. We were trying to do it faster, bootstrapped on my own savings and pay cheques from my day job.

The competition with Torontoist was immediate. People in Toronto’s media and blogging circles quickly framed it as a rivalry. Readers chose sides. You were a blogTO reader or a Torontoist reader, the same way people were a Now reader or an Eye reader. It would take years for the outcome of that competition to become clear.

But Torontoist wasn’t what kept me up at night. Now Magazine and Eye Weekly were the real benchmarks. That’s where everyone in Toronto went for the kind of information we were producing: event listings, restaurant reviews, arts coverage, things to do this weekend. They had the readership and the advertising revenue, and we’d need both to turn blogTO into a real business. I knew there was an opening because I could see what they weren’t doing. They were committed to weekly print schedules while we published daily. They treated their websites as afterthoughts while the web was our entire existence. They were protecting a legacy business model while we had nothing to protect and everything to gain.

I wasn’t worried about the other digital competitors. They didn’t have the audience or the advertisers. The fight that mattered was against the incumbents, and the incumbents didn’t seem to realize they were in one.

One day, a headhunter called. Torstar Digital was unhappy with Toronto.com’s performance and was looking for someone new to run it. Was I interested? I took the meeting. I listened. Then I told them I was going to stick with blogTO. I don’t think they saw blogTO as a serious competitor at that point. They certainly didn’t know I thought Toronto.com was a waste of a great domain, or that making it irrelevant was part of my plan.

On December 5, 2006, a package arrived in the mail from Now Magazine. Inside was a letter and a window decal congratulating blogTO on winning the Readers’ Choice Award for Toronto’s Best Blog.

I read the letter. Now Magazine, the publication whose audience and advertisers we were going after, was congratulating us.

By the end of the first year, blogTO was still small. Still scrappy. Still a side project I ran from my apartment while working a full-time job at an ad agency. We had a team of writers who genuinely loved Toronto and wanted to write about it. We had a comment section that people treated like a town square. We had a monetization model that I understood from my day job. And we had the single biggest advantage any upstart can have: the incumbents weren’t paying attention.

For now, it was enough to know that the thing I’d started in the party room of a condo building on Charlotte Street was becoming something real.

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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.

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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Urban Challenge was already in many U.S. cities, but it wasn't in Canada yet. I thought I could create a version in Toronto. But first, I wanted to see how it actually worked.

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My girlfriend, Bronwyn, and I hadn’t travelled together yet. I suggested Seattle for our first trip. We could do the Urban Challenge race and stay with a friend who had moved there from San Francisco.

Neither of us had been to Seattle before. It was late August 2003. The weather was beautiful. We walked the city, hit some bars and restaurants. There was a huge rally for Howard Dean that weekend. Thousands of people showed up. He was running for the Democratic presidential nomination and looked like he might actually win. It was peak Howard Dean, before the scream incident. The energy was incredible.

We showed up on race day. About 250 people were competing. I can’t remember where we placed but it wasn’t near the top. We had fun, though. More importantly, I saw how the race actually unfolded, and how many clues and checkpoints made sense, and what the organizers did before and after the race. I also got a feel for what it was like to compete as a participant, what worked and what didn’t. I took detailed notes on it all.

When we got back to Toronto, I was confident I could create an Urban Challenge of my own.

I didn’t wait. I set a race date for October and moved fast. I built a website with help from former Agency.com colleagues, and secured sponsors. All proceeds would go to the Make-A-Wish Foundation, my father’s favourite charity.

I called it The Experience Running Project.

I tried to keep costs low. Steam Whistle donated the Roundhouse as the venue. I bought digital cameras to lend to participants since smartphones didn’t exist yet, figuring I’d spread the cost over future races. I paid for race bibs, rented a race clock, and hired a DJ. Bronwyn and some of my friends volunteered as staff. I ordered food from local restaurant Jumbo Empanadas to go with Steam Whistle beer for the post-race celebration.

For promotion, I made flyers and distributed them around the city, and submitted the event to free listing sites. But the real boost came from media coverage. CBC did a TV segment. The Toronto Star wrote an article comparing it to Urban Challenge.

75 teams signed up.

Just before race day, I noticed a flyer for something called City Chase. It was a similar concept. I did some digging and figured out the two people who were behind it. Then I noticed they’d signed up for my race. They were doing research, just like I’d done in Seattle. After they finished, I introduced myself. I asked if they’d had fun and wished them luck with City Chase, which was scheduled for a few weeks later. They seemed surprised I’d figured out who they were.

Race day was exciting. The DJ was spinning music at the Roundhouse. There was good pre-race energy. The venue was nontraditional for a running race, which made it feel unique. People were curious and excited to see what this would be like. It was a good mix of participants. There were some runners, and some people who were clearly not runners but who I imagine thought they could be competitive in a race that relied as much on solving clues as on speed.

The race generated about $1,000 in proceeds. I wrote a cheque to Make-A-Wish.

It seemed easy enough to repeat. The next summer, I decided to go national. Nine cities across Canada. Winners from each city would get a trip to Montreal to compete in a championship for $10,000. Top teams from each city would be invited to compete, but only the winners would get free flights and hotel rooms. I got national sponsors like Vonage and Monster Energy. I found a hotel in Montreal to donate rooms, and secured venues in each city willing to host in exchange for sponsorship.

Then I made my biggest mistake.

I rebranded to Navigate the Streets. I thought it was a better name. I spent money on a new logo and website, but I threw away all the momentum from The Experience Running Project including the press coverage, the name recognition, and maybe some of the participants who might come back. All of this was gone because I wanted a different name.

I also had no local knowledge of most of these cities. I’d never been to Halifax, Ottawa, Winnipeg, Edmonton or Calgary before. I had no connections there, no sense of the market, and no local staff or volunteers to help me execute the races.

I spent money on flyers, Google search ads, online banners and print ads in alt-weeklies in each city. Now Magazine in Toronto. Fast Forward Weekly in Calgary. The Georgia Straight in Vancouver. It didn’t translate to enough sign-ups. Press coverage wasn’t as good either. The Toronto Star and CBC had already covered the event the year before. They weren’t interested again. I did get coverage from Explore Magazine, the Winnipeg Free Press, and the Globe and Mail, complete with a photo of me holding a cellphone and a map outside Union Station in my brand-new Navigate the Streets t-shirt.

Toronto numbers stayed flat. About 25% of participants from the year before came back. Vancouver's numbers were slightly lower than Toronto's. Calgary, Ottawa, Edmonton and Winnipeg weren’t great. Halifax and Quebec City numbers were so low that I cancelled the events. People who showed up still had fun, but the races felt much smaller than Toronto. I was embarrassed by the turnout. Even with ineffective marketing and low press coverage, I still thought more people would register through word of mouth.

I was losing money, and I still had to pay for the winners to fly to Montreal and compete for the $10,000 prize.

Before the championship, I sent everyone their flight and hotel details. I also told them I was lowering the prize to $1,000. I couldn’t afford more. People were disappointed but understanding. A free weekend in Montreal and the chance to compete again and be recognized as the national champion still had a lot of appeal.

The other problem was City Chase. They’d also gone national, hitting almost all the same cities, sometimes twice. They had sponsors like The Running Room, who would market the event to their huge database of runners. They promoted the event at other running events in each city.

After that summer, I was done. Navigate the Streets had been a lot of work, and I was feeling defeated. Having to cut the prize amount in Montreal was embarrassing.

Navigate the Streets taught me things I needed to learn.

Execution matters. The concept was simple. What mattered was whether I could pull it off. First year in Toronto, I did. Second year, trying to scale, I didn’t.

Rebranding threw away momentum for no good reason. This lesson stuck with me. Years later, when I was running blogTO, people would occasionally suggest rebranding. blogTO wasn’t a perfect name. But I remembered what happened when I rebranded The Experience Running Project. There are real costs to rebranding, even when you think a different name sounds better.

Local knowledge matters. I knew Toronto and Montreal. I’d been to Vancouver before. I didn’t know the other cities.

Competition changes the equation. Year one, I was first. Year two, City Chase was doing it better. Navigate the Streets was no longer unique.

But the most important thing: I liked building things. Even when it failed, even when I lost money, it was still a fun experience. People showed up and had a good time because of something I created. That mattered.

One more thing: I’d added a blog to the Navigate the Streets website. I posted updates all summer, photos and highlights from different cities. When Eye Weekly ran their Best of Toronto Readers’ Choice poll that year, I submitted it for best local blog. I asked my friends to vote. It won. They sent me a plaque, which I still have in my home office.

It reads: 'Navigate the Streets - Toronto’s best local blog.'

A few months later, I’d start blogTO.

I needed to get to San Francisco, the epicentre of the dot-com boom. But how?

Someone at my company had the idea of starting an internet group to figure out how we could add web-related offerings to the firm’s portfolio. E-commerce, online stores, that kind of thing. I volunteered immediately. This let me build internet knowledge and skills on my resume. Meanwhile, the company got bought by PwC, so now I also have the brand of a top-five consulting firm on my CV.

I started applying for jobs in San Francisco. When I’d talk to hiring managers, I’d tell them I’d be in San Francisco in a few weeks and ask if I could schedule an interview. I realized it would be easier for them to say yes if I’d already committed to coming to the city. It worked. I ended up getting interviews with companies that had names like Sapient and Razorfish.

I accepted a position with Agency.com. I didn’t have a U.S. work visa, but they agreed to sponsor me under the H-1B visa programme. I packed up my car and headed for San Francisco.

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I ended up living with three roommates in Hayes Valley. All my roommates had full-time jobs at internet companies and dabbled as DJs on the side. To fit in, I immediately purchased a pair of Technics SL-1200 turntables and a mixer.

My job title was “Strategist,” and I worked alongside information architects, front-end designers and web developers to create websites and web applications for Agency.com’s roster of clients. My first project was to create a website for Openwave, the company formed by the merger of Phone.com and Software.com. They made the software that powered messaging and browsers in pre-iPhone mobile phones. You can guess how that business turned out.

For another project, I worked with Visa on an animated logo and sound that would play whenever someone completed an online transaction using a Visa card.

Living in San Francisco was fun. Almost every other night, I’d end up at some sort of party for a dot-com company. Free food, free drinks, people talking about their stock options like they were already millionaires. I could order groceries to my apartment using Webvan or Peapod. I could rent movies from Netflix, and DVDs would arrive in the mail. Bike couriers clad in bright orange were all over the city delivering snacks for Kozmo.com, the short-lived Uber Eats of its time.

The money was everywhere. Companies were burning through it faster than they could raise it. Nobody seemed concerned. The conventional wisdom was that you had to grow fast, that profitability could wait, that whoever captured the most market share first would win everything.

I remember going to parties where people would talk about their companies like they were building the future. And they believed it. The internet was going to disrupt everything.

Looking back, it’s easy to see how delusional this all was. But when you’re in it, when everyone around you is saying the same things and the stock market keeps going up, it doesn’t feel delusional.

I enjoyed my job at Agency.com. The work was interesting. I was learning about web development, information architecture, and user experience design. I was working with smart people.

I also took a continuing education class on sales at Stanford. Every week, I’d drive down to Palo Alto for the night class. I’d see Google employees around campus. I considered asking whether they needed someone to help set up Canadian operations. But I never did. I was happy where I was.

And then the bubble burst.

It didn’t happen all at once. It started slowly, with a few companies running out of money and a few stocks dropping. Then it accelerated. By early 2001, it was clear that something fundamental had broken. The venture capital dried up. The IPO market disappeared. Companies that had been valued at hundreds of millions of dollars were suddenly worth nothing.

At first, Agency.com had a small wave of layoffs. A few people, nothing dramatic. We all told ourselves it would be fine. The company had real clients. We weren’t burning through cash with no business model. We’d survive this.

A few months later, we were all called into the lunchroom and told that Agency.com was shutting down its San Francisco office. We should pack up our things. We were all immediately out of a job.

We were shocked. We’d known things weren’t great, but we hadn’t expected this. We all headed to a nearby bar and talked about how quickly everything had turned. People were trying to figure out what came next.

For me, it was simple. I had to leave San Francisco. There were no jobs, and my work visa had expired. The city that had felt like the centre of the universe six months earlier now felt different. Everyone was either leaving or desperately trying not to. The parties stopped. The bike couriers in orange disappeared.

A friend of mine came from Toronto to meet me. We spent two weeks driving across the country until we got back. He was about to get married. I wasn’t sure what to do next.

I briefly flirted with the idea of getting work overseas. I got a job offer from a mobile consulting startup in Singapore that liked that Openwave had been my client. I interviewed for Deloitte in Auckland.

Ultimately, I decided to travel instead. I spent a couple of months learning Spanish in Antigua, Guatemala. I was in Quito, Ecuador, on 9/11. I took the GMAT in Buenos Aires and considered an MBA at NYU, Columbia, or Kellogg. I spent a few weeks learning to kite surf in Tarifa, Spain. I got my CFA Level 1 while living in Barcelona for a brief time. I was trying to figure out what came next.

I eventually returned to Toronto and got a job. I also explored the idea of starting a non-profit water company. I drove down to New York to meet someone at Balthazar who worked for Keeper Springs, Robert F. Kennedy’s bottled water company, which was doing something similar. Nothing came of it.

The San Francisco experience taught me something. Hype and reality can diverge dramatically. When they do, the correction is brutal. The internet did change everything, but not in the exact ways everyone expected, and not on the timeline people thought.

I also learned that I wanted to build my own thing.

I’m glad I went to San Francisco. I’m glad I got to see the dot-com boom up close. I’m glad I was there when it all fell apart. You learn more from failures than successes.

What came next was Toronto. And eventually, building something of my own, but it wouldn’t be blogTO just yet. Instead, I’d start an Amazing Race-style running race called the Experience Running Project.

This was three years before AOL bought Time Warner, the owner of CNN, in what is still widely seen as the worst business deal in history. Back then, CNN had a sterling reputation and was the unquestioned worldwide leader for breaking news.

I was hired to work in the PR department on the 19th floor. My primary job was to read through a stack of newspapers each morning and physically cut out any article that mentioned CNN. It was two hours a day with scissors and newsprint. The clippings were filed in folders and given to my boss, who passed along anything interesting to her boss. It was the kind of work that would eventually be automated.

On my third day, I wandered down to the 18th floor, where CNNfn was based. CNNfn was CNN’s dedicated financial news channel, now called CNN Business. They filmed live all day. There were cameras, lights, and producers with clipboards. It was considerably more interesting than the 19th floor.

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I started spending most of my time down there.

CNNfn had a show called “It’s Only Money” that featured young entrepreneurs building dot-com businesses. It was mostly people in their twenties who had started e-commerce sites and had theories about how the internet would change everything.

I was given the job of pre-interviewing the guests. I’d call whoever was scheduled to appear and ask about their business and their background. I’d take notes and pass them to my producer and host so they’d know what to ask during the live segment.

It was the closest thing to journalism I’d ever done, and I found it thrilling. You’re trying to figure out whether someone will be interesting on camera. You’re looking for the specific details and stories that make a segment feel real rather than rehearsed. Most guests were happy to talk. They were getting free airtime on CNN to promote their startups. They didn’t care that I was an intern.

I don’t remember most of the companies or founders. They’ve blurred together. A few probably survived what came next, but most definitely didn’t.

I made one notable mistake. I pre-interviewed a guest whose business was interesting but who was painfully dull on the phone. His voice was monotone, he had no energy, and his answers went nowhere. I should have flagged this for my producer. I didn’t. The segment aired, and the guest was a disaster. There were awkward pauses, one-word answers, and the host struggled to salvage it.

The producer asked me afterwards if I’d picked up on this during the pre-interview. I froze. Either answer was bad. If I said yes, I should have warned him. If I said no, I was incompetent at the one task I’d been given. I mumbled something about not having noticed. I don’t think he believed me.

At the end of the summer, I found out they were cancelling the show. The producer lost his job. I still wonder if this was partly my fault.

On the 20th floor, Lou Dobbs filmed “Moneyline,” the flagship business show that had made him one of the most recognizable faces at CNN. Dobbs had the kind of casual authority that came from being really good at your job and knowing everyone knew it. I was intimidated by him. He had no idea I existed.

Larry King also filmed at 5 Penn Plaza. He was someone who’d built a career on being curious and letting famous people talk. He was good at it. His questions sounded simple, but gave people room to say interesting things.

The elevators at 5 Penn Plaza were always interesting. The building’s hierarchies temporarily dissolved in there. I’d ride up with producers, hosts, executives, and other interns, and occasionally with someone famous who was there for an interview. The unspoken rule was to pretend not to recognize famous people. Everyone acted like it was normal to share an elevator with someone who’d been on a magazine cover or run a Fortune 500 company.

I rode the elevator with Donald Trump on July 23, 1997. He was there for Larry King. He didn’t talk to anyone. We all pretended not to notice him. You can still read the transcript of the interview online.

I didn’t think much of it at the time. Trump was famous for being famous. In 1997, that meant he was famous for having money, putting his name on buildings, and occasionally going bankrupt and recovering. He wasn’t politically relevant. He was a tabloid fixture, someone who’d married models and built casinos and had a cameo in “Home Alone 2.” The idea of him becoming president would have seemed ridiculous.

The other celebrities I saw in elevators have faded from memory. There were lots of them. 5 Penn Plaza was a high-traffic spot for anyone doing media in New York, and Larry King’s guest list was eclectic. I maintained my policy of studied nonchalance. I never tried to start conversations and never asked for autographs. I treated famous people like they were regular people who happened to be in the elevator, which is probably what they wanted.

The internship was unpaid, which was standard for the industry and completely unsustainable unless you had a second job or, in my case, a cousin with a spare bedroom. The apartment was small and overlooked a highway, but it was free, and I was grateful for the place to stay and the opportunity to experience a full summer in New York.

There was one unexpected perk at CNN. Boxes of review copies from book publishers were always lying around the office, sent to various shows in the hope of coverage that would almost certainly never happen. The books were free to take, so I started taking them.

Barnes & Noble had a generous return policy in 1997. You could bring back books without a receipt and receive store credit equal to the cover price. I realized that this policy, presumably designed for unwanted gifts, worked equally well for free review copies acquired from a CNN internship.

I got strategic about it. I’d rotate between different Barnes & Noble locations around Manhattan, never hitting the same one twice in a row, walking in with a stack of hardcovers and walking out with store credit that I’d immediately spend on whatever I actually wanted to read. I must have visited every Barnes & Noble in the city that summer. This was before Amazon reshaped the book business, when bookstores were still everywhere.

I read more that summer than any summer since.

My time at CNN ended because I didn’t have a work visa. I returned to Toronto and landed a job at a consulting firm specializing in implementing SAP software for clients like Nokia, Panasonic and JVC. SAP is enterprise resource planning software, which is a boring way of saying it’s the plumbing that makes large corporations function. It was technical and tedious, but paid way better than any media job would have.

I was competent at it. Not passionate, but competent. The work was project-based: several months embedded with a client, long hours, then on to the next one.

I kept thinking about CNN, but not because the internship had been glamorous. I thought about it because it was the first time work had felt interesting. Calling entrepreneurs, figuring out whether they’d be good on camera, looking for the details that made a story worth telling. That had engaged me in a way that enterprise software never would.

I didn’t know yet that I’d end up back in media or that I’d start a publication and spend two decades building it.

CNNfn no longer exists. Lou Dobbs went on to become a far-right commentator before CNN cut ties with him. Larry King continued his show for another 13 years. We all know what happened to Donald Trump.

And I went back to Toronto, worked in enterprise software, and then moved to San Francisco just as the dot-com boom was getting overheated.

That’s the story for the next post.