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.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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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.