{"id":90300,"date":"2026-10-14T10:34:18","date_gmt":"2026-10-14T14:34:18","guid":{"rendered":"https:\/\/paulsyng.com\/blog\/?p=90300"},"modified":"2026-10-14T10:38:06","modified_gmt":"2026-10-14T14:38:06","slug":"tim-shores-wild-account-of-how-blogto-was-built-scaled-and-sold-for-15-million","status":"publish","type":"post","link":"https:\/\/paulsyng.com\/blog\/tim-shores-wild-account-of-how-blogto-was-built-scaled-and-sold-for-15-million\/","title":{"rendered":"Tim Shore&#8217;s wild account of how blogTO was built, scaled, and sold for $15 million"},"content":{"rendered":"\n<p class=\"wp-block-paragraph\">When Tim Shore sat down with me for <a href=\"https:\/\/www.youtube.com\/watch?v=4CcnT1r1868\" target=\"_blank\" rel=\"noopener\">Episode #31 of the podcast<\/a>, we opened with a screenshot of the LinkedIn post that shocked Toronto\u2019s media scene: after a 20-year run, Tim had been fired from blogTO and ZoomerMedia, the very company he founded and built from scratch.<\/p>\n\n\n\n<figure class=\"wp-block-embed is-type-video is-provider-youtube wp-block-embed-youtube wp-embed-aspect-16-9 wp-has-aspect-ratio\"><div class=\"wp-block-embed__wrapper\">\n<iframe loading=\"lazy\" title=\"#31 Tim Shore \u2014 How blogTO Was Built, Scaled, and Sold\" width=\"500\" height=\"281\" src=\"https:\/\/www.youtube.com\/embed\/4CcnT1r1868?feature=oembed\" frameborder=\"0\" allow=\"accelerometer; autoplay; clipboard-write; encrypted-media; gyroscope; picture-in-picture; web-share\" referrerpolicy=\"strict-origin-when-cross-origin\" allowfullscreen><\/iframe>\n<\/div><\/figure>\n\n\n\n<p class=\"wp-block-paragraph\">As we unpacked it over nearly two hours, we found a poetic bookend beneath that announcement. Tim\u2019s full-time journey with blogTO started when he got fired from his agency day job at Ogilvy, walked out with four weeks of severance, and bet on himself; two decades later, it ended the same way, with a $15 million acquisition in between.<\/p>\n\n\n\n<p class=\"wp-block-paragraph\">During our conversation, Tim shared the overarching philosophies that allowed a bootstrapped side hustle to outlast well-funded competitors and legacy media giants: putting the reader first, refusing to let advertisers buy their way onto &#8220;Best of Toronto&#8221; lists, failing fast on new platforms, and optimizing for audience growth over short-term revenue.<\/p>\n\n\n\n<p class=\"wp-block-paragraph\">Shortly after our episode aired, Tim launched a Substack to document the entire 20-year history of blogTO in long form. While our podcast conversation captured the high-level strategy and mindset, Tim\u2019s written series opens the vault on the specific numbers, boardroom negotiations, lawsuits, culture clashes, and behind-the-scenes chaos he couldn&#8217;t fully cover on the mic.<\/p>\n\n\n\n<p class=\"wp-block-paragraph\">If you listened to our episode, consider this the director\u2019s cut \u2014 connecting the lessons from our conversation to the wild, granular details Tim has been sharing on his Substack.<\/p>\n\n\n\n<h2 class=\"wp-block-heading\"><strong>1. The Charlotte Street Pitch, a $75.36 Cheque, and the &#8220;Local&#8221; Rule<\/strong><\/h2>\n\n\n\n<p class=\"wp-block-paragraph\">On the podcast, Tim explained how he started blogTO in late 2004 while working in digital advertising at MacLaren McCann (handling Microsoft) and later Ogilvy (handling Yahoo!). At the time, digital portals like toronto.com had such a poor reputation that industry insiders called it &#8220;toronto.wrong,&#8221; and print alt-weeklies like <em>Now Magazine<\/em> and <em>Eye Weekly<\/em> only published once a week on street corners. Tim saw the opening, used free gallery basements at InterAccess on Ossington for team meetings fueled by pizza and $25 cases of Amsterdam Brewery beer, and pulled off guerrilla marketing stunts like syndicating columns in the Saturday <em>National Post<\/em>, printing physical neighbourhood maps, and mailing out &#8220;Best of Toronto&#8221; window decals.<\/p>\n\n\n\n<p class=\"wp-block-paragraph\">In his first two Substack posts, Tim reveals the exact mechanics of how those early days came together:<\/p>\n\n\n\n<p class=\"wp-block-paragraph\"><strong>The Condo Party Room Pitch:<\/strong> Before blogTO, Tim had been winding down an earlier project called <em>Navigate the Streets<\/em>. In the fall of 2004, looking to replicate the energy of New York blog networks like Gawker and Gothamist, he invited local culture and media figures, including <em>Spacing Magazine<\/em>\u2019s Matt Blackett and Shawn Micallef, to the top-floor party room of his condo on Charlotte Street to pitch a new Toronto publication. Most wanted to do their own thing, so Tim forged ahead, tapping two MacLaren McCann colleagues, Petar Stoilov and Chris Halminen, to design the first logo and website.<\/p>\n\n\n\n<p class=\"wp-block-paragraph\"><strong>A Chaotic Launch and Famous Alumni:<\/strong> Just a month before launch, Gothamist expanded to the city with <em>Torontoist<\/em>, meaning blogTO had a direct rival on day one. blogTO officially went live on December 13, 2004, featuring rotating taglines (<em>&#8220;Cuz we don&#8217;t live in Tokyo or LA&#8221;<\/em>) and an inaugural post by Timothy Comeau reviewing a film screening at the Latvian House on College Street. The original 10 contributors had their own CMS logins and could publish whenever they wanted, with zero copy editing. By the end of year one, the roster had grown to 18 contributors\u2014including an aspiring actor named Stephen Amell, long before he moved to LA to star in <em>Arrow<\/em>.<\/p>\n\n\n\n<p class=\"wp-block-paragraph\"><strong>The $75.36 Proof of Concept &amp; The Toronto.com Offer:<\/strong> While funding the site out of his agency paycheques, Tim\u2019s first-ever Google AdSense cheque arrived in the mail for <strong>$75.36<\/strong>, enough to prove the model worked and take his girlfriend (now wife), Bronwyn, out for dinner. Around that time, a headhunter for Torstar Digital actually called Tim to ask if he wanted to take over and run Toronto.com. He took the meeting, listened, and turned them down; they had no idea his explicit goal was to make them irrelevant.<\/p>\n\n\n\n<p class=\"wp-block-paragraph\"><strong>The Gawker-Style Point System:<\/strong> How do you pay writers when you have almost no money? Inspired by Nick Denton\u2019s Gawker Media, Tim committed <strong>80% of the site\u2019s revenue<\/strong> to contributors using a transparent point system: a base of 3 to 5 points per post, plus traffic bonuses. In one early month, total site revenue was <strong>$632.92<\/strong> across 544 points, meaning a writer who racked up 50 points took home <strong>$58.17<\/strong>. The real perks were concert passes, a Saturday NSFW sex column category called <em>Tno<\/em>, a viral 2006 Pride story about Jeffree Star punching an audience member (which Perez Hilton linked to, driving 35,000 views), and a full spread in <em>Variety<\/em> for TIFF 2006.<\/p>\n\n\n\n<p class=\"wp-block-paragraph\"><strong>The #1 Editorial Rule:<\/strong> By 2007, Tim instituted a two-page formatting guide with a default 250-word limit, but his most important rule wasn&#8217;t about length: <em>&#8220;Everything in the city is local&#8221;<\/em>. Writers were strictly forbidden from writing that they &#8220;trekked&#8221; to an event on the Danforth. To maintain credibility with neighbourhood locals, blogTO writers had to write as if they lived everywhere in the city.<\/p>\n\n\n\n<p class=\"wp-block-paragraph\"><strong>The Real Numbers Behind the Mini Cooper Ad:<\/strong> On the podcast, Tim recalled stepping into the lobby at Ogilvy to pitch Mini Cooper&#8217;s agency on taking over blogTO\u2019s rotating header photo\u2014the moment he knew the business had real legs. On Substack, he shares the exact figure: that Mini R56 launch campaign brought in <strong>$4,500<\/strong> across his three Freshdaily network sites (joining smaller $300 to $2,000 buys from the ROM, Virgin Mobile, and Zipcar, plus food-and-drink barter deals with The Drake Hotel). By the end of 2007, annual revenue across the network hit <strong>$65,000<\/strong>\u2014just as Ogilvy let him go and he and Bronwyn celebrated over drinks at The Embassy in Kensington Market.<\/p>\n\n\n\n<blockquote class=\"wp-block-quote is-layout-flow wp-block-quote-is-layout-flow\">\n<p class=\"wp-block-paragraph\"><strong>Go deeper on Substack:<\/strong> Read <a href=\"https:\/\/www.google.com\/search?q=%23\" target=\"_blank\" rel=\"noopener\"><em>The beginnings of blogTO: How it all began<\/em><\/a> and <a href=\"https:\/\/www.google.com\/search?q=%23\" target=\"_blank\" rel=\"noopener\"><em>The early years of blogTO: New websites and new partners<\/em><\/a>.<\/p>\n<\/blockquote>\n\n\n\n<h2 class=\"wp-block-heading\"><strong>2. Malware, the G20 Summit, and Turning Down the First $1.5M Buyout<\/strong><\/h2>\n\n\n\n<p class=\"wp-block-paragraph\">In our conversation, Tim emphasized how legacy Canadian media actively campaigned to paint blogs as untrustworthy, while well-funded local startups repeatedly launched with huge staffs only to burn out when revenue didn&#8217;t materialize. He also stressed his Silicon Valley mindset of &#8220;failing fast&#8221; whenever a product or bet wasn&#8217;t working.<\/p>\n\n\n\n<p class=\"wp-block-paragraph\">In his third Substack piece, covering 2010, Tim details just how fragile and cutthroat that middle era of growth really was:<\/p>\n\n\n\n<p class=\"wp-block-paragraph\"><strong>The Month the Site Went Dark:<\/strong> In mid-January 2010, hackers planted a backdoor script on blogTO\u2019s Media Temple server, deleting files and injecting malicious code into JavaScript that triggered terrifying malware warnings for readers. It took a full month and a complete server rebuild to fix, exposing the limits of Movable Type, the aging CMS they had used since 2004.<\/p>\n\n\n\n<p class=\"wp-block-paragraph\"><strong>Failing Fast on <em>Talk!<\/em>:<\/strong> Trying to fix comment moderation and increase site stickiness, Tim spent six months working with a San Francisco dev shop (which had built a similar system for <em>Serious Eats<\/em>) to create a user profile and forum hub called <em>Talk!<\/em>. Because it ran on Movable Type, it was too buggy to ship, and Tim pulled the plug\u2014an expensive sunk-cost lesson.<\/p>\n\n\n\n<p class=\"wp-block-paragraph\"><strong>Poachers and Uncredited Scoops:<\/strong> As blogTO hit 375,000 unique monthly users and 1.5 million page views, it became a talent launchpad for writers like future <em>Globe and Mail<\/em> columnist Robyn Urback and reporter Ben Spurr. Funded competitors like <em>The Mark<\/em> began poaching blogTO writers by offering $450 a week, which Tim couldn&#8217;t match. Meanwhile, legacy outlets routinely ripped off blogTO stories the day after publication without attribution. When Tim complained to the <em>Toronto Star<\/em>, the reporter apologized and admitted they had credited blogTO in their draft, but an editor had deleted it. CBC Radio would discuss its scoops on air while attributing them only to &#8220;a Toronto blog.&#8221;<\/p>\n\n\n\n<p class=\"wp-block-paragraph\"><strong>The G20 Summit, &#8220;Deadpool,&#8221; and DineSafe:<\/strong> June 2010 marked a turning point when the G20 Summit turned downtown Toronto into a fortress. Without needing press credentials, blogTO harnessed its community: readers submitted over 2,000 photos to the blogTO Flickr pool, and Tim personally photographed the temporary detention centres on Eastern Avenue. That same year, analytics led them to launch two staple beats: &#8220;Deadpool&#8221; (tracking local business closures) and weekly roundups of DineSafe restaurant health inspection infractions using the City of Toronto\u2019s new Open Data initiative\u2014a hit with readers that infuriated restaurant owners.<\/p>\n\n\n\n<p class=\"wp-block-paragraph\"><strong>The First Acquisition Offer (2010):<\/strong> Years before the ZoomerMedia sale, a legacy Toronto media company approached Tim in November 2010 looking to buy a digital foothold. They initially valued blogTO at <strong>$1 million<\/strong> ($250,000 upfront for 25%, with an option to reach 49% for another $250,000 over two years), eventually raising the valuation to <strong>$1.5 million<\/strong>. However, the strings were heavy: they had to reinvest the initial $250k in sales staff and site upgrades, required sign-off for any expense over $10,000, and wanted first right of refusal on Tim\u2019s remaining 51%. Tim didn&#8217;t want a partner telling him how to spend $10,000, so he walked away.<\/p>\n\n\n\n<blockquote class=\"wp-block-quote is-layout-flow wp-block-quote-is-layout-flow\">\n<p class=\"wp-block-paragraph\"><strong>Go deeper on Substack:<\/strong> Read <a href=\"https:\/\/www.google.com\/search?q=%23\" target=\"_blank\" rel=\"noopener\"><em>Someone wants to buy blogTO: Deal or no deal?<\/em><\/a>.<\/p>\n<\/blockquote>\n\n\n\n<h2 class=\"wp-block-heading\"><strong>3. The Video Pivot, Clubhouse Experiments, and Suitors at the Door<\/strong><\/h2>\n\n\n\n<p class=\"wp-block-paragraph\">On the podcast, Tim explained how blogTO survived major technological shifts\u2014moving from desktop to mobile, then to social feeds, and ultimately becoming a short-form vertical video company that got onto TikTok before almost any other Canadian publisher.<\/p>\n\n\n\n<p class=\"wp-block-paragraph\">In his August 2026 Substack post, Tim rewinds to 2021\u2014blogTO\u2019s final full year as an independent company\u2014to show how the pandemic supercharged that video machine and brought buyers out of the woodwork:<\/p>\n\n\n\n<p class=\"wp-block-paragraph\"><strong>Social Video Overtakes the Website:<\/strong> In 2021, blogTO\u2019s web traffic hit an all-time peak of <strong>32 million monthly page views<\/strong> and over <strong>350 million for the year<\/strong>. Yet beneath those numbers, years of subsidizing social video finally flipped the business model: Instagram and short-form video were on pace to generate not just the most views, but the most revenue and profit.<\/p>\n\n\n\n<p class=\"wp-block-paragraph\"><strong>Live Video Wins and &#8220;Fail Fast&#8221; Experiments:<\/strong> Stuck in lockdowns, Tim pivoted the team into live content. <em>Takeout Tuesday<\/em> on Instagram Live became a staple sponsored by DoorDash, celebrity lives featured Simu Liu and Russell Peters, and Tim even hired former CP24 producer Kris Pangilinan as Director of Live Operations alongside host Moose Bendago to run viewer-guided TikTok &#8220;quests&#8221;. By fall 2021, TikTok was literally paying blogTO to produce live series like <em>Lost in Toronto<\/em> (drawing 20,000+ viewers a night) and <em>Taste of TikTok<\/em>. True to his &#8220;fail fast&#8221; ethos, Tim also killed off plenty of pandemic duds: an Instagram live talent show (<em>Toronto&#8217;s Got Talent<\/em>) that drew fewer than 15 entries, a dedicated Clubhouse team (<em>Toronto Talks<\/em>) that faded once the world reopened, Twitter Spaces (which lacked basic analytics or recording downloads), and a blogTO Discord server that not a single staffer wanted to use.<\/p>\n\n\n\n<p class=\"wp-block-paragraph\"><strong>Reinventing the Video Crew:<\/strong> Until mid-2021, blogTO shot 2-minute square videos using two-person DSLR crews. Recognizing the shift to full-screen vertical Reels, Tim judged hundreds of job applicants by their custom application videos rather than their resumes, hiring Taylor Patterson, Briana-Lynn Brieiro, and intern Tiana Atapattu Jayatunga as one-person iPhone crews who shot, edited, and starred in sub-minute vertical videos. They bundled two or three shoots per neighbourhood each day, and Tim licensed the Firework video player to embed those vertical videos next to related web articles\u2014charging sponsors pure-profit extension fees and running pre-roll ads on editorial clips.<\/p>\n\n\n\n<p class=\"wp-block-paragraph\"><strong>The Suitors Tim Turned Down in 2021:<\/strong> While Tim told me on the podcast that multiple companies approached him post-pandemic, his Substack reveals who they actually were. Narcity\u2019s Chuck checked in every three months to pitch a merger or sale. An unnamed major Canadian TV production company spent six weeks pitching a 3-to-5-year earn-out, while a financially strapped national broadcaster bowed out when they couldn&#8217;t meet Tim\u2019s valuation. Most notably, <strong>Rogers<\/strong> reached out in April 2021 about a &#8220;partnership or possible acquisition&#8221;. Tim shut it down, suspecting the telecom giant either just wanted ad inventory or wanted to muzzle an outlet that had published critical pieces about the Rogers family and Canada&#8217;s high internet and data prices.<\/p>\n\n\n\n<blockquote class=\"wp-block-quote is-layout-flow wp-block-quote-is-layout-flow\">\n<p class=\"wp-block-paragraph\"><strong>Go deeper on Substack:<\/strong> Read <a href=\"https:\/\/www.google.com\/search?q=%23\" target=\"_blank\" rel=\"noopener\"><em>blogTO goes live: We were a hot property, and everyone knew it<\/em><\/a>.<\/p>\n<\/blockquote>\n\n\n\n<h2 class=\"wp-block-heading\"><strong>4. Inside the $15M ZoomerMedia Deal and Moses Znaimer\u2019s Office<\/strong><\/h2>\n\n\n\n<p class=\"wp-block-paragraph\">One of the most candid parts of our podcast was Tim admitting he had zero interest in selling blogTO, never built a pitch deck, and agonized over a pros-and-cons list right up until the second he signed the $15 million deal with ZoomerMedia.<\/p>\n\n\n\n<p class=\"wp-block-paragraph\">In his September 15, 2026 Substack post, Tim takes us straight inside the room with Canadian television pioneer Moses Znaimer (the creator of Citytv, MuchMusic, and Speakers Corner) and breaks down the exact deal structure:<\/p>\n\n\n\n<p class=\"wp-block-paragraph\"><strong>BlackBerrys and Free Parking:<\/strong> Beginning in the spring of 2021, Tim met with Moses in person at the ZoomerPlex in Liberty Village. While Moses saw blogTO as the modern, scrappy street-level heir to early Citytv, there were humorous generational gaps. Moses still carried a BlackBerry rather than an iPhone, read blogTO via its website and newsletter rather than TikTok, and proudly touted the ZoomerPlex&#8217;s ample free parking as a major perk for blogTO&#8217;s staff\u2014with Tim not having the heart to tell him that almost his entire team biked or took transit.<\/p>\n\n\n\n<p class=\"wp-block-paragraph\"><strong>&#8220;All or Nothing&#8221; at $15 Million:<\/strong> In their first meeting, Moses proposed buying a majority stake rather than 100%, arguing that founders lose their drive once fully bought out. Tim refused to become a powerless minority partner, telling Moses it was all or nothing and naming his price: <strong>$15 million<\/strong>. When Moses asked what he wanted to buy\u2014just blogTO, or the dormant Freshdaily network assets like <em>Beyond Robson<\/em> and <em>Midnight Poutine<\/em> that we discussed on the podcast\u2014Moses said he wanted all of it.<\/p>\n\n\n\n<p class=\"wp-block-paragraph\"><strong>Reshaping the Terms:<\/strong> On August 18, 2021, ZoomerMedia made its first formal written offer of $15 million, split between cash, deferred payments, and ZoomerMedia stock. Over lunch the next day at Barrio in Leslieville with ZoomerMedia deputy COO Omri (who pulled up in a white Tesla while Tim biked over from his house), Tim pushed back on the terms. Advised by his accountant to avoid taking stock, Tim negotiated for months\u2014prompting Moses to joke in an email that he hoped Tim would say yes <em>&#8220;before I die of old age trying to do this deal&#8221;<\/em>. The final November structure was <strong>$10 million in cash at closing<\/strong>, with the remaining <strong>$5 million paid over three years<\/strong>\u2014and remarkably, no retention clause in his employment contract as President of blogTO, meaning Tim could have legally resigned on day one.<\/p>\n\n\n\n<p class=\"wp-block-paragraph\"><strong>The Hidden Pressures Behind the Pros-and-Cons List:<\/strong> On the podcast, Tim mentioned financial security for his family as the main pro of selling. On Substack, he reveals the heavier realities weighing on him in December 2021. First, blogTO was fighting <strong>two separate defamation lawsuits<\/strong> simultaneously during due diligence (winning one via Zoom cross-examination from his basement, and settling the other for cash for the first time in company history) with no media liability insurance. Second, the pandemic made him realize that if he got sick, he had no succession plan or second-in-command. Third, the Canadian media market was being warped by government and tech interventions\u2014blogTO had just received Qualified Canadian Journalism Organization (QCJO) tax credit status and a surprise <strong>$1 million+ multi-year deal from Facebook\u2019s News Innovation Test<\/strong>, while being excluded from Google\u2019s News Showcase. Selling handed that regulatory and platform risk off to a larger balance sheet.<\/p>\n\n\n\n<p class=\"wp-block-paragraph\"><strong>Takeout Sushi in Lockdown:<\/strong> On December 16, 2021, while blogTO was streaming Keanu Reeves live to 6,000 viewers at the Scotiabank Theatre premiere of <em>The Matrix Resurrections<\/em>, Tim&#8217;s lawyers were finalizing due diligence. He signed the papers on Friday, January 21, 2022, and celebrated in his kitchen with Bronwyn and their kids over lockdown takeout sushi.<\/p>\n\n\n\n<blockquote class=\"wp-block-quote is-layout-flow wp-block-quote-is-layout-flow\">\n<p class=\"wp-block-paragraph\"><strong>Go deeper on Substack:<\/strong> Read <a href=\"https:\/\/www.google.com\/search?q=%23\" target=\"_blank\" rel=\"noopener\"><em>My meetings with Moses Znaimer: And the sale of blogTO to Zoomer Media<\/em><\/a>.<\/p>\n<\/blockquote>\n\n\n\n<h2 class=\"wp-block-heading\"><strong>5. The Great Office Plant Heist, Dave Portnoy, and Acquiring Rivals<\/strong><\/h2>\n\n\n\n<p class=\"wp-block-paragraph\">In our interview, Tim explained why he kept ad placements minimal and refused to sell advertorial content, even if it meant leaving money on the table. He also noted that when you sell your company, the new owners have every right to run it differently.<\/p>\n\n\n\n<p class=\"wp-block-paragraph\">His sixth Substack post details the wild first year inside ZoomerMedia in 2022\u2014from corporate culture shocks to international media feuds and a 70% revenue surge:<\/p>\n\n\n\n<p class=\"wp-block-paragraph\"><strong>The ZoomerPlex Plant Caper:<\/strong> When blogTO moved into its new second-floor office at the ZoomerPlex in April 2022, the team\u2019s #1 request was office plants, which Tim secured through a barter deal. One morning, half the plants vanished. Worried a thief had slipped in through a faulty parking lot door, Tim asked IT to check the security cameras\u2014only to be led by maintenance to a room off reception where all the plants were stashed. Moses had ordered them removed because ZoomerMedia had a corporate ban on office plants and personal photos, fearing dead plants would litter the building. Tim pushed back, hauled the plants back upstairs with his editor Lauren, and turned the survival rate of the plants into a recurring joke during his one-on-one sushi-and-sake meetings with Moses.<\/p>\n\n\n\n<p class=\"wp-block-paragraph\"><strong>Going Toe-to-Toe with Dave Portnoy:<\/strong> In late April 2022, Barstool Sports founder Dave Portnoy announced a Toronto pizza tour. A blogTO reporter sent Instagram DMs to local pizzerias that had invited him, asking if they were aware of sexual misconduct allegations against Portnoy (which he had denied) and whether that changed their invitations. When the story dropped on the day Portnoy landed, he went nuclear\u2014blasting blogTO to millions of followers, appearing on Fox News to call blogTO a desperate &#8220;liberal blog,&#8221; and filming a review outside Fresca Pizza on College Street where he pointed at a blogTO &#8220;Best of Toronto&#8221; window decal and joked with former Maple Leaf enforcer Tie Domi about going to blogTO headquarters to <em>&#8220;crack some skulls&#8221;<\/em>. Editor Lauren accepted Portnoy\u2019s challenge to go on his show live, calmly defending the reporter\u2019s job and the article&#8217;s packaging until Portnoy admitted, <em>&#8220;I hate that I liked that answer,&#8221;<\/em> and officially squashed the beef.<\/p>\n\n\n\n<p class=\"wp-block-paragraph\"><strong>The Michelin Scoop &amp; Pulling the Revenue Levers:<\/strong> Weeks later, Tim personally broke the scoop (under the &#8220;Staff&#8221; byline) that the Michelin Guide was coming to Toronto\u2014inadvertently spoiling an embargoed announcement blogTO hadn&#8217;t been invited to, which resulted in Destination Toronto pettily excluding the city&#8217;s biggest food publication from the September ceremony. Meanwhile, ZoomerMedia brought blogTO\u2019s longtime external ad sales team (Suite 66) in-house, added more ad units to the site, and began selling the exact branded editorial Tim had resisted for 17 years. By September 2022, Omri told the <em>Toronto Star<\/em> that ZoomerMedia had <strong>increased blogTO\u2019s revenue by 70%<\/strong>.<\/p>\n\n\n\n<p class=\"wp-block-paragraph\"><strong>Buying Daily Hive and the &#8220;Minyan&#8221; Meetings:<\/strong> That same September, ZoomerMedia acquired blogTO\u2019s longtime Vancouver rival, Daily Hive (which had grown in the vacuum left when Tim shut down <em>Beyond Robson<\/em> years earlier), for <strong>$16.4 million<\/strong>. Tim flew to Yaletown with Omri for an awkward town hall with Daily Hive CEO Karm Sumal, asking his fiercest competitor of the previous week to open up their playbook. Back in Toronto, Tim\u2019s schedule filled up with corporate forecasting and a standing 90-minute division-head meeting led by Omri called &#8220;the Minyan&#8221;.<\/p>\n\n\n\n<blockquote class=\"wp-block-quote is-layout-flow wp-block-quote-is-layout-flow\">\n<p class=\"wp-block-paragraph\"><strong>Go deeper on Substack:<\/strong> Read <a href=\"https:\/\/www.google.com\/search?q=%23\" target=\"_blank\" rel=\"noopener\"><em>blogTO under Zoomer Media: A new office, Dave Portnoy, and the acquisition of Daily Hive<\/em><\/a>.<\/p>\n<\/blockquote>\n\n\n\n<h2 class=\"wp-block-heading\"><strong>6. How Bill C-18 Broke the Model\u2014and the Final Walkout<\/strong><\/h2>\n\n\n\n<p class=\"wp-block-paragraph\">Near the end of our podcast, I asked Tim about the overarching reason he was let go, and he pointed to two things: the natural transition of control after an acquisition, and the devastating industry fallout from Bill C-18, Canada\u2019s Online News Act.<\/p>\n\n\n\n<p class=\"wp-block-paragraph\">In his final two Substack installments, Tim lays out the receipts on how the Canadian government crippled digital-native publishers, how he spent his final year reorganizing ZoomerMedia\u2019s digital empire, and how his final day played out minute by minute:<\/p>\n\n\n\n<p class=\"wp-block-paragraph\"><strong>The Brutal Math of the Online News Act:<\/strong> Tim had opposed government intervention since a 2016 roundtable, viewing Bill C-18\u2014which followed 52 lobbying meetings between legacy newspaper group News Media Canada and the government\u2014as a bailout for failing print papers at the expense of digital innovators. In August 2023, Meta blocked Canadian news publishers, cutting blogTO off from nearly <strong>one million Instagram followers<\/strong> overnight and wiping out a massive sponsored-video revenue stream that legacy newspapers had never managed to build. And when Google agreed in late 2023 to pay $100 million a year into a fund distributed by newsroom headcount, <strong>60.6% of the money went to just 14 legacy media companies<\/strong> (Postmedia received $19.5 million; Bell Media got $16.8 million; the CBC got $13.9 million), while Freshdaily\/blogTO received just <strong>$454,701<\/strong> across the first two years.<\/p>\n\n\n\n<p class=\"wp-block-paragraph\"><strong>The QCJO Trap and &#8220;Shadow Media&#8221;:<\/strong> The cruellest twist was why Meta refused to unblock blogTO (aside from a brief accidental unblocking in October 2023): blogTO was a designated Qualified Canadian Journalism Organization (QCJO). The tax credit Tim had celebrated in 2021 as &#8220;free money&#8221; became a trap. Conversely, competitor Narcity had been <em>rejected<\/em> for QCJO status for not producing enough original news; in 2024, Narcity sent that government rejection letter to Meta and got all its accounts restored within a week. Meanwhile, unblocked &#8220;shadow media&#8221; accounts like 6ixBuzz, Waveroom, and Real Toronto Newz kept posting news clips and growing on Instagram while the actual reporters were locked out.<\/p>\n\n\n\n<p class=\"wp-block-paragraph\"><strong>The Pivot to <em>Dished<\/em>, Quality Over &#8220;Rage Bait,&#8221; and <em>CULTR<\/em>:<\/strong> Blocked on Meta, Tim shifted blogTO\u2019s food video machine over to <em>Dished Toronto<\/em> (an unblocked lifestyle brand acquired with Daily Hive), rebuilding it with the classic blogTO playbook of window decals and street giveaways. On the web, being freed from the Facebook algorithm had a silver lining: blogTO ditched emotional &#8220;rage bait&#8221; to refocus on quality local arts, culture, and history, even as Google\u2019s AI Overviews ushered in what Tim saw as the &#8220;managed decline&#8221; of the open web. On TikTok and YouTube, new formats like Anton Wong\u2019s transit races (racing the TTC on foot) racked up millions of views. In summer 2024, Omri put Tim in charge of all the digital brands\u2014blogTO, Daily Hive, Dished, Offside, recent $5M acquisition Curiocity, and $950k acquisition MobileSyrup\u2014leading Tim to launch a new lifestyle brand in early 2025 called <strong>CULTR<\/strong> that used Instagram\u2019s &#8220;Collab&#8221; post feature to cross-pollinate and monetize their unblocked accounts.<\/p>\n\n\n\n<p class=\"wp-block-paragraph\"><strong>The Red Mini Cooper and the Final Meeting:<\/strong> By late 2024, blogTO quietly turned 20, Moses\u2019s signature (&#8220;Executive Producer&#8221;) was added to the website footer, and a red blogTO-wrapped Mini Cooper S (&#8220;the blog mobile&#8221;) arrived in the parking lot. By January 2025\u2014just as the three-year window for his final $5 million acquisition payout arrived\u2014Tim knew he was going to be fired. He spotted former <em>Torontoist<\/em> editor David Topping outside the ZoomerPlex after an interview, told him not to worry about him, and wished him luck. Tim quietly tied up loose ends, returned his company laptop a full month early, and took his family to South America for March break. On his first day back\u2014Monday, March 24, 2025\u2014Omri called him into his office. Tim walked in already holding his coat and bag, declined an offer to stay on for a two-month transition, and made one key request: that Omri tell the staff he was fired so his team would never think he quit on them. They shook hands, Tim walked straight out to the parking lot, called Bronwyn on the drive home, and published the LinkedIn post that kicked off our podcast.<\/p>\n\n\n\n<blockquote class=\"wp-block-quote is-layout-flow wp-block-quote-is-layout-flow\">\n<p class=\"wp-block-paragraph\"><strong>Go deeper on Substack:<\/strong> Read <a href=\"https:\/\/www.google.com\/search?q=%23\" target=\"_blank\" rel=\"noopener\"><em>blogTO and the Online News Act: Instagram and Facebook get blocked<\/em><\/a> and <a href=\"https:\/\/www.google.com\/search?q=%23\" target=\"_blank\" rel=\"noopener\"><em>My last year at blogTO: A car, a plan, a meeting, and how it ended<\/em><\/a>.<\/p>\n<\/blockquote>\n\n\n\n<p class=\"wp-block-paragraph\">Watching a founder build something from a condo party room into the cultural fabric of a city\u2014and then reading the unvarnished truth of how it scaled and how it ended\u2014is a rare gift in Canadian entrepreneurship. If you haven&#8217;t yet, <a href=\"https:\/\/www.youtube.com\/watch?v=4CcnT1r1868\" target=\"_blank\" rel=\"noopener\">watch or listen to my full conversation with Tim Shore on Episode #31<\/a>, and make sure to subscribe to Tim&#8217;s Substack to read every chapter in his own words.<\/p>\n","protected":false},"excerpt":{"rendered":"<p>When Tim Shore sat down with me for Episode #31 of the podcast, we opened with a screenshot of the LinkedIn post that shocked Toronto\u2019s media scene: after a 20-year run, Tim had been fired from blogTO and ZoomerMedia, the very company he founded and built from scratch. As we unpacked it over nearly two [&hellip;]<\/p>\n","protected":false},"author":1,"featured_media":90308,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_coblocks_attr":"","_coblocks_dimensions":"","_coblocks_responsive_height":"","_coblocks_accordion_ie_support":"","_jetpack_newsletter_access":"","_jetpack_dont_email_post_to_subs":true,"_jetpack_newsletter_tier_id":0,"_jetpack_memberships_contains_paywalled_content":false,"_jetpack_feature_clip_id":0,"_jetpack_memberships_contains_paid_content":false,"footnotes":"","jetpack_publicize_message":"{title}\n\n{excerpt}\n\n{url}","jetpack_publicize_feature_enabled":true,"jetpack_social_post_already_shared":true,"jetpack_social_options":{"image_generator_settings":{"template":"highway","default_image_id":0,"font":"","enabled":false},"version":2},"_wpas_customize_per_network":false,"jetpack_post_was_ever_published":false,"rank_math_title":"","rank_math_description":"","rank_math_canonical_url":"","rank_math_focus_keyword":""},"categories":[1,75],"tags":[],"class_list":["post-90300","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-syng","category-feature"],"jetpack_publicize_connections":[],"jetpack_sharing_enabled":true,"jetpack_likes_enabled":true,"jetpack-related-posts":[],"jetpack_shortlink":"https:\/\/wp.me\/p7CVvN-nus","jetpack_featured_media_url":"https:\/\/i0.wp.com\/paulsyng.com\/blog\/wp-content\/uploads\/2026\/10\/9c955950-4deb-45b7-ad18-2f9c442a682a_812x546.jpg?fit=812%2C546&quality=89&ssl=1","_links":{"self":[{"href":"https:\/\/paulsyng.com\/blog\/wp-json\/wp\/v2\/posts\/90300","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/paulsyng.com\/blog\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/paulsyng.com\/blog\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/paulsyng.com\/blog\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/paulsyng.com\/blog\/wp-json\/wp\/v2\/comments?post=90300"}],"version-history":[{"count":4,"href":"https:\/\/paulsyng.com\/blog\/wp-json\/wp\/v2\/posts\/90300\/revisions"}],"predecessor-version":[{"id":90307,"href":"https:\/\/paulsyng.com\/blog\/wp-json\/wp\/v2\/posts\/90300\/revisions\/90307"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/paulsyng.com\/blog\/wp-json\/wp\/v2\/media\/90308"}],"wp:attachment":[{"href":"https:\/\/paulsyng.com\/blog\/wp-json\/wp\/v2\/media?parent=90300"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/paulsyng.com\/blog\/wp-json\/wp\/v2\/categories?post=90300"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/paulsyng.com\/blog\/wp-json\/wp\/v2\/tags?post=90300"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}