#31 Tim Shore — Inside Tim Shore’s blogTO Origin and Exit

Tim Shore is the visionary founder of blogTO, Toronto's premier digital media platform for local news, culture, and events, which he launched in 2004 as a side hustle while working in advertising. His passion for the project grew so intense that it led to his firing from his day job, prompting him to go all-in and transform blogTO into Canada's largest independent blog of its kind. Drawing from early experiences as a CNN intern and managing digital campaigns for brands like Yahoo! and Microsoft, Tim scaled the site to millions of monthly users. In January 2022, he sold blogTO to ZoomerMedia for $15 million, marking a pinnacle of success — only for his journey to come full circle when the company terminated him on March 25, 2025. In this episode, Tim shares candid reflections on resilience, building a media empire from scratch, navigating viral content strategies, and advice for aspiring entrepreneurs and side hustlers eyeing the digital space.__DOTS PODCAST ON ALL PLATFORMSYouTube: https://youtube.com/playlist?list=PLJhdYWtEVH6R9lX2exP_8ni9YGKNTZ1b8&si=4s69nrKCahy5vQ5OSpotify: https://open.spotify.com/show/2z0Vgy7eNR6XSk3M0uSugp?si=eb5369dea4314099 Apple: https://podcasts.apple.com/us/podcast/dots-podcast-of-paul-syng/id1557392269  Podcasters: https://podcasters.spotify.com/pod/show/paulsyng__GRAB YOUR CEO CLARITY STARTER KIT http://claritytoscale.bizREAD PLATONIC BLOGhttps://paulsyng.com/blog/NEED HELP WITH A COMPLEX CHALLENGE? https://paulsyng.com__SPEAKER LINKSHost, Paul Syng:https://x.com/paulsynghttps://www.linkedin.com/in/paulsyng/Guest, Tim Shorehttps://x.com/timshorehttps://www.linkedin.com/in/tim-shore/__CHAPTERS00:00 - Early days of blogTO and getting fired from his full-time job5:20 - Why Tim started blogTO back in 200411:30 - Blogs, photoblogs and the importance of community14:08 - Growing audience and brand awareness in the first few years23:00 - Early signs of traction and success36:25 - Tim's reader-first approach and saying no to advertisers43:55 - Tim's iterative approach and responding to market disruptions48:48 - Clickbait headlines and packaging web content1:09:12 - blogTO's curatorial approach to covering the city1:14:16 - The competitive landscape and respecting the reader1:23:56 - What some competitors missed1:26:42 - Tim's worst (but necessary?) business decisions1:32:56 - Challenges retaining core staff and work-life balance1:40:35 - Selling blogTO to ZoomerMedia and getting fired1:53:35 - Closing

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