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.

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DOTS PODCAST ON ALL PLATFORMS

YouTube: https://youtube.com/playlist?list=PLJhdYWtEVH6R9lX2exP_8ni9YGKNTZ1b8&si=4s69nrKCahy5vQ5O

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Apple: https://podcasts.apple.com/us/podcast/dots-podcast-of-paul-syng/id1557392269  

Podcasters: https://podcasters.spotify.com/pod/show/paulsyng

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GRAB YOUR CEO CLARITY STARTER KIT 

http://claritytoscale.biz

READ PLATONIC BLOG

https://paulsyng.com/blog/

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SPEAKER LINKS

Host, Paul Syng:

https://x.com/paulsyng

https://www.linkedin.com/in/paulsyng/

Guest, Tim Shore

https://x.com/timshore

https://www.linkedin.com/in/tim-shore/

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CHAPTERS

00:00 - Early days of blogTO and getting fired from his full-time job

5:20 - Why Tim started blogTO back in 2004

11:30 - Blogs, photoblogs and the importance of community

14:08 - Growing audience and brand awareness in the first few years

23:00 - Early signs of traction and success

36:25 - Tim's reader-first approach and saying no to advertisers

43:55 - Tim's iterative approach and responding to market disruptions

48:48 - Clickbait headlines and packaging web content

1:09:12 - blogTO's curatorial approach to covering the city

1:14:16 - The competitive landscape and respecting the reader

1:23:56 - What some competitors missed

1:26:42 - Tim's worst (but necessary?) business decisions

1:32:56 - Challenges retaining core staff and work-life balance

1:40:35 - Selling blogTO to ZoomerMedia and getting fired

1:53:35 - Closing