100: A City Kid’s Survival Guide by Gavin Sheppard blends tweets, micro-fiction, and illustrations into a modern field manual for city life.
Gavin Sheppard has been a fixture in Toronto’s hip-hop and arts community for over two decades, shaping spaces where young talent could find their voice long before it was fashionable to talk about “platform building.” With 100: A City Kid’s Survival Guide, he distills that experience into something more intimate — a father’s notes, a city’s lessons, and a blueprint for survival. The book arrives like a time capsule cracked open, revealing the coded slang, shifting masculinity, and bittersweet truths of a digital-first generation.
The Toronto-based social entrepreneur has spent more than 15 years building spaces for youth creativity through projects like The Remix Project, TEDxToronto, and Quiet As Kept. With 100, Sheppard steps into a different role: that of cultural scribe, bottling the voice of a father writing field notes to his son while also capturing the chaotic poetry of city adolescence. Visual artist Thomas B. aka TG provides the illustrations, which balance innocence and grit, echoing the contradictions baked into the text.
Gavin Sheppard (aka Public) and Thomas B. (aka TG) (Photos: Andrew Palmer @illdefinedartistry)
Sheppard’s background as a strategist and mentor seeps through every page. These aren’t sterile tweets bound into paper. They’re survival notes that double as affirmation and warning, stitched together to reflect the realities of coming-of-age under fluorescent lights and social media timelines. Glenn Kaino described the book as “a paradoxical embrace and challenge of youthful masculinity.” Canadian star Jessie Reyez went with a different kind of endorsement: “This is harddddddddddddDDDDD.”
By publishing through Toronto indie press Link In Bio, Sheppard underscores his belief in independent voices pushing culture forward. This book isn’t positioned as a nostalgic glance back but as a tool for now: a gritty, funny, sometimes heartbreaking record of the rules, rituals, and resilience it takes to keep it one hundred in the city. For more information, visit the official website, city-kid-100.com.
100 Events
The release of 100: A City Kid’s Survival Guide isn’t staying on the page. This Thursday, Sheppard takes the book to Ottawa for a live conversation with rapper and community builder City Fidelia at Octopus Books.
A week later, on Oct. 1, the tour moves west to Calgary, where Sheppard will sit down with Drezus, the Plains Cree rapper whose own journey from struggle to self-determination mirrors many of the book’s survival notes. These events extend the spirit of 100 into the room — turning its lessons into dialogue, and reminding audiences that survival is always a shared story.
Check out out our feature on both events for more information.
