TLDR: The tour for Gavin Sheppard’s new book, 100: A City Kid’s Survival Guide, stops in Ottawa on Thursday and Calgary on Oct. 1, featuring conversations with Canadian rappers City Fidelia and Drezus.
The launch of 100: A City Kid’s Survival Guide isn’t just about a book. It’s about live conversations that stretch its meaning across Canadian cities. After a powerful Toronto event with Dae The Poet earlier this month, Gavin Sheppard takes his debut project on the road with stops in Ottawa and Calgary.
This Thursday, Sept. 25, Sheppard links with City Fidelia inside Octopus Books. The accomplished Ottawa rapper and community builder mirrors Sheppard’s spirit of bridging artistry with activism. Expect a night of raw conversation about growing up urban, reclaiming community from commerce, and the hidden costs of building real social capital. Tickets are available now for free through Eventbrite.
The newly announced Calgary date doubles down on that approach. On Oct. 1 at Alcove Beltline, Sheppard will sit down with Drezus, the Plains Cree rapper who flipped struggle into purpose through culture and music. The pairing speaks to the book’s resonance: 100 isn’t limited by city borders. It’s about resilience wherever the concrete meets the community. Drezus’ story of incarceration, recovery, and Indigenous pride makes him the perfect partner for expanding the conversation into the Prairies.
These events reflect Sheppard’s lifelong mission of creating platforms. Just as 100 collects one hundred truths in print, each stop on the tour acts like a new annotation. In Toronto, Ottawa, Calgary, and beyond, the book becomes less of a product and more of a process. It’s a living conversation about what survival means in the city.
For anyone who picks up the book or shows up in person, it’s clear: this isn’t a victory lap for Sheppard. It’s the start of a dialogue, as much about the audience as the author.
For more information about 100: A City Kid’s Survival Guide, check out our feature on the book, or visit the the official website, city-kid-100.com. You can purchase the book right now at linkinbioinc.com.
