Shad reveals why the best creative careers are built on risk, joy, and refusing to let the work turn into just a job. From a sister secretly entering him into the contest that funded his first album to the "love of the game" mindset that carried him from rap into CBC's Q, Hip Hop Evolution, and beyond, this conversation is packed with the kind of hard-earned creative wisdom artists, founders, and builders need right now.Ryan Mack opens up the interview by tracing Shad's path from early mixtape-era ambition to Juno-winning artist, Peabody and Emmy-winning storyteller, and Memo Festival keynote speaker. What follows is a wide-ranging look at the moments that shaped Shad's career, the people who believed in him before the world did, and the choices that kept him evolving without losing his center.You'll discover:

• Why external validation matters early in a creative life, and why it has to matter less later
• The Michael Jordan "love of the game" clause that became a blueprint for protecting artistic joy
• How to tell when an idea is worth committing to, even if it looks like a bad career move on paper
• Why risk creates tension, stakes, and meaning in art
• How Shad decides when a project has arrived at the right moment in culture

He also breaks down the long-term relationships that made projects like Hip Hop Evolution possible, including working with Darby Wheeler and Rodrigo Basquenin, and explains why continuity with good people matters as much as talent. Then, in one of the most revealing parts of the episode, Shad shares the albums that shaped him, from Lauryn Hill's MTV Unplugged No. 2.0 and Kanye West's The College Dropout to Ras Kass, The Cardigans, and Common.This episode matters because so many creatives get stuck between playing it safe and chasing what actually feels true. Shad makes the case that fulfillment comes from finishing what you're compelled to make, protecting your curiosity, and staying in motion long enough to grow into the next version of yourself.If you care about making things that last, building with the right people, or staying connected to your own creative spark, this is essential listening. Perfect for artists, entrepreneurs, and anyone who needs a reminder that the work only works when you still love it.

Join us as we explore the innovative world of sports engineering with Gillian Pinder, who combines technical expertise with athlete-centered design to push the boundaries of mountain sports gear and footwear. Discover her journey, testing methodologies, and insights into inclusive product development.

In this episode of the Memo Creative Festival podcast, hosts Taylor Pfeifer and Brooke Hoffos interview Jillian Ross, a master printer and collaborative artist based in Saskatoon, Canada. Jillian shares her journey into printmaking, her experiences in establishing a collaborative studio in Johannesburg, and her work with renowned artist William Kentridge. The conversation explores the importance of collaboration in art, the cultural dynamics between South Africa and Canada, and the future of printmaking in Saskatoon. Jillian emphasizes the significance of community, transparency, and the creative process in her work, inspiring listeners to embrace their artistic journeys.