Andrew Pupolin founded Sidestage Presents in 2015, which has brought his influence to many major festivals and events including Montreal’s F1 weekend, Calgary Stampede and Ottawa Bluesfest. The 39-year-old has built an internationally-connected company built around Canadian live music and connecting with brands collaborating with international brands like Nike, Adidas, Hennessy and more. Pupolin is a true devotee to the Canadian community, not just through music, but also through philanthropy, offering mentorship and training through Toronto nonprofit initiative The Remix Project.

He also connects artists with Universities and Colleges throughout Canada through Frosh Week and Homecoming seasons and aligns artists for speaking engagements to students about mental health, anti-bullying and wellness. Sidestage is active in Toronto, putting on 250 shows a year, including recent ones with major hip-hop, R&B and electronic artists like Freddie Gibbs, Lil Simz, Bladee and more. For Pupolin, watching artists increase their draw is a major motivator. “Watching artists and their teams grow from performing for 50 to 100 people to headlining arenas and festivals is exactly why we do what we do,” he says.