On a damp Wednesday morning in Toronto, Shad is standing barefoot in the driveway of his stacked townhouse complex, decked out in shorts and his ubiquitous Manifesto hoodie. He is doing so because an interviewer is lost, having already knocked on the wrong door once. Upon meeting, he smiles and apologizes that first, he need to check on a friend’s house around the corner — then looks down at his feet and explains, “I don’t really wear shoes in the summer.”

Back inside, he introduces a visitor to his wife and takes a seat at a stool in the kitchen, offering a cup of tea. The furnishings are sparse — not out of some determined effort towards minimalism, but from an impending move to another place nearby. A book about prenatal yoga sits on the island counter. The two are expecting their first child later in the year.

Welcome to the life of one of Canada’s most accomplished hip-hop artists, one of only two — the other one being industry favourite Jazz Cartier — to beat out Drake for a Rap Recording Juno. It all seems so normal, especially considering Shad — born Shadrach Kabango — is enjoying something of a career year at the moment; in 2017, his latest project, the documentary series Hip-Hop Evolution, won both an International Emmy and a Peabody Award. Soon, the London, Ontario-raised emcee will make his musical return with A Short Story About a War, a full-length project due out October 26th.

“It’s quite a thing to think about, you know? Because when I made my first album, I really didn’t know if I would make any more,” he says. “I didn’t anticipate five years, ten years, let alone maybe even a second album.”

“Now, when I look back, it’s kind of crazy to me. I’ve just been able to do a lot of things that I feel grateful for every morning when I wake up. I got to share so much of my story and say so many things, and I did not anticipate any of it.” – Shad

When Shad made his debut in 2005 with When This Is Over, he was in his early twenties and wrapping up a business degree at Wilfrid Laurier University. He recorded the album with the winnings from a contest hosted by 91.5 The Beat, a local radio station based in Kitchener-Waterloo.

“I was wrestling with what a lot of kids wrestle with in school, which was ‘what am I going to do next?’ And ‘what do I actually have the most to contribute to?’ And a part of me suspected that was music or something creative, but of course, you never know,” says Shad.

He kept the news of the contest and progress on the album mostly to himself, afraid of falling short of others’ expectations. If Shad was modest about his talents, however, his friend and classmate (now longtime manager and business partner) Gaurav Sawhney saw potential.

“As he tells it, one day in fourth year, someone was like, ‘Hey, have you heard Shad’s album?’ And he was like, ‘What are you talking about?’” Shad laughs. “He got it, and we kind of started working together and started learning it all together.”

“I was wrestling with what a lot of kids wrestle with in school, which was ‘what am I going to do next?’ And ‘what do I actually have the most to contribute to?’ And a part of me suspected that that was music or something creative, but of course, you never know.” – Shad

With the help of Shad’s older sister, they began booking shows throughout Southern Ontario, then across Canada — at times, performing for crowds of two or three; other times, opening for the likes of Sadat X and Common in front of much larger audiences.

“If we booked a little mini tour, like five shows, generally one would be good,” Shad laughs. “Two out of five would be terrible, and then the other two were somewhere in the middle.”

By 2007, the crowds had grown. Shad’s sophomore effort, The Old Prince, was shortlisted for a Polaris Prize and earned him a Juno nomination for Rap Recording of the Year — an award he would win three years later for his follow-up TSOL, beating a debutant Drake who was hosting the award ceremony and widely expected to claim the prize.

“That’s a hilarious moment to think back on,” says Shad. “I’m walking out of that gala with G (Gaurav Sawhney), and as soon as we get out of the gala, we burst out laughing — just rolling on the floor, laughing.”

“If we booked a little mini tour, like five shows, generally one would be good. Two out of five would be terrible, and then the other two were somewhere in the middle.” – Shad

At last, Shad had arrived. Tour dates in the United States and Europe would follow, and by 2013 — the same year as his Flying Colours release — CBC Music had listed Shad as the second-greatest Canadian rapper ever, behind only Maestro Fresh Wes. He might not have found the same audience as Drake (and really, who has?) but he was every bit the Canadian favourite: praised for his wit and beloved for his personality.

At the same time, Kabango was ready for something new.

“There was this sense of, like, ‘Okay, cool. What am I going to explore next?’ Music is here, and I’m going to keep doing that, but I was kind of looking around a little bit, too,” he says.

His first public opportunity would come with CBC Radio’s popular ‘q’ program in 2015, following previous host Jian Ghomeshi’s ouster in the midst of a sexual assault scandal. Shad took the reins in the hottest of hot seats, looking to win over an audience that — in some parts — had still remained loyal to his predecessor.

“I remember, I had my first day [at CBC’s ‘q’], and it felt like a living funeral — not in a sad way, [but] there was so much tribute being paid, and I’m like, ‘this is crazy.’ Because to my mind, I was just starting a job, you know?” – Shad

“I didn’t expect [getting the role] to be as big of a thing as it was,” he says. “I remember, I had my first day, and it felt like a living funeral — not in a sad way, [but] there was so much tribute being paid, and I’m like, ‘this is crazy.’ Because to my mind, I was just starting a job, you know?”

The union was brief; by 2016, Shad was replaced by CBC Radio 2 host Tom Power. Still, he had found a new outlet and audience beyond music — something that would resurface with his next project, the documentary series Hip-Hop Evolution. A group of Canadian filmmakers approached Shad about serving as the host, and he eagerly agreed.

“I love getting this view of hip-hop — really starting to understand how the music travelled from person to person and place to place,” he says. “I don’t think there’s a better film document about the origins of hip-hop that exists.”

“I love getting this view of hip-hop — really starting to understand how the music travelled from person to person and place to place. Like, I’m at 1520 Sedgwick with Kool Herc. This is wild.” – Shad

The series was a hit with critics and fans alike, featuring interviews with such seminal figures as Grandmaster Flash, Russell Simmons, and N.W.A. In addition to an International Emmy and Peabody Award, it earned two Canadian Screen Awards and was added to Netflix’s international roster. Already, it has been renewed for a second season, although Shad remains mum on which artists will be involved.

These days, the Toronto-based songwriter is gearing up for his latest creative endeavour, the full-length A Short Story About a War. Featuring appearances from familiar collaborators such as Eternia, Ian Kamau, Ric Notes, and DJ T.Lo, the album explores the concept of fear, among other things.

“The impostor syndrome never goes away,” he says. “The work is, I need to find something pure to give people, and I can’t do that if I’m distracted by myself.”

Along with fear, there’s hope. Gratitude, too.

“Now, when I look back, it’s kind of crazy to me,” says Shad. “I’ve just been able to do a lot of things that I feel grateful for every morning when I wake up. I got to share so much of my story and say so many things, and I did not anticipate any of it.”