Doh-Ski Interview: Navigating Independent Hip Hop and Building a Career in Canada

Name: Douglas James Woloski

Location: Regina Saskatchewan

Talent Name: Doh-Ski

Instagram: Dohski97

Category: Artist | Booking Agent

💬 INTRODUCTION

Hello! My name is Douglas James Woloski. I was born on September 15, 1997, in Regina, Saskatchewan, and I perform under the stage name Doh-Ski — a simple blend of the beginning of my first name and the end of my last.

I’m an aspiring rapper focused on turning long-term dreams into reality while raising my beautiful little girl, who motivates everything I do.

I’ve been making music for eight years and have toured nationwide across Canada three times — twice as an opener for Brothers Grim and Oliver Spitts, and once as a co-headliner with Oliver Spitts. I’ve also completed West Coast tours with Prada West and have spent the past two years touring across Canada with Snak The Ripper.

Alongside me on this journey is my partner in crime, Alex Tha Rippa — my brother from another mother.

🔥 THE PASSION

I believe real passion comes from knowing what it feels like to never have enough.

When I was a kid, my mother left an abusive relationship and moved two cities away to start over completely on her own. At one point, she worked three jobs just to provide for my brother and me — to make sure we lived in a safe neighborhood, attended a good school, and had the things we needed.

On the surface, things were okay. But even as kids, we could see the struggle she carried every day while trying to build a better life for us. If you ask me, she did an incredible job.

Watching her fight to succeed planted something deep in me — a constant drive to want more, not out of greed, but out of gratitude and responsibility. That’s where my hunger to be great was born. The pain became the fuel, and the struggle shaped the passion.

I turned that passion into something I always loved: music.

🚀 BUILDING THE DREAM

One moment that truly stands out for me was my first tour.

I was 19 years old, struggling heavily at the time — battling addiction, questioning who I was, and working through some very dark mental health challenges. One night, while sitting in a meeting trying to get my life back on track, I received a call that changed everything. It was Brothers Grim, asking if I wanted to join them on the Beverly Boys Tour.

As a first-time artist, tours cost money — money I didn’t have. I was newly getting clean and standing at a crossroads. I made the decision to get my act together and do whatever I could to make that opportunity real.

The day before the tour, I realized I still couldn’t come up with all the funds. I called Brothers Grim, told them my story, and explained where I was at in life. They took a chance on me — a broke kid from Saskatchewan who had never even left the province — and invited me to join a nationwide tour, trusting that we’d figure the rest out later.

For them, it wasn’t about money. It was about the love for the craft, and they saw that same love in me.

That tour helped me discover who I am and who I want to be. It didn’t just shape my career — it helped shape my life. I owe an enormous amount of gratitude to Komrade Grim, who showed belief in me when I needed it most. That moment will always be one of the most defining points of my journey.

🤝 NETWORKING SPOT

Honestly, most of the Canadian artists I’ve wanted to work with, open for, or tour alongside — I’ve already had the opportunity to do so, and I’m grateful for that.

One collaboration I’m especially looking forward to is creating a song with Snak The Ripper. After touring together, our bond has continued to grow, and I’m excited to see that connection carry over into the studio. Snak is a real, stand-up person, and the way our perspectives on life align makes me believe that chemistry will translate naturally into the music as well.

That’s something I’m genuinely looking forward to.

🚨 CLOSING

Motivation is something I struggle with daily. I’m the type of person who has to wake up every morning and actively choose to do the right things to build the life I want — and honestly, I wouldn’t have it any other way. The thought of failure keeps me moving forward, the joy that music brings my brother and I, Alex Tha Rippa, fuels the passion, and the drive to be better for my family keeps me grounded. These are the thoughts I return to every day to stoke the fire as I continue building ahead.

Above all, my beautiful little girl motivates everything I do.

COMETS QUESTIONS

COMET: How does being a single parent shape your creative process?

DOH-SKI: I think I’ve always been a conscious rapper, always making music about my feelings and what I’ve been through. So I don’t think becoming a single parent changed my creativity as much as it changed my mindset. It definitely affects my mental — because now there’s no option but to succeed. I have to succeed for my child.

COMET: Do you ever feel like there isn’t enough time for just you — and how do you handle that?

DOH-SKI: My OG, Komrade Grim, taught me three valuable lessons about music, and the first one was this: make time for yourself. Self-care matters, and it’s one of the best things you can do — not just for you, but for the people you love.

Being a parent, a touring artist, and working a day job to keep the dream alive means there’s next to no time for myself. But it’s the little things that make up the big things. Most of us drive home from work or run errands with either a “boohoo” or “finally freedom” attitude. Changing that simple drive or errand into you time can seriously change your life.

Self-care and self-awareness are the most important things. I’ve struggled with that many times and still practice it every day. The days I succeed at it usually flow a whole lot easier.

COMET: What has it been like investing in your dreams while also keeping up with everyday life?

DOH-SKI: Honestly, it’s a constant clusterfuck of scheduling, organization, dedication, and pure passion. It’s the willingness to bleed for the love of the music — and at the end of the day, it’s all worth it.

COMET: What would you tell someone who feels like they can’t afford to chase their passion?

DOH-SKI: That’s the second lesson my OG, Komrade Grim, taught me. If you don’t pop right away, can’t get sponsors or funding when you need it, but still want to chase your dreams — get a job. That also falls under taking care of yourself.

You don’t have to be bumming it out at your mom’s house trying to make it. Set your life up properly. Following your dreams becomes a lot easier when you take care of yourself first.

COMET: What does it feel like to be constantly on the move for work — living out of suitcases, driving long hours, chasing opportunities?

DOH-SKI: The dream coming true.

COMET: Do you ever struggle with loneliness or burnout while traveling for your craft, and how do you recharge?

DOH-SKI: That’s the best part about traveling with my best friend, Alex Tha Rippa. We keep each other in check, build each other up, and make sure we’re both taking the breaks we need to stay consistently charged.

COMET: Looking back, what’s something younger you wouldn’t believe about where you are today?

DOH-SKI: If I looked back at my younger self, I don’t think I’d believe that we actually set goals — and accomplished them. As a kid, I shot for the stars with touring and working with artists I loved. There are still a lot of goals left to complete, but we’ve already achieved so many.

COMET: What message do you hope people take away from your music when they hit play?

DOH-SKI: I hope people take away that no matter what’s happened to you in your life, it doesn’t mean it’s over. Get back up, keep grinding, and build a new life.

COMET: The Canadian hip-hop scene keeps evolving — what role do you see yourself playing in that movement?

DOH-SKI: As the Canadian hip-hop scene continues to evolve, I want my role to grow the same way it has already — just on a larger scale. Being both an artist and a booking agent is a beautiful journey. It’s tough at times, but overall, it’s been an incredible experience.

ANYTHING ELSE YOU’D LIKE TO INCLUDE?

DOH-SKI: You can find me on all platforms. On music platforms, search Doh-Ski. On social media, you can find me under dohski97. Here are links to my two favourites for anyone who wants to tap in and follow the journey

Spotify: Doh-Ski | Instagram: Dohski97

Closing things out with a behind-the-scenes clip from a past project with Comets Crew