We had the good fortune of connecting with Dempsey Bolton and we’ve shared our conversation below.

Hi Dempsey, we’d love to hear about how you approach risk and risk-taking
The way I see it, my whole career has kind of been defined by risk; I started producing music when I was in school studying Astrophysics and the University of Alberta. By the end of my degree I realized that I needed to pursue a career in music if I wanted to be happy. So instead of following through with the Master’s degree I’d lined up, after I graduated I completely switched gears and started taking music way more seriously. Eventually, I got the opportunity to work with Trey Mills of Unbound by Sound and moved to Calgary to have my own studio. In hindsight, it was a pretty ridiculous idea because I didn’t know anyone in the city besides Trey and it was in the middle of the pandemic back in July of 2020 but it ended up being the best decision I’d ever made. I’ve grown so much in the past two years as an artist and as a person so in a way I guess I can attribute that to taking risks.

Alright, so let’s move onto what keeps you busy professionally?
It feels strange to reflect on my journey as an artist because I have such high ambitions and I feel like I’m always trying to achieve more and more. With that being said, I think the reason I am where I am today is because I have an insatiable (almost-neurotic at times) drive to get better. I’m not the most business savvy or the most well-connected but I’ve worked myself into a place where I think my skills as an artist and a producer are starting to speak for themselves. I’ve always been of the mindset that if you’re the best at what you do then everything else will fall into place. And mind you, I’m no where near the best at anything I do (hello Jacob Collier) but I’m on my way and a little bit closer every day. The biggest challenge with any creative career is always the endless rejection that you have to endure but I think that’s why I’m so drawn to the grind. I have this idea that if I keep getting better, eventually I’ll make something that’s undeniable. Until then, I’m just striving for making something that I love.

If I’ve learned anything over the course of my journey it’s that it’s never too late to learn something new. I started everything relatively late; production at 23, piano at 25, bass at 27, drums at 28. I’m still making a living as an artist and a producer doing every single one of those things. So if anyone is worried they’re too late, they’re not. At the risk of sounding like a Hallmark special, you just have to put in the work and believe.

If you had a friend visiting you, what are some of the local spots you’d want to take them around to?
I’m a little bit of a homebody (or more accurately, a studio-body) but if I were to take friends somewhere for a good time I think it would have to be the mountains. It’s one of the best things about living in Calgary is to be able to drive an hour and be surrounded by the Rockies. For me, that would be a great time. There are also some great spots in the city though: I have a lot of love for Koi Cafe downtown. The vibes are just so inclusive and there’s so much talent that goes through that venue. The food is amazing too so that doesn’t hurt.

Who else deserves some credit and recognition?
There are so many people who have offered so much support but I wouldn’t be where I am right now without the support from my partner Kendra. As cliche as it sounds, she really is my rock and one of my biggest motivators to succeed.

In addition, my parents taught me so much about morality and how to be kind and have always supported me and my business endeavors. Trey Mills has been somewhat of a mentor to me and working with him has given me so many opportunities that I otherwise would not have had. Lastly, my friend circle keeps me sane and I have so much love for everyone in my life.

Website: https://www.dempseybolton.com

Instagram: https://www.instagram.com/dempsey_bolton/

Youtube: https://www.youtube.com/c/DempseyBolton

Image Credits
Orein Ferdinandus Eric Belliveau

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