Alright – so today we’ve got the honor of introducing you to Dj Stiles. We think you’ll enjoy our conversation, we’ve shared it below.
DJ, appreciate you joining us today. Do you think your parents have had a meaningful impact on you and your journey?
As an artist-entrepreneur, education is something I reflect on a lot—especially in the context of today’s economic realities. While I didn’t get all the lessons I needed in school, I was lucky to learn some key financial truths from my parents, especially my dad, who worked in finance and has a knack for keeping things simple. His advice? Live below your means to save more (harder than ever, I know). Keep housing costs to about a third of your income (also a challenge). Learn the basics like filing taxes, saving, investing, and understanding interest rates.
When I rented my first apartment in the mid-noughties, a studio apartment beside a bus terminal and a 5-minute walk to work for the bargain price of $550/month, my dad quietly hated it. I told him I was just following his teachings to live small and save big. It worked. I bought my first home in 2012, a fixer-upper condo in downtown Toronto. Following his advice to plan for rising interest rates, I bought something I could afford long-term and even rented out the second bedroom. That room has been a lifesaver—first as rental income, then as my art studio when I lost my rented art studio during the pandemic.
My takeaway? Financial literacy isn’t just nice to have, but it’s essential. Whether it’s learning about mortgages, interest rates, or saving strategies, this stuff matters. And if you’re not learning it in school, find a way to teach yourself. It’s the kind of education you can’t afford to miss.
Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.
I’m DJ Stiles, not a disc jockey, but an artist-entrepreneur named Douglas John Stiles. I’m based in Toronto, Canada and Medellin, Colombia (my partner is Colombian-Canadian). I’ve definitely been creative my whole life. My high school art class was part theory, part practice. When I first studied pop art, I was in love. I thought, ‘This is art? This is amazing!’ I love the bold graphic nature and especially the social commentary. I later studied art history and architecture at the University of Toronto, with a fondness for the modern era. I also hold a Master’s in Environmental Studies, specializing in urban planning, from York University.
I paint original imagery of the queer experience in a pop art style, characterized by carefully curated colour palettes and often stylized, reductionist portraiture. I find inspiration in the pop art movement, the male form, urbanity, the City of Toronto, magical realism, Colombian street art and a never-ending parade of inside jokes. My subject matter often includes queer men, glamourous women, trans folk and fierce drag performers. Sometimes my subject matter ventures into NSFW.
I generally paint with acrylic paint on canvases of varying sizes. I’ve participated in dozens of group shows (often at Super Wonder Gallery on Bloor Street and the former Freedom Factory on Dovercourt Road) and I’ve also produced 5 solo shows to date. I’m probably most known for ‘Drag Pop Realness Inspired By Pantone’ in 2018. I photographed 12 Toronto drag performers, then painted them in shades of various colours of the year by Pantone, to match the vibe or personality of the individual performers, all styled like a paint swatch. The collection is sold, but you can see two of these pieces (plus several others of my paintings) on display at Maple Leaf Medical Clinic on College Street.
I also offer high quality photo prints or prints on canvas, of all of my original paintings.
Several years ago, I was thinking about how many people my age were more likely to spend money on fashion than art, so I started combining the two. I started painting portraits on denim jackets and people love them. And I love when my art becomes wearable and thus far more visible in the public realm. I just finished a Christmas commission of a denim jacket with portraits of Tom Jones and the client’s adorable late cat.
I’m also exploring 3D printing. I designed a number of pop art earrings that I’m currently working on producing. I expect the first collection will be ready to wear this summer. I even got my ears pierced recently so I would be able to wear my own designs.
What’s been the best source of new clients for you?
The best sources of new clients have been word of mouth, networking, and social media particularly Instagram as it’s my primary platform (I’m an elder millennial). During the pandemic, Toronto had one of the longest lockdowns in the world, so like most people, I was at home / on my balcony an awful lot. One day, a woman on a balcony of the building next door yelled over at me. She could see my art hanging in my living room through the window and she wanted to know more about it. So we met downstairs, on opposite sides of the fence (6 feet apart, of course) and chatted about art for a while. She ended up commissioning a floral and yoga-themed denim jacket for her partner. It was our conversation and our connection that led to her requesting a commission.
I also consume as much local art as I can. I go to local shows and meet other artists, gallerists, collectors and enthusiasts. People are more likely to purchase art when they know the story and the creator behind it. Creating connections creates a sense of community. This networking has led to sales, commissions and participation in new galleries and events.
I have amassed a collection of images of my art over the years on Instagram. I use it as a catalogue that people can scroll through for inspiration. I receive the majority of commission requests through Instagram.
It can be so challenging to produce and market, while also just trying to live life. There’s so much more all artists could do to market their art, including myself. My partner works in digital marketing, so he’ll be coaching me to grow my online presence in 2025.
How can we best help foster a strong, supportive environment for artists and creatives?
First of all, it’s important to shift perception. Artists need to be recognized as vital contributors to society and advocate for policies that support dignified, sustainable creative careers. Education is critical, particularly the incorporation of business literacy into arts education, empowering artists with the skills to thrive professionally. With rapid re-development of the city, existing creative spaces need to be protected. We can implement stronger legislation to preserve existing art venues and collaborate with organizations like Artscape to develop affordable studios and living spaces. The City’s Official Plan could also be strengthened to protect these existing creative spaces and/or incentivize developers to build new creative spaces in new developments. We can also continue to grow the City’s public art program for new developments and StreetARToronto program, enriching communities and public spaces.
The City of Toronto recently approved a cultural action plan called Culture Connects: An Action Plan for Culture in Toronto, to build a more inclusive and vibrant cultural ecosystem. The plan calls for things like more accessible and affordable cultural spaces all throughout the city and focuses on equity, diversity, inclusion and increased financial support for arts organizations to foster growth and innovation. It’s a truly inspiring plan. By valuing and investing in artists, we create a thriving cultural landscape that benefits everyone.
Contact Info:
- Website: https://www.djstiles.ca
- Instagram: @djstiles
Image Credits
n/a