Rollin' with Kyle + Sheldon

We first met Kyle and Sheldon through Instagram and linked up at a local skate park years ago for a spontaneous photo session. Since then, we’ve watched them grow—not just as creators, but as people who bring their own energy and authenticity to everything they do. Together, they’ve built a style that perfectly blends motion, community, and creativity. Every shoot with these two is a mix of laughter, quick ideas, and skate tricks that somehow always land just right. It’s never a dull content session when we connect—it’s honestly the highlight of any Edmonton visit.

Skateboarding is all about motion—what are your favourite ways to capture that energy and movement in your content?

Kyle: Skateboarding is all about motion! I take this as an advantage for my content style, always showing quick, flashy styles to get my audience's attention. I also like to include fast movements or have Sheldon follow me while I skate! Once I get to my computer, I like to add transitions, speed ramps and motion blur to add an extra effect of motion.

Do you find filming each other makes it easier to highlight motion, or do you approach self-shot content differently?

Sheldon: Filming each other lets us create different types of clips than when we film alone. When we are together, we can do longer shots of our skating to show off more tricks and steps in one long shot, and create natural transitions from one clip to another. Filming alone allows us to experiment in different ways, like using the ends of the frame to set up the next shot, using jump cuts to make a high-paced video, or using the stability of a tripod to insert interesting effects in the editing process.

Fashion is such a big part of skate culture—how do your personal styles show up in the content you create?

Kyle: Fashion is important for my content creation. I use it to keep my audience attracted to my video, and it helps them know who they're watching. This gives me a signature style that people can recognize me by.

Content creation can be a grind—what helps you stay inspired and mentally grounded when you're in a creative rut?

Sheldon: Keeping in mind that my videos don't always have to be absolutely perfect and can be as simple as the process of trying to land a new trick or more heavily edited, shot and thought out like a short story. I do content creation as a form of journaling, artistic expression and fun. If a project becomes very stressful, I can always come back to it later or re-shoot what I need to at a later time. Rushing things to appease the algorithm or meet others' expectations won't benefit me in the long run.

When you're working with brands like Social Made Local, what makes a collaboration feel authentic and fun for you?

Kyle: Working with brands, I always make sure they allow me to include skating because that's what I'm about. They need to understand my needs before I agree to collaborate, as well as something my audience would enjoy watching.

How do you balance staying true to your own creative vision while also delivering what a brand is looking for?

Sheldon: When working with brands, both parties need to be clear on their visions and what they want or need out of a piece or pieces of content. Communication is the main factor in producing content that both sides are happy with. Bouncing ideas off each other, being open to what will and won't work, and being willing to compromise with each other to make sure everyone's needs are met are vital to working together in a healthy way.

Skateboarding often builds tight-knit groups—what does community mean to you both, on and off the board?

Kyle: The community means a lot to me. I love to motivate anyone around me. My audience has grown to the point where locals see my content, and I want to make sure they are seen, and if they have any questions, I will gladly help them out.

Has creating content together changed the way you see skateboarding, fashion, or even your own self-expression?

Sheldon: Creating content together has helped me progress my skateboarding in a way that skating alone does not. Being more open and creative with tricks and the possibilities of taking my skating in different directions, like street and park skating. Having someone to create content with also helps me feel more confident about my sense of style and wearing what I'm comfortable in, rather than dressing in a way that society expects or to meet certain social standards. Feeling accepted in other aspects of your life, like creativity and fashion, leads to feeling more confident in expressing yourself in your content and around others more.

What advice would you give to other creators who want to capture motion—whether that's skating, dancing, or just everyday movement—in a way that feels real and exciting?

Kyle: The best advice I'd give to any creator is that in the action/sport scene, just be yourself. Engage with your niche and help each other grow. The worst part about content creation is being afraid to post, but never let that hold you back. Everything is content!

How do you maintain your positivity while you're engaged with social media, especially when it's easy to fall into comparison or doom scrolling?

Sheldon: Maintaining positivity can be a huge struggle when engaging with social media on a regular basis. I try to remind myself that another person's accomplishments are not my failures and that everyone has different goals and mindsets when creating content. Some just want to show success and the happy times, others are more focused on the process and grind, most are in between, but it's important to remember that the only person you want to try to impress is yourself, show up for yourself and do your best, whatever that means to you.

You can find Kyle on Instagram at @ky.tremmy and Sheldon at @sheldz.skates.

The boys are wearing the Happy Tee + Hoodie and the Connection Tee + Hoodie, two of our favourite designs that celebrate joy, friendship, and creative connection. We had the pleasure of filming with them in Edmonton at the Muttart Conservatory and Downtown Edmonton, capturing moments that show why collaboration is at the heart of everything we do.

Watch their full Creator Story on YouTube.