In Conversation with Ashley, Founder of "The Sip Session"

Every great creative ecosystem relies on people who are willing to hold space for others. While local singer-songwriters often take center stage with their stories and songs, the independent media creators working behind the scenes are also vital to the communities being built through music. Enter Ashley, the creative force behind The Sip Session. Known for its cozy atmosphere, honest chats, and deep appreciation for local music, her platform has carved out a wonderfully authentic space. We sat down for this Q&A feature to turn the focus onto her journey, discussing the art of conversation, the grit of building a brand from scratch, and what it truly means to champion independent artists.

Rob Aguiar: Every great creative space starts with a spark. What was the original vision behind The Sip Session, and how has the concept evolved from your first few chats to what it is today?

Ashley: The original vision behind The Sip Session was always just being able to sit down with interesting people and learn about their story. But not in a super formal way, like friends having a chat over coffee. I want the artist to leave the conversation feeling seen and heard but also like they have a new friend. The heart of it is still that but it’s evolved so much more since I started it last October. 

I’ve had the chance to cover live events, a festival and have shorter conversations with artists. I think I’m starting to realize that The Sip Session doesn’t need to fit in one box. It can be meaningful and honest but also silly and fun. 

RA: A great interview relies entirely on making guests feel comfortable enough to open up. What’s your specific approach to creating an environment where people feel safe to share their honest stories and behind-the-scenes realities?

A: Honestly, genuine interest. Most artists I interview or reach out to, I find myself through social media, music I listen to or hearing them at a live event. So when I reach out, I already have some background on their work and enjoy what they do, which helps shape the questions and topics for our chat.

During our chat I listen and pivot based on their answer. If they don’t elaborate on something, we move on. I’m not here to push for the answer, I’m here to have the artist share the story the way they want to. That goes the other way too, if they open a door to something I wasn’t going to touch on, we roll with it. I also care how they’re represented and want them to be happy and proud of the conversation that comes out.

RA: Running Glimpse Productions, I know firsthand the kind of grit it takes to spotlight artists and build something independently. One thing I really admire about your approach is how many live events you attend to capture those on-the-spot clips and mini-interviews. How has that active, on-the-ground presence shaped the growth of The Sip Session?

A: Thank you! This wasn’t where I thought The Sip Session would go originally but honestly it is one of the more fun parts! It lets me get to know artists and build connections across the creative industry. Sometimes those short conversations are the best ones! 

I also love live events because you’re immersed in the crowd and artistry and get to see their work firsthand. Although I can’t make every show or showcase, I love supporting artists whenever I can.

Being at these events has also helped The Sip Session grow organically because people get to know me and see what I’m building in person. A lot of connections come from just being there.

RA: Weaving through everyone's stories and projects is such a unique experience. When you're constantly immersed in other people's creative wins and milestones, how does that collective energy fuel your own drive?

A: Great question! I feel like a big hype woman to artists haha. To even be a small part of their journey and help share their story is pretty cool. Watching people go after what they want and seeing that work pay off gives me the energy to keep going too. 

I said to a friend once that “creativity has no expiry date,” and I go back to that a lot. Hearing about their setbacks, wins and everything in between, just reinforces the fact that more of these stories need to be told.

RA: We're constantly told that attention spans are shrinking and that we need to trim everything down to fit a shorter mold. But seeing your longer-form chats is a great reminder of why those extended conversations matter. Call it old school, but there’s something deeply authentic about slowing down and really getting into a discussion. Why do you think those cozy, unhurried formats resonate so strongly when everything else online is rushing by?

A: Online everything is quick, flashy, grab you in the first 5 seconds or people scroll away. So being able to grab your favourite drink or a snack and listen to people have a relaxed chat about who they are, what they do and how they got there is refreshing.

Longer conversations help you get to know the person behind the work. You can’t always get that from a 30 second clip. Sometimes it’s the little side stories or unexpected moments in a chat that make it so interesting.

RA: What is a dream conversation, collaboration, or milestone you’d love to manifest for The Sip Session in the next chapter of your journey?

A: This is a tough one haha! If we’re talking dream conversation, Justin Bieber would be incredible. For collaboration I’d have to say chatting with the Jonas Brothers on their podcast would be insane. I’ve been a fan of both for years, so there would definitely be a lot of starstruckness to work through. For a milestone, being invited to cover a big event like the JUNOS with access to artists and a chance to bring a little coffee chat to the red carpet would be pretty neat.

It takes real grit, consistency, and a true love for the local scene to keep an independent platform moving forward—qualities Ashley brings to every single interview. Whether she's out working a live room or sitting down for a deep, unhurried chat, her work proves that authentic storytelling still has a vital home in our community.

Be sure to follow along with her journey and catch upcoming episodes on Instagram at @sipswithashley, and keep supporting the independent creators keeping our local culture vibrant.