Pop Up Conversations

From Kingston, Jamaica to stages across Canada, Sky Star shares a story shaped by survival, faith and music.He reflects on growing up in hardship, finding music as his escape, and building a path that has led to a Juno nomination and a number one reggae record in Canada.A conversation about where it started, what it took to keep going, and what comes next.

He calls himself the most successful artist you’ve never heard of.And when you hear his story, it makes sense.Caleb Hart opens up about growing up in Tobago, the path he was on, and how leaving everything behind changed the trajectory of his life. Weeks after arriving in Canada, people he grew up with were gone. That moment changed everything.What followed wasn’t instant success. It was perspective, survival, and eventually… music.This is a conversation about starting over, carrying what you’ve been through, and turning it into something meaningful.

Sam Roberts joins Pop Up Conversations to reflect on Chemical City 20 years later.From songwriting and legacy to identity, history, and the meaning songs take on over time, this is a thoughtful conversation on what it means to keep growing as an artist while staying true to the music.

In this episode of Pop Up Conversations, singer-songwriter Kaeley Jade reflects on the journey behind her upcoming album, The Great Unknown.From her prairie roots to the evolution of her songwriting, this conversation explores vulnerability, transformation, touring, artistry and what it takes to build a lasting creative life.

Nuela Charles joins Pop Up Conversations to reflect on creativity, independence, and what it meant to return to music on her own terms.From stepping away from industry expectations to reconnecting with the roots of why she started, this conversation offers an honest look at the journey behind NU2U and the importance of creating from a place of peace.

In this episode of Yarn, Nuela Charles and Dana Wylie of Secondhand Dreamcar come together for an artist to artist conversation about music, recognition and the journey behind the work.Both artists are JUNO nominees, but this conversation goes beyond the moment. It explores what it takes to build a career in music, the balance between independence and collaboration, and the experience of creating from Edmonton.For Nuela, this project marks a return to self through writing and recording at home. For Dana, the process is shaped by collaboration within a band and the shared responsibility of creating together.Together, they reflect on craft, perspective and staying true to the work.Listen now on the Pop-Up Conversations feed.This is Yarn. Artists in conversation.

Dan Davidson joins Pop-Up Conversations for a thoughtful discussion about music, career longevity, and staying grounded in an unpredictable industry.He reflects on his journey from rock bands to country success, the unexpected impact of his platinum single Found, and the challenge of continuing to create after reaching major milestones.The conversation also explores the personal side of his life, including fatherhood, family priorities, and how those experiences shape the music he writes today.It’s an honest look at creativity, resilience, and what it means to keep evolving as an artist.

In this intimate conversation, Mighloe opens up about the tension between who she is and who the world sees.Behind the confident performer is a quieter, more introspective self. For years, music has been her therapy — the place where she says what she struggles to speak aloud. Writing becomes a way to confront comfort, process relationships, and uncover truths she sometimes didn’t even know she was carrying.After a two-year pause, she returns with her new single, “Noches,” a hazy, cinematic release that signals both a sonic shift and a personal re-emergence. The song reflects her desire to step out of her shell, to move beyond fear and industry packaging, and to embrace creative freedom without needing to fit a single genre.Together, we explore vulnerability in performance, the emotional cost of honesty, the difference between persona and self, and why this new chapter is less about chasing pop stardom and more about building something authentic on her own terms.At its core, this episode is about choosing courage over comfort — and allowing growth to reshape the art.

In this episode of Pop Up Conversations, Efe Mike-Ifeta sits down with Kelsi Mayne to talk about songwriting without emotional distance. Kelsi reflects on writing from lived experience, using music as a way of making meaning in real time, and offering songs in the hope that someone else might hear them when it matters most.

What does it mean to stay?In this episode of Pop Up Conversations, Lameese Smaili speaks with AV and The Inner City about music as presence rather than performance.From porch concerts to sustained community practice, the conversation explores listening, dignity, and the quiet work of building trust over time.Staying, Listening, and the Work of Presence

Three years after our first interview, Maddisun returns to Pop-Up Conversations with her most personal and confident chapter yet. Fresh off an intense year of nonstop touring, a sold-out hometown album release show, and the unveiling of her new record The Pages, she sits down to talk about what it truly means to grow, return home, and step fully into her identity as an artist.In this episode, Maddisun opens up about the magnetic pull of her mountain hometown, the community that raised her, and the deep sense of belonging that keeps calling her back even as her career takes her to Toronto, New York, L.A., and beyond. She reflects on the journey behind The Pages: learning to trust herself, embracing vulnerability, shedding outside expectations, and allowing herself to be fully seen—perhaps for the first time.We talk about creativity, intuition, fear, resilience, legacy, and the moment an artist realizes they’ve finally become who they always imagined. Maddisun’s clarity, optimism, and grounded spirit shine through as she shares the stories, emotions, and revelations that shaped this new era.This is a conversation about turning the page, finding your voice, and stepping into the light.Listen now to Maddisun’s full episode on Pop-Up Conversations—available on Spotify, Apple Podcasts, and wherever you get your podcasts.

Emily Steinwall doesn’t just make music — she searches for truth through sound. From her cosmic album Welcome to the Garden to her roots in a musical family, Emily’s path has always been about more than recognition or industry trends. In this episode, she shares how a childhood concert shaped her, why she studied jazz saxophone, what Toronto means to her artistry, and how she navigates the many roles of being a modern musician. At the heart of it all is her philosophy: creating timeless music that connects soul to soul.

Canadian singer-songwriter Joshua Hyslop sits down to share his journey — from finding his start in music to building a career in the indie folk scene. In this conversation, Joshua opens up about the challenges of staying true to yourself as an artist, balancing creativity with career pressures, and what it means to write music that connects deeply with listeners.Known for his heartfelt lyrics and authentic sound, Joshua has built a loyal audience across Canada and beyond. Here, he reflects on freedom, honesty, and the craft of songwriting while offering insight into what it takes to sustain a meaningful music career.✨ What you’ll hear in this episode:How Joshua Hyslop got his start as a songwriterBuilding a career in indie folk musicStaying authentic to your voiceThe balance between creativity and industry expectations About Joshua HyslopJoshua Hyslop is a Canadian indie folk artist whose music blends honest storytelling with emotional depth. With multiple albums and millions of streams worldwide, he continues to inspire fans with songs rooted in vulnerability, freedom, and connection.👉 If you enjoy conversations about music, storytelling, and creative careers, don’t forget to like, subscribe, and share this episode.#JoshuaHyslop #IndieFolk #SingerSongwriter #MusicPodcast #Songwriting #CanadianMusic

In this deeply personal conversation, artist and songwriter Dahlia Fernandes opens up about the spiritual and creative journey behind her latest single Good Love and upcoming album The Sound of My Love. She reflects on ancestral influence, letting go of ego, and what it means to create music as a form of healing — not just for herself, but for others. From divine timing to reclaiming her name and language, Dahlia takes us behind the music to explore how purpose, patience, and presence have shaped her art.Listen wherever you get your podcasts, watch on YouTube, and follow @popupconversation on Instagram for more.

Venezuelan-Canadian artist Jace Carrillo is crafting a cinematic universe with Phenomena, his sophomore album blending Latin pop, R&B, and soulful storytelling.In this episode, Jace talks about:• His viral single Desapareces• Performing on La Voix Québec while still learning French• Gospel and R&B influences that shaped his sound• Building visuals and working with Grammy-winning collaborators• What authenticity means in today's music industry🎧 Listen now and discover how Jace is breaking genre boundaries — and making bold moves in Canada’s music scene.Support Jace:🎶 Stream Phenomena on Spotify/Apple📱 Follow Jace on socials: @jacecarrillo🎬 Watch his music videos on YouTubeSince this convo, Jace has kept it moving — dropping new music, leveling up his visuals, and continuing to create really dope stuff. Be sure to check him out and show some love.