TNN One on One Interview | Heroe’s Day Weekend 2025 with Kaelyn Kastle: Thank you! It’s just the beginning. It’s a journey.
TNN: Your rise has gone through the roof — congratulations. What would you say to aspiring artists who look up to you?
Kaelyn: I’ve been saying this for years — when you get to the top of one mountain, it’s time to start climbing another one. My father and I, and my late mother, always said, “It’s a journey.” And along the road, things will happen. But you pick yourself up and keep going. Some people’s journey is shorter than others. Mine’s been long and rough — but if it’s what you want, work for it. You’ll get there.
TNN: You mentioned your mother. That’s still a challenging space, right?
Kaelyn: Oh yeah. I’m still going through it. But my mother left a lot in me — she built a strong foundation. She taught me how to run a household, take care of my father and my brother, and stay on top of my business. She was my first manager, then my first assistant. Even when she couldn’t physically be there, she was always there. So yeah, it’s been rough, but she instilled strength in me.
TNN: And now, you’ve just completed a new video. I saw you sitting on a drop-top on Court Street in another video!
Kaelyn: [laughs] Yes! I love Court Street — I’m a Spinning Wheel girl. As soon as I turned 18, I was there with my daddy. So when I shot this video, I wanted to include the places that matter to me, especially when I’m hurting. Coming home resets me. It reminds me who I am.
TNN: And the song?
Kaelyn: It’s called “Big Pressure” featuring Bangladesh, the Grammy-winning producer who’s helped artists like Beyoncé and Lil Wayne hit #1. Now it’s my turn. Big Pressure is about stepping out, feeling yourself, owning your moment. We dropped it on Bermuda Day — that was huge for me. My mom was a Hot Pepper, so shoutout to Aunt Suzette for including me. It felt like everything came full circle.
TNN: Your father Jack— He’s your rock, your number one supporter?
Kaelyn: Always. He runs the fan club! Seriously — he didn’t even know I was walking Bermuda Day Parade until he saw me coming down the road. He was shocked. And shoutout to Aunt Helen Deal, who walked with me and supported me all the way.
TNN: What’s next for you?
Kaelyn: The “Big Pressure” video drops June 27th — mark your calendar. It’s full of culture, community, and familiar faces. I poured myself into it.
TNN: Before we go — you enjoying yourself back home on this Hero’s Day holiday weekend?
Kaelyn: I’m having a blast — even though I’m tired! Huge thanks to Nova Moss and the Bermuda Tourism Authority for bringing me in. I’m proud to be a local among international influencers. I’ll never forget where I came from. I love this island with all my heart.
TNN: Wherever you go, it’s to the top don’t forget us,
Kaelyn: Thank you. And don’t worry — I’ll never forget TNN. I’ve been with y’all since the beginning. You’ve been pushing through the noise, and that’s what it takes. I’m proud of you too.
Kaelyn: Just continued support. As I grow, I hope the support grows too. Big blessings to Bermuda — we’re going a long way.
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